JP2015512888A5 - - Google Patents
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- Publication number
- JP2015512888A5 JP2015512888A5 JP2014561023A JP2014561023A JP2015512888A5 JP 2015512888 A5 JP2015512888 A5 JP 2015512888A5 JP 2014561023 A JP2014561023 A JP 2014561023A JP 2014561023 A JP2014561023 A JP 2014561023A JP 2015512888 A5 JP2015512888 A5 JP 2015512888A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- dioxino
- pyridin
- benzyl
- carboxylic acid
- 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.)
- Granted
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- -1 2,3-dihydro- [1,4] dioxino [2,3-b] pyridin-3-yl Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 3
- CMZILUOUJISOKH-AQDPXUSMSA-N C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1[C@@H]2CC[C@H]1CC(NC(=O)N)C2 Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1[C@@H]2CC[C@H]1CC(NC(=O)N)C2 CMZILUOUJISOKH-AQDPXUSMSA-N 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 150000002617 leukotrienes Chemical class 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- FMPJVWICZBWJJD-XYJFISCASA-N (1s,4s)-5-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-2,5-diazabicyclo[2.2.1]heptane-2-carboxamide Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1C[C@@]2([H])N(C(N)=O)C[C@]1([H])C2 FMPJVWICZBWJJD-XYJFISCASA-N 0.000 claims 1
- MSDDPTBJKVNZGD-IIBYNOLFSA-N (2r)-n-[1-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]piperidin-4-yl]-2-(methylamino)propanamide Chemical compound C1CC(NC(=O)[C@@H](C)NC)CCN1CC1=CC=C([C@@H]2OC3=NC=CC=C3OC2)C=C1 MSDDPTBJKVNZGD-IIBYNOLFSA-N 0.000 claims 1
- GVWBMNBXODYVGL-HSZRJFAPSA-N (3s)-3-[4-[(4-pyridin-3-yloxypiperidin-1-yl)methyl]phenyl]-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine Chemical compound C=1C=C([C@@H]2OC3=NC=CC=C3OC2)C=CC=1CN(CC1)CCC1OC1=CC=CN=C1 GVWBMNBXODYVGL-HSZRJFAPSA-N 0.000 claims 1
- VUBYDPWGNIYJRX-SJLPKXTDSA-N (8ar)-7-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-5,6,8,8a-tetrahydro-1h-[1,3]oxazolo[3,4-a]pyrazin-3-one Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1C[C@@H]2COC(=O)N2CC1 VUBYDPWGNIYJRX-SJLPKXTDSA-N 0.000 claims 1
- KOVXXTVRXJEGAR-JENIJYKNSA-N 1-[(1s,4s)-5-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]-2-hydroxyethanone Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1C[C@@]2([H])N(C(=O)CO)C[C@]1([H])C2 KOVXXTVRXJEGAR-JENIJYKNSA-N 0.000 claims 1
- WBWMNHCLCKMTQT-CMKODMSKSA-N 1-[(1s,4s)-5-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]-2-methylsulfonylethanone Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1C[C@@]2([H])N(C(=O)CS(C)(=O)=O)C[C@]1([H])C2 WBWMNHCLCKMTQT-CMKODMSKSA-N 0.000 claims 1
- NWORNPKFWKWJNQ-CMKODMSKSA-N 1-[(1s,4s)-5-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-2,5-diazabicyclo[2.2.2]octan-2-yl]-2-hydroxyethanone Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1C[C@]2([H])CC[C@@]1([H])CN2C(=O)CO NWORNPKFWKWJNQ-CMKODMSKSA-N 0.000 claims 1
- DMNPPAKBNLHVTJ-IRFCIJBXSA-N 1-[(1s,4s)-5-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-2,5-diazabicyclo[2.2.2]octan-2-yl]ethanone Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1C[C@]2([H])CC[C@@]1([H])CN2C(C)=O DMNPPAKBNLHVTJ-IRFCIJBXSA-N 0.000 claims 1
- VXMBWJLKIBRQQM-GZNCHQMQSA-N 1-[2-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl]ethanone Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1CC2CN(C(=O)C)CC2C1 VXMBWJLKIBRQQM-GZNCHQMQSA-N 0.000 claims 1
- ZLQVMSPZAPIQTE-HXUWFJFHSA-N 1-[4-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-1,4-diazepan-1-yl]-2-methoxyethanone Chemical compound C1CN(C(=O)COC)CCCN1CC1=CC=C([C@@H]2OC3=NC=CC=C3OC2)C=C1 ZLQVMSPZAPIQTE-HXUWFJFHSA-N 0.000 claims 1
- QVKSDOXESFLWPP-GOSISDBHSA-N 1-[4-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]piperazin-1-yl]-2-hydroxyethanone Chemical compound C1CN(C(=O)CO)CCN1CC1=CC=C([C@@H]2OC3=NC=CC=C3OC2)C=C1 QVKSDOXESFLWPP-GOSISDBHSA-N 0.000 claims 1
- NHCPIYYGGBTGSA-GZNCHQMQSA-N 1-[8-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-3,8-diazabicyclo[3.2.1]octan-3-yl]ethanone Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1C2CCC1CN(C(=O)C)C2 NHCPIYYGGBTGSA-GZNCHQMQSA-N 0.000 claims 1
- SAYRKNGOIDYMPE-BDPMCISCSA-N 1-[[4-[(3s)-2,3-dihydro-1,4-benzodioxin-3-yl]phenyl]methyl]azepane-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCCN1CC1=CC=C([C@@H]2OC3=CC=CC=C3OC2)C=C1 SAYRKNGOIDYMPE-BDPMCISCSA-N 0.000 claims 1
- GQHIUGOGODYQFZ-GOSISDBHSA-N 1-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-4-methylpiperidin-4-ol Chemical compound C1CC(C)(O)CCN1CC1=CC=C([C@@H]2OC3=NC=CC=C3OC2)C=C1 GQHIUGOGODYQFZ-GOSISDBHSA-N 0.000 claims 1
- UVMJYVNJUCRSAK-HSZRJFAPSA-N 1-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-4-phenylpiperidin-4-ol Chemical compound C1CN(CC=2C=CC(=CC=2)[C@@H]2OC3=NC=CC=C3OC2)CCC1(O)C1=CC=CC=C1 UVMJYVNJUCRSAK-HSZRJFAPSA-N 0.000 claims 1
- DALGSKBFCKEXRR-HSZRJFAPSA-N 1-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-4-phenylpiperidine-4-carboxylic acid Chemical compound C1CN(CC=2C=CC(=CC=2)[C@@H]2OC3=NC=CC=C3OC2)CCC1(C(=O)O)C1=CC=CC=C1 DALGSKBFCKEXRR-HSZRJFAPSA-N 0.000 claims 1
- BMARJSPDNJUQAS-OAQYLSRUSA-N 1-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-n-(2-hydroxy-2-methylpropyl)piperidine-4-carboxamide Chemical compound C1CC(C(=O)NCC(C)(O)C)CCN1CC1=CC=C([C@@H]2OC3=NC=CC=C3OC2)C=C1 BMARJSPDNJUQAS-OAQYLSRUSA-N 0.000 claims 1
- UAKJHRSRXWOQSZ-JTHBVZDNSA-N 1-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-n-[[(2s)-oxolan-2-yl]methyl]piperidine-4-carboxamide Chemical compound C1CN(CC=2C=CC(=CC=2)[C@@H]2OC3=NC=CC=C3OC2)CCC1C(=O)NC[C@@H]1CCCO1 UAKJHRSRXWOQSZ-JTHBVZDNSA-N 0.000 claims 1
- FUGAPBQLFBIWNS-HXUWFJFHSA-N 2-[1-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]piperidin-4-yl]-n-methoxyacetamide Chemical compound C1CC(CC(=O)NOC)CCN1CC1=CC=C([C@@H]2OC3=NC=CC=C3OC2)C=C1 FUGAPBQLFBIWNS-HXUWFJFHSA-N 0.000 claims 1
- FSOZARQIIRDYRC-LJQANCHMSA-N 2-[4-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]piperazin-1-yl]acetonitrile Chemical compound C1CN(CC#N)CCN1CC1=CC=C([C@@H]2OC3=NC=CC=C3OC2)C=C1 FSOZARQIIRDYRC-LJQANCHMSA-N 0.000 claims 1
- UZQMLYLLVGFIJW-FAFZWHIHSA-N 2-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxamide Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1CC2CN(C(=O)N)CC2C1 UZQMLYLLVGFIJW-FAFZWHIHSA-N 0.000 claims 1
- LAQJGAKLLZAETL-UHFFFAOYSA-N 2h-pyrazin-3-one Chemical compound O=C1CN=CC=N1 LAQJGAKLLZAETL-UHFFFAOYSA-N 0.000 claims 1
- QSIHJHOYBKRZOI-OAQYLSRUSA-N 3-[1-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]piperidin-4-yl]-1,3-oxazinan-2-one Chemical compound O=C1OCCCN1C1CCN(CC=2C=CC(=CC=2)[C@@H]2OC3=NC=CC=C3OC2)CC1 QSIHJHOYBKRZOI-OAQYLSRUSA-N 0.000 claims 1
- BABCCVNFXNKFCS-AREMUKBSSA-N 3-[[4-[[4-[(3s)-2,3-dihydro-1,4-benzodioxin-3-yl]phenyl]methyl]piperazin-1-yl]methyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(CN2CCN(CC=3C=CC(=CC=3)[C@@H]3OC4=CC=CC=C4OC3)CC2)=C1 BABCCVNFXNKFCS-AREMUKBSSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- FFHKJCLEIPHMMO-XMMPIXPASA-N 4-[1-[[4-[(3s)-2,3-dihydro-1,4-benzodioxin-3-yl]phenyl]methyl]azetidin-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1CN(CC=2C=CC(=CC=2)[C@@H]2OC3=CC=CC=C3OC2)C1 FFHKJCLEIPHMMO-XMMPIXPASA-N 0.000 claims 1
- WNTONAWVMATBNR-MXJXRJBTSA-N 4-[1-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]piperidin-4-yl]cyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1C1CCN(CC=2C=CC(=CC=2)[C@@H]2OC3=NC=CC=C3OC2)CC1 WNTONAWVMATBNR-MXJXRJBTSA-N 0.000 claims 1
- AYBQTOQZCSLBPB-GOSISDBHSA-N 4-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-1,4-thiazepane 1,1-dioxide Chemical compound C1CS(=O)(=O)CCCN1CC1=CC=C([C@@H]2OC3=NC=CC=C3OC2)C=C1 AYBQTOQZCSLBPB-GOSISDBHSA-N 0.000 claims 1
- MOCNGUIQBKJBPS-QGZVFWFLSA-N 4-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-1,4-thiazinane 1-oxide Chemical compound C1CS(=O)CCN1CC1=CC=C([C@@H]2OC3=NC=CC=C3OC2)C=C1 MOCNGUIQBKJBPS-QGZVFWFLSA-N 0.000 claims 1
- LWHVXBXYQMQDNU-QGZVFWFLSA-N 5-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-amine Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1CCC(N=C(S2)N)=C2C1 LWHVXBXYQMQDNU-QGZVFWFLSA-N 0.000 claims 1
- HXLHEHNXQXOMML-QGZVFWFLSA-N 7-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-5,6,8,9-tetrahydro-[1,2,4]triazolo[4,3-d][1,4]diazepine-3-carboxamide Chemical compound C1CN2C(C(=O)N)=NN=C2CCN1CC1=CC=C([C@@H]2OC3=NC=CC=C3OC2)C=C1 HXLHEHNXQXOMML-QGZVFWFLSA-N 0.000 claims 1
- VRSIRTPCSWRLHZ-MRXNPFEDSA-N 7-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazine-3-carboxamide Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1CC2=NN=C(C(=O)N)N2CC1 VRSIRTPCSWRLHZ-MRXNPFEDSA-N 0.000 claims 1
- GNZUXNGMJPKNGV-GOSISDBHSA-N 7-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-6,8-dihydro-5h-imidazo[1,2-a]pyrazine-2-carboxamide Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1CCN2C=C(C(=O)N)N=C2C1 GNZUXNGMJPKNGV-GOSISDBHSA-N 0.000 claims 1
- UJZWBKMWQIXKLB-LJQANCHMSA-N 7-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-6,8-dihydro-5h-imidazo[1,2-a]pyrazine-3-carbonitrile Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1CC2=NC=C(C#N)N2CC1 UJZWBKMWQIXKLB-LJQANCHMSA-N 0.000 claims 1
- BXJSBKDOGBJKJG-GOSISDBHSA-N 7-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-n-methyl-5,6,8,9-tetrahydro-[1,2,4]triazolo[4,3-d][1,4]diazepine-3-carboxamide Chemical compound C1CN2C(C(=O)NC)=NN=C2CCN1CC1=CC=C([C@@H]2OC3=NC=CC=C3OC2)C=C1 BXJSBKDOGBJKJG-GOSISDBHSA-N 0.000 claims 1
- RGXOOENRUSDMNA-QGZVFWFLSA-N 7-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-n-methyl-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazine-3-carboxamide Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1CC2=NN=C(C(=O)NC)N2CC1 RGXOOENRUSDMNA-QGZVFWFLSA-N 0.000 claims 1
- NYZYOWPAUGIHSD-LJQANCHMSA-N 7-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-n-methyl-6,8-dihydro-5h-imidazo[1,2-a]pyrazine-2-carboxamide Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1CCN2C=C(C(=O)NC)N=C2C1 NYZYOWPAUGIHSD-LJQANCHMSA-N 0.000 claims 1
- BGBPXFGLLJYDKK-LQXLOVGSSA-N C1OC2=CC=CC=C2O[C@H]1C(C=C1)=CC=C1CN1C[C@@H]2C(C(=O)O)[C@@H]2C1 Chemical compound C1OC2=CC=CC=C2O[C@H]1C(C=C1)=CC=C1CN1C[C@@H]2C(C(=O)O)[C@@H]2C1 BGBPXFGLLJYDKK-LQXLOVGSSA-N 0.000 claims 1
- RESWFBUPGRRWGR-XSONFBQWSA-N C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1C[C@@H]2C(C(=O)NCC(C)(O)C)[C@@H]2C1 Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1C[C@@H]2C(C(=O)NCC(C)(O)C)[C@@H]2C1 RESWFBUPGRRWGR-XSONFBQWSA-N 0.000 claims 1
- NMGMYBVVXDVBGF-SVCRJVSBSA-N C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1C[C@@H]2C(C(=O)NC[C@@H](O)C)[C@@H]2C1 Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1C[C@@H]2C(C(=O)NC[C@@H](O)C)[C@@H]2C1 NMGMYBVVXDVBGF-SVCRJVSBSA-N 0.000 claims 1
- MZDRGWKDJASOTN-SVCRJVSBSA-N C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1C[C@@H]2C(C(=O)N[C@H](CO)C)[C@@H]2C1 Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1C[C@@H]2C(C(=O)N[C@H](CO)C)[C@@H]2C1 MZDRGWKDJASOTN-SVCRJVSBSA-N 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- CESDVPRPLGVAFS-OAQYLSRUSA-N [1-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]piperidin-4-yl]-(3-hydroxyazetidin-1-yl)methanone Chemical compound C1C(O)CN1C(=O)C1CCN(CC=2C=CC(=CC=2)[C@@H]2OC3=NC=CC=C3OC2)CC1 CESDVPRPLGVAFS-OAQYLSRUSA-N 0.000 claims 1
- RQBKDVOEXKXVPO-LJQANCHMSA-N [1-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]piperidin-4-yl]methylurea Chemical compound C1CC(CNC(=O)N)CCN1CC1=CC=C([C@@H]2OC3=NC=CC=C3OC2)C=C1 RQBKDVOEXKXVPO-LJQANCHMSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- CMACMMKTCMLGOJ-GOSISDBHSA-N ethyl 7-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazine-3-carboxylate Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1CC2=NN=C(C(=O)OCC)N2CC1 CMACMMKTCMLGOJ-GOSISDBHSA-N 0.000 claims 1
- ORENEKQWPYJXFE-RKKYOWQMSA-N n-[(1s,5r)-8-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-8-azabicyclo[3.2.1]octan-3-yl]acetamide Chemical compound C1OC2=CC=CN=C2O[C@H]1C(C=C1)=CC=C1CN1[C@@H]2CC[C@H]1CC(NC(=O)C)C2 ORENEKQWPYJXFE-RKKYOWQMSA-N 0.000 claims 1
- PPMIBQXMIKYLRC-JOCHJYFZSA-N n-[1-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]piperidin-4-yl]-2-(2-oxopyrrolidin-1-yl)acetamide Chemical compound C1CN(CC=2C=CC(=CC=2)[C@@H]2OC3=NC=CC=C3OC2)CCC1NC(=O)CN1CCCC1=O PPMIBQXMIKYLRC-JOCHJYFZSA-N 0.000 claims 1
- RGPLVNUFBYNFSX-HXUWFJFHSA-N n-[1-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]piperidin-4-yl]-2-methoxyacetamide Chemical compound C1CC(NC(=O)COC)CCN1CC1=CC=C([C@@H]2OC3=NC=CC=C3OC2)C=C1 RGPLVNUFBYNFSX-HXUWFJFHSA-N 0.000 claims 1
- WOZNAVQSTYHBNO-HSZRJFAPSA-N n-[1-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]piperidin-4-yl]oxane-4-carboxamide Chemical compound C1CN(CC=2C=CC(=CC=2)[C@@H]2OC3=NC=CC=C3OC2)CCC1NC(=O)C1CCOCC1 WOZNAVQSTYHBNO-HSZRJFAPSA-N 0.000 claims 1
- OSQLJPYGCWCRRJ-OAQYLSRUSA-N n-[3-[4-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]piperazin-1-yl]-3-oxopropyl]acetamide Chemical compound C1CN(C(=O)CCNC(=O)C)CCN1CC1=CC=C([C@@H]2OC3=NC=CC=C3OC2)C=C1 OSQLJPYGCWCRRJ-OAQYLSRUSA-N 0.000 claims 1
- SQWIFYZYCUJHMB-OAQYLSRUSA-N n-[[1-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]piperidin-4-yl]methyl]-2-hydroxy-2-methylpropanamide Chemical compound C1CC(CNC(=O)C(C)(O)C)CCN1CC1=CC=C([C@@H]2OC3=NC=CC=C3OC2)C=C1 SQWIFYZYCUJHMB-OAQYLSRUSA-N 0.000 claims 1
- ZMKACHWUBOWAKP-OAQYLSRUSA-N n-[[1-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]piperidin-4-yl]methyl]acetamide Chemical compound C1CC(CNC(=O)C)CCN1CC1=CC=C([C@@H]2OC3=NC=CC=C3OC2)C=C1 ZMKACHWUBOWAKP-OAQYLSRUSA-N 0.000 claims 1
- VKLGZVWDVSLOLN-UHUGOGIASA-N n-[[4-[(3s)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]phenyl]methyl]-n-methyl-1,1-dioxothiolan-3-amine Chemical compound C=1C=C([C@@H]2OC3=NC=CC=C3OC2)C=CC=1CN(C)C1CCS(=O)(=O)C1 VKLGZVWDVSLOLN-UHUGOGIASA-N 0.000 claims 1
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| US8551982B2 (en) | 2011-03-14 | 2013-10-08 | Boehringer Ingelheim International Gmbh | Benzodioxane inhibitors of leukotriene production |
| EP2734516B1 (en) | 2011-07-19 | 2015-06-17 | Boehringer Ingelheim International GmbH | Arylpyrazole ethers as inhibitors of leukotriene a4 hydrolase |
| EP2822942B1 (en) | 2012-03-06 | 2017-05-10 | Boehringer Ingelheim International GmbH | Benzodioxanes for inhibiting leukotriene production |
| JP6080226B2 (ja) | 2012-03-06 | 2017-02-15 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 他の活性物質と組み合わせたロイコトリエン産生阻害用ベンゾジオキサン |
| EP2885285B1 (en) | 2012-07-17 | 2016-10-19 | Boehringer Ingelheim International GmbH | Pyrazole drivatives which inhibit leukotriene production |
| JP6353899B2 (ja) | 2013-07-15 | 2018-07-04 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ロイコトリエン生成の阻害剤 |
| US9573957B2 (en) | 2013-07-15 | 2017-02-21 | Boehringer Ingelheim International Gmbh | Inhibitors of leukotriene production |
| CN104974106B (zh) * | 2014-04-04 | 2019-02-22 | 浙江普洛康裕制药有限公司 | 5-烷基-[1,3,4]-噁二唑-2-甲酸烷基酯的合成方法 |
| CN105440041A (zh) * | 2015-12-30 | 2016-03-30 | 上海药明康德新药开发有限公司 | 7-叔丁基-2-乙基-8-甲基-5,6-二氢咪唑[1,2-a]吡嗪-2,7（8H）-二羧酸的合成方法 |
| CN109111447A (zh) | 2017-06-23 | 2019-01-01 | 中国科学院上海药物研究所 | 7-位取代吡咯并三嗪类化合物或其药学上可用的盐，及其制备方法和用途 |
| TWI841671B (zh) | 2019-01-24 | 2024-05-11 | 日商第一三共股份有限公司 | 具有取代基之脲化合物 |
| KR20230051227A (ko) | 2020-08-14 | 2023-04-17 | 노파르티스 아게 | 헤테로아릴 치환된 스피로피페리디닐 유도체 및 이의 제약 용도 |
| US11932630B2 (en) | 2021-04-16 | 2024-03-19 | Novartis Ag | Heteroaryl aminopropanol derivatives |
| AU2022376563A1 (en) | 2021-11-01 | 2023-12-07 | Alkahest, Inc. | Benzodioxane modulators of leukotriene a4 hydrolase (lta4h) for prevention and treatment of aging-associated diseases |
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| US4918092A (en) * | 1983-12-21 | 1990-04-17 | Merck Frosst Canada, Inc. | Leukotriene antagonists |
| US5120758A (en) | 1991-02-08 | 1992-06-09 | Ciba-Geigy Corporation | Certain benzodioxole, benzodioxane and benzodioxepin derivatives useful as 5-lipoxygenase inhibitors |
| DE19821003A1 (de) | 1998-05-11 | 1999-11-18 | Dresden Arzneimittel | Neue 1,2,5-trisubstituierte 1,2-dihydro-indazol-3-one mit antiasthmatischer, antiallergischer, entzündungshemmender, immunmodulierender und neuroprotektiver Wirkung, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| PL362919A1 (en) | 2000-10-26 | 2004-11-02 | Pfizer Products Inc. | Pyrimidine-2,4,6-trione metalloproteinase inhibitors |
| US7098222B2 (en) | 2004-05-12 | 2006-08-29 | Abbott Laboratories | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
| BRPI0518508A2 (pt) | 2005-01-07 | 2008-11-25 | Pfizer Prod Inc | compostos de quinolina heteroaromÁticos e seu uso como inibidores de pde10 |
| KR20080003385A (ko) | 2005-03-31 | 2008-01-07 | 얀센 파마슈티카 엔.브이. | 페닐 및 피리딜 ｌｔａ４ｈ 조절제 |
| JP5133889B2 (ja) | 2005-09-21 | 2013-01-30 | デコード ジェネティクス イーエイチエフ | 炎症治療のためのビアリール基置換複素環ｌｔａ４ｈ阻害剤 |
| AU2006327243A1 (en) | 2005-12-21 | 2007-06-28 | Decode Genetics Ehf | N-linked aryl heteroaryl inhibitors of LTA4H for treating inflammation |
| RS52712B (sr) * | 2008-04-11 | 2013-08-30 | Janssen Pharmaceutica N.V. | Tiazolopiridin-2-iloksi-fenil i tiazolopirazin-2-iloksi-fenil amini kao modulatori leukotrien a4 hidrolaze |
| CN102946877B (zh) | 2010-03-18 | 2019-07-05 | 香港科技大学 | 乳突果及其分离的化合物在制备用于治疗神经疾病的药物中的用途 |
| US8551982B2 (en) * | 2011-03-14 | 2013-10-08 | Boehringer Ingelheim International Gmbh | Benzodioxane inhibitors of leukotriene production |
| EP2734516B1 (en) | 2011-07-19 | 2015-06-17 | Boehringer Ingelheim International GmbH | Arylpyrazole ethers as inhibitors of leukotriene a4 hydrolase |
| EP2822942B1 (en) | 2012-03-06 | 2017-05-10 | Boehringer Ingelheim International GmbH | Benzodioxanes for inhibiting leukotriene production |
| JP6080226B2 (ja) | 2012-03-06 | 2017-02-15 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 他の活性物質と組み合わせたロイコトリエン産生阻害用ベンゾジオキサン |
| EP2885285B1 (en) | 2012-07-17 | 2016-10-19 | Boehringer Ingelheim International GmbH | Pyrazole drivatives which inhibit leukotriene production |
-
2013
- 2013-03-05 EP EP13712002.8A patent/EP2822942B1/en active Active
- 2013-03-05 WO PCT/US2013/029054 patent/WO2013134226A1/en not_active Ceased
- 2013-03-05 US US13/785,034 patent/US8946203B2/en active Active
- 2013-03-05 AR ARP130100728 patent/AR091315A1/es unknown
- 2013-03-05 JP JP2014561023A patent/JP6080227B2/ja active Active
- 2013-03-05 TW TW102107704A patent/TW201350474A/zh unknown
- 2013-03-06 UY UY0001034660A patent/UY34660A/es unknown
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