CA2461360A1 - 3-pyridyl or 4-isoquinolinyl thiazoles as c17,20 lyase inhibitors - Google Patents
3-pyridyl or 4-isoquinolinyl thiazoles as c17,20 lyase inhibitors Download PDFInfo
- Publication number
- CA2461360A1 CA2461360A1 CA002461360A CA2461360A CA2461360A1 CA 2461360 A1 CA2461360 A1 CA 2461360A1 CA 002461360 A CA002461360 A CA 002461360A CA 2461360 A CA2461360 A CA 2461360A CA 2461360 A1 CA2461360 A1 CA 2461360A1
- Authority
- CA
- Canada
- Prior art keywords
- pyridyl
- thiazole
- bond
- etoac
- cndot
- 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
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 title claims abstract description 75
- 239000002697 lyase inhibitor Substances 0.000 title description 7
- MOYQLVVBWFGTJI-UHFFFAOYSA-N 4-isoquinolin-1-yl-1,3-thiazole Chemical class S1C=NC(C=2C3=CC=CC=C3C=CN=2)=C1 MOYQLVVBWFGTJI-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 153
- 238000000034 method Methods 0.000 claims abstract description 93
- 102000004317 Lyases Human genes 0.000 claims abstract description 39
- 108090000856 Lyases Proteins 0.000 claims abstract description 39
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract description 35
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 28
- 206010060862 Prostate cancer Diseases 0.000 claims abstract description 24
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 24
- 201000011510 cancer Diseases 0.000 claims abstract description 21
- 206010006187 Breast cancer Diseases 0.000 claims abstract description 18
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- -1 4-isoquinolinyl moiety Chemical group 0.000 claims description 107
- 229910052760 oxygen Inorganic materials 0.000 claims description 92
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 74
- 229910052736 halogen Inorganic materials 0.000 claims description 69
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 150000002367 halogens Chemical class 0.000 claims description 50
- 239000000126 substance Substances 0.000 claims description 42
- 125000004076 pyridyl group Chemical group 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 38
- 150000001204 N-oxides Chemical class 0.000 claims description 32
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 22
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 22
- 125000001188 haloalkyl group Chemical group 0.000 claims description 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
- 230000002401 inhibitory effect Effects 0.000 claims description 16
- 150000001408 amides Chemical class 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 230000036961 partial effect Effects 0.000 claims description 8
- 125000000565 sulfonamide group Chemical group 0.000 claims description 8
- 150000003852 triazoles Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 150000003557 thiazoles Chemical class 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 6
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 4
- 241000282465 Canis Species 0.000 claims description 3
- 241000283073 Equus caballus Species 0.000 claims description 3
- 241000282324 Felis Species 0.000 claims description 3
- 241000288906 Primates Species 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims 19
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 16
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 3
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 abstract description 17
- 108090000790 Enzymes Proteins 0.000 abstract description 17
- 125000001424 substituent group Chemical group 0.000 abstract description 12
- 239000003112 inhibitor Substances 0.000 abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 863
- 235000019439 ethyl acetate Nutrition 0.000 description 427
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 225
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 156
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 156
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 151
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 139
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 125
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 121
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 88
- 239000000243 solution Substances 0.000 description 85
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 84
- 239000000543 intermediate Substances 0.000 description 81
- 238000004809 thin layer chromatography Methods 0.000 description 80
- 239000000203 mixture Substances 0.000 description 78
- 229910052757 nitrogen Inorganic materials 0.000 description 77
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 76
- 238000002360 preparation method Methods 0.000 description 75
- 125000001309 chloro group Chemical group Cl* 0.000 description 71
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 67
- 238000006243 chemical reaction Methods 0.000 description 65
- 239000007787 solid Substances 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- 239000002904 solvent Substances 0.000 description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- 229910001868 water Inorganic materials 0.000 description 46
- 239000011541 reaction mixture Substances 0.000 description 43
- 238000007429 general method Methods 0.000 description 41
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 41
- 230000000694 effects Effects 0.000 description 40
- 238000005160 1H NMR spectroscopy Methods 0.000 description 39
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 39
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 39
- 230000015572 biosynthetic process Effects 0.000 description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 37
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 33
- 239000003098 androgen Substances 0.000 description 33
- 239000000047 product Substances 0.000 description 32
- 239000003921 oil Substances 0.000 description 31
- 235000019198 oils Nutrition 0.000 description 31
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 30
- 125000001246 bromo group Chemical group Br* 0.000 description 30
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 29
- 201000010099 disease Diseases 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 26
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 23
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 23
- 238000011282 treatment Methods 0.000 description 23
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- 239000012044 organic layer Substances 0.000 description 21
- 238000010992 reflux Methods 0.000 description 21
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-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
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 20
- 239000000725 suspension Substances 0.000 description 20
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 19
- 108010015330 Steroid 17-alpha-Hydroxylase Proteins 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 18
- 102000001854 Steroid 17-alpha-Hydroxylase Human genes 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
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 18
- 238000010898 silica gel chromatography Methods 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 17
- 101150041968 CDC13 gene Proteins 0.000 description 16
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 16
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
- 125000004093 cyano group Chemical group *C#N 0.000 description 15
- 239000000262 estrogen Substances 0.000 description 15
- 229940011871 estrogen Drugs 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 15
- 238000004128 high performance liquid chromatography Methods 0.000 description 15
- 238000000746 purification Methods 0.000 description 15
- WEGYGNROSJDEIW-UHFFFAOYSA-N 3-Acetylpyridine Chemical compound CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-UHFFFAOYSA-N 0.000 description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 14
- 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
- 230000001419 dependent effect Effects 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- 229940030486 androgens Drugs 0.000 description 13
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- 239000003814 drug Substances 0.000 description 12
- 230000001404 mediated effect Effects 0.000 description 12
- 239000002207 metabolite Substances 0.000 description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 229910052720 vanadium Inorganic materials 0.000 description 12
- 229910004373 HOAc Inorganic materials 0.000 description 11
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 239000000186 progesterone Substances 0.000 description 11
- 229960003387 progesterone Drugs 0.000 description 11
- 239000011593 sulfur Substances 0.000 description 11
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 239000003795 chemical substances by application 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
- 229940079593 drug Drugs 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229960002478 aldosterone Drugs 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 208000035475 disorder Diseases 0.000 description 9
- 238000001914 filtration Methods 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
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 9
- 239000002395 mineralocorticoid Substances 0.000 description 9
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 9
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 229960001866 silicon dioxide Drugs 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 7
- NRGXDHGSEPOAHR-UHFFFAOYSA-N 2-chloro-1-(4-methylpyridin-3-yl)ethanone Chemical compound CC1=CC=NC=C1C(=O)CCl NRGXDHGSEPOAHR-UHFFFAOYSA-N 0.000 description 7
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 7
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 7
- 206010020772 Hypertension Diseases 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- RWRIWBAIICGTTQ-UHFFFAOYSA-N anhydrous difluoromethane Natural products FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 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 7
- 239000003862 glucocorticoid Substances 0.000 description 7
- 231100000252 nontoxic Toxicity 0.000 description 7
- 230000003000 nontoxic effect Effects 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 229960003604 testosterone Drugs 0.000 description 7
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 6
- WPCSNGBKVXKBPU-UHFFFAOYSA-N 2-pyridin-3-yl-1,3-thiazole Chemical class C1=CSC(C=2C=NC=CC=2)=N1 WPCSNGBKVXKBPU-UHFFFAOYSA-N 0.000 description 6
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 6
- 108010080146 androgen receptors Proteins 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 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
- 239000005457 ice water Substances 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 238000004949 mass spectrometry Methods 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 150000003431 steroids Chemical class 0.000 description 6
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 5
- 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
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
- 102100032187 Androgen receptor Human genes 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000000556 agonist Substances 0.000 description 5
- 230000004075 alteration Effects 0.000 description 5
- 235000019270 ammonium chloride Nutrition 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
- 230000002280 anti-androgenic effect Effects 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 235000012000 cholesterol Nutrition 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 229960000249 pregnenolone Drugs 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- XQWBMZWDJAZPPX-UHFFFAOYSA-N pyridine-3-carbothioamide Chemical class NC(=S)C1=CC=CN=C1 XQWBMZWDJAZPPX-UHFFFAOYSA-N 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000003765 sweetening agent Substances 0.000 description 5
- 229940037128 systemic glucocorticoids Drugs 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 230000000699 topical effect Effects 0.000 description 5
- PRXNKYBFWAWBNZ-UHFFFAOYSA-N trimethylphenylammonium tribromide Chemical compound Br[Br-]Br.C[N+](C)(C)C1=CC=CC=C1 PRXNKYBFWAWBNZ-UHFFFAOYSA-N 0.000 description 5
- XTHPHCBLHLOEID-UHFFFAOYSA-N 1-(4-ethylpyridin-3-yl)ethanone Chemical compound CCC1=CC=NC=C1C(C)=O XTHPHCBLHLOEID-UHFFFAOYSA-N 0.000 description 4
- LCEINQHGZAFADC-UHFFFAOYSA-N 1-(4-methylpyridin-3-yl)ethanone Chemical compound CC(=O)C1=CN=CC=C1C LCEINQHGZAFADC-UHFFFAOYSA-N 0.000 description 4
- ZMEMLNQJRMTRCU-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(4-chloropyridin-3-yl)-1,3-thiazole Chemical compound C1=CC(Cl)=CC=C1C1=CSC(C=2C(=CC=NC=2)Cl)=N1 ZMEMLNQJRMTRCU-UHFFFAOYSA-N 0.000 description 4
- ORFGHTLYEABIRY-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=CC(Cl)=CC=2)=CS1 ORFGHTLYEABIRY-UHFFFAOYSA-N 0.000 description 4
- KTWNITSKCILMPX-UHFFFAOYSA-N 4-[2-(4-methylpyridin-3-yl)-1,3-thiazol-4-yl]benzonitrile Chemical compound CC1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)C#N)=CS1 KTWNITSKCILMPX-UHFFFAOYSA-N 0.000 description 4
- RTSQDAYNVBKKEJ-UHFFFAOYSA-N 4-cyclopropylpyridine-3-carbothioamide Chemical compound NC(=S)C1=CN=CC=C1C1CC1 RTSQDAYNVBKKEJ-UHFFFAOYSA-N 0.000 description 4
- RTVZZFXJASCNCE-UHFFFAOYSA-N 4-methoxypyridine-3-carbonitrile Chemical compound COC1=CC=NC=C1C#N RTVZZFXJASCNCE-UHFFFAOYSA-N 0.000 description 4
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 4
- WDIPQCJUEWOCJT-UHFFFAOYSA-N 4-methylpyridine-3-carbothioamide Chemical compound CC1=CC=NC=C1C(N)=S WDIPQCJUEWOCJT-UHFFFAOYSA-N 0.000 description 4
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000000579 Gonadotropin-Releasing Hormone Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 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
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 101000857870 Squalus acanthias Gonadoliberin Proteins 0.000 description 4
- 230000002159 abnormal effect Effects 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 230000001919 adrenal 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
- 230000008901 benefit Effects 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 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
- 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 4
- 238000001035 drying Methods 0.000 description 4
- 238000000132 electrospray ionisation Methods 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 235000013355 food flavoring agent Nutrition 0.000 description 4
- 235000003599 food sweetener Nutrition 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
- 125000001475 halogen functional group Chemical group 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000003840 hydrochlorides Chemical class 0.000 description 4
- 239000001257 hydrogen Substances 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
- 229910052740 iodine Inorganic materials 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 238000006977 lyase reaction Methods 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 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
- 210000002307 prostate Anatomy 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 239000003270 steroid hormone Substances 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
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- XGDKYGUSYJOLKG-UHFFFAOYSA-N 1-(4-propylpyridin-3-yl)ethanone Chemical compound CCCC1=CC=NC=C1C(C)=O XGDKYGUSYJOLKG-UHFFFAOYSA-N 0.000 description 3
- ABTYPOQRRMEIMH-UHFFFAOYSA-N 1-chloro-3-(4-chlorophenyl)propan-2-one Chemical compound ClCC(=O)CC1=CC=C(Cl)C=C1 ABTYPOQRRMEIMH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- UPUWMQZUXFAUCJ-UHFFFAOYSA-N 2,5-dihydro-1,2-thiazole Chemical compound C1SNC=C1 UPUWMQZUXFAUCJ-UHFFFAOYSA-N 0.000 description 3
- FLAYZKKEOIAALB-UHFFFAOYSA-N 2-bromo-1-(4-chlorophenyl)ethanone Chemical compound ClC1=CC=C(C(=O)CBr)C=C1 FLAYZKKEOIAALB-UHFFFAOYSA-N 0.000 description 3
- WDTSYONULAZKIE-UHFFFAOYSA-N 2-bromo-1-pyridin-3-ylethanone;hydron;bromide Chemical compound [Br-].BrCC(=O)C1=CC=C[NH+]=C1 WDTSYONULAZKIE-UHFFFAOYSA-N 0.000 description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 3
- ZPDVOJVKZUSZPT-UHFFFAOYSA-N 4-(4-fluorophenyl)pyridine-3-carbonitrile Chemical compound C1=CC(F)=CC=C1C1=CC=NC=C1C#N ZPDVOJVKZUSZPT-UHFFFAOYSA-N 0.000 description 3
- GAHLSEZBZPQUGB-UHFFFAOYSA-N 4-[(4-chlorophenyl)methyl]-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(CC=2C=CC(Cl)=CC=2)=CS1 GAHLSEZBZPQUGB-UHFFFAOYSA-N 0.000 description 3
- VXSUXCUEKLHRHO-UHFFFAOYSA-N 4-[2-(4-cyclopropylpyridin-3-yl)-1,3-thiazol-4-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CC2)=N1 VXSUXCUEKLHRHO-UHFFFAOYSA-N 0.000 description 3
- LNJAEKBOQMMMQB-UHFFFAOYSA-N 4-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]benzonitrile Chemical compound CC1=CC=NC=C1C1=CSC(C=2C=CC(=CC=2)C#N)=N1 LNJAEKBOQMMMQB-UHFFFAOYSA-N 0.000 description 3
- YAFJSMQTZSFJOG-UHFFFAOYSA-N 4-cyclopropylpyridine-3-carbonitrile Chemical compound N#CC1=CN=CC=C1C1CC1 YAFJSMQTZSFJOG-UHFFFAOYSA-N 0.000 description 3
- XLAPHZHNODDMDD-UHFFFAOYSA-N 4-methylpyridine-3-carbonitrile Chemical compound CC1=CC=NC=C1C#N XLAPHZHNODDMDD-UHFFFAOYSA-N 0.000 description 3
- ACKSTMUOXBUQHJ-UHFFFAOYSA-N 4-phenylpyridine-3-carbonitrile Chemical compound N#CC1=CN=CC=C1C1=CC=CC=C1 ACKSTMUOXBUQHJ-UHFFFAOYSA-N 0.000 description 3
- CEUQXFVDZRGSRU-UHFFFAOYSA-N 4-propylpyridine-3-carbonitrile Chemical compound CCCC1=CC=NC=C1C#N CEUQXFVDZRGSRU-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 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 3
- 229940122014 Lyase inhibitor Drugs 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- HHEXTKSPOBMCPY-UHFFFAOYSA-N NC=S.C1=CC=NC=C1 Chemical class NC=S.C1=CC=NC=C1 HHEXTKSPOBMCPY-UHFFFAOYSA-N 0.000 description 3
- 229910017974 NH40H Inorganic materials 0.000 description 3
- 239000007832 Na2SO4 Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 230000003321 amplification Effects 0.000 description 3
- 229960003473 androstanolone Drugs 0.000 description 3
- 239000000051 antiandrogen Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- LKXYJYDRLBPHRS-UHFFFAOYSA-N bromocyclopropane Chemical compound BrC1CC1 LKXYJYDRLBPHRS-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 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
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 229960005309 estradiol Drugs 0.000 description 3
- BPCHZEFJOLSOHK-UHFFFAOYSA-N ethyl 2-(4-methylpyridin-3-yl)-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(C=2C(=CC=NC=2)C)=N1 BPCHZEFJOLSOHK-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 125000001207 fluorophenyl group Chemical group 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000001794 hormone therapy Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000007918 intramuscular administration Methods 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229940057995 liquid paraffin Drugs 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 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
- 150000007522 mineralic acids Chemical class 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
- 230000002611 ovarian Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 3
- 229940037129 plain mineralocorticoids for systemic use Drugs 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229960002847 prasterone Drugs 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
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 235000015424 sodium Nutrition 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
- 150000007979 thiazole derivatives Chemical class 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 3
- 239000003981 vehicle Substances 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
- CQPKBZUIRFIQSE-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl) 2-(4-methylpyridin-3-yl)-1,3-thiazole-4-carboxylate Chemical compound CC1=CC=NC=C1C1=NC(C(=O)OC=2C(=C(F)C(F)=C(F)C=2F)F)=CS1 CQPKBZUIRFIQSE-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
- 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
- ORECNKBJIMKZNX-UHFFFAOYSA-N 1,3-thiazol-3-ium;chloride Chemical compound Cl.C1=CSC=N1 ORECNKBJIMKZNX-UHFFFAOYSA-N 0.000 description 2
- HGIBQMWHJDITQK-UHFFFAOYSA-N 1-(4-cyclopropylpyridin-3-yl)ethanone Chemical compound CC(=O)C1=CN=CC=C1C1CC1 HGIBQMWHJDITQK-UHFFFAOYSA-N 0.000 description 2
- FGNXOQIMDXTCQJ-UHFFFAOYSA-N 1-(4-propan-2-ylpyridin-3-yl)ethanone Chemical compound CC(C)C1=CC=NC=C1C(C)=O FGNXOQIMDXTCQJ-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
- 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
- PMWGIVRHUIAIII-UHFFFAOYSA-N 2,2-difluoropropanoic acid Chemical compound CC(F)(F)C(O)=O PMWGIVRHUIAIII-UHFFFAOYSA-N 0.000 description 2
- LSPMHHJCDSFAAY-UHFFFAOYSA-N 2,6-dichloro-4-methylpyridine-3-carbonitrile Chemical compound CC1=CC(Cl)=NC(Cl)=C1C#N LSPMHHJCDSFAAY-UHFFFAOYSA-N 0.000 description 2
- OEVQDTLHJYEGEI-UHFFFAOYSA-N 2,6-dichloro-4-phenylpyridine-3-carbonitrile Chemical compound ClC1=NC(Cl)=CC(C=2C=CC=CC=2)=C1C#N OEVQDTLHJYEGEI-UHFFFAOYSA-N 0.000 description 2
- SUTYTFWFCGRRAK-UHFFFAOYSA-N 2,6-dichloro-4-propylpyridine-3-carbonitrile Chemical compound CCCC1=CC(Cl)=NC(Cl)=C1C#N SUTYTFWFCGRRAK-UHFFFAOYSA-N 0.000 description 2
- XBYPZLKTFKMYFU-UHFFFAOYSA-N 2-(2-fluorophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C(=CC=CC=2)F)=N1 XBYPZLKTFKMYFU-UHFFFAOYSA-N 0.000 description 2
- NTJGYAXVIKGRMZ-UHFFFAOYSA-N 2-(2-methoxyphenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound COC1=CC=CC=C1C1=NC(C=2C(=CC=NC=2)C)=CS1 NTJGYAXVIKGRMZ-UHFFFAOYSA-N 0.000 description 2
- UMQUIRYNOVNYPA-UHFFFAOYSA-N 2-(4-chlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=CC=C(Cl)C=C1 UMQUIRYNOVNYPA-UHFFFAOYSA-N 0.000 description 2
- WZVVGGDHENXADU-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-(3-nitrophenyl)-1,3-thiazole Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C2CC2)=C1 WZVVGGDHENXADU-UHFFFAOYSA-N 0.000 description 2
- UXVHYXRQTDLYDA-UHFFFAOYSA-N 2-(4-methylpyridin-3-yl)-1,3-thiazole-4-carboxylic acid Chemical compound CC1=CC=NC=C1C1=NC(C(O)=O)=CS1 UXVHYXRQTDLYDA-UHFFFAOYSA-N 0.000 description 2
- YBFMHGWOBFMBPM-UHFFFAOYSA-N 2-(4-methylpyridin-3-yl)-4-(4-nitrophenyl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)[N+]([O-])=O)=CS1 YBFMHGWOBFMBPM-UHFFFAOYSA-N 0.000 description 2
- XXMFKGCXKLOXIS-UHFFFAOYSA-N 2-(4-methylpyridin-3-yl)-4-pyridin-2-yl-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2N=CC=CC=2)=CS1 XXMFKGCXKLOXIS-UHFFFAOYSA-N 0.000 description 2
- KHWCCUNYDRVVCI-UHFFFAOYSA-N 2-(4-methylpyridin-3-yl)-4-pyridin-4-yl-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=CN=CC=2)=CS1 KHWCCUNYDRVVCI-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- YEUYKZLMAGACBX-UHFFFAOYSA-N 2-[3-(dimethylamino)-1-methoxyprop-2-enylidene]propanedinitrile Chemical compound N#CC(C#N)=C(OC)C=CN(C)C YEUYKZLMAGACBX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KEFJLCGVTHRGAH-UHFFFAOYSA-N 2-acetyl-5-methylfuran Chemical compound CC(=O)C1=CC=C(C)O1 KEFJLCGVTHRGAH-UHFFFAOYSA-N 0.000 description 2
- TWJPAIWNJRAWKH-UHFFFAOYSA-N 2-bromo-1-(5-methylfuran-2-yl)ethanone Chemical compound CC1=CC=C(C(=O)CBr)O1 TWJPAIWNJRAWKH-UHFFFAOYSA-N 0.000 description 2
- ADLIDZNESKOPIP-UHFFFAOYSA-N 2-bromo-1-cyclohexylethanone Chemical compound BrCC(=O)C1CCCCC1 ADLIDZNESKOPIP-UHFFFAOYSA-N 0.000 description 2
- BYKVUGZUYJUSKD-UHFFFAOYSA-N 2-bromo-1-pyridin-2-ylethanone;hydron;bromide Chemical compound [Br-].BrCC(=O)C1=CC=CC=[NH+]1 BYKVUGZUYJUSKD-UHFFFAOYSA-N 0.000 description 2
- RGALBQILADNMKA-UHFFFAOYSA-N 2-bromo-1-pyridin-4-ylethanone;hydron;bromide Chemical compound Br.BrCC(=O)C1=CC=NC=C1 RGALBQILADNMKA-UHFFFAOYSA-N 0.000 description 2
- JFNPFFAEYZRVJS-UHFFFAOYSA-N 2-bromocycloheptan-1-one Chemical compound BrC1CCCCCC1=O JFNPFFAEYZRVJS-UHFFFAOYSA-N 0.000 description 2
- UMHLFUUYOIVVTK-UHFFFAOYSA-N 2-chloro-1-(4-cyclopropylpyridin-3-yl)ethanone Chemical compound ClCC(=O)C1=CN=CC=C1C1CC1 UMHLFUUYOIVVTK-UHFFFAOYSA-N 0.000 description 2
- SBFTXNYSNGIKCZ-UHFFFAOYSA-N 2-chloro-1-(4-ethylpyridin-3-yl)ethanone Chemical compound CCC1=CC=NC=C1C(=O)CCl SBFTXNYSNGIKCZ-UHFFFAOYSA-N 0.000 description 2
- VCGNFSYALIAYCN-UHFFFAOYSA-N 2-chloro-1-(4-propylpyridin-3-yl)ethanone Chemical compound CCCC1=CC=NC=C1C(=O)CCl VCGNFSYALIAYCN-UHFFFAOYSA-N 0.000 description 2
- MOKUXMQJIYHZCA-UHFFFAOYSA-N 2-chloro-4-methoxypyridine-3-carbonitrile Chemical compound COC1=CC=NC(Cl)=C1C#N MOKUXMQJIYHZCA-UHFFFAOYSA-N 0.000 description 2
- RKCOTKNKKXMGTC-UHFFFAOYSA-N 2-hydroxy-6-oxo-4-phenyl-1h-pyridine-3-carbonitrile Chemical compound N#CC1=C(O)NC(=O)C=C1C1=CC=CC=C1 RKCOTKNKKXMGTC-UHFFFAOYSA-N 0.000 description 2
- ARURRQAKUSJOTF-UHFFFAOYSA-N 2-hydroxy-6-oxo-4-propyl-1h-pyridine-3-carbonitrile Chemical compound CCCC1=CC(O)=NC(O)=C1C#N ARURRQAKUSJOTF-UHFFFAOYSA-N 0.000 description 2
- ZUKTUEOOOXEFML-UHFFFAOYSA-N 2-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2C(=O)C(OC)CCC2=C1 ZUKTUEOOOXEFML-UHFFFAOYSA-N 0.000 description 2
- VRGCYEIGVVTZCC-UHFFFAOYSA-N 3,4,5,6-tetrachlorocyclohexa-3,5-diene-1,2-dione Chemical compound ClC1=C(Cl)C(=O)C(=O)C(Cl)=C1Cl VRGCYEIGVVTZCC-UHFFFAOYSA-N 0.000 description 2
- LMHRZHQIWHLQCY-UHFFFAOYSA-N 3-bromobicyclo[3.2.1]octan-4-one Chemical compound O=C1C(Br)CC2CCC1C2 LMHRZHQIWHLQCY-UHFFFAOYSA-N 0.000 description 2
- DXPFDIGYGOZMLY-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C(=CC(Cl)=CC=2)Cl)=CS1 DXPFDIGYGOZMLY-UHFFFAOYSA-N 0.000 description 2
- VGHZZTBIOMCPGN-UHFFFAOYSA-N 4-(4-fluorophenyl)pyridine-3-carbothioamide Chemical compound NC(=S)C1=CN=CC=C1C1=CC=C(F)C=C1 VGHZZTBIOMCPGN-UHFFFAOYSA-N 0.000 description 2
- ZRFNBJCQOMUAGF-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-2-naphthalen-2-yl-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C=C3C=CC=CC3=CC=2)=N1 ZRFNBJCQOMUAGF-UHFFFAOYSA-N 0.000 description 2
- LRWWQMZAJAKZPJ-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-n-(2-morpholin-4-ylethyl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(NCCN2CCOCC2)=N1 LRWWQMZAJAKZPJ-UHFFFAOYSA-N 0.000 description 2
- LXTMKMGVIAHOKL-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-n-phenyl-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(NC=2C=CC=CC=2)=N1 LXTMKMGVIAHOKL-UHFFFAOYSA-N 0.000 description 2
- KUDBKVSSESJRIM-UHFFFAOYSA-N 4-(5-chlorothiophen-2-yl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2SC(Cl)=CC=2)=CS1 KUDBKVSSESJRIM-UHFFFAOYSA-N 0.000 description 2
- MHKOCBDQVNYAOH-UHFFFAOYSA-N 4-[2-(4-ethylpyridin-3-yl)-1,3-thiazol-4-yl]benzonitrile Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)C#N)=CS1 MHKOCBDQVNYAOH-UHFFFAOYSA-N 0.000 description 2
- NTTHHLFUXHPJEZ-UHFFFAOYSA-N 4-[2-[4-(chloromethyl)pyridin-3-yl]-1,3-thiazol-4-yl]benzonitrile Chemical compound ClCC1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)C#N)=CS1 NTTHHLFUXHPJEZ-UHFFFAOYSA-N 0.000 description 2
- 150000003928 4-aminopyridines Chemical class 0.000 description 2
- SWPYPSDYLXDXQA-UHFFFAOYSA-N 4-cyclohexyl-5-methyl-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC=1SC(C=2C(=CC=NC=2)C)=NC=1C1CCCCC1 SWPYPSDYLXDXQA-UHFFFAOYSA-N 0.000 description 2
- JQZRNJVHXAYOHD-UHFFFAOYSA-N 4-cyclopentylpyridine-3-carbonitrile Chemical compound N#CC1=CN=CC=C1C1CCCC1 JQZRNJVHXAYOHD-UHFFFAOYSA-N 0.000 description 2
- JATKSITUZIZUIY-UHFFFAOYSA-N 4-cyclopentylpyridine-3-carbothioamide Chemical compound NC(=S)C1=CN=CC=C1C1CCCC1 JATKSITUZIZUIY-UHFFFAOYSA-N 0.000 description 2
- OJVXIEGAUZGHDR-UHFFFAOYSA-N 4-ethylpyridine-3-carbonitrile Chemical compound CCC1=CC=NC=C1C#N OJVXIEGAUZGHDR-UHFFFAOYSA-N 0.000 description 2
- MYBUEEHHWNKPCR-UHFFFAOYSA-N 4-ethylpyridine-3-carbothioamide Chemical compound CCC1=CC=NC=C1C(N)=S MYBUEEHHWNKPCR-UHFFFAOYSA-N 0.000 description 2
- ILLQTDYFFYWYAQ-UHFFFAOYSA-N 4-methoxypyridine-3-carbothioamide Chemical compound COC1=CC=NC=C1C(N)=S ILLQTDYFFYWYAQ-UHFFFAOYSA-N 0.000 description 2
- LYBQVKYXTCUFDE-UHFFFAOYSA-N 4-phenylmethoxy-2-pyridin-3-yl-1,3-thiazole Chemical compound C=1C=CC=CC=1COC(N=1)=CSC=1C1=CC=CN=C1 LYBQVKYXTCUFDE-UHFFFAOYSA-N 0.000 description 2
- YMZNVVBWHSEHHY-UHFFFAOYSA-N 4-phenylpyridine-3-carbothioamide Chemical compound NC(=S)C1=CN=CC=C1C1=CC=CC=C1 YMZNVVBWHSEHHY-UHFFFAOYSA-N 0.000 description 2
- YBUZLQQCTZSTKW-UHFFFAOYSA-N 4-propan-2-ylpyridine-3-carbothioamide Chemical compound CC(C)C1=CC=NC=C1C(N)=S YBUZLQQCTZSTKW-UHFFFAOYSA-N 0.000 description 2
- HPFBXNWLJXDGIY-UHFFFAOYSA-N 4-propylpyridine-3-carbothioamide Chemical compound CCCC1=CC=NC=C1C(N)=S HPFBXNWLJXDGIY-UHFFFAOYSA-N 0.000 description 2
- RZKQYJBPWHFSAT-UHFFFAOYSA-N 4-pyridin-3-yl-1,3-thiazole Chemical class S1C=NC(C=2C=NC=CC=2)=C1 RZKQYJBPWHFSAT-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
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 102000014654 Aromatase Human genes 0.000 description 2
- 108010078554 Aromatase Proteins 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 208000008448 Congenital adrenal hyperplasia Diseases 0.000 description 2
- 208000016998 Conn syndrome Diseases 0.000 description 2
- 229940124766 Cyp17 inhibitor Drugs 0.000 description 2
- 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 2
- 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 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 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
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 206010072079 Glucocorticoid deficiency Diseases 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 235000019502 Orange oil Nutrition 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
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-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
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 102100028255 Renin Human genes 0.000 description 2
- 108090000783 Renin Proteins 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
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- QYJQQIRVVLXXSR-UHFFFAOYSA-N [2-(4-methylpyridin-3-yl)-1,3-thiazol-4-yl]-piperidin-1-ylmethanone Chemical compound CC1=CC=NC=C1C1=NC(C(=O)N2CCCCC2)=CS1 QYJQQIRVVLXXSR-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
- 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
- 125000003158 alcohol group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 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
- 238000010171 animal model Methods 0.000 description 2
- 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 2
- 239000003886 aromatase inhibitor Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 210000000481 breast Anatomy 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000010261 cell growth Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 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
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 2
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- IEXIPYCHASVPFD-UHFFFAOYSA-L disodium;7-hydroxynaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=CC(O)=CC=C21 IEXIPYCHASVPFD-UHFFFAOYSA-L 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003792 electrolyte Substances 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
- 229960003399 estrone Drugs 0.000 description 2
- 238000000605 extraction Methods 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
- 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
- 125000005283 haloketone group Chemical group 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000033444 hydroxylation Effects 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
- 239000012535 impurity Substances 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 238000005040 ion trap Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- NPDZTCFGRSYTPF-UHFFFAOYSA-N isoquinoline-4-carbonitrile Chemical compound C1=CC=C2C(C#N)=CN=CC2=C1 NPDZTCFGRSYTPF-UHFFFAOYSA-N 0.000 description 2
- SUWLHYGPNPIKPI-UHFFFAOYSA-N isoquinoline-4-carbothioamide Chemical compound C1=CC=C2C(C(=S)N)=CN=CC2=C1 SUWLHYGPNPIKPI-UHFFFAOYSA-N 0.000 description 2
- 229960004125 ketoconazole Drugs 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
- 230000000670 limiting effect Effects 0.000 description 2
- 239000006193 liquid solution Substances 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 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
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 2
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 2
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 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
- 239000000155 melt Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- KRMIVUWROZJMMA-UHFFFAOYSA-N n-(2-fluorophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(NC=2C(=CC=CC=2)F)=N1 KRMIVUWROZJMMA-UHFFFAOYSA-N 0.000 description 2
- BJDYOFXQGVDWDE-UHFFFAOYSA-N n-(4-chlorophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(NC=2C=CC(Cl)=CC=2)=N1 BJDYOFXQGVDWDE-UHFFFAOYSA-N 0.000 description 2
- UCGWMXSXAVBOEW-UHFFFAOYSA-N n-(4-fluorophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(NC=2C=CC(F)=CC=2)=N1 UCGWMXSXAVBOEW-UHFFFAOYSA-N 0.000 description 2
- RCEJVAWDWAEIAH-UHFFFAOYSA-N n-(4-methoxyphenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound C1=CC(OC)=CC=C1NC1=NC(C=2C(=CC=NC=2)C)=CS1 RCEJVAWDWAEIAH-UHFFFAOYSA-N 0.000 description 2
- DVHKTHQWCYVFIU-UHFFFAOYSA-N n-methyl-4-(4-methylpyridin-3-yl)-n-phenyl-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1N(C)C(SC=1)=NC=1C1=CN=CC=C1C DVHKTHQWCYVFIU-UHFFFAOYSA-N 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
- 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
- 239000010502 orange oil Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- OEQHTXYEGBYGSD-UHFFFAOYSA-N phenyl 3-acetyl-4-ethyl-4h-pyridine-1-carboxylate Chemical compound C1=C(C(C)=O)C(CC)C=CN1C(=O)OC1=CC=CC=C1 OEQHTXYEGBYGSD-UHFFFAOYSA-N 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
- 239000002798 polar solvent Substances 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
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- 208000013846 primary aldosteronism Diseases 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 102000004169 proteins and genes Human genes 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
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
- JBSAUEMFOKUWTP-UHFFFAOYSA-N quinoline-4-carbonitrile Natural products C1=CC=C2C(C#N)=CC=NC2=C1 JBSAUEMFOKUWTP-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
- 238000002821 scintillation proximity assay Methods 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 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
- 239000000600 sorbitol Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000000758 substrate Substances 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
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-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
- 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
- 238000010792 warming Methods 0.000 description 2
- 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
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N (R)-alpha-Tocopherol Natural products OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HPARLNRMYDSBNO-UHFFFAOYSA-N 1,4-benzodioxine Chemical compound C1=CC=C2OC=COC2=C1 HPARLNRMYDSBNO-UHFFFAOYSA-N 0.000 description 1
- PQWGFUFROKIJBO-UHFFFAOYSA-N 1-(3-chlorophenyl)propan-1-one Chemical compound CCC(=O)C1=CC=CC(Cl)=C1 PQWGFUFROKIJBO-UHFFFAOYSA-N 0.000 description 1
- VOMWRXLBUSAIKU-UHFFFAOYSA-N 1-(4-bromophenyl)-3-chloropropan-2-one Chemical compound ClCC(=O)CC1=CC=C(Br)C=C1 VOMWRXLBUSAIKU-UHFFFAOYSA-N 0.000 description 1
- DJNIFZYQFLFGDT-UHFFFAOYSA-N 1-(4-phenoxyphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OC1=CC=CC=C1 DJNIFZYQFLFGDT-UHFFFAOYSA-N 0.000 description 1
- DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 description 1
- MUUHHNKHZXTMTO-UHFFFAOYSA-N 1-[2,4-bis(trifluoromethyl)phenyl]-2-bromoethanone Chemical compound FC(F)(F)C1=CC=C(C(=O)CBr)C(C(F)(F)F)=C1 MUUHHNKHZXTMTO-UHFFFAOYSA-N 0.000 description 1
- MHLYNSLYUWMONA-UHFFFAOYSA-N 1-[2,4-bis(trifluoromethyl)phenyl]ethanone Chemical compound CC(=O)C1=CC=C(C(F)(F)F)C=C1C(F)(F)F MHLYNSLYUWMONA-UHFFFAOYSA-N 0.000 description 1
- NPGUSEJJJVVVME-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=C(Cl)C=C1 NPGUSEJJJVVVME-UHFFFAOYSA-N 0.000 description 1
- PZQTYPIGIYIUHM-UHFFFAOYSA-N 1-[4-[[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]amino]phenyl]ethanone Chemical compound CC(=O)c1ccc(Nc2nc(cs2)-c2cnccc2C)cc1 PZQTYPIGIYIUHM-UHFFFAOYSA-N 0.000 description 1
- BVWOIDPXXWNJBA-UHFFFAOYSA-N 1-chloro-3-(3,4-dichlorophenyl)propan-2-one Chemical compound ClCC(=O)CC1=CC=C(Cl)C(Cl)=C1 BVWOIDPXXWNJBA-UHFFFAOYSA-N 0.000 description 1
- SHMQUTZAYYIMLM-UHFFFAOYSA-N 1-chloro-3-(3-chlorophenyl)propan-2-one Chemical compound ClCC(=O)CC1=CC=CC(Cl)=C1 SHMQUTZAYYIMLM-UHFFFAOYSA-N 0.000 description 1
- RTQAGCNCNZVXFO-UHFFFAOYSA-N 1-chloro-3-(3-methylphenyl)propan-2-one Chemical compound CC1=CC=CC(CC(=O)CCl)=C1 RTQAGCNCNZVXFO-UHFFFAOYSA-N 0.000 description 1
- BIKLXXNVHAWXGY-UHFFFAOYSA-N 1-chloro-3-(3-nitrophenyl)propan-2-one Chemical compound [O-][N+](=O)C1=CC=CC(CC(=O)CCl)=C1 BIKLXXNVHAWXGY-UHFFFAOYSA-N 0.000 description 1
- JFXDUAWJIMUJQN-UHFFFAOYSA-N 1-chloro-3-(4-fluorophenyl)propan-2-one Chemical compound FC1=CC=C(CC(=O)CCl)C=C1 JFXDUAWJIMUJQN-UHFFFAOYSA-N 0.000 description 1
- FKYIKCMAJJDPQM-UHFFFAOYSA-N 1-chloro-3-(4-methylphenyl)propan-2-one Chemical compound CC1=CC=C(CC(=O)CCl)C=C1 FKYIKCMAJJDPQM-UHFFFAOYSA-N 0.000 description 1
- RMPAGSFYXVSYTN-UHFFFAOYSA-N 1-cycloheptylethanone Chemical compound CC(=O)C1CCCCCC1 RMPAGSFYXVSYTN-UHFFFAOYSA-N 0.000 description 1
- RIFKADJTWUGDOV-UHFFFAOYSA-N 1-cyclohexylethanone Chemical compound CC(=O)C1CCCCC1 RIFKADJTWUGDOV-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
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 1
- BSNCOPOPGMQUNL-UHFFFAOYSA-N 1-hydroxytetrazole Chemical compound ON1C=NN=N1 BSNCOPOPGMQUNL-UHFFFAOYSA-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
- GFPKJHASUZCPRI-UHFFFAOYSA-N 1-pyridin-3-ylethanone;hydrochloride Chemical compound Cl.CC(=O)C1=CC=CN=C1 GFPKJHASUZCPRI-UHFFFAOYSA-N 0.000 description 1
- WMQUKDQWMMOHSA-UHFFFAOYSA-N 1-pyridin-4-ylethanone Chemical compound CC(=O)C1=CC=NC=C1 WMQUKDQWMMOHSA-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
- XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 1
- MUECGDALHJLKPK-UHFFFAOYSA-N 2,4-bis(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C(=CC=NC=2)C)=N1 MUECGDALHJLKPK-UHFFFAOYSA-N 0.000 description 1
- ITJUUTBLPGKSOG-UHFFFAOYSA-N 2,4-dipyridin-3-yl-1,3-thiazole Chemical compound C=1SC(C=2C=NC=CC=2)=NC=1C1=CC=CN=C1 ITJUUTBLPGKSOG-UHFFFAOYSA-N 0.000 description 1
- SPNCVQGYKGNOLM-UHFFFAOYSA-N 2-(2,3-dichlorophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C(=C(Cl)C=CC=2)Cl)=N1 SPNCVQGYKGNOLM-UHFFFAOYSA-N 0.000 description 1
- YCAQVESCIBILNT-UHFFFAOYSA-N 2-(2,3-dihydro-1-benzofuran-5-yl)-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C=C3CCOC3=CC=2)=N1 YCAQVESCIBILNT-UHFFFAOYSA-N 0.000 description 1
- GXUZGVDRLSQWRY-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C(=CC(Cl)=CC=2)Cl)=N1 GXUZGVDRLSQWRY-UHFFFAOYSA-N 0.000 description 1
- NAPMYDMTNKWHHT-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C(=CC=CC=2)Cl)=N1 NAPMYDMTNKWHHT-UHFFFAOYSA-N 0.000 description 1
- MLFFBJDPPXXZMU-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-ethyl-1-(4-propan-2-ylphenyl)imidazole-4-carboxylic acid Chemical compound CCc1c(nc(-c2ccccc2Cl)n1-c1ccc(cc1)C(C)C)C(O)=O MLFFBJDPPXXZMU-UHFFFAOYSA-N 0.000 description 1
- IMCSEQAXIGWUDH-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C=C(Cl)C(F)=CC=2)=N1 IMCSEQAXIGWUDH-UHFFFAOYSA-N 0.000 description 1
- JYSPSVDCQKYXOS-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-pyridin-3-yl-1,3-thiazole Chemical compound C1=C(Cl)C(F)=CC=C1C1=NC(C=2C=NC=CC=2)=CS1 JYSPSVDCQKYXOS-UHFFFAOYSA-N 0.000 description 1
- HUSCVGUBUWYFSR-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C=C(Cl)C=CC=2)=N1 HUSCVGUBUWYFSR-UHFFFAOYSA-N 0.000 description 1
- WFPMUFXQDKMVCO-UHFFFAOYSA-N 2-(3-chlorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Cl)=C1 WFPMUFXQDKMVCO-UHFFFAOYSA-N 0.000 description 1
- WEDCXKJZMXKITN-UHFFFAOYSA-N 2-(3-fluoro-4-methylphenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound C1=C(F)C(C)=CC=C1C1=NC(C=2C(=CC=NC=2)C)=CS1 WEDCXKJZMXKITN-UHFFFAOYSA-N 0.000 description 1
- LJNCIPVBIMUAQG-UHFFFAOYSA-N 2-(3-fluorophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C=C(F)C=CC=2)=N1 LJNCIPVBIMUAQG-UHFFFAOYSA-N 0.000 description 1
- HHDBFCJCYBEBMW-UHFFFAOYSA-N 2-(3-methoxyphenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound COC1=CC=CC(C=2SC=C(N=2)C=2C(=CC=NC=2)C)=C1 HHDBFCJCYBEBMW-UHFFFAOYSA-N 0.000 description 1
- WTYLLDWMSKFKCW-UHFFFAOYSA-N 2-(3-nitrophenyl)-4-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=CSC(C=2C=C(C=CC=2)[N+]([O-])=O)=N1 WTYLLDWMSKFKCW-UHFFFAOYSA-N 0.000 description 1
- VYLYHXRQVMCCRM-UHFFFAOYSA-N 2-(4-butylpyridin-3-yl)-4-(4-chlorophenyl)-1,3-thiazole Chemical compound CCCCC1=CC=NC=C1C1=NC(C=2C=CC(Cl)=CC=2)=CS1 VYLYHXRQVMCCRM-UHFFFAOYSA-N 0.000 description 1
- PKJQEPSCDYDBFK-UHFFFAOYSA-N 2-(4-butylpyridin-3-yl)-4-(4-chlorophenyl)-5-propyl-1,3-thiazole Chemical compound CCCCC1=CC=NC=C1C1=NC(C=2C=CC(Cl)=CC=2)=C(CCC)S1 PKJQEPSCDYDBFK-UHFFFAOYSA-N 0.000 description 1
- KHZWBWFKMIPKJX-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C=CC(Cl)=CC=2)=N1 KHZWBWFKMIPKJX-UHFFFAOYSA-N 0.000 description 1
- YAVDQDXOQABEKO-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=CSC(C=2C=CC(Cl)=CC=2)=N1 YAVDQDXOQABEKO-UHFFFAOYSA-N 0.000 description 1
- JLOGZXLJOMSEMI-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[4-(2-methylpropyl)pyridin-3-yl]-1,3-thiazole Chemical compound CC(C)CC1=CC=NC=C1C1=CN=C(C=2C=CC(Cl)=CC=2)S1 JLOGZXLJOMSEMI-UHFFFAOYSA-N 0.000 description 1
- FEPLQMXMSADGSO-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-ethyl-4-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=C(CC)SC(C=2C=CC(Cl)=CC=2)=N1 FEPLQMXMSADGSO-UHFFFAOYSA-N 0.000 description 1
- VSOHBXIKYTYEPK-UHFFFAOYSA-N 2-(4-cyclopentylpyridin-3-yl)-4-(2,4-dichlorophenyl)-1,3-thiazole Chemical compound ClC1=CC(Cl)=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CCCC2)=N1 VSOHBXIKYTYEPK-UHFFFAOYSA-N 0.000 description 1
- YNBYSDJKBHZAQF-UHFFFAOYSA-N 2-(4-cyclopentylpyridin-3-yl)-4-(2,4-dimethylphenyl)-1,3-thiazole Chemical compound CC1=CC(C)=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CCCC2)=N1 YNBYSDJKBHZAQF-UHFFFAOYSA-N 0.000 description 1
- KOUQFTFROZEDMT-UHFFFAOYSA-N 2-(4-cyclopentylpyridin-3-yl)-4-(2,5-dimethoxyphenyl)-1,3-thiazole Chemical compound COC1=CC=C(OC)C(C=2N=C(SC=2)C=2C(=CC=NC=2)C2CCCC2)=C1 KOUQFTFROZEDMT-UHFFFAOYSA-N 0.000 description 1
- JGRPMONNHJMCTR-UHFFFAOYSA-N 2-(4-cyclopentylpyridin-3-yl)-4-(2-methoxyphenyl)-1,3-thiazole Chemical compound COC1=CC=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CCCC2)=N1 JGRPMONNHJMCTR-UHFFFAOYSA-N 0.000 description 1
- BIFHWZRHTUEOJK-UHFFFAOYSA-N 2-(4-cyclopentylpyridin-3-yl)-4-(2-nitrophenyl)-1,3-thiazole Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CCCC2)=N1 BIFHWZRHTUEOJK-UHFFFAOYSA-N 0.000 description 1
- IFINDTWXLMXKMF-UHFFFAOYSA-N 2-(4-cyclopentylpyridin-3-yl)-4-(3,4-dichlorophenyl)-1,3-thiazole Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CCCC2)=N1 IFINDTWXLMXKMF-UHFFFAOYSA-N 0.000 description 1
- MVWSQJMIVWVZGN-UHFFFAOYSA-N 2-(4-cyclopentylpyridin-3-yl)-4-(3-fluorophenyl)-1,3-thiazole Chemical compound FC1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C2CCCC2)=C1 MVWSQJMIVWVZGN-UHFFFAOYSA-N 0.000 description 1
- PMOYJYOXLPBKBZ-UHFFFAOYSA-N 2-(4-cyclopentylpyridin-3-yl)-4-(3-nitrophenyl)-1,3-thiazole Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C2CCCC2)=C1 PMOYJYOXLPBKBZ-UHFFFAOYSA-N 0.000 description 1
- YDWXDIQKGNQXRM-UHFFFAOYSA-N 2-(4-cyclopentylpyridin-3-yl)-4-(4-fluorophenyl)-1,3-thiazole Chemical compound C1=CC(F)=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CCCC2)=N1 YDWXDIQKGNQXRM-UHFFFAOYSA-N 0.000 description 1
- GOLCKVOKGPIKMX-UHFFFAOYSA-N 2-(4-cyclopentylpyridin-3-yl)-4-(4-methoxyphenyl)-1,3-thiazole Chemical compound C1=CC(OC)=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CCCC2)=N1 GOLCKVOKGPIKMX-UHFFFAOYSA-N 0.000 description 1
- XWROAHMHKBQJRM-UHFFFAOYSA-N 2-(4-cyclopentylpyridin-3-yl)-4-(4-methoxyphenyl)-5-methyl-1,3-thiazole Chemical compound COc1ccc(cc1)-c1nc(sc1C)-c1cnccc1C1CCCC1 XWROAHMHKBQJRM-UHFFFAOYSA-N 0.000 description 1
- LKUFAGDEHDPGBT-UHFFFAOYSA-N 2-(4-cyclopentylpyridin-3-yl)-4-(4-methylphenyl)-1,3-thiazole Chemical compound C1=CC(C)=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CCCC2)=N1 LKUFAGDEHDPGBT-UHFFFAOYSA-N 0.000 description 1
- UHCXATJCPIEQHN-UHFFFAOYSA-N 2-(4-cyclopentylpyridin-3-yl)-4-(4-nitrophenyl)-1,3-thiazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CCCC2)=N1 UHCXATJCPIEQHN-UHFFFAOYSA-N 0.000 description 1
- RPADFPJUXYDPDN-UHFFFAOYSA-N 2-(4-cyclopentylpyridin-3-yl)-4-(4-phenylphenyl)-1,3-thiazole Chemical compound C1CCCC1C1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=CS1 RPADFPJUXYDPDN-UHFFFAOYSA-N 0.000 description 1
- PVTBQUFQFYJYMV-UHFFFAOYSA-N 2-(4-cyclopentylpyridin-3-yl)-4-[4-(difluoromethoxy)phenyl]-1,3-thiazole Chemical compound C1(CCCC1)C1=C(C=NC=C1)C=1SC=C(N1)C1=CC=C(OC(F)F)C=C1 PVTBQUFQFYJYMV-UHFFFAOYSA-N 0.000 description 1
- YCZZBMDFMVAIOG-UHFFFAOYSA-N 2-(4-cyclopentylpyridin-3-yl)-4-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CCCC2)=N1 YCZZBMDFMVAIOG-UHFFFAOYSA-N 0.000 description 1
- DGSCJOQDEJKPKF-UHFFFAOYSA-N 2-(4-cyclopentylpyridin-3-yl)-4-naphthalen-2-yl-1,3-thiazole Chemical compound C1CCCC1C1=CC=NC=C1C1=NC(C=2C=C3C=CC=CC3=CC=2)=CS1 DGSCJOQDEJKPKF-UHFFFAOYSA-N 0.000 description 1
- UIYDFEBMVNLCST-UHFFFAOYSA-N 2-(4-cyclopentylpyridin-3-yl)-4-phenyl-1,3-thiazole Chemical compound C1CCCC1C1=CC=NC=C1C1=NC(C=2C=CC=CC=2)=CS1 UIYDFEBMVNLCST-UHFFFAOYSA-N 0.000 description 1
- IZRMMWXREHWTFO-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-(2,4-dimethylphenyl)-1,3-thiazole Chemical compound CC1=CC(C)=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CC2)=N1 IZRMMWXREHWTFO-UHFFFAOYSA-N 0.000 description 1
- WUDPVZZRVWMPGO-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-(2,5-dimethoxyphenyl)-1,3-thiazole Chemical compound COC1=CC=C(OC)C(C=2N=C(SC=2)C=2C(=CC=NC=2)C2CC2)=C1 WUDPVZZRVWMPGO-UHFFFAOYSA-N 0.000 description 1
- RYBUOVLWUDIOJC-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-(2-fluorophenyl)-1,3-thiazole Chemical compound FC1=CC=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CC2)=N1 RYBUOVLWUDIOJC-UHFFFAOYSA-N 0.000 description 1
- ZEPJGNVKOLQTND-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-(2-methoxyphenyl)-1,3-thiazole Chemical compound COC1=CC=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CC2)=N1 ZEPJGNVKOLQTND-UHFFFAOYSA-N 0.000 description 1
- RQJUADYDDNGMEE-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-(2-nitrophenyl)-1,3-thiazole Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CC2)=N1 RQJUADYDDNGMEE-UHFFFAOYSA-N 0.000 description 1
- IYYMPVVJYYUZEH-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-(3,4-dichlorophenyl)-1,3-thiazole Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CC2)=N1 IYYMPVVJYYUZEH-UHFFFAOYSA-N 0.000 description 1
- QKMUJHDWLSUWIT-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-(3-fluorophenyl)-1,3-thiazole Chemical compound FC1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C2CC2)=C1 QKMUJHDWLSUWIT-UHFFFAOYSA-N 0.000 description 1
- PCZRKPIGIOAXAP-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-(4-fluorophenyl)-1,3-thiazole Chemical compound C1=CC(F)=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CC2)=N1 PCZRKPIGIOAXAP-UHFFFAOYSA-N 0.000 description 1
- YCCVULCTNSLLFV-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-(4-methoxyphenyl)-1,3-thiazole Chemical compound C1=CC(OC)=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CC2)=N1 YCCVULCTNSLLFV-UHFFFAOYSA-N 0.000 description 1
- CLTFBEOQNIXZJG-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-(4-methoxyphenyl)-5-methyl-1,3-thiazole Chemical compound COc1ccc(cc1)-c1nc(sc1C)-c1cnccc1C1CC1 CLTFBEOQNIXZJG-UHFFFAOYSA-N 0.000 description 1
- HANJWYKIPSSDSK-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-(4-methylphenyl)-1,3-thiazole Chemical compound C1=CC(C)=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CC2)=N1 HANJWYKIPSSDSK-UHFFFAOYSA-N 0.000 description 1
- JDBSIMRBHXJHIM-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C(=CC=NC=2)C2CC2)=N1 JDBSIMRBHXJHIM-UHFFFAOYSA-N 0.000 description 1
- WTDOTXWRGNTCLM-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-(4-nitrophenyl)-1,3-thiazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CC2)=N1 WTDOTXWRGNTCLM-UHFFFAOYSA-N 0.000 description 1
- KDRYPFGVMZDNFU-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-(4-phenylphenyl)-1,3-thiazole Chemical compound C1CC1C1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=CS1 KDRYPFGVMZDNFU-UHFFFAOYSA-N 0.000 description 1
- SWSIKZFCOWSZSZ-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CC2)=N1 SWSIKZFCOWSZSZ-UHFFFAOYSA-N 0.000 description 1
- VKSCANCMYANNIM-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-naphthalen-2-yl-1,3-thiazole Chemical compound C1CC1C1=CC=NC=C1C1=NC(C=2C=C3C=CC=CC3=CC=2)=CS1 VKSCANCMYANNIM-UHFFFAOYSA-N 0.000 description 1
- HDRIVPJPPFGOBD-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-phenyl-1,3-thiazole Chemical compound C1CC1C1=CC=NC=C1C1=NC(C=2C=CC=CC=2)=CS1 HDRIVPJPPFGOBD-UHFFFAOYSA-N 0.000 description 1
- ZLSIRDZOQOQNGT-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-pyridin-2-yl-1,3-thiazole Chemical compound C1CC1C1=CC=NC=C1C1=NC(C=2N=CC=CC=2)=CS1 ZLSIRDZOQOQNGT-UHFFFAOYSA-N 0.000 description 1
- LEUVCLBEMKPFRN-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-pyridin-3-yl-1,3-thiazole Chemical compound C1CC1C1=CC=NC=C1C1=NC(C=2C=NC=CC=2)=CS1 LEUVCLBEMKPFRN-UHFFFAOYSA-N 0.000 description 1
- QFFIRZFSNKNDFT-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-pyridin-4-yl-1,3-thiazole Chemical compound C1CC1C1=CC=NC=C1C1=NC(C=2C=CN=CC=2)=CS1 QFFIRZFSNKNDFT-UHFFFAOYSA-N 0.000 description 1
- JKSWBOWSIOMWJX-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-4-thiophen-3-yl-1,3-thiazole Chemical compound C1CC1C1=CC=NC=C1C1=NC(C2=CSC=C2)=CS1 JKSWBOWSIOMWJX-UHFFFAOYSA-N 0.000 description 1
- OMNXCKOFVBIJMK-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-3-yl)-5-methyl-4-phenyl-1,3-thiazole Chemical compound CC=1SC(C=2C(=CC=NC=2)C2CC2)=NC=1C1=CC=CC=C1 OMNXCKOFVBIJMK-UHFFFAOYSA-N 0.000 description 1
- RJHXXNCKHLVTDI-UHFFFAOYSA-N 2-(4-ethylpyridin-3-yl)-4-(2-fluorophenyl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C(=CC=CC=2)F)=CS1 RJHXXNCKHLVTDI-UHFFFAOYSA-N 0.000 description 1
- BGRUNOBUUDFCCA-UHFFFAOYSA-N 2-(4-ethylpyridin-3-yl)-4-(2-methoxyphenyl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C(=CC=CC=2)OC)=CS1 BGRUNOBUUDFCCA-UHFFFAOYSA-N 0.000 description 1
- LINGMERHWDEAIS-UHFFFAOYSA-N 2-(4-ethylpyridin-3-yl)-4-(2-nitrophenyl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C(=CC=CC=2)[N+]([O-])=O)=CS1 LINGMERHWDEAIS-UHFFFAOYSA-N 0.000 description 1
- GXLIZQZPHOOXJJ-UHFFFAOYSA-N 2-(4-ethylpyridin-3-yl)-4-(3-fluorophenyl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=C(F)C=CC=2)=CS1 GXLIZQZPHOOXJJ-UHFFFAOYSA-N 0.000 description 1
- WNRMDTVTLKTDIO-UHFFFAOYSA-N 2-(4-ethylpyridin-3-yl)-4-(3-nitrophenyl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CS1 WNRMDTVTLKTDIO-UHFFFAOYSA-N 0.000 description 1
- MBTHJJOUVIUCTO-UHFFFAOYSA-N 2-(4-ethylpyridin-3-yl)-4-(4-fluorophenyl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=CC(F)=CC=2)=CS1 MBTHJJOUVIUCTO-UHFFFAOYSA-N 0.000 description 1
- KOCSQXASKQAPPV-UHFFFAOYSA-N 2-(4-ethylpyridin-3-yl)-4-(4-methoxyphenyl)-5-methyl-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=CC(OC)=CC=2)=C(C)S1 KOCSQXASKQAPPV-UHFFFAOYSA-N 0.000 description 1
- IHGFUJHPGCAZNV-UHFFFAOYSA-N 2-(4-ethylpyridin-3-yl)-4-(4-methylphenyl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=CC(C)=CC=2)=CS1 IHGFUJHPGCAZNV-UHFFFAOYSA-N 0.000 description 1
- NJZGSFYROZPROW-UHFFFAOYSA-N 2-(4-ethylpyridin-3-yl)-4-(4-nitrophenyl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)[N+]([O-])=O)=CS1 NJZGSFYROZPROW-UHFFFAOYSA-N 0.000 description 1
- OXKQPQRIDHMDBA-UHFFFAOYSA-N 2-(4-ethylpyridin-3-yl)-4-(4-phenylphenyl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=CS1 OXKQPQRIDHMDBA-UHFFFAOYSA-N 0.000 description 1
- MWKAQKOOFJZSLA-UHFFFAOYSA-N 2-(4-ethylpyridin-3-yl)-4-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)C(F)(F)F)=CS1 MWKAQKOOFJZSLA-UHFFFAOYSA-N 0.000 description 1
- DBMFGYLNOIDZCK-UHFFFAOYSA-N 2-(4-ethylpyridin-3-yl)-4-naphthalen-2-yl-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=C3C=CC=CC3=CC=2)=CS1 DBMFGYLNOIDZCK-UHFFFAOYSA-N 0.000 description 1
- IJXXAZGMFDOXPD-UHFFFAOYSA-N 2-(4-ethylpyridin-3-yl)-4-phenyl-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=CC=CC=2)=CS1 IJXXAZGMFDOXPD-UHFFFAOYSA-N 0.000 description 1
- OOXQUYVHUYXNBG-UHFFFAOYSA-N 2-(4-ethylpyridin-3-yl)-4-pyridin-3-yl-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=NC=CC=2)=CS1 OOXQUYVHUYXNBG-UHFFFAOYSA-N 0.000 description 1
- LXMKGZYIJDBAQI-UHFFFAOYSA-N 2-(4-ethylpyridin-3-yl)-4-thiophen-3-yl-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C2=CSC=C2)=CS1 LXMKGZYIJDBAQI-UHFFFAOYSA-N 0.000 description 1
- OBEAOCSBVATWSP-UHFFFAOYSA-N 2-(4-ethylpyridin-3-yl)-5-methyl-4-[4-(2-methylpropyl)phenyl]-1,3-thiazole Chemical compound CCc1ccncc1-c1nc(c(C)s1)-c1ccc(CC(C)C)cc1 OBEAOCSBVATWSP-UHFFFAOYSA-N 0.000 description 1
- GZDNXCSPTDDOAC-UHFFFAOYSA-N 2-(4-ethylpyridin-3-yl)-5-methyl-4-phenyl-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=CC=CC=2)=C(C)S1 GZDNXCSPTDDOAC-UHFFFAOYSA-N 0.000 description 1
- MGKPFALCNDRSQD-UHFFFAOYSA-N 2-(4-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(F)C=C1 MGKPFALCNDRSQD-UHFFFAOYSA-N 0.000 description 1
- WUUCEXKCEALEPY-UHFFFAOYSA-N 2-(4-methoxy-3-nitrophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound C1=C([N+]([O-])=O)C(OC)=CC=C1C1=NC(C=2C(=CC=NC=2)C)=CS1 WUUCEXKCEALEPY-UHFFFAOYSA-N 0.000 description 1
- UDRKWQMBIPYRTH-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound C1=CC(OC)=CC=C1C1=NC(C=2C(=CC=NC=2)C)=CS1 UDRKWQMBIPYRTH-UHFFFAOYSA-N 0.000 description 1
- FIPJIALIJAYWRQ-UHFFFAOYSA-N 2-(4-methylphenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound C1=CC(C)=CC=C1C1=NC(C=2C(=CC=NC=2)C)=CS1 FIPJIALIJAYWRQ-UHFFFAOYSA-N 0.000 description 1
- OEVHOCQQCTZFFY-UHFFFAOYSA-N 2-(4-methylpyridin-3-yl)-1,3-thiazole-4-carboxamide Chemical class CC1=CC=NC=C1C1=NC(C(N)=O)=CS1 OEVHOCQQCTZFFY-UHFFFAOYSA-N 0.000 description 1
- CQUNVUAYSSSKFG-UHFFFAOYSA-N 2-(4-methylpyridin-3-yl)-4,5,6,7-tetrahydro-1,3-benzothiazole Chemical compound CC1=CC=NC=C1C(S1)=NC2=C1CCCC2 CQUNVUAYSSSKFG-UHFFFAOYSA-N 0.000 description 1
- XNIYJPWQOQFTIJ-UHFFFAOYSA-N 2-(4-methylpyridin-3-yl)-4,5-dihydrobenzo[e][1,3]benzothiazole Chemical compound CC1=CC=NC=C1C(S1)=NC2=C1CCC1=CC=CC=C21 XNIYJPWQOQFTIJ-UHFFFAOYSA-N 0.000 description 1
- UIYNNRXTJMHCAO-UHFFFAOYSA-N 2-(4-methylpyridin-3-yl)-4-(2-nitrophenyl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C(=CC=CC=2)[N+]([O-])=O)=CS1 UIYNNRXTJMHCAO-UHFFFAOYSA-N 0.000 description 1
- XKQXPXKFYSMWCK-UHFFFAOYSA-N 2-(4-methylpyridin-3-yl)-4-(3-nitrophenyl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CS1 XKQXPXKFYSMWCK-UHFFFAOYSA-N 0.000 description 1
- BMCKFICPIJUCCF-UHFFFAOYSA-N 2-(4-methylpyridin-3-yl)-4-(4-phenylphenyl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=CS1 BMCKFICPIJUCCF-UHFFFAOYSA-N 0.000 description 1
- PMNCDFJAWQAPHI-UHFFFAOYSA-N 2-(4-methylpyridin-3-yl)-4-naphthalen-2-yl-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=C3C=CC=CC3=CC=2)=CS1 PMNCDFJAWQAPHI-UHFFFAOYSA-N 0.000 description 1
- RKNXRDWHNKHFDL-UHFFFAOYSA-N 2-(4-methylpyridin-3-yl)-4-phenyl-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=CC=CC=2)=CS1 RKNXRDWHNKHFDL-UHFFFAOYSA-N 0.000 description 1
- NPIDCKSFXVKJNE-UHFFFAOYSA-N 2-(4-methylpyridin-3-yl)-4-phenyl-5,6,7,8-tetrahydro-4h-cyclohepta[d][1,3]thiazole Chemical compound CC1=CC=NC=C1C(S1)=NC2=C1CCCCC2C1=CC=CC=C1 NPIDCKSFXVKJNE-UHFFFAOYSA-N 0.000 description 1
- VUMYBSBBJLRRQB-UHFFFAOYSA-N 2-(4-methylpyridin-3-yl)-4-phenylmethoxy-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(OCC=2C=CC=CC=2)=CS1 VUMYBSBBJLRRQB-UHFFFAOYSA-N 0.000 description 1
- FYUSWXHSLSWYSB-UHFFFAOYSA-N 2-(4-methylpyridin-3-yl)-4-pyridin-3-yl-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=NC=CC=2)=CS1 FYUSWXHSLSWYSB-UHFFFAOYSA-N 0.000 description 1
- LAACYKYVNINKKG-UHFFFAOYSA-N 2-(4-methylpyridin-3-yl)-5,6,7,8-tetrahydro-4h-cyclohepta[d][1,3]thiazole Chemical compound CC1=CC=NC=C1C(S1)=NC2=C1CCCCC2 LAACYKYVNINKKG-UHFFFAOYSA-N 0.000 description 1
- GSIMYXOTHARAFD-UHFFFAOYSA-N 2-(4-methylpyridin-3-yl)-6,7-dihydro-1,3-benzothiazole-4,5-diimine Chemical compound CC1=CC=NC=C1C(S1)=NC2=C1CCC(=N)C2=N GSIMYXOTHARAFD-UHFFFAOYSA-N 0.000 description 1
- HOBLLIATZRPWJT-UHFFFAOYSA-N 2-(4-nitrophenyl)-4-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=CSC(C=2C=CC(=CC=2)[N+]([O-])=O)=N1 HOBLLIATZRPWJT-UHFFFAOYSA-N 0.000 description 1
- RYFLFEZDRIMVQO-UHFFFAOYSA-N 2-(4-phenylpyridin-3-yl)-4-(4-propan-2-ylpyridin-3-yl)-1,3-thiazole Chemical compound CC(C)C1=CC=NC=C1C1=CSC(C=2C(=CC=NC=2)C=2C=CC=CC=2)=N1 RYFLFEZDRIMVQO-UHFFFAOYSA-N 0.000 description 1
- HOCSQNJCRQEBHF-UHFFFAOYSA-N 2-(4-phenylpyridin-3-yl)-4-(4-pyrrolidin-1-ylphenyl)-1,3-thiazole Chemical compound C1CCCN1C1=CC=C(C=2N=C(SC=2)C=2C(=CC=NC=2)C=2C=CC=CC=2)C=C1 HOCSQNJCRQEBHF-UHFFFAOYSA-N 0.000 description 1
- NLCFJFLXSFSSOO-UHFFFAOYSA-N 2-(4-phenylpyridin-3-yl)-4-pyridin-2-yl-1,3-thiazole Chemical compound C=1SC(C=2C(=CC=NC=2)C=2C=CC=CC=2)=NC=1C1=CC=CC=N1 NLCFJFLXSFSSOO-UHFFFAOYSA-N 0.000 description 1
- AFYWKGJBLDYHPJ-UHFFFAOYSA-N 2-(4-phenylpyridin-3-yl)-4-pyridin-3-yl-1,3-thiazole Chemical compound C=1SC(C=2C(=CC=NC=2)C=2C=CC=CC=2)=NC=1C1=CC=CN=C1 AFYWKGJBLDYHPJ-UHFFFAOYSA-N 0.000 description 1
- XVRPXWVGCCHWEO-UHFFFAOYSA-N 2-(4-phenylpyridin-3-yl)-4-pyridin-4-yl-1,3-thiazole Chemical compound C=1SC(C=2C(=CC=NC=2)C=2C=CC=CC=2)=NC=1C1=CC=NC=C1 XVRPXWVGCCHWEO-UHFFFAOYSA-N 0.000 description 1
- YGXLDIPNYNMCCJ-UHFFFAOYSA-N 2-(4-propan-2-ylpyridin-3-yl)-4-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-1,3-thiazole Chemical compound CC(C)C1=CC=NC=C1C1=NC(C=2C=C3C(C(CCC3(C)C)(C)C)=CC=2)=CS1 YGXLDIPNYNMCCJ-UHFFFAOYSA-N 0.000 description 1
- UPDUKHDJHSYPRT-UHFFFAOYSA-N 2-(4-propan-2-ylpyridin-3-yl)-4-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound CC(C)C1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)C(F)(F)F)=CS1 UPDUKHDJHSYPRT-UHFFFAOYSA-N 0.000 description 1
- WTPIUTHVQHLUNU-UHFFFAOYSA-N 2-(4-propan-2-ylpyridin-3-yl)-4-pyridin-2-yl-1,3-thiazole Chemical compound CC(C)C1=CC=NC=C1C1=NC(C=2N=CC=CC=2)=CS1 WTPIUTHVQHLUNU-UHFFFAOYSA-N 0.000 description 1
- YTIFGEQDEITBNC-UHFFFAOYSA-N 2-(4-propan-2-ylpyridin-3-yl)-4-pyridin-4-yl-1,3-thiazole Chemical compound CC(C)C1=CC=NC=C1C1=NC(C=2C=CN=CC=2)=CS1 YTIFGEQDEITBNC-UHFFFAOYSA-N 0.000 description 1
- OCXLVGNFWJEVNW-UHFFFAOYSA-N 2-(4-propan-2-ylpyridin-3-yl)-4-thiophen-3-yl-1,3-thiazole Chemical compound CC(C)C1=CC=NC=C1C1=NC(C2=CSC=C2)=CS1 OCXLVGNFWJEVNW-UHFFFAOYSA-N 0.000 description 1
- BYTRNCJLVQXCIP-UHFFFAOYSA-N 2-(4-tert-butylpyridin-3-yl)-4-(2-nitrophenyl)-1,3-thiazole Chemical compound CC(C)(C)C1=CC=NC=C1C1=NC(C=2C(=CC=CC=2)[N+]([O-])=O)=CS1 BYTRNCJLVQXCIP-UHFFFAOYSA-N 0.000 description 1
- TZLMVDWRNINVAO-UHFFFAOYSA-N 2-(4-tert-butylpyridin-3-yl)-4-(3,4-dichlorophenyl)-1,3-thiazole Chemical compound CC(C)(C)C1=CC=NC=C1C1=NC(C=2C=C(Cl)C(Cl)=CC=2)=CS1 TZLMVDWRNINVAO-UHFFFAOYSA-N 0.000 description 1
- PJCDDZXPRFWSEE-UHFFFAOYSA-N 2-(4-tert-butylpyridin-3-yl)-4-(3-chloro-4-methylphenyl)-5-methyl-1,3-thiazole Chemical compound CC=1SC(C=2C(=CC=NC=2)C(C)(C)C)=NC=1C1=CC=C(C)C(Cl)=C1 PJCDDZXPRFWSEE-UHFFFAOYSA-N 0.000 description 1
- WKKAJBRCWRHSER-UHFFFAOYSA-N 2-(4-tert-butylpyridin-3-yl)-4-(3-nitrophenyl)-1,3-thiazole Chemical compound CC(C)(C)C1=CC=NC=C1C1=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CS1 WKKAJBRCWRHSER-UHFFFAOYSA-N 0.000 description 1
- SMLXNXFBVADKKB-UHFFFAOYSA-N 2-(4-tert-butylpyridin-3-yl)-4-(4-chloro-3-nitrophenyl)-1,3-thiazole Chemical compound CC(C)(C)C1=CC=NC=C1C1=NC(C=2C=C(C(Cl)=CC=2)[N+]([O-])=O)=CS1 SMLXNXFBVADKKB-UHFFFAOYSA-N 0.000 description 1
- NQACIKXJGGZRHC-UHFFFAOYSA-N 2-(4-tert-butylpyridin-3-yl)-5-methyl-4-[4-(2-methylpropyl)phenyl]-1,3-thiazole Chemical compound C1=CC(CC(C)C)=CC=C1C1=C(C)SC(C=2C(=CC=NC=2)C(C)(C)C)=N1 NQACIKXJGGZRHC-UHFFFAOYSA-N 0.000 description 1
- CYUMDMKBWGNWLY-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-4-(2,4-dimethylphenyl)-1,3-thiazole Chemical compound CC1=CC(C)=CC=C1C1=CSC(C=2C=C(Br)C=NC=2)=N1 CYUMDMKBWGNWLY-UHFFFAOYSA-N 0.000 description 1
- FYCSDPSWYDQUFS-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-4-(2,5-dimethoxyphenyl)-1,3-thiazole Chemical compound COC1=CC=C(OC)C(C=2N=C(SC=2)C=2C=C(Br)C=NC=2)=C1 FYCSDPSWYDQUFS-UHFFFAOYSA-N 0.000 description 1
- FZCRJWBDDZBLEW-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-4-(2-chlorophenyl)-1,3-thiazole Chemical compound ClC1=CC=CC=C1C1=CSC(C=2C=C(Br)C=NC=2)=N1 FZCRJWBDDZBLEW-UHFFFAOYSA-N 0.000 description 1
- RXDQWWBXILTIBX-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-4-(2-fluorophenyl)-1,3-thiazole Chemical compound FC1=CC=CC=C1C1=CSC(C=2C=C(Br)C=NC=2)=N1 RXDQWWBXILTIBX-UHFFFAOYSA-N 0.000 description 1
- KAKPPXBOIQBRPD-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-4-(2-methoxyphenyl)-1,3-thiazole Chemical compound COC1=CC=CC=C1C1=CSC(C=2C=C(Br)C=NC=2)=N1 KAKPPXBOIQBRPD-UHFFFAOYSA-N 0.000 description 1
- QBSIGBXKBOCWMZ-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-4-(3,4-dichlorophenyl)-1,3-thiazole Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CSC(C=2C=C(Br)C=NC=2)=N1 QBSIGBXKBOCWMZ-UHFFFAOYSA-N 0.000 description 1
- IAEXQAZQXQZLEH-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-4-(3-chlorophenyl)-1,3-thiazole Chemical compound ClC1=CC=CC(C=2N=C(SC=2)C=2C=C(Br)C=NC=2)=C1 IAEXQAZQXQZLEH-UHFFFAOYSA-N 0.000 description 1
- YURMGDRISVDIQT-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-4-(3-fluorophenyl)-1,3-thiazole Chemical compound FC1=CC=CC(C=2N=C(SC=2)C=2C=C(Br)C=NC=2)=C1 YURMGDRISVDIQT-UHFFFAOYSA-N 0.000 description 1
- SRROUCPQOXDDGE-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-4-(3-nitrophenyl)-1,3-thiazole Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(SC=2)C=2C=C(Br)C=NC=2)=C1 SRROUCPQOXDDGE-UHFFFAOYSA-N 0.000 description 1
- FXOIXIWHRBAYSO-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-4-(4-chloro-3-nitrophenyl)-1,3-thiazole Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(C=2N=C(SC=2)C=2C=C(Br)C=NC=2)=C1 FXOIXIWHRBAYSO-UHFFFAOYSA-N 0.000 description 1
- WCTVILGSSRPYMG-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-4-(4-chlorophenyl)-1,3-thiazole Chemical compound C1=CC(Cl)=CC=C1C1=CSC(C=2C=C(Br)C=NC=2)=N1 WCTVILGSSRPYMG-UHFFFAOYSA-N 0.000 description 1
- RSSZZCJNZHNRRM-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-4-(4-ethylpyridin-3-yl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=CSC(C=2C=C(Br)C=NC=2)=N1 RSSZZCJNZHNRRM-UHFFFAOYSA-N 0.000 description 1
- OHTLOANOOZPMID-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-4-(4-fluorophenyl)-1,3-thiazole Chemical compound C1=CC(F)=CC=C1C1=CSC(C=2C=C(Br)C=NC=2)=N1 OHTLOANOOZPMID-UHFFFAOYSA-N 0.000 description 1
- LZKOLYAFFTTWQQ-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-4-(4-methoxyphenyl)-1,3-thiazole Chemical compound C1=CC(OC)=CC=C1C1=CSC(C=2C=C(Br)C=NC=2)=N1 LZKOLYAFFTTWQQ-UHFFFAOYSA-N 0.000 description 1
- KPDDYRXMYYISEB-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-4-(4-methoxyphenyl)-5-methyl-1,3-thiazole Chemical compound C1=CC(OC)=CC=C1C1=C(C)SC(C=2C=C(Br)C=NC=2)=N1 KPDDYRXMYYISEB-UHFFFAOYSA-N 0.000 description 1
- CHWXIVJQSQQZQP-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-4-(4-methylphenyl)-1,3-thiazole Chemical compound C1=CC(C)=CC=C1C1=CSC(C=2C=C(Br)C=NC=2)=N1 CHWXIVJQSQQZQP-UHFFFAOYSA-N 0.000 description 1
- GKYHNSUMHUIKLL-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-4-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CSC(C=2C=C(Br)C=NC=2)=N1 GKYHNSUMHUIKLL-UHFFFAOYSA-N 0.000 description 1
- QJNKIMAQKWGYBH-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-4-pyridin-3-yl-1,3-thiazole Chemical compound BrC1=CN=CC(C=2SC=C(N=2)C=2C=NC=CC=2)=C1 QJNKIMAQKWGYBH-UHFFFAOYSA-N 0.000 description 1
- KYJLPGHICLSRIC-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-4-tert-butyl-1,3-thiazole Chemical compound CC(C)(C)C1=CSC(C=2C=C(Br)C=NC=2)=N1 KYJLPGHICLSRIC-UHFFFAOYSA-N 0.000 description 1
- SBJPBKFZKADGHJ-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-5-methyl-4-phenyl-1,3-thiazole Chemical compound CC=1SC(C=2C=C(Br)C=NC=2)=NC=1C1=CC=CC=C1 SBJPBKFZKADGHJ-UHFFFAOYSA-N 0.000 description 1
- BBMIWMWCOBEXJS-UHFFFAOYSA-N 2-(5-nitrothiophen-3-yl)-4-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=CSC(C=2C=C(SC=2)[N+]([O-])=O)=N1 BBMIWMWCOBEXJS-UHFFFAOYSA-N 0.000 description 1
- RJBGVAIXGHZIDY-UHFFFAOYSA-N 2-Acetyl-3-methylfuran Chemical compound CC(=O)C=1OC=CC=1C RJBGVAIXGHZIDY-UHFFFAOYSA-N 0.000 description 1
- IYEVQBUAWBANLZ-UHFFFAOYSA-N 2-Acetyl-5-methylfuran Natural products CC(=O)C1=CC(C)=CO1 IYEVQBUAWBANLZ-UHFFFAOYSA-N 0.000 description 1
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical compound CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 description 1
- BYGFEJAVWZCSJN-UHFFFAOYSA-N 2-[(4-chlorophenoxy)methyl]-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(COC=2C=CC(Cl)=CC=2)=N1 BYGFEJAVWZCSJN-UHFFFAOYSA-N 0.000 description 1
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
- ZYDTUGJBXNJSLT-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=N1 ZYDTUGJBXNJSLT-UHFFFAOYSA-N 0.000 description 1
- HJNNBLLEVBOOSB-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)pyridin-3-yl]-4-(3-nitrophenyl)-1,3-thiazole Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C=2C=CC(F)=CC=2)=C1 HJNNBLLEVBOOSB-UHFFFAOYSA-N 0.000 description 1
- NEFKBUJKSVFDOS-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)pyridin-3-yl]-4-(4-nitrophenyl)-1,3-thiazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CSC(C=2C(=CC=NC=2)C=2C=CC(F)=CC=2)=N1 NEFKBUJKSVFDOS-UHFFFAOYSA-N 0.000 description 1
- BMZVSMOBLZQAOS-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)pyridin-3-yl]-4-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(F)=CC=C1C1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)C(F)(F)F)=CS1 BMZVSMOBLZQAOS-UHFFFAOYSA-N 0.000 description 1
- PHRDIHDTVTYEMS-UHFFFAOYSA-N 2-[4-[(4,5-dichloro-1H-imidazol-2-yl)methyl]phenyl]-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound Cc1ccncc1-c1csc(n1)-c1ccc(Cc2nc(Cl)c(Cl)[nH]2)cc1 PHRDIHDTVTYEMS-UHFFFAOYSA-N 0.000 description 1
- 125000005273 2-acetoxybenzoic acid group Chemical group 0.000 description 1
- RNTHCOLZZKPQQH-UHFFFAOYSA-N 2-bromo-1-(3-phenoxyphenyl)ethanone Chemical compound BrCC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 RNTHCOLZZKPQQH-UHFFFAOYSA-N 0.000 description 1
- SAKMPXRILWVZEG-UHFFFAOYSA-N 2-bromo-1-(4-chlorophenyl)propan-1-one Chemical compound CC(Br)C(=O)C1=CC=C(Cl)C=C1 SAKMPXRILWVZEG-UHFFFAOYSA-N 0.000 description 1
- AYNCWMIFKFADCZ-UHFFFAOYSA-N 2-bromo-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2C(=O)C(Br)CCC2=C1 AYNCWMIFKFADCZ-UHFFFAOYSA-N 0.000 description 1
- NAXVBXDTOCUKNH-UHFFFAOYSA-N 2-bromo-6-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1C(Br)CCC2=CC(OC)=CC=C21 NAXVBXDTOCUKNH-UHFFFAOYSA-N 0.000 description 1
- WHEBCCJXJLNMGZ-UHFFFAOYSA-N 2-bromo-7-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CC(Br)C(=O)C2=CC(OC)=CC=C21 WHEBCCJXJLNMGZ-UHFFFAOYSA-N 0.000 description 1
- PNEDZNUPEOAKGR-UHFFFAOYSA-N 2-bromo-n-(3,5-dichlorophenyl)acetamide Chemical compound ClC1=CC(Cl)=CC(NC(=O)CBr)=C1 PNEDZNUPEOAKGR-UHFFFAOYSA-N 0.000 description 1
- OPPUMGDCQYPOSM-UHFFFAOYSA-N 2-bromo-n-phenylpropanamide Chemical compound CC(Br)C(=O)NC1=CC=CC=C1 OPPUMGDCQYPOSM-UHFFFAOYSA-N 0.000 description 1
- VZWFHOCZALVUDS-UHFFFAOYSA-N 2-chloro-1-(4-propan-2-ylpyridin-3-yl)ethanone Chemical compound CC(C)C1=CC=NC=C1C(=O)CCl VZWFHOCZALVUDS-UHFFFAOYSA-N 0.000 description 1
- PBIUDEUWYGBHDW-UHFFFAOYSA-N 2-chloro-1-pyridin-3-ylethanone;hydrochloride Chemical compound Cl.ClCC(=O)C1=CC=CN=C1 PBIUDEUWYGBHDW-UHFFFAOYSA-N 0.000 description 1
- IDPRDGUWSUCLQM-UHFFFAOYSA-N 2-chloro-n-cyclohexyl-n-methylacetamide Chemical compound ClCC(=O)N(C)C1CCCCC1 IDPRDGUWSUCLQM-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- YRGYYQCOWUULNF-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-1h-pyridine-3-carbonitrile Chemical compound CC1=CC(=O)NC(O)=C1C#N YRGYYQCOWUULNF-UHFFFAOYSA-N 0.000 description 1
- CSYKIMRZZIHPGT-UHFFFAOYSA-N 2-isoquinolin-4-yl-1,3-thiazole Chemical class C1=CSC(C=2C3=CC=CC=C3C=NC=2)=N1 CSYKIMRZZIHPGT-UHFFFAOYSA-N 0.000 description 1
- RQNADZXPWBGCNB-UHFFFAOYSA-N 2-isoquinolin-4-yl-4-(2-methoxyphenyl)-1,3-thiazole Chemical compound COC1=CC=CC=C1C1=CSC(C=2C3=CC=CC=C3C=NC=2)=N1 RQNADZXPWBGCNB-UHFFFAOYSA-N 0.000 description 1
- NVSWUXPJSJJNGS-UHFFFAOYSA-N 2-isoquinolin-4-yl-4-(2-nitrophenyl)-1,3-thiazole Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=CSC(C=2C3=CC=CC=C3C=NC=2)=N1 NVSWUXPJSJJNGS-UHFFFAOYSA-N 0.000 description 1
- BBYIXVGQKCNXIE-UHFFFAOYSA-N 2-isoquinolin-4-yl-4-(3-nitrophenyl)-1,3-thiazole Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(SC=2)C=2C3=CC=CC=C3C=NC=2)=C1 BBYIXVGQKCNXIE-UHFFFAOYSA-N 0.000 description 1
- CORJBMQUFDKUHC-UHFFFAOYSA-N 2-isoquinolin-4-yl-4-(4-methoxyphenyl)-1,3-thiazole Chemical compound C1=CC(OC)=CC=C1C1=CSC(C=2C3=CC=CC=C3C=NC=2)=N1 CORJBMQUFDKUHC-UHFFFAOYSA-N 0.000 description 1
- VIVGCDIFEMXRJK-UHFFFAOYSA-N 2-isoquinolin-4-yl-4-(4-methylphenyl)-1,3-thiazole Chemical compound C1=CC(C)=CC=C1C1=CSC(C=2C3=CC=CC=C3C=NC=2)=N1 VIVGCDIFEMXRJK-UHFFFAOYSA-N 0.000 description 1
- CTXPJKOOROPOSV-UHFFFAOYSA-N 2-isoquinolin-4-yl-4-(4-nitrophenyl)-1,3-thiazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CSC(C=2C3=CC=CC=C3C=NC=2)=N1 CTXPJKOOROPOSV-UHFFFAOYSA-N 0.000 description 1
- ZKSQETSSXQLILQ-UHFFFAOYSA-N 2-isoquinolin-4-yl-4-(4-phenylphenyl)-1,3-thiazole Chemical compound C=1SC(C=2C3=CC=CC=C3C=NC=2)=NC=1C(C=C1)=CC=C1C1=CC=CC=C1 ZKSQETSSXQLILQ-UHFFFAOYSA-N 0.000 description 1
- KYZBYXZOLNURGV-UHFFFAOYSA-N 2-isoquinolin-4-yl-4-[4-(trifluoromethoxy)phenyl]-1,3-thiazole Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CSC(C=2C3=CC=CC=C3C=NC=2)=N1 KYZBYXZOLNURGV-UHFFFAOYSA-N 0.000 description 1
- CIYDNKZPQRWINZ-UHFFFAOYSA-N 2-isoquinolin-4-yl-4-naphthalen-2-yl-1,3-thiazole Chemical compound C1=CC=C2C(C=3SC=C(N=3)C=3C=C4C=CC=CC4=CC=3)=CN=CC2=C1 CIYDNKZPQRWINZ-UHFFFAOYSA-N 0.000 description 1
- RFSJOSFWAUCNAL-UHFFFAOYSA-N 2-isoquinolin-4-yl-4-phenyl-1,3-thiazole Chemical compound C=1SC(C=2C3=CC=CC=C3C=NC=2)=NC=1C1=CC=CC=C1 RFSJOSFWAUCNAL-UHFFFAOYSA-N 0.000 description 1
- JYJIMEQNTHFXMT-UHFFFAOYSA-N 2-nitro-2-phenylacetic acid Chemical compound OC(=O)C([N+]([O-])=O)C1=CC=CC=C1 JYJIMEQNTHFXMT-UHFFFAOYSA-N 0.000 description 1
- RRNZYRWOXFSCFZ-UHFFFAOYSA-N 2-phenyl-4-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=CSC(C=2C=CC=CC=2)=N1 RRNZYRWOXFSCFZ-UHFFFAOYSA-N 0.000 description 1
- PVHNKILPLXXDDZ-UHFFFAOYSA-N 2-phenylcycloheptan-1-one Chemical compound O=C1CCCCCC1C1=CC=CC=C1 PVHNKILPLXXDDZ-UHFFFAOYSA-N 0.000 description 1
- BBMDOXGZPVRMAS-UHFFFAOYSA-N 2-pyrazin-2-yl-4-pyridin-4-yl-1,3-thiazole Chemical compound C=1SC(C=2N=CC=NC=2)=NC=1C1=CC=NC=C1 BBMDOXGZPVRMAS-UHFFFAOYSA-N 0.000 description 1
- CXUQFOTVDMEFLV-UHFFFAOYSA-N 2-pyridin-3-yl-4,5,6,7-tetrahydro-1,3-benzothiazole Chemical compound N=1C=2CCCCC=2SC=1C1=CC=CN=C1 CXUQFOTVDMEFLV-UHFFFAOYSA-N 0.000 description 1
- NCHIWMMRHASYBA-UHFFFAOYSA-N 2-pyridin-3-yl-4,5-dihydrobenzo[e][1,3]benzothiazole Chemical compound S1C=2CCC3=CC=CC=C3C=2N=C1C1=CC=CN=C1 NCHIWMMRHASYBA-UHFFFAOYSA-N 0.000 description 1
- QYKVJCIJLYCHTN-UHFFFAOYSA-N 2-pyridin-3-yl-4-pyridin-4-yl-1,3-thiazole Chemical compound C=1SC(C=2C=NC=CC=2)=NC=1C1=CC=NC=C1 QYKVJCIJLYCHTN-UHFFFAOYSA-N 0.000 description 1
- FTLPTQLUAAHFIV-UHFFFAOYSA-N 2-pyridin-3-yl-5,6,7,8-tetrahydro-4h-cyclohepta[d][1,3]thiazole Chemical compound S1C=2CCCCCC=2N=C1C1=CC=CN=C1 FTLPTQLUAAHFIV-UHFFFAOYSA-N 0.000 description 1
- ORBPTKWRWHCTKD-UHFFFAOYSA-N 2-pyridin-3-yl-5,6-dihydro-4h-cyclopenta[d][1,3]thiazole Chemical compound S1C=2CCCC=2N=C1C1=CC=CN=C1 ORBPTKWRWHCTKD-UHFFFAOYSA-N 0.000 description 1
- DBHBGFLKXJTYPE-UHFFFAOYSA-N 2-pyridin-3-yl-6,7-dihydro-4h-[1,3]thiazolo[4,5-d]pyrimidin-5-one Chemical compound N=1C=2NC(=O)NCC=2SC=1C1=CC=CN=C1 DBHBGFLKXJTYPE-UHFFFAOYSA-N 0.000 description 1
- OIPHWUPMXHQWLR-UHFFFAOYSA-N 2-pyridin-3-ylacetonitrile Chemical compound N#CCC1=CC=CN=C1 OIPHWUPMXHQWLR-UHFFFAOYSA-N 0.000 description 1
- VSBVYPLNYOJQEV-UHFFFAOYSA-N 2-pyridin-3-ylethanethioamide Chemical compound NC(=S)CC1=CC=CN=C1 VSBVYPLNYOJQEV-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- ILXZWWRJENLCAP-UHFFFAOYSA-N 3-(2-isoquinolin-4-yl-1,3-thiazol-4-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2N=C(SC=2)C=2C3=CC=CC=C3C=NC=2)=C1 ILXZWWRJENLCAP-UHFFFAOYSA-N 0.000 description 1
- OKBWQBPTFKAYNT-UHFFFAOYSA-N 3-[2-(4-cyclopentylpyridin-3-yl)-1,3-thiazol-4-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C2CCCC2)=C1 OKBWQBPTFKAYNT-UHFFFAOYSA-N 0.000 description 1
- KCGVBQCAONREEU-UHFFFAOYSA-N 3-[2-(4-cyclopropylpyridin-3-yl)-1,3-thiazol-4-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C2CC2)=C1 KCGVBQCAONREEU-UHFFFAOYSA-N 0.000 description 1
- XEUGDBBPPMQBOE-UHFFFAOYSA-N 3-[2-(4-ethylpyridin-3-yl)-1,3-thiazol-4-yl]benzonitrile Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=C(C=CC=2)C#N)=CS1 XEUGDBBPPMQBOE-UHFFFAOYSA-N 0.000 description 1
- KDUYDLLJPHEHQD-UHFFFAOYSA-N 3-[2-(4-methylpyridin-3-yl)-1,3-thiazol-4-yl]benzonitrile Chemical compound CC1=CC=NC=C1C1=NC(C=2C=C(C=CC=2)C#N)=CS1 KDUYDLLJPHEHQD-UHFFFAOYSA-N 0.000 description 1
- INIMFKDBDPDXHL-UHFFFAOYSA-N 3-[2-(4-phenylpyridin-3-yl)-1,3-thiazol-4-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C=2C=CC=CC=2)=C1 INIMFKDBDPDXHL-UHFFFAOYSA-N 0.000 description 1
- UNCXMTTZYBUROJ-UHFFFAOYSA-N 3-[2-(4-propylpyridin-3-yl)-1,3-thiazol-4-yl]benzonitrile Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C=C(C=CC=2)C#N)=CS1 UNCXMTTZYBUROJ-UHFFFAOYSA-N 0.000 description 1
- LPVYNKWPAYUBQX-UHFFFAOYSA-N 3-[2-(5-bromopyridin-3-yl)-1,3-thiazol-4-yl]benzonitrile Chemical compound BrC1=CN=CC(C=2SC=C(N=2)C=2C=C(C=CC=2)C#N)=C1 LPVYNKWPAYUBQX-UHFFFAOYSA-N 0.000 description 1
- NOAXZTPXUADVGC-UHFFFAOYSA-N 3-[2-[4-(4-fluorophenyl)pyridin-3-yl]-1,3-thiazol-4-yl]benzonitrile Chemical compound C1=CC(F)=CC=C1C1=CC=NC=C1C1=NC(C=2C=C(C=CC=2)C#N)=CS1 NOAXZTPXUADVGC-UHFFFAOYSA-N 0.000 description 1
- RTCRCILIBGSBLX-UHFFFAOYSA-N 3-[4-(4-cyclopropylpyridin-3-yl)-1,3-thiazol-2-yl]-6-methyl-1h-pyridin-2-one Chemical compound OC1=NC(C)=CC=C1C1=NC(C=2C(=CC=NC=2)C2CC2)=CS1 RTCRCILIBGSBLX-UHFFFAOYSA-N 0.000 description 1
- PJLYHSZOMPICQL-UHFFFAOYSA-N 3-[4-(4-cyclopropylpyridin-3-yl)-1,3-thiazol-2-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2SC=C(N=2)C=2C(=CC=NC=2)C2CC2)=C1 PJLYHSZOMPICQL-UHFFFAOYSA-N 0.000 description 1
- PRRZDZJYSJLDBS-UHFFFAOYSA-N 3-bromo-2-oxopropanoic acid Chemical compound OC(=O)C(=O)CBr PRRZDZJYSJLDBS-UHFFFAOYSA-N 0.000 description 1
- HGINADPHJQTSKN-UHFFFAOYSA-M 3-ethoxy-3-oxopropanoate Chemical compound CCOC(=O)CC([O-])=O HGINADPHJQTSKN-UHFFFAOYSA-M 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- JOWXBGIZDALBJW-UHFFFAOYSA-N 3h-dioxepine Chemical compound C1OOC=CC=C1 JOWXBGIZDALBJW-UHFFFAOYSA-N 0.000 description 1
- MSWFVMZAPMGXES-UHFFFAOYSA-N 4,5-dimethyl-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound S1C(C)=C(C)N=C1C1=CN=CC=C1C MSWFVMZAPMGXES-UHFFFAOYSA-N 0.000 description 1
- MTPXNANFFKHDQE-UHFFFAOYSA-N 4-(1-adamantyl)-2-(4-cyclopropylpyridin-3-yl)-1,3-thiazole Chemical compound C1CC1C1=CC=NC=C1C1=NC(C23CC4CC(CC(C4)C2)C3)=CS1 MTPXNANFFKHDQE-UHFFFAOYSA-N 0.000 description 1
- HXAGJHJFXMQSCT-UHFFFAOYSA-N 4-(1-adamantyl)-2-(4-ethylpyridin-3-yl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C23CC4CC(CC(C4)C2)C3)=CS1 HXAGJHJFXMQSCT-UHFFFAOYSA-N 0.000 description 1
- QVZSYHNHKGPJJP-UHFFFAOYSA-N 4-(1-adamantyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C23CC4CC(CC(C4)C2)C3)=CS1 QVZSYHNHKGPJJP-UHFFFAOYSA-N 0.000 description 1
- UWEBLKNDEONPFF-UHFFFAOYSA-N 4-(1-adamantyl)-2-(5-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CN=CC(C=2SC=C(N=2)C23CC4CC(CC(C4)C2)C3)=C1 UWEBLKNDEONPFF-UHFFFAOYSA-N 0.000 description 1
- FGGVBFADPWYAMB-UHFFFAOYSA-N 4-(1-adamantyl)-2-pyridin-3-yl-1,3-thiazole Chemical compound C1C(C2)CC(C3)CC1CC23C(N=1)=CSC=1C1=CC=CN=C1 FGGVBFADPWYAMB-UHFFFAOYSA-N 0.000 description 1
- PYMXAVUQIZMUCQ-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-2-(4-ethylpyridin-3-yl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C(=CC(Cl)=CC=2)Cl)=CS1 PYMXAVUQIZMUCQ-UHFFFAOYSA-N 0.000 description 1
- UTXMPZSPSXVRIP-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole;hydrochloride Chemical compound Cl.CC1=CC=NC=C1C1=NC(C=2C(=CC(Cl)=CC=2)Cl)=CS1 UTXMPZSPSXVRIP-UHFFFAOYSA-N 0.000 description 1
- OOVNXQQFOIIWCK-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-2-(4-phenylpyridin-3-yl)-1,3-thiazole Chemical compound ClC1=CC(Cl)=CC=C1C1=CSC(C=2C(=CC=NC=2)C=2C=CC=CC=2)=N1 OOVNXQQFOIIWCK-UHFFFAOYSA-N 0.000 description 1
- GGAFTCDPMQGWIX-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-2-[4-(4-fluorophenyl)pyridin-3-yl]-1,3-thiazole Chemical compound C1=CC(F)=CC=C1C1=CC=NC=C1C1=NC(C=2C(=CC(Cl)=CC=2)Cl)=CS1 GGAFTCDPMQGWIX-UHFFFAOYSA-N 0.000 description 1
- VYVQJDUYBOKBTB-UHFFFAOYSA-N 4-(2,4-dimethoxyphenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound COC1=CC(OC)=CC=C1C1=CSC(C=2C(=CC=NC=2)C)=N1 VYVQJDUYBOKBTB-UHFFFAOYSA-N 0.000 description 1
- VQJNKGAFYYXARM-UHFFFAOYSA-N 4-(2,4-dimethoxyphenyl)-2-isoquinolin-4-yl-1,3-thiazole Chemical compound COC1=CC(OC)=CC=C1C1=CSC(C=2C3=CC=CC=C3C=NC=2)=N1 VQJNKGAFYYXARM-UHFFFAOYSA-N 0.000 description 1
- XTSLNFFUBIXFGK-UHFFFAOYSA-N 4-(2,4-dimethylphenyl)-2-(4-ethylpyridin-3-yl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=CS1 XTSLNFFUBIXFGK-UHFFFAOYSA-N 0.000 description 1
- GSSSABQVFGWJNY-UHFFFAOYSA-N 4-(2,4-dimethylphenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC(C)=CC=C1C1=CSC(C=2C(=CC=NC=2)C)=N1 GSSSABQVFGWJNY-UHFFFAOYSA-N 0.000 description 1
- VZHWUFVCHGMMJW-UHFFFAOYSA-N 4-(2,4-dimethylphenyl)-2-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=CS1 VZHWUFVCHGMMJW-UHFFFAOYSA-N 0.000 description 1
- RZNBDNFZZYMPPV-UHFFFAOYSA-N 4-(2,4-dimethylphenyl)-2-isoquinolin-4-yl-1,3-thiazole Chemical compound CC1=CC(C)=CC=C1C1=CSC(C=2C3=CC=CC=C3C=NC=2)=N1 RZNBDNFZZYMPPV-UHFFFAOYSA-N 0.000 description 1
- XKOOYXVEVKFTOR-UHFFFAOYSA-N 4-(2,5-dimethoxyphenyl)-2-(4-ethylpyridin-3-yl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C(=CC=C(OC)C=2)OC)=CS1 XKOOYXVEVKFTOR-UHFFFAOYSA-N 0.000 description 1
- SSRUYCKSKLYOSM-UHFFFAOYSA-N 4-(2,6-dimethoxyphenyl)-2-(5-methylpyridin-3-yl)-1,3-thiazole Chemical compound COC1=CC=CC(OC)=C1C1=CSC(C=2C=C(C)C=NC=2)=N1 SSRUYCKSKLYOSM-UHFFFAOYSA-N 0.000 description 1
- WHJGYMWHRMZULT-UHFFFAOYSA-N 4-(2-bromophenyl)-2-(4-tert-butylpyridin-3-yl)-1,3-thiazole Chemical compound CC(C)(C)C1=CC=NC=C1C1=NC(C=2C(=CC=CC=2)Br)=CS1 WHJGYMWHRMZULT-UHFFFAOYSA-N 0.000 description 1
- DAWWQNUICQEKKD-UHFFFAOYSA-N 4-(2-chlorophenyl)-2-(4-cyclopentylpyridin-3-yl)-1,3-thiazole Chemical compound ClC1=CC=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CCCC2)=N1 DAWWQNUICQEKKD-UHFFFAOYSA-N 0.000 description 1
- XPJGQWRHHYZVCK-UHFFFAOYSA-N 4-(2-chlorophenyl)-2-(4-cyclopropylpyridin-3-yl)-1,3-thiazole Chemical compound ClC1=CC=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CC2)=N1 XPJGQWRHHYZVCK-UHFFFAOYSA-N 0.000 description 1
- RIVIABQMFHSURY-UHFFFAOYSA-N 4-(2-chlorophenyl)-2-(4-ethylpyridin-3-yl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C(=CC=CC=2)Cl)=CS1 RIVIABQMFHSURY-UHFFFAOYSA-N 0.000 description 1
- MZULEJRZUAPUAV-UHFFFAOYSA-N 4-(2-chlorophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C(=CC=CC=2)Cl)=CS1 MZULEJRZUAPUAV-UHFFFAOYSA-N 0.000 description 1
- RAVBYZRNARLENU-UHFFFAOYSA-N 4-(2-chlorophenyl)-2-(4-phenylpyridin-3-yl)-1,3-thiazole Chemical compound ClC1=CC=CC=C1C1=CSC(C=2C(=CC=NC=2)C=2C=CC=CC=2)=N1 RAVBYZRNARLENU-UHFFFAOYSA-N 0.000 description 1
- AUAHQBYRCGDQKN-UHFFFAOYSA-N 4-(2-chlorophenyl)-2-(4-propan-2-ylpyridin-3-yl)-1,3-thiazole Chemical compound CC(C)C1=CC=NC=C1C1=NC(C=2C(=CC=CC=2)Cl)=CS1 AUAHQBYRCGDQKN-UHFFFAOYSA-N 0.000 description 1
- LYJGWPQEWPBZDH-UHFFFAOYSA-N 4-(2-chlorophenyl)-2-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C(=CC=CC=2)Cl)=CS1 LYJGWPQEWPBZDH-UHFFFAOYSA-N 0.000 description 1
- LQEQWXHBIVCXCL-UHFFFAOYSA-N 4-(2-chlorophenyl)-2-isoquinolin-4-yl-1,3-thiazole Chemical compound ClC1=CC=CC=C1C1=CSC(C=2C3=CC=CC=C3C=NC=2)=N1 LQEQWXHBIVCXCL-UHFFFAOYSA-N 0.000 description 1
- ZQLNZOUHSZJOIJ-UHFFFAOYSA-N 4-(2-fluorophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C(=CC=CC=2)F)=CS1 ZQLNZOUHSZJOIJ-UHFFFAOYSA-N 0.000 description 1
- PQDHWHFTJZXXAD-UHFFFAOYSA-N 4-(2-fluorophenyl)-2-(4-phenylpyridin-3-yl)-1,3-thiazole Chemical compound FC1=CC=CC=C1C1=CSC(C=2C(=CC=NC=2)C=2C=CC=CC=2)=N1 PQDHWHFTJZXXAD-UHFFFAOYSA-N 0.000 description 1
- KVLFNFLPDWSDFS-UHFFFAOYSA-N 4-(2-fluorophenyl)-2-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C(=CC=CC=2)F)=CS1 KVLFNFLPDWSDFS-UHFFFAOYSA-N 0.000 description 1
- XBWQXBXXZAQBEV-UHFFFAOYSA-N 4-(2-fluorophenyl)-2-isoquinolin-4-yl-1,3-thiazole Chemical compound FC1=CC=CC=C1C1=CSC(C=2C3=CC=CC=C3C=NC=2)=N1 XBWQXBXXZAQBEV-UHFFFAOYSA-N 0.000 description 1
- REWTYNMXRVPHNT-UHFFFAOYSA-N 4-(2-methoxyphenyl)-2-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C(=CC=CC=2)OC)=CS1 REWTYNMXRVPHNT-UHFFFAOYSA-N 0.000 description 1
- MDYHKXYWVQHHKB-UHFFFAOYSA-N 4-(2-nitrophenyl)-2-(4-phenylpyridin-3-yl)-1,3-thiazole Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=CSC(C=2C(=CC=NC=2)C=2C=CC=CC=2)=N1 MDYHKXYWVQHHKB-UHFFFAOYSA-N 0.000 description 1
- JFHWQXXXAAQHEI-UHFFFAOYSA-N 4-(2-nitrophenyl)-2-(4-propan-2-ylpyridin-3-yl)-1,3-thiazole Chemical compound CC(C)C1=CC=NC=C1C1=NC(C=2C(=CC=CC=2)[N+]([O-])=O)=CS1 JFHWQXXXAAQHEI-UHFFFAOYSA-N 0.000 description 1
- QHKDTQIHPRFAAQ-UHFFFAOYSA-N 4-(2-nitrophenyl)-2-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C(=CC=CC=2)[N+]([O-])=O)=CS1 QHKDTQIHPRFAAQ-UHFFFAOYSA-N 0.000 description 1
- ZZSIVTLRGAXQNI-UHFFFAOYSA-N 4-(2-nitrophenyl)-2-(pyridin-3-ylmethyl)-1,3-thiazole Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=CSC(CC=2C=NC=CC=2)=N1 ZZSIVTLRGAXQNI-UHFFFAOYSA-N 0.000 description 1
- ADKLAHAHHIHEMI-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-(4-ethylpyridin-3-yl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=C(Cl)C(Cl)=CC=2)=CS1 ADKLAHAHHIHEMI-UHFFFAOYSA-N 0.000 description 1
- FJVSALTZHGGNPU-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=C(Cl)C(Cl)=CC=2)=CS1 FJVSALTZHGGNPU-UHFFFAOYSA-N 0.000 description 1
- BOQRXPXCRDHDHB-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-[4-(4-fluorophenyl)pyridin-3-yl]-1,3-thiazole Chemical compound C1=CC(F)=CC=C1C1=CC=NC=C1C1=NC(C=2C=C(Cl)C(Cl)=CC=2)=CS1 BOQRXPXCRDHDHB-UHFFFAOYSA-N 0.000 description 1
- KWLIEKXMKGFWKB-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-isoquinolin-4-yl-1,3-thiazole Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CSC(C=2C3=CC=CC=C3C=NC=2)=N1 KWLIEKXMKGFWKB-UHFFFAOYSA-N 0.000 description 1
- CQQLFNOYXRCFML-UHFFFAOYSA-N 4-(3,4-difluorophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=C(F)C(F)=CC=2)=CS1 CQQLFNOYXRCFML-UHFFFAOYSA-N 0.000 description 1
- ABOACWXEQQDYCL-UHFFFAOYSA-N 4-(3,4-dihydro-2h-1,5-benzodioxepin-7-yl)-2-(4-propan-2-ylpyridin-3-yl)-1,3-thiazole Chemical compound CC(C)C1=CC=NC=C1C1=NC(C=2C=C3OCCCOC3=CC=2)=CS1 ABOACWXEQQDYCL-UHFFFAOYSA-N 0.000 description 1
- BRSCWCQROXHYNJ-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-2-(pyridin-3-ylmethyl)-1,3-thiazole Chemical compound CC1=CC(C)=CC(C=2N=C(CC=3C=NC=CC=3)SC=2)=C1 BRSCWCQROXHYNJ-UHFFFAOYSA-N 0.000 description 1
- OLNWQMSOIWUOPN-UHFFFAOYSA-N 4-(3-bicyclo[2.2.1]heptanylmethoxy)-2-pyridin-3-yl-1,3-thiazole Chemical compound C1C(C2)CCC2C1COC(N=1)=CSC=1C1=CC=CN=C1 OLNWQMSOIWUOPN-UHFFFAOYSA-N 0.000 description 1
- WDQRSXSENXVPBQ-UHFFFAOYSA-N 4-(3-bromophenyl)-2-(4-cyclopentylpyridin-3-yl)-1,3-thiazole Chemical compound BrC1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C2CCCC2)=C1 WDQRSXSENXVPBQ-UHFFFAOYSA-N 0.000 description 1
- DWGLYJLHGPDDDH-UHFFFAOYSA-N 4-(3-bromophenyl)-2-(4-ethylpyridin-3-yl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=C(Br)C=CC=2)=CS1 DWGLYJLHGPDDDH-UHFFFAOYSA-N 0.000 description 1
- CAUUXOIHQPHRHC-UHFFFAOYSA-N 4-(3-bromophenyl)-2-(4-phenylpyridin-3-yl)-1,3-thiazole Chemical compound BrC1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C=2C=CC=CC=2)=C1 CAUUXOIHQPHRHC-UHFFFAOYSA-N 0.000 description 1
- IQZMBAJSRQKZDJ-UHFFFAOYSA-N 4-(3-bromophenyl)-2-(4-propan-2-ylpyridin-3-yl)-1,3-thiazole Chemical compound CC(C)C1=CC=NC=C1C1=NC(C=2C=C(Br)C=CC=2)=CS1 IQZMBAJSRQKZDJ-UHFFFAOYSA-N 0.000 description 1
- QVRBDIBYFJHJBX-UHFFFAOYSA-N 4-(3-bromophenyl)-2-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C=C(Br)C=CC=2)=CS1 QVRBDIBYFJHJBX-UHFFFAOYSA-N 0.000 description 1
- RVUKIFXTAIVZJD-UHFFFAOYSA-N 4-(3-bromophenyl)-2-(5-bromopyridin-3-yl)-1,3-thiazole Chemical compound BrC1=CC=CC(C=2N=C(SC=2)C=2C=C(Br)C=NC=2)=C1 RVUKIFXTAIVZJD-UHFFFAOYSA-N 0.000 description 1
- RQWSZKBKWQELMT-UHFFFAOYSA-N 4-(3-bromophenyl)-2-isoquinolin-4-yl-1,3-thiazole Chemical compound BrC1=CC=CC(C=2N=C(SC=2)C=2C3=CC=CC=C3C=NC=2)=C1 RQWSZKBKWQELMT-UHFFFAOYSA-N 0.000 description 1
- VOSGFJOGOXRJON-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-(4-cyclopentylpyridin-3-yl)-1,3-thiazole Chemical compound ClC1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C2CCCC2)=C1 VOSGFJOGOXRJON-UHFFFAOYSA-N 0.000 description 1
- VAAHNHUMIXNRME-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-(4-cyclopropylpyridin-3-yl)-1,3-thiazole Chemical compound ClC1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C2CC2)=C1 VAAHNHUMIXNRME-UHFFFAOYSA-N 0.000 description 1
- FSGAYBYJHZGXPT-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-(4-ethylpyridin-3-yl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=C(Cl)C=CC=2)=CS1 FSGAYBYJHZGXPT-UHFFFAOYSA-N 0.000 description 1
- FVIGGINYSZMHBN-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=C(Cl)C=CC=2)=CS1 FVIGGINYSZMHBN-UHFFFAOYSA-N 0.000 description 1
- ATEFNESPVHXBBS-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-(4-phenylpyridin-3-yl)-1,3-thiazole Chemical compound ClC1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C=2C=CC=CC=2)=C1 ATEFNESPVHXBBS-UHFFFAOYSA-N 0.000 description 1
- VETIACZQLPQOKM-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C=C(Cl)C=CC=2)=CS1 VETIACZQLPQOKM-UHFFFAOYSA-N 0.000 description 1
- VUUQTEUNIAMGQZ-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-[4-(4-fluorophenyl)pyridin-3-yl]-1,3-thiazole Chemical compound C1=CC(F)=CC=C1C1=CC=NC=C1C1=NC(C=2C=C(Cl)C=CC=2)=CS1 VUUQTEUNIAMGQZ-UHFFFAOYSA-N 0.000 description 1
- NGLDBOUWPKWMII-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-isoquinolin-4-yl-1,3-thiazole Chemical compound ClC1=CC=CC(C=2N=C(SC=2)C=2C3=CC=CC=C3C=NC=2)=C1 NGLDBOUWPKWMII-UHFFFAOYSA-N 0.000 description 1
- BHPNWFRIUAODKT-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=C(F)C=CC=2)=CS1 BHPNWFRIUAODKT-UHFFFAOYSA-N 0.000 description 1
- UHNQJWSKXOGYDG-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-(4-phenylpyridin-3-yl)-1,3-thiazole Chemical compound FC1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C=2C=CC=CC=2)=C1 UHNQJWSKXOGYDG-UHFFFAOYSA-N 0.000 description 1
- JRNCMZNDERKWTO-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-(4-propan-2-ylpyridin-3-yl)-1,3-thiazole Chemical compound CC(C)C1=CC=NC=C1C1=NC(C=2C=C(F)C=CC=2)=CS1 JRNCMZNDERKWTO-UHFFFAOYSA-N 0.000 description 1
- VFARMGAPXAXBND-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-(pyridin-3-ylmethyl)-1,3-thiazole Chemical compound FC1=CC=CC(C=2N=C(CC=3C=NC=CC=3)SC=2)=C1 VFARMGAPXAXBND-UHFFFAOYSA-N 0.000 description 1
- KOQHRVFLPFATDF-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[4-(4-fluorophenyl)pyridin-3-yl]-1,3-thiazole Chemical compound C1=CC(F)=CC=C1C1=CC=NC=C1C1=NC(C=2C=C(F)C=CC=2)=CS1 KOQHRVFLPFATDF-UHFFFAOYSA-N 0.000 description 1
- IBSPABPAUZTABE-UHFFFAOYSA-N 4-(3-methoxyphenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound COC1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C)=C1 IBSPABPAUZTABE-UHFFFAOYSA-N 0.000 description 1
- DGBDWUQNFQQQRR-UHFFFAOYSA-N 4-(3-methoxyphenyl)-2-(pyridin-3-ylmethyl)-1,3-thiazole Chemical compound COC1=CC=CC(C=2N=C(CC=3C=NC=CC=3)SC=2)=C1 DGBDWUQNFQQQRR-UHFFFAOYSA-N 0.000 description 1
- VIUOUZQCZMZRFV-UHFFFAOYSA-N 4-(3-nitrophenyl)-2-(4-phenylpyridin-3-yl)-1,3-thiazole Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C=2C=CC=CC=2)=C1 VIUOUZQCZMZRFV-UHFFFAOYSA-N 0.000 description 1
- CSJZXHPYGPVYPQ-UHFFFAOYSA-N 4-(3-nitrophenyl)-2-(4-propan-2-ylpyridin-3-yl)-1,3-thiazole Chemical compound CC(C)C1=CC=NC=C1C1=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CS1 CSJZXHPYGPVYPQ-UHFFFAOYSA-N 0.000 description 1
- VTWDHDQGKGBBPW-UHFFFAOYSA-N 4-(3-nitrophenyl)-2-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CS1 VTWDHDQGKGBBPW-UHFFFAOYSA-N 0.000 description 1
- WUJZHUDRMYOWIE-UHFFFAOYSA-N 4-(4-bromophenyl)-2-(4-cyclopentylpyridin-3-yl)-1,3-thiazole Chemical compound C1=CC(Br)=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CCCC2)=N1 WUJZHUDRMYOWIE-UHFFFAOYSA-N 0.000 description 1
- VAYKNTYSPBGDAB-UHFFFAOYSA-N 4-(4-bromophenyl)-2-(4-cyclopentylpyridin-3-yl)-5-methyl-1,3-thiazole Chemical compound CC=1SC(C=2C(=CC=NC=2)C2CCCC2)=NC=1C1=CC=C(Br)C=C1 VAYKNTYSPBGDAB-UHFFFAOYSA-N 0.000 description 1
- URFKHTFDYCPUFC-UHFFFAOYSA-N 4-(4-bromophenyl)-2-(4-cyclopropylpyridin-3-yl)-1,3-thiazole Chemical compound C1=CC(Br)=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CC2)=N1 URFKHTFDYCPUFC-UHFFFAOYSA-N 0.000 description 1
- ASKNJMOWTCYDGL-UHFFFAOYSA-N 4-(4-bromophenyl)-2-(4-cyclopropylpyridin-3-yl)-5-methyl-1,3-thiazole Chemical compound CC=1SC(C=2C(=CC=NC=2)C2CC2)=NC=1C1=CC=C(Br)C=C1 ASKNJMOWTCYDGL-UHFFFAOYSA-N 0.000 description 1
- OEBXZHKEOLQKEX-UHFFFAOYSA-N 4-(4-bromophenyl)-2-(4-ethylpyridin-3-yl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=CC(Br)=CC=2)=CS1 OEBXZHKEOLQKEX-UHFFFAOYSA-N 0.000 description 1
- AXVLCAXVHWYQFV-UHFFFAOYSA-N 4-(4-bromophenyl)-2-(4-ethylpyridin-3-yl)-5-methyl-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=CC(Br)=CC=2)=C(C)S1 AXVLCAXVHWYQFV-UHFFFAOYSA-N 0.000 description 1
- GCRKZUKPBBFJRD-UHFFFAOYSA-N 4-(4-bromophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=CC(Br)=CC=2)=CS1 GCRKZUKPBBFJRD-UHFFFAOYSA-N 0.000 description 1
- QYNNMKSPXNXOQG-UHFFFAOYSA-N 4-(4-bromophenyl)-2-(4-propan-2-ylpyridin-3-yl)-1,3-thiazole Chemical compound CC(C)C1=CC=NC=C1C1=NC(C=2C=CC(Br)=CC=2)=CS1 QYNNMKSPXNXOQG-UHFFFAOYSA-N 0.000 description 1
- FBMZHPNVWLRWCR-UHFFFAOYSA-N 4-(4-bromophenyl)-2-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C=CC(Br)=CC=2)=CS1 FBMZHPNVWLRWCR-UHFFFAOYSA-N 0.000 description 1
- PTHXBYULAVERDJ-UHFFFAOYSA-N 4-(4-bromophenyl)-2-(5-bromopyridin-3-yl)-1,3-thiazole Chemical compound C1=CC(Br)=CC=C1C1=CSC(C=2C=C(Br)C=NC=2)=N1 PTHXBYULAVERDJ-UHFFFAOYSA-N 0.000 description 1
- UMASADUBKSYHQR-UHFFFAOYSA-N 4-(4-bromophenyl)-2-(5-bromopyridin-3-yl)-5-methyl-1,3-thiazole Chemical compound CC=1SC(C=2C=C(Br)C=NC=2)=NC=1C1=CC=C(Br)C=C1 UMASADUBKSYHQR-UHFFFAOYSA-N 0.000 description 1
- BKYVSCQOZPPKGR-UHFFFAOYSA-N 4-(4-bromophenyl)-2-isoquinolin-4-yl-1,3-thiazole Chemical compound C1=CC(Br)=CC=C1C1=CSC(C=2C3=CC=CC=C3C=NC=2)=N1 BKYVSCQOZPPKGR-UHFFFAOYSA-N 0.000 description 1
- KGQGEPAJHDILMK-UHFFFAOYSA-N 4-(4-bromophenyl)-2-isoquinolin-4-yl-5-methyl-1,3-thiazole Chemical compound CC=1SC(C=2C3=CC=CC=C3C=NC=2)=NC=1C1=CC=C(Br)C=C1 KGQGEPAJHDILMK-UHFFFAOYSA-N 0.000 description 1
- FDUCNLDFYXYMAD-UHFFFAOYSA-N 4-(4-bromophenyl)-5-methyl-2-(4-propan-2-ylpyridin-3-yl)-1,3-thiazole Chemical compound CC(C)C1=CC=NC=C1C1=NC(C=2C=CC(Br)=CC=2)=C(C)S1 FDUCNLDFYXYMAD-UHFFFAOYSA-N 0.000 description 1
- GGOJNUBJWSCBJK-UHFFFAOYSA-N 4-(4-bromophenyl)-5-methyl-2-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C=CC(Br)=CC=2)=C(C)S1 GGOJNUBJWSCBJK-UHFFFAOYSA-N 0.000 description 1
- LQZWIFBMWVKCGO-UHFFFAOYSA-N 4-(4-chloro-3-nitrophenyl)-2-(4-cyclopentylpyridin-3-yl)-1,3-thiazole Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C2CCCC2)=C1 LQZWIFBMWVKCGO-UHFFFAOYSA-N 0.000 description 1
- SDBUGDJXKDHSAP-UHFFFAOYSA-N 4-(4-chloro-3-nitrophenyl)-2-(4-cyclopropylpyridin-3-yl)-1,3-thiazole Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C2CC2)=C1 SDBUGDJXKDHSAP-UHFFFAOYSA-N 0.000 description 1
- XEXJELZNEYWIDH-UHFFFAOYSA-N 4-(4-chloro-3-nitrophenyl)-2-(4-ethylpyridin-3-yl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=C(C(Cl)=CC=2)[N+]([O-])=O)=CS1 XEXJELZNEYWIDH-UHFFFAOYSA-N 0.000 description 1
- VEVOVMJIODSKBS-UHFFFAOYSA-N 4-(4-chloro-3-nitrophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=C(C(Cl)=CC=2)[N+]([O-])=O)=CS1 VEVOVMJIODSKBS-UHFFFAOYSA-N 0.000 description 1
- QZUZILQMSJCNNS-UHFFFAOYSA-N 4-(4-chloro-3-nitrophenyl)-2-isoquinolin-4-yl-1,3-thiazole Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(C=2N=C(SC=2)C=2C3=CC=CC=C3C=NC=2)=C1 QZUZILQMSJCNNS-UHFFFAOYSA-N 0.000 description 1
- HBGBFZSJRUDOKI-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(1h-imidazol-2-ylmethyl)-1,3-thiazole Chemical compound C1=CC(Cl)=CC=C1C1=CSC(CC=2NC=CN=2)=N1 HBGBFZSJRUDOKI-UHFFFAOYSA-N 0.000 description 1
- IQKICDYFJPYGRC-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(4-cyclopentylpyridin-3-yl)-1,3-thiazole Chemical compound C1=CC(Cl)=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CCCC2)=N1 IQKICDYFJPYGRC-UHFFFAOYSA-N 0.000 description 1
- QUFRHEUEAXLEJR-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(4-cyclopentylpyridin-3-yl)-5-methyl-1,3-thiazole Chemical compound CC=1SC(C=2C(=CC=NC=2)C2CCCC2)=NC=1C1=CC=C(Cl)C=C1 QUFRHEUEAXLEJR-UHFFFAOYSA-N 0.000 description 1
- SBEUKCFEFXLUJU-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(4-cyclopropylpyridin-3-yl)-1,3-thiazole Chemical compound C1=CC(Cl)=CC=C1C1=CSC(C=2C(=CC=NC=2)C2CC2)=N1 SBEUKCFEFXLUJU-UHFFFAOYSA-N 0.000 description 1
- NHGABCXQPHBART-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(4-cyclopropylpyridin-3-yl)-5-methyl-1,3-thiazole Chemical compound CC=1SC(C=2C(=CC=NC=2)C2CC2)=NC=1C1=CC=C(Cl)C=C1 NHGABCXQPHBART-UHFFFAOYSA-N 0.000 description 1
- ZNBYUFMLNPKCCF-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(4-ethylpyridin-3-yl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C=2C=CC(Cl)=CC=2)=CS1 ZNBYUFMLNPKCCF-UHFFFAOYSA-N 0.000 description 1
- ZUSHMNGDFSOMJY-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(4-methoxypyridin-3-yl)-1,3-thiazole Chemical compound COC1=CC=NC=C1C1=NC(C=2C=CC(Cl)=CC=2)=CS1 ZUSHMNGDFSOMJY-UHFFFAOYSA-N 0.000 description 1
- CTZZPUJKHRAUSW-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(4-methylpyridin-3-yl)-5-propyl-1,3-thiazole Chemical compound CCCC=1SC(C=2C(=CC=NC=2)C)=NC=1C1=CC=C(Cl)C=C1 CTZZPUJKHRAUSW-UHFFFAOYSA-N 0.000 description 1
- RKWWFYMBYBDFCT-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(4-phenylpyridin-3-yl)-1,3-thiazole Chemical compound C1=CC(Cl)=CC=C1C1=CSC(C=2C(=CC=NC=2)C=2C=CC=CC=2)=N1 RKWWFYMBYBDFCT-UHFFFAOYSA-N 0.000 description 1
- WKMVIUAHVQSCRA-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(4-piperazin-1-ylpyridin-3-yl)-1,3-thiazole Chemical compound C1=CC(Cl)=CC=C1C1=CSC(C=2C(=CC=NC=2)N2CCNCC2)=N1 WKMVIUAHVQSCRA-UHFFFAOYSA-N 0.000 description 1
- DWQSODVPVIMWRH-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(4-propan-2-ylpyridin-3-yl)-1,3-thiazole Chemical compound CC(C)C1=CC=NC=C1C1=NC(C=2C=CC(Cl)=CC=2)=CS1 DWQSODVPVIMWRH-UHFFFAOYSA-N 0.000 description 1
- QQSHCHOIGVOXLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C=CC(Cl)=CC=2)=CS1 QQSHCHOIGVOXLE-UHFFFAOYSA-N 0.000 description 1
- UJMCCHHILPPFFS-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(5-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CN=CC(C=2SC=C(N=2)C=2C=CC(Cl)=CC=2)=C1 UJMCCHHILPPFFS-UHFFFAOYSA-N 0.000 description 1
- GYLKWPXCAAQFJQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-[4-(2-methylpropyl)pyridin-3-yl]-1,3-thiazole Chemical compound CC(C)CC1=CC=NC=C1C1=NC(C=2C=CC(Cl)=CC=2)=CS1 GYLKWPXCAAQFJQ-UHFFFAOYSA-N 0.000 description 1
- ZWFZZKBKEIJVNT-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-[4-(4-fluorophenyl)pyridin-3-yl]-1,3-thiazole Chemical compound C1=CC(F)=CC=C1C1=CC=NC=C1C1=NC(C=2C=CC(Cl)=CC=2)=CS1 ZWFZZKBKEIJVNT-UHFFFAOYSA-N 0.000 description 1
- YXWQMUDQFBNJLT-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-isoquinolin-4-yl-1,3-thiazole Chemical compound C1=CC(Cl)=CC=C1C1=CSC(C=2C3=CC=CC=C3C=NC=2)=N1 YXWQMUDQFBNJLT-UHFFFAOYSA-N 0.000 description 1
- LCUAYWCNWKGGPN-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(4-methylphenyl)-2-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCc1ccncc1-c1nc(c(s1)-c1ccc(C)cc1)-c1ccc(Cl)cc1 LCUAYWCNWKGGPN-UHFFFAOYSA-N 0.000 description 1
- KTXOXYUCVMOZSC-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-ethyl-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CCC=1SC(C=2C(=CC=NC=2)C)=NC=1C1=CC=C(Cl)C=C1 KTXOXYUCVMOZSC-UHFFFAOYSA-N 0.000 description 1
- WHRNHTBOPCCCOF-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-ethyl-2-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C=CC(Cl)=CC=2)=C(CC)S1 WHRNHTBOPCCCOF-UHFFFAOYSA-N 0.000 description 1
- ZNXNHHMVNMFGPG-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-iodo-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=CC(Cl)=CC=2)=C(I)S1 ZNXNHHMVNMFGPG-UHFFFAOYSA-N 0.000 description 1
- JDHKVBHGPPREOL-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-methyl-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC=1SC(C=2C(=CC=NC=2)C)=NC=1C1=CC=C(Cl)C=C1 JDHKVBHGPPREOL-UHFFFAOYSA-N 0.000 description 1
- KRIAVCCOKNRYLA-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-methyl-2-pyridin-3-yl-1,3-thiazole Chemical compound CC=1SC(C=2C=NC=CC=2)=NC=1C1=CC=C(Cl)C=C1 KRIAVCCOKNRYLA-UHFFFAOYSA-N 0.000 description 1
- WTHKFNWRKHPPKH-UHFFFAOYSA-N 4-(4-cyclopropylpyridin-3-yl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C(=CC=NC=2)C2CC2)=CS1 WTHKFNWRKHPPKH-UHFFFAOYSA-N 0.000 description 1
- TZLSMOAEVGIRLZ-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=CC(F)=CC=2)=CS1 TZLSMOAEVGIRLZ-UHFFFAOYSA-N 0.000 description 1
- IGFSISDBPFFRIE-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(4-phenylpyridin-3-yl)-1,3-thiazole Chemical compound C1=CC(F)=CC=C1C1=CSC(C=2C(=CC=NC=2)C=2C=CC=CC=2)=N1 IGFSISDBPFFRIE-UHFFFAOYSA-N 0.000 description 1
- LXXYXCDXYUOITF-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C=CC(F)=CC=2)=CS1 LXXYXCDXYUOITF-UHFFFAOYSA-N 0.000 description 1
- DTFXKABSCYGTFR-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-[4-(4-fluorophenyl)pyridin-3-yl]-1,3-thiazole Chemical compound C1=CC(F)=CC=C1C1=CSC(C=2C(=CC=NC=2)C=2C=CC(F)=CC=2)=N1 DTFXKABSCYGTFR-UHFFFAOYSA-N 0.000 description 1
- ZUSOKGZZXYQDCR-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-isoquinolin-4-yl-1,3-thiazole Chemical compound C1=CC(F)=CC=C1C1=CSC(C=2C3=CC=CC=C3C=NC=2)=N1 ZUSOKGZZXYQDCR-UHFFFAOYSA-N 0.000 description 1
- QQQAPIQEVIJTIC-UHFFFAOYSA-N 4-(4-methoxyphenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound C1=CC(OC)=CC=C1C1=CSC(C=2C(=CC=NC=2)C)=N1 QQQAPIQEVIJTIC-UHFFFAOYSA-N 0.000 description 1
- MKJDIPYEENRORL-UHFFFAOYSA-N 4-(4-methoxyphenyl)-2-(4-phenylpyridin-3-yl)-1,3-thiazole Chemical compound C1=CC(OC)=CC=C1C1=CSC(C=2C(=CC=NC=2)C=2C=CC=CC=2)=N1 MKJDIPYEENRORL-UHFFFAOYSA-N 0.000 description 1
- ZRQVOODHCLRMFS-UHFFFAOYSA-N 4-(4-methoxyphenyl)-2-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C=CC(OC)=CC=2)=CS1 ZRQVOODHCLRMFS-UHFFFAOYSA-N 0.000 description 1
- OQJMAQUBLBUTFP-UHFFFAOYSA-N 4-(4-methylphenyl)-2-(4-phenylpyridin-3-yl)-1,3-thiazole Chemical compound C1=CC(C)=CC=C1C1=CSC(C=2C(=CC=NC=2)C=2C=CC=CC=2)=N1 OQJMAQUBLBUTFP-UHFFFAOYSA-N 0.000 description 1
- MINUZRHFAUQENO-UHFFFAOYSA-N 4-(4-methylphenyl)-2-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C=CC(C)=CC=2)=CS1 MINUZRHFAUQENO-UHFFFAOYSA-N 0.000 description 1
- OZRREZSLXXPFRT-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(N)=N1 OZRREZSLXXPFRT-UHFFFAOYSA-N 0.000 description 1
- MJGLQGZSICWGFI-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-2-(2-nitrophenyl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C(=CC=CC=2)[N+]([O-])=O)=N1 MJGLQGZSICWGFI-UHFFFAOYSA-N 0.000 description 1
- HHGFRQAXLUPDNS-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-2-(3-nitrophenyl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C=C(C=CC=2)[N+]([O-])=O)=N1 HHGFRQAXLUPDNS-UHFFFAOYSA-N 0.000 description 1
- LZEOUPTVROXJMT-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-2-(4-nitrophenyl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C=CC(=CC=2)[N+]([O-])=O)=N1 LZEOUPTVROXJMT-UHFFFAOYSA-N 0.000 description 1
- HBHLZHKXZVZSDQ-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-2-(4-phenylphenyl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 HBHLZHKXZVZSDQ-UHFFFAOYSA-N 0.000 description 1
- HSPVVXONIOXXOU-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-2-(4-phenylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C(=CC=NC=2)C=2C=CC=CC=2)=N1 HSPVVXONIOXXOU-UHFFFAOYSA-N 0.000 description 1
- QCMVBZCECOMBLV-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-2-(4-propan-2-ylpyridin-3-yl)-1,3-thiazole Chemical compound CC(C)C1=CC=NC=C1C1=NC(C=2C(=CC=NC=2)C)=CS1 QCMVBZCECOMBLV-UHFFFAOYSA-N 0.000 description 1
- CSQUBLIOOBKUGV-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-2-pyrazin-2-yl-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2N=CC=NC=2)=N1 CSQUBLIOOBKUGV-UHFFFAOYSA-N 0.000 description 1
- CBNZFPWNVBFNPA-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-2-thiophen-2-yl-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2SC=CC=2)=N1 CBNZFPWNVBFNPA-UHFFFAOYSA-N 0.000 description 1
- YYTYEIKNQHPWRR-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-N-[2-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine Chemical compound Cc1ccncc1-c1csc(Nc2ccccc2C(F)(F)F)n1 YYTYEIKNQHPWRR-UHFFFAOYSA-N 0.000 description 1
- HNWXMVATACOKTP-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-N-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine Chemical compound Cc1ccncc1-c1csc(Nc2cccc(c2)C(F)(F)F)n1 HNWXMVATACOKTP-UHFFFAOYSA-N 0.000 description 1
- FVZJLAFDZKRUEH-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-N-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine Chemical compound Cc1ccncc1-c1csc(Nc2ccc(cc2)C(F)(F)F)n1 FVZJLAFDZKRUEH-UHFFFAOYSA-N 0.000 description 1
- GVFJCJAYYBWJNI-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-n-(2-phenylethyl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(NCCC=2C=CC=CC=2)=N1 GVFJCJAYYBWJNI-UHFFFAOYSA-N 0.000 description 1
- LTASWILUDWBIRL-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-n-(3-morpholin-4-ylpropyl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(NCCCN2CCOCC2)=N1 LTASWILUDWBIRL-UHFFFAOYSA-N 0.000 description 1
- PKGIATDUPXZVIB-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-n-(4-nitrophenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(NC=2C=CC(=CC=2)[N+]([O-])=O)=N1 PKGIATDUPXZVIB-UHFFFAOYSA-N 0.000 description 1
- RVWWAWBKVFUXRA-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-n-(oxolan-2-ylmethyl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(NCC2OCCC2)=N1 RVWWAWBKVFUXRA-UHFFFAOYSA-N 0.000 description 1
- YHWGAUVGDVWADP-UHFFFAOYSA-N 4-(4-nitrophenyl)-2-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)[N+]([O-])=O)=CS1 YHWGAUVGDVWADP-UHFFFAOYSA-N 0.000 description 1
- HEKCGNOGKLNWQB-UHFFFAOYSA-N 4-(4-phenylphenyl)-2-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=CS1 HEKCGNOGKLNWQB-UHFFFAOYSA-N 0.000 description 1
- DWVIEZZKJVTKDI-UHFFFAOYSA-N 4-(4-propylpyridin-3-yl)-2-[4-(trifluoromethyl)pyridin-3-yl]-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=CSC(C=2C(=CC=NC=2)C(F)(F)F)=N1 DWVIEZZKJVTKDI-UHFFFAOYSA-N 0.000 description 1
- BMUSUSMPQQCWII-UHFFFAOYSA-N 4-(4-propylpyridin-3-yl)-2-pyrazin-2-yl-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=CSC(C=2N=CC=NC=2)=N1 BMUSUSMPQQCWII-UHFFFAOYSA-N 0.000 description 1
- BEPWISGSDLTZAN-UHFFFAOYSA-N 4-(4-propylpyridin-3-yl)-2-pyridin-4-yl-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=CSC(C=2C=CN=CC=2)=N1 BEPWISGSDLTZAN-UHFFFAOYSA-N 0.000 description 1
- JPUHCODHUJDOFV-UHFFFAOYSA-N 4-(4-propylpyridin-3-yl)-2-thiophen-2-yl-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=CSC(C=2SC=CC=2)=N1 JPUHCODHUJDOFV-UHFFFAOYSA-N 0.000 description 1
- LMRKJMBVLKBHCD-UHFFFAOYSA-N 4-(4-propylpyridin-3-yl)-2-thiophen-3-yl-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=CSC(C2=CSC=C2)=N1 LMRKJMBVLKBHCD-UHFFFAOYSA-N 0.000 description 1
- IRJDPFWHNCGWAV-UHFFFAOYSA-N 4-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-2-[4-(trifluoromethyl)pyridin-3-yl]-1,3-thiazole Chemical compound CC1(C)CCC(C)(C)c2cc(ccc12)-c1csc(n1)-c1cnccc1C(F)(F)F IRJDPFWHNCGWAV-UHFFFAOYSA-N 0.000 description 1
- KOLWGLKYUQJTOM-UHFFFAOYSA-N 4-(5a,9a-dihydrodibenzofuran-2-yl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound Cc1ccncc1-c1nc(cs1)-c1ccc2OC3C=CC=CC3c2c1 KOLWGLKYUQJTOM-UHFFFAOYSA-N 0.000 description 1
- AGZZFPYSHXMFHS-UHFFFAOYSA-N 4-(cyclopenten-1-yl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2CCCC=2)=CS1 AGZZFPYSHXMFHS-UHFFFAOYSA-N 0.000 description 1
- FPZUJXSAWFDDSR-UHFFFAOYSA-N 4-(cyclopenten-1-yl)-2-(4-propan-2-ylpyridin-3-yl)-1,3-thiazole Chemical compound CC(C)c1ccncc1-c1nc(cs1)C1=CCCC1 FPZUJXSAWFDDSR-UHFFFAOYSA-N 0.000 description 1
- NLYBUGGCFPXHAT-UHFFFAOYSA-N 4-(cyclopenten-1-yl)-2-pyridin-3-yl-1,3-thiazole Chemical compound C1CCC=C1C1=CSC(C=2C=NC=CC=2)=N1 NLYBUGGCFPXHAT-UHFFFAOYSA-N 0.000 description 1
- HHWAAUMMZLLJNC-UHFFFAOYSA-N 4-(furan-3-yl)-2-(4-propan-2-ylpyridin-3-yl)-1,3-thiazole Chemical compound CC(C)C1=CC=NC=C1C1=NC(C2=COC=C2)=CS1 HHWAAUMMZLLJNC-UHFFFAOYSA-N 0.000 description 1
- QOWSWEBLNVACCL-UHFFFAOYSA-N 4-Bromophenyl acetate Chemical compound OC(=O)CC1=CC=C(Br)C=C1 QOWSWEBLNVACCL-UHFFFAOYSA-N 0.000 description 1
- UBWPVMUEOUUQPV-UHFFFAOYSA-N 4-[(3,4-dichlorophenyl)methyl]-2-pyridin-3-yl-1,3-thiazole Chemical compound C1=C(Cl)C(Cl)=CC=C1CC1=CSC(C=2C=NC=CC=2)=N1 UBWPVMUEOUUQPV-UHFFFAOYSA-N 0.000 description 1
- DXPXNEPFACKUHM-UHFFFAOYSA-N 4-[(3-chlorophenyl)methyl]-2-pyridin-3-yl-1,3-thiazole Chemical compound ClC1=CC=CC(CC=2N=C(SC=2)C=2C=NC=CC=2)=C1 DXPXNEPFACKUHM-UHFFFAOYSA-N 0.000 description 1
- BTKKXVGENZXFJC-UHFFFAOYSA-N 4-[(3-methylphenyl)methyl]-2-pyridin-3-yl-1,3-thiazole Chemical compound CC1=CC=CC(CC=2N=C(SC=2)C=2C=NC=CC=2)=C1 BTKKXVGENZXFJC-UHFFFAOYSA-N 0.000 description 1
- FPLFJMNVRSWMJT-UHFFFAOYSA-N 4-[(3-nitrophenyl)methyl]-2-pyridin-3-yl-1,3-thiazole Chemical compound [O-][N+](=O)C1=CC=CC(CC=2N=C(SC=2)C=2C=NC=CC=2)=C1 FPLFJMNVRSWMJT-UHFFFAOYSA-N 0.000 description 1
- ZGTFQOZROMMDJJ-UHFFFAOYSA-N 4-[(4-bromophenyl)methyl]-2-pyridin-3-yl-1,3-thiazole Chemical compound C1=CC(Br)=CC=C1CC1=CSC(C=2C=NC=CC=2)=N1 ZGTFQOZROMMDJJ-UHFFFAOYSA-N 0.000 description 1
- XMVLLYPXVBBOCU-UHFFFAOYSA-N 4-[(4-chlorophenyl)methyl]-2-(4-methylpyridin-3-yl)-1,3-thiazole;hydrochloride Chemical compound Cl.CC1=CC=NC=C1C1=NC(CC=2C=CC(Cl)=CC=2)=CS1 XMVLLYPXVBBOCU-UHFFFAOYSA-N 0.000 description 1
- LHYGRICZRFTITF-UHFFFAOYSA-N 4-[(4-chlorophenyl)methyl]-2-pyridin-3-yl-1,3-thiazole Chemical compound C1=CC(Cl)=CC=C1CC1=CSC(C=2C=NC=CC=2)=N1 LHYGRICZRFTITF-UHFFFAOYSA-N 0.000 description 1
- GKYJKPOXGNTRQJ-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-2-pyridin-3-yl-1,3-thiazole Chemical compound C1=CC(F)=CC=C1CC1=CSC(C=2C=NC=CC=2)=N1 GKYJKPOXGNTRQJ-UHFFFAOYSA-N 0.000 description 1
- UURVNHDBMYFSOR-UHFFFAOYSA-N 4-[(4-methylphenyl)methyl]-2-pyridin-3-yl-1,3-thiazole Chemical compound C1=CC(C)=CC=C1CC1=CSC(C=2C=NC=CC=2)=N1 UURVNHDBMYFSOR-UHFFFAOYSA-N 0.000 description 1
- DATYIDDZAFCNRF-UHFFFAOYSA-N 4-[2-(1-hydroxy-4-methyl-2h-pyridin-3-yl)-1,3-thiazol-4-yl]benzonitrile Chemical compound C1N(O)C=CC(C)=C1C1=NC(C=2C=CC(=CC=2)C#N)=CS1 DATYIDDZAFCNRF-UHFFFAOYSA-N 0.000 description 1
- NWABCEFDVWTLDZ-UHFFFAOYSA-N 4-[2-(4-methylpyridin-3-yl)-1,3-thiazol-4-yl]benzenecarboximidamide Chemical compound CC1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)C(N)=N)=CS1 NWABCEFDVWTLDZ-UHFFFAOYSA-N 0.000 description 1
- UWWLJPXSMUXNOG-UHFFFAOYSA-N 4-[2-(4-methylpyridin-3-yl)-1,3-thiazol-4-yl]benzoic acid Chemical compound CC1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)C(O)=O)=CS1 UWWLJPXSMUXNOG-UHFFFAOYSA-N 0.000 description 1
- FLLDHGVBDXSTRW-UHFFFAOYSA-N 4-[2-(4-phenylpyridin-3-yl)-1,3-thiazol-4-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CSC(C=2C(=CC=NC=2)C=2C=CC=CC=2)=N1 FLLDHGVBDXSTRW-UHFFFAOYSA-N 0.000 description 1
- PCQDSSAFQGLFSN-UHFFFAOYSA-N 4-[2-(4-propylpyridin-3-yl)-1,3-thiazol-4-yl]benzonitrile Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)C#N)=CS1 PCQDSSAFQGLFSN-UHFFFAOYSA-N 0.000 description 1
- FNYOJSMQGRMVML-UHFFFAOYSA-N 4-[2-(5-bromopyridin-3-yl)-1,3-thiazol-4-yl]-5-methyl-3-phenyl-1,2-oxazole Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C(N=1)=CSC=1C1=CN=CC(Br)=C1 FNYOJSMQGRMVML-UHFFFAOYSA-N 0.000 description 1
- YTFRZTVAEBYGEC-UHFFFAOYSA-N 4-[2-(5-bromopyridin-3-yl)-1,3-thiazol-4-yl]benzonitrile Chemical compound BrC1=CN=CC(C=2SC=C(N=2)C=2C=CC(=CC=2)C#N)=C1 YTFRZTVAEBYGEC-UHFFFAOYSA-N 0.000 description 1
- DKOZINCSWBDROO-UHFFFAOYSA-N 4-[2-[4-(1H-imidazol-2-ylmethyl)pyridin-3-yl]-1,3-thiazol-4-yl]benzonitrile Chemical compound N#Cc1ccc(cc1)-c1csc(n1)-c1cnccc1Cc1ncc[nH]1 DKOZINCSWBDROO-UHFFFAOYSA-N 0.000 description 1
- PWGILJUJBUGTLF-UHFFFAOYSA-N 4-[2-[4-(4-fluorophenyl)pyridin-3-yl]-1,3-thiazol-4-yl]benzonitrile Chemical compound C1=CC(F)=CC=C1C1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)C#N)=CS1 PWGILJUJBUGTLF-UHFFFAOYSA-N 0.000 description 1
- LIDSMURSFKTMQR-UHFFFAOYSA-N 4-[2-[4-(methylaminomethyl)pyridin-3-yl]-1,3-thiazol-4-yl]benzonitrile Chemical compound CNCc1ccncc1-c1nc(cs1)-c1ccc(cc1)C#N LIDSMURSFKTMQR-UHFFFAOYSA-N 0.000 description 1
- LSLLNTVXTPCCQF-UHFFFAOYSA-N 4-[2-[4-(morpholin-4-ylmethyl)pyridin-3-yl]-1,3-thiazol-4-yl]benzonitrile Chemical compound N#Cc1ccc(cc1)-c1csc(n1)-c1cnccc1CN1CCOCC1 LSLLNTVXTPCCQF-UHFFFAOYSA-N 0.000 description 1
- KDIZIVDBONLNOF-UHFFFAOYSA-N 4-[2-[4-(pyrrolidin-1-ylmethyl)pyridin-3-yl]-1,3-thiazol-4-yl]benzonitrile Chemical compound N#Cc1ccc(cc1)-c1csc(n1)-c1cnccc1CN1CCCC1 KDIZIVDBONLNOF-UHFFFAOYSA-N 0.000 description 1
- OYOUDUDAWQHONH-UHFFFAOYSA-N 4-[2-[4-[(2-methoxyethylamino)methyl]pyridin-3-yl]-1,3-thiazol-4-yl]benzonitrile Chemical compound COCCNCc1ccncc1-c1nc(cs1)-c1ccc(cc1)C#N OYOUDUDAWQHONH-UHFFFAOYSA-N 0.000 description 1
- LXWPFSSGJVJKLE-UHFFFAOYSA-N 4-[2-[4-[(4-propan-2-ylpiperazin-1-yl)methyl]pyridin-3-yl]-1,3-thiazol-4-yl]benzonitrile Chemical compound CC(C)N1CCN(Cc2ccncc2-c2nc(cs2)-c2ccc(cc2)C#N)CC1 LXWPFSSGJVJKLE-UHFFFAOYSA-N 0.000 description 1
- CXFJDEBAONUUHG-UHFFFAOYSA-N 4-[2-[4-[(4-pyridin-4-ylpiperazin-1-yl)methyl]pyridin-3-yl]-1,3-thiazol-4-yl]benzonitrile Chemical compound N#Cc1ccc(cc1)-c1csc(n1)-c1cnccc1CN1CCN(CC1)c1ccncc1 CXFJDEBAONUUHG-UHFFFAOYSA-N 0.000 description 1
- CMNIYUXVPTWUIO-UHFFFAOYSA-N 4-[2-[4-[(dimethylamino)methyl]pyridin-3-yl]-1,3-thiazol-4-yl]benzonitrile Chemical compound CN(C)CC1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)C#N)=CS1 CMNIYUXVPTWUIO-UHFFFAOYSA-N 0.000 description 1
- VTYONMHFEGAPEB-UHFFFAOYSA-N 4-[2-[4-[(propan-2-ylamino)methyl]pyridin-3-yl]-1,3-thiazol-4-yl]benzonitrile Chemical compound CC(C)NCc1ccncc1-c1nc(cs1)-c1ccc(cc1)C#N VTYONMHFEGAPEB-UHFFFAOYSA-N 0.000 description 1
- JPHXFWYBODFMLZ-UHFFFAOYSA-N 4-[2-[4-[[2-(dimethylamino)ethylamino]methyl]pyridin-3-yl]-1,3-thiazol-4-yl]benzonitrile Chemical compound CN(C)CCNCc1ccncc1-c1nc(cs1)-c1ccc(cc1)C#N JPHXFWYBODFMLZ-UHFFFAOYSA-N 0.000 description 1
- QMYILZCVDHCJCM-UHFFFAOYSA-N 4-[3,5-bis(trifluoromethyl)phenyl]-2-(4-cyclopentylpyridin-3-yl)-1,3-thiazole Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C2CCCC2)=C1 QMYILZCVDHCJCM-UHFFFAOYSA-N 0.000 description 1
- MMHBKJIECZONBF-UHFFFAOYSA-N 4-[3,5-bis(trifluoromethyl)phenyl]-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=CS1 MMHBKJIECZONBF-UHFFFAOYSA-N 0.000 description 1
- GGXWTFASOMFJGV-UHFFFAOYSA-N 4-[3,5-bis(trifluoromethyl)phenyl]-2-(4-propan-2-ylpyridin-3-yl)-1,3-thiazole Chemical compound CC(C)C1=CC=NC=C1C1=NC(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=CS1 GGXWTFASOMFJGV-UHFFFAOYSA-N 0.000 description 1
- IUMWUMQYWOYDHW-UHFFFAOYSA-N 4-[3-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]pyridin-4-yl]morpholine Chemical compound C1=CC(Cl)=CC=C1C1=CSC(C=2C(=CC=NC=2)N2CCOCC2)=N1 IUMWUMQYWOYDHW-UHFFFAOYSA-N 0.000 description 1
- LMLXEWGPVZXFSD-UHFFFAOYSA-N 4-[4-(1-hydroxy-4-methyl-2h-pyridin-3-yl)-1,3-thiazol-2-yl]benzonitrile Chemical compound C1N(O)C=CC(C)=C1C1=CSC(C=2C=CC(=CC=2)C#N)=N1 LMLXEWGPVZXFSD-UHFFFAOYSA-N 0.000 description 1
- OTCXSKOZOOEGLF-UHFFFAOYSA-N 4-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]benzenecarboximidamide Chemical compound CC1=CC=NC=C1C1=CSC(C=2C=CC(=CC=2)C(N)=N)=N1 OTCXSKOZOOEGLF-UHFFFAOYSA-N 0.000 description 1
- HSTOWFHUHCTUDS-UHFFFAOYSA-N 4-[4-(4-propylpyridin-3-yl)-1,3-thiazol-2-yl]benzonitrile Chemical compound CCCC1=CC=NC=C1C1=CSC(C=2C=CC(=CC=2)C#N)=N1 HSTOWFHUHCTUDS-UHFFFAOYSA-N 0.000 description 1
- IVDTWITVXKYNSQ-UHFFFAOYSA-N 4-[4-(difluoromethoxy)phenyl]-2-(4-phenylpyridin-3-yl)-1,3-thiazole Chemical compound C1=CC(OC(F)F)=CC=C1C1=CSC(C=2C(=CC=NC=2)C=2C=CC=CC=2)=N1 IVDTWITVXKYNSQ-UHFFFAOYSA-N 0.000 description 1
- BXCNYMJBKNSDBT-UHFFFAOYSA-N 4-[4-(difluoromethoxy)phenyl]-2-[4-(4-fluorophenyl)pyridin-3-yl]-1,3-thiazole Chemical compound C1=CC(OC(F)F)=CC=C1C1=CSC(C=2C(=CC=NC=2)C=2C=CC(F)=CC=2)=N1 BXCNYMJBKNSDBT-UHFFFAOYSA-N 0.000 description 1
- GMNAUJRPWSQRSE-UHFFFAOYSA-N 4-[4-(difluoromethoxy)phenyl]-2-isoquinolin-4-yl-1,3-thiazole Chemical compound C1=CC(OC(F)F)=CC=C1C1=CSC(C=2C3=CC=CC=C3C=NC=2)=N1 GMNAUJRPWSQRSE-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- XYBSFUSZSQDNKN-YIZWMMSDSA-N 4-[[(3s)-3-bicyclo[2.2.1]heptanyl]oxy]-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(O[C@@H]2C3CCC(C3)C2)=CS1 XYBSFUSZSQDNKN-YIZWMMSDSA-N 0.000 description 1
- YCARVZHSHNWKFE-XIVSLSHWSA-N 4-[[(3s)-3-bicyclo[2.2.1]heptanyl]oxy]-2-pyridin-3-yl-1,3-thiazole Chemical compound O([C@H]1CC2CC1CC2)C(N=1)=CSC=1C1=CC=CN=C1 YCARVZHSHNWKFE-XIVSLSHWSA-N 0.000 description 1
- SCRBSGZBTHKAHU-UHFFFAOYSA-N 4-bromoisoquinoline Chemical compound C1=CC=C2C(Br)=CN=CC2=C1 SCRBSGZBTHKAHU-UHFFFAOYSA-N 0.000 description 1
- QPZZXUSDMMSSNG-UHFFFAOYSA-N 4-cyclobutyl-2-pyridin-3-yl-1,3-thiazole Chemical compound C1CCC1C1=CSC(C=2C=NC=CC=2)=N1 QPZZXUSDMMSSNG-UHFFFAOYSA-N 0.000 description 1
- RERRCBLLTKFXTH-UHFFFAOYSA-N 4-cyclobutyloxy-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(OC2CCC2)=CS1 RERRCBLLTKFXTH-UHFFFAOYSA-N 0.000 description 1
- GCNJYHYBXLGZKV-UHFFFAOYSA-N 4-cyclobutyloxy-2-pyridin-3-yl-1,3-thiazole Chemical compound C1CCC1OC1=CSC(C=2C=NC=CC=2)=N1 GCNJYHYBXLGZKV-UHFFFAOYSA-N 0.000 description 1
- VNBUQZALXAFITN-UHFFFAOYSA-N 4-cycloheptyl-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C2CCCCCC2)=CS1 VNBUQZALXAFITN-UHFFFAOYSA-N 0.000 description 1
- ZWMIBTRXZWMPFA-UHFFFAOYSA-N 4-cycloheptyloxy-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(OC2CCCCCC2)=CS1 ZWMIBTRXZWMPFA-UHFFFAOYSA-N 0.000 description 1
- MJJAPSLJOATJEZ-UHFFFAOYSA-N 4-cycloheptyloxy-2-pyridin-3-yl-1,3-thiazole Chemical compound C1CCCCCC1OC1=CSC(C=2C=NC=CC=2)=N1 MJJAPSLJOATJEZ-UHFFFAOYSA-N 0.000 description 1
- BNBGCOMURHPZMJ-UHFFFAOYSA-N 4-cyclohexyl-2-(4-cyclopropylpyridin-3-yl)-1,3-thiazole Chemical compound C1CC1C1=CC=NC=C1C1=NC(C2CCCCC2)=CS1 BNBGCOMURHPZMJ-UHFFFAOYSA-N 0.000 description 1
- YFHGSEGJUMNHOX-UHFFFAOYSA-N 4-cyclohexyl-2-(4-ethylpyridin-3-yl)-1,3-thiazole Chemical compound CCC1=CC=NC=C1C1=NC(C2CCCCC2)=CS1 YFHGSEGJUMNHOX-UHFFFAOYSA-N 0.000 description 1
- SHGZAVFOKMTCIZ-UHFFFAOYSA-N 4-cyclohexyl-2-(4-methylpyridin-2-yl)-1,3-thiazole Chemical compound CC1=CC=NC(C=2SC=C(N=2)C2CCCCC2)=C1 SHGZAVFOKMTCIZ-UHFFFAOYSA-N 0.000 description 1
- KBMKOOYFFIZBBK-UHFFFAOYSA-N 4-cyclohexyl-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C2CCCCC2)=CS1 KBMKOOYFFIZBBK-UHFFFAOYSA-N 0.000 description 1
- MOPJAYOZSLXMBK-UHFFFAOYSA-N 4-cyclohexyl-2-(4-propan-2-ylpyridin-3-yl)-1,3-thiazole Chemical compound CC(C)c1ccncc1-c1nc(cs1)C1CCCCC1 MOPJAYOZSLXMBK-UHFFFAOYSA-N 0.000 description 1
- WLVQDVQMYCNRLL-UHFFFAOYSA-N 4-cyclohexyl-2-[4-(2-methylpropyl)pyridin-3-yl]-1,3-thiazole Chemical compound CC(C)CC1=CC=NC=C1C1=NC(C2CCCCC2)=CS1 WLVQDVQMYCNRLL-UHFFFAOYSA-N 0.000 description 1
- NHTNWJSGVHLQLF-UHFFFAOYSA-N 4-cyclohexyl-2-isoquinolin-4-yl-1,3-thiazole Chemical compound C1CCCCC1C1=CSC(C=2C3=CC=CC=C3C=NC=2)=N1 NHTNWJSGVHLQLF-UHFFFAOYSA-N 0.000 description 1
- RYGKBAMTPAOQAR-UHFFFAOYSA-N 4-cyclohexyl-5-iodo-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C2CCCCC2)=C(I)S1 RYGKBAMTPAOQAR-UHFFFAOYSA-N 0.000 description 1
- MUPUPWUUARKCDT-UHFFFAOYSA-N 4-cyclohexyloxy-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(OC2CCCCC2)=CS1 MUPUPWUUARKCDT-UHFFFAOYSA-N 0.000 description 1
- KOSDKJRRLFBTIC-UHFFFAOYSA-N 4-cyclohexyloxy-2-pyridin-3-yl-1,3-thiazole Chemical compound C1CCCCC1OC1=CSC(C=2C=NC=CC=2)=N1 KOSDKJRRLFBTIC-UHFFFAOYSA-N 0.000 description 1
- LQFIKWBKMOZIQS-UHFFFAOYSA-N 4-cyclopentyl-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C2CCCC2)=CS1 LQFIKWBKMOZIQS-UHFFFAOYSA-N 0.000 description 1
- JZQYKIOOFOGSSM-UHFFFAOYSA-N 4-cyclopentyl-2-pyridin-3-yl-1,3-thiazole Chemical compound C1CCCC1C1=CSC(C=2C=NC=CC=2)=N1 JZQYKIOOFOGSSM-UHFFFAOYSA-N 0.000 description 1
- GZRIFLAOEMIUQK-UHFFFAOYSA-N 4-cyclopentyloxy-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(OC2CCCC2)=CS1 GZRIFLAOEMIUQK-UHFFFAOYSA-N 0.000 description 1
- ZBUOSHGUFNYSOF-UHFFFAOYSA-N 4-cyclopentyloxy-2-pyridin-3-yl-1,3-thiazole Chemical compound C1CCCC1OC1=CSC(C=2C=NC=CC=2)=N1 ZBUOSHGUFNYSOF-UHFFFAOYSA-N 0.000 description 1
- UBXZYCZPJMABQC-UHFFFAOYSA-N 4-ethoxy-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CCOC1=CSC(C=2C(=CC=NC=2)C)=N1 UBXZYCZPJMABQC-UHFFFAOYSA-N 0.000 description 1
- LRZGKOHFLNTIDC-UHFFFAOYSA-N 4-ethyl-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CCC1=CSC(C=2C(=CC=NC=2)C)=N1 LRZGKOHFLNTIDC-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- IWYYIZOHWPCALJ-UHFFFAOYSA-N 4-methyl-1-oxidopyridin-1-ium Chemical class CC1=CC=[N+]([O-])C=C1 IWYYIZOHWPCALJ-UHFFFAOYSA-N 0.000 description 1
- ZSWLATGNZVQPBQ-UHFFFAOYSA-N 4-naphthalen-2-yl-2-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C=C3C=CC=CC3=CC=2)=CS1 ZSWLATGNZVQPBQ-UHFFFAOYSA-N 0.000 description 1
- YWINFHCFHYFOSW-UHFFFAOYSA-N 4-phenyl-2-(4-phenylpyridin-3-yl)-1,3-thiazole Chemical compound C=1SC(C=2C(=CC=NC=2)C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 YWINFHCFHYFOSW-UHFFFAOYSA-N 0.000 description 1
- XRGSVHRRVNBUDY-UHFFFAOYSA-N 4-phenyl-2-(4-propan-2-ylpyridin-3-yl)-1,3-thiazole Chemical compound CC(C)C1=CC=NC=C1C1=NC(C=2C=CC=CC=2)=CS1 XRGSVHRRVNBUDY-UHFFFAOYSA-N 0.000 description 1
- SRQFJYYXWSHIDI-UHFFFAOYSA-N 4-phenyl-2-(4-propylpyridin-3-yl)-1,3-thiazole Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C=CC=CC=2)=CS1 SRQFJYYXWSHIDI-UHFFFAOYSA-N 0.000 description 1
- JSTXXXRMVFENFJ-UHFFFAOYSA-N 4-phenyl-2-(pyridin-3-ylmethyl)-1,3-thiazole Chemical compound C=1C=CN=CC=1CC(SC=1)=NC=1C1=CC=CC=C1 JSTXXXRMVFENFJ-UHFFFAOYSA-N 0.000 description 1
- ZENSHTJVIAQPGF-UHFFFAOYSA-N 4-phenyl-2-pyridin-3-yl-5,6,7,8-tetrahydro-4h-cyclohepta[d][1,3]thiazole Chemical compound C1CCCC=2SC(C=3C=NC=CC=3)=NC=2C1C1=CC=CC=C1 ZENSHTJVIAQPGF-UHFFFAOYSA-N 0.000 description 1
- PKZPWACKLTVWDD-UHFFFAOYSA-N 4-propan-2-yloxy-2-(4-propan-2-ylpyridin-3-yl)-1,3-thiazole Chemical compound CC(C)Oc1csc(n1)-c1cnccc1C(C)C PKZPWACKLTVWDD-UHFFFAOYSA-N 0.000 description 1
- XLQBMMUUFXNNBL-UHFFFAOYSA-N 4-propan-2-yloxy-2-pyridin-3-yl-1,3-thiazole Chemical compound CC(C)OC1=CSC(C=2C=NC=CC=2)=N1 XLQBMMUUFXNNBL-UHFFFAOYSA-N 0.000 description 1
- IPVKCSWBEAVSRO-UHFFFAOYSA-N 4-propan-2-ylpyridine-3-carbonitrile Chemical compound CC(C)C1=CC=NC=C1C#N IPVKCSWBEAVSRO-UHFFFAOYSA-N 0.000 description 1
- XOHZQGAYUHOJPR-UHFFFAOYSA-N 4-pyridin-3-yl-1,3-thiazol-2-amine Chemical class S1C(N)=NC(C=2C=NC=CC=2)=C1 XOHZQGAYUHOJPR-UHFFFAOYSA-N 0.000 description 1
- VXEOKTUEFNDTNE-UHFFFAOYSA-N 4-pyridin-3-yl-2-thiophen-2-yl-1,3-thiazole Chemical compound C1=CSC(C=2SC=C(N=2)C=2C=NC=CC=2)=C1 VXEOKTUEFNDTNE-UHFFFAOYSA-N 0.000 description 1
- XDPXUIMUDLLFLG-UHFFFAOYSA-N 4-tert-butyl-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C(C)(C)C)=CS1 XDPXUIMUDLLFLG-UHFFFAOYSA-N 0.000 description 1
- GXJZPBSOULCSGK-UHFFFAOYSA-N 4-tert-butyl-2-pyridin-3-yl-1,3-thiazole Chemical compound CC(C)(C)C1=CSC(C=2C=NC=CC=2)=N1 GXJZPBSOULCSGK-UHFFFAOYSA-N 0.000 description 1
- ZJDQDUMPOPOFSR-UHFFFAOYSA-N 4-tert-butylpyridine-3-carbonitrile Chemical compound CC(C)(C)C1=CC=NC=C1C#N ZJDQDUMPOPOFSR-UHFFFAOYSA-N 0.000 description 1
- YXMSAZOADQZOGU-UHFFFAOYSA-N 5-(4-methylphenyl)sulfonyl-2-pyridin-3-yl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CC(SC(=N2)C=3C=NC=CC=3)=C2CC1 YXMSAZOADQZOGU-UHFFFAOYSA-N 0.000 description 1
- ZVTSKYKLJJXZEP-UHFFFAOYSA-N 5-[2-(4-cyclopropylpyridin-3-yl)-1,3-thiazol-4-yl]-3-(3,4-dichlorophenyl)-1,2-oxazole Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=NOC(C=2N=C(SC=2)C=2C(=CC=NC=2)C2CC2)=C1 ZVTSKYKLJJXZEP-UHFFFAOYSA-N 0.000 description 1
- KNHOJPNMTKDSRU-UHFFFAOYSA-N 5-[2-(4-methylpyridin-3-yl)-1,3-thiazol-4-yl]thiophene-2-carbonitrile Chemical compound CC1=CC=NC=C1C1=NC(C=2SC(=CC=2)C#N)=CS1 KNHOJPNMTKDSRU-UHFFFAOYSA-N 0.000 description 1
- ZOELZYKJENPRRC-UHFFFAOYSA-N 5-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]-1,2-oxazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2ON=CC=2)=N1 ZOELZYKJENPRRC-UHFFFAOYSA-N 0.000 description 1
- ZNNXQYBTQJMFPQ-UHFFFAOYSA-N 5-chloro-2-(4-chlorophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=C(Cl)SC(C=2C=CC(Cl)=CC=2)=N1 ZNNXQYBTQJMFPQ-UHFFFAOYSA-N 0.000 description 1
- WTVNIKWEXCEDCD-UHFFFAOYSA-N 5-methyl-3-phenyl-4-[2-(4-propylpyridin-3-yl)-1,3-thiazol-4-yl]-1,2-oxazole Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C(=NOC=2C)C=2C=CC=CC=2)=CS1 WTVNIKWEXCEDCD-UHFFFAOYSA-N 0.000 description 1
- GSGOCLDRTHODPU-UHFFFAOYSA-N 5-methyl-4-phenyl-2-pyridin-3-yl-1,3-thiazole Chemical compound CC=1SC(C=2C=NC=CC=2)=NC=1C1=CC=CC=C1 GSGOCLDRTHODPU-UHFFFAOYSA-N 0.000 description 1
- AVHGWTWZXIHDIM-UHFFFAOYSA-N 5-methyl-n-phenyl-2-pyridin-3-yl-1,3-thiazol-4-amine Chemical compound CC=1SC(C=2C=NC=CC=2)=NC=1NC1=CC=CC=C1 AVHGWTWZXIHDIM-UHFFFAOYSA-N 0.000 description 1
- CVYKPNSVMFGNRF-UHFFFAOYSA-N 6-(2-pyridin-3-yl-1,3-thiazol-4-yl)-4h-1,4-benzoxazin-3-one Chemical compound C1=C2NC(=O)COC2=CC=C1C(N=1)=CSC=1C1=CC=CN=C1 CVYKPNSVMFGNRF-UHFFFAOYSA-N 0.000 description 1
- DYTLZAQCUUBOSH-UHFFFAOYSA-N 6-[2-(4-methylpyridin-3-yl)-1,3-thiazol-4-yl]-3,4-dihydro-1h-quinolin-2-one Chemical compound CC1=CC=NC=C1C1=NC(C=2C=C3CCC(=O)NC3=CC=2)=CS1 DYTLZAQCUUBOSH-UHFFFAOYSA-N 0.000 description 1
- JYTFNDMTVYHPJN-UHFFFAOYSA-N 6-methyl-2-pyridin-3-yl-4,7-dihydro-[1,3]thiazolo[4,5-d]pyrimidin-5-one Chemical compound N=1C=2NC(=O)N(C)CC=2SC=1C1=CC=CN=C1 JYTFNDMTVYHPJN-UHFFFAOYSA-N 0.000 description 1
- BXIPAWXJNJVUSC-UHFFFAOYSA-N 7-methoxy-2-pyridin-3-yl-4,5-dihydrobenzo[e][1,3]benzothiazole Chemical compound S1C=2CCC3=CC(OC)=CC=C3C=2N=C1C1=CC=CN=C1 BXIPAWXJNJVUSC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-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
- 208000005676 Adrenogenital syndrome Diseases 0.000 description 1
- 108700028369 Alleles Proteins 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
- 229940122815 Aromatase inhibitor Drugs 0.000 description 1
- 108010011485 Aspartame Proteins 0.000 description 1
- 241000416162 Astragalus gummifer Species 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
- IPUPDUKRKOITNM-UHFFFAOYSA-N C12(CC3CC(CC(C1)C3)C2)C=2N=C(SC2)C=2C=NC=CC2C(C)C Chemical compound C12(CC3CC(CC(C1)C3)C2)C=2N=C(SC2)C=2C=NC=CC2C(C)C IPUPDUKRKOITNM-UHFFFAOYSA-N 0.000 description 1
- YJESRHGVUWDZAZ-UHFFFAOYSA-N C1=CC(C)=CC=C1C1=NC(C=2C(=CC=NC=2)C2CC2)=CS1 Chemical compound C1=CC(C)=CC=C1C1=NC(C=2C(=CC=NC=2)C2CC2)=CS1 YJESRHGVUWDZAZ-UHFFFAOYSA-N 0.000 description 1
- NTGXTKPHMPSOIN-UHFFFAOYSA-N C1=CC(Cl)=CC=C1C1=NC(C=2C(=CC=NC=2)C2CC2)=CS1 Chemical compound C1=CC(Cl)=CC=C1C1=NC(C=2C(=CC=NC=2)C2CC2)=CS1 NTGXTKPHMPSOIN-UHFFFAOYSA-N 0.000 description 1
- HYIKOZMTQFWTLP-UHFFFAOYSA-N C1=CC([N+](=O)[O-])=CC=C1C1=NC(C=2C(=CC=NC=2)C2CC2)=CS1 Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=NC(C=2C(=CC=NC=2)C2CC2)=CS1 HYIKOZMTQFWTLP-UHFFFAOYSA-N 0.000 description 1
- QNIVBNUTOWDZRG-UHFFFAOYSA-N C1=NC(C)=CC=C1C1=NC(C=2C(=CC=NC=2)C2CC2)=CS1 Chemical compound C1=NC(C)=CC=C1C1=NC(C=2C(=CC=NC=2)C2CC2)=CS1 QNIVBNUTOWDZRG-UHFFFAOYSA-N 0.000 description 1
- GUEOEVCEFJKDAX-UHFFFAOYSA-N C1CC1C1=CC=NC=C1C1=CSC(C=2C=CC=CC=2)=N1 Chemical compound C1CC1C1=CC=NC=C1C1=CSC(C=2C=CC=CC=2)=N1 GUEOEVCEFJKDAX-UHFFFAOYSA-N 0.000 description 1
- PDADHUGGJZCOIP-UHFFFAOYSA-N CC(C)C1=C(C=NC=C1)C=1SC=C(N1)C1=CC=C(C=C1)N1CCCC1 Chemical compound CC(C)C1=C(C=NC=C1)C=1SC=C(N1)C1=CC=C(C=C1)N1CCCC1 PDADHUGGJZCOIP-UHFFFAOYSA-N 0.000 description 1
- SZZJSGZWMRKSME-UHFFFAOYSA-N CC(C)Oc1csc(n1)-c1cnccc1C Chemical compound CC(C)Oc1csc(n1)-c1cnccc1C SZZJSGZWMRKSME-UHFFFAOYSA-N 0.000 description 1
- WYNVSQBMQRYDRB-UHFFFAOYSA-N CC(C)c1ccncc1-c1csc(n1)-c1cc(Cl)nc(Cl)c1 Chemical compound CC(C)c1ccncc1-c1csc(n1)-c1cc(Cl)nc(Cl)c1 WYNVSQBMQRYDRB-UHFFFAOYSA-N 0.000 description 1
- LPPZUQKMQIXLFV-UHFFFAOYSA-N CC(C)c1ccncc1-c1csc(n1)-c1ccc(C)cc1 Chemical compound CC(C)c1ccncc1-c1csc(n1)-c1ccc(C)cc1 LPPZUQKMQIXLFV-UHFFFAOYSA-N 0.000 description 1
- GYOOQOFWBKRLOO-UHFFFAOYSA-N CC(C)c1ccncc1-c1csc(n1)-c1ccc(C)nc1 Chemical compound CC(C)c1ccncc1-c1csc(n1)-c1ccc(C)nc1 GYOOQOFWBKRLOO-UHFFFAOYSA-N 0.000 description 1
- MMDBYAYOQDSPDS-UHFFFAOYSA-N CC(C)c1ccncc1-c1csc(n1)-c1ccc(Cl)cc1 Chemical compound CC(C)c1ccncc1-c1csc(n1)-c1ccc(Cl)cc1 MMDBYAYOQDSPDS-UHFFFAOYSA-N 0.000 description 1
- GIIWAVFSDKFOIG-UHFFFAOYSA-N CC(C)c1ccncc1-c1csc(n1)-c1cccc(Cl)c1 Chemical compound CC(C)c1ccncc1-c1csc(n1)-c1cccc(Cl)c1 GIIWAVFSDKFOIG-UHFFFAOYSA-N 0.000 description 1
- GMYOTXBFEHFRFY-UHFFFAOYSA-N CC(C)c1ccncc1-c1csc(n1)-c1ccccc1 Chemical compound CC(C)c1ccncc1-c1csc(n1)-c1ccccc1 GMYOTXBFEHFRFY-UHFFFAOYSA-N 0.000 description 1
- AMMJYAHFJAGJIO-UHFFFAOYSA-N CC(C)c1ccncc1-c1csc(n1)-c1nccc2ccccc12 Chemical compound CC(C)c1ccncc1-c1csc(n1)-c1nccc2ccccc12 AMMJYAHFJAGJIO-UHFFFAOYSA-N 0.000 description 1
- QMJLSRZOBKTKAJ-UHFFFAOYSA-N CC(C)c1ccncc1-c1nc(Cc2ccc(Cl)cc2)cs1 Chemical compound CC(C)c1ccncc1-c1nc(Cc2ccc(Cl)cc2)cs1 QMJLSRZOBKTKAJ-UHFFFAOYSA-N 0.000 description 1
- AWQHVSRXJAAXRQ-UHFFFAOYSA-N CC(C)c1ccncc1-c1nc(c(C)s1)-c1ccc(Cl)cc1 Chemical compound CC(C)c1ccncc1-c1nc(c(C)s1)-c1ccc(Cl)cc1 AWQHVSRXJAAXRQ-UHFFFAOYSA-N 0.000 description 1
- HJIAHWHMQKNXCB-UHFFFAOYSA-N CC(C)c1ccncc1-c1nc(cs1)-c1ccc(C)cc1 Chemical compound CC(C)c1ccncc1-c1nc(cs1)-c1ccc(C)cc1 HJIAHWHMQKNXCB-UHFFFAOYSA-N 0.000 description 1
- DQKBWVVMTQSUBA-UHFFFAOYSA-N CC(C)c1ccncc1-c1nc(cs1)-c1ccc(cc1)-c1ccccc1 Chemical compound CC(C)c1ccncc1-c1nc(cs1)-c1ccc(cc1)-c1ccccc1 DQKBWVVMTQSUBA-UHFFFAOYSA-N 0.000 description 1
- NYOHLQCTBYVMSP-UHFFFAOYSA-N CC(C)c1ccncc1-c1nc(cs1)-c1ccc(cc1)[N+]([O-])=O Chemical compound CC(C)c1ccncc1-c1nc(cs1)-c1ccc(cc1)[N+]([O-])=O NYOHLQCTBYVMSP-UHFFFAOYSA-N 0.000 description 1
- CXGVCQUPDAIYSL-UHFFFAOYSA-N CC(C)c1ccncc1-c1nc(cs1)-c1ccc2ccccc2c1 Chemical compound CC(C)c1ccncc1-c1nc(cs1)-c1ccc2ccccc2c1 CXGVCQUPDAIYSL-UHFFFAOYSA-N 0.000 description 1
- COIBQDXFQZJOQU-UHFFFAOYSA-N CC(C)c1ccncc1-c1nc(cs1)-c1cccc(Cl)c1 Chemical compound CC(C)c1ccncc1-c1nc(cs1)-c1cccc(Cl)c1 COIBQDXFQZJOQU-UHFFFAOYSA-N 0.000 description 1
- ZQOLHBVUDXMQLW-UHFFFAOYSA-N CC(C)c1ccncc1-c1nc(cs1)-c1cccc(OC(=O)c2ccccc2)c1 Chemical compound CC(C)c1ccncc1-c1nc(cs1)-c1cccc(OC(=O)c2ccccc2)c1 ZQOLHBVUDXMQLW-UHFFFAOYSA-N 0.000 description 1
- ZPSLVPBIJRMYCX-UHFFFAOYSA-N CC(C)c1ccncc1-c1nc(cs1)-c1ccccc1F Chemical compound CC(C)c1ccncc1-c1nc(cs1)-c1ccccc1F ZPSLVPBIJRMYCX-UHFFFAOYSA-N 0.000 description 1
- XYDMSAYOSYAAFB-UHFFFAOYSA-N CC(C)c1ccncc1-c1nc(cs1)-c1cccnc1 Chemical compound CC(C)c1ccncc1-c1nc(cs1)-c1cccnc1 XYDMSAYOSYAAFB-UHFFFAOYSA-N 0.000 description 1
- YJNDKCRTYKNJGJ-UHFFFAOYSA-N CC(C)c1ccncc1-c1nc(cs1)C1CCCCCC1 Chemical compound CC(C)c1ccncc1-c1nc(cs1)C1CCCCCC1 YJNDKCRTYKNJGJ-UHFFFAOYSA-N 0.000 description 1
- LILSCEIZMFOYRV-UHFFFAOYSA-N CC1=CC=NC=C1C1=CSC(C=2C=C(C=CC=2)C#N)=N1 Chemical compound CC1=CC=NC=C1C1=CSC(C=2C=C(C=CC=2)C#N)=N1 LILSCEIZMFOYRV-UHFFFAOYSA-N 0.000 description 1
- AMDVTVRSYXAKEY-UHFFFAOYSA-N CC1=CC=NC=C1C1=CSC(NC=2C=CC(=CC=2)C(O)=O)=N1 Chemical compound CC1=CC=NC=C1C1=CSC(NC=2C=CC(=CC=2)C(O)=O)=N1 AMDVTVRSYXAKEY-UHFFFAOYSA-N 0.000 description 1
- USYRYTTZOUWDSG-UHFFFAOYSA-N CC1=CC=NC=C1C1=NC(C(=O)NC=2C=CN=CC=2)=CS1 Chemical compound CC1=CC=NC=C1C1=NC(C(=O)NC=2C=CN=CC=2)=CS1 USYRYTTZOUWDSG-UHFFFAOYSA-N 0.000 description 1
- LVQNIGASSTUTJB-UHFFFAOYSA-N CC1=CC=NC=C1C1=NC(C(=O)NC=2C=NC=CC=2)=CS1 Chemical compound CC1=CC=NC=C1C1=NC(C(=O)NC=2C=NC=CC=2)=CS1 LVQNIGASSTUTJB-UHFFFAOYSA-N 0.000 description 1
- LPGVAVDXXYQMGA-UHFFFAOYSA-N CC1=CC=NC=C1C1=NC(C(=O)NN2CCCCC2)=CS1 Chemical compound CC1=CC=NC=C1C1=NC(C(=O)NN2CCCCC2)=CS1 LPGVAVDXXYQMGA-UHFFFAOYSA-N 0.000 description 1
- BKOYSSRCUHKIPQ-UHFFFAOYSA-N CC1=CC=NC=C1C1=NC(C2=C(C=CS2)Br)=CS1 Chemical compound CC1=CC=NC=C1C1=NC(C2=C(C=CS2)Br)=CS1 BKOYSSRCUHKIPQ-UHFFFAOYSA-N 0.000 description 1
- NOKNTOVDGCRBDJ-UHFFFAOYSA-N CC1=CC=NC=C1C1=NC(C2=C(C=CS2)Cl)=CS1 Chemical compound CC1=CC=NC=C1C1=NC(C2=C(C=CS2)Cl)=CS1 NOKNTOVDGCRBDJ-UHFFFAOYSA-N 0.000 description 1
- WOQUNNXVRJRMBV-UHFFFAOYSA-N CCC1=CC=NC=C1C1=CSC(C=2C=C(C=CC=2)C#N)=N1 Chemical compound CCC1=CC=NC=C1C1=CSC(C=2C=C(C=CC=2)C#N)=N1 WOQUNNXVRJRMBV-UHFFFAOYSA-N 0.000 description 1
- LTSBAIOOVKHLPB-UHFFFAOYSA-N CCC1=CC=NC=C1C1=CSC(C=2C=C(C=CC=2)[N+]([O-])=O)=N1 Chemical compound CCC1=CC=NC=C1C1=CSC(C=2C=C(C=CC=2)[N+]([O-])=O)=N1 LTSBAIOOVKHLPB-UHFFFAOYSA-N 0.000 description 1
- VPXBZVKHPWECHS-UHFFFAOYSA-N CCC1=CC=NC=C1C1=CSC(C=2C=C(Cl)C=CC=2)=N1 Chemical compound CCC1=CC=NC=C1C1=CSC(C=2C=C(Cl)C=CC=2)=N1 VPXBZVKHPWECHS-UHFFFAOYSA-N 0.000 description 1
- XPDYPHCIVURXIN-UHFFFAOYSA-N CCC1=CC=NC=C1C1=CSC(C=2C=CC(=CC=2)C(F)(F)F)=N1 Chemical compound CCC1=CC=NC=C1C1=CSC(C=2C=CC(=CC=2)C(F)(F)F)=N1 XPDYPHCIVURXIN-UHFFFAOYSA-N 0.000 description 1
- AGPCALDRLCPILV-UHFFFAOYSA-N CCC1=CC=NC=C1C1=CSC(C=2C=CC(=CC=2)[N+]([O-])=O)=N1 Chemical compound CCC1=CC=NC=C1C1=CSC(C=2C=CC(=CC=2)[N+]([O-])=O)=N1 AGPCALDRLCPILV-UHFFFAOYSA-N 0.000 description 1
- HQVODJKCDKMYSM-UHFFFAOYSA-N CCC1=CC=NC=C1C1=CSC(C=2C=CC(Cl)=CC=2)=N1 Chemical compound CCC1=CC=NC=C1C1=CSC(C=2C=CC(Cl)=CC=2)=N1 HQVODJKCDKMYSM-UHFFFAOYSA-N 0.000 description 1
- AQRSBHYTECOATM-UHFFFAOYSA-N CCC1=CC=NC=C1C1=CSC(C=2C=NC(C)=CC=2)=N1 Chemical compound CCC1=CC=NC=C1C1=CSC(C=2C=NC(C)=CC=2)=N1 AQRSBHYTECOATM-UHFFFAOYSA-N 0.000 description 1
- ZZADHAZWCCIHTE-UHFFFAOYSA-N COC1=CC=CC=C1C1=CSC(C=2C(=CC=NC=2)C)=N1 Chemical compound COC1=CC=CC=C1C1=CSC(C=2C(=CC=NC=2)C)=N1 ZZADHAZWCCIHTE-UHFFFAOYSA-N 0.000 description 1
- DHIBVVUYKQHBDB-UHFFFAOYSA-N CSc1cccc(Nc2nc(cs2)-c2cnccc2C)c1 Chemical compound CSc1cccc(Nc2nc(cs2)-c2cnccc2C)c1 DHIBVVUYKQHBDB-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- MAFSDRFXTVDMOL-UHFFFAOYSA-N Cc1ccncc1-c1csc(NCCC2CCCCN2)n1 Chemical compound Cc1ccncc1-c1csc(NCCC2CCCCN2)n1 MAFSDRFXTVDMOL-UHFFFAOYSA-N 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
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- KTIZYYMJILBGFV-UHFFFAOYSA-N ClC1=CC=CC(C=2SC=C(N=2)C=2C(=CC=NC=2)C2CC2)=C1 Chemical compound ClC1=CC=CC(C=2SC=C(N=2)C=2C(=CC=NC=2)C2CC2)=C1 KTIZYYMJILBGFV-UHFFFAOYSA-N 0.000 description 1
- MTNZUSCRXXVDAJ-UHFFFAOYSA-N Clc1ccc(cc1)-c1csc(n1)-c1cccnc1C1CCNCC1 Chemical compound Clc1ccc(cc1)-c1csc(n1)-c1cccnc1C1CCNCC1 MTNZUSCRXXVDAJ-UHFFFAOYSA-N 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
- 108010092160 Dactinomycin Proteins 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 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
- 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
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-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
- 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
- 239000007818 Grignard reagent Substances 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
- 101150026303 HEX1 gene Proteins 0.000 description 1
- 101000904173 Homo sapiens Progonadoliberin-1 Proteins 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 206010020571 Hyperaldosteronism Diseases 0.000 description 1
- 206010061218 Inflammation 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
- 229930126263 Maytansine Natural products 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
- SKENSLWKHUBTLT-UHFFFAOYSA-N N',N'-dimethyl-N-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]propane-1,3-diamine Chemical compound CN(C)CCCNc1nc(cs1)-c1cnccc1C SKENSLWKHUBTLT-UHFFFAOYSA-N 0.000 description 1
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 1
- WPOQYCVBCTXAPH-UHFFFAOYSA-N N-(2-bicyclo[2.2.1]heptanyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole-4-carboxamide Chemical compound Cc1ccncc1-c1nc(cs1)C(=O)NC1CC2CCC1C2 WPOQYCVBCTXAPH-UHFFFAOYSA-N 0.000 description 1
- CGFSHWLARWALLW-UHFFFAOYSA-N N-(3,4-difluorophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole-4-carboxamide Chemical compound Cc1ccncc1-c1nc(cs1)C(=O)Nc1ccc(F)c(F)c1 CGFSHWLARWALLW-UHFFFAOYSA-N 0.000 description 1
- HWJCUXZVYLQWHV-UHFFFAOYSA-N N-(3-chloro-4-fluorophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole-4-carboxamide Chemical compound Cc1ccncc1-c1nc(cs1)C(=O)Nc1ccc(F)c(Cl)c1 HWJCUXZVYLQWHV-UHFFFAOYSA-N 0.000 description 1
- PUJRJPRMGNQBBA-UHFFFAOYSA-N N-(3-cyanophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole-4-carboxamide Chemical compound Cc1ccncc1-c1nc(cs1)C(=O)Nc1cccc(c1)C#N PUJRJPRMGNQBBA-UHFFFAOYSA-N 0.000 description 1
- OLHCGKYBODGFLR-UHFFFAOYSA-N N-(4-chloro-2-methoxyphenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound COc1cc(Cl)ccc1Nc1nc(cs1)-c1cnccc1C OLHCGKYBODGFLR-UHFFFAOYSA-N 0.000 description 1
- WZSMSEWEVYYZGN-UHFFFAOYSA-N N-(4-chlorophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole-4-carboxamide Chemical compound Cc1ccncc1-c1nc(cs1)C(=O)Nc1ccc(Cl)cc1 WZSMSEWEVYYZGN-UHFFFAOYSA-N 0.000 description 1
- HJVOPCRFDJYETF-UHFFFAOYSA-N N-(4-fluorophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole-4-carboxamide Chemical compound Cc1ccncc1-c1nc(cs1)C(=O)Nc1ccc(F)cc1 HJVOPCRFDJYETF-UHFFFAOYSA-N 0.000 description 1
- AWJXLVZVPOXYIN-UHFFFAOYSA-N N-(4-methoxyphenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole-4-carboxamide Chemical compound COc1ccc(NC(=O)c2csc(n2)-c2cnccc2C)cc1 AWJXLVZVPOXYIN-UHFFFAOYSA-N 0.000 description 1
- GXFPZEYMRNIDBO-UHFFFAOYSA-N N-(4-methylphenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole-4-carboxamide Chemical compound CC1=C(C=NC=C1)C=1SC=C(N1)C(=O)NC1=CC=C(C=C1)C GXFPZEYMRNIDBO-UHFFFAOYSA-N 0.000 description 1
- NFUOXYNMAUHPBO-UHFFFAOYSA-N N-(5-fluoro-2-methylphenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound Cc1ccc(F)cc1Nc1nc(cs1)-c1cnccc1C NFUOXYNMAUHPBO-UHFFFAOYSA-N 0.000 description 1
- NVEPDNJZZOHOLG-UHFFFAOYSA-N N-(furan-2-ylmethyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole-4-carboxamide Chemical compound Cc1ccncc1-c1nc(cs1)C(=O)NCc1ccco1 NVEPDNJZZOHOLG-UHFFFAOYSA-N 0.000 description 1
- ROUZIVRMEHJHJH-UHFFFAOYSA-N N-[(4-methylphenyl)methyl]-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound Cc1ccc(CNc2nc(cs2)-c2cnccc2C)cc1 ROUZIVRMEHJHJH-UHFFFAOYSA-N 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
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 102000007399 Nuclear hormone receptor Human genes 0.000 description 1
- 108020005497 Nuclear hormone receptor Proteins 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
- 208000001132 Osteoporosis Diseases 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229910019213 POCl3 Inorganic materials 0.000 description 1
- 229930012538 Paclitaxel Natural products 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 102100024028 Progonadoliberin-1 Human genes 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229940123934 Reductase inhibitor Drugs 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
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 101000996723 Sus scrofa Gonadotropin-releasing hormone receptor Proteins 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229940122803 Vinca alkaloid Drugs 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- SZUPASKJNOUBRJ-UHFFFAOYSA-N [2-(4-methylpyridin-3-yl)-1,3-thiazol-4-yl]-morpholin-4-ylmethanone Chemical compound CC1=CC=NC=C1C1=NC(C(=O)N2CCOCC2)=CS1 SZUPASKJNOUBRJ-UHFFFAOYSA-N 0.000 description 1
- PYVKUPJYTSOFJX-UHFFFAOYSA-N [3-(2-pyridin-3-yl-1,3-thiazol-4-yl)phenyl] benzoate Chemical compound C=1C=CC=CC=1C(=O)OC(C=1)=CC=CC=1C(N=1)=CSC=1C1=CC=CN=C1 PYVKUPJYTSOFJX-UHFFFAOYSA-N 0.000 description 1
- TVWPAWLLEYZGJQ-UHFFFAOYSA-N [3-[2-(4-propylpyridin-3-yl)-1,3-thiazol-4-yl]phenyl] benzoate Chemical compound CCCC1=CC=NC=C1C1=NC(C=2C=C(OC(=O)C=3C=CC=CC=3)C=CC=2)=CS1 TVWPAWLLEYZGJQ-UHFFFAOYSA-N 0.000 description 1
- IEOZSQUSEVDNPJ-UHFFFAOYSA-N [O-][N+](=O)C1=CC=CC(C=2SC=C(N=2)C=2C(=CC=NC=2)C2CC2)=C1 Chemical compound [O-][N+](=O)C1=CC=CC(C=2SC=C(N=2)C=2C(=CC=NC=2)C2CC2)=C1 IEOZSQUSEVDNPJ-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
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes 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
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229940087168 alpha tocopherol Drugs 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
- 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
- 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
- 229910052786 argon Inorganic materials 0.000 description 1
- 229940046844 aromatase inhibitors Drugs 0.000 description 1
- 238000007262 aromatic hydroxylation reaction Methods 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 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
- 125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 description 1
- JHVLLYQQQYIWKX-UHFFFAOYSA-N benzyl 2-bromoacetate Chemical compound BrCC(=O)OCC1=CC=CC=C1 JHVLLYQQQYIWKX-UHFFFAOYSA-N 0.000 description 1
- SXFPXZSENHPCSH-UHFFFAOYSA-N bicyclo[3.2.1]octan-4-one Chemical compound O=C1CCC2CCC1C2 SXFPXZSENHPCSH-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000010256 biochemical assay Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000000090 biomarker Substances 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 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
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000000423 cell based assay Methods 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
- 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
- 238000000451 chemical ionisation Methods 0.000 description 1
- 238000002512 chemotherapy Methods 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
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 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
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 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
- 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
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000003748 differential diagnosis Methods 0.000 description 1
- JMRYOSQOYJBDOI-UHFFFAOYSA-N dilithium;di(propan-2-yl)azanide Chemical compound [Li+].CC(C)[N-]C(C)C.CC(C)N([Li])C(C)C JMRYOSQOYJBDOI-UHFFFAOYSA-N 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 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
- 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
- 230000002500 effect on skin Effects 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
- 230000007613 environmental effect Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 229930182833 estradiol Natural products 0.000 description 1
- 239000000328 estrogen antagonist Substances 0.000 description 1
- LHWWETDBWVTKJO-UHFFFAOYSA-N et3n triethylamine Chemical compound CCN(CC)CC.CCN(CC)CC LHWWETDBWVTKJO-UHFFFAOYSA-N 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- AHCNNBKHLMWBSW-UHFFFAOYSA-N ethyl 3-[[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]amino]benzoate Chemical compound CCOC(=O)C1=CC=CC(NC=2SC=C(N=2)C=2C(=CC=NC=2)C)=C1 AHCNNBKHLMWBSW-UHFFFAOYSA-N 0.000 description 1
- ZUQHANXDCGHENH-UHFFFAOYSA-N ethyl 3-methyl-3-(2-pyridin-3-yl-1,3-thiazol-4-yl)butanoate Chemical compound CCOC(=O)CC(C)(C)C1=CSC(C=2C=NC=CC=2)=N1 ZUQHANXDCGHENH-UHFFFAOYSA-N 0.000 description 1
- KQWWVLVLVYYYDT-UHFFFAOYSA-N ethyl 3-oxohexanoate Chemical compound CCCC(=O)CC(=O)OCC KQWWVLVLVYYYDT-UHFFFAOYSA-N 0.000 description 1
- OJAGAAVUZKMVGX-UHFFFAOYSA-N ethyl acetate;pyridine Chemical compound CCOC(C)=O.C1=CC=NC=C1 OJAGAAVUZKMVGX-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 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
- 238000009093 first-line therapy Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 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
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000004110 gluconeogenesis Effects 0.000 description 1
- 230000023611 glucuronidation Effects 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
- 150000004795 grignard reagents Chemical class 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
- 150000002390 heteroarenes Chemical class 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
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229940125697 hormonal agent Drugs 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 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
- 229960002899 hydroxyprogesterone Drugs 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
- 239000003701 inert diluent Substances 0.000 description 1
- 230000004054 inflammatory process Effects 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
- 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 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-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
- 210000003734 kidney Anatomy 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
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000004571 lime Substances 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
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 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
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- UKZCGMDMXDLAGZ-UHFFFAOYSA-M magnesium;2-methylpropane;bromide Chemical group [Mg+2].[Br-].C[C-](C)C UKZCGMDMXDLAGZ-UHFFFAOYSA-M 0.000 description 1
- CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 1
- VFZXMEQGIIWBFJ-UHFFFAOYSA-M magnesium;cyclopropane;bromide Chemical compound [Mg+2].[Br-].C1C[CH-]1 VFZXMEQGIIWBFJ-UHFFFAOYSA-M 0.000 description 1
- LVKCSZQWLOVUGB-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].C[CH-]C LVKCSZQWLOVUGB-UHFFFAOYSA-M 0.000 description 1
- UGVPKMAWLOMPRS-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].CC[CH2-] UGVPKMAWLOMPRS-UHFFFAOYSA-M 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000001819 mass spectrum Methods 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
- 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
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000001923 methylcellulose Substances 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
- 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
- WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- ALYRKPAVLDBPLA-UHFFFAOYSA-N n,n-diethyl-2-pyridin-3-yl-1,3-thiazol-4-amine Chemical compound CCN(CC)C1=CSC(C=2C=NC=CC=2)=N1 ALYRKPAVLDBPLA-UHFFFAOYSA-N 0.000 description 1
- VGNAGVNZCCQOOQ-UHFFFAOYSA-N n,n-diethyl-3-[2-(4-methylpyridin-3-yl)-1,3-thiazol-4-yl]aniline Chemical compound CCN(CC)C1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C)=C1 VGNAGVNZCCQOOQ-UHFFFAOYSA-N 0.000 description 1
- IVZCTKILAOKDSP-UHFFFAOYSA-N n-(2,4-dichlorophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(NC=2C(=CC(Cl)=CC=2)Cl)=N1 IVZCTKILAOKDSP-UHFFFAOYSA-N 0.000 description 1
- ZLLJDYZFMBHPNJ-UHFFFAOYSA-N n-(2,4-difluorophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(NC=2C(=CC(F)=CC=2)F)=N1 ZLLJDYZFMBHPNJ-UHFFFAOYSA-N 0.000 description 1
- XRNVRFMAYANGHX-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound COC1=CC(OC)=CC=C1NC1=NC(C=2C(=CC=NC=2)C)=CS1 XRNVRFMAYANGHX-UHFFFAOYSA-N 0.000 description 1
- HNHCXGKLNLKOEE-UHFFFAOYSA-N n-(2-chlorophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(NC=2C(=CC=CC=2)Cl)=N1 HNHCXGKLNLKOEE-UHFFFAOYSA-N 0.000 description 1
- ZAZLGMAQDIEXQI-UHFFFAOYSA-N n-(2-methoxyphenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound COC1=CC=CC=C1NC1=NC(C=2C(=CC=NC=2)C)=CS1 ZAZLGMAQDIEXQI-UHFFFAOYSA-N 0.000 description 1
- ZRURXTWIPFLTPC-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-1,3-thiazol-4-amine Chemical compound ClC1=CC(Cl)=CC(NC=2N=CSC=2)=C1 ZRURXTWIPFLTPC-UHFFFAOYSA-N 0.000 description 1
- AWGVTOILQDWWJD-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazol-4-amine Chemical compound CC1=CC=NC=C1C1=NC(NC=2C=C(Cl)C=C(Cl)C=2)=CS1 AWGVTOILQDWWJD-UHFFFAOYSA-N 0.000 description 1
- NEJLWXMEAMIOBS-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(NC=2C=C(Cl)C=C(Cl)C=2)=N1 NEJLWXMEAMIOBS-UHFFFAOYSA-N 0.000 description 1
- VYEUUJSTJUHWBM-UHFFFAOYSA-N n-(3-chlorophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(NC=2C=C(Cl)C=CC=2)=N1 VYEUUJSTJUHWBM-UHFFFAOYSA-N 0.000 description 1
- JCXSTNPBWXSCGG-UHFFFAOYSA-N n-(3-fluorophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(NC=2C=C(F)C=CC=2)=N1 JCXSTNPBWXSCGG-UHFFFAOYSA-N 0.000 description 1
- JQIPWTDEIKQPAN-UHFFFAOYSA-N n-(3-methoxyphenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound COC1=CC=CC(NC=2SC=C(N=2)C=2C(=CC=NC=2)C)=C1 JQIPWTDEIKQPAN-UHFFFAOYSA-N 0.000 description 1
- IFKIAODJGNRFKM-UHFFFAOYSA-N n-(4-methylphenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound C1=CC(C)=CC=C1NC1=NC(C=2C(=CC=NC=2)C)=CS1 IFKIAODJGNRFKM-UHFFFAOYSA-N 0.000 description 1
- GXVYAOFJBBNONM-UHFFFAOYSA-N n-(cyclohexylmethyl)-2-(4-methylpyridin-3-yl)-1,3-thiazol-4-amine Chemical compound CC1=CC=NC=C1C1=NC(NCC2CCCCC2)=CS1 GXVYAOFJBBNONM-UHFFFAOYSA-N 0.000 description 1
- NSPAJSNZTSRTHF-UHFFFAOYSA-N n-(furan-2-ylmethyl)-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(NCC=2OC=CC=2)=N1 NSPAJSNZTSRTHF-UHFFFAOYSA-N 0.000 description 1
- XKGRUPJNQKOTNB-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(NCC=2C=CC(Cl)=CC=2)=N1 XKGRUPJNQKOTNB-UHFFFAOYSA-N 0.000 description 1
- ACBIETHCLMTIAA-UHFFFAOYSA-N n-benzhydryl-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(NC(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 ACBIETHCLMTIAA-UHFFFAOYSA-N 0.000 description 1
- DMWCTKNLQJAIQI-UHFFFAOYSA-N n-benzyl-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(NCC=2C=CC=CC=2)=N1 DMWCTKNLQJAIQI-UHFFFAOYSA-N 0.000 description 1
- PCXPFLTWKHCBTM-UHFFFAOYSA-N n-butyl-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound S1C(NCCCC)=NC(C=2C(=CC=NC=2)C)=C1 PCXPFLTWKHCBTM-UHFFFAOYSA-N 0.000 description 1
- DDERZJXMZYNLMQ-UHFFFAOYSA-N n-cyclohexyl-2-(4-methylpyridin-3-yl)-1,3-thiazole-4-carboxamide Chemical compound CC1=CC=NC=C1C1=NC(C(=O)NC2CCCCC2)=CS1 DDERZJXMZYNLMQ-UHFFFAOYSA-N 0.000 description 1
- QJHHOVPYPLXVLT-UHFFFAOYSA-N n-cyclohexyl-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-amine Chemical compound CC1=CC=NC=C1C1=CSC(NC2CCCCC2)=N1 QJHHOVPYPLXVLT-UHFFFAOYSA-N 0.000 description 1
- VEYVUYVHENCWPE-UHFFFAOYSA-N n-cyclohexyl-n-methyl-2-(4-methylpyridin-3-yl)-1,3-thiazol-4-amine Chemical compound C=1SC(C=2C(=CC=NC=2)C)=NC=1N(C)C1CCCCC1 VEYVUYVHENCWPE-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 201000004931 neurofibromatosis Diseases 0.000 description 1
- 150000002826 nitrites Chemical class 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
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- GYCKQBWUSACYIF-UHFFFAOYSA-N o-hydroxybenzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 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
- GNWXVOQHLPBSSR-UHFFFAOYSA-N oxolane;toluene Chemical compound C1CCOC1.CC1=CC=CC=C1 GNWXVOQHLPBSSR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229960001592 paclitaxel Drugs 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
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000009038 pharmacological inhibition Effects 0.000 description 1
- JMQPIZYYNQVMFO-UHFFFAOYSA-N phenyl 3-acetyl-4-propan-2-yl-4h-pyridine-1-carboxylate Chemical compound C1=C(C(C)=O)C(C(C)C)C=CN1C(=O)OC1=CC=CC=C1 JMQPIZYYNQVMFO-UHFFFAOYSA-N 0.000 description 1
- HUGKUQVNABLMNX-UHFFFAOYSA-N phenyl 3-cyano-4-cyclopropyl-4h-pyridine-1-carboxylate Chemical compound C1=CC(C2CC2)C(C#N)=CN1C(=O)OC1=CC=CC=C1 HUGKUQVNABLMNX-UHFFFAOYSA-N 0.000 description 1
- CKOOABJZYWLHMN-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1.C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 CKOOABJZYWLHMN-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 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
- 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
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000008569 process Effects 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
- 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
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 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
- 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
- 238000001953 recrystallisation 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
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 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
- 239000000377 silicon dioxide Substances 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
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 1
- WGRULTCAYDOGQK-UHFFFAOYSA-M sodium;sodium;hydroxide Chemical compound [OH-].[Na].[Na+] WGRULTCAYDOGQK-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 239000012265 solid product 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
- 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
- 230000003637 steroidlike 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
- 239000011550 stock solution Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection 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
- 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
- CLOXAWYNXXEWBT-UHFFFAOYSA-N tert-butyl n-(3-oxocyclopentyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1CCC(=O)C1 CLOXAWYNXXEWBT-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 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
- 229930192474 thiophene Natural products 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 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
- 125000005490 tosylate group Chemical group 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
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 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
- 125000005289 uranyl group Chemical group 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
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 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)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (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/US2002/030483 WO2003027085A2 (en) | 2001-09-26 | 2002-09-26 | 3-pyridyl or 4-isoquinolinyl thiazoles as c17,20 lyase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2461360A1 true CA2461360A1 (en) | 2003-04-03 |
Family
ID=23265979
Family Applications (2)
| 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 |
| CA002461363A Abandoned CA2461363A1 (en) | 2001-09-26 | 2002-09-26 | Substituted 3-pyridyl indoles and indazoles as c17,20 lyase inhibitors |
Family Applications After (1)
| 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 |
Country Status (5)
| Country | Link |
|---|---|
| EP (2) | EP1432706A2 (enExample) |
| JP (2) | JP2005532983A (enExample) |
| AU (2) | AU2002340010A1 (enExample) |
| CA (2) | CA2461360A1 (enExample) |
| WO (8) | WO2003027094A2 (enExample) |
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 |
| EP1348706B1 (en) * | 2000-12-08 | 2009-08-19 | Takeda Pharmaceutical Company Limited | Substituted thiazole derivatives bearing 3-pyridyl groups, process for preparing the same and use thereof |
| US20040147561A1 (en) * | 2002-12-27 | 2004-07-29 | Wenge Zhong | Pyrid-2-one derivatives and methods of use |
| CN102584813B (zh) * | 2003-05-14 | 2016-07-06 | Ngc药物公司 | 化合物及其在调节淀粉样蛋白β中的用途 |
| 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. |
| JP4869072B2 (ja) * | 2003-11-14 | 2012-02-01 | バーテックス ファーマシューティカルズ インコーポレイテッド | Atp結合カセットトランスポーターのモジュレーターとして有用なチアゾールおよびオキサゾール |
| ATE485824T1 (de) | 2004-04-13 | 2010-11-15 | Icagen Inc | Polycyclische pyrimidine als kaliumionenkanal- modulatoren |
| 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 |
| WO2006044456A1 (en) * | 2004-10-13 | 2006-04-27 | 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 |
| KR20070114123A (ko) * | 2005-01-19 | 2007-11-29 | 바이올리폭스 에이비 | 염증 치료에 유용한 인돌 |
| BRPI0608910A2 (pt) | 2005-05-09 | 2010-02-17 | Achillion Pharmaceuticals Inc | uso de um composto da fórmula ou um sal ou hidrato farmaceuticamente aceitável desse, composto ou sal ou hidrato do mesmo, composição farmacêutica e composição farmacêutica embalada |
| BRPI0614188A2 (pt) * | 2005-07-29 | 2011-03-15 | 4Sc Ag | compostos inibidores heterocìclicos de nf-kappab, uso dos mesmos e composição farmacêutica |
| FR2889526B1 (fr) * | 2005-08-04 | 2012-02-17 | Aventis Pharma Sa | 7-aza-indazoles substitues, compositions les contenant, procede de fabrication et utilisation |
| WO2007043400A1 (ja) * | 2005-10-07 | 2007-04-19 | Kissei Pharmaceutical Co., Ltd. | 含窒素芳香族複素環化合物およびそれを含有する医薬組成物 |
| 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 |
| WO2007077961A2 (en) * | 2005-12-28 | 2007-07-12 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compounds and their use as mineralocorticoid receptor ligands |
| CA2636826C (en) * | 2006-01-18 | 2011-11-29 | F.Hoffmann-La Roche Ag | Thiazoles as 11 beta-hsd1 inhibitors |
| HRP20130058T1 (hr) * | 2006-01-24 | 2013-02-28 | Eli Lilly & Company | Indolsulfonamidni modulatori progesteronskih receptora |
| SI2001849T1 (sl) * | 2006-03-29 | 2015-02-27 | F. Hoffmann-La Roche Ag | Derivati piridina in pirimidina kot antagonisti mglur2 |
| WO2008021337A1 (en) | 2006-08-15 | 2008-02-21 | Wyeth | Oxazinan-2-one derivatives useful as pr modulators |
| US7652018B2 (en) | 2006-08-15 | 2010-01-26 | Wyeth Llc | Imidazolidin-2-one derivatives useful as PR modulators |
| US7649007B2 (en) | 2006-08-15 | 2010-01-19 | Wyeth Llc | Oxazolidine derivatives as PR modulators |
| US7618989B2 (en) | 2006-08-15 | 2009-11-17 | Wyeth | Tricyclic oxazolidone derivatives useful as PR modulators |
| US8183264B2 (en) | 2006-09-21 | 2012-05-22 | Eisai R&D Managment Co., Ltd. | Pyridine derivative substituted by heteroaryl ring, and antifungal agent comprising the same |
| ATE534642T1 (de) * | 2006-09-21 | 2011-12-15 | Eisai R&D Man Co Ltd | Durch einen heteroarylring substituiertes pyridinderivat und antipilzmittel, das dieses enthält |
| 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 |
| MX2009012613A (es) | 2007-05-22 | 2010-04-21 | Achillion Pharmaceuticals Inc | Tiazoles substituidos por heteroarilo y su uso como agentes antivirales. |
| WO2009023721A1 (en) | 2007-08-13 | 2009-02-19 | Divergence, Inc. | Compositions and methods for controlling nematodes |
| AU2008310097B2 (en) | 2007-10-09 | 2013-05-16 | Merck Patent Gmbh | Pyridine derivatives useful as glucokinase activators |
| 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 |
| WO2009087224A1 (en) * | 2008-01-11 | 2009-07-16 | Novartis Ag | Pyrimidines as kinase inhibitors |
| WO2009094224A1 (en) | 2008-01-25 | 2009-07-30 | Millennium Pharmaceuticals, Inc. | Thiophenes and their use as phosphatidylinositol 3-kinase (pi3k) inhibitors |
| KR101047242B1 (ko) | 2008-02-08 | 2011-07-06 | 가부시키가이샤 시세이도 | 미백제 및 피부 외용제 |
| US9029408B2 (en) | 2008-06-16 | 2015-05-12 | Gtx, Inc. | Compounds for treatment of cancer |
| US9447049B2 (en) | 2010-03-01 | 2016-09-20 | University Of Tennessee Research Foundation | Compounds for treatment of cancer |
| US9334242B2 (en) | 2008-06-16 | 2016-05-10 | Gtx, Inc. | Compounds for treatment of cancer |
| LT2303021T (lt) * | 2008-06-16 | 2019-06-25 | University Of Tennessee Research Foundation | Junginiai, skirti vėžio gydymui |
| US8822513B2 (en) | 2010-03-01 | 2014-09-02 | Gtx, Inc. | Compounds for treatment of cancer |
| CA2734486A1 (en) * | 2008-08-20 | 2010-02-25 | Southern Research Institute | Substituted pyridine and pyrimidine derivatives and their use in treating viral infections |
| WO2010033977A2 (en) | 2008-09-22 | 2010-03-25 | Cayman Chemical Company | Multiheteroaryl compounds as inhibitors of h-pgds and their use for treating prostaglandin d2 mediated diseases |
| US9139589B2 (en) | 2009-01-30 | 2015-09-22 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| US9090601B2 (en) | 2009-01-30 | 2015-07-28 | Millennium Pharmaceuticals, Inc. | Thiazole derivatives |
| US8796314B2 (en) | 2009-01-30 | 2014-08-05 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| WO2010106290A1 (fr) * | 2009-03-19 | 2010-09-23 | Sanofi-Aventis | Derives d'indazole inhibiteurs d'hsp90, compositions les contenant et utilisation |
| ES2759949T3 (es) * | 2009-10-29 | 2020-05-12 | Bristol Myers Squibb Co | Compuestos heterocíclicos tricíclicos |
| 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 |
| US8673922B2 (en) | 2010-07-15 | 2014-03-18 | Bristol-Myers Squibb Company | Azaindazole compounds |
| EP2600855A2 (en) | 2010-08-04 | 2013-06-12 | Pellficure Pharmaceuticals, Inc. | Combination therapy for the treatment of prostate carcinoma |
| TW201217365A (en) | 2010-08-11 | 2012-05-01 | Millennium Pharm Inc | Heteroaryls and uses thereof |
| EP2603216A4 (en) | 2010-08-11 | 2013-12-18 | Millennium Pharm Inc | HETEROARYLE AND USES THEREOF |
| WO2012021611A1 (en) | 2010-08-11 | 2012-02-16 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| UY33671A (es) | 2010-10-13 | 2012-04-30 | Millenium Pharmaceuticals Inc | Heteroarilos y sus usos |
| CN103270029B (zh) * | 2010-10-22 | 2016-01-20 | 拜耳知识产权有限责任公司 | 作为农药的杂环化合物 |
| AU2011320565A1 (en) * | 2010-10-28 | 2013-05-23 | Innocrin Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| JP2013542259A (ja) | 2010-11-12 | 2013-11-21 | ブリストル−マイヤーズ スクイブ カンパニー | 置換アザインダゾール化合物 |
| 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 |
| WO2013049263A1 (en) | 2011-09-27 | 2013-04-04 | Bristol-Myers Squibb Company | Substituted bicyclic heteroaryl compounds |
| JP6496246B2 (ja) * | 2012-10-05 | 2019-04-03 | メルク・シャープ・アンド・ドーム・コーポレーションMerck Sharp & Dohme Corp. | アルドステロンシンターゼインヒビター関連用途としてのインドリン化合物 |
| WO2014099833A1 (en) * | 2012-12-20 | 2014-06-26 | Merck Sharp & Dohme Corp. | Indazole compounds as aldosterone synthase inhibitors |
| CN109568312A (zh) | 2013-03-05 | 2019-04-05 | 田纳西大学研究基金会 | 用于治疗癌症的化合物 |
| AU2014241816B9 (en) | 2013-03-14 | 2019-02-14 | 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 |
| EP4077332A4 (en) * | 2019-12-18 | 2024-05-01 | The Regents of the University of California | LIN28 INHIBITORS AND THEIR METHODS OF USE |
| 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 (enExample) * | 1991-11-25 | 1994-05-01 | Sumitomo Chemical Co | |
| US5395817A (en) * | 1992-01-22 | 1995-03-07 | Imperial Chemical Industries Plc | N-arylindoles and their use as herbicides |
| US5599774A (en) * | 1992-01-22 | 1997-02-04 | Imperial Chemical Industries Plc | N-arylindoles and their use as herbicides |
| ATE194332T1 (de) * | 1992-03-09 | 2000-07-15 | Zeneca Ltd | Arylindazoline und ihre anwendung als herbizide |
| US5444038A (en) * | 1992-03-09 | 1995-08-22 | Zeneca Limited | Arylindazoles and their use as herbicides |
| CA2206315A1 (en) * | 1994-11-29 | 1996-06-06 | 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 |
| WO1999018099A1 (en) * | 1997-10-03 | 1999-04-15 | Merck Frosst Canada & Co. | Aryl thiophene derivatives as pde iv inhibitors |
| CN1308618A (zh) * | 1998-05-12 | 2001-08-15 | 美国家用产品公司 | 用于治疗胰岛素抗性和高血糖的噁唑芳基-羧酸 |
| WO2000006556A1 (en) * | 1998-07-27 | 2000-02-10 | Abbott Laboratories | Substituted oxazolines as antiproliferative agents |
| DE60136530D1 (de) * | 2000-03-01 | 2008-12-24 | Janssen Pharmaceutica Nv | 2,4-disubstituierte thiazolyl derivate |
-
2002
- 2002-09-26 JP JP2003530675A patent/JP2005532983A/ja not_active Withdrawn
- 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
- 2002-09-26 EP EP02799636A patent/EP1432706A2/en not_active Withdrawn
- 2002-09-26 WO PCT/US2002/030982 patent/WO2003027095A1/en not_active Ceased
- 2002-09-26 CA CA002461360A patent/CA2461360A1/en not_active Abandoned
- 2002-09-26 WO PCT/US2002/030981 patent/WO2003027105A1/en not_active Ceased
- 2002-09-26 EP EP02778338A patent/EP1432698A2/en not_active Withdrawn
- 2002-09-26 AU AU2002340010A patent/AU2002340010A1/en not_active Abandoned
- 2002-09-26 AU AU2002362603A patent/AU2002362603A1/en not_active Abandoned
- 2002-09-26 CA CA002461363A patent/CA2461363A1/en not_active Abandoned
- 2002-09-26 WO PCT/US2002/030924 patent/WO2003027100A1/en not_active Ceased
- 2002-09-26 JP JP2003530682A patent/JP2005528325A/ja not_active Withdrawn
- 2002-09-26 WO PCT/US2002/030983 patent/WO2003027096A1/en not_active Ceased
- 2002-09-26 WO PCT/US2002/030979 patent/WO2003027101A1/en not_active Ceased
- 2002-09-26 WO PCT/US2002/030483 patent/WO2003027085A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP1432706A2 (en) | 2004-06-30 |
| AU2002340010A1 (en) | 2003-04-07 |
| WO2003027101A1 (en) | 2003-04-03 |
| WO2003027100A1 (en) | 2003-04-03 |
| EP1432698A2 (en) | 2004-06-30 |
| AU2002362603A1 (en) | 2003-04-07 |
| WO2003027085A3 (en) | 2003-12-04 |
| JP2005528325A (ja) | 2005-09-22 |
| WO2003027096A1 (en) | 2003-04-03 |
| CA2461363A1 (en) | 2003-04-03 |
| WO2003027105A1 (en) | 2003-04-03 |
| WO2003027107A1 (en) | 2003-04-03 |
| WO2003027095A1 (en) | 2003-04-03 |
| WO2003027094A3 (en) | 2003-10-23 |
| WO2003027094A2 (en) | 2003-04-03 |
| JP2005532983A (ja) | 2005-11-04 |
| WO2003027085A2 (en) | 2003-04-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2461360A1 (en) | 3-pyridyl or 4-isoquinolinyl thiazoles as c17,20 lyase inhibitors | |
| US20040198773A1 (en) | Substituted 3-pyridyl oxazoles as c17,20 lyase inhibitors | |
| US20040267017A1 (en) | 3-pyridyl or 4-isoquinolinyl thiazoles as c17, 20 lyase inhibitors | |
| EP1751146B1 (en) | Pyridinyl- or pyrimidinyl thiazoles with protein kinase inhibiting activity | |
| AU2007237904B2 (en) | 6-O-substituted benzoxazole and benzothiazole compounds and methods of inhibiting CSF-1R signaling | |
| CN109761976B (zh) | 八氢稠合的氮杂萘烷糖皮质激素受体调节剂 | |
| JP5074653B2 (ja) | 2−置換4−ヘテロアリール−ピリミジンおよび増殖性障害におけるその使用 | |
| AU2006290814B2 (en) | 2-aniline-4-aryl substituted thiazole derivatives | |
| CA2872260C (en) | Heteroaryl-ketone fused azadecalin glucocorticoid receptor modulators | |
| JP5363315B2 (ja) | 新規ピペラジン、医薬組成物、およびその使用方法 | |
| CA2542536A1 (en) | Triazolo-pyridazine compounds and derivatives thereof useful in the treatment of neuropathic pain | |
| KR20110031367A (ko) | 화합물 251 | |
| KR102214222B1 (ko) | 신규 pde4 저해제 | |
| KR20090026187A (ko) | 티로신 키나제 억제제 | |
| JP2011517452A (ja) | 抗増殖性化合物およびその治療的使用 | |
| AU2005270102A1 (en) | Compounds useful for inhibiting Chk1 | |
| US20040236110A1 (en) | Substituted 3-pyridyl indoles and indazoles as c17,20 lyase inhibitors | |
| KR20140027907A (ko) | 치환된 벤즈아미드 및 그의 용도 | |
| JP6130383B2 (ja) | ピリジン誘導体 | |
| AU2013245809A1 (en) | Substituted benzamides and their uses | |
| EP2760870B1 (en) | Substituted bicyclic heteroaryl compounds | |
| US20040209924A1 (en) | Substituted 3-pyridyl imidazoles as c17,20 lyase inhibitors | |
| JP2004516322A (ja) | ファルネシルトランスフェラーゼを阻害する4−ヘテロシクリル−キノリンおよびキナゾリン誘導体 | |
| EP1814554A1 (en) | Certain compounds, compositions, and methods | |
| JPS59167586A (ja) | チオフエン誘導体 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |