JP2007500703A5 - - Google Patents
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- JP2007500703A5 JP2007500703A5 JP2006521973A JP2006521973A JP2007500703A5 JP 2007500703 A5 JP2007500703 A5 JP 2007500703A5 JP 2006521973 A JP2006521973 A JP 2006521973A JP 2006521973 A JP2006521973 A JP 2006521973A JP 2007500703 A5 JP2007500703 A5 JP 2007500703A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- benzothiazol
- yloxy
- benzyl
- group
- Prior art date
- 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.)
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 62
- 229910052757 nitrogen Inorganic materials 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- 125000003386 piperidinyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 140
- -1 1,3- dihydro - indol-2-one-1-yl Chemical group 0.000 claims 62
- 229910052799 carbon Inorganic materials 0.000 claims 39
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 35
- 125000005842 heteroatom Chemical group 0.000 claims 34
- 229910052717 sulfur Inorganic materials 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- 101000619898 Homo sapiens Leukotriene A-4 hydrolase Proteins 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 102100022118 Leukotriene A-4 hydrolase Human genes 0.000 claims 6
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 101150008896 hetR gene Proteins 0.000 claims 4
- 229910052740 iodine Inorganic materials 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 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 2
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims 2
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 2
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- IDRGIXMWFWVVIO-UHFFFAOYSA-N 1-[[4-(1h-benzimidazol-2-yloxy)phenyl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2N1 IDRGIXMWFWVVIO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- PLMQGVLYXRYVOO-UHFFFAOYSA-N 2-[4-(piperidin-1-ylmethyl)phenoxy]-1h-benzimidazole Chemical compound C=1C=C(OC=2NC3=CC=CC=C3N=2)C=CC=1CN1CCCCC1 PLMQGVLYXRYVOO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- WMPGTMLVIHASJI-UHFFFAOYSA-N 2-[[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]amino]-2-oxoacetic acid Chemical compound C1CC(NC(=O)C(=O)O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 WMPGTMLVIHASJI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 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 1
- 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 1
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- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (2)
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| US49071003P | 2003-07-28 | 2003-07-28 | |
| PCT/US2004/024050 WO2005012296A1 (en) | 2003-07-28 | 2004-07-27 | Benzimidazole, benzthiazole and benzoxazole derivatives and their use as lta4h modulators |
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| CA2603122A1 (en) * | 2005-03-31 | 2006-10-05 | Janssen Pharmaceutica N.V. | Phenyl and pyridyl lta4h modulators |
| JP5154406B2 (ja) | 2005-04-13 | 2013-02-27 | アステックス、セラピューティックス、リミテッド | 医薬化合物 |
| EP1717235A3 (en) * | 2005-04-29 | 2007-02-28 | Bioprojet | Phenoxypropylpiperidines and -pyrrolidines and their use as histamine H3-receptor ligands |
| CA2620127A1 (en) * | 2005-09-02 | 2007-03-08 | F. Hoffmann-La Roche Ag | Benzooxazole, oxazolopyridine, benzothiazole and thiazolopyridine derivatives |
| JP5133889B2 (ja) * | 2005-09-21 | 2013-01-30 | デコード ジェネティクス イーエイチエフ | 炎症治療のためのビアリール基置換複素環ｌｔａ４ｈ阻害剤 |
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| AU2014249168B2 (en) | 2013-03-12 | 2018-07-12 | Celltaxis, Llc | Methods of inhibiting leukotriene A4 hydrolase |
| BR112015022864A8 (pt) | 2013-03-14 | 2019-11-26 | Celtaxsys Inc | composto, composição farmacêutica e uso dos mesmos |
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| TW200906396A (en) * | 2007-02-14 | 2009-02-16 | Janssen Pharmaceutica Nv | LTA4H modulators and uses thereof |
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