JP2007500703A5 - - Google Patents
Download PDFInfo
- Publication number
- 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.)
- Pending
Links
- 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
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 125000004849 alkoxymethyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- IDONXSDVZAPFLV-UHFFFAOYSA-N ethyl 2-[4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 IDONXSDVZAPFLV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 238000009472 formulation Methods 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 239000000203 mixture Substances 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- TWQZWNFLIVWQNZ-UHFFFAOYSA-N phenyl n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]carbamate Chemical compound C1CN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1NC(=O)OC1=CC=CC=C1 TWQZWNFLIVWQNZ-UHFFFAOYSA-N 0.000 claims 1
- NOTWVENCQZOQIZ-UHFFFAOYSA-N propan-2-yl n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OC(C)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 NOTWVENCQZOQIZ-UHFFFAOYSA-N 0.000 claims 1
- HJQIDMVXPRRKNS-UHFFFAOYSA-N propyl n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OCCC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 HJQIDMVXPRRKNS-UHFFFAOYSA-N 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 230000001629 suppression Effects 0.000 claims 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007500703A JP2007500703A (ja) | 2007-01-18 |
| JP2007500703A5 true JP2007500703A5 (https=) | 2007-09-20 |
Family
ID=34115427
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006521973A Pending JP2007500703A (ja) | 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 |
| JP2006522022A Expired - Fee Related JP4726238B2 (ja) | 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 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006522022A Expired - Fee Related JP4726238B2 (ja) | 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 |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US20050043379A1 (https=) |
| EP (2) | EP1660492B1 (https=) |
| JP (2) | JP2007500703A (https=) |
| KR (2) | KR20060054408A (https=) |
| CN (2) | CN1856490A (https=) |
| AR (2) | AR045729A1 (https=) |
| AT (2) | ATE405562T1 (https=) |
| AU (2) | AU2004261610B2 (https=) |
| BR (2) | BRPI0412345A (https=) |
| CA (2) | CA2534212A1 (https=) |
| CY (1) | CY1108560T1 (https=) |
| DE (2) | DE602004015620D1 (https=) |
| DK (2) | DK1660492T3 (https=) |
| ES (2) | ES2311858T3 (https=) |
| HR (2) | HRP20060041B1 (https=) |
| IL (1) | IL173372A (https=) |
| MY (1) | MY145080A (https=) |
| NO (2) | NO20060771L (https=) |
| NZ (2) | NZ544970A (https=) |
| PL (2) | PL1660491T3 (https=) |
| PT (2) | PT1660492E (https=) |
| RU (2) | RU2373204C2 (https=) |
| SG (2) | SG129449A1 (https=) |
| SI (2) | SI1660491T1 (https=) |
| TW (2) | TWI362383B (https=) |
| UA (2) | UA82888C2 (https=) |
| WO (2) | WO2005012297A1 (https=) |
| ZA (2) | ZA200601716B (https=) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1856490A (zh) * | 2003-07-28 | 2006-11-01 | 詹森药业有限公司 | 苯并咪唑、苯并噻唑和苯并噁唑衍生物及其作为lta4h调节剂的应用 |
| US20060223792A1 (en) * | 2005-03-31 | 2006-10-05 | Butler Christopher R | Phenyl and pyridyl LTA4H modulators |
| KR101411167B1 (ko) | 2005-04-13 | 2014-06-23 | 아스텍스 테라퓨틱스 리미티드 | 하이드록시벤즈아미드 유도체 및 ｈｓｐ90 억제제로서의이의 용도 |
| EP1717235A3 (en) * | 2005-04-29 | 2007-02-28 | Bioprojet | Phenoxypropylpiperidines and -pyrrolidines and their use as histamine H3-receptor ligands |
| ATE497959T1 (de) * | 2005-09-02 | 2011-02-15 | Hoffmann La Roche | Benzoxazol-, oxazolopyridin-, benzothiazol- und thiazolopyridinderivate |
| US20070078263A1 (en) | 2005-09-21 | 2007-04-05 | Decode Chemistry, Inc. | Biaryl substituted heterocycle inhibitors of lta4h for treating inflammation |
| US7750012B2 (en) * | 2005-12-21 | 2010-07-06 | Decode Genetics Ehf | Biaryl nitrogen-heterocycle inhibitors of LTA4H for treating inflammation |
| AU2006327245A1 (en) * | 2005-12-21 | 2007-06-28 | Decode Genetics Ehf | Biaryl substituted nitrogen containing heterocycle inhibitors of LTA4H for treating inflammation |
| CA2634699A1 (en) | 2005-12-21 | 2007-06-28 | Decode Genetics Ehf | N-linked aryl heteroaryl inhibitors of lta4h for treating inflammation |
| WO2007079078A1 (en) * | 2005-12-29 | 2007-07-12 | Bayer Schering Pharma Aktiengesellschaft | Diamine derivatives as inhibitors of leukotriene a4 hydrolase |
| JP2009525269A (ja) * | 2006-01-30 | 2009-07-09 | ユーロ−セルティーク エス．エイ． | カルシウムチャネルブロッカーとしての環状尿素化合物 |
| US7754725B2 (en) | 2006-03-01 | 2010-07-13 | Astex Therapeutics Ltd. | Dihydroxyphenyl isoindolymethanones |
| US7951829B2 (en) * | 2006-05-03 | 2011-05-31 | Janssen Pharmaceutica Nv | Benzimidazole modulators of VR1 |
| AU2007260356B2 (en) * | 2006-06-16 | 2013-01-24 | H. Lundbeck A/S | Crystalline forms of 4- [2- (4-methylphenylsulfanyl) -phenyl] piperidine with combined serotonin and norepinephrine reuptake inhibition for the treatment of neuropathic pain |
| WO2008019284A1 (en) * | 2006-08-04 | 2008-02-14 | Decode Genetics Ehf | Phenoxymethylalkyne inhibitors of lta4h for treating inflammation |
| US8115005B2 (en) | 2006-08-04 | 2012-02-14 | Decode Genetics Ehf. | Pyrazolylphenyl and pyrrolylphenyl inhibitors of LTA4H for treating inflammation |
| WO2008019306A2 (en) * | 2006-08-04 | 2008-02-14 | Decode Genetics Ehf | Aryl amino acid derivatives as inhibitors of lta4h (leukotriene a4 hydrolase) for treating inflammation |
| EP2073802A1 (en) | 2006-10-12 | 2009-07-01 | Astex Therapeutics Limited | Pharmaceutical combinations |
| JP5518478B2 (ja) | 2006-10-12 | 2014-06-11 | 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 |
| JP5528807B2 (ja) | 2006-10-12 | 2014-06-25 | アステックス、セラピューティックス、リミテッド | 複合薬剤 |
| WO2008044041A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
| GB0620259D0 (en) | 2006-10-12 | 2006-11-22 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| TW200906396A (en) * | 2007-02-14 | 2009-02-16 | Janssen Pharmaceutica Nv | LTA4H modulators and uses thereof |
| EP2134704B1 (en) * | 2007-03-08 | 2010-09-22 | Irm Llc | Compounds and compositions as modulators of gpr119 activity |
| JPWO2008120710A1 (ja) * | 2007-03-30 | 2010-07-15 | パナソニック電工株式会社 | 活動強度計 |
| AR069126A1 (es) * | 2007-10-31 | 2009-12-30 | Janssen Pharmaceutica Nv | Diaminas en puente o fusionadas sustituidas con arilo como moduladores de leucotrieno a4 hidrolasa |
| EP2231159A1 (en) * | 2007-11-16 | 2010-09-29 | Abbott Laboratories | Method of treating arthritis |
| SI2336125T1 (sl) * | 2008-04-11 | 2013-04-30 | Janssen Pharmaceutica N.V. | Tiazolopiridin-2-iloksi-fenil in tiazolopirazin-2-iloksi-fenil amini kot modulatorji levkotrien a4 hidrolaze |
| GB0806527D0 (en) | 2008-04-11 | 2008-05-14 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| EP2294066B9 (en) | 2008-04-28 | 2015-03-11 | Janssen Pharmaceutica, N.V. | Benzoimidazoles as prolyl hydroxylase inhibitors |
| CN102459251B (zh) * | 2009-05-14 | 2015-05-20 | 詹森药业有限公司 | 作为白三烯a4水解酶的调节剂的具有两个稠合双环杂芳基部分的化合物 |
| CN102442962A (zh) * | 2010-11-10 | 2012-05-09 | 江苏德峰药业有限公司 | 1-烷基四氮唑的生产方法 |
| CN102442961A (zh) * | 2010-11-10 | 2012-05-09 | 江苏德峰药业有限公司 | 1-甲基四氮唑的生产方法 |
| US9273034B2 (en) | 2011-10-25 | 2016-03-01 | Janssen Pharmaceutica Nv | Meglumine salt formulations of 1-(5,6-dichloro-1H-benzo[D]imidazol-2-yl)-1H-pyrazole-4-carboxylic acid |
| ES2864862T3 (es) | 2013-03-12 | 2021-10-14 | Celltaxis Llc | Métodos de inhibición de la leucotrieno A4 hidrolasa |
| MX2015011677A (es) | 2013-03-14 | 2016-07-08 | Celtaxsys Inc | Inhibidores de leucotrieno a4 hidrolasa. |
| WO2014152536A2 (en) | 2013-03-14 | 2014-09-25 | Celtaxsys, Inc. | Inhibitors of leukotriene a4 hydrolase |
| RU2678196C2 (ru) | 2013-03-14 | 2019-01-24 | Селтакссис, Инк. | Производные 2-фениламино-3-цианопиразоло[1,5-а]пиримидина, полезные в качестве ингибитора лейкотриен-a4-гидролазы |
| ME02896B (me) * | 2013-12-17 | 2018-04-20 | Lilly Co Eli | Fenoksietilni derivati prstenastog amina i njihova aktivnost kao modulatora receptora ep4 |
| US10752588B2 (en) | 2014-12-19 | 2020-08-25 | The Broad Institute, Inc. | Dopamine D2 receptor ligands |
| WO2016100940A1 (en) | 2014-12-19 | 2016-06-23 | The Broad Institute, Inc. | Dopamine d2 receptor ligands |
| DK3307734T3 (da) | 2015-06-09 | 2020-01-27 | Abbvie Inc | Nukleære receptormodulatorer (ror) til behandling af inflammatoriske og autoimmune sygdomme |
| MX2019006123A (es) | 2016-12-21 | 2019-08-12 | Hoffmann La Roche | Metodo para glicomanipulacion in vitro de anticuerpos. |
| EP3559250A1 (en) | 2016-12-21 | 2019-10-30 | H. Hoffnabb-La Roche Ag | Re-use of enzymes in in vitro glycoengineering of antibodies |
| CN107663192B (zh) * | 2017-11-03 | 2019-05-10 | 梯尔希（南京）药物研发有限公司 | 一种雷贝拉唑杂质的制备方法 |
| EP3801559B1 (en) | 2018-05-31 | 2025-01-01 | Celltaxis, LLC | Method of reducing pulmonary exacerbations in respiratory disease patients |
| US20210393621A1 (en) | 2018-10-26 | 2021-12-23 | The Research Foundation For The State University Of New York | Combination serotonin specific reuptake inhibitor and serotonin 1a receptor partial agonist for reducing l-dopa-induced dyskinesia |
| EP3908278A4 (en) * | 2019-01-11 | 2022-09-28 | Naegis Pharmaceuticals Inc. | INHIBITORS OF LEUKOTRIEN SYNTHESIS |
| CN110026557B (zh) * | 2019-05-28 | 2021-08-27 | 南方科技大学 | 一种混合固体颗粒重熔的直写装置及成型方法 |
| KR20230123954A (ko) * | 2020-11-19 | 2023-08-24 | 텔로 테라퓨틱스, 인코포레이티드 | 소분자 화합물 및 조성물 |
| US11932630B2 (en) * | 2021-04-16 | 2024-03-19 | Novartis Ag | Heteroaryl aminopropanol derivatives |
| CN113683491A (zh) * | 2021-09-01 | 2021-11-23 | 王传良 | 一种4-(2-溴乙基)苯酚的制备方法 |
| CN113735798B (zh) * | 2021-09-27 | 2022-07-12 | 安徽美致诚药业有限公司 | 一种盐酸罗沙替丁醋酸酯的制备方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4873346A (en) * | 1985-09-20 | 1989-10-10 | The Upjohn Company | Substituted benzothiazoles, benzimidazoles, and benzoxazoles |
| CA1319144C (en) * | 1986-11-14 | 1993-06-15 | Quirico Branca | Tetrahydronaphthalene derivatives |
| IL90337A0 (en) * | 1988-05-24 | 1989-12-15 | Pfizer | Aromatic and heterocyclic carboxamide derivatives as antineoplastic agents |
| IT1240598B (it) * | 1990-03-13 | 1993-12-17 | Mini Ricerca Scient Tecnolog | Derivati amminici ad azione antifungina |
| US5585492A (en) * | 1994-10-11 | 1996-12-17 | G. D. Searle & Co. | LTA4 Hydrolase inhibitors |
| US5889006A (en) * | 1995-02-23 | 1999-03-30 | Schering Corporation | Muscarinic antagonists |
| IL117149A0 (en) * | 1995-02-23 | 1996-06-18 | Schering Corp | Muscarinic antagonists |
| US5925654A (en) * | 1997-03-12 | 1999-07-20 | G.D. Searle & Co. | LTA4 , hydrolase inhibitors |
| EP1062216A1 (en) * | 1998-02-25 | 2000-12-27 | Genetics Institute, Inc. | Inhibitors of phospholipase a2 |
| US6514964B1 (en) * | 1999-09-27 | 2003-02-04 | Amgen Inc. | Fused cycloheptane and fused azacycloheptane compounds and their methods of use |
| US20040110757A1 (en) * | 2002-03-21 | 2004-06-10 | Thomas Arrhenius | Flt-1 ligands and their uses in the treatment of diseases regulatable by angiogenesis |
| CN1856490A (zh) * | 2003-07-28 | 2006-11-01 | 詹森药业有限公司 | 苯并咪唑、苯并噻唑和苯并噁唑衍生物及其作为lta4h调节剂的应用 |
| US7541466B2 (en) * | 2003-12-23 | 2009-06-02 | Genzyme Corporation | Tetrahydroisoquinoline derivatives for treating protein trafficking diseases |
| ES2570332T3 (es) * | 2005-03-16 | 2016-05-17 | Meda Pharma Gmbh & Co Kg | La combinación de anticolinérgicos y antagonistas del receptor de leucotrieno para el tratamiento de enfermedades respiratorias |
| TW200906396A (en) * | 2007-02-14 | 2009-02-16 | Janssen Pharmaceutica Nv | LTA4H modulators and uses thereof |
-
2004
- 2004-07-27 CN CNA2004800279067A patent/CN1856490A/zh active Pending
- 2004-07-27 AU AU2004261610A patent/AU2004261610B2/en not_active Ceased
- 2004-07-27 DK DK04779375T patent/DK1660492T3/da active
- 2004-07-27 DE DE602004015620T patent/DE602004015620D1/de not_active Expired - Lifetime
- 2004-07-27 SG SG200700691A patent/SG129449A1/en unknown
- 2004-07-27 DE DE602004016002T patent/DE602004016002D1/de not_active Expired - Lifetime
- 2004-07-27 SG SG200700817-0A patent/SG130192A1/en unknown
- 2004-07-27 EP EP04779375A patent/EP1660492B1/en not_active Expired - Lifetime
- 2004-07-27 ES ES04779219T patent/ES2311858T3/es not_active Expired - Lifetime
- 2004-07-27 RU RU2006102510/04A patent/RU2373204C2/ru not_active IP Right Cessation
- 2004-07-27 CA CA002534212A patent/CA2534212A1/en not_active Abandoned
- 2004-07-27 KR KR1020067002211A patent/KR20060054408A/ko not_active Ceased
- 2004-07-27 CN CN200480028138A patent/CN100591679C/zh not_active Expired - Fee Related
- 2004-07-27 ES ES04779375T patent/ES2313079T3/es not_active Expired - Lifetime
- 2004-07-27 US US10/900,152 patent/US20050043379A1/en not_active Abandoned
- 2004-07-27 SI SI200430904T patent/SI1660491T1/sl unknown
- 2004-07-27 UA UAA200601432A patent/UA82888C2/uk unknown
- 2004-07-27 EP EP04779219A patent/EP1660491B1/en not_active Expired - Lifetime
- 2004-07-27 BR BRPI0412345-0A patent/BRPI0412345A/pt not_active IP Right Cessation
- 2004-07-27 JP JP2006521973A patent/JP2007500703A/ja active Pending
- 2004-07-27 AU AU2004261628A patent/AU2004261628B2/en not_active Ceased
- 2004-07-27 DK DK04779219T patent/DK1660491T3/da active
- 2004-07-27 PL PL04779219T patent/PL1660491T3/pl unknown
- 2004-07-27 US US10/900,103 patent/US20050043378A1/en not_active Abandoned
- 2004-07-27 NZ NZ544970A patent/NZ544970A/en unknown
- 2004-07-27 AT AT04779375T patent/ATE405562T1/de active
- 2004-07-27 KR KR1020067002194A patent/KR101149379B1/ko not_active Expired - Fee Related
- 2004-07-27 SI SI200430927T patent/SI1660492T1/sl unknown
- 2004-07-27 PT PT04779375T patent/PT1660492E/pt unknown
- 2004-07-27 JP JP2006522022A patent/JP4726238B2/ja not_active Expired - Fee Related
- 2004-07-27 BR BRPI0413072-3A patent/BRPI0413072A/pt not_active IP Right Cessation
- 2004-07-27 HR HRP20060041AA patent/HRP20060041B1/hr not_active IP Right Cessation
- 2004-07-27 PT PT04779219T patent/PT1660491E/pt unknown
- 2004-07-27 WO PCT/US2004/024309 patent/WO2005012297A1/en not_active Ceased
- 2004-07-27 NZ NZ544938A patent/NZ544938A/en unknown
- 2004-07-27 PL PL04779375T patent/PL1660492T3/pl unknown
- 2004-07-27 WO PCT/US2004/024050 patent/WO2005012296A1/en not_active Ceased
- 2004-07-27 RU RU2006102508/04A patent/RU2359970C2/ru not_active IP Right Cessation
- 2004-07-27 CA CA002534228A patent/CA2534228A1/en not_active Abandoned
- 2004-07-27 UA UAA200601433A patent/UA87986C2/uk unknown
- 2004-07-27 HR HR20060039A patent/HRP20060039A2/xx not_active Application Discontinuation
- 2004-07-27 AT AT04779219T patent/ATE403654T1/de not_active IP Right Cessation
- 2004-07-28 TW TW093122570A patent/TWI362383B/zh not_active IP Right Cessation
- 2004-07-28 MY MYPI20043045A patent/MY145080A/en unknown
- 2004-07-28 AR ARP040102682A patent/AR045729A1/es unknown
- 2004-07-28 TW TW093122566A patent/TW200520756A/zh unknown
- 2004-07-28 AR ARP040102683A patent/AR045730A1/es not_active Application Discontinuation
-
2006
- 2006-01-26 IL IL173372A patent/IL173372A/en not_active IP Right Cessation
- 2006-02-17 NO NO20060771A patent/NO20060771L/no not_active Application Discontinuation
- 2006-02-20 NO NO20060823A patent/NO20060823L/no not_active Application Discontinuation
- 2006-02-27 ZA ZA200601716A patent/ZA200601716B/en unknown
- 2006-02-27 ZA ZA200601720A patent/ZA200601720B/en unknown
-
2008
- 2008-10-27 CY CY20081101220T patent/CY1108560T1/el unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2007500703A5 (https=) | ||
| RU2006102508A (ru) | Производные бензимидазола, бензотиазола и бензоксазола и их применение в качестве модуляторов lta4h | |
| JP2007500706A5 (https=) | ||
| US6090807A (en) | Use of heterocyclic compounds | |
| JP2008536825A5 (https=) | ||
| US7709486B2 (en) | CXCR4 antagonists | |
| US7767665B2 (en) | 1,3-benzothiazinone derivatives and use thereof | |
| RU2606497C2 (ru) | Тиазолилфенилбензолсульфонамидопроизводные в качестве ингибиторов киназ | |
| KR101585848B1 (ko) | 관절염의 치료 방법 | |
| JP2014525444A5 (https=) | ||
| JP5689119B2 (ja) | ジヒドロピリミジン化合物及び合成方法、医薬組成物及びその使用 | |
| US5958923A (en) | Use of thiazole and thiadiazole compounds | |
| JP2012510523A5 (https=) | ||
| US4452799A (en) | Benzisothiazole and benzisoxazole piperazine derivatives | |
| JP2020516671A5 (https=) | ||
| JP2010509372A5 (https=) | ||
| JP2004523535A5 (https=) | ||
| EP2331541B1 (en) | Indolizine inhibitors of leukotriene production | |
| JP2006506380A5 (https=) | ||
| WO2009121535A2 (en) | Antiproliferative compounds and therapeutic uses thereof | |
| JP4401384B2 (ja) | グルタミン酸受容体アンタゴニストであるイミダゾール誘導体 | |
| WO2003000245A1 (en) | Compounds for use in disorders associated with mast cell or basophil activity | |
| JP2006528147A5 (https=) | ||
| JP2009501745A5 (https=) | ||
| EP0010894A1 (en) | Antisecretory heterocyclic guanidine derivatives, process for their manufacture and pharmaceutical compositions containing them |