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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2016
- 2016-03-03 WO PCT/US2016/020731 patent/WO2016144702A1/en not_active Ceased
- 2016-03-03 ES ES16762185T patent/ES2872553T3/es active Active
- 2016-03-03 JP JP2017545627A patent/JP6800872B2/ja not_active Expired - Fee Related
- 2016-03-03 US US15/555,785 patent/US10766860B2/en not_active Expired - Fee Related
- 2016-03-03 EP EP16762185.3A patent/EP3265445B1/en active Active
- 2016-03-03 CN CN201680026238.9A patent/CN107624110B/zh not_active Expired - Fee Related
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2020
- 2020-07-17 US US16/932,617 patent/US11358936B2/en active Active
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