JP2018512381A5 - - Google Patents
Download PDFInfo
- 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
Links
- -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
- ACRMKYRSNHFWLB-UHFFFAOYSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-(4-hydroxy-4-methylpiperidin-1-yl)methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1CCC(CC1)(C)O ACRMKYRSNHFWLB-UHFFFAOYSA-N 0.000 claims 1
- 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
- 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
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims 1
- 125000004069 aziridinyl group Chemical group 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- CVPXHDQGCQSZFO-UHFFFAOYSA-N methyl 3-[[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]carbamoyl]benzoate Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)NC(=O)C=1C=C(C(=O)OC)C=CC=1 CVPXHDQGCQSZFO-UHFFFAOYSA-N 0.000 claims 1
- 125000001620 monocyclic carbocycle group Chemical group 0.000 claims 1
- OEOGBZSTOSHSAY-UHFFFAOYSA-N n-(4-methyl-2-oxochromen-7-yl)benzamide Chemical compound C1=CC=2C(C)=CC(=O)OC=2C=C1NC(=O)C1=CC=CC=C1 OEOGBZSTOSHSAY-UHFFFAOYSA-N 0.000 claims 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000003551 oxepanyl group Chemical group 0.000 claims 1
- 125000003566 oxetanyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 claims 1
- 125000001583 thiepanyl group Chemical group 0.000 claims 1
- 125000002053 thietanyl group Chemical group 0.000 claims 1
- 125000004306 triazinyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562129543P | 2015-03-06 | 2015-03-06 | |
| US62/129,543 | 2015-03-06 | ||
| PCT/US2016/020732 WO2016144703A1 (en) | 2015-03-06 | 2016-03-03 | Fluorinated lysyl oxidase-like 2 inhibitors and uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018512381A JP2018512381A (ja) | 2018-05-17 |
| JP2018512381A5 true JP2018512381A5 (enExample) | 2019-04-11 |
| JP6697809B2 JP6697809B2 (ja) | 2020-05-27 |
Family
ID=56879638
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017543746A Active JP6697809B2 (ja) | 2015-03-06 | 2016-03-03 | フッ素化リシルオキシダーゼ様２阻害剤とその使用 |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US10150732B2 (enExample) |
| EP (2) | EP3795568A1 (enExample) |
| JP (1) | JP6697809B2 (enExample) |
| KR (1) | KR102594441B1 (enExample) |
| CN (1) | CN107592861B (enExample) |
| AU (2) | AU2016229268B2 (enExample) |
| BR (1) | BR112017019150B1 (enExample) |
| CA (1) | CA2977947A1 (enExample) |
| EA (1) | EA034891B1 (enExample) |
| ES (1) | ES2838977T3 (enExample) |
| IL (1) | IL254236A0 (enExample) |
| MX (1) | MX376835B (enExample) |
| PH (1) | PH12017501611A1 (enExample) |
| SG (1) | SG11201707246YA (enExample) |
| WO (1) | WO2016144703A1 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016144702A1 (en) | 2015-03-06 | 2016-09-15 | Pharmakea, Inc. | Lysyl oxidase-like 2 inhibitors and uses thereof |
| WO2016144703A1 (en) | 2015-03-06 | 2016-09-15 | Pharmakea, Inc. | Fluorinated lysyl oxidase-like 2 inhibitors and uses thereof |
| GB201602934D0 (en) | 2016-02-19 | 2016-04-06 | Cancer Res Inst Royal | Compounds |
| MX390964B (es) | 2016-09-07 | 2025-03-21 | Pharmakea Inc | Formas cristalinas de un inhibidor tipo lisil oxidasa 2 y metodos de realizacion. |
| WO2018048928A1 (en) * | 2016-09-07 | 2018-03-15 | Pharmakea, Inc. | Chemical probes of lysyl oxidase-like 2 and uses thereof |
| MX2019002612A (es) * | 2016-09-07 | 2019-08-21 | Pharmakea Inc | Usos de un inhibidor de lisil-oxidasa tipo 2. |
| JP7064097B2 (ja) * | 2017-03-17 | 2022-05-10 | 株式会社Mmag | 植物病害防除剤 |
| 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 |
| 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 |
| BR122023024273A2 (pt) | 2018-02-27 | 2024-02-20 | Incyte Corporation | Compostos imidazopirimidinas e triazolopirimidinas, seus usos, método para inibir uma atividade de um receptor de adenosina e composição farmacêutica dos mesmos |
| EP3810610A1 (en) | 2018-05-18 | 2021-04-28 | Incyte Corporation | Fused pyrimidine derivatives as a2a / a2b inhibitors |
| 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 |
| CA3105599A1 (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 |
| AU2020317374A1 (en) * | 2019-07-25 | 2022-02-03 | Pharmaxis Ltd. | Difluorohaloallylamine sulfone derivative inhibitors of lysyl oxidases, methods of preparation, and uses thereof |
| CA3160627A1 (en) | 2019-11-06 | 2021-05-14 | Yuhan Corporation | Pyrrolidine and piperidine compounds |
| WO2021155439A1 (en) | 2020-02-05 | 2021-08-12 | Pharmaxis Ltd. | Bioprobes for lysyl oxidases and uses thereof |
| 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 |
| JP7327855B2 (ja) | 2020-06-26 | 2023-08-16 | 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 |
| 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 |
| US5021456A (en) * | 1988-02-25 | 1991-06-04 | Merrell Dow Pharmaceuticals Inc. | Inhibitors of lysyl oxidase |
| AU618076B2 (en) * | 1988-02-25 | 1991-12-12 | Merrell Dow Pharmaceuticals Inc. | Inhibitors of lysyloxidase |
| 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. |
| US6995162B2 (en) | 2001-01-12 | 2006-02-07 | 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 |
| US20020147198A1 (en) | 2001-01-12 | 2002-10-10 | Guoqing Chen | Substituted arylamine derivatives and methods of use |
| US6878714B2 (en) | 2001-01-12 | 2005-04-12 | 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 |
| 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 |
| CN1787817B (zh) | 2003-05-19 | 2011-09-07 | Irm责任有限公司 | 免疫抑制剂化合物及组合物 |
| WO2005082370A1 (en) | 2004-01-29 | 2005-09-09 | Pfizer Products Inc. | Combinations of an atypical antipsychotic and an aminomethylpyridyloxymethyl/benzisoxazole azabicyclic derivatives for treating cns disorders |
| CA2558568A1 (en) | 2004-03-12 | 2005-09-29 | Eli Lilly And Company | Opioid receptor antagonists |
| WO2005092836A1 (en) | 2004-03-15 | 2005-10-06 | Eli Lilly And Company | Opioid receptor antagonists |
| CN1976907A (zh) | 2004-04-30 | 2007-06-06 | 武田药品工业株式会社 | 杂环酰胺化合物及其作为mmp－13抑制剂的用途 |
| US7507748B2 (en) | 2004-07-22 | 2009-03-24 | Amgen Inc. | Substituted aryl-amine derivatives and methods of use |
| BRPI0515143A (pt) | 2004-09-10 | 2008-07-08 | Pfizer Prod Inc | usos de derivados azabicìclicos de piridiloximetila e benzisoxazol para a preparação de uma composição farmacêutica para o tratamento dos distúrbios de humor |
| JP2008512441A (ja) | 2004-09-10 | 2008-04-24 | ファイザー・プロダクツ・インク | ピリジルオキシメチル、及びベンズイソオキサゾール・アザビシクロ誘導体を使用する、認知障害の治療方法 |
| 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. |
| CA2618586A1 (en) | 2005-08-11 | 2007-02-15 | Merck Frosst Canada Ltd. | Novel substituted 1,2,3-triazolylmethyl-benzothiophene or -indole and their use as leukotriene biosynthesis inhibitors |
| 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 |
| 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 |
| US20070225285A1 (en) | 2005-11-04 | 2007-09-27 | Amira Pharmaceuticals, Inc. | 5-lipoxygenase-activating protein (flap) inhibitors |
| WO2007087250A2 (en) | 2006-01-23 | 2007-08-02 | Amira Pharmaceuticals, Inc. | Tricyclic inhibitors of 5-lipoxygenase |
| GB0614579D0 (en) | 2006-07-21 | 2006-08-30 | Black James Foundation | Pyrimidine derivatives |
| EP2121703A4 (en) | 2006-08-18 | 2011-12-28 | Astrazeneca Ab | THIENOPYRIMIDIN-4-ON- AND THIENOPYRIDAZIN-7-ONDERIVATES 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 |
| ES2700141T3 (es) | 2007-08-02 | 2019-02-14 | Gilead Biologics Inc | Anticuerpos inhibidores LOXL2 y usos de los mismos |
| KR20130031233A (ko) | 2009-07-28 | 2013-03-28 | 아나코르 파마슈티칼스 인코포레이티드 | 삼치환된 붕소 함유 분자 |
| EP2467162A4 (en) | 2009-08-21 | 2013-10-02 | Gilead Biologics Inc | THERAPEUTIC PROCESSES AND RELATED COMPOSITIONS |
| US8680246B2 (en) | 2010-02-04 | 2014-03-25 | Gilead Biologics, Inc. | Antibodies that bind to lysyl oxidase-like 2 (LOXL2) |
| JP2013518909A (ja) | 2010-02-08 | 2013-05-23 | キナゲン，インク． | アロステリックキナーゼ阻害が関係する治療方法および組成物 |
| US8513230B2 (en) * | 2010-03-05 | 2013-08-20 | Karyopharm Therapeutics, Inc. | Nuclear transport modulators and uses thereof |
| 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 |
| CA2818542A1 (en) * | 2010-11-19 | 2012-05-24 | 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 |
| RU2014120166A (ru) * | 2011-10-20 | 2015-11-27 | ГЛЭКСОСМИТКЛАЙН ЭлЭлСи | Замещенные бициклические аза-гетероциклы и их аналоги в качестве модуляторов сиртуина |
| BR112014026399B1 (pt) * | 2012-04-25 | 2022-11-01 | Raqualia Pharma Inc | Composto de fórmula (ii), composição farmacêutica, uso e processo para preparar uma composição farmacêutica |
| JP2016500700A (ja) | 2012-10-30 | 2016-01-14 | ギリアード サイエンシーズ， インコーポレイテッド | リシルオキシダーゼ様２（ｌｏｘｌ２）に関する治療および診断方法 |
| CN104854086B (zh) | 2012-12-18 | 2017-06-27 | Ea制药株式会社 | 杂环酰胺衍生物和含有其的药物 |
| JP2018522812A (ja) | 2014-08-05 | 2018-08-16 | ザ ユニヴァーシティ オブ ブリティッシュ コロンビア | カスパーゼ−６のモジュレーター |
| US9051320B1 (en) | 2014-08-18 | 2015-06-09 | Pharmakea, Inc. | Methods for the treatment of metabolic disorders by a selective small molecule autotaxin inhibitor |
| WO2016128529A1 (en) * | 2015-02-15 | 2016-08-18 | F. Hoffmann-La Roche Ag | 1-(het)arylsulfonyl-(pyrrolidine or piperidine)-2-carboxamide derivatives and their use as trpa1 antagonists |
| WO2016144703A1 (en) | 2015-03-06 | 2016-09-15 | Pharmakea, Inc. | Fluorinated lysyl oxidase-like 2 inhibitors and uses thereof |
| WO2016144702A1 (en) | 2015-03-06 | 2016-09-15 | Pharmakea, Inc. | Lysyl oxidase-like 2 inhibitors and uses thereof |
| MX390964B (es) | 2016-09-07 | 2025-03-21 | Pharmakea Inc | Formas cristalinas de un inhibidor tipo lisil oxidasa 2 y metodos de realizacion. |
| MX2019002612A (es) | 2016-09-07 | 2019-08-21 | Pharmakea Inc | Usos de un inhibidor de lisil-oxidasa tipo 2. |
-
2016
- 2016-03-03 WO PCT/US2016/020732 patent/WO2016144703A1/en not_active Ceased
- 2016-03-03 CN CN201680026215.8A patent/CN107592861B/zh active Active
- 2016-03-03 JP JP2017543746A patent/JP6697809B2/ja 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 SG SG11201707246YA patent/SG11201707246YA/en unknown
- 2016-03-03 ES ES16762186T patent/ES2838977T3/es active Active
- 2016-03-03 EA EA201791874A patent/EA034891B1/ru not_active IP Right Cessation
- 2016-03-03 KR KR1020177027501A patent/KR102594441B1/ko active Active
- 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 BR BR112017019150-4A patent/BR112017019150B1/pt not_active IP Right Cessation
- 2016-03-03 CA CA2977947A patent/CA2977947A1/en active Pending
-
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
-
2018
- 2018-09-21 US US16/138,680 patent/US10570094B2/en active Active
-
2019
- 2019-12-13 US US16/713,314 patent/US11072585B2/en active Active
-
2020
- 2020-08-24 AU AU2020220225A patent/AU2020220225A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2934137C (en) | Novel carboxamides, method for the production thereof, pharmaceutical preparations comprising them, and use thereof for producing medicaments | |
| JP6231085B2 (ja) | アミノキナゾリン誘導体及びピリドピリミジン誘導体 | |
| ES2644724T3 (es) | Indazoles sustituidos con oxazol como inhibidores de PI3-cinasas | |
| TWI481608B (zh) | 作為ｊａｋ抑制劑之咪唑並吡啶衍生物 | |
| JP5714573B2 (ja) | キヌレニン産生抑制作用を有する含窒素複素環化合物 | |
| JP2017519021A5 (enExample) | ||
| JP5494482B2 (ja) | トリアゾール誘導体またはその塩 | |
| RU2011107437A (ru) | Ингибиторы кинуренин-3-моноксигеназы | |
| US20140256949A1 (en) | Quinolyl amines as kinase inhibitors | |
| US20160060222A1 (en) | Amino-quinolines as kinase inhibitors | |
| RU2016102137A (ru) | Первичные карбоксамиды в качестве ингибиторов bik | |
| TW201639829A (zh) | 經取代磺醯胺化合物 | |
| JP2014531465A5 (enExample) | ||
| KR20200103760A (ko) | Parp14 억제제로서의 퀴나졸리논 | |
| WO2011021678A1 (ja) | 縮合複素環化合物 | |
| JP2018512408A (ja) | Ｐｈｄ阻害剤としての縮合二環式ヘテロアリール誘導体 | |
| RU2007130153A (ru) | Амидные производные | |
| RU2013152961A (ru) | Изоксазолины в качестве терапевтических агентов | |
| JP2014513122A5 (enExample) | ||
| JP2025509895A (ja) | Ｔｅａドメインファミリーメンバーの小分子阻害薬 | |
| JP2013522372A5 (enExample) | ||
| WO2022180003A1 (en) | Benzothiazolyl bicyclo[1.1.1]pentane derivatives for the treatment and prophylaxis of hepatitis b virus infection | |
| CN121591731A (zh) | 一种杂环化合物 | |
| AU2016289079A1 (en) | Novel imide derivatives and use thereof as medicine | |
| US20230365531A1 (en) | Inhibitors of human respiratory syncytial virus and metapneumo virus |