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
- TYKKVMXTDTXEFH-UHFFFAOYSA-N [2-(3-phenoxyphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)C=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 TYKKVMXTDTXEFH-UHFFFAOYSA-N 0.000 claims 1
- 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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- XNZLGZUMPGXVDF-UHFFFAOYSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-[3-(methoxymethyl)azetidin-1-yl]methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1CC(C1)COC XNZLGZUMPGXVDF-UHFFFAOYSA-N 0.000 claims 1
- 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
- IQUWAPNUQVLWGG-GFCCVEGCSA-N [5-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypyridin-3-yl]-[(3R)-3-aminopyrrolidin-1-yl]methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=NC=1)C(=O)N1C[C@@H](CC1)N IQUWAPNUQVLWGG-GFCCVEGCSA-N 0.000 claims 1
- 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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| US10766860B2 (en) * | 2015-03-06 | 2020-09-08 | Pharmakea, Inc. | Lysyl oxidase-like 2 inhibitors and uses thereof |
| KR102594441B1 (ko) | 2015-03-06 | 2023-10-25 | 파마케아, 인크. | 플루오르화된 리실 옥시다아제-유사 2 억제제 및 이의 용도 |
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| US20190192697A1 (en) * | 2016-09-07 | 2019-06-27 | Pharmakea, Inc. | Chemical probes of lysyl oxidask-like 2 and uses thereof |
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| AU2018235654B2 (en) * | 2017-03-17 | 2021-11-18 | Mitsui Chemicals Crop & Life Solutions, Inc. | Plant disease control agent |
| WO2019112968A1 (en) | 2017-12-05 | 2019-06-13 | Peng Wang | Processes to produce elagolix |
| 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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| MA52940A (fr) | 2018-05-18 | 2021-04-28 | Incyte Corp | Dérivés de pyrimidine fusionnés utilisés en tant qu'inhibiteurs de a2a/a2b |
| GB201809295D0 (en) | 2018-06-06 | 2018-07-25 | Institute Of Cancer Res Royal Cancer Hospital | Lox inhibitors |
| AU2019297361B2 (en) | 2018-07-05 | 2024-06-27 | Incyte Corporation | Fused pyrazine derivatives as A2A / A2B inhibitors |
| WO2020024017A1 (en) | 2018-08-03 | 2020-02-06 | Pharmaxis Ltd. | Haloallylamine sulfone derivative inhibitors of lysyl oxidases and uses thereof |
| GB201818750D0 (en) | 2018-11-16 | 2019-01-02 | Institute Of Cancer Res Royal Cancer Hospital | Lox inhibitors |
| TWI829857B (zh) | 2019-01-29 | 2024-01-21 | 美商英塞特公司 | 作為a2a / a2b抑制劑之吡唑并吡啶及三唑并吡啶 |
| KR20220040480A (ko) * | 2019-07-25 | 2022-03-30 | 파맥시스 엘티디 | 라이실 옥시다제의 디플루오로할로알릴아민 설폰 유도체 저해제, 제조 방법, 및 이의 용도 |
| KR102799014B1 (ko) | 2019-11-06 | 2025-04-28 | 주식회사유한양행 | 피롤리딘 및 피페리딘 화합물 |
| JP2023523036A (ja) * | 2020-04-21 | 2023-06-01 | アノヴィア バイオサイエンシズ，インコーポレーテッド | Ｌｏｘ酵素阻害方法及び組成物 |
| US20230301950A1 (en) | 2020-06-26 | 2023-09-28 | Raqualia Pharma Inc. | Method for selecting cancer patients for whom combination therapy with retinoid and cancer therapeutic agent is effective, and combination medicament with retinoid and cancer therapeutic agent |
| KR102608183B1 (ko) * | 2021-03-11 | 2023-11-30 | 연세대학교 산학협력단 | 신규한 인돌라진 유도체 및 이를 포함하는 암의 예방 또는 치료용 조성물 |
| KR102631074B1 (ko) * | 2021-04-09 | 2024-01-30 | 연세대학교 산학협력단 | 신규한 인돌라진 유도체 및 이를 포함하는 섬유증의 예방 또는 치료용 조성물 |
| EP4422618A4 (en) * | 2021-10-28 | 2025-07-23 | Anovia Biosciences Inc | METHODS AND COMPOSITIONS FOR INHIBITING THE LOX ENZYME |
| US12233056B2 (en) | 2022-04-06 | 2025-02-25 | Syntara Limited | Lysyl oxidase inhibitors for treating myeloid malignancies |
| GB202209622D0 (en) | 2022-06-30 | 2022-08-17 | Institute Of Cancer Res Royal Cancer Hospital | Compounds |
| GB202209624D0 (en) | 2022-06-30 | 2022-08-17 | Institute Of Cancer Res Royal Cancer Hospital | Prodrugs |
Family Cites Families (67)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1015073A (en) | 1911-06-19 | 1912-01-16 | Ley P Rexford | Knockdown brooder. |
| US1077406A (en) | 1912-03-18 | 1913-11-04 | Edward Hixon | Apparatus for treating water. |
| US4229447A (en) | 1979-06-04 | 1980-10-21 | American Home Products Corporation | Intraoral methods of using benzodiazepines |
| IE56702B1 (en) | 1982-12-01 | 1991-11-06 | Usv Pharma Corp | Antiinflammatory antiallergic compounds |
| US4596795A (en) | 1984-04-25 | 1986-06-24 | The United States Of America As Represented By The Secretary, Dept. Of Health & Human Services | Administration of sex hormones in the form of hydrophilic cyclodextrin derivatives |
| US4755386A (en) | 1986-01-22 | 1988-07-05 | Schering Corporation | Buccal formulation |
| CA1338647C (en) * | 1988-02-25 | 1996-10-15 | Michael G. Palfreyman | Inhibitors of lysyl oxidase |
| US5021456A (en) * | 1988-02-25 | 1991-06-04 | Merrell Dow Pharmaceuticals Inc. | Inhibitors of lysyl oxidase |
| US5739136A (en) | 1989-10-17 | 1998-04-14 | Ellinwood, Jr.; Everett H. | Intraoral dosing method of administering medicaments |
| US5250532A (en) | 1991-04-11 | 1993-10-05 | Dowelanco | 3,4,N-trisubstituted-4,5-dihydro-1H-pyrazole-1-carboxamides and their use as insecticides |
| US5563143A (en) | 1994-09-21 | 1996-10-08 | Pfizer Inc. | Catechol diether compounds as inhibitors of TNF release |
| US6956047B1 (en) | 1995-06-06 | 2005-10-18 | Pfizer Inc. | Corticotropin releasing factor antagonists |
| US7067664B1 (en) | 1995-06-06 | 2006-06-27 | Pfizer Inc. | Corticotropin releasing factor antagonists |
| US6632823B1 (en) | 1997-12-22 | 2003-10-14 | Merck & Co., Inc. | Substituted pyridine compounds useful as modulators of acetylcholine receptors |
| MXPA02007047A (es) | 2000-01-18 | 2002-12-13 | Pfizer Prod Inc | Antagonista del factor liberador de corticotropina. |
| US20020147198A1 (en) | 2001-01-12 | 2002-10-10 | Guoqing Chen | Substituted arylamine derivatives and methods of use |
| US6995162B2 (en) | 2001-01-12 | 2006-02-07 | Amgen Inc. | Substituted alkylamine derivatives and methods of use |
| US7102009B2 (en) | 2001-01-12 | 2006-09-05 | Amgen Inc. | Substituted amine derivatives and methods of use |
| US6878714B2 (en) | 2001-01-12 | 2005-04-12 | Amgen Inc. | Substituted alkylamine derivatives and methods of use |
| US7105682B2 (en) | 2001-01-12 | 2006-09-12 | Amgen Inc. | Substituted amine derivatives and methods of use |
| US20030134836A1 (en) | 2001-01-12 | 2003-07-17 | Amgen Inc. | Substituted arylamine derivatives and methods of use |
| TWI319387B (en) | 2002-04-05 | 2010-01-11 | Astrazeneca Ab | Benzamide derivatives |
| US7307088B2 (en) | 2002-07-09 | 2007-12-11 | Amgen Inc. | Substituted anthranilic amide derivatives and methods of use |
| FI20030030A0 (fi) | 2003-01-09 | 2003-01-09 | Orion Corp | Uusia yhdisteitä |
| BRPI0410454A (pt) | 2003-05-19 | 2006-06-13 | Irm Llc | composições e compostos imunossupressores |
| WO2007016784A1 (en) | 2005-08-11 | 2007-02-15 | Merck Frosst Canada Ltd. | Novel substituted 1,2,3-tπazolylmethyl-benzothiophene or -indole and their use as leukotπene biosynthesis inhibitors |
| EP1715868A1 (en) | 2004-01-29 | 2006-11-02 | Pfizer Products Incorporated | Combinations of an atypical antipsychotic and an aminomethylpyridyloxymethyl/benzisoxazole azabicyclic derivatives for treating cns disorders |
| DE602005022572D1 (de) | 2004-03-12 | 2010-09-09 | Lilly Co Eli | Antagonisten des opioidrezeptors |
| EP1735268B1 (en) | 2004-03-15 | 2012-02-15 | Eli Lilly And Company | Opioid receptor antagonists |
| US9212149B2 (en) | 2004-04-30 | 2015-12-15 | Takeda Pharmaceutical Company Limited | Substituted 2-amidoquinazol-4-ones as matrix metalloproteinase-13 inhibitors |
| US7507748B2 (en) | 2004-07-22 | 2009-03-24 | Amgen Inc. | Substituted aryl-amine derivatives and methods of use |
| CA2580034A1 (en) | 2004-09-10 | 2006-03-16 | Pfizer Products Inc. | Methods of treating mood disorders using benzisoxazole containing diazabicyclic compounds |
| EP1791540A2 (en) | 2004-09-10 | 2007-06-06 | Pfizer Products Incorporated | Methods of treating cognitive disorders using pyridyloxymethyl and benzisoxazole azabicyclic derivatives |
| WO2006052546A2 (en) | 2004-11-04 | 2006-05-18 | Neurogen Corporation | Pyrazolylmethyl heteroaryl derivatives |
| DE102004056226A1 (de) * | 2004-11-22 | 2006-05-24 | Burchardt, Elmar Reinhold, Dr.Dr. | Neuartige Inhibitoren der Lysyloxidase |
| US7759493B2 (en) | 2005-01-31 | 2010-07-20 | Merck Sharp & Dohme Corp. | Antidiabetic bicyclic compounds |
| AR055041A1 (es) | 2005-03-23 | 2007-08-01 | Merck Frosst Canada Ltd | Tiadiazoles y oxadiazoles como inhibidores de la sintesis de leucotrienos. composiciones farmaceuticas. |
| US7405302B2 (en) | 2005-10-11 | 2008-07-29 | Amira Pharmaceuticals, Inc. | 5-lipoxygenase-activating protein (FLAP) inhibitors |
| ITMI20051943A1 (it) | 2005-10-14 | 2007-04-15 | Procos Spa | Processo di risoluzione anantiomerica di 2-aminometil-pirrolidine 1-sostitute per ammidazione in presenza di lipasi |
| US20070225285A1 (en) | 2005-11-04 | 2007-09-27 | Amira Pharmaceuticals, Inc. | 5-lipoxygenase-activating protein (flap) inhibitors |
| US7977359B2 (en) | 2005-11-04 | 2011-07-12 | Amira Pharmaceuticals, Inc. | 5-lipdxygenase-activating protein (FLAP) inhibitors |
| US20070219206A1 (en) | 2005-11-04 | 2007-09-20 | Amira Pharmaceuticals, Inc. | 5-lipoxygenase-activating protein (flap) inhibitors |
| JP2009523820A (ja) | 2006-01-23 | 2009-06-25 | アミラ ファーマシューティカルス，インコーポレーテッド | ５−リポキシゲナーゼの三環系抑制剤 |
| GB0614579D0 (en) | 2006-07-21 | 2006-08-30 | Black James Foundation | Pyrimidine derivatives |
| WO2008020799A1 (en) | 2006-08-18 | 2008-02-21 | Astrazeneca Ab | Thienopyrimidin-4-one and thienopyridazin-7-one derivatives as mch rl antagonists |
| IL184627A0 (en) | 2007-07-15 | 2008-12-29 | Technion Res & Dev Foundation | Agents for diagnosing and modulating metastasis and fibrosis as well as inflammation in a mammalian tissue |
| WO2009017833A2 (en) | 2007-08-02 | 2009-02-05 | Arresto Biosciences | Methods and compositions for treatment and diagnosis of fibrosis, tumor invasion, angiogenesis, and metastasis |
| WO2011017125A1 (en) | 2009-07-28 | 2011-02-10 | Anacor Pharmaceuticals, Inc. | Trisubstituted boron-containing molecules |
| CN102711821A (zh) | 2009-08-21 | 2012-10-03 | 吉联亚生物科技有限公司 | 治疗方法和组合物 |
| EP2531217A4 (en) | 2010-02-04 | 2013-11-27 | Gilead Biologics Inc | ANTIBODIES THAT BIND TO LOXL2 (LYSYL OXIDASE-LIKE 2) AND METHODS OF USE THEREOF |
| WO2011097594A2 (en) | 2010-02-08 | 2011-08-11 | Kinagen, Inc. | Therapeutic methods and compositions involving allosteric kinase inhibition |
| CN103002742B (zh) * | 2010-03-05 | 2016-07-13 | 卡尔约药物治疗公司 | 核转运调节剂及其应用 |
| WO2011150201A2 (en) | 2010-05-27 | 2011-12-01 | Ambit Biosciences Corporation | Azolyl amide compounds and methods of use thereof |
| EP2441755A1 (en) | 2010-09-30 | 2012-04-18 | Almirall, S.A. | Pyridine- and isoquinoline-derivatives as Syk and JAK kinase inhibitors |
| EP2640723A1 (en) | 2010-11-19 | 2013-09-25 | Incyte Corporation | Cyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as jak inhibitors |
| TW201313721A (zh) * | 2011-08-18 | 2013-04-01 | Incyte Corp | 作為ｊａｋ抑制劑之環己基氮雜環丁烷衍生物 |
| CN104394869A (zh) * | 2011-10-20 | 2015-03-04 | 葛兰素史密斯克莱有限责任公司 | 用作沉默调节蛋白调节剂的取代的双环氮杂杂环化合物和类似物 |
| EP2841421B1 (en) * | 2012-04-25 | 2019-06-05 | RaQualia Pharma Inc | Amide derivatives as ttx-s blockers |
| SG11201503065PA (en) | 2012-10-30 | 2015-05-28 | Gilead Sciences Inc | Therapeutic and diagnostic methods related to lysyl oxidase-like 2 (loxl2) |
| WO2014098098A1 (ja) | 2012-12-18 | 2014-06-26 | 味の素株式会社 | 複素環アミド誘導体及びそれを含有する医薬 |
| AU2015298491A1 (en) | 2014-02-14 | 2016-09-01 | The University Of British Columbia | Modulators of caspase-6 |
| US9051320B1 (en) | 2014-08-18 | 2015-06-09 | Pharmakea, Inc. | Methods for the treatment of metabolic disorders by a selective small molecule autotaxin inhibitor |
| BR112017017052A2 (pt) * | 2015-02-15 | 2018-04-10 | F. Hoffmann-La Roche Ag | derivados de 1-(het)arilsulfonil-(pirrolidina ou piperidina)-2-carboxamida e seu uso como antagonistas de trpa1 |
| KR102594441B1 (ko) | 2015-03-06 | 2023-10-25 | 파마케아, 인크. | 플루오르화된 리실 옥시다아제-유사 2 억제제 및 이의 용도 |
| US10766860B2 (en) | 2015-03-06 | 2020-09-08 | Pharmakea, Inc. | Lysyl oxidase-like 2 inhibitors and uses thereof |
| AU2017324445A1 (en) | 2016-09-07 | 2019-04-11 | Pharmakea, Inc. | Crystalline forms of a lysyl oxidase-like 2 inhibitor and methods of making |
| BR112019004513A2 (pt) | 2016-09-07 | 2019-06-18 | Pharmakea Inc | usos de um inibidor de lisil oxidase-like 2 |
-
2016
- 2016-03-03 KR KR1020177027501A patent/KR102594441B1/ko active Active
- 2016-03-03 ES ES16762186T patent/ES2838977T3/es active Active
- 2016-03-03 AU AU2016229268A patent/AU2016229268B2/en not_active Ceased
- 2016-03-03 EP EP20205649.5A patent/EP3795568A1/en active Pending
- 2016-03-03 EP EP16762186.1A patent/EP3265456B1/en active Active
- 2016-03-03 JP JP2017543746A patent/JP6697809B2/ja active Active
- 2016-03-03 CN CN201680026215.8A patent/CN107592861B/zh active Active
- 2016-03-03 MX MX2017011269A patent/MX376835B/es active IP Right Grant
- 2016-03-03 SG SG11201707246YA patent/SG11201707246YA/en unknown
- 2016-03-03 EA EA201791874A patent/EA034891B1/ru not_active IP Right Cessation
- 2016-03-03 CA CA2977947A patent/CA2977947A1/en active Pending
- 2016-03-03 WO PCT/US2016/020732 patent/WO2016144703A1/en not_active Ceased
- 2016-03-03 BR BR112017019150-4A patent/BR112017019150B1/pt not_active IP Right Cessation
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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
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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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- 2020-08-24 AU AU2020220225A patent/AU2020220225A1/en not_active Abandoned
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