RU2359970C2 - Производные бензимидазола, бензотиазола и бензоксазола и их применение в качестве модуляторов lta4h - Google Patents

Info

Publication number

RU2359970C2

RU2359970C2 RU2006102508/04A RU2006102508A RU2359970C2 RU 2359970 C2 RU2359970 C2 RU 2359970C2 RU 2006102508/04 A RU2006102508/04 A RU 2006102508/04A RU 2006102508 A RU2006102508 A RU 2006102508A RU 2359970 C2 RU2359970 C2 RU 2359970C2

Authority

RU

Russia

Prior art keywords

yloxy

benzothiazol

benzyl

piperidin

group

Prior art date

2003-07-28

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• Global Dossier
• Discuss

• BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title 1
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 398
• 238000000034 method Methods 0.000 claims abstract description 259
• -1 4-{[(2-aminocyclobutancarbonyl)amino]methyl}piperidine-1-yl Chemical group 0.000 claims abstract description 238
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 117
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 75
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 60
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 42
• 102100022118 Leukotriene A-4 hydrolase Human genes 0.000 claims abstract description 39
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 37
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 30
• 150000003839 salts Chemical class 0.000 claims abstract description 30
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
• 125000004122 cyclic group Chemical group 0.000 claims abstract description 16
• 125000004193 piperazinyl group Chemical group 0.000 claims abstract description 15
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 14
• 230000001404 mediated effect Effects 0.000 claims abstract description 14
• 125000003118 aryl group Chemical group 0.000 claims abstract description 12
• 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 12
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 11
• 208000006673 asthma Diseases 0.000 claims abstract description 11
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 11
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 10
• 201000004681 Psoriasis Diseases 0.000 claims abstract description 10
• 230000000694 effects Effects 0.000 claims abstract description 10
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
• 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 10
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
• 229910052727 yttrium Inorganic materials 0.000 claims abstract description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
• 125000004429 atom Chemical group 0.000 claims abstract description 7
• 229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
• 150000002367 halogens Chemical class 0.000 claims abstract description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 5
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 4
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims abstract description 4
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 3
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 3
• 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
• 125000003368 amide group Chemical group 0.000 claims abstract description 3
• 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 3
• 201000006417 multiple sclerosis Diseases 0.000 claims abstract 5
• 125000000217 alkyl group Chemical group 0.000 claims description 96
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 60
• 125000001424 substituent group Chemical group 0.000 claims description 46
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 37
• 229920006395 saturated elastomer Polymers 0.000 claims description 34
• 206010061218 Inflammation Diseases 0.000 claims description 33
• 230000004054 inflammatory process Effects 0.000 claims description 33
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 30
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 27
• 150000002148 esters Chemical class 0.000 claims description 23
• 229940126065 leukotriene A4 hydrolase inhibitor Drugs 0.000 claims description 20
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
• KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 16
• 201000010099 disease Diseases 0.000 claims description 15
• MBGDQOYOKOUJOX-UHFFFAOYSA-N 1-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-4-hydroxypyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 MBGDQOYOKOUJOX-UHFFFAOYSA-N 0.000 claims description 13
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 13
• 150000001721 carbon Chemical group 0.000 claims description 13
• 230000002401 inhibitory effect Effects 0.000 claims description 11
• CFTXJKKITUELKJ-UHFFFAOYSA-N 1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 CFTXJKKITUELKJ-UHFFFAOYSA-N 0.000 claims description 10
• BUZBVOKDNAZIIM-UHFFFAOYSA-N 1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 BUZBVOKDNAZIIM-UHFFFAOYSA-N 0.000 claims description 10
• ZVDOMASQJBYMSO-UHFFFAOYSA-N 2-[4-(piperidin-1-ylmethyl)phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1CN1CCCCC1 ZVDOMASQJBYMSO-UHFFFAOYSA-N 0.000 claims description 10
• UBVVZACYWWPTID-UHFFFAOYSA-N 1-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]pyrrolidin-2-one Chemical compound O=C1CCCN1C1CCN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 UBVVZACYWWPTID-UHFFFAOYSA-N 0.000 claims description 9
• CREOVZBMIBKVON-UHFFFAOYSA-N 1-[2-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-cyclopropylamino]ethyl]-4-hydroxypyrrolidin-2-one Chemical compound O=C1CC(O)CN1CCN(C1CC1)CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 CREOVZBMIBKVON-UHFFFAOYSA-N 0.000 claims description 9
• WNCUSFCVRSUOKM-UHFFFAOYSA-N 2-[2-fluoro-4-(piperidin-1-ylmethyl)phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C(F)=CC=1CN1CCCCC1 WNCUSFCVRSUOKM-UHFFFAOYSA-N 0.000 claims description 9
• MOWJCGXXGLULBX-UHFFFAOYSA-N 3-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-1,3-oxazolidin-2-one Chemical compound O=C1OCCN1C1CCN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 MOWJCGXXGLULBX-UHFFFAOYSA-N 0.000 claims description 9
• YNNJLQSGXCRFPI-UHFFFAOYSA-N 4-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]morpholin-3-one Chemical compound O=C1COCCN1C1CCN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 YNNJLQSGXCRFPI-UHFFFAOYSA-N 0.000 claims description 9
• HGFOHZIPFZOTFU-UHFFFAOYSA-N methyl 3-[[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]amino]-3-oxopropanoate Chemical compound COC(CC(NC1CCN(CC1)CC1=CC=C(C=C1)OC=1SC2=C(N=1)C=CC=C2)=O)=O HGFOHZIPFZOTFU-UHFFFAOYSA-N 0.000 claims description 9
• CDIFBWHQJIJSMM-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-n-methylmethanesulfonamide Chemical compound C1CC(N(C)S(C)(=O)=O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 CDIFBWHQJIJSMM-UHFFFAOYSA-N 0.000 claims description 9
• NXAVSLLJRLFRGB-UHFFFAOYSA-N n-[[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]methyl]methanesulfonamide Chemical compound C1CC(CNS(=O)(=O)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 NXAVSLLJRLFRGB-UHFFFAOYSA-N 0.000 claims description 9
• IEPGXTISLYYPRB-UHFFFAOYSA-N n-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]cyclopropanamine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CNC1CC1 IEPGXTISLYYPRB-UHFFFAOYSA-N 0.000 claims description 9
• WWGLNTQTOWLQOA-UHFFFAOYSA-N 1-[3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethylamino]propyl]pyrrolidin-2-one Chemical compound O=C1CCCN1CCCNCCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 WWGLNTQTOWLQOA-UHFFFAOYSA-N 0.000 claims description 8
• IFGDCUJETCFRNO-UHFFFAOYSA-N 1-[4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazin-1-yl]-2,2,2-trifluoroethanone Chemical compound C1CN(C(=O)C(F)(F)F)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 IFGDCUJETCFRNO-UHFFFAOYSA-N 0.000 claims description 8
• ZJXKRDURLOVEJM-UHFFFAOYSA-N 1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]-4-phenylpiperidin-4-ol Chemical compound C1CN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=CC=C1 ZJXKRDURLOVEJM-UHFFFAOYSA-N 0.000 claims description 8
• BTYHUCROUVOSFY-UHFFFAOYSA-N 1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-amine Chemical compound C1CC(N)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 BTYHUCROUVOSFY-UHFFFAOYSA-N 0.000 claims description 8
• ZMQJXJKADGZNSO-UHFFFAOYSA-N 2-[4-(piperazin-1-ylmethyl)phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CN1CCNCC1 ZMQJXJKADGZNSO-UHFFFAOYSA-N 0.000 claims description 8
• JNKRNJIZLGLIJG-UHFFFAOYSA-N 2-[4-(piperidin-1-ylmethyl)phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CN1CCCCC1 JNKRNJIZLGLIJG-UHFFFAOYSA-N 0.000 claims description 8
• VLSBZKOXDMHPMI-UHFFFAOYSA-N 2-[4-[(4-methylsulfonylpiperazin-1-yl)methyl]phenoxy]-1,3-benzothiazole Chemical compound C1CN(S(=O)(=O)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 VLSBZKOXDMHPMI-UHFFFAOYSA-N 0.000 claims description 8
• DOXZGFKDCZAINY-UHFFFAOYSA-N 2-[4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 DOXZGFKDCZAINY-UHFFFAOYSA-N 0.000 claims description 8
• KUMUDRZJCKKLNV-UHFFFAOYSA-N 2-[4-[[4-(2h-tetrazol-5-yl)piperidin-1-yl]methyl]phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CN(CC1)CCC1C1=NN=NN1 KUMUDRZJCKKLNV-UHFFFAOYSA-N 0.000 claims description 8
• ZGSQQPIVBRWTEB-UHFFFAOYSA-N 3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methylamino]propanoic acid Chemical compound C1=CC(CNCCC(=O)O)=CC=C1OC1=NC2=CC=CC=C2S1 ZGSQQPIVBRWTEB-UHFFFAOYSA-N 0.000 claims description 8
• LXFBZMAHNZSEJG-UHFFFAOYSA-N 4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]morpholine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CN1CCOCC1 LXFBZMAHNZSEJG-UHFFFAOYSA-N 0.000 claims description 8
• WXHRYHXKKQDISV-UHFFFAOYSA-N [1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]methanol Chemical compound C1CC(CO)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 WXHRYHXKKQDISV-UHFFFAOYSA-N 0.000 claims description 8
• WUEBHOONQLLWHB-UHFFFAOYSA-N [1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]methylurea Chemical compound C1CC(CNC(=O)N)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 WUEBHOONQLLWHB-UHFFFAOYSA-N 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 8
• QVVWRAAMUPSWRE-UHFFFAOYSA-N ethyl 3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methylamino]propanoate Chemical compound C1=CC(CNCCC(=O)OCC)=CC=C1OC1=NC2=CC=CC=C2S1 QVVWRAAMUPSWRE-UHFFFAOYSA-N 0.000 claims description 8
• GOKWQJTWJSUQNO-UHFFFAOYSA-N methyl n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 GOKWQJTWJSUQNO-UHFFFAOYSA-N 0.000 claims description 8
• ZYPGCBNIVHGWEP-UHFFFAOYSA-N n'-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]-n'-cyclopropylethane-1,2-diamine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CN(CCN)C1CC1 ZYPGCBNIVHGWEP-UHFFFAOYSA-N 0.000 claims description 8
• XAXNYOONBNCDGS-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]methanesulfonamide Chemical compound C1CC(NS(=O)(=O)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 XAXNYOONBNCDGS-UHFFFAOYSA-N 0.000 claims description 8
• YIMRWBVVQPCHFH-UHFFFAOYSA-N n-[[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]methyl]-2,2,2-trifluoroacetamide Chemical compound C1CC(CNC(=O)C(F)(F)F)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 YIMRWBVVQPCHFH-UHFFFAOYSA-N 0.000 claims description 8
• ZMMVYRNLQJITOR-UHFFFAOYSA-N n-[[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]methyl]-2-hydroxyacetamide Chemical compound C1CC(CNC(=O)CO)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 ZMMVYRNLQJITOR-UHFFFAOYSA-N 0.000 claims description 8
• TWQZWNFLIVWQNZ-UHFFFAOYSA-N phenyl n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]carbamate Chemical compound C1CN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1NC(=O)OC1=CC=CC=C1 TWQZWNFLIVWQNZ-UHFFFAOYSA-N 0.000 claims description 8
• VBSFMULSLZYRBF-UHFFFAOYSA-N tert-butyl 4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 VBSFMULSLZYRBF-UHFFFAOYSA-N 0.000 claims description 8
• LFANTSMNOUDSSX-UHFFFAOYSA-N 1-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-1,3-dimethylurea Chemical compound C1CC(N(C)C(=O)NC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 LFANTSMNOUDSSX-UHFFFAOYSA-N 0.000 claims description 7
• VLRQVKLRWATZMA-UHFFFAOYSA-N 1-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-1-methylurea Chemical compound C1CC(N(C)C(N)=O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 VLRQVKLRWATZMA-UHFFFAOYSA-N 0.000 claims description 7
• PVHZEAUQIFRCJQ-UHFFFAOYSA-N 1-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-3-ethylthiourea Chemical compound C1CC(NC(=S)NCC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 PVHZEAUQIFRCJQ-UHFFFAOYSA-N 0.000 claims description 7
• LKTRZJPIGMYCSF-UHFFFAOYSA-N 1-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-3-ethylurea Chemical compound C1CC(NC(=O)NCC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 LKTRZJPIGMYCSF-UHFFFAOYSA-N 0.000 claims description 7
• IXLAMKLSAJZLBI-UHFFFAOYSA-N 1-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-3-methylurea Chemical compound C1CC(NC(=O)NC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 IXLAMKLSAJZLBI-UHFFFAOYSA-N 0.000 claims description 7
• IOQAYYZCMIJSKU-UHFFFAOYSA-N 1-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-3-propan-2-ylurea Chemical compound C1CC(NC(=O)NC(C)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 IOQAYYZCMIJSKU-UHFFFAOYSA-N 0.000 claims description 7
• HEUDZUWKEPAQLK-UHFFFAOYSA-N 1-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-3-propylurea Chemical compound C1CC(NC(=O)NCCC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 HEUDZUWKEPAQLK-UHFFFAOYSA-N 0.000 claims description 7
• MGSCKVOKOPTOSS-UHFFFAOYSA-N 1-[3-[3-[4-(1,3-benzothiazol-2-yloxy)phenyl]propylamino]propyl]pyrrolidin-2-one Chemical compound S1C(=NC2=C1C=CC=C2)OC1=CC=C(CCCNCCCN2C(CCC2)=O)C=C1 MGSCKVOKOPTOSS-UHFFFAOYSA-N 0.000 claims description 7
• WAYPBLZUXMHGFH-UHFFFAOYSA-N 1-[3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-cyclopropylamino]propyl]-3-propan-2-ylurea Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CN(CCCNC(=O)NC(C)C)C1CC1 WAYPBLZUXMHGFH-UHFFFAOYSA-N 0.000 claims description 7
• MYNZGUYSDCRWLJ-UHFFFAOYSA-N 1-[3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-propan-2-ylamino]propyl]pyrrolidin-2-one Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CN(C(C)C)CCCN1CCCC1=O MYNZGUYSDCRWLJ-UHFFFAOYSA-N 0.000 claims description 7
• RPUNWQZSJVRXCM-UHFFFAOYSA-N 1-[3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methylamino]propyl]pyrrolidin-2-one Chemical compound O=C1CCCN1CCCNCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 RPUNWQZSJVRXCM-UHFFFAOYSA-N 0.000 claims description 7
• NUFHDURBLSHZNX-UHFFFAOYSA-N 1-[4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazin-1-yl]-2-hydroxyethanone Chemical compound C1CN(C(=O)CO)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 NUFHDURBLSHZNX-UHFFFAOYSA-N 0.000 claims description 7
• VYSJKECYGOBTEZ-UHFFFAOYSA-N 1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]-n-methylpiperidin-4-amine Chemical compound C1CC(NC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 VYSJKECYGOBTEZ-UHFFFAOYSA-N 0.000 claims description 7
• GQIMPVXUPKIVNS-UHFFFAOYSA-N 2-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-1-hydroxyguanidine Chemical compound C1CC(N=C(NO)N)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 GQIMPVXUPKIVNS-UHFFFAOYSA-N 0.000 claims description 7
• MFJHVGCWPNRKFB-UHFFFAOYSA-N 2-[4-[[4-(sulfamoylamino)piperidin-1-yl]methyl]phenoxy]-1,3-benzothiazole Chemical compound C1CC(NS(=O)(=O)N)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 MFJHVGCWPNRKFB-UHFFFAOYSA-N 0.000 claims description 7
• CFWHBZWTAKPCFW-UHFFFAOYSA-N 2-[[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-methylamino]-2-oxoacetic acid Chemical compound C1CC(N(C)C(=O)C(O)=O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 CFWHBZWTAKPCFW-UHFFFAOYSA-N 0.000 claims description 7
• PCYYPXCCVPPBCQ-UHFFFAOYSA-N 3-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-1,1-dimethylurea Chemical compound C1CC(NC(=O)N(C)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 PCYYPXCCVPPBCQ-UHFFFAOYSA-N 0.000 claims description 7
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• ITGATYKDDNYQGX-UHFFFAOYSA-N CC(CC1CCN(CC(C=C2)=CC=C2OC2=NC(C=CC=C3)=C3S2)CC1)S(N)(=O)=O Chemical compound CC(CC1CCN(CC(C=C2)=CC=C2OC2=NC(C=CC=C3)=C3S2)CC1)S(N)(=O)=O ITGATYKDDNYQGX-UHFFFAOYSA-N 0.000 claims description 7
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• NOTWVENCQZOQIZ-UHFFFAOYSA-N propan-2-yl n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OC(C)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 NOTWVENCQZOQIZ-UHFFFAOYSA-N 0.000 claims description 7
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• HFWIFRRHMZLJNF-UHFFFAOYSA-N 1-[3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-cyclopropylamino]propyl]-4-hydroxypyrrolidin-2-one Chemical compound O=C1CC(O)CN1CCCN(C1CC1)CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 HFWIFRRHMZLJNF-UHFFFAOYSA-N 0.000 claims description 6
• ZSLLLGHNYUBQPU-UHFFFAOYSA-N 1-[3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-cyclopropylamino]propyl]pyrrolidin-2-one Chemical compound O=C1CCCN1CCCN(C1CC1)CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 ZSLLLGHNYUBQPU-UHFFFAOYSA-N 0.000 claims description 6
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• ATWIRLATCCUTSE-UHFFFAOYSA-N 2-[4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazin-1-yl]-1-pyrrolidin-1-ylethanone Chemical compound C1CN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1CC(=O)N1CCCC1 ATWIRLATCCUTSE-UHFFFAOYSA-N 0.000 claims description 6
• KNKPLRVMSFXJDO-UHFFFAOYSA-N 2-[4-[[4-(benzenesulfonyl)piperazin-1-yl]methyl]phenoxy]-1,3-benzothiazole Chemical compound C1CN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1S(=O)(=O)C1=CC=CC=C1 KNKPLRVMSFXJDO-UHFFFAOYSA-N 0.000 claims description 6
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• MMPJZYXYNRYMQR-UHFFFAOYSA-N 4-chloro-2-[4-(piperidin-1-ylmethyl)phenoxy]-1,3-benzothiazole Chemical compound N=1C=2C(Cl)=CC=CC=2SC=1OC(C=C1)=CC=C1CN1CCCCC1 MMPJZYXYNRYMQR-UHFFFAOYSA-N 0.000 claims description 6
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