TWI689510B - 4-氮雜吲哚化合物 - Google Patents

Info

Publication number

TWI689510B

TWI689510B TW107145397A TW107145397A TWI689510B TW I689510 B TWI689510 B TW I689510B TW 107145397 A TW107145397 A TW 107145397A TW 107145397 A TW107145397 A TW 107145397A TW I689510 B TWI689510 B TW I689510B

Authority

TW

Taiwan

Prior art keywords

pyridin

pyrrolo

triazolo

isopropyl

dimethyl

Prior art date

2017-12-18

Links

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• -1 4-azaindole compound Chemical class 0.000 title claims description 698
• 150000001875 compounds Chemical class 0.000 claims abstract description 238
• 150000003839 salts Chemical class 0.000 claims abstract description 82
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 38
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 26
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 18
• 125000000217 alkyl group Chemical group 0.000 claims description 355
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 197
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 181
• 125000003386 piperidinyl group Chemical group 0.000 claims description 172
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 165
• 125000002757 morpholinyl group Chemical group 0.000 claims description 138
• 125000004193 piperazinyl group Chemical group 0.000 claims description 127
• 125000004076 pyridyl group Chemical group 0.000 claims description 127
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 120
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 117
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 101
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 95
• 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 87
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 85
• 125000001424 substituent group Chemical group 0.000 claims description 84
• 229910052799 carbon Inorganic materials 0.000 claims description 83
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 81
• 125000002393 azetidinyl group Chemical group 0.000 claims description 73
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 71
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 70
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 64
• 125000003566 oxetanyl group Chemical group 0.000 claims description 63
• 229910052757 nitrogen Inorganic materials 0.000 claims description 59
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 57
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 54
• 229910052801 chlorine Inorganic materials 0.000 claims description 51
• 125000001425 triazolyl group Chemical group 0.000 claims description 49
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
• 229910052731 fluorine Inorganic materials 0.000 claims description 46
• 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 46
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 45
• 125000000623 heterocyclic group Chemical group 0.000 claims description 43
• 229910052739 hydrogen Inorganic materials 0.000 claims description 42
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 39
• IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 38
• 201000006417 multiple sclerosis Diseases 0.000 claims description 37
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 37
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 37
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 35
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 34
• 125000002883 imidazolyl group Chemical group 0.000 claims description 34
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 33
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 33
• 125000003545 alkoxy group Chemical group 0.000 claims description 30
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 30
• 238000006467 substitution reaction Methods 0.000 claims description 29
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 29
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 27
• 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 27
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 26
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 24
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
• 125000003944 tolyl group Chemical group 0.000 claims description 23
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
• 125000005936 piperidyl group Chemical group 0.000 claims description 22
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 21
• 238000011282 treatment Methods 0.000 claims description 20
• 125000004432 carbon atom Chemical group C* 0.000 claims description 19
• 125000004122 cyclic group Chemical group 0.000 claims description 18
• 125000000335 thiazolyl group Chemical group 0.000 claims description 18
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 17
• 125000002541 furyl group Chemical group 0.000 claims description 16
• 125000002971 oxazolyl group Chemical group 0.000 claims description 16
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 14
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 14
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• 239000003937 drug carrier Substances 0.000 claims description 13
• 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 12
• 125000005843 halogen group Chemical group 0.000 claims description 12
• 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims description 12
• 125000003118 aryl group Chemical group 0.000 claims description 11
• 125000003725 azepanyl group Chemical group 0.000 claims description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 9
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 8
• 125000005946 imidazo[1,2-a]pyridyl group Chemical group 0.000 claims description 8
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 8
• 125000001041 indolyl group Chemical group 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 8
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 8
• 125000003410 quininyl group Chemical group 0.000 claims description 8
• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 8
• 229930185107 quinolinone Natural products 0.000 claims description 8
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 8
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 7
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 7
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
• 125000001984 thiazolidinyl group Chemical group 0.000 claims description 7
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 6
• 125000006393 methylpyrimidinyl group Chemical group 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 5
• HTFTXLAPNIJIAM-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)=O)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)=O)C(C)C)N=CN=2)C HTFTXLAPNIJIAM-UHFFFAOYSA-N 0.000 claims description 5
• FDPKMJDUXJFKOI-UHFFFAOYSA-N azetidin-3-amine Chemical compound NC1CNC1 FDPKMJDUXJFKOI-UHFFFAOYSA-N 0.000 claims description 5
• 208000037976 chronic inflammation Diseases 0.000 claims description 5
• 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 5
• 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 5
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 5
• QVVKJPXSMTYLGY-UHFFFAOYSA-N 2,3-diazaspiro[4.5]decan-4-one Chemical compound O=C1NNCC11CCCCC1 QVVKJPXSMTYLGY-UHFFFAOYSA-N 0.000 claims description 4
• 125000002619 bicyclic group Chemical group 0.000 claims description 4
• QPMLSUSACCOBDK-UHFFFAOYSA-N diazepane Chemical compound C1CCNNCC1 QPMLSUSACCOBDK-UHFFFAOYSA-N 0.000 claims description 4
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 4
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 3
• 208000021386 Sjogren Syndrome Diseases 0.000 claims description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 3
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 2
• PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical group CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 2
• 125000003277 amino group Chemical group 0.000 claims description 2
• 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 2
• 229910052736 halogen Inorganic materials 0.000 claims description 2
• 150000002367 halogens Chemical class 0.000 claims description 2
• 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 claims description 2
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 45
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 42
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 28
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 20
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 18
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 14
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 11
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 9
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 8
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 8
• 229940080818 propionamide Drugs 0.000 claims 8
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 7
• OJEOJUQOECNDND-UHFFFAOYSA-N oxetan-3-amine Chemical compound NC1COC1 OJEOJUQOECNDND-UHFFFAOYSA-N 0.000 claims 7
• UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 7
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 6
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 5
• 125000001821 azanediyl group Chemical group [H]N(*)* 0.000 claims 4
• BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims 4
• AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 3
• FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 3
• BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims 2
• NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims 2
• AAFUNFZRUWOWNY-UHFFFAOYSA-N C(C)(C)C1=C(NC=2C1=NC(=CC=2)C1CC(CC1)NCC(=O)NC)C=1C=C(C=2N(C=1)N=CN=2)OC Chemical compound C(C)(C)C1=C(NC=2C1=NC(=CC=2)C1CC(CC1)NCC(=O)NC)C=1C=C(C=2N(C=1)N=CN=2)OC AAFUNFZRUWOWNY-UHFFFAOYSA-N 0.000 claims 2
• RCFXDLXTECFJHV-UHFFFAOYSA-N C(C)(C)C1=C(NC=2C1=NC(=CC=2)C1CCC(CC1)NC1COC1)C=1C=C(C=2N(C=1)N=CN=2)CO Chemical compound C(C)(C)C1=C(NC=2C1=NC(=CC=2)C1CCC(CC1)NC1COC1)C=1C=C(C=2N(C=1)N=CN=2)CO RCFXDLXTECFJHV-UHFFFAOYSA-N 0.000 claims 2
• MGQWXJYBYCCPFY-UHFFFAOYSA-N C(C)(C)C1=C(NC=2C1=NC(=CC=2)N1CCC(CC1)N(CC#N)CC#N)C1=CN(C2=NC=CC=C21)C Chemical compound C(C)(C)C1=C(NC=2C1=NC(=CC=2)N1CCC(CC1)N(CC#N)CC#N)C1=CN(C2=NC=CC=C21)C MGQWXJYBYCCPFY-UHFFFAOYSA-N 0.000 claims 2
• RBZWTCIHAKJEDZ-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N(CC(=O)N(C)C)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N(CC(=O)N(C)C)C)C(C)C)N=CN=2)C RBZWTCIHAKJEDZ-UHFFFAOYSA-N 0.000 claims 2
• CXPNJFQHRUEUQN-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC(C1)(C)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC(C1)(C)C)C(C)C)N=CN=2)C CXPNJFQHRUEUQN-UHFFFAOYSA-N 0.000 claims 2
• ZOTZMNTUGLUSMA-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC(C1)O)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC(C1)O)C(C)C)N=CN=2)C ZOTZMNTUGLUSMA-UHFFFAOYSA-N 0.000 claims 2
• YXNTWYWGKJPMHA-UHFFFAOYSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC(CC1)F)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1CC(CC1)F)C(C)C)N=CN=2)C YXNTWYWGKJPMHA-UHFFFAOYSA-N 0.000 claims 2
• JAQSIZGGMMEOBU-LZBANZJXSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1[C@H](CCC1)CO)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)C1CCC(CC1)N1[C@H](CCC1)CO)C(C)C)N=CN=2)C JAQSIZGGMMEOBU-LZBANZJXSA-N 0.000 claims 2
• FAZBTGNEPSTMLA-HZPDHXFCSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H](N(C[C@H]1C)CC(=O)N)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H](N(C[C@H]1C)CC(=O)N)C)C(C)C)N=CN=2)C FAZBTGNEPSTMLA-HZPDHXFCSA-N 0.000 claims 2
• XFOUAKVFHFXIBY-INIZCTEOSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H](NCC1)CO)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H](NCC1)CO)C(C)C)N=CN=2)C XFOUAKVFHFXIBY-INIZCTEOSA-N 0.000 claims 2
• AHRRVLMWZSFVJS-UHFFFAOYSA-N FC1CN(CC1)C1CCC(CC1)C1=CC=C2C(=N1)C(=C(N2)C=1C=C(C=2N(C=1)N=CN=2)OC)C(C)C Chemical compound FC1CN(CC1)C1CCC(CC1)C1=CC=C2C(=N1)C(=C(N2)C=1C=C(C=2N(C=1)N=CN=2)OC)C(C)C AHRRVLMWZSFVJS-UHFFFAOYSA-N 0.000 claims 2
• 241000237858 Gastropoda Species 0.000 claims 2
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-methylmorpholine Substances CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
• 239000007983 Tris buffer Substances 0.000 claims 2
• HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 2
• 229960004979 fampridine Drugs 0.000 claims 2
• TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
• QAVIPYUSPQRVKA-UHFFFAOYSA-N 1,2-diazaspiro[3.3]heptane Chemical compound C1CCC21NNC2 QAVIPYUSPQRVKA-UHFFFAOYSA-N 0.000 claims 1
• BNBLWPUWMNURAX-UHFFFAOYSA-N 1-(2-methylpropyl)piperidine Chemical compound CC(C)CN1CCCCC1 BNBLWPUWMNURAX-UHFFFAOYSA-N 0.000 claims 1
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• HNTSNYWUJWEOJR-FCHUYYIVSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H](N(C[C@@H]1C)C(CCN1CC3(COC3)CC1)=O)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1C[C@H](N(C[C@@H]1C)C(CCN1CC3(COC3)CC1)=O)C)C(C)C)N=CN=2)C HNTSNYWUJWEOJR-FCHUYYIVSA-N 0.000 claims 1
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• JRQBGHVFZNENAQ-RTBURBONSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1[C@@H](CN(C[C@H]1C)C(CCN(C)C)=O)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1[C@@H](CN(C[C@H]1C)C(CCN(C)C)=O)C)C(C)C)N=CN=2)C JRQBGHVFZNENAQ-RTBURBONSA-N 0.000 claims 1
• JSZWPOMQZDSWOX-HZPDHXFCSA-N CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1[C@@H](CN(C[C@H]1C)CC(=O)N)C)C(C)C)N=CN=2)C Chemical compound CC1=C(C=2N(C=C1C1=C(C3=NC(=CC=C3N1)N1[C@@H](CN(C[C@H]1C)CC(=O)N)C)C(C)C)N=CN=2)C JSZWPOMQZDSWOX-HZPDHXFCSA-N 0.000 claims 1
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