KR20140138654A - 트리아지논 화합물 및 t형 칼슘채널 저해제 - Google Patents
트리아지논 화합물 및 t형 칼슘채널 저해제 Download PDFInfo
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- KR20140138654A KR20140138654A KR1020147023774A KR20147023774A KR20140138654A KR 20140138654 A KR20140138654 A KR 20140138654A KR 1020147023774 A KR1020147023774 A KR 1020147023774A KR 20147023774 A KR20147023774 A KR 20147023774A KR 20140138654 A KR20140138654 A KR 20140138654A
- Authority
- KR
- South Korea
- Prior art keywords
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- cycloalkyl
- substituent
- substituted
- mono
- Prior art date
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- -1 Triazinone compound Chemical class 0.000 title claims abstract description 298
- DKNDOKIVCXTFHJ-HNNXBMFYSA-N 3,5-dichloro-n-[[1-[[(4s)-2,2-dimethyloxan-4-yl]methyl]-4-fluoropiperidin-4-yl]methyl]benzamide Chemical compound C1COC(C)(C)C[C@H]1CN1CCC(F)(CNC(=O)C=2C=C(Cl)C=C(Cl)C=2)CC1 DKNDOKIVCXTFHJ-HNNXBMFYSA-N 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 540
- 125000001424 substituent group Chemical group 0.000 claims abstract description 522
- 150000003839 salts Chemical class 0.000 claims abstract description 112
- 239000012453 solvate Substances 0.000 claims abstract description 109
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims abstract description 94
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 87
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 77
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims abstract description 63
- 125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 47
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 43
- 125000003118 aryl group Chemical group 0.000 claims abstract description 22
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 198
- 125000000623 heterocyclic group Chemical group 0.000 claims description 155
- 238000000034 method Methods 0.000 claims description 98
- 125000000217 alkyl group Chemical group 0.000 claims description 92
- 125000005843 halogen group Chemical group 0.000 claims description 80
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 77
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 68
- 229910052760 oxygen Inorganic materials 0.000 claims description 67
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 65
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 62
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 57
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 57
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 57
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 55
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 55
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 53
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 49
- 125000003277 amino group Chemical group 0.000 claims description 48
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 47
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 44
- 229910052717 sulfur Inorganic materials 0.000 claims description 40
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 39
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 36
- 229910005965 SO 2 Inorganic materials 0.000 claims description 36
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 36
- 229910052799 carbon Inorganic materials 0.000 claims description 33
- 239000000126 substance Substances 0.000 claims description 29
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 27
- 125000004414 alkyl thio group Chemical group 0.000 claims description 26
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 26
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 26
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 26
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 26
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 26
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 25
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 21
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 19
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 18
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical group OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 102000003691 T-Type Calcium Channels Human genes 0.000 claims description 16
- 108090000030 T-Type Calcium Channels Proteins 0.000 claims description 16
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 14
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims description 13
- 230000008676 import Effects 0.000 claims description 13
- 125000005628 tolylene group Chemical group 0.000 claims description 13
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 12
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 11
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims description 9
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 208000004296 neuralgia Diseases 0.000 claims description 8
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 7
- 125000006587 (C5-C10) heteroarylene group Chemical group 0.000 claims description 7
- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 208000021722 neuropathic pain Diseases 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 2
- 241001024304 Mino Species 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 241001122767 Theaceae Species 0.000 claims 1
- 208000002193 Pain Diseases 0.000 abstract description 23
- 230000036407 pain Effects 0.000 abstract description 18
- 102000003922 Calcium Channels Human genes 0.000 abstract description 9
- 108090000312 Calcium Channels Proteins 0.000 abstract description 9
- 230000001419 dependent effect Effects 0.000 abstract description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 237
- 239000000243 solution Substances 0.000 description 205
- 238000003786 synthesis reaction Methods 0.000 description 185
- 230000015572 biosynthetic process Effects 0.000 description 182
- 238000006243 chemical reaction Methods 0.000 description 166
- 239000000203 mixture Substances 0.000 description 151
- 230000002829 reductive effect Effects 0.000 description 118
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 108
- 239000012043 crude product Substances 0.000 description 94
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 91
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 81
- 239000012044 organic layer Substances 0.000 description 59
- 239000002904 solvent Substances 0.000 description 59
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
- 239000011541 reaction mixture Substances 0.000 description 42
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 37
- 229920006395 saturated elastomer Polymers 0.000 description 37
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
- 238000004519 manufacturing process Methods 0.000 description 33
- 238000010898 silica gel chromatography Methods 0.000 description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
- 238000010992 reflux Methods 0.000 description 26
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 24
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 23
- 238000010438 heat treatment Methods 0.000 description 23
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 23
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
- 239000007788 liquid Substances 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 17
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 150000001924 cycloalkanes Chemical class 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 12
- 235000019270 ammonium chloride Nutrition 0.000 description 12
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 12
- 125000006239 protecting group Chemical group 0.000 description 12
- 239000002994 raw material Substances 0.000 description 12
- 229940086542 triethylamine Drugs 0.000 description 12
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 11
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 10
- RMHQDKYZXJVCME-UHFFFAOYSA-N 2-pyridin-4-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=NC=C1 RMHQDKYZXJVCME-UHFFFAOYSA-N 0.000 description 10
- PYXNITNKYBLBMW-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-pyrazole Chemical compound FC(F)(F)C1=CC=NN1 PYXNITNKYBLBMW-UHFFFAOYSA-N 0.000 description 10
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 125000004429 atom Chemical group 0.000 description 10
- 150000001925 cycloalkenes Chemical class 0.000 description 10
- 208000035475 disorder Diseases 0.000 description 10
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 10
- 239000011780 sodium chloride Substances 0.000 description 10
- 239000012312 sodium hydride Substances 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- 238000010511 deprotection reaction Methods 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 125000001153 fluoro group Chemical group F* 0.000 description 9
- 229910052740 iodine Inorganic materials 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 9
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 229940002612 prodrug Drugs 0.000 description 8
- 239000000651 prodrug Substances 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 239000011259 mixed solution Substances 0.000 description 7
- 201000001119 neuropathy Diseases 0.000 description 7
- 230000007823 neuropathy Effects 0.000 description 7
- 208000033808 peripheral neuropathy Diseases 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 125000004434 sulfur atom Chemical group 0.000 description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 6
- IIYRJYZDFOBAKW-UHFFFAOYSA-N 1-(4-fluorophenyl)pyrrolidine Chemical compound C1=CC(F)=CC=C1N1CCCC1 IIYRJYZDFOBAKW-UHFFFAOYSA-N 0.000 description 6
- IWTFOFMTUOBLHG-UHFFFAOYSA-N 2-methoxypyridine Chemical compound COC1=CC=CC=N1 IWTFOFMTUOBLHG-UHFFFAOYSA-N 0.000 description 6
- GZXDOXSIKJNUEW-UHFFFAOYSA-N 5-methylthiophene Chemical compound CC1=C=C[CH]S1 GZXDOXSIKJNUEW-UHFFFAOYSA-N 0.000 description 6
- QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 150000001350 alkyl halides Chemical class 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 238000000132 electrospray ionisation Methods 0.000 description 6
- 230000014509 gene expression Effects 0.000 description 6
- 125000005549 heteroarylene group Chemical group 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
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- WUOQXNWMYLFAHT-QMMMGPOBSA-N tert-butyl n-[(3s)-piperidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H]1CCCNC1 WUOQXNWMYLFAHT-QMMMGPOBSA-N 0.000 description 1
- DQQJBEAXSOOCPG-ZETCQYMHSA-N tert-butyl n-[(3s)-pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H]1CCNC1 DQQJBEAXSOOCPG-ZETCQYMHSA-N 0.000 description 1
- DQQJBEAXSOOCPG-UHFFFAOYSA-N tert-butyl n-pyrrolidin-3-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNC1 DQQJBEAXSOOCPG-UHFFFAOYSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- ONCNIMLKGZSAJT-UHFFFAOYSA-N thieno[3,2-b]furan Chemical compound S1C=CC2=C1C=CO2 ONCNIMLKGZSAJT-UHFFFAOYSA-N 0.000 description 1
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 1
- 229940125670 thienopyridine Drugs 0.000 description 1
- 239000002175 thienopyridine Substances 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 230000003202 urodynamic effect Effects 0.000 description 1
- 229940102566 valproate Drugs 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Abstract
[해결수단] 식(I)
(식 중 각 치환기는 본문에서 상세하게 정의되지만, R1은 수소원자 또는 C1 - 6알콕시기 등, L1 및 L2는 각각 독립적으로 단결합 또는 NR2 등, L3은 C1 - 6알킬렌기 등, A는 치환될 수도 있는 C6 - 14아릴기 또는 5-10원 헤테로아릴기 등, B는 C3 - 11시클로알킬렌기 등, D는 치환될 수도 있는 C6 - 14아릴기 또는 5-10원 헤테로아릴기 등을 의미한다.)로 표시되는 신규 트리아지논 화합물, 이 화합물의 호변이성체 혹은 그 의약적으로 허용될 수 있는 염 또는 이들의 용매화물을 제공하는 것이다.
Description
Claims (20)
- 식(I):
[화학식 1]
[식 중,
R1은,
수소원자,
할로겐원자,
C1 - 6알킬기,
C1 - 6알콕시기,
C1 - 6알킬티오기,
모노C1 - 6알킬아미노기,
디C1 - 6알킬아미노기
(이 C1 - 6알킬기, C1 - 6알콕시기, C1 - 6알킬티오기, 모노C1 - 6알킬아미노기 및 디C1 - 6알킬아미노기는, 비치환이거나, 또는 치환기군 V8로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.)
또는 C3 - 11시클로알킬기
(이 C3 - 11시클로알킬기는, 비치환이거나, 또는 치환기군 V6으로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.)
를 의미하고,
L1 및 L2는, 각각 독립적으로
단결합,
NR2,
O,
S,
SO,
SO2
또는 C1 - 6알킬렌기
(이 C1 - 6알킬렌기는, 비치환이거나, 또는 치환기군 V6으로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있고, 또한 이 C1 - 6알킬렌기 중 1개의 메틸렌기는, O, S, SO2, C=O, C=S 또는 NR3으로 치환되어 있을 수도 있다.)
중 어느 하나를 의미하고,
B는,
C3 - 11시클로알킬렌기,
C3 - 11시클로알케닐렌기,
3-11원 헤테로사이클릴렌기,
C6 - 14아릴렌기,
5-10원 헤테로아릴렌기
(이 C3 - 11시클로알킬렌기, C3 - 11시클로알케닐렌기, 3-11원 헤테로사이클릴렌기, C6-14아릴렌기 및 5-10원 헤테로아릴렌기는 비치환이거나, 또는 치환기군 V6으로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있으며,
또한 이 C3 - 11시클로알킬렌기 및 C3 - 11시클로알케닐렌기 중 1개의 메틸렌기는, 1,1-C3 - 7시클로알킬렌기로 치환될 수도 있다.),
C1 - 6알킬렌기,
C2 - 6알케닐렌기
또는 C2 - 6알키닐렌기
(이 C1 - 6알킬렌기, C2 - 6알케닐렌기 및 C2 - 6알키닐렌기는 비치환이거나, 또는 치환기군 V8로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있으며,
또한 이 C1 - 6알킬렌기, C2 - 6알케닐렌기 및 C2 - 6알키닐렌기 중 1개의 메틸렌기는, 1,1-C3 - 7시클로알킬렌기로 치환될 수도 있다.)
를 의미하고, 단, L1이 단결합, O 또는 C1 - 6알킬렌기로서, L2가 단결합 또는 C1 - 6알킬렌기일 때, B는 C1 - 6알킬렌기, C2 - 6알케닐렌기, C2 - 6알키닐렌기 또는 C6 - 14아릴렌기가 아니며, L1이 단결합, O 또는 C1 - 6알킬렌기로서, L2가 NR2, O, S, SO, SO2일 때, B는 C1 - 6알킬렌기, C2-6알케닐렌기 또는 C2 - 6알키닐렌기가 아니며
A는,
C1 - 6알킬기,
C2 - 6알케닐기
(이 C1 - 6알킬기 및 C2 - 6알케닐기는 비치환이거나, 또는 치환기군 V8로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.), C3 - 11시클로알킬기,
C3 - 11시클로알케닐기,
3-11원 헤테로사이클릴기,
C6 - 14아릴기
또는 5-10원 헤테로아릴기
(이 C3 - 11시클로알킬기, C3 - 11시클로알케닐기, 3-11원 헤테로사이클릴기, C6 - 14아릴기 및 5-10원 헤테로아릴기는, 비치환이거나, 또는 치환기군 V6으로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.)
를 의미하고,
L3은,
C1 - 6알킬렌기
(이 C1 - 6알킬렌기는, 비치환이거나, 또는 치환기군 V8로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있고, 또한 이 C1 - 6알킬렌기 중 1개의 메틸렌기는 C=O 또는 C=S에 의해 치환되어 있을 수도 있다.)를 의미하고,
D는,
C3 - 11시클로알킬기,
C3 - 11시클로알케닐기,
3-11원 헤테로사이클릴기,
C6 - 14아릴기
또는 5-10원 헤테로아릴기
(이 C3 - 11시클로알킬기, C3 - 11시클로알케닐기, 3-11원 헤테로사이클릴기, C6 - 14아릴기 및 5-10원 헤테로아릴기는 비치환이거나, 또는 치환기군 V6으로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.)를 의미하고,
R2 및 R3은, 각각 독립적으로
수소원자,
C1 - 6알킬기,
C2 - 6알케닐기
(이 C1 - 6알킬기 및 C2 - 6알케닐기는, 비치환이거나, 또는 치환기군 V8로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.),
C3 - 11시클로알킬기,
3-11원 헤테로사이클릴기,
C6 - 14아릴기
또는 5-10원 헤테로아릴기
(이 C3 - 11시클로알킬기, 3-11원 헤테로사이클릴기, C6 - 14아릴기 및 5-10원 헤테로아릴기는, 비치환이거나, 또는 치환기군 V6으로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.)
를 의미하고,
치환기군 V6은, 치환기군 V8을 구성하는 각 치환기, C1 - 6알킬기, C2 - 6알케닐기 및 C2 -6알키닐기(이 C1 - 6알킬기, C2 - 6알케닐기 및 C2 - 6알키닐기는, 비치환이거나, 또는 치환기군 V1로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.)에 의해 구성되는 치환기군을 의미하고,
치환기군 V8은, 치환기군 Va를 구성하는 각 치환기, C1 - 6알콕시기, C1 - 6알킬티오기, C1 - 6알킬카르보닐기, C1 - 6알킬설포닐기, C1 - 6알콕시카르보닐기, 모노C1 - 6알킬아미노기, 디C1 - 6알킬아미노기, 모노C1 - 6알킬아미노카르보닐기, 디C1 - 6알킬아미노카르보닐기, 모노C1 - 6알킬아미노설포닐기, 디C1 - 6알킬아미노설포닐기, C1 - 6알킬카르보닐아미노기, C1 - 6알킬카르보닐옥시기, C1 - 6알킬설포닐아미노기, C1 -6알킬설포닐옥시기(이 C1 - 6알콕시기, C1 - 6알킬티오기, C1 - 6알킬카르보닐기, C1 - 6알킬설포닐기, C1 - 6알콕시카르보닐기, 모노C1 - 6알킬아미노기, 디C1- 6알킬아미노기, 모노C1 - 6알킬아미노카르보닐기, 디C1 - 6알킬아미노카르보닐기, 모노C1-6알킬아미노설포닐기, 디C1 - 6알킬아미노설포닐기, C1 - 6알킬카르보닐아미노기, C1 - 6알킬카르보닐옥시기, C1 - 6알킬설포닐아미노기 및 C1 - 6알킬설포닐옥시기는, 비치환이거나, 또는 치환기군 V1로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.), C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3 - 6시클로알킬아미노기, C3-6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬설포닐아미노기, C3 - 6시클로알킬설포닐옥시기, C3 - 6시클로알킬티오기, C3 - 11시클로알킬기, 3-11원 헤테로사이클릴기, C6 - 14아릴기 및 5-10원 헤테로아릴기(이 C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3 - 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬설포닐아미노기, C3 - 6시클로알킬설포닐옥시기, C3 - 6시클로알킬티오기, C3 - 11시클로알킬기, 3-11원 헤테로사이클릴기, C6 - 14아릴기 및 5-10원 헤테로아릴기는, 비치환이거나, 또는 치환기군 V2로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.)에 의해 구성되는 치환기군을 의미하고,
치환기군 Va는, 수산기, 할로겐원자, 시아노기, 니트로기, 아미노기, 카르복시기, 카바모일기, 설파모일기, 포스포노기, 설포기, 테트라졸릴기, 포르메이트기 및 포밀기에 의해 구성되는 치환기군을 의미하고,
치환기군 V1은, 치환기군 Va를 구성하는 각 치환기, C1 - 6알콕시기, C1 - 3할로알콕시기, 모노C1- 6알킬아미노기, 디C1 - 6알킬아미노기, 모노C1 - 6알킬아미노카르보닐기, 디C1 - 6알킬아미노카르보닐기, C1 - 6알킬카르보닐아미노기, C1 - 6알킬티오기, C1 - 6알킬설포닐기, C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3 - 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, 3-11원 헤테로사이클릴기, C6 - 14아릴기 또는 5-10원 헤테로아릴기(이 C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3- 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, 3-11원 헤테로사이클릴기, C6 - 14아릴기 및 5-10원 헤테로아릴기는, 비치환이거나, 또는 수산기, 할로겐원자, 시아노기, 니트로기, 아미노기, 카르복시기, 카바모일기, 설파모일기, 포스포노기, 포스피노일기, 설포기, 설피노기, 테트라졸릴기, 포밀기, C1 - 6알킬기, C1 - 3할로알킬기, C1 - 6알콕시기, C1-3할로알콕시기, 모노C1 - 6알킬아미노기, 디C1 - 6알킬아미노기, 모노C1 - 6알킬아미노카르보닐기, 디C1 - 6알킬아미노카르보닐기, C1 - 6알킬카르보닐아미노기, C1 - 6알킬티오기 또는 C1-6알킬설포닐기로 치환되어 있다.)에 의해 구성되는 치환기군을 의미하고,
치환기군 V2는, 치환기군 V1을 구성하는 각 치환기, C1 - 6알킬기 및 C1 - 3할로알킬기에 의해 구성되는 치환기군을 의미한다.]
로 표시되는 화합물, 이 화합물의 호변이성체 혹은 그 의약적으로 허용될 수 있는 염 또는 이들의 용매화물.
- 제1항에 있어서,
L3이, C1 - 3알킬렌기인 화합물, 이 화합물의 호변이성체 혹은 그 의약적으로 허용될 수 있는 염 또는 이들의 용매화물.
- 제1항 또는 제2항에 있어서,
R1이 수소원자 또는 C1 -6알콕시기(이 C1 - 6알콕시기는, 비치환이거나, 또는 치환기군 V7로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.)이고,
치환기군 V7은, 수산기, 할로겐원자, 시아노기, 니트로기, C1 - 6알콕시기, C1 - 6알킬티오기, C1-6알콕시카르보닐기(이 C1 - 6알콕시기, C1 - 6알킬티오기 및 C1 - 6알콕시카르보닐기는, 비치환이거나, 또는 치환기군 V1로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.), C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3 - 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, C3-6시클로알킬기, 4-7원 헤테로사이클릴기, 페닐기 및 5-6원 헤테로아릴기(이 C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3 - 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, C3 - 6시클로알킬기, 4-7원 헤테로사이클릴기, 페닐기 및 5-6원 헤테로아릴기는, 비치환이거나, 또는 치환기군 V2로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.)에 의해 구성되는 치환기군을 의미하고,
치환기군 V1은, 치환기군 Va를 구성하는 각 치환기, C1 - 6알콕시기, C1 - 3할로알콕시기, 모노C1- 6알킬아미노기, 디C1 - 6알킬아미노기, 모노C1 - 6알킬아미노카르보닐기, 디C1 - 6알킬아미노카르보닐기, C1 - 6알킬카르보닐아미노기, C1 - 6알킬티오기, C1 - 6알킬설포닐기, C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3 - 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, 3-11원 헤테로사이클릴기, C6 - 14아릴기 또는 5-10원 헤테로아릴기(이 C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3- 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, 3-11원 헤테로사이클릴기, C6 - 14아릴기 및 5-10원 헤테로아릴기는, 비치환이거나, 또는 수산기, 할로겐원자, 시아노기, 니트로기, 아미노기, 카르복시기, 카바모일기, 설파모일기, 포스포노기, 포스피노일기, 설포기, 설피노기, 테트라졸릴기, 포밀기, C1-6알킬기, C1 - 3할로알킬기, C1 - 6알콕시기, C1 - 3할로알콕시기, 모노C1 - 6알킬아미노기, 디C1 -6알킬아미노기, 모노C1 - 6알킬아미노카르보닐기, 디C1 - 6알킬아미노카르보닐기, C1 - 6알킬카르보닐아미노기, C1 - 6알킬티오기 또는 C1 - 6알킬설포닐기로 치환되어 있다.)에 의해 구성되는 치환기군을 의미하고,
치환기군 V2는, 치환기군 V1을 구성하는 각 치환기, C1 - 6알킬기 및 C1 - 3할로알킬기에 의해 구성되는 치환기군을 의미하고,
치환기군 Va는, 수산기, 할로겐원자, 시아노기, 니트로기, 아미노기, 카르복시기, 카바모일기, 설파모일기, 포스포노기, 설포기, 테트라졸릴기, 포르메이트기 및 포밀기에 의해 구성되는 치환기군을 의미하는 화합물, 이 화합물의 호변이성체 혹은 그 의약적으로 허용될 수 있는 염 또는 이들의 용매화물.
- 제3항에 있어서,
R1이 수소원자인 화합물, 이 화합물의 호변이성체 혹은 그 의약적으로 허용될 수 있는 염 또는 이들의 용매화물.
- 제1항 또는 제2항에 있어서,
R1이 C1 - 6알킬기(이 C1 - 6알킬기는, 비치환이거나, 또는 치환기군 V9로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.)이고,
치환기군 V9는, 수산기, 할로겐원자, 시아노기, 니트로기, C1 - 6알콕시기, C1 - 6알킬티오기, C1-6알킬카르보닐옥시기, C1 -6알콕시카르보닐기(이 C1 - 6알콕시기, C1 - 6알킬티오기, C1 - 6알킬카르보닐옥시기 및 C1 - 6알콕시카르보닐기는, 비치환이거나, 또는 치환기군 V1로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.), C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3 - 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, C3 - 6시클로알킬기, 4-7원 헤테로사이클릴기, 페닐기 및 5-6원 헤테로아릴기(이 C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3 - 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, C3 - 6시클로알킬기, 4-7원 헤테로사이클릴기, 페닐기 및 5-6원 헤테로아릴기는, 비치환이거나, 또는 치환기군 V2로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.)에 의해 구성되는 치환기군을
의미하고,
치환기군 V1은, 치환기군 Va를 구성하는 각 치환기, C1 - 6알콕시기, C1 - 3할로알콕시기, 모노C1- 6알킬아미노기, 디C1 - 6알킬아미노기, 모노C1 - 6알킬아미노카르보닐기, 디C1 - 6알킬아미노카르보닐기, C1 - 6알킬카르보닐아미노기, C1 - 6알킬티오기, C1 - 6알킬설포닐기, C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3 - 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, 3-11원 헤테로사이클릴기, C6 - 14아릴기 또는 5-10원 헤테로아릴기(이 C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3- 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, 3-11원 헤테로사이클릴기, C6 - 14아릴기 및 5-10원 헤테로아릴기는, 비치환이거나, 또는 수산기, 할로겐원자, 시아노기, 니트로기, 아미노기, 카르복시기, 카바모일기, 설파모일기, 포스포노기, 포스피노일기, 설포기, 설피노기, 테트라졸릴기, 포밀기, C1-6알킬기, C1 - 3할로알킬기, C1 - 6알콕시기, C1 - 3할로알콕시기, 모노C1 - 6알킬아미노기, 디C1 -6알킬아미노기, 모노C1 - 6알킬아미노카르보닐기, 디C1 - 6알킬아미노카르보닐기, C1 - 6알킬카르보닐아미노기, C1 - 6알킬티오기 또는 C1 - 6알킬설포닐기로 치환되어 있다.)에 의해 구성되는 치환기군을 의미하고,
치환기군 V2는, 치환기군 V1을 구성하는 각 치환기, C1 - 6알킬기 및 C1 - 3할로알킬기에 의해 구성되는 치환기군을 의미하고,
치환기군 Va는, 수산기, 할로겐원자, 시아노기, 니트로기, 아미노기, 카르복시기, 카바모일기, 설파모일기, 포스포노기, 설포기, 테트라졸릴기, 포르메이트기 및 포밀기에 의해 구성되는 치환기군을 의미하는 화합물, 이 화합물의 호변이성체 혹은 그 의약적으로 허용될 수 있는 염 또는 이들의 용매화물.
- 제5항에 있어서,
R1이 C1 - 6알킬기(이 C1 - 6알킬기는, 비치환이거나, 또는 할로겐원자로 치환되어 있다.)인 화합물, 이 화합물의 호변이성체 혹은 그 의약적으로 허용될 수 있는 염 또는 이들의 용매화물.
- 제1항 내지 제6항 중 어느 한 항에 있어서,
L1이 단결합, NR2a, O, S, SO, SO2 또는 C1 -6알킬렌기(이 C1 - 6알킬렌기 중 1개의 메틸렌기는, O, S, SO2, C=O, C=S 또는 NR3a로 치환되어 있을 수도 있다.)이고,
L2와 B가,
L2가 단결합이고, 또한 B가, 3-11원 헤테로사이클릴렌기 또는 5-10원 헤테로아릴렌기(이 3-11원 헤테로사이클릴렌기 및 5-10원 헤테로아릴렌기는, 비치환이거나, 또는 치환기군 V5로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있을 수도 있다.)이거나,
또는, L2가 NR2b, O, S, SO, SO2 또는 C1 -6알킬렌기(이 C1 - 6알킬렌기 중 1개의 메틸렌기는, O, S, SO2, C=O, C=S 또는 NR3b로 치환되어 있을 수도 있다.)이고, 또한 B가, C3 - 11시클로알킬렌기, C3 - 11시클로알케닐렌기, 3-11원 헤테로사이클릴렌기 또는 5-10원 헤테로아릴렌기(이 C3 - 11시클로알킬렌기, C3 - 11시클로알케닐렌기, 3-11원 헤테로사이클릴렌기 및 5-10원 헤테로아릴렌기는, 비치환이거나, 또는 치환기군 V5로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있을 수도 있고, 또한 이 C3 - 11시클로알킬렌기 및 C3 - 11시클로알케닐렌기 중 1개의 메틸렌기는, 1,1-C3 - 7시클로알킬렌기로 치환될 수도 있다.)이고,
치환기군 V5는, 수산기, 할로겐원자, 시아노기, 니트로기, C1 - 6알킬기, C1 - 6알콕시기, C1 - 6알킬티오기, C1 -6알콕시카르보닐기(이 C1 - 6알킬기, C1 - 6알콕시기, C1 - 6알킬티오기 및 C1 - 6알콕시카르보닐기는, 비치환이거나, 또는 치환기군 V1로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.), C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3 - 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, C3 - 6시클로알킬기, 4-7원 헤테로사이클릴기, 페닐기 및 5-6원 헤테로아릴기(이 C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3 - 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, C3 - 6시클로알킬기, 4-7원 헤테로사이클릴기, 페닐기 및 5-6원 헤테로아릴기는, 비치환이거나, 또는 치환기군 V2로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.)에 의해 구성되는 치환기군을 의미하고,
치환기군 V1은, 치환기군 Va를 구성하는 각 치환기, C1 - 6알콕시기, C1 - 3할로알콕시기, 모노C1- 6알킬아미노기, 디C1 - 6알킬아미노기, 모노C1 - 6알킬아미노카르보닐기, 디C1 - 6알킬아미노카르보닐기, C1 - 6알킬카르보닐아미노기, C1 - 6알킬티오기, C1 - 6알킬설포닐기, C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3 - 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, 3-11원 헤테로사이클릴기, C6 - 14아릴기 또는 5-10원 헤테로아릴기(이 C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3- 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, 3-11원 헤테로사이클릴기, C6 - 14아릴기 및 5-10원 헤테로아릴기는, 비치환이거나, 또는 수산기, 할로겐원자, 시아노기, 니트로기, 아미노기, 카르복시기, 카바모일기, 설파모일기, 포스포노기, 포스피노일기, 설포기, 설피노기, 테트라졸릴기, 포밀기, C1-6알킬기, C1 - 3할로알킬기, C1 - 6알콕시기, C1 - 3할로알콕시기, 모노C1 - 6알킬아미노기, 디C1 -6알킬아미노기, 모노C1 - 6알킬아미노카르보닐기, 디C1 - 6알킬아미노카르보닐기, C1 - 6알킬카르보닐아미노기, C1 - 6알킬티오기 또는 C1 - 6알킬설포닐기로 치환되어 있다.)에 의해 구성되는 치환기군을 의미하고,
치환기군 V2는, 치환기군 V1을 구성하는 각 치환기, C1 - 6알킬기 및 C1 - 3할로알킬기에 의해 구성되는 치환기군을 의미하고,
치환기군 Va는, 수산기, 할로겐원자, 시아노기, 니트로기, 아미노기, 카르복시기, 카바모일기, 설파모일기, 포스포노기, 설포기, 테트라졸릴기, 포르메이트기 및 포밀기에 의해 구성되는 치환기군을 의미하고,
R2a, R2b, R3a 및 R3b는, 각각 독립적으로 수소원자, C1 - 3알킬기 또는 C1 - 3할로알킬기인 화합물, 이 화합물의 호변이성체 혹은 그 의약적으로 허용될 수 있는 염 또는 이들의 용매화물.
- 제7항에 있어서,
L1이 단결합이고,
L2와 B가,
L2가 단결합이고, 또한 B가, 4-7원 헤테로사이클릴렌기(이 4-7원 헤테로사이클릴렌기는, 비치환이거나, 또는, 치환기군 V3으로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있을 수도 있고, 또한 이 4-7원 헤테로사이클릴렌기 중 1개의 메틸렌기는, 1,1-C3 - 7시클로알킬렌기로 치환될 수도 있다.)이거나,
또는, L2가 NR2c, O 또는 C1 -6알킬렌기(이 C1 - 6알킬렌기 중 1개의 메틸렌기는, O 또는 NR3c로 치환되어 있을 수도 있다.)이고, 또한 B가, C3 - 6시클로알킬렌기, C3 - 6시클로알케닐렌기 또는 4-7원 헤테로사이클릴렌기(이 C3 - 6시클로알킬렌기, C3 - 6시클로알케닐렌기 및 4-7원 헤테로사이클릴렌기는, 비치환이거나, 또는, 치환기군 V3으로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있을 수도 있고, 또한 이 C3 - 6시클로알킬렌기, C3 - 6시클로알케닐렌기 및 4-7원 헤테로사이클릴렌기 중 1개의 메틸렌기는, 1,1-C3-7시클로알킬렌기로 치환될 수도 있다.)이고,
치환기군 V3는, 수산기, 할로겐원자, 시아노기, 니트로기, C1 - 6알킬기, C1 - 6할로알킬기, C3 -6시클로알킬기, C1 - 6알콕시기 및 C1 - 6할로알콕시기에 의해 구성되는 치환기군을 의미하고,
R2c 및 R3c는, 각각 독립적으로 수소원자, C1 - 3알킬기 또는 C1 - 3할로알킬기인 화합물, 이 화합물의 호변이성체 혹은 그 의약적으로 허용될 수 있는 염 또는 이들의 용매화물.
- 제1항 내지 제6항 중 어느 한 항에 있어서,
L1이 단결합이고,
L2와 B가,
L2가 단결합이고, 또한 B가, 4-7원 헤테로사이클릴렌기(이 4-7원 헤테로사이클릴렌기는, 아미노기, 모노C1 - 6알킬아미노기, 디C1 - 6알킬아미노기 또는 C1 - 6알킬설포닐아미노기로부터 선택되는 치환기로 치환되어 있으며, 또한, 치환기군 V3으로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있을 수도 있고, 또한 이 4-7원 헤테로사이클릴렌기 중 1개의 메틸렌기는, 1,1-C3 - 7시클로알킬렌기로 치환될 수도 있다.)이거나,
또는, L2가 NR2c, O 또는 C1 -6알킬렌기(이 C1 - 6알킬렌기 중 1개의 메틸렌기는, O 또는 NR3c로 치환되어 있을 수도 있다.)이고, 또한 B가, C3 - 6시클로알킬렌기, C3 - 6시클로알케닐렌기 또는 4-7원 헤테로사이클릴렌기(이 C3 - 6시클로알킬렌기, C3 - 6시클로알케닐렌기 및 4-7원 헤테로사이클릴렌기는, 아미노기, 모노C1 - 6알킬아미노기, 디C1 - 6알킬아미노기 또는 C1 - 6알킬설포닐아미노기로부터 선택되는 치환기로 치환되어 있으며, 또한, 치환기군 V3으로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있을 수도 있고, 또한 이 C3 - 6시클로알킬렌기, C3 - 6시클로알케닐렌기 및 4-7원 헤테로사이클릴렌기 중 1개의 메틸렌기는, 1,1-C3 - 7시클로알킬렌기로 치환될 수도 있다.)이고,
치환기군 V3은, 수산기, 할로겐원자, 시아노기, 니트로기, C1 - 6알킬기, C1 - 6할로알킬기, C3 - 6시클로알킬기, C1 - 6알콕시기 및 C1 - 6할로알콕시기에 의해 구성되는 치환기군을 의미하고,
R2c 및 R3c는, 각각 독립적으로 수소원자, C1 - 3알킬기 또는 C1 - 3할로알킬기인 화합물, 이 화합물의 호변이성체 혹은 그 의약적으로 허용될 수 있는 염 또는 이들의 용매화물.
- 제1항 내지 제9항 중 어느 한 항에 있어서,
D가, 3-11원 헤테로사이클릴기, C6 - 14아릴기 또는 5-10원 헤테로아릴기(이 3-11원 헤테로사이클릴기, C6 - 14아릴기 및 5-10원 헤테로아릴기는, 비치환이거나, 또는 치환기군 V5로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.)이고,
치환기군 V5는, 수산기, 할로겐원자, 시아노기, 니트로기, C1 - 6알킬기, C1 - 6알콕시기, C1 - 6알킬티오기, C1 -6알콕시카르보닐기(이 C1 - 6알킬기, C1 - 6알콕시기, C1 - 6알킬티오기 및 C1 - 6알콕시카르보닐기는, 비치환이거나, 또는 치환기군 V1로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.), C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3 - 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, C3 - 6시클로알킬기, 4-7원 헤테로사이클릴기, 페닐기 및 5-6원 헤테로아릴기(이 C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3 - 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, C3 - 6시클로알킬기, 4-7원 헤테로사이클릴기, 페닐기 및 5-6원 헤테로아릴기는, 비치환이거나, 또는 치환기군 V2로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.)에 의해 구성되는 치환기군을 의미하고,
치환기군 V1은, 치환기군 Va를 구성하는 각 치환기, C1 - 6알콕시기, C1 - 3할로알콕시기, 모노C1- 6알킬아미노기, 디C1 - 6알킬아미노기, 모노C1 - 6알킬아미노카르보닐기, 디C1 - 6알킬아미노카르보닐기, C1 - 6알킬카르보닐아미노기, C1 - 6알킬티오기, C1 - 6알킬설포닐기, C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3 - 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, 3-11원 헤테로사이클릴기, C6 - 14아릴기 또는 5-10원 헤테로아릴기(이 C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3- 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, 3-11원 헤테로사이클릴기, C6 - 14아릴기 및 5-10원 헤테로아릴기는, 비치환이거나, 또는 수산기, 할로겐원자, 시아노기, 니트로기, 아미노기, 카르복시기, 카바모일기, 설파모일기, 포스포노기, 포스피노일기, 설포기, 설피노기, 테트라졸릴기, 포밀기, C1-6알킬기, C1 - 3할로알킬기, C1 - 6알콕시기, C1 - 3할로알콕시기, 모노C1 - 6알킬아미노기, 디C1 -6알킬아미노기, 모노C1 - 6알킬아미노카르보닐기, 디C1 - 6알킬아미노카르보닐기, C1 - 6알킬카르보닐아미노기, C1 - 6알킬티오기 또는 C1 - 6알킬설포닐기로 치환되어 있다.)에 의해 구성되는 치환기군을 의미하고,
치환기군 V2는, 치환기군 V1을 구성하는 각 치환기, C1 - 6알킬기 및 C1 - 3할로알킬기에 의해 구성되는 치환기군을 의미하고,
치환기군 Va는, 수산기, 할로겐원자, 시아노기, 니트로기, 아미노기, 카르복시기, 카바모일기, 설파모일기, 포스포노기, 설포기, 테트라졸릴기, 포르메이트기 및 포밀기에 의해 구성되는 치환기군을 의미하는 화합물, 이 화합물의 호변이성체 혹은 그 의약적으로 허용될 수 있는 염 또는 이들의 용매화물.
- 제10항에 있어서,
D가, 4-7원 헤테로사이클릴기, 페닐기 또는 5-6원 헤테로아릴기(이 4-7원 헤테로사이클릴기, 페닐기 및 5-6원 헤테로아릴기는 비치환이거나, 또는 치환기군 V4로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.)이고,
치환기군 V4는, 수산기, 할로겐원자, 시아노기, 니트로기, C1 - 6알킬기, C1 - 6할로알킬기, C1 - 6알콕시기, C1 - 6할로알콕시기, C3 - 6시클로알킬기, C3 - 6시클로알콕시기, 모노C3- 6시클로알킬아미노기, 디C3 - 6시클로알킬아미노기 및 C3 -6시클로알킬티오기(이 C1 -6알킬기, C1 - 6알콕시기, C3 - 6시클로알킬기, C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3 - 6시클로알킬아미노기 및 C3 - 6시클로알킬티오기는, 비치환이거나, 또는 수산기, 아미노기, 니트로기, 시아노기, 3-11원 헤테로사이클릴기, C6 - 14아릴기 또는 5-10원 헤테로아릴기(이 3-11원 헤테로사이클릴기, C6 - 14아릴기 및 5-10원 헤테로아릴기는, 비치환이거나, 또는 카르복시기, 카바모일기, 설파모일기, 포스포노기, 설포기, 테트라졸릴기, 포밀기, 니트로기, 시아노기, 할로겐원자, 수산기, 아미노기, C1-6알킬기, C1 - 3할로알킬기, C1 - 6알콕시기, C1 - 3할로알콕시기, 모노C1 - 6알킬아미노기, 디C1- 6알킬아미노기, 모노C1 - 6알킬아미노카르보닐기, 디C1 - 6알킬아미노카르보닐기, C1 - 6알킬카르보닐아미노기, C1 - 6알킬티오기 또는 C1 - 6알킬설포닐기로 치환되어 있다.)로 치환되어 있다.)에 의해 구성되는 치환기군을 의미하는 화합물, 이 화합물의 호변이성체 혹은 그 의약적으로 허용될 수 있는 염 또는 이들의 용매화물.
- 제11항에 있어서,
D가, 페닐기 또는 5-6원 헤테로아릴기(이 페닐기 또는 5-6원 헤테로아릴기는, 비치환이거나, 또는 할로겐원자, 니트로기, C1 - 6알킬기, C1 - 6할로알킬기, C1 - 6알콕시기 또는 C1 - 6할로알콕시기로 치환되어 있다.)인 화합물, 이 화합물의 호변이성체 혹은 그 의약적으로 허용될 수 있는 염 또는 이들의 용매화물.
- 제1항 내지 제9항 중 어느 한 항에 있어서,
D가, 페닐기 또는 5-6원 헤테로아릴기(이 페닐기 또는 5-6원 헤테로아릴기는, 1개 이상의 C1 - 6알킬설포닐아미노기 또는 C1 -6알킬설포닐옥시기(이 C1 - 6알킬설포닐아미노기 및 C1-6알킬설포닐옥시기는 비치환이거나, 또는 할로겐원자, 니트로기, C1 - 6알콕시기 또는 C1-6할로알콕시기로 치환되어 있다.)로 치환되어 있으며, 할로겐원자, 니트로기, C1 - 6알킬기, C1 - 6할로알킬기, C1 - 6알콕시기 또는 C1 - 6할로알콕시기로 치환되어 있을 수도 있다.)인 화합물, 이 화합물의 호변이성체 혹은 그 의약적으로 허용될 수 있는 염 또는 이들의 용매화물.
- 제13항에 있어서,
D가, 5-6원 헤테로아릴기(이 5-6원 헤테로아릴기는, C1 -6알킬설포닐옥시기(이 C1-6알킬설포닐옥시기는 비치환이거나, 또는 할로겐원자, 니트로기, C1 - 6알콕시기 또는 C1 - 6할로알콕시기로 치환되어 있다.)로 치환되어 있다.)인 화합물, 이 화합물의 호변이성체 혹은 그 의약적으로 허용될 수 있는 염 또는 이들의 용매화물.
- 제1항 내지 제14항 중 어느 한 항에 있어서,
A가, 3-11원 헤테로사이클릴기, C6 - 14아릴기 또는 5-10원 헤테로아릴기(이 3-11원 헤테로사이클릴기, C6 - 14아릴기 및 5-10원 헤테로아릴기는 비치환이거나, 또는 치환기군 V5로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.)이고,
치환기군 V5는, 수산기, 할로겐원자, 시아노기, 니트로기, C1 - 6알킬기, C1 - 6알콕시기, C1 - 6알킬티오기, C1 -6알콕시카르보닐기(이 C1 - 6알킬기, C1 - 6알콕시기, C1 - 6알킬티오기 및 C1 - 6알콕시카르보닐기는, 비치환이거나, 또는 치환기군 V1로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.), C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3 - 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, C3 - 6시클로알킬기, 4-7원 헤테로사이클릴기, 페닐기 및 5-6원 헤테로아릴기(이 C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3 - 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, C3 - 6시클로알킬기, 4-7원 헤테로사이클릴기, 페닐기 및 5-6원 헤테로아릴기는, 비치환이거나, 또는 치환기군 V2로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.)에 의해 구성되는 치환기군을 의미하고,
치환기군 V1은, 치환기군 Va를 구성하는 각 치환기, C1 - 6알콕시기, C1 - 3할로알콕시기, 모노C1- 6알킬아미노기, 디C1 - 6알킬아미노기, 모노C1 - 6알킬아미노카르보닐기, 디C1 - 6알킬아미노카르보닐기, C1 - 6알킬카르보닐아미노기, C1 - 6알킬티오기, C1 - 6알킬설포닐기, C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3 - 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, 3-11원 헤테로사이클릴기, C6 - 14아릴기 또는 5-10원 헤테로아릴기(이 C3 - 6시클로알콕시기, 모노C3 - 6시클로알킬아미노기, 디C3- 6시클로알킬아미노기, C3 - 6시클로알킬카르보닐기, C3 - 6시클로알킬설포닐기, C3 - 6시클로알킬티오기, 3-11원 헤테로사이클릴기, C6 - 14아릴기 및 5-10원 헤테로아릴기는, 비치환이거나, 또는 수산기, 할로겐원자, 시아노기, 니트로기, 아미노기, 카르복시기, 카바모일기, 설파모일기, 포스포노기, 포스피노일기, 설포기, 설피노기, 테트라졸릴기, 포밀기, C1-6알킬기, C1 - 3할로알킬기, C1 - 6알콕시기, C1 - 3할로알콕시기, 모노C1 - 6알킬아미노기, 디C1 -6알킬아미노기, 모노C1 - 6알킬아미노카르보닐기, 디C1 - 6알킬아미노카르보닐기, C1 - 6알킬카르보닐아미노기, C1 - 6알킬티오기 또는 C1 - 6알킬설포닐기로 치환되어 있다.)에 의해 구성되는 치환기군을 의미하고,
치환기군 V2는, 치환기군 V1을 구성하는 각 치환기, C1 - 6알킬기 및 C1 - 3할로알킬기에 의해 구성되는 치환기군을 의미하고,
치환기군 Va는, 수산기, 할로겐원자, 시아노기, 니트로기, 아미노기, 카르복시기, 카바모일기, 설파모일기, 포스포노기, 설포기, 테트라졸릴기, 포르메이트기 및 포밀기에 의해 구성되는 치환기군을 의미하는 화합물, 이 화합물의 호변이성체 혹은 그 의약적으로 허용될 수 있는 염 또는 이들의 용매화물.
- 제15항에 있어서,
A가, 페닐기 또는 5-6원 헤테로아릴기(이 페닐기 및 5-6원 헤테로아릴기는, 비치환이거나, 또는 치환기군 V3으로부터 단독으로 혹은 상이하게 선택되는 1개 이상의 치환기로 치환되어 있다.)이고,
치환기군 V3은, 수산기, 할로겐원자, 시아노기, 니트로기, C1 - 6알킬기, C1 - 6할로알킬기, C3 - 6시클로알킬기, C1 - 6알콕시기 및 C1 - 6할로알콕시기에 의해 구성되는 치환기군을 의미하는 화합물, 이 화합물의 호변이성체 혹은 그 의약적으로 허용될 수 있는 염 또는 이들의 용매화물.
- 제1항 내지 제16항 중 어느 한 항에 기재된 화합물, 이 화합물의 호변이성체 혹은 그 의약적으로 허용될 수 있는 염 또는 이들의 용매화물을 유효성분으로서 함유하는 T형 칼슘채널 저해제.
- 제17항에 기재된 T형 칼슘채널 저해제를 유효성분으로서 함유하는 T형 칼슘채널 저해작용이 유효한 질환의 예방, 치료 및/또는 개선약.
- 제18항에 기재된 T형 칼슘채널 저해제를 유효성분으로서 함유하는 신경장애성 동통치료약.
- 제1항 내지 제19항 중 어느 한 항에 기재된 화합물, 이 화합물의 호변이성체 혹은 그 의약적으로 허용될 수 있는 염 또는 이들의 용매화물을 유효성분으로서 함유하는 의약.
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