JP2007500703A - ベンズイミダゾール、ベンズチアゾールおよびベンゾキサゾール誘導体およびｌｔａ４ｈモジュレーターとしてのそれらの使用 - Google Patents

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Publication number

JP2007500703A

JP2007500703A JP2006521973A JP2006521973A JP2007500703A JP 2007500703 A JP2007500703 A JP 2007500703A JP 2006521973 A JP2006521973 A JP 2006521973A JP 2006521973 A JP2006521973 A JP 2006521973A JP 2007500703 A JP2007500703 A JP 2007500703A

Authority

JP

Japan

Prior art keywords

yloxy

benzothiazol

benzyl

piperidin

alkyl

Prior art date

2003-07-28

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.)

Pending

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• 102100022118 Leukotriene A-4 hydrolase Human genes 0.000 title claims abstract description 44
• 101000619898 Homo sapiens Leukotriene A-4 hydrolase Proteins 0.000 title claims 23
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title description 3
• BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title 1
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title 1
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 68
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 67
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 51
• 206010061218 Inflammation Diseases 0.000 claims abstract description 31
• 230000004054 inflammatory process Effects 0.000 claims abstract description 31
• 229910052731 fluorine Inorganic materials 0.000 claims abstract description 20
• 229910052727 yttrium Inorganic materials 0.000 claims abstract description 19
• 229910052794 bromium Inorganic materials 0.000 claims abstract description 15
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 15
• 229910052740 iodine Inorganic materials 0.000 claims abstract description 14
• 230000000694 effects Effects 0.000 claims abstract description 10
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 8
• 125000000217 alkyl group Chemical group 0.000 claims description 459
• -1 1,3-dihydro-indol-2-one-1-yl Chemical group 0.000 claims description 336
• 150000001875 compounds Chemical class 0.000 claims description 293
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 256
• 238000000034 method Methods 0.000 claims description 250
• 229910052757 nitrogen Inorganic materials 0.000 claims description 161
• 229910052799 carbon Inorganic materials 0.000 claims description 143
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 123
• 125000005842 heteroatom Chemical group 0.000 claims description 121
• 125000001424 substituent group Chemical group 0.000 claims description 111
• 125000000623 heterocyclic group Chemical group 0.000 claims description 72
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 48
• 229920006395 saturated elastomer Polymers 0.000 claims description 44
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
• 239000008194 pharmaceutical composition Substances 0.000 claims description 41
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 32
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 30
• 150000002148 esters Chemical class 0.000 claims description 29
• 150000001408 amides Chemical class 0.000 claims description 28
• 125000004193 piperazinyl group Chemical group 0.000 claims description 27
• 125000001072 heteroaryl group Chemical group 0.000 claims description 25
• 125000003386 piperidinyl group Chemical group 0.000 claims description 25
• 125000005843 halogen group Chemical group 0.000 claims description 23
• 125000003118 aryl group Chemical group 0.000 claims description 22
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 230000008569 process Effects 0.000 claims description 19
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 18
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 125000004122 cyclic group Chemical group 0.000 claims description 16
• 125000000304 alkynyl group Chemical group 0.000 claims description 15
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 14
• 125000003342 alkenyl group Chemical group 0.000 claims description 14
• 230000001404 mediated effect Effects 0.000 claims description 14
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 12
• 208000006673 asthma Diseases 0.000 claims description 12
• 101150008896 hetR gene Proteins 0.000 claims description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 12
• 201000001320 Atherosclerosis Diseases 0.000 claims description 11
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 11
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 11
• 201000004681 Psoriasis Diseases 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 11
• 239000012453 solvate Substances 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
• 201000006417 multiple sclerosis Diseases 0.000 claims description 9
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
• 150000001721 carbon Chemical group 0.000 claims description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
• 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims description 6
• 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 6
• 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 6
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• IQTADKJWOJRVNV-UHFFFAOYSA-N 2-(4-ethylphenoxy)-1,3-benzothiazole Chemical compound C1=CC(CC)=CC=C1OC1=NC2=CC=CC=C2S1 IQTADKJWOJRVNV-UHFFFAOYSA-N 0.000 claims description 6
• GCSDZVIXDKZKFO-UHFFFAOYSA-N 2-(4-ethylphenoxy)-1,3-benzoxazole Chemical compound C1=CC(CC)=CC=C1OC1=NC2=CC=CC=C2O1 GCSDZVIXDKZKFO-UHFFFAOYSA-N 0.000 claims description 6
• HGLXZYVILQDPRO-UHFFFAOYSA-N 2-(4-ethylphenoxy)-1h-benzimidazole Chemical compound C1=CC(CC)=CC=C1OC1=NC2=CC=CC=C2N1 HGLXZYVILQDPRO-UHFFFAOYSA-N 0.000 claims description 6
• 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 6
• ZVDOMASQJBYMSO-UHFFFAOYSA-N 2-[4-(piperidin-1-ylmethyl)phenoxy]-1,3-benzoxazole Chemical group C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1CN1CCCCC1 ZVDOMASQJBYMSO-UHFFFAOYSA-N 0.000 claims description 6
• PBYPGZHIAKLYFN-UHFFFAOYSA-N 3,9-diazaspiro[5.5]undecane-3-carboxylic acid Chemical compound C1CN(C(=O)O)CCC11CCNCC1 PBYPGZHIAKLYFN-UHFFFAOYSA-N 0.000 claims description 6
• 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 6
• IQTFFIWZQWGCCE-UHFFFAOYSA-N 4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazine-1-carboxylic acid Chemical compound C1CN(C(=O)O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 IQTFFIWZQWGCCE-UHFFFAOYSA-N 0.000 claims description 6
• ZTKMACRGUPTAGN-UHFFFAOYSA-N [1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-methylcarbamic acid Chemical compound S1C(=NC2=C1C=CC=C2)OC2=CC=C(CN1CCC(CC1)N(C(O)=O)C)C=C2 ZTKMACRGUPTAGN-UHFFFAOYSA-N 0.000 claims description 6
• 125000004849 alkoxymethyl group Chemical group 0.000 claims description 6
• 125000003282 alkyl amino group Chemical group 0.000 claims description 6
• 125000003368 amide group Chemical group 0.000 claims description 6
• 125000002837 carbocyclic group Chemical group 0.000 claims description 6
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 6
• 150000004677 hydrates Chemical class 0.000 claims description 6
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 6
• 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 6
• 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 6
• 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 6
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 6
• 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 6
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 6
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 10
• 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 9
• 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 5
• 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 5
• 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 5
• 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 5
• 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 5
• 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 5
• 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 5
• BPBIGNTWIBJUFE-UHFFFAOYSA-N 1-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 BPBIGNTWIBJUFE-UHFFFAOYSA-N 0.000 claims 5
• 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 5
• 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 5
• 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 5
• 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 5
• ZXWIMMQQXNYAHI-UHFFFAOYSA-N 1-[3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-ethylamino]propyl]pyrrolidin-2-one Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CN(CC)CCCN1CCCC1=O ZXWIMMQQXNYAHI-UHFFFAOYSA-N 0.000 claims 5
• PRZBQODDJBUJNO-UHFFFAOYSA-N 1-[3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-methylamino]propyl]pyrrolidin-2-one Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CN(C)CCCN1CCCC1=O PRZBQODDJBUJNO-UHFFFAOYSA-N 0.000 claims 5
• 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 5
• 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 5
• RVBPILVVAOIPAV-UHFFFAOYSA-N 1-[4-(1,3-benzothiazol-2-yloxy)phenyl]-n-methylmethanamine Chemical compound C1=CC(CNC)=CC=C1OC1=NC2=CC=CC=C2S1 RVBPILVVAOIPAV-UHFFFAOYSA-N 0.000 claims 5
• 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 5
• 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 5
• 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 5
• 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 5
• QNYYSADAZQJAEC-UHFFFAOYSA-N 1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazine-2-carboxylic acid Chemical compound OC(=O)C1CNCCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 QNYYSADAZQJAEC-UHFFFAOYSA-N 0.000 claims 5
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• 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 5
• BUZBVOKDNAZIIM-UHFFFAOYSA-N 1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidine-4-carboxylic acid Chemical group C1CC(C(=O)O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 BUZBVOKDNAZIIM-UHFFFAOYSA-N 0.000 claims 5
• JWKXNNWNYXKUNZ-UHFFFAOYSA-N 2-[2-[4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazin-1-yl]-2-oxoethyl]cyclopentan-1-one Chemical compound C1CN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)CC1CCCC1=O JWKXNNWNYXKUNZ-UHFFFAOYSA-N 0.000 claims 5
• 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 5
• HRGRBUXTSLZJHT-UHFFFAOYSA-N 2-[2-fluoro-4-(piperidin-1-ylmethyl)phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C(F)=CC=1CN1CCCCC1 HRGRBUXTSLZJHT-UHFFFAOYSA-N 0.000 claims 5
• 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 5
• PLMQGVLYXRYVOO-UHFFFAOYSA-N 2-[4-(piperidin-1-ylmethyl)phenoxy]-1h-benzimidazole Chemical group C=1C=C(OC=2NC3=CC=CC=C3N=2)C=CC=1CN1CCCCC1 PLMQGVLYXRYVOO-UHFFFAOYSA-N 0.000 claims 5
• LDQLMAQAGHYNDZ-UHFFFAOYSA-N 2-[4-[(3-methylpiperidin-1-yl)methyl]phenoxy]-1,3-benzothiazole Chemical compound C1C(C)CCCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 LDQLMAQAGHYNDZ-UHFFFAOYSA-N 0.000 claims 5
• AVRWIZZEDUWJDM-UHFFFAOYSA-N 2-[4-[(4,4-difluoropiperidin-1-yl)methyl]phenoxy]-1,3-benzothiazole Chemical compound C1CC(F)(F)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 AVRWIZZEDUWJDM-UHFFFAOYSA-N 0.000 claims 5
• 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 5
• 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 5
• 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 5
• 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 5
• 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 5
• 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 5
• BLYXDZLLGGDCOM-UHFFFAOYSA-N 2-amino-n-[[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]methyl]cyclobutane-1-carboxamide Chemical compound NC1CCC1C(=O)NCC1CCN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 BLYXDZLLGGDCOM-UHFFFAOYSA-N 0.000 claims 5
• 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 5
• 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 5
• WHQQJWGYHZAHDC-UHFFFAOYSA-N 3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-methylamino]propanenitrile Chemical compound C1=CC(CN(CCC#N)C)=CC=C1OC1=NC2=CC=CC=C2S1 WHQQJWGYHZAHDC-UHFFFAOYSA-N 0.000 claims 5
• 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 5
• QQNNAAFXXJNLGN-UHFFFAOYSA-N 4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]-n,n-dimethylpiperazine-1-sulfonamide Chemical compound C1CN(S(=O)(=O)N(C)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 QQNNAAFXXJNLGN-UHFFFAOYSA-N 0.000 claims 5
• 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 5
• VSIGIJUYXPEPFK-UHFFFAOYSA-N 4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazin-2-one Chemical compound C1CNC(=O)CN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 VSIGIJUYXPEPFK-UHFFFAOYSA-N 0.000 claims 5
• HTXWCJZXGZUXPD-UHFFFAOYSA-N 4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazine-1-carboxamide Chemical compound C1CN(C(=O)N)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 HTXWCJZXGZUXPD-UHFFFAOYSA-N 0.000 claims 5
• WPFDGFRNAYDUGG-UHFFFAOYSA-N 4-[[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-methylamino]methyl]phenol Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CN(C)CC1=CC=C(O)C=C1 WPFDGFRNAYDUGG-UHFFFAOYSA-N 0.000 claims 5
• 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 5
• XEWLYIXTOJAJNS-UHFFFAOYSA-N 4-methyl-2-[4-(piperidin-1-ylmethyl)phenoxy]-1,3-benzothiazole Chemical compound N=1C=2C(C)=CC=CC=2SC=1OC(C=C1)=CC=C1CN1CCCCC1 XEWLYIXTOJAJNS-UHFFFAOYSA-N 0.000 claims 5
• BVDOWGQUUMBGSZ-UHFFFAOYSA-N 6-chloro-2-[4-(piperidin-1-ylmethyl)phenoxy]-1,3-benzothiazole Chemical compound S1C2=CC(Cl)=CC=C2N=C1OC(C=C1)=CC=C1CN1CCCCC1 BVDOWGQUUMBGSZ-UHFFFAOYSA-N 0.000 claims 5
• MOOTXNIBLHHYFC-UHFFFAOYSA-N 6-methoxy-2-[4-(piperidin-1-ylmethyl)phenoxy]-1,3-benzothiazole Chemical compound S1C2=CC(OC)=CC=C2N=C1OC(C=C1)=CC=C1CN1CCCCC1 MOOTXNIBLHHYFC-UHFFFAOYSA-N 0.000 claims 5
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 5
• 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 5
• 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 5
• NOSINBBPECBLQO-UHFFFAOYSA-N [1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]thiourea Chemical compound C1CC(NC(=S)N)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 NOSINBBPECBLQO-UHFFFAOYSA-N 0.000 claims 5
• PQBKQQJREWSTTR-UHFFFAOYSA-N [1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]urea Chemical compound C1CC(NC(=O)N)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 PQBKQQJREWSTTR-UHFFFAOYSA-N 0.000 claims 5
• IOBMNXUVKZUXCN-UHFFFAOYSA-N [2-[3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-methylamino]propylamino]-2-oxoethyl] acetate Chemical compound C1=CC(CN(CCCNC(=O)COC(C)=O)C)=CC=C1OC1=NC2=CC=CC=C2S1 IOBMNXUVKZUXCN-UHFFFAOYSA-N 0.000 claims 5
• FWJJKSBJERLIKS-UHFFFAOYSA-N [2-[[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-methylamino]-2-oxoethyl] acetate Chemical compound C1CC(N(C)C(=O)COC(C)=O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 FWJJKSBJERLIKS-UHFFFAOYSA-N 0.000 claims 5
• GACNDIIZOZQWCU-UHFFFAOYSA-N [2-[[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]amino]-2-oxoethyl] acetate Chemical compound C1CC(NC(=O)COC(=O)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 GACNDIIZOZQWCU-UHFFFAOYSA-N 0.000 claims 5
• HFBKESRBVUOQOT-UHFFFAOYSA-N [4-(1,3-benzothiazol-2-yloxy)phenyl]methyl 4-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]butanoate Chemical compound C1=CC=C2SC(OC3=CC=C(C=C3)COC(CCCC3CCN(CC=4C=CC(OC=5SC6=CC=CC=C6N=5)=CC=4)CC3)=O)=NC2=C1 HFBKESRBVUOQOT-UHFFFAOYSA-N 0.000 claims 5
• JDVOEZLVRSILGD-UHFFFAOYSA-N [4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazin-1-yl]-(oxolan-2-yl)methanone Chemical compound C1CN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)C1CCCO1 JDVOEZLVRSILGD-UHFFFAOYSA-N 0.000 claims 5
• JTXYCSAJSQUDSP-UHFFFAOYSA-N [4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazin-1-yl]-thiophen-2-ylmethanone Chemical compound C1CN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)C1=CC=CS1 JTXYCSAJSQUDSP-UHFFFAOYSA-N 0.000 claims 5
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 5
• 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 5
• PONGENWTYBTRGD-UHFFFAOYSA-N ethyl n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OCC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 PONGENWTYBTRGD-UHFFFAOYSA-N 0.000 claims 5
• 125000001183 hydrocarbyl group Chemical group 0.000 claims 5
• MDHUVXHVMOQQAH-UHFFFAOYSA-N methyl 2-[[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-methylamino]-2-oxoacetate Chemical compound C1CC(N(C)C(=O)C(=O)OC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 MDHUVXHVMOQQAH-UHFFFAOYSA-N 0.000 claims 5
• UXSVVJASSRDVNH-UHFFFAOYSA-N methyl 2-[[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]amino]-2-oxoacetate Chemical compound C1CC(NC(=O)C(=O)OC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 UXSVVJASSRDVNH-UHFFFAOYSA-N 0.000 claims 5
• AYVVFQAFDYQHRG-UHFFFAOYSA-N methyl n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-n-methylcarbamate Chemical compound C1CC(N(C)C(=O)OC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 AYVVFQAFDYQHRG-UHFFFAOYSA-N 0.000 claims 5
• 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 5
• HCZICZIPHKCVQY-UHFFFAOYSA-N n'-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]-n'-methylpropane-1,3-diamine Chemical compound C1=CC(CN(CCCN)C)=CC=C1OC1=NC2=CC=CC=C2S1 HCZICZIPHKCVQY-UHFFFAOYSA-N 0.000 claims 5
• DONZDKOABWWBPP-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2SC(OC3=CC=C(C=C3)CN3CCC(CC3)NC=3SC4=CC=CC=C4N=3)=NC2=C1 DONZDKOABWWBPP-UHFFFAOYSA-N 0.000 claims 5
• QJYLKYIMEDEOAK-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-2,2,2-trifluoroacetamide Chemical compound C1CC(NC(=O)C(F)(F)F)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 QJYLKYIMEDEOAK-UHFFFAOYSA-N 0.000 claims 5
• ADDXOIYUEPCZQF-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-2-hydroxy-n-methylacetamide Chemical compound C1CC(N(C)C(=O)CO)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 ADDXOIYUEPCZQF-UHFFFAOYSA-N 0.000 claims 5
• IJHSPFFWIXGDBB-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-2-hydroxyacetamide Chemical compound C1CC(NC(=O)CO)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 IJHSPFFWIXGDBB-UHFFFAOYSA-N 0.000 claims 5
• VPANENIDMTVNAC-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-2-methylpropanamide Chemical compound C1CC(NC(=O)C(C)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 VPANENIDMTVNAC-UHFFFAOYSA-N 0.000 claims 5
• HFEYBJBRPWBKPE-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-n-methylacetamide Chemical compound C1CC(N(C)C(C)=O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 HFEYBJBRPWBKPE-UHFFFAOYSA-N 0.000 claims 5
• 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 5
• UVZMEOGKJYOCNE-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]acetamide Chemical compound C1CC(NC(=O)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 UVZMEOGKJYOCNE-UHFFFAOYSA-N 0.000 claims 5
• DWGRXFZEVJEZNM-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]benzenesulfonamide Chemical compound C1CN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1NS(=O)(=O)C1=CC=CC=C1 DWGRXFZEVJEZNM-UHFFFAOYSA-N 0.000 claims 5
• VQXIIECMEAFXHB-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]butanamide Chemical compound C1CC(NC(=O)CCC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 VQXIIECMEAFXHB-UHFFFAOYSA-N 0.000 claims 5
• IBYLIDCQLOQAKP-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]ethanesulfonamide Chemical compound C1CC(NS(=O)(=O)CC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 IBYLIDCQLOQAKP-UHFFFAOYSA-N 0.000 claims 5
• BYVGFOJKHKICLQ-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]formamide Chemical compound C1CC(NC=O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 BYVGFOJKHKICLQ-UHFFFAOYSA-N 0.000 claims 5
• 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 5
• WSCRCQJBQBSKIR-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]oxolane-2-carboxamide Chemical compound C1CN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1NC(=O)C1CCCO1 WSCRCQJBQBSKIR-UHFFFAOYSA-N 0.000 claims 5
• VJKCOKFFSRWBHL-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]propanamide Chemical compound C1CC(NC(=O)CC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 VJKCOKFFSRWBHL-UHFFFAOYSA-N 0.000 claims 5
• YTSLVJQQFDKVOS-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]propane-1-sulfonamide Chemical compound C1CC(NS(=O)(=O)CCC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 YTSLVJQQFDKVOS-UHFFFAOYSA-N 0.000 claims 5
• HZQBZGVRVIJLBC-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]propane-2-sulfonamide Chemical compound C1CC(NS(=O)(=O)C(C)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 HZQBZGVRVIJLBC-UHFFFAOYSA-N 0.000 claims 5
• HFGAHSCBTPFFFS-UHFFFAOYSA-N n-[3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-cyclopropylamino]propyl]-2-methylpropanamide Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CN(CCCNC(=O)C(C)C)C1CC1 HFGAHSCBTPFFFS-UHFFFAOYSA-N 0.000 claims 5
• MMCCESFFGDOREM-UHFFFAOYSA-N n-[3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-cyclopropylamino]propyl]oxolane-2-carboxamide Chemical compound C1CCOC1C(=O)NCCCN(CC=1C=CC(OC=2SC3=CC=CC=C3N=2)=CC=1)C1CC1 MMCCESFFGDOREM-UHFFFAOYSA-N 0.000 claims 5
• DPAOPNCXDCUBQX-UHFFFAOYSA-N n-[3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-methylamino]propyl]-2-hydroxyacetamide Chemical compound C1=CC(CN(CCCNC(=O)CO)C)=CC=C1OC1=NC2=CC=CC=C2S1 DPAOPNCXDCUBQX-UHFFFAOYSA-N 0.000 claims 5
• BXRXDVJEZLZJTB-UHFFFAOYSA-N n-[3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-methylamino]propyl]methanesulfonamide Chemical compound C1=CC(CN(CCCNS(C)(=O)=O)C)=CC=C1OC1=NC2=CC=CC=C2S1 BXRXDVJEZLZJTB-UHFFFAOYSA-N 0.000 claims 5
• 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 5
• 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 5
• STZJUCAEGPABRA-UHFFFAOYSA-N n-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]-n,1-dimethylpiperidin-4-amine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CN(C)C1CCN(C)CC1 STZJUCAEGPABRA-UHFFFAOYSA-N 0.000 claims 5
• 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 5
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