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
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- 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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- 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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- UGKIKJFPXNOHHA-CHWSQXEVSA-N [5-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypyridin-3-yl]-[(3R,4R)-3-fluoro-4-hydroxypyrrolidin-1-yl]methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=NC=1)C(=O)N1C[C@H]([C@@H](C1)O)F UGKIKJFPXNOHHA-CHWSQXEVSA-N 0.000 claims 1
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| CA3056563C (en) * | 2017-03-17 | 2023-03-14 | Meiji Seika Pharma Co., Ltd. | Plant disease control agent |
| JP7200261B2 (ja) | 2017-12-05 | 2023-01-06 | スージョウ ポンシュー ファーマテック カンパニー リミテッド | エラゴリクスを作製するプロセス |
| CN110128355A (zh) * | 2018-01-17 | 2019-08-16 | 苏州鹏旭医药科技有限公司 | 一种含有6-甲基尿嘧啶结构化合物的制备方法 |
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| WO2021261601A1 (ja) | 2020-06-26 | 2021-12-30 | ラクオリア創薬株式会社 | レチノイドとがん治療薬との併用療法が有効ながん患者の選択方法およびレチノイドとがん治療薬との併用医薬 |
| KR102608183B1 (ko) * | 2021-03-11 | 2023-11-30 | 연세대학교 산학협력단 | 신규한 인돌라진 유도체 및 이를 포함하는 암의 예방 또는 치료용 조성물 |
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-
2016
- 2016-03-03 AU AU2016229268A patent/AU2016229268B2/en not_active Ceased
- 2016-03-03 EP EP16762186.1A patent/EP3265456B1/en active Active
- 2016-03-03 SG SG11201707246YA patent/SG11201707246YA/en unknown
- 2016-03-03 MX MX2017011269A patent/MX376835B/es active IP Right Grant
- 2016-03-03 EA EA201791874A patent/EA034891B1/ru not_active IP Right Cessation
- 2016-03-03 EP EP20205649.5A patent/EP3795568A1/en active Pending
- 2016-03-03 ES ES16762186T patent/ES2838977T3/es active Active
- 2016-03-03 CA CA2977947A patent/CA2977947A1/en active Pending
- 2016-03-03 BR BR112017019150-4A patent/BR112017019150B1/pt not_active IP Right Cessation
- 2016-03-03 WO PCT/US2016/020732 patent/WO2016144703A1/en not_active Ceased
- 2016-03-03 KR KR1020177027501A patent/KR102594441B1/ko active Active
- 2016-03-03 JP JP2017543746A patent/JP6697809B2/ja active Active
- 2016-03-03 CN CN201680026215.8A patent/CN107592861B/zh 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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