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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| CA2835617C (en) | 2011-03-14 | 2020-07-21 | 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 |
| NZ628587A (en) | 2012-03-06 | 2016-07-29 | Boehringer Ingelheim Int | Benzodioxanes in combination with other actives for inhibiting leukotriene production |
| TW201350474A (zh) | 2012-03-06 | 2013-12-16 | Boehringer Ingelheim Int | 白三烯素生成之苯并二噁烷抑制劑 |
| US9403830B2 (en) | 2012-07-17 | 2016-08-02 | Boehringer Ingelheim International Gmbh | Inhibitors of leukotriene production |
| JP2016523982A (ja) | 2013-07-15 | 2016-08-12 | 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 |
| 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 |
| 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 |
| MX2023001725A (es) | 2020-08-14 | 2023-02-22 | Novartis Ag | Derivados de espiropiperidinilo sustituidos con heteroarilo y usos farmaceuticos de los mismos. |
| 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 |
| HUP0302337A3 (en) | 2000-10-26 | 2004-01-28 | Pfizer Prod Inc | Pyrimidine-2,4,6-trione metalloproteinase inhibitors, pharmaceutical compositions containing them and their use |
| US7098222B2 (en) | 2004-05-12 | 2006-08-29 | Abbott Laboratories | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
| UA86283C2 (uk) | 2005-01-07 | 2009-04-10 | Пфайзер Продактс Инк. | Гетероароматичні сполуки хіноліну і їх застосування як інгібіторів pde10 |
| US20060223792A1 (en) | 2005-03-31 | 2006-10-05 | Butler Christopher R | Phenyl and pyridyl LTA4H modulators |
| US20070078263A1 (en) | 2005-09-21 | 2007-04-05 | Decode Chemistry, Inc. | Biaryl substituted 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 |
| 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 |
| GB2494787B (en) | 2010-03-18 | 2018-10-17 | Univ Hong Kong Sci & Tech | Neuro-protective effects of adelostemma gracillimum and its isolated compounds |
| CA2835617C (en) * | 2011-03-14 | 2020-07-21 | 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 |
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| NZ628587A (en) * | 2012-03-06 | 2016-07-29 | Boehringer Ingelheim Int | Benzodioxanes in combination with other actives for inhibiting leukotriene production |
| US9403830B2 (en) | 2012-07-17 | 2016-08-02 | Boehringer Ingelheim International Gmbh | Inhibitors of leukotriene production |
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- 2013-03-05 WO PCT/US2013/029054 patent/WO2013134226A1/en not_active Ceased
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- 2013-03-05 AR ARP130100728 patent/AR091315A1/es unknown
- 2013-03-06 UY UY0001034660A patent/UY34660A/es unknown