JP2007500706A5

JP2007500706A5 -

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Publication number: JP2007500706A5
Authority: JP; Japan
Prior art keywords: alkyl; ethyl; group; yloxy; phenyl
Prior art date: 2004-07-27
Legal status : Granted

Application number

JP2006522022A

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English (en)

Japanese (ja)

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JP2007500706A (ja

JP4726238B2 (ja

Filing date

2004-07-27

Publication date

2007-09-20

2004-07-27 Application filed filed Critical

2004-07-27 Priority claimed from PCT/US2004/024309 external-priority patent/WO2005012297A1/en

2007-01-18 Publication of JP2007500706A publication Critical patent/JP2007500706A/ja

2007-09-20 Publication of JP2007500706A5 publication Critical patent/JP2007500706A5/ja

2011-07-20 Application granted granted Critical

2011-07-20 Publication of JP4726238B2 publication Critical patent/JP4726238B2/ja

2024-07-27 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

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125000000217 alkyl group Chemical group 0.000 claims description 736
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 375
-1 4-ethyl-phenoxy Chemical group 0.000 claims description 346
229910052757 nitrogen Inorganic materials 0.000 claims description 241
229910052799 carbon Inorganic materials 0.000 claims description 237
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 206
125000005842 heteroatom Chemical group 0.000 claims description 194
125000001424 substituent group Chemical group 0.000 claims description 136
125000000623 heterocyclic group Chemical group 0.000 claims description 101
229910052760 oxygen Inorganic materials 0.000 claims description 91
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 87
150000001875 compounds Chemical class 0.000 claims description 81
229910052717 sulfur Inorganic materials 0.000 claims description 71
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
229910052739 hydrogen Inorganic materials 0.000 claims description 54
125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 49
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 47
101000619898 Homo sapiens Leukotriene A-4 hydrolase Proteins 0.000 claims description 37
102100022118 Leukotriene A-4 hydrolase Human genes 0.000 claims description 35
239000008194 pharmaceutical composition Substances 0.000 claims description 32
125000003342 alkenyl group Chemical group 0.000 claims description 31
125000001072 heteroaryl group Chemical group 0.000 claims description 31
125000005037 alkyl phenyl group Chemical group 0.000 claims description 30
125000000304 alkynyl group Chemical group 0.000 claims description 28
125000005843 halogen group Chemical group 0.000 claims description 22
229920006395 saturated elastomer Polymers 0.000 claims description 20
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 20
150000001408 amides Chemical class 0.000 claims description 17
150000002148 esters Chemical class 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 17
239000012453 solvate Substances 0.000 claims description 17
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 13
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 12
125000003368 amide group Chemical group 0.000 claims description 12
125000000392 cycloalkenyl group Chemical group 0.000 claims description 12
125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 10
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
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 10
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 10
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 10
150000001721 carbon Chemical group 0.000 claims description 10
125000001153 fluoro group Chemical group F* 0.000 claims description 10
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 10
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 10
125000003373 pyrazinyl group Chemical group 0.000 claims description 10
125000004076 pyridyl group Chemical group 0.000 claims description 10
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
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 9
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 9
125000005605 benzo group Chemical group 0.000 claims description 9
230000001404 mediated effect Effects 0.000 claims description 8
125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 8
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 6
125000004849 alkoxymethyl group Chemical group 0.000 claims description 5
150000004677 hydrates Chemical class 0.000 claims description 5
XJLDYKIEURAVBW-UHFFFAOYSA-N 3-decanone Chemical compound CCCCCCCC(=O)CC XJLDYKIEURAVBW-UHFFFAOYSA-N 0.000 claims description 2
125000003341 7 membered heterocyclic group Chemical group 0.000 claims 6
101150008896 hetR gene Proteins 0.000 claims 6
125000004122 cyclic group Chemical group 0.000 claims 4
125000001183 hydrocarbyl group Chemical group 0.000 claims 4
125000000714 pyrimidinyl group Chemical group 0.000 claims 4
238000006467 substitution reaction Methods 0.000 claims 3
239000004480 active ingredient Substances 0.000 claims 1
150000001556 benzimidazoles Chemical class 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
238000000034 method Methods 0.000 description 144
125000000753 cycloalkyl group Chemical group 0.000 description 13
QFDISQIDKZUABE-UHFFFAOYSA-N 1,1'-bipiperidine Chemical compound C1CCCCN1N1CCCCC1 QFDISQIDKZUABE-UHFFFAOYSA-N 0.000 description 10
FDSUAPKEGWZEFY-UHFFFAOYSA-N ethyl 2-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]tetrazol-5-yl]acetate Chemical compound CCOC(=O)CC1=NN=NN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 FDSUAPKEGWZEFY-UHFFFAOYSA-N 0.000 description 10
NJXASJKPUOBSSP-UHFFFAOYSA-N ethyl 4-[(1-acetylpiperidin-4-yl)-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]amino]butanoate Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCC(=O)OCC)C1CCN(C(C)=O)CC1 NJXASJKPUOBSSP-UHFFFAOYSA-N 0.000 description 10
201000001320 Atherosclerosis Diseases 0.000 description 9
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 9
206010061218 Inflammation Diseases 0.000 description 9
208000022559 Inflammatory bowel disease Diseases 0.000 description 9
208000006673 asthma Diseases 0.000 description 9
230000004054 inflammatory process Effects 0.000 description 9
201000006417 multiple sclerosis Diseases 0.000 description 9
206010039073 rheumatoid arthritis Diseases 0.000 description 9
201000004681 Psoriasis Diseases 0.000 description 8
0 CNC(N*)=NC#N Chemical compound CNC(N*)=NC#N 0.000 description 7
150000002430 hydrocarbons Chemical group 0.000 description 6
NZKQQHXHRTXECS-IEBWSBKVSA-N (1r,2r)-2-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethylamino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NCCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 NZKQQHXHRTXECS-IEBWSBKVSA-N 0.000 description 5
YNIMHCVHLVQJOW-QZTJIDSGSA-N (1r,2r)-2-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethylamino]cyclohexane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCC[C@H]1NCCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 YNIMHCVHLVQJOW-QZTJIDSGSA-N 0.000 description 5
NZKQQHXHRTXECS-MJGOQNOKSA-N (1s,2r)-2-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethylamino]cyclohexan-1-ol Chemical compound O[C@H]1CCCC[C@H]1NCCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 NZKQQHXHRTXECS-MJGOQNOKSA-N 0.000 description 5
YNIMHCVHLVQJOW-ZWKOTPCHSA-N (1s,2r)-2-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethylamino]cyclohexane-1-carboxylic acid Chemical compound OC(=O)[C@H]1CCCC[C@H]1NCCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 YNIMHCVHLVQJOW-ZWKOTPCHSA-N 0.000 description 5
JWCULZKVIZMYMV-MRXNPFEDSA-N (2r)-3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]-2-methylpropan-1-ol Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(C[C@H](CO)C)C1CC1 JWCULZKVIZMYMV-MRXNPFEDSA-N 0.000 description 5
JWCULZKVIZMYMV-INIZCTEOSA-N (2s)-3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]-2-methylpropan-1-ol Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(C[C@@H](CO)C)C1CC1 JWCULZKVIZMYMV-INIZCTEOSA-N 0.000 description 5
HTPHRBUADWIZAP-MRXNPFEDSA-N (3r)-1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 HTPHRBUADWIZAP-MRXNPFEDSA-N 0.000 description 5
HXCZXAJCNGESAD-OAHLLOKOSA-N (3r)-1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]pyrrolidin-3-ol Chemical compound C1[C@H](O)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 HXCZXAJCNGESAD-OAHLLOKOSA-N 0.000 description 5
ALUPMMYRKWGOJR-GOSISDBHSA-N (4r)-1-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]-4-hydroxypyrrolidin-2-one Chemical compound O=C1C[C@@H](O)CN1C1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 ALUPMMYRKWGOJR-GOSISDBHSA-N 0.000 description 5
KUWGLWGPMUFUFF-LJQANCHMSA-N (4r)-1-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-4-hydroxypyrrolidin-2-one Chemical compound O=C1C[C@@H](O)CN1C1CCN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 KUWGLWGPMUFUFF-LJQANCHMSA-N 0.000 description 5
ALUPMMYRKWGOJR-SFHVURJKSA-N (4s)-1-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]-4-hydroxypyrrolidin-2-one Chemical compound O=C1C[C@H](O)CN1C1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 ALUPMMYRKWGOJR-SFHVURJKSA-N 0.000 description 5
KUWGLWGPMUFUFF-IBGZPJMESA-N (4s)-1-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-4-hydroxypyrrolidin-2-one Chemical compound O=C1C[C@H](O)CN1C1CCN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 KUWGLWGPMUFUFF-IBGZPJMESA-N 0.000 description 5
WZHDVKIJJSEYHG-UHFFFAOYSA-N 1-[1-[2-[4-(1,3-benzothiazol-2-ylmethyl)phenoxy]ethyl]piperidin-4-yl]pyrrolidin-2-one Chemical compound O=C1CCCN1C1CCN(CCOC=2C=CC(CC=3SC4=CC=CC=C4N=3)=CC=2)CC1 WZHDVKIJJSEYHG-UHFFFAOYSA-N 0.000 description 5
HOYVUZXQBKNTGW-UHFFFAOYSA-N 1-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]-5-oxopyrrolidine-2-carboxylic acid Chemical compound OC(=O)C1CCC(=O)N1C1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 HOYVUZXQBKNTGW-UHFFFAOYSA-N 0.000 description 5
OAUXHFPOFOZZLZ-UHFFFAOYSA-N 1-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]pyrrolidin-2-one Chemical compound O=C1CCCN1C1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 OAUXHFPOFOZZLZ-UHFFFAOYSA-N 0.000 description 5
HPXKQSLWBBWWNU-UHFFFAOYSA-N 1-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]pyrrolidine-2-thione Chemical compound S=C1CCCN1C1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 HPXKQSLWBBWWNU-UHFFFAOYSA-N 0.000 description 5
HYZDBMWCJUYKAU-UHFFFAOYSA-N 1-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-3-cyano-2-methylguanidine Chemical compound C1CC(NC(NC#N)=NC)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 HYZDBMWCJUYKAU-UHFFFAOYSA-N 0.000 description 5
YALDRDNOXRAUNF-UHFFFAOYSA-N 1-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-3-methylbenzimidazol-2-one Chemical compound C1=CC=C2SC(OC3=CC=C(C=C3)CCN3CCC(CC3)N3C4=CC=CC=C4N(C3=O)C)=NC2=C1 YALDRDNOXRAUNF-UHFFFAOYSA-N 0.000 description 5
GVNNEHBYBWFJRK-UHFFFAOYSA-N 1-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-3h-indol-2-one Chemical compound C1=CC=C2SC(OC3=CC=C(C=C3)CCN3CCC(CC3)N3C4=CC=CC=C4CC3=O)=NC2=C1 GVNNEHBYBWFJRK-UHFFFAOYSA-N 0.000 description 5
GIYCUMSDCASBAI-UHFFFAOYSA-N 1-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]pyrrolidin-2-one Chemical compound O=C1CCCN1C1CCN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 GIYCUMSDCASBAI-UHFFFAOYSA-N 0.000 description 5
MTCQVADOSPRCJN-UHFFFAOYSA-N 1-[1-[2-[4-(1h-benzimidazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]pyrrolidin-2-one Chemical compound O=C1CCCN1C1CCN(CCOC=2C=CC(OC=3NC4=CC=CC=C4N=3)=CC=2)CC1 MTCQVADOSPRCJN-UHFFFAOYSA-N 0.000 description 5
XFRIKBHRWNGBEX-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-ylmethyl)phenoxy]ethyl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1CCOC(C=C1)=CC=C1CC1=NC2=CC=CC=C2S1 XFRIKBHRWNGBEX-UHFFFAOYSA-N 0.000 description 5
AREHXWXMLHRGGI-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]-4-(4-bromophenyl)piperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=C(Br)C=C1 AREHXWXMLHRGGI-UHFFFAOYSA-N 0.000 description 5
FQIDMNGIAGRBQM-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]-4-(4-chlorophenyl)piperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=C(Cl)C=C1 FQIDMNGIAGRBQM-UHFFFAOYSA-N 0.000 description 5
JAAJPVQIKRVPLX-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]-4-[4-chloro-3-(trifluoromethyl)phenyl]piperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=C(Cl)C(C(F)(F)F)=C1 JAAJPVQIKRVPLX-UHFFFAOYSA-N 0.000 description 5
XHHKCYXHMVGTHH-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]-4-benzylpiperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1(O)CC1=CC=CC=C1 XHHKCYXHMVGTHH-UHFFFAOYSA-N 0.000 description 5
SUNOKJAPKRXALX-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]-4-phenylpiperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=CC=C1 SUNOKJAPKRXALX-UHFFFAOYSA-N 0.000 description 5
KWCUTOWTFFAFGD-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]-n-propan-2-ylsulfonylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NS(=O)(=O)C(C)C)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 KWCUTOWTFFAFGD-UHFFFAOYSA-N 0.000 description 5
RYVZYGCBFLGXIF-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-amine Chemical compound C1CC(N)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 RYVZYGCBFLGXIF-UHFFFAOYSA-N 0.000 description 5
QEEKSUQXDWTJIW-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 QEEKSUQXDWTJIW-UHFFFAOYSA-N 0.000 description 5
CJHALXUVAOMHMH-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 CJHALXUVAOMHMH-UHFFFAOYSA-N 0.000 description 5
YMOXSVLBXXDKHI-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 YMOXSVLBXXDKHI-UHFFFAOYSA-N 0.000 description 5
QDHFWEBOSZNXQV-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]propan-2-ol Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CC(O)C)C1CC1 QDHFWEBOSZNXQV-UHFFFAOYSA-N 0.000 description 5
FDTVVMYDEDPLPY-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-4-phenylpiperidin-4-ol Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=CC=C1 FDTVVMYDEDPLPY-UHFFFAOYSA-N 0.000 description 5
YHLADMHTBUNYOB-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-n-(1-hydroxy-2-methylpropan-2-yl)piperidine-4-carboxamide Chemical compound C1CC(C(=O)NC(C)(CO)C)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 YHLADMHTBUNYOB-UHFFFAOYSA-N 0.000 description 5
CJJVRDNLUIRCAI-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-n-(2-cyanoethyl)piperidine-4-carboxamide Chemical compound C1CC(C(NCCC#N)=O)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 CJJVRDNLUIRCAI-UHFFFAOYSA-N 0.000 description 5
FMUDYLUABJPBPU-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-n-hydroxypiperidine-4-carboxamide Chemical compound C1CC(C(=O)NO)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 FMUDYLUABJPBPU-UHFFFAOYSA-N 0.000 description 5
QYZCEWWRMPEVEO-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-n-phenylmethoxypiperidine-4-carboxamide Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1C(=O)NOCC1=CC=CC=C1 QYZCEWWRMPEVEO-UHFFFAOYSA-N 0.000 description 5
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KXVAJEVPYPGMPK-UHFFFAOYSA-N 4-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]morpholin-3-one Chemical compound O=C1COCCN1C1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 KXVAJEVPYPGMPK-UHFFFAOYSA-N 0.000 description 5
WCIUKVZFMKMBCW-UHFFFAOYSA-N 4-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]butanoic acid Chemical compound C1CC(CCCC(=O)O)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 WCIUKVZFMKMBCW-UHFFFAOYSA-N 0.000 description 5
WVRPNEFAKCUFKR-UHFFFAOYSA-N 4-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]morpholin-3-one Chemical compound O=C1COCCN1C1CCN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 WVRPNEFAKCUFKR-UHFFFAOYSA-N 0.000 description 5
ZKVKOYHSMDDWLY-UHFFFAOYSA-N 4-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidine-4-carbonyl]piperazine-1-carboxylic acid Chemical compound C1CN(C(=O)O)CCN1C(=O)C1CCN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 ZKVKOYHSMDDWLY-UHFFFAOYSA-N 0.000 description 5
PSIRNSCDVFAVIN-UHFFFAOYSA-N 4-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl-cyclopropylamino]butanoic acid Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCN(CCCC(=O)O)C1CC1 PSIRNSCDVFAVIN-UHFFFAOYSA-N 0.000 description 5
XHNDRMFJEUDOIJ-UHFFFAOYSA-N 4-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]morpholine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCN1CCOCC1 XHNDRMFJEUDOIJ-UHFFFAOYSA-N 0.000 description 5
AORYDRPTXXODDN-UHFFFAOYSA-N 4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-(cyclopropylmethyl)amino]butanenitrile Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCC#N)CC1CC1 AORYDRPTXXODDN-UHFFFAOYSA-N 0.000 description 5
AWRZNORPMQXIRX-UHFFFAOYSA-N 4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-(cyclopropylmethyl)amino]butanoic acid Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCC(=O)O)CC1CC1 AWRZNORPMQXIRX-UHFFFAOYSA-N 0.000 description 5
IIGZDSMTHIELMM-UHFFFAOYSA-N 4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]butanenitrile Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCC#N)C1CC1 IIGZDSMTHIELMM-UHFFFAOYSA-N 0.000 description 5
SBIHJWUTAGVKMS-UHFFFAOYSA-N 4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]butanoic acid Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCC(=O)O)C1CC1 SBIHJWUTAGVKMS-UHFFFAOYSA-N 0.000 description 5
FPKGILRFIBMTJZ-UHFFFAOYSA-N 4-[2-[4-(1h-benzimidazol-2-yloxy)phenoxy]ethyl]morpholine Chemical compound C=1C=C(OC=2NC3=CC=CC=C3N=2)C=CC=1OCCN1CCOCC1 FPKGILRFIBMTJZ-UHFFFAOYSA-N 0.000 description 5
JNPNVLKDSZMXFQ-UHFFFAOYSA-N 4-[2-[4-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperazin-1-yl]ethyl]morpholine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCN(CC1)CCN1CCN1CCOCC1 JNPNVLKDSZMXFQ-UHFFFAOYSA-N 0.000 description 5
IKCVCAQFEIOACD-UHFFFAOYSA-N 4-[2-[4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]ethyl]morpholine Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1CCN1CCOCC1 IKCVCAQFEIOACD-UHFFFAOYSA-N 0.000 description 5
CBDDJDKBBAWXOF-UHFFFAOYSA-N 4-[4-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperazin-1-yl]phenol Chemical compound C1=CC(O)=CC=C1N1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 CBDDJDKBBAWXOF-UHFFFAOYSA-N 0.000 description 5
LBHWCFLNWBTJEG-UHFFFAOYSA-N 4-[4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazine-1-carbonyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)N1CCN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 LBHWCFLNWBTJEG-UHFFFAOYSA-N 0.000 description 5
CSCWWOYURRGLGO-UHFFFAOYSA-N 5-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]pentanoic acid Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCCC(=O)O)C1CC1 CSCWWOYURRGLGO-UHFFFAOYSA-N 0.000 description 5
JTYSPUQIDLBFOM-UHFFFAOYSA-N 6-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]hexanoic acid Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCCCC(=O)O)C1CC1 JTYSPUQIDLBFOM-UHFFFAOYSA-N 0.000 description 5
GCTFSJWCHIHSRE-UHFFFAOYSA-N 7-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]heptanoic acid Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCCCCC(=O)O)C1CC1 GCTFSJWCHIHSRE-UHFFFAOYSA-N 0.000 description 5
ZKBRIYLQMSDIBH-UHFFFAOYSA-N 8-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound O=C1NCCC11CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 ZKBRIYLQMSDIBH-UHFFFAOYSA-N 0.000 description 5
YNNQIONTMFJUJV-UHFFFAOYSA-N 8-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]octanoic acid Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCCCCCC(=O)O)C1CC1 YNNQIONTMFJUJV-UHFFFAOYSA-N 0.000 description 5
LHSXKZYJSBXKAB-UHFFFAOYSA-N 8-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound N1C(=O)NC(=O)C11CCN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 LHSXKZYJSBXKAB-UHFFFAOYSA-N 0.000 description 5
BQCXGLQSYZZFMV-UHFFFAOYSA-N 8-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC11C(=O)NCN1C1=CC=CC=C1 BQCXGLQSYZZFMV-UHFFFAOYSA-N 0.000 description 5
ZCAWZNVFLHPUNA-UHFFFAOYSA-N 8-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound O=C1NCCC11CCN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 ZCAWZNVFLHPUNA-UHFFFAOYSA-N 0.000 description 5
BCDAOWRIXZABCA-UHFFFAOYSA-N [1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-2-yl]methanol Chemical compound OCC1CCCCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 BCDAOWRIXZABCA-UHFFFAOYSA-N 0.000 description 5
LOQINUJPBZYKTB-UHFFFAOYSA-N [1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]-[4-(2-hydroxyethyl)piperazin-1-yl]methanone Chemical compound C1CN(CCO)CCN1C(=O)C1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 LOQINUJPBZYKTB-UHFFFAOYSA-N 0.000 description 5
PWCMDMVETUPJHG-UHFFFAOYSA-N [1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]-[4-(2-hydroxyethyl)piperidin-1-yl]methanone Chemical compound C1CC(CCO)CCN1C(=O)C1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 PWCMDMVETUPJHG-UHFFFAOYSA-N 0.000 description 5
SKVBWYUPTRWTGW-UHFFFAOYSA-N [1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]-[4-(hydroxymethyl)piperidin-1-yl]methanone Chemical compound C1CC(CO)CCN1C(=O)C1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 SKVBWYUPTRWTGW-UHFFFAOYSA-N 0.000 description 5
RJMLMGFIAISZQE-UHFFFAOYSA-N [1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]-pyrrolidin-1-ylmethanone Chemical compound C1CN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1C(=O)N1CCCC1 RJMLMGFIAISZQE-UHFFFAOYSA-N 0.000 description 5
NTOXQUBAGYBHEG-UHFFFAOYSA-N [1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]methanol Chemical compound C1CC(CO)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 NTOXQUBAGYBHEG-UHFFFAOYSA-N 0.000 description 5
AQNLLERPRHRRKM-UHFFFAOYSA-N [1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-3-yl]methanol Chemical compound C1C(CO)CCCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 AQNLLERPRHRRKM-UHFFFAOYSA-N 0.000 description 5
DUOJBDYMEDTCDU-UHFFFAOYSA-N [1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1CCN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 DUOJBDYMEDTCDU-UHFFFAOYSA-N 0.000 description 5
GFBHSUHBGXWTMP-UHFFFAOYSA-N [1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]urea Chemical compound C1CC(NC(=O)N)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 GFBHSUHBGXWTMP-UHFFFAOYSA-N 0.000 description 5
PTPDJDATJRANLS-UHFFFAOYSA-N [1-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]piperidin-2-yl]methanol Chemical compound OCC1CCCCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2O1 PTPDJDATJRANLS-UHFFFAOYSA-N 0.000 description 5
TYUINOFAKUGLOA-UHFFFAOYSA-N [1-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]piperidin-3-yl]methanol Chemical compound C1C(CO)CCCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2O1 TYUINOFAKUGLOA-UHFFFAOYSA-N 0.000 description 5
MVWHGHDOPRCATH-UHFFFAOYSA-N [1-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]methanol Chemical compound C1CC(CO)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2O1 MVWHGHDOPRCATH-UHFFFAOYSA-N 0.000 description 5
MVOUDSMIRONHKB-UHFFFAOYSA-N [1-[2-[4-(1h-benzimidazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]methanol Chemical compound C1CC(CO)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2N1 MVOUDSMIRONHKB-UHFFFAOYSA-N 0.000 description 5
MZSBBGNOOWKWET-UHFFFAOYSA-N [2-[[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-methylamino]-2-oxoethyl] acetate Chemical compound C1CC(N(C)C(=O)COC(C)=O)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 MZSBBGNOOWKWET-UHFFFAOYSA-N 0.000 description 5
IVKUGUCBCYQYLC-UHFFFAOYSA-N [4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]-(5-methylpyrazin-2-yl)methanone Chemical compound C1=NC(C)=CN=C1C(=O)N1CCN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 IVKUGUCBCYQYLC-UHFFFAOYSA-N 0.000 description 5
RHNNPEULEGUXQI-UHFFFAOYSA-N [4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]-(oxolan-2-yl)methanone Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)C1CCCO1 RHNNPEULEGUXQI-UHFFFAOYSA-N 0.000 description 5
KVUYDYZEJDFNHJ-UHFFFAOYSA-N [4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]-(oxolan-3-yl)methanone Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)C1CCOC1 KVUYDYZEJDFNHJ-UHFFFAOYSA-N 0.000 description 5
RHNNPEULEGUXQI-OAQYLSRUSA-N [4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]-[(2r)-oxolan-2-yl]methanone Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)[C@H]1CCCO1 RHNNPEULEGUXQI-OAQYLSRUSA-N 0.000 description 5
RHNNPEULEGUXQI-NRFANRHFSA-N [4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]-[(2s)-oxolan-2-yl]methanone Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)[C@@H]1CCCO1 RHNNPEULEGUXQI-NRFANRHFSA-N 0.000 description 5
HFVJQHOAAGUSCE-UHFFFAOYSA-N [4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]-cyclopropylmethanone Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)C1CC1 HFVJQHOAAGUSCE-UHFFFAOYSA-N 0.000 description 5
SRXPOGKYEYCPMQ-UHFFFAOYSA-N [4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]-morpholin-4-ylmethanone Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)N1CCOCC1 SRXPOGKYEYCPMQ-UHFFFAOYSA-N 0.000 description 5
JTHRNERQCUBCFR-UHFFFAOYSA-N [4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]-pyridin-3-ylmethanone Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)C1=CC=CN=C1 JTHRNERQCUBCFR-UHFFFAOYSA-N 0.000 description 5
UHNQARHEORQPIK-UHFFFAOYSA-N [4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]-pyridin-4-ylmethanone Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)C1=CC=NC=C1 UHNQARHEORQPIK-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
BIZVFRGJJTYCDX-UHFFFAOYSA-N ethyl 1-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]-5-oxopyrrolidine-2-carboxylate Chemical compound CCOC(=O)C1CCC(=O)N1C1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 BIZVFRGJJTYCDX-UHFFFAOYSA-N 0.000 description 5
BMZRZMPVKLUBNR-UHFFFAOYSA-N ethyl 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 BMZRZMPVKLUBNR-UHFFFAOYSA-N 0.000 description 5
OWUKUHRUWJWPLR-UHFFFAOYSA-N ethyl 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-4-phenylpiperidine-4-carboxylate Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1(C(=O)OCC)C1=CC=CC=C1 OWUKUHRUWJWPLR-UHFFFAOYSA-N 0.000 description 5
YFKRUZPIKGRERG-UHFFFAOYSA-N ethyl 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 YFKRUZPIKGRERG-UHFFFAOYSA-N 0.000 description 5
RXQCBZKSQRTWHU-UHFFFAOYSA-N ethyl 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 RXQCBZKSQRTWHU-UHFFFAOYSA-N 0.000 description 5
OZXVXVTYNDRZCK-UHFFFAOYSA-N ethyl 1-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]piperidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2O1 OZXVXVTYNDRZCK-UHFFFAOYSA-N 0.000 description 5
MMMXMWIHIHNYFE-UHFFFAOYSA-N ethyl 1-[2-[4-(1h-benzimidazol-2-yloxy)phenoxy]ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2N1 MMMXMWIHIHNYFE-UHFFFAOYSA-N 0.000 description 5
YPBOSXISLJYDLJ-UHFFFAOYSA-N ethyl 1-[3-[4-(1,3-benzothiazol-2-yloxy)phenyl]propyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CCCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 YPBOSXISLJYDLJ-UHFFFAOYSA-N 0.000 description 5
HXOYCVQFHUMTJT-UHFFFAOYSA-N ethyl 2-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]acetate Chemical compound C1CC(CC(=O)OCC)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 HXOYCVQFHUMTJT-UHFFFAOYSA-N 0.000 description 5
ZOBOTHHIAYPQOL-UHFFFAOYSA-N ethyl 2-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]acetate Chemical compound C1CC(CC(=O)OCC)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 ZOBOTHHIAYPQOL-UHFFFAOYSA-N 0.000 description 5
VVUYEMHYAGYMQG-UHFFFAOYSA-N ethyl 2-[[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidine-4-carbonyl]-methylamino]acetate Chemical compound C1CC(C(=O)N(C)CC(=O)OCC)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 VVUYEMHYAGYMQG-UHFFFAOYSA-N 0.000 description 5
XWFRBROQZURNHK-UHFFFAOYSA-N ethyl 2-[[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]methyl]cyclopropane-1-carboxylate Chemical compound CCOC(=O)C1CC1CN(C1CC1)CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 XWFRBROQZURNHK-UHFFFAOYSA-N 0.000 description 5
FWLUNXGSLLZGCE-UHFFFAOYSA-N ethyl 3-[[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidine-4-carbonyl]amino]propanoate Chemical compound C1CC(C(=O)NCCC(=O)OCC)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 FWLUNXGSLLZGCE-UHFFFAOYSA-N 0.000 description 5
MMEFFRGZDFLOAC-UHFFFAOYSA-N ethyl 4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-(cyclopropylmethyl)amino]butanoate Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCC(=O)OCC)CC1CC1 MMEFFRGZDFLOAC-UHFFFAOYSA-N 0.000 description 5
JGAPREBEXBBQFV-UHFFFAOYSA-N ethyl 4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethylamino]butanoate Chemical compound C1=CC(CCNCCCC(=O)OCC)=CC=C1OC1=NC2=CC=CC=C2S1 JGAPREBEXBBQFV-UHFFFAOYSA-N 0.000 description 5
KUZXJGBTRMWOEO-UHFFFAOYSA-N ethyl 4-[4-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperazine-1-carbonyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C(=O)N1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 KUZXJGBTRMWOEO-UHFFFAOYSA-N 0.000 description 5
CPRMTRQPCBTSCA-UHFFFAOYSA-N ethyl 6-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]hexanoate Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCCCC(=O)OCC)C1CC1 CPRMTRQPCBTSCA-UHFFFAOYSA-N 0.000 description 5
GGVBHBACWISUCI-UHFFFAOYSA-N ethyl 7-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]heptanoate Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCCCCC(=O)OCC)C1CC1 GGVBHBACWISUCI-UHFFFAOYSA-N 0.000 description 5
XTGUVGAFFDTRHE-UHFFFAOYSA-N ethyl 8-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]octanoate Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCCCCCC(=O)OCC)C1CC1 XTGUVGAFFDTRHE-UHFFFAOYSA-N 0.000 description 5
CMLMEBPFTNCLDG-UHFFFAOYSA-N methyl 1-[2-[4-(1,3-benzothiazol-2-ylmethyl)phenoxy]ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OC)CCN1CCOC(C=C1)=CC=C1CC1=NC2=CC=CC=C2S1 CMLMEBPFTNCLDG-UHFFFAOYSA-N 0.000 description 5
GWSZYUJFYKFDPN-UHFFFAOYSA-N methyl 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OC)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 GWSZYUJFYKFDPN-UHFFFAOYSA-N 0.000 description 5
YDSNEVLFPYRGGL-UHFFFAOYSA-N methyl 1-[2-[4-(1,3-benzoxazol-2-yloxy)phenyl]ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OC)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2O1 YDSNEVLFPYRGGL-UHFFFAOYSA-N 0.000 description 5
FYJLYIYGBKVEGO-UHFFFAOYSA-N methyl 1-[2-[4-(1h-benzimidazol-2-yloxy)phenyl]ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OC)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2N1 FYJLYIYGBKVEGO-UHFFFAOYSA-N 0.000 description 5
JHAVVDDIZYSOCI-UHFFFAOYSA-N methyl 2-[4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]-2-oxoacetate Chemical compound C1CN(C(=O)C(=O)OC)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 JHAVVDDIZYSOCI-UHFFFAOYSA-N 0.000 description 5
HNCFYDRWWPOACC-UHFFFAOYSA-N methyl 5-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]pentanoate Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCCC(=O)OC)C1CC1 HNCFYDRWWPOACC-UHFFFAOYSA-N 0.000 description 5
JHTONAOHIXKHMD-UHFFFAOYSA-N methyl n'-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-n-cyanocarbamimidothioate Chemical compound C1CC(NC(SC)=NC#N)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 JHTONAOHIXKHMD-UHFFFAOYSA-N 0.000 description 5
XJNRXSAAVCVMPH-UHFFFAOYSA-N n-(benzenesulfonyl)-1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidine-4-carboxamide;trifluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)F.C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1C(=O)NS(=O)(=O)C1=CC=CC=C1 XJNRXSAAVCVMPH-UHFFFAOYSA-N 0.000 description 5
CNJOEMGIFXKJRC-UHFFFAOYSA-N n-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]-4-chloro-n-cyclopropylbenzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N(C1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1)C1CC1 CNJOEMGIFXKJRC-UHFFFAOYSA-N 0.000 description 5
JAEBDNUIPXAQCD-UHFFFAOYSA-N n-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-2-phenylacetamide Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1NC(=O)CC1=CC=CC=C1 JAEBDNUIPXAQCD-UHFFFAOYSA-N 0.000 description 5
GVHQWMPVVZCPSH-UHFFFAOYSA-N n-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-n-methylacetamide Chemical compound C1CC(N(C)C(C)=O)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 GVHQWMPVVZCPSH-UHFFFAOYSA-N 0.000 description 5
RGIJQBLXCIRDIX-UHFFFAOYSA-N n-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-n-methylmethanesulfonamide Chemical compound C1CC(N(C)S(C)(=O)=O)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 RGIJQBLXCIRDIX-UHFFFAOYSA-N 0.000 description 5
HGXCLIZMBKPLLN-UHFFFAOYSA-N n-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]formamide Chemical compound C1CC(NC=O)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 HGXCLIZMBKPLLN-UHFFFAOYSA-N 0.000 description 5
DHEMYZSPCMFSFY-UHFFFAOYSA-N n-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]methanesulfonamide Chemical compound C1CC(NS(=O)(=O)C)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 DHEMYZSPCMFSFY-UHFFFAOYSA-N 0.000 description 5
FIWPKUWTMFDONG-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]-n-butylbutan-1-amine Chemical compound C1=CC(OCCN(CCCC)CCCC)=CC=C1OC1=NC2=CC=CC=C2S1 FIWPKUWTMFDONG-UHFFFAOYSA-N 0.000 description 5
DSCVFOUPKTWHJW-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]-n-ethylcyclohexanamine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCN(CC)C1CCCCC1 DSCVFOUPKTWHJW-UHFFFAOYSA-N 0.000 description 5
DCLVFUYFBIWTRM-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-n-(cyclopropylmethyl)-3-(1h-1,2,4-triazol-5-yl)propan-1-amine Chemical compound N1=CNN=C1CCCN(CCC=1C=CC(OC=2SC3=CC=CC=C3N=2)=CC=1)CC1CC1 DCLVFUYFBIWTRM-UHFFFAOYSA-N 0.000 description 5
GUKGFCRRJHTNDV-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-n-(cyclopropylmethyl)-3-(2h-tetrazol-5-yl)propan-1-amine Chemical compound N1=NNN=C1CCCN(CCC=1C=CC(OC=2SC3=CC=CC=C3N=2)=CC=1)CC1CC1 GUKGFCRRJHTNDV-UHFFFAOYSA-N 0.000 description 5
IPBLCJCKLMTBHV-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-n-(cyclopropylmethyl)-3-(3-phenyl-1h-1,2,4-triazol-5-yl)propan-1-amine Chemical compound N=1NC(C=2C=CC=CC=2)=NC=1CCCN(CCC=1C=CC(OC=2SC3=CC=CC=C3N=2)=CC=1)CC1CC1 IPBLCJCKLMTBHV-UHFFFAOYSA-N 0.000 description 5
ISOYJSBJJMLCSP-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-n-(cyclopropylmethyl)-3-(5-methyl-1h-1,2,4-triazol-3-yl)propan-1-amine Chemical compound N1C(C)=NC(CCCN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC2CC2)=N1 ISOYJSBJJMLCSP-UHFFFAOYSA-N 0.000 description 5
GSFQGXNCYIDVAE-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-n-(cyclopropylmethyl)-3-(tetrazol-2-yl)propan-1-amine Chemical compound N1=CN=NN1CCCN(CCC=1C=CC(OC=2SC3=CC=CC=C3N=2)=CC=1)CC1CC1 GSFQGXNCYIDVAE-UHFFFAOYSA-N 0.000 description 5
VDIIVYZDERMYGR-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-n-[3-(2h-tetrazol-5-yl)propyl]cyclopropanamine Chemical compound N1=NNN=C1CCCN(CCC=1C=CC(OC=2SC3=CC=CC=C3N=2)=CC=1)C1CC1 VDIIVYZDERMYGR-UHFFFAOYSA-N 0.000 description 5
NTEKFVIMRQKTFZ-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-n-butylbutan-1-amine Chemical compound C1=CC(CCN(CCCC)CCCC)=CC=C1OC1=NC2=CC=CC=C2S1 NTEKFVIMRQKTFZ-UHFFFAOYSA-N 0.000 description 5
NBWVOFLMXYIKMJ-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-n-cyclopropyl-2-(2h-tetrazol-5-yl)acetamide Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(C1CC1)C(=O)CC=1N=NNN=1 NBWVOFLMXYIKMJ-UHFFFAOYSA-N 0.000 description 5
GOGSXZRAYQAMOD-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-n-ethylcyclohexanamine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CC)C1CCCCC1 GOGSXZRAYQAMOD-UHFFFAOYSA-N 0.000 description 5
PSNFNDVIDUOKFR-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-n-ethylcyclopropanamine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CC)C1CC1 PSNFNDVIDUOKFR-UHFFFAOYSA-N 0.000 description 5
PGNCKSDHQSASSK-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]cyclopropanamine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCNC1CC1 PGNCKSDHQSASSK-UHFFFAOYSA-N 0.000 description 5
JRXIQERDUYKZID-UHFFFAOYSA-N n-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]-n-butylbutan-1-amine Chemical compound C1=CC(OCCN(CCCC)CCCC)=CC=C1OC1=NC2=CC=CC=C2O1 JRXIQERDUYKZID-UHFFFAOYSA-N 0.000 description 5
FOSPOHCMRIJVNH-UHFFFAOYSA-N n-[2-[4-(1h-benzimidazol-2-yloxy)phenoxy]ethyl]-n-ethylcyclohexanamine Chemical compound C=1C=C(OC=2NC3=CC=CC=C3N=2)C=CC=1OCCN(CC)C1CCCCC1 FOSPOHCMRIJVNH-UHFFFAOYSA-N 0.000 description 5
NYUXYLIKMOXXIP-UHFFFAOYSA-N n-[2-[4-(1h-benzimidazol-2-yloxy)phenyl]ethyl]-n-(cyclopropylmethyl)propan-1-amine Chemical compound C=1C=C(OC=2NC3=CC=CC=C3N=2)C=CC=1CCN(CCC)CC1CC1 NYUXYLIKMOXXIP-UHFFFAOYSA-N 0.000 description 5
VSHBSVJWEDWHDZ-UHFFFAOYSA-N n-[2-[4-(1h-benzimidazol-2-yloxy)phenyl]ethyl]-n-butylbutan-1-amine Chemical compound C1=CC(CCN(CCCC)CCCC)=CC=C1OC1=NC2=CC=CC=C2N1 VSHBSVJWEDWHDZ-UHFFFAOYSA-N 0.000 description 5
UUSZCASVPDNAGK-UHFFFAOYSA-N n-[2-[4-(1h-benzimidazol-2-yloxy)phenyl]ethyl]-n-ethylcyclohexanamine Chemical compound C=1C=C(OC=2NC3=CC=CC=C3N=2)C=CC=1CCN(CC)C1CCCCC1 UUSZCASVPDNAGK-UHFFFAOYSA-N 0.000 description 5
AFSRMHKPXBPUNT-UHFFFAOYSA-N n-[3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-(cyclopropylmethyl)amino]propyl]acetamide Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCNC(=O)C)CC1CC1 AFSRMHKPXBPUNT-UHFFFAOYSA-N 0.000 description 5
QIUOIFMABWOQPP-UHFFFAOYSA-N n-[3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-(cyclopropylmethyl)amino]propyl]methanesulfonamide Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCNS(=O)(=O)C)CC1CC1 QIUOIFMABWOQPP-UHFFFAOYSA-N 0.000 description 5
XPCVPNDXUNKFJU-UHFFFAOYSA-N n-[3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-(cyclopropylmethyl)amino]propyl]morpholine-4-carboxamide Chemical compound C1COCCN1C(=O)NCCCN(CCC=1C=CC(OC=2SC3=CC=CC=C3N=2)=CC=1)CC1CC1 XPCVPNDXUNKFJU-UHFFFAOYSA-N 0.000 description 5
UTDIYPPRKWQRNP-UHFFFAOYSA-N n-[3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]propyl]-2-hydroxyacetamide Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCNC(=O)CO)C1CC1 UTDIYPPRKWQRNP-UHFFFAOYSA-N 0.000 description 5
ARJJEYABAHZLNG-UHFFFAOYSA-N n-[3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]propyl]-2-methylpropanamide Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCNC(=O)C(C)C)C1CC1 ARJJEYABAHZLNG-UHFFFAOYSA-N 0.000 description 5
RNQICXAMMRPUDL-UHFFFAOYSA-N n-[3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]propyl]-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCCCN(C1CC1)CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 RNQICXAMMRPUDL-UHFFFAOYSA-N 0.000 description 5
CKNNIXXSXJPDFK-UHFFFAOYSA-N n-[3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]propyl]acetamide Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCNC(=O)C)C1CC1 CKNNIXXSXJPDFK-UHFFFAOYSA-N 0.000 description 5
RJNBKACGGIPZSI-UHFFFAOYSA-N n-[3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]propyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NCCCN(CCC=1C=CC(OC=2SC3=CC=CC=C3N=2)=CC=1)C1CC1 RJNBKACGGIPZSI-UHFFFAOYSA-N 0.000 description 5
LIYJFLBFLXWRQB-UHFFFAOYSA-N n-[3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]propyl]methanesulfonamide Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCNS(=O)(=O)C)C1CC1 LIYJFLBFLXWRQB-UHFFFAOYSA-N 0.000 description 5
POUPURSWOWAMCD-UHFFFAOYSA-N n-[3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]propyl]oxolane-2-carboxamide Chemical compound C1CCOC1C(=O)NCCCN(CCC=1C=CC(OC=2SC3=CC=CC=C3N=2)=CC=1)C1CC1 POUPURSWOWAMCD-UHFFFAOYSA-N 0.000 description 5
XSVRXLMLAYLDMS-UHFFFAOYSA-N n-[3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]propyl]propane-2-sulfonamide;trifluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)F.C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCNS(=O)(=O)C(C)C)C1CC1 XSVRXLMLAYLDMS-UHFFFAOYSA-N 0.000 description 5
OGPDRHICJZQAJN-UHFFFAOYSA-N n-[3-[4-(1,3-benzoxazol-2-yloxy)phenyl]propyl]-n-butylbutan-1-amine Chemical compound C1=CC(CCCN(CCCC)CCCC)=CC=C1OC1=NC2=CC=CC=C2O1 OGPDRHICJZQAJN-UHFFFAOYSA-N 0.000 description 5
FAIMVYCQWFVUID-UHFFFAOYSA-N n-ethyl-n-[2-[4-(1-methylbenzimidazol-2-yl)oxyphenyl]ethyl]cyclohexanamine Chemical compound C=1C=C(OC=2N(C3=CC=CC=C3N=2)C)C=CC=1CCN(CC)C1CCCCC1 FAIMVYCQWFVUID-UHFFFAOYSA-N 0.000 description 5
XPARKDXSLNZXAB-UHFFFAOYSA-N phenyl n'-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-n-cyanocarbamimidate Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1NC(=NC#N)OC1=CC=CC=C1 XPARKDXSLNZXAB-UHFFFAOYSA-N 0.000 description 5
LJCQRMOXTNWQDA-UHFFFAOYSA-N 1-[1-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]-4-phenylpiperidin-4-yl]ethanone Chemical compound C1CN(CCOC=2C=CC(OC=3OC4=CC=CC=C4N=3)=CC=2)CCC1(C(=O)C)C1=CC=CC=C1 LJCQRMOXTNWQDA-UHFFFAOYSA-N 0.000 description 4
UOCXFRCHBNYBCN-UHFFFAOYSA-N 1-[2-[4-(1,3-benzoxazol-2-ylmethyl)phenoxy]ethyl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1CCOC(C=C1)=CC=C1CC1=NC2=CC=CC=C2O1 UOCXFRCHBNYBCN-UHFFFAOYSA-N 0.000 description 4
UALALAOOEVHOAE-UHFFFAOYSA-N 1-[3-[4-(1,3-benzoxazol-2-yloxy)phenoxy]-2-hydroxypropyl]-4-phenylpiperidin-4-ol Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCC(O)CN(CC1)CCC1(O)C1=CC=CC=C1 UALALAOOEVHOAE-UHFFFAOYSA-N 0.000 description 4
NVSWCWWHQRVUDU-UHFFFAOYSA-N 2-[4-(2-morpholin-4-ylethoxy)phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCCN1CCOCC1 NVSWCWWHQRVUDU-UHFFFAOYSA-N 0.000 description 4
ZIQGASWXUSSORV-UHFFFAOYSA-N 2-[4-(2-piperidin-1-ylethoxy)phenoxy]-1,3-benzoxazole Chemical group C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCCN1CCCCC1 ZIQGASWXUSSORV-UHFFFAOYSA-N 0.000 description 4
DDPDHHQNYWOFTO-UHFFFAOYSA-N 2-[4-(2-piperidin-1-ylethyl)phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1CCN1CCCCC1 DDPDHHQNYWOFTO-UHFFFAOYSA-N 0.000 description 4
NNHHNGXLAAEJGV-UHFFFAOYSA-N 2-[4-(2-pyrrolidin-1-ylethoxy)phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCCN1CCCC1 NNHHNGXLAAEJGV-UHFFFAOYSA-N 0.000 description 4
SSQAGYBYJTZVJM-UHFFFAOYSA-N 2-[4-(2-pyrrolidin-1-ylethyl)phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1CCN1CCCC1 SSQAGYBYJTZVJM-UHFFFAOYSA-N 0.000 description 4
KPAQPCYFUAKHTL-UHFFFAOYSA-N 2-[4-(3-piperidin-1-ylpropyl)phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1CCCN1CCCCC1 KPAQPCYFUAKHTL-UHFFFAOYSA-N 0.000 description 4
RUOSQGLZVMYCMI-UHFFFAOYSA-N 2-[4-[2-(azepan-1-yl)ethoxy]phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCCN1CCCCCC1 RUOSQGLZVMYCMI-UHFFFAOYSA-N 0.000 description 4
JYGZPGXROUXHGB-UHFFFAOYSA-N 2-[4-[2-(azetidin-1-yl)ethoxy]phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCCN1CCC1 JYGZPGXROUXHGB-UHFFFAOYSA-N 0.000 description 4
OASLEWALRHQUOX-UHFFFAOYSA-N 2-[4-[3-(4-phenylpiperidin-1-yl)propoxy]phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCCCN(CC1)CCC1C1=CC=CC=C1 OASLEWALRHQUOX-UHFFFAOYSA-N 0.000 description 4
GOGNXTVASAKEPB-UHFFFAOYSA-N 3-[4-(1,3-benzoxazol-2-yloxy)phenyl]-n-(cyclopropylmethyl)-n-propylpropan-1-amine Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1CCCN(CCC)CC1CC1 GOGNXTVASAKEPB-UHFFFAOYSA-N 0.000 description 4
YUSFGYVLHMOYSH-UHFFFAOYSA-N 4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-methylsulfonylamino]butanoic acid Chemical compound C1=CC(CCN(CCCC(O)=O)S(=O)(=O)C)=CC=C1OC1=NC2=CC=CC=C2S1 YUSFGYVLHMOYSH-UHFFFAOYSA-N 0.000 description 4
239000004215 Carbon black (E152) Substances 0.000 description 4
SVIXKYOSUKPYTE-UHFFFAOYSA-N ethyl 1-[2-[4-(1,3-benzoxazol-2-ylmethyl)phenoxy]ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CCOC(C=C1)=CC=C1CC1=NC2=CC=CC=C2O1 SVIXKYOSUKPYTE-UHFFFAOYSA-N 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
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JP2006522022A 2003-07-28 2004-07-27 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 Expired - Fee Related JP4726238B2 (ja)