JP2018510852A5 - - Google Patents
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- JP2018510852A5 JP2018510852A5 JP2017545627A JP2017545627A JP2018510852A5 JP 2018510852 A5 JP2018510852 A5 JP 2018510852A5 JP 2017545627 A JP2017545627 A JP 2017545627A JP 2017545627 A JP2017545627 A JP 2017545627A JP 2018510852 A5 JP2018510852 A5 JP 2018510852A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- aminomethyl
- pyridin
- oxy
- 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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- 150000001875 compounds Chemical class 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 18
- -1 heterocyclic ring bicyclic compound Chemical class 0.000 claims description 11
- LIUIDMWKNRWMIS-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]-N-benzylbenzamide Chemical compound NCC1=CC(=NC=C1)C=1C=C(C(=O)NCC2=CC=CC=C2)C=CC=1 LIUIDMWKNRWMIS-UHFFFAOYSA-N 0.000 claims description 3
- LLRXFUQAAZQTBR-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-(2,4-difluorophenyl)benzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NC2=C(C=C(C=C2)F)F)C=CC=1 LLRXFUQAAZQTBR-UHFFFAOYSA-N 0.000 claims description 3
- IIJOUPDJYSTSBW-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-(3-methoxyphenyl)benzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NC2=CC(=CC=C2)OC)C=CC=1 IIJOUPDJYSTSBW-UHFFFAOYSA-N 0.000 claims description 3
- KKSAXTCEFKJMEZ-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-(4-methoxyphenyl)benzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NC2=CC=C(C=C2)OC)C=CC=1 KKSAXTCEFKJMEZ-UHFFFAOYSA-N 0.000 claims description 3
- ZOGOKEYUMAJDEO-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-[3-(trifluoromethyl)phenyl]benzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NC2=CC(=CC=C2)C(F)(F)F)C=CC=1 ZOGOKEYUMAJDEO-UHFFFAOYSA-N 0.000 claims description 3
- XGRLLLJVGNTYSK-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-tridecylbenzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NCCCCCCCCCCCCC)C=CC=1 XGRLLLJVGNTYSK-UHFFFAOYSA-N 0.000 claims description 3
- CIBGXOAZCPUGAU-UHFFFAOYSA-N 4-[4-(aminomethyl)pyridin-2-yl]-N-phenylbenzamide Chemical compound NCC1=CC(=NC=C1)C1=CC=C(C(=O)NC2=CC=CC=C2)C=C1 CIBGXOAZCPUGAU-UHFFFAOYSA-N 0.000 claims description 3
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims description 3
- KQALDCNFWKKTOY-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]-N-(2-methoxyethyl)benzamide Chemical compound NCC1=CC(=NC=C1)C=1C=C(C(=O)NCCOC)C=CC=1 KQALDCNFWKKTOY-UHFFFAOYSA-N 0.000 claims description 2
- FJYDBKYVCJLPTH-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]-N-(5-chloro-2-methylphenyl)benzamide Chemical compound NCC1=CC(=NC=C1)C=1C=C(C(=O)NC2=C(C=CC(=C2)Cl)C)C=CC=1 FJYDBKYVCJLPTH-UHFFFAOYSA-N 0.000 claims description 2
- ABFLLPKYLYQDMD-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]-N-(6-chloro-1H-indol-4-yl)benzamide Chemical compound NCC1=CC(=NC=C1)C=1C=C(C(=O)NC2=C3C=CNC3=CC(=C2)Cl)C=CC=1 ABFLLPKYLYQDMD-UHFFFAOYSA-N 0.000 claims description 2
- GTRIVUDDNMZGDQ-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]-N-phenylbenzamide Chemical compound NCC1=CC(=NC=C1)C=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 GTRIVUDDNMZGDQ-UHFFFAOYSA-N 0.000 claims description 2
- HZOSNBJSMRCDMY-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-(1-benzothiophen-2-ylmethyl)benzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NCC2=CC3=C(S2)C=CC=C3)C=CC=1 HZOSNBJSMRCDMY-UHFFFAOYSA-N 0.000 claims description 2
- IUMJMWGBIFYVAC-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-(2-methoxyethyl)benzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NCCOC)C=CC=1 IUMJMWGBIFYVAC-UHFFFAOYSA-N 0.000 claims description 2
- WKJSUDSRVONOIH-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-(2-phenylethyl)benzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NCCC2=CC=CC=C2)C=CC=1 WKJSUDSRVONOIH-UHFFFAOYSA-N 0.000 claims description 2
- BFTRSRQMNCXYRT-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-(4-bromophenyl)benzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NC2=CC=C(C=C2)Br)C=CC=1 BFTRSRQMNCXYRT-UHFFFAOYSA-N 0.000 claims description 2
- RPTMISIWMXZWAU-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-(4-fluorophenyl)benzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NC2=CC=C(C=C2)F)C=CC=1 RPTMISIWMXZWAU-UHFFFAOYSA-N 0.000 claims description 2
- QVNMODWDNBHNGS-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-(pyrazin-2-ylmethyl)benzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NCC2=NC=CN=C2)C=CC=1 QVNMODWDNBHNGS-UHFFFAOYSA-N 0.000 claims description 2
- BKJHKBNJSCIQOY-IBGZPJMESA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-[(1R)-2-hydroxy-1-phenylethyl]benzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)N[C@@H](CO)C2=CC=CC=C2)C=CC=1 BKJHKBNJSCIQOY-IBGZPJMESA-N 0.000 claims description 2
- BHKAZBAZIKMOGM-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-[(2,4-difluorophenyl)methyl]benzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NCC2=C(C=C(C=C2)F)F)C=CC=1 BHKAZBAZIKMOGM-UHFFFAOYSA-N 0.000 claims description 2
- YWVZYIAESUQULQ-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-[(3-carbamimidoylphenyl)methyl]benzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NCC2=CC(=CC=C2)C(N)=N)C=CC=1 YWVZYIAESUQULQ-UHFFFAOYSA-N 0.000 claims description 2
- HEURIQPAZZQVGE-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-[(3-fluoro-4-imidazol-1-ylphenyl)methyl]benzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NCC2=CC(=C(C=C2)N2C=NC=C2)F)C=CC=1 HEURIQPAZZQVGE-UHFFFAOYSA-N 0.000 claims description 2
- HOLNIDQMPCIVFH-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-[(4-bromophenyl)methyl]benzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NCC2=CC=C(C=C2)Br)C=CC=1 HOLNIDQMPCIVFH-UHFFFAOYSA-N 0.000 claims description 2
- ZRUBRPSILIFDQG-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-[4-(trifluoromethyl)phenyl]benzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NC2=CC=C(C=C2)C(F)(F)F)C=CC=1 ZRUBRPSILIFDQG-UHFFFAOYSA-N 0.000 claims description 2
- OVEOBZPMHITBIB-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-[[4-(4-ethylpiperazin-1-yl)phenyl]methyl]benzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NCC2=CC=C(C=C2)N2CCN(CC2)CC)C=CC=1 OVEOBZPMHITBIB-UHFFFAOYSA-N 0.000 claims description 2
- HGMGTTVDCACMDN-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-[[4-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NCC2=CC=C(C=C2)C(F)(F)F)C=CC=1 HGMGTTVDCACMDN-UHFFFAOYSA-N 0.000 claims description 2
- FQVUWJYJPDWXIX-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-benzylbenzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NCC2=CC=CC=C2)C=CC=1 FQVUWJYJPDWXIX-UHFFFAOYSA-N 0.000 claims description 2
- HWQXLDSAJUNZAU-UHFFFAOYSA-N 3-[4-(aminomethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HWQXLDSAJUNZAU-UHFFFAOYSA-N 0.000 claims description 2
- OQYGDEPLJLNFQD-UHFFFAOYSA-N 3-[[3-[4-(aminomethyl)pyridin-2-yl]oxybenzoyl]amino]benzoic acid Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NC=2C=C(C(=O)O)C=CC=2)C=CC=1 OQYGDEPLJLNFQD-UHFFFAOYSA-N 0.000 claims description 2
- KNHQKWFHWLBNHO-UHFFFAOYSA-N 3-[[4-(aminomethyl)pyridin-2-yl]oxymethyl]-N-phenylbenzamide Chemical compound NCC1=CC(=NC=C1)OCC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 KNHQKWFHWLBNHO-UHFFFAOYSA-N 0.000 claims description 2
- TXWRMUOPZRZXAR-UHFFFAOYSA-N 3-[[[3-[4-(aminomethyl)pyridin-2-yl]oxybenzoyl]amino]methyl]benzoic acid Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NCC=2C=C(C(=O)O)C=CC=2)C=CC=1 TXWRMUOPZRZXAR-UHFFFAOYSA-N 0.000 claims description 2
- UCWMLEPMQKZORS-UHFFFAOYSA-N 4-[4-(aminomethyl)pyridin-2-yl]-N-(2-methoxyethyl)benzamide Chemical compound NCC1=CC(=NC=C1)C1=CC=C(C(=O)NCCOC)C=C1 UCWMLEPMQKZORS-UHFFFAOYSA-N 0.000 claims description 2
- DXQWWEUVIGNTOY-UHFFFAOYSA-N 4-[4-(aminomethyl)pyridin-2-yl]-N-benzylbenzamide Chemical compound NCC1=CC(=NC=C1)C1=CC=C(C(=O)NCC2=CC=CC=C2)C=C1 DXQWWEUVIGNTOY-UHFFFAOYSA-N 0.000 claims description 2
- HOUYIBMMOZYANR-UHFFFAOYSA-N 4-[4-(aminomethyl)pyridin-2-yl]oxy-N-(2-methoxyethyl)benzamide Chemical compound NCC1=CC(=NC=C1)OC1=CC=C(C(=O)NCCOC)C=C1 HOUYIBMMOZYANR-UHFFFAOYSA-N 0.000 claims description 2
- PVUHBMXOIZKNHK-UHFFFAOYSA-N 4-[4-(aminomethyl)pyridin-2-yl]oxy-N-benzylbenzamide Chemical compound NCC1=CC(=NC=C1)OC1=CC=C(C(=O)NCC2=CC=CC=C2)C=C1 PVUHBMXOIZKNHK-UHFFFAOYSA-N 0.000 claims description 2
- MMVQJHXOWFTQPV-UHFFFAOYSA-N 4-[4-(aminomethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC=C1)OC1=CC=C(C(=O)NC2=CC=CC=C2)C=C1 MMVQJHXOWFTQPV-UHFFFAOYSA-N 0.000 claims description 2
- ICUFXLHEFRTNQM-UHFFFAOYSA-N 4-[[3-[4-(aminomethyl)pyridin-2-yl]oxybenzoyl]amino]benzoic acid Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NC2=CC=C(C(=O)O)C=C2)C=CC=1 ICUFXLHEFRTNQM-UHFFFAOYSA-N 0.000 claims description 2
- XQFUMTQVTHNHFH-UHFFFAOYSA-N 4-[[[3-[4-(aminomethyl)pyridin-2-yl]oxybenzoyl]amino]methyl]benzoic acid Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NCC2=CC=C(C(=O)O)C=C2)C=CC=1 XQFUMTQVTHNHFH-UHFFFAOYSA-N 0.000 claims description 2
- MAPGRQSVGRBDGP-UHFFFAOYSA-N [3-[4-(aminomethyl)pyridin-2-yl]oxyphenyl]-(3,4-dihydro-1H-isoquinolin-2-yl)methanone Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C=CC=1)C(=O)N1CC2=CC=CC=C2CC1 MAPGRQSVGRBDGP-UHFFFAOYSA-N 0.000 claims description 2
- SKHNNUXTQYYXJG-UHFFFAOYSA-N ethyl 3-[[3-[4-(aminomethyl)pyridin-2-yl]oxybenzoyl]amino]benzoate Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NC=2C=C(C(=O)OCC)C=CC=2)C=CC=1 SKHNNUXTQYYXJG-UHFFFAOYSA-N 0.000 claims description 2
- RSIVXCHSEZQCQY-UHFFFAOYSA-N methyl 4-[[[3-[4-(aminomethyl)pyridin-2-yl]oxybenzoyl]amino]methyl]benzoate Chemical compound NCC1=CC(=NC=C1)OC=1C=C(C(=O)NCC2=CC=C(C(=O)OC)C=C2)C=CC=1 RSIVXCHSEZQCQY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 7
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 6
- 125000002619 bicyclic group Chemical group 0.000 claims 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 125000006747 (C2-C10) heterocycloalkyl group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 229910052805 deuterium Inorganic materials 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000003161 (C1-C6) alkylene 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
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 1
- GFYVLORSTQYVPF-UHFFFAOYSA-N 4-[4-(aminomethyl)pyridin-2-yl]oxy-N-phenylindole-1-carboxamide Chemical compound NCC1=CC(=NC=C1)OC1=C2C=CN(C2=CC=C1)C(=O)NC1=CC=CC=C1 GFYVLORSTQYVPF-UHFFFAOYSA-N 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- KGUABBMSFFEWGS-UHFFFAOYSA-N [4-[4-(aminomethyl)pyridin-2-yl]oxyindol-1-yl]-phenylmethanone Chemical compound NCC1=CC(=NC=C1)OC1=C2C=CN(C2=CC=C1)C(=O)C1=CC=CC=C1 KGUABBMSFFEWGS-UHFFFAOYSA-N 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000004069 aziridinyl group Chemical group 0.000 claims 1
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- SONNQRNOTIAJDS-GFCCVEGCSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[(2R)-2,3-dihydroxypropyl]benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC[C@H](CO)O)C=CC=1 SONNQRNOTIAJDS-GFCCVEGCSA-N 0.000 description 2
- 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 description 2
- JOSCNYCOYXTLTN-GFCCVEGCSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-[(3R)-3-(hydroxymethyl)pyrrolidin-1-yl]methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1C[C@@H](CC1)CO JOSCNYCOYXTLTN-GFCCVEGCSA-N 0.000 description 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 description 1
- ZXAQFYZQHPGMMN-BZSJEYESSA-N (3R)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylcyclohexane-1-carboxamide Chemical compound C1C[C@H](CC(C1)C(=O)NC2=CC=CC=C2)OC3=CC(=CC(=N3)C(F)(F)F)CN ZXAQFYZQHPGMMN-BZSJEYESSA-N 0.000 description 1
- ZWHOTPNCEFWATE-CQSZACIVSA-N (3R)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylpyrrolidine-1-carboxamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@H]1CN(CC1)C(=O)NC1=CC=CC=C1 ZWHOTPNCEFWATE-CQSZACIVSA-N 0.000 description 1
- ZWHOTPNCEFWATE-AWEZNQCLSA-N (3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylpyrrolidine-1-carboxamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CC1)C(=O)NC1=CC=CC=C1 ZWHOTPNCEFWATE-AWEZNQCLSA-N 0.000 description 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 description 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 description 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 description 1
- CJYDQTAWSHWBIT-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2-hydroxy-2-methylpropyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC(C)(C)O)C=CC=1 CJYDQTAWSHWBIT-UHFFFAOYSA-N 0.000 description 1
- MROVZCRMXJZHCN-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2-hydroxyethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCCO)C=CC=1 MROVZCRMXJZHCN-UHFFFAOYSA-N 0.000 description 1
- SHBHYINHXNTBRP-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2-methylsulfonylethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCCS(=O)(=O)C)C=CC=1 SHBHYINHXNTBRP-UHFFFAOYSA-N 0.000 description 1
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| PE20140146A1 (es) | 2010-11-19 | 2014-02-06 | Incyte Corp | Derivados de pirrolopiridina y pirrolopirimidina sustituidos con ciclobutilo como inhibidores de jak |
| 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 |
| JP6073343B2 (ja) | 2011-10-20 | 2017-02-01 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニーＧｌａｘｏＳｍｉｔｈＫｌｉｎｅ ＬＬＣ | サーチュイン調節因子としての置換された二環式アザ複素環およびアナログ |
| IN2014MN01982A (https=) | 2012-04-25 | 2015-07-10 | Raqualia Pharma Inc | |
| SG11201503065PA (en) | 2012-10-30 | 2015-05-28 | Gilead Sciences Inc | Therapeutic and diagnostic methods related to lysyl oxidase-like 2 (loxl2) |
| JP6301842B2 (ja) | 2012-12-18 | 2018-03-28 | Ｅａファーマ株式会社 | 複素環アミド誘導体及びそれを含有する医薬 |
| WO2016020732A1 (en) | 2014-08-05 | 2016-02-11 | The University Of British Columbia | Modulators of caspase-6 |
| JP6700291B2 (ja) | 2015-02-15 | 2020-05-27 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | １−（ｈｅｔ）アリールスルホニル−（ピロリジン又はピペリジン）−２−カルボキサミド誘導体、及びｔｒｐａ１拮抗薬としてのそれらの使用 |
| EP3265445B1 (en) | 2015-03-06 | 2021-05-05 | Pharmakea, Inc. | Lysyl oxidase-like 2 inhibitors and uses thereof |
| AU2016229268B2 (en) | 2015-03-06 | 2020-09-10 | Pharmakea, Inc. | Fluorinated lysyl oxidase-like 2 inhibitors and uses thereof |
| WO2017003862A1 (en) * | 2015-07-01 | 2017-01-05 | Pharmakea, Inc. | Lysyl oxidase-like 2 inhibitors and uses thereof |
| CA3013917A1 (en) * | 2016-02-09 | 2017-08-17 | Pharmakea, Inc. | Quinolinone lysyl oxidase-like 2 inhibitors and uses thereof |
| WO2018048942A1 (en) * | 2016-09-07 | 2018-03-15 | Pharmakea, Inc. | Uses of a lysyl oxidase-like 2 inhibitor |
| CA3036064A1 (en) * | 2016-09-07 | 2018-03-15 | Pharmakea, Inc. | Crystalline forms of a lysyl oxidase-like 2 inhibitor and methods of making |
-
2016
- 2016-03-03 EP EP16762185.3A patent/EP3265445B1/en active Active
- 2016-03-03 US US15/555,785 patent/US10766860B2/en not_active Expired - Fee Related
- 2016-03-03 JP JP2017545627A patent/JP6800872B2/ja not_active Expired - Fee Related
- 2016-03-03 WO PCT/US2016/020731 patent/WO2016144702A1/en not_active Ceased
- 2016-03-03 CN CN201680026238.9A patent/CN107624110B/zh not_active Expired - Fee Related
- 2016-03-03 ES ES16762185T patent/ES2872553T3/es active Active
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2020
- 2020-07-17 US US16/932,617 patent/US11358936B2/en active Active
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