KR20060054408A - 벤즈이미다졸, 벤즈티아졸 및 벤즈옥사졸 유도체 및lta4 h 조정자로서의 그의 용도 - Google Patents
벤즈이미다졸, 벤즈티아졸 및 벤즈옥사졸 유도체 및lta4 h 조정자로서의 그의 용도 Download PDFInfo
- Publication number
- KR20060054408A KR20060054408A KR1020067002211A KR20067002211A KR20060054408A KR 20060054408 A KR20060054408 A KR 20060054408A KR 1020067002211 A KR1020067002211 A KR 1020067002211A KR 20067002211 A KR20067002211 A KR 20067002211A KR 20060054408 A KR20060054408 A KR 20060054408A
- Authority
- KR
- South Korea
- Prior art keywords
- yloxy
- benzothiazol
- benzyl
- piperidin
- 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.)
- Ceased
Links
- 102100022118 Leukotriene A-4 hydrolase Human genes 0.000 title claims abstract description 46
- UFPQIRYSPUYQHK-WAQVJNLQSA-N leukotriene A4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@@H]1O[C@H]1CCCC(O)=O UFPQIRYSPUYQHK-WAQVJNLQSA-N 0.000 title description 5
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title 1
- 101100455054 Homo sapiens LTA4H gene Proteins 0.000 title 1
- 101100075025 Scheffersomyces stipitis (strain ATCC 58785 / CBS 6054 / NBRC 10063 / NRRL Y-11545) LTA4 gene Proteins 0.000 title 1
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 68
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 62
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 31
- 201000010099 disease Diseases 0.000 claims abstract description 29
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 20
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 16
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 15
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 13
- 230000000694 effects Effects 0.000 claims abstract description 12
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- 125000000217 alkyl group Chemical group 0.000 claims description 233
- 238000000034 method Methods 0.000 claims description 212
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 54
- 125000004429 atom Chemical group 0.000 claims description 44
- 229920006395 saturated elastomer Polymers 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 239000008194 pharmaceutical composition Substances 0.000 claims description 37
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 22
- 150000001408 amides Chemical class 0.000 claims description 21
- 125000003386 piperidinyl group Chemical group 0.000 claims description 19
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 18
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
- 229910052727 yttrium Inorganic materials 0.000 claims description 18
- 230000001404 mediated effect Effects 0.000 claims description 17
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- MBGDQOYOKOUJOX-UHFFFAOYSA-N 1-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-4-hydroxypyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 MBGDQOYOKOUJOX-UHFFFAOYSA-N 0.000 claims description 14
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 150000001721 carbon Chemical group 0.000 claims description 14
- 125000004193 piperazinyl group Chemical group 0.000 claims description 14
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 201000001320 Atherosclerosis Diseases 0.000 claims description 12
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
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- 201000004681 Psoriasis Diseases 0.000 claims description 11
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 11
- BUZBVOKDNAZIIM-UHFFFAOYSA-N 1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 BUZBVOKDNAZIIM-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- IJHSPFFWIXGDBB-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-2-hydroxyacetamide Chemical compound C1CC(NC(=O)CO)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 IJHSPFFWIXGDBB-UHFFFAOYSA-N 0.000 claims description 10
- UBVVZACYWWPTID-UHFFFAOYSA-N 1-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]pyrrolidin-2-one Chemical compound O=C1CCCN1C1CCN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 UBVVZACYWWPTID-UHFFFAOYSA-N 0.000 claims description 9
- NUFHDURBLSHZNX-UHFFFAOYSA-N 1-[4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazin-1-yl]-2-hydroxyethanone Chemical compound C1CN(C(=O)CO)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 NUFHDURBLSHZNX-UHFFFAOYSA-N 0.000 claims description 9
- WNCUSFCVRSUOKM-UHFFFAOYSA-N 2-[2-fluoro-4-(piperidin-1-ylmethyl)phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C(F)=CC=1CN1CCCCC1 WNCUSFCVRSUOKM-UHFFFAOYSA-N 0.000 claims description 9
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- YNNJLQSGXCRFPI-UHFFFAOYSA-N 4-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]morpholin-3-one Chemical compound O=C1COCCN1C1CCN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 YNNJLQSGXCRFPI-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- CDIFBWHQJIJSMM-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-n-methylmethanesulfonamide Chemical compound C1CC(N(C)S(C)(=O)=O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 CDIFBWHQJIJSMM-UHFFFAOYSA-N 0.000 claims description 9
- NXAVSLLJRLFRGB-UHFFFAOYSA-N n-[[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]methyl]methanesulfonamide Chemical compound C1CC(CNS(=O)(=O)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 NXAVSLLJRLFRGB-UHFFFAOYSA-N 0.000 claims description 9
- IEPGXTISLYYPRB-UHFFFAOYSA-N n-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]cyclopropanamine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CNC1CC1 IEPGXTISLYYPRB-UHFFFAOYSA-N 0.000 claims description 9
- CREOVZBMIBKVON-UHFFFAOYSA-N 1-[2-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-cyclopropylamino]ethyl]-4-hydroxypyrrolidin-2-one Chemical compound O=C1CC(O)CN1CCN(C1CC1)CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 CREOVZBMIBKVON-UHFFFAOYSA-N 0.000 claims description 8
- BTYHUCROUVOSFY-UHFFFAOYSA-N 1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-amine Chemical compound C1CC(N)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 BTYHUCROUVOSFY-UHFFFAOYSA-N 0.000 claims description 8
- CFTXJKKITUELKJ-UHFFFAOYSA-N 1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 CFTXJKKITUELKJ-UHFFFAOYSA-N 0.000 claims description 8
- ZVDOMASQJBYMSO-UHFFFAOYSA-N 2-[4-(piperidin-1-ylmethyl)phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1CN1CCCCC1 ZVDOMASQJBYMSO-UHFFFAOYSA-N 0.000 claims description 8
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- 239000003814 drug Substances 0.000 claims description 8
- BLZWKGRUUCYVQX-UHFFFAOYSA-N ethyl 1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 BLZWKGRUUCYVQX-UHFFFAOYSA-N 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 201000006417 multiple sclerosis Diseases 0.000 claims description 8
- ZYPGCBNIVHGWEP-UHFFFAOYSA-N n'-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]-n'-cyclopropylethane-1,2-diamine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CN(CCN)C1CC1 ZYPGCBNIVHGWEP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
- VBSFMULSLZYRBF-UHFFFAOYSA-N tert-butyl 4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 VBSFMULSLZYRBF-UHFFFAOYSA-N 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- OLNZZRQBURBGNP-UHFFFAOYSA-N tert-butyl n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-n-methylcarbamate Chemical compound C1CC(N(C)C(=O)OC(C)(C)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 OLNZZRQBURBGNP-UHFFFAOYSA-N 0.000 claims description 8
- MTCVACVHFGWJTC-UHFFFAOYSA-N tert-butyl n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 MTCVACVHFGWJTC-UHFFFAOYSA-N 0.000 claims description 8
- ZMABICQDXQLGNS-UHFFFAOYSA-N tert-butyl n-[2-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-cyclopropylamino]ethyl]carbamate Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CN(CCNC(=O)OC(C)(C)C)C1CC1 ZMABICQDXQLGNS-UHFFFAOYSA-N 0.000 claims description 8
- LFANTSMNOUDSSX-UHFFFAOYSA-N 1-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-1,3-dimethylurea Chemical compound C1CC(N(C)C(=O)NC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 LFANTSMNOUDSSX-UHFFFAOYSA-N 0.000 claims description 7
- VLRQVKLRWATZMA-UHFFFAOYSA-N 1-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-1-methylurea Chemical compound C1CC(N(C)C(N)=O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 VLRQVKLRWATZMA-UHFFFAOYSA-N 0.000 claims description 7
- LKTRZJPIGMYCSF-UHFFFAOYSA-N 1-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-3-ethylurea Chemical compound C1CC(NC(=O)NCC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 LKTRZJPIGMYCSF-UHFFFAOYSA-N 0.000 claims description 7
- IXLAMKLSAJZLBI-UHFFFAOYSA-N 1-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-3-methylurea Chemical compound C1CC(NC(=O)NC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 IXLAMKLSAJZLBI-UHFFFAOYSA-N 0.000 claims description 7
- HEUDZUWKEPAQLK-UHFFFAOYSA-N 1-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-3-propylurea Chemical compound C1CC(NC(=O)NCCC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 HEUDZUWKEPAQLK-UHFFFAOYSA-N 0.000 claims description 7
- WAYPBLZUXMHGFH-UHFFFAOYSA-N 1-[3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-cyclopropylamino]propyl]-3-propan-2-ylurea Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CN(CCCNC(=O)NC(C)C)C1CC1 WAYPBLZUXMHGFH-UHFFFAOYSA-N 0.000 claims description 7
- 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 description 7
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- QVVWRAAMUPSWRE-UHFFFAOYSA-N ethyl 3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methylamino]propanoate Chemical compound C1=CC(CNCCC(=O)OCC)=CC=C1OC1=NC2=CC=CC=C2S1 QVVWRAAMUPSWRE-UHFFFAOYSA-N 0.000 claims description 7
- 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 description 7
- 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 description 7
- GOKWQJTWJSUQNO-UHFFFAOYSA-N methyl n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 GOKWQJTWJSUQNO-UHFFFAOYSA-N 0.000 claims description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- XAXNYOONBNCDGS-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]methanesulfonamide Chemical compound C1CC(NS(=O)(=O)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 XAXNYOONBNCDGS-UHFFFAOYSA-N 0.000 claims description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- YIMRWBVVQPCHFH-UHFFFAOYSA-N n-[[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]methyl]-2,2,2-trifluoroacetamide Chemical compound C1CC(CNC(=O)C(F)(F)F)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 YIMRWBVVQPCHFH-UHFFFAOYSA-N 0.000 claims description 7
- TWQZWNFLIVWQNZ-UHFFFAOYSA-N phenyl n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]carbamate Chemical compound C1CN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1NC(=O)OC1=CC=CC=C1 TWQZWNFLIVWQNZ-UHFFFAOYSA-N 0.000 claims description 7
- NOTWVENCQZOQIZ-UHFFFAOYSA-N propan-2-yl n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OC(C)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 NOTWVENCQZOQIZ-UHFFFAOYSA-N 0.000 claims description 7
- 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 description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 239000012453 solvate Substances 0.000 claims description 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 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 description 6
- HFWIFRRHMZLJNF-UHFFFAOYSA-N 1-[3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-cyclopropylamino]propyl]-4-hydroxypyrrolidin-2-one Chemical compound O=C1CC(O)CN1CCCN(C1CC1)CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 HFWIFRRHMZLJNF-UHFFFAOYSA-N 0.000 claims description 6
- ZSLLLGHNYUBQPU-UHFFFAOYSA-N 1-[3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-cyclopropylamino]propyl]pyrrolidin-2-one Chemical compound O=C1CCCN1CCCN(C1CC1)CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 ZSLLLGHNYUBQPU-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- RPUNWQZSJVRXCM-UHFFFAOYSA-N 1-[3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methylamino]propyl]pyrrolidin-2-one Chemical compound O=C1CCCN1CCCNCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 RPUNWQZSJVRXCM-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 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 description 6
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 6
- IQTADKJWOJRVNV-UHFFFAOYSA-N 2-(4-ethylphenoxy)-1,3-benzothiazole Chemical compound C1=CC(CC)=CC=C1OC1=NC2=CC=CC=C2S1 IQTADKJWOJRVNV-UHFFFAOYSA-N 0.000 claims description 6
- GCSDZVIXDKZKFO-UHFFFAOYSA-N 2-(4-ethylphenoxy)-1,3-benzoxazole Chemical compound C1=CC(CC)=CC=C1OC1=NC2=CC=CC=C2O1 GCSDZVIXDKZKFO-UHFFFAOYSA-N 0.000 claims description 6
- HGLXZYVILQDPRO-UHFFFAOYSA-N 2-(4-ethylphenoxy)-1h-benzimidazole Chemical compound C1=CC(CC)=CC=C1OC1=NC2=CC=CC=C2N1 HGLXZYVILQDPRO-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- VLSBZKOXDMHPMI-UHFFFAOYSA-N 2-[4-[(4-methylsulfonylpiperazin-1-yl)methyl]phenoxy]-1,3-benzothiazole Chemical compound C1CN(S(=O)(=O)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 VLSBZKOXDMHPMI-UHFFFAOYSA-N 0.000 claims description 6
- TWOVNMNLKPYEMS-UHFFFAOYSA-N 2-[4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazin-1-yl]-1-morpholin-4-ylethanone Chemical compound C1CN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1CC(=O)N1CCOCC1 TWOVNMNLKPYEMS-UHFFFAOYSA-N 0.000 claims description 6
- ATWIRLATCCUTSE-UHFFFAOYSA-N 2-[4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazin-1-yl]-1-pyrrolidin-1-ylethanone Chemical compound C1CN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1CC(=O)N1CCCC1 ATWIRLATCCUTSE-UHFFFAOYSA-N 0.000 claims description 6
- KNKPLRVMSFXJDO-UHFFFAOYSA-N 2-[4-[[4-(benzenesulfonyl)piperazin-1-yl]methyl]phenoxy]-1,3-benzothiazole Chemical compound C1CN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1S(=O)(=O)C1=CC=CC=C1 KNKPLRVMSFXJDO-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- WJZIPMQUKSTHLV-UHFFFAOYSA-N 2-ethyldecanoic acid Chemical compound CCCCCCCCC(CC)C(O)=O WJZIPMQUKSTHLV-UHFFFAOYSA-N 0.000 claims description 6
- PCYYPXCCVPPBCQ-UHFFFAOYSA-N 3-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]-1,1-dimethylurea Chemical compound C1CC(NC(=O)N(C)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 PCYYPXCCVPPBCQ-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- MMPJZYXYNRYMQR-UHFFFAOYSA-N 4-chloro-2-[4-(piperidin-1-ylmethyl)phenoxy]-1,3-benzothiazole Chemical compound N=1C=2C(Cl)=CC=CC=2SC=1OC(C=C1)=CC=C1CN1CCCCC1 MMPJZYXYNRYMQR-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 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 description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 6
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 6
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 6
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- 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 1
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- RJUAEBLXGFKZMS-UHFFFAOYSA-N piperidin-1-ylmethanol Chemical compound OCN1CCCCC1 RJUAEBLXGFKZMS-UHFFFAOYSA-N 0.000 description 1
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- RNMPNVBLQHYANU-UHFFFAOYSA-N spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C12=CC=CC=C2C(=O)OC21CCNCC2 RNMPNVBLQHYANU-UHFFFAOYSA-N 0.000 description 1
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- VULLJZNHYDJBOE-UHFFFAOYSA-N tert-butyl 4-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]tetrazol-5-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=NN=NN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 VULLJZNHYDJBOE-UHFFFAOYSA-N 0.000 description 1
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- SUTMLQQIINZQMS-UHFFFAOYSA-N tert-butyl 9-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]-3,9-diazaspiro[5.5]undecane-3-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC11CCN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 SUTMLQQIINZQMS-UHFFFAOYSA-N 0.000 description 1
- TZRQZPMQUXEZMC-UHFFFAOYSA-N tert-butyl n-(2-bromoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCBr TZRQZPMQUXEZMC-UHFFFAOYSA-N 0.000 description 1
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- KONRDEGAZYJCLF-UHFFFAOYSA-N tert-butyl n-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 KONRDEGAZYJCLF-UHFFFAOYSA-N 0.000 description 1
- GVXWUAZHXAOVSW-UHFFFAOYSA-N tert-butyl n-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-n-methylcarbamate Chemical compound C1CC(N(C)C(=O)OC(C)(C)C)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 GVXWUAZHXAOVSW-UHFFFAOYSA-N 0.000 description 1
- RLKZWNLELPUMTF-UHFFFAOYSA-N tert-butyl n-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 RLKZWNLELPUMTF-UHFFFAOYSA-N 0.000 description 1
- UAZBGJSVKLMJLA-UHFFFAOYSA-N tert-butyl n-[2-[[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]methylcarbamoyl]cyclobutyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1CCC1C(=O)NCC1CCN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 UAZBGJSVKLMJLA-UHFFFAOYSA-N 0.000 description 1
- GGZZCWAVUPWCLT-UHFFFAOYSA-N tert-butyl n-[[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]methylsulfamoyl]carbamate Chemical compound C1CC(CNS(=O)(=O)NC(=O)OC(C)(C)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 GGZZCWAVUPWCLT-UHFFFAOYSA-N 0.000 description 1
- DJJOYDXRUBOZON-UHFFFAOYSA-N tert-butyl n-methyl-n-piperidin-4-ylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)C1CCNCC1 DJJOYDXRUBOZON-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 229960002663 thioctic acid Drugs 0.000 description 1
- 238000003325 tomography Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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- GSQBIOQCECCMOQ-UHFFFAOYSA-N β-alanine ethyl ester Chemical compound CCOC(=O)CCN GSQBIOQCECCMOQ-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/428—Thiazoles condensed with carbocyclic rings
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- Public Health (AREA)
- General Health & Medical Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pulmonology (AREA)
- Manufacturing & Machinery (AREA)
- Ceramic Engineering (AREA)
- Materials Engineering (AREA)
- Biomedical Technology (AREA)
- Structural Engineering (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Inorganic Chemistry (AREA)
- Psychiatry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49071003P | 2003-07-28 | 2003-07-28 | |
| US60/490,710 | 2003-07-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20060054408A true KR20060054408A (ko) | 2006-05-22 |
Family
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Family Applications (2)
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| KR1020067002194A Expired - Fee Related KR101149379B1 (ko) | 2003-07-28 | 2004-07-27 | 벤즈이미다졸, 벤즈티아졸 및 벤즈옥사졸 유도체 및lta4 h 조정자로서의 그의 용도 |
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| JP2008536825A (ja) * | 2005-03-31 | 2008-09-11 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | フェニルおよびピリジルlta4hモジュレータ |
| PL1877379T3 (pl) | 2005-04-13 | 2013-06-28 | Astex Therapeutics Ltd | Pochodne hydroksybenzamidu i ich wykorzystanie, jako inhibitorów hsp90 |
| EP1717235A3 (en) * | 2005-04-29 | 2007-02-28 | Bioprojet | Phenoxypropylpiperidines and -pyrrolidines and their use as histamine H3-receptor ligands |
| ES2359431T3 (es) * | 2005-09-02 | 2011-05-23 | F. Hoffmann-La Roche Ag | Derivados de benzooxazol, oxazolopiridina, benzotiazol y tiazolopiridina. |
| CA2623348A1 (en) * | 2005-09-21 | 2007-04-12 | Decode Genetics Ehf | Biaryl substituted heterocycle inhibitors of lta4h for treating inflammation |
| EP1968961A2 (en) * | 2005-12-21 | 2008-09-17 | Decode Genetics EHF | Biaryl nitrogen 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 |
| US7576102B2 (en) | 2005-12-21 | 2009-08-18 | Decode Genetics Ehf | Biaryl substituted nitrogen containing heterocycle inhibitors of LTA4H for treating inflammation |
| DK1976828T3 (en) | 2005-12-29 | 2017-03-06 | Celtaxsys Inc | DIAMINE DERIVATIVES AS INhibitors of Leukotriene A4 HYDROLASE |
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| US8115005B2 (en) | 2006-08-04 | 2012-02-14 | Decode Genetics Ehf. | Pyrazolylphenyl and pyrrolylphenyl inhibitors of LTA4H for treating inflammation |
| EP2066800A2 (en) | 2006-08-04 | 2009-06-10 | Decode Genetics EHF | Aryl amino acid derivatives as inhibitors of lta4h (leukotriene a4 hydrolase) for treating inflammation |
| US7728032B2 (en) * | 2006-08-04 | 2010-06-01 | Decode Genetics Ehf | Phenoxymethylalkyne inhibitors of LTA4H for treating inflammation |
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| US8277807B2 (en) | 2006-10-12 | 2012-10-02 | Astex Therapeutics Limited | Pharmaceutical combinations |
| EP2073803B1 (en) | 2006-10-12 | 2018-09-19 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US8883790B2 (en) | 2006-10-12 | 2014-11-11 | Astex Therapeutics Limited | Pharmaceutical combinations |
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| TW200906396A (en) * | 2007-02-14 | 2009-02-16 | Janssen Pharmaceutica Nv | LTA4H modulators and uses thereof |
| BRPI0808775A2 (pt) * | 2007-03-08 | 2017-05-30 | Irm Llc | compostos e composições como moduladores de atividade de gpr119 |
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| GB0806527D0 (en) | 2008-04-11 | 2008-05-14 | Astex Therapeutics Ltd | Pharmaceutical compounds |
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| JP5746685B2 (ja) | 2009-05-14 | 2015-07-08 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプJanssen Pharmaceutica Naamloze Vennootschap | ロイコトリエンa4加水分解酵素のモジュレーターとしての縮合二環式ヘテロアリール部分を2つ有する化合物 |
| 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 |
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| KR102390246B1 (ko) | 2016-12-21 | 2022-04-22 | 에프. 호프만-라 로슈 아게 | 항체의 시험관내 글리코조작에 있어서의 효소의 재사용 |
| 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 |
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| 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 |
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