KR20050006149A - 항콜린제 및 ｐ38 키나아제 억제제를 기본으로 하는신규한 약제학적 조성물 - Google Patents

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Publication number

KR20050006149A

KR20050006149A KR10-2004-7016160A KR20047016160A KR20050006149A KR 20050006149 A KR20050006149 A KR 20050006149A KR 20047016160 A KR20047016160 A KR 20047016160A KR 20050006149 A KR20050006149 A KR 20050006149A

Authority

KR

South Korea

Prior art keywords

alkyl

amino

optionally

phenyl

optionally substituted

Prior art date

2002-04-10

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.)

Withdrawn

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• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 98
• 229940043355 kinase inhibitor Drugs 0.000 title claims abstract description 86
• 239000003757 phosphotransferase inhibitor Substances 0.000 title claims abstract description 86
• 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 title claims abstract description 84
• 239000000812 cholinergic antagonist Substances 0.000 title claims description 3
• 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 title 1
• 238000000034 method Methods 0.000 claims abstract description 8
• 208000023504 respiratory system disease Diseases 0.000 claims abstract description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 955
• -1 1,2,4-triazin-5-yl Chemical group 0.000 claims description 636
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 273
• 125000003545 alkoxy group Chemical group 0.000 claims description 264
• 125000000623 heterocyclic group Chemical group 0.000 claims description 186
• 229910052736 halogen Inorganic materials 0.000 claims description 184
• 150000002367 halogens Chemical class 0.000 claims description 183
• 150000002825 nitriles Chemical class 0.000 claims description 148
• 125000004076 pyridyl group Chemical group 0.000 claims description 144
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 143
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 137
• 125000003118 aryl group Chemical group 0.000 claims description 115
• 229910052717 sulfur Inorganic materials 0.000 claims description 115
• 125000001624 naphthyl group Chemical group 0.000 claims description 113
• 125000001072 heteroaryl group Chemical group 0.000 claims description 102
• 125000002883 imidazolyl group Chemical group 0.000 claims description 101
• 229910052760 oxygen Inorganic materials 0.000 claims description 101
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 84
• 150000001875 compounds Chemical class 0.000 claims description 81
• 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 77
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 74
• 125000004043 oxo group Chemical group O=* 0.000 claims description 73
• 125000002541 furyl group Chemical group 0.000 claims description 71
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 67
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 65
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 65
• 125000005843 halogen group Chemical group 0.000 claims description 64
• 229910052757 nitrogen Inorganic materials 0.000 claims description 57
• 125000001544 thienyl group Chemical group 0.000 claims description 55
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 54
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 54
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 52
• 125000003282 alkyl amino group Chemical group 0.000 claims description 50
• 125000004193 piperazinyl group Chemical group 0.000 claims description 48
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 46
• 239000001257 hydrogen Substances 0.000 claims description 45
• 229910052739 hydrogen Inorganic materials 0.000 claims description 45
• 125000003386 piperidinyl group Chemical group 0.000 claims description 44
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 43
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 41
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 40
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 40
• 125000003435 aroyl group Chemical group 0.000 claims description 38
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 37
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 36
• VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 34
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 34
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 34
• 125000002252 acyl group Chemical group 0.000 claims description 34
• 125000005842 heteroatom Chemical group 0.000 claims description 34
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 32
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 32
• 239000013543 active substance Substances 0.000 claims description 31
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 31
• 125000003342 alkenyl group Chemical group 0.000 claims description 30
• 239000000203 mixture Substances 0.000 claims description 30
• 150000003839 salts Chemical class 0.000 claims description 30
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 30
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 28
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 28
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 28
• 125000000304 alkynyl group Chemical group 0.000 claims description 27
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 27
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 27
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 26
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 26
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 24
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 24
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 24
• 125000001041 indolyl group Chemical group 0.000 claims description 24
• RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 24
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 24
• 239000000843 powder Substances 0.000 claims description 23
• 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 22
• 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims description 22
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 21
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 21
• QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 claims description 20
• VSIYJQNFMOOGCU-UHFFFAOYSA-N 1-(cyclohexen-1-yl)cyclohexene Chemical group C1CCCC(C=2CCCCC=2)=C1 VSIYJQNFMOOGCU-UHFFFAOYSA-N 0.000 claims description 20
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 20
• 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 20
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 20
• 125000001424 substituent group Chemical group 0.000 claims description 20
• 150000002431 hydrogen Chemical group 0.000 claims description 19
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 19
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 18
• 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 18
• 239000003380 propellant Substances 0.000 claims description 18
• 229920006395 saturated elastomer Polymers 0.000 claims description 18
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 17
• 239000000443 aerosol Substances 0.000 claims description 17
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 17
• 229930192474 thiophene Natural products 0.000 claims description 17
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 16
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 16
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 16
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 16
• 125000003107 substituted aryl group Chemical group 0.000 claims description 16
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 15
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 15
• 238000009472 formulation Methods 0.000 claims description 15
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 15
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 15
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 15
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 15
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 14
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 14
• 125000004599 benzpyrazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical class O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 claims description 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 13
• 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 claims description 13
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
• UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 12
• LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 12
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 12
• 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 12
• 125000005046 dihydronaphthyl group Chemical group 0.000 claims description 12
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 12
• 125000002757 morpholinyl group Chemical group 0.000 claims description 12
• 125000004442 acylamino group Chemical group 0.000 claims description 11
• 125000003277 amino group Chemical group 0.000 claims description 11
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
• 239000002775 capsule Substances 0.000 claims description 11
• 125000005879 dioxolanyl group Chemical group 0.000 claims description 11
• 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 10
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 239000001301 oxygen Substances 0.000 claims description 10
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 10
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 10
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 10
• 239000011593 sulfur Substances 0.000 claims description 10
• 125000001425 triazolyl group Chemical group 0.000 claims description 10
• ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims description 9
• MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 claims description 9
• 229960002428 fentanyl Drugs 0.000 claims description 9
• 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 8
• GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 8
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
• 239000002253 acid Substances 0.000 claims description 8
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
• WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 claims description 8
• 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 8
• 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 8
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
• 125000004001 thioalkyl group Chemical group 0.000 claims description 8
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 7
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 7
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 7
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 7
• DELUNUNQVWNZKQ-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ylidenemethanone Chemical compound O=C=C1CC=CC=C1 DELUNUNQVWNZKQ-UHFFFAOYSA-N 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 7
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 7
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 7
• 125000005647 linker group Chemical group 0.000 claims description 7
• 150000003335 secondary amines Chemical class 0.000 claims description 7
• 150000003512 tertiary amines Chemical class 0.000 claims description 7
• RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims description 7
• 150000003536 tetrazoles Chemical class 0.000 claims description 7
• 125000005505 thiomorpholino group Chemical group 0.000 claims description 7
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 6
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 6
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
• OEXHQOGQTVQTAT-JRNQLAHRSA-N ipratropium Chemical class O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 OEXHQOGQTVQTAT-JRNQLAHRSA-N 0.000 claims description 6
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 6
• 239000002245 particle Substances 0.000 claims description 6
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 6
• 239000002904 solvent Substances 0.000 claims description 6
• 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 6
• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 6
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
• FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 5
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 5
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 5
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
• 125000005157 alkyl carboxy group Chemical group 0.000 claims description 5
• 239000007788 liquid Substances 0.000 claims description 5
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 5
• 125000000335 thiazolyl group Chemical group 0.000 claims description 5
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 5
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 5
• NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 claims description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
• KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
• YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims description 4
• 150000001412 amines Chemical class 0.000 claims description 4
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
• 125000002837 carbocyclic group Chemical group 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 150000001768 cations Chemical class 0.000 claims description 4
• DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 4
• 125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 0.000 claims description 4
• HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 4
• 125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
• 125000002950 monocyclic group Chemical group 0.000 claims description 4
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• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
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