JP2018512381A5 - - Google Patents
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- Publication number
- JP2018512381A5 JP2018512381A5 JP2017543746A JP2017543746A JP2018512381A5 JP 2018512381 A5 JP2018512381 A5 JP 2018512381A5 JP 2017543746 A JP2017543746 A JP 2017543746A JP 2017543746 A JP2017543746 A JP 2017543746A JP 2018512381 A5 JP2018512381 A5 JP 2018512381A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- trifluoromethyl
- aminomethyl
- oxy
- substituted
- 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 pyrrolidinonyl Chemical group 0.000 claims 29
- 150000003839 salts Chemical class 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 13
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 9
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 5
- 125000006747 (C2-C10) heterocycloalkyl group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 125000004434 sulfur atom Chemical group 0.000 claims 4
- HDACDDSPBQTVCH-UHFFFAOYSA-N 3-hydroxypyrrolidine-1-carbaldehyde Chemical compound OC1CCN(C=O)C1 HDACDDSPBQTVCH-UHFFFAOYSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 3
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- AJPGSXUUJRFUFX-UHFFFAOYSA-N 3-fluoropyrrolidine-1-carbaldehyde Chemical compound FC1CCN(C=O)C1 AJPGSXUUJRFUFX-UHFFFAOYSA-N 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 229910052805 deuterium Inorganic materials 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 2
- VJLYHTOSFSGXGH-CQSZACIVSA-N (2R)-1-[3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxybenzoyl]pyrrolidine-2-carboxylic acid Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)N2[C@H](CCC2)C(=O)O)C=CC=1 VJLYHTOSFSGXGH-CQSZACIVSA-N 0.000 claims 1
- VJLYHTOSFSGXGH-AWEZNQCLSA-N (2S)-1-[3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxybenzoyl]pyrrolidine-2-carboxylic acid Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)N2[C@@H](CCC2)C(=O)O)C=CC=1 VJLYHTOSFSGXGH-AWEZNQCLSA-N 0.000 claims 1
- NPNATZWDBSJWKE-OAHLLOKOSA-N (3R)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylpiperidine-1-carboxamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@H]1CN(CCC1)C(=O)NC1=CC=CC=C1 NPNATZWDBSJWKE-OAHLLOKOSA-N 0.000 claims 1
- KVEDLFCMPYPWSC-ZDUSSCGKSA-N (3R)-3-[[3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxybenzoyl]amino]pent-4-ynoic acid Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)N[C@H](CC(=O)O)C#C)C=CC=1 KVEDLFCMPYPWSC-ZDUSSCGKSA-N 0.000 claims 1
- NPNATZWDBSJWKE-HNNXBMFYSA-N (3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylpiperidine-1-carboxamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(=O)NC1=CC=CC=C1 NPNATZWDBSJWKE-HNNXBMFYSA-N 0.000 claims 1
- KVEDLFCMPYPWSC-CYBMUJFWSA-N (3S)-3-[[3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxybenzoyl]amino]pent-4-ynoic acid Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)N[C@@H](CC(=O)O)C#C)C=CC=1 KVEDLFCMPYPWSC-CYBMUJFWSA-N 0.000 claims 1
- SNAKUPLQASYKTC-AWEZNQCLSA-N (3S)-3-[[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxymethyl]-N-phenylpiperidine-1-carboxamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC[C@@H]1CN(CCC1)C(=O)NC1=CC=CC=C1 SNAKUPLQASYKTC-AWEZNQCLSA-N 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 1
- RAVIQFQJZMTUBX-AWEZNQCLSA-N 1-[(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidin-1-yl]-2-(3,4-dichlorophenyl)ethanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(CC1=CC(=C(C=C1)Cl)Cl)=O RAVIQFQJZMTUBX-AWEZNQCLSA-N 0.000 claims 1
- XAOMFUPJQYNDEG-LBPRGKRZSA-N 1-[(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidin-1-yl]-2-methylpropan-1-one Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(C(C)C)=O XAOMFUPJQYNDEG-LBPRGKRZSA-N 0.000 claims 1
- UCKHFQJIKQLJRT-INIZCTEOSA-N 1-[(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidin-1-yl]-2-phenylethanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(CC1=CC=CC=C1)=O UCKHFQJIKQLJRT-INIZCTEOSA-N 0.000 claims 1
- ZXERRERAZGCVDW-UHFFFAOYSA-N 1-[2-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-6-azaspiro[3.4]octan-6-yl]ethanone Chemical compound CC(=O)N1CCC2(CC(C2)OC2=NC(=CC(CN)=C2)C(F)(F)F)C1 ZXERRERAZGCVDW-UHFFFAOYSA-N 0.000 claims 1
- LMCOZBHJIOVSPA-UHFFFAOYSA-N 1-[3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxybenzoyl]azetidine-3-carbonitrile Chemical compound NCC1=CC(OC2=CC=CC(=C2)C(=O)N2CC(C2)C#N)=NC(=C1)C(F)(F)F LMCOZBHJIOVSPA-UHFFFAOYSA-N 0.000 claims 1
- JZSHKZABPPZQLV-UHFFFAOYSA-N 1-[3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]pyridin-2-one Chemical compound NCC1=CC(OC2=CC=CC(=C2)N2C=CC=CC2=O)=NC(=C1)C(F)(F)F JZSHKZABPPZQLV-UHFFFAOYSA-N 0.000 claims 1
- NBRQAMAPCCHUOA-UHFFFAOYSA-N 1-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]-3-N-phenylcyclohexa-3,5-diene-1,3-dicarboxamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)C1(C(=O)N)CC(C(=O)NC2=CC=CC=C2)=CC=C1 NBRQAMAPCCHUOA-UHFFFAOYSA-N 0.000 claims 1
- KHKQQQLOLBEJES-UHFFFAOYSA-N 1-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]pyridin-2-one Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)N1C(C=CC=C1)=O KHKQQQLOLBEJES-UHFFFAOYSA-N 0.000 claims 1
- DCGQVDFBDSTUML-AWEZNQCLSA-N 2-[(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidine-1-carbonyl]chromen-4-one Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(=O)C=1OC2=CC=CC=C2C(C=1)=O DCGQVDFBDSTUML-AWEZNQCLSA-N 0.000 claims 1
- DDGXRJAUXIYLKP-UHFFFAOYSA-N 2-[4-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyindol-1-yl]-1-piperazin-1-ylethanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC1=C2C=CN(C2=CC=C1)CC(=O)N1CCNCC1 DDGXRJAUXIYLKP-UHFFFAOYSA-N 0.000 claims 1
- XJZJSAGRNWQXBB-UHFFFAOYSA-N 2-[4-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyindol-1-yl]-1-piperidin-1-ylethanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC1=C2C=CN(C2=CC=C1)CC(=O)N1CCCCC1 XJZJSAGRNWQXBB-UHFFFAOYSA-N 0.000 claims 1
- RICYMNABWTZUIH-UHFFFAOYSA-N 2-[4-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyindol-1-yl]-N-(diaminomethylidene)acetamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC1=C2C=CN(C2=CC=C1)CC(=O)NC(N)=N RICYMNABWTZUIH-UHFFFAOYSA-N 0.000 claims 1
- BVKRPQCDGACLPX-UHFFFAOYSA-N 2-[4-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyindol-1-yl]-N-methyl-N-phenylacetamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC1=C2C=CN(C2=CC=C1)CC(=O)N(C1=CC=CC=C1)C BVKRPQCDGACLPX-UHFFFAOYSA-N 0.000 claims 1
- YLMMGIJJUJKKDJ-UHFFFAOYSA-N 2-[5-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-2-oxo-3,4-dihydroquinolin-1-yl]butanoic acid Chemical class CCC(C(=O)O)N1C(=O)CCC2=C1C=CC=C2OC3=CC(=CC(=N3)C(F)(F)F)CN YLMMGIJJUJKKDJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- ZEMNVPLWDUWKEG-UHFFFAOYSA-N 3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound C1=CC=C2CN(C=O)CCC2=C1 ZEMNVPLWDUWKEG-UHFFFAOYSA-N 0.000 claims 1
- DSPQGWPQLXUQEA-UHFFFAOYSA-N 3-(hydroxymethyl)piperidine-1-carbaldehyde Chemical compound OCC1CCCN(C=O)C1 DSPQGWPQLXUQEA-UHFFFAOYSA-N 0.000 claims 1
- SRSUPLJBRKDZES-UHFFFAOYSA-N 3-(hydroxymethyl)pyrrolidine-1-carbaldehyde Chemical compound OCC1CCN(C=O)C1 SRSUPLJBRKDZES-UHFFFAOYSA-N 0.000 claims 1
- DIGKDXSIFKBDRY-UHFFFAOYSA-N 3-N-(2-methylsulfonylethyl)benzene-1,3-dicarboxamide Chemical compound C(C1=CC(C(=O)N)=CC=C1)(=O)NCCS(=O)(=O)C DIGKDXSIFKBDRY-UHFFFAOYSA-N 0.000 claims 1
- WSNKEJIFARPOSQ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(1-benzothiophen-2-ylmethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC3=C(S2)C=CC=C3)C=CC=1 WSNKEJIFARPOSQ-UHFFFAOYSA-N 0.000 claims 1
- LWQPNBSCXAHNRY-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2-hydroxyethyl)-N-methylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)N(C)CCO)C=CC=1 LWQPNBSCXAHNRY-UHFFFAOYSA-N 0.000 claims 1
- HFEMNNNOZWVSIN-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(4-ethylphenyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=C(C=C2)CC)C=CC=1 HFEMNNNOZWVSIN-UHFFFAOYSA-N 0.000 claims 1
- GDSLUYKCPYECNN-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[(4-fluorophenyl)methyl]benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC=C(C=C2)F)C=CC=1 GDSLUYKCPYECNN-UHFFFAOYSA-N 0.000 claims 1
- LLOOIRAXTRVTJW-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-hydroxybenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NO)C=CC=1 LLOOIRAXTRVTJW-UHFFFAOYSA-N 0.000 claims 1
- SSLNFPXCHICZFK-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-methoxybenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NOC)C=CC=1 SSLNFPXCHICZFK-UHFFFAOYSA-N 0.000 claims 1
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 claims 1
- QKFBUXQHHOFRDX-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxybenzoic acid Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)O)C=CC=1 QKFBUXQHHOFRDX-UHFFFAOYSA-N 0.000 claims 1
- VVPGEFWZAXBZHR-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]sulfanyl-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)SC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 VVPGEFWZAXBZHR-UHFFFAOYSA-N 0.000 claims 1
- HAEQAUJYNHQVHV-XUWBISKJSA-N 3-[4-[amino(dideuterio)methyl]-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NC(C1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1)([2H])[2H] HAEQAUJYNHQVHV-XUWBISKJSA-N 0.000 claims 1
- RXGLCKYVLQCQOE-UHFFFAOYSA-N 3-[[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]carbamoyl]benzoic acid Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)NC(=O)C=1C=C(C(=O)O)C=CC=1 RXGLCKYVLQCQOE-UHFFFAOYSA-N 0.000 claims 1
- VONPPEBXQFZBNY-UHFFFAOYSA-N 3-[[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]methyl]-1-(2-hydroxyethyl)-6-methylpyrimidine-2,4-dione Chemical compound CC1=CC(=O)N(CC2=NC(=CC(CN)=C2)C(F)(F)F)C(=O)N1CCO VONPPEBXQFZBNY-UHFFFAOYSA-N 0.000 claims 1
- CXYQWBDIFFPVDM-UHFFFAOYSA-N 3-[[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]methyl]-1-benzyl-6-methylpyrimidine-2,4-dione Chemical compound CC1=CC(=O)N(CC2=NC(=CC(CN)=C2)C(F)(F)F)C(=O)N1CC1=CC=CC=C1 CXYQWBDIFFPVDM-UHFFFAOYSA-N 0.000 claims 1
- FFGBQXVBPPXVJP-UHFFFAOYSA-N 3-[[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]methyl]-6-methyl-1-(pyrimidin-4-ylmethyl)pyrimidine-2,4-dione Chemical compound CC1=CC(=O)N(CC2=NC(=CC(CN)=C2)C(F)(F)F)C(=O)N1CC1=CC=NC=N1 FFGBQXVBPPXVJP-UHFFFAOYSA-N 0.000 claims 1
- XXAFCSLVTWGVEY-UHFFFAOYSA-N 3-[[[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]amino]methyl]-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)NCC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 XXAFCSLVTWGVEY-UHFFFAOYSA-N 0.000 claims 1
- QAGMTXXQOKVNQY-UHFFFAOYSA-N 3-aminopyrrolidine-1-carbaldehyde Chemical compound NC1CCN(C=O)C1 QAGMTXXQOKVNQY-UHFFFAOYSA-N 0.000 claims 1
- WWGCKRAFNGJJGY-UHFFFAOYSA-N 3-fluoro-4-hydroxypyrrolidine-1-carbaldehyde Chemical compound FC1CN(CC1O)C=O WWGCKRAFNGJJGY-UHFFFAOYSA-N 0.000 claims 1
- QEIVWSRXBYOTAZ-UHFFFAOYSA-N 4-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylpiperidine-1-carboxamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC1CCN(CC1)C(=O)NC1=CC=CC=C1 QEIVWSRXBYOTAZ-UHFFFAOYSA-N 0.000 claims 1
- AYAFGADFIINPRZ-UHFFFAOYSA-N 4-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylpyridine-2-carboxamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC1=CC(=NC=C1)C(=O)NC1=CC=CC=C1 AYAFGADFIINPRZ-UHFFFAOYSA-N 0.000 claims 1
- HOWFLZVASJDZRZ-UHFFFAOYSA-N 4-[[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxymethyl]-N-phenylpiperidine-1-carboxamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OCC1CCN(CC1)C(=O)NC1=CC=CC=C1 HOWFLZVASJDZRZ-UHFFFAOYSA-N 0.000 claims 1
- IAELUAQCRQBCOU-UHFFFAOYSA-N 5-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-1-(2-hydroxyethyl)-3,4-dihydroquinolin-2-one Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC1=C2CCC(N(C2=CC=C1)CCO)=O IAELUAQCRQBCOU-UHFFFAOYSA-N 0.000 claims 1
- FOFSNCRMWLKAIM-UHFFFAOYSA-N 5-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-3,4-dihydro-1H-quinolin-2-one Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC1=C2CCC(NC2=CC=C1)=O FOFSNCRMWLKAIM-UHFFFAOYSA-N 0.000 claims 1
- NRLQBVLOUUPAMI-UHFFFAOYSA-N 8-[3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxybenzoyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)N2CCC3(CNC(O3)=O)CC2)C=CC=1 NRLQBVLOUUPAMI-UHFFFAOYSA-N 0.000 claims 1
- MWQLXWNMMZGQMY-LBPRGKRZSA-N C1=CC=C(C=C1)N[C@@H](COC2=CC(=CC(=N2)C(F)(F)F)CN)C(=O)O Chemical compound C1=CC=C(C=C1)N[C@@H](COC2=CC(=CC(=N2)C(F)(F)F)CN)C(=O)O MWQLXWNMMZGQMY-LBPRGKRZSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- AQHVIMVLUSKWPR-UHFFFAOYSA-N CN(C)C1CN(CC1O)C=O Chemical compound CN(C)C1CN(CC1O)C=O AQHVIMVLUSKWPR-UHFFFAOYSA-N 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 1
- YVMHJLSMGPVNSI-ZFWWWQNUSA-N [(3R,4R)-1-[3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxybenzoyl]-4-fluoropyrrolidin-3-yl]methanesulfonic acid Chemical compound NCc1cc(Oc2cccc(c2)C(=O)N2C[C@H](F)[C@H](CS(O)(=O)=O)C2)nc(c1)C(F)(F)F YVMHJLSMGPVNSI-ZFWWWQNUSA-N 0.000 claims 1
- RWQJLIWMOBYOTI-AWEZNQCLSA-N [(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidin-1-yl]-pyridin-3-ylmethanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(=O)C=1C=NC=CC=1 RWQJLIWMOBYOTI-AWEZNQCLSA-N 0.000 claims 1
- WGCOQYDRMPFAMN-ZDUSSCGKSA-N [(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidin-1-yl]-pyrimidin-5-ylmethanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(=O)C=1C=NC=NC=1 WGCOQYDRMPFAMN-ZDUSSCGKSA-N 0.000 claims 1
- PKZVFOVXYKCBCJ-UHFFFAOYSA-N [2-(1H-indol-4-yloxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound N1C=CC2=C(C=CC=C12)OC1=NC(=CC(=C1)CN)C(F)(F)F PKZVFOVXYKCBCJ-UHFFFAOYSA-N 0.000 claims 1
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- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 claims 1
- REAYFGLASQTHKB-UHFFFAOYSA-N [2-[3-(1H-pyrazol-4-yl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound N1N=CC(=C1)C=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 REAYFGLASQTHKB-UHFFFAOYSA-N 0.000 claims 1
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 claims 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 claims 1
- XRSXHZVWZVOWLB-RTBURBONSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-4-phenylmethoxyphenyl]-[(3R,4R)-3-fluoro-4-hydroxypyrrolidin-1-yl]methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1OCC1=CC=CC=C1)C(=O)N1C[C@H]([C@@H](C1)O)F XRSXHZVWZVOWLB-RTBURBONSA-N 0.000 claims 1
- DJDIPNLVNIJRQH-UHFFFAOYSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-(2,5-dihydropyrrol-1-yl)methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1CC=CC1 DJDIPNLVNIJRQH-UHFFFAOYSA-N 0.000 claims 1
- YKKPYMXANSSQCA-UHFFFAOYSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-(3-pyrazol-1-ylazetidin-1-yl)methanone Chemical compound N1(N=CC=C1)C1CN(C1)C(=O)C1=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F YKKPYMXANSSQCA-UHFFFAOYSA-N 0.000 claims 1
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- MDPSWPGUOCQNMH-UHFFFAOYSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-(7-oxa-2-azaspiro[3.5]nonan-2-yl)methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1CC2(C1)CCOCC2 MDPSWPGUOCQNMH-UHFFFAOYSA-N 0.000 claims 1
- ODGXXYXJORZPHE-ZIAGYGMSSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-[(3R,4R)-3-fluoro-4-hydroxypyrrolidin-1-yl]methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1C[C@H]([C@@H](C1)O)F ODGXXYXJORZPHE-ZIAGYGMSSA-N 0.000 claims 1
- ODGXXYXJORZPHE-KGLIPLIRSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-[(3R,4S)-3-fluoro-4-hydroxypyrrolidin-1-yl]methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1C[C@H]([C@H](C1)O)F ODGXXYXJORZPHE-KGLIPLIRSA-N 0.000 claims 1
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- PZDIIXNDZVEGDX-UHFFFAOYSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-[4-(hydroxymethyl)piperidin-1-yl]methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1CCC(CC1)CO PZDIIXNDZVEGDX-UHFFFAOYSA-N 0.000 claims 1
- KDSYNTPPPISIJB-HUUCEWRRSA-N [3-[[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxymethyl]phenyl]-[(3R,4R)-3-fluoro-4-hydroxypyrrolidin-1-yl]methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OCC=1C=C(C=CC=1)C(=O)N1C[C@H]([C@@H](C1)O)F KDSYNTPPPISIJB-HUUCEWRRSA-N 0.000 claims 1
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-
2016
- 2016-03-03 EA EA201791874A patent/EA034891B1/ru not_active IP Right Cessation
- 2016-03-03 ES ES16762186T patent/ES2838977T3/es active Active
- 2016-03-03 EP EP16762186.1A patent/EP3265456B1/en active Active
- 2016-03-03 AU AU2016229268A patent/AU2016229268B2/en not_active Ceased
- 2016-03-03 MX MX2017011269A patent/MX376835B/es active IP Right Grant
- 2016-03-03 CN CN201680026215.8A patent/CN107592861B/zh active Active
- 2016-03-03 SG SG11201707246YA patent/SG11201707246YA/en unknown
- 2016-03-03 BR BR112017019150-4A patent/BR112017019150B1/pt not_active IP Right Cessation
- 2016-03-03 JP JP2017543746A patent/JP6697809B2/ja active Active
- 2016-03-03 WO PCT/US2016/020732 patent/WO2016144703A1/en not_active Ceased
- 2016-03-03 CA CA2977947A patent/CA2977947A1/en active Pending
- 2016-03-03 EP EP20205649.5A patent/EP3795568A1/en active Pending
- 2016-03-03 KR KR1020177027501A patent/KR102594441B1/ko active Active
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2017
- 2017-08-31 IL IL254236A patent/IL254236A0/en unknown
- 2017-09-05 US US15/695,911 patent/US10150732B2/en active Active
- 2017-09-06 PH PH12017501611A patent/PH12017501611A1/en unknown
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2018
- 2018-09-21 US US16/138,680 patent/US10570094B2/en active Active
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2019
- 2019-12-13 US US16/713,314 patent/US11072585B2/en active Active
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2020
- 2020-08-24 AU AU2020220225A patent/AU2020220225A1/en not_active Abandoned
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