JP2020516671A5

JP2020516671A5 -

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Publication number: JP2020516671A5
Authority: JP; Japan
Prior art keywords: methyl; compound; acid; triazole; sulfanyl
Prior art date: 2018-04-12
Legal status : Granted

Application number

JP2019556238A

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English (en)

Japanese (ja)

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JP7241025B2 (ja

JP2020516671A (ja

Filing date

2018-04-12

Publication date

2020-12-17

2017-04-14 Priority claimed from IT102017000041723A external-priority patent/IT201700041723A1/it

2018-04-12 Application filed filed Critical

2020-06-11 Publication of JP2020516671A publication Critical patent/JP2020516671A/ja

2020-12-17 Publication of JP2020516671A5 publication Critical patent/JP2020516671A5/ja

2022-10-13 Priority to JP2022164773A priority Critical patent/JP2022191395A/ja

2023-03-16 Application granted granted Critical

2023-03-16 Publication of JP7241025B2 publication Critical patent/JP7241025B2/ja

Status Active legal-status Critical Current

2038-04-12 Anticipated expiration legal-status Critical

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150000001875 compounds Chemical class 0.000 claims 129
-1 3- (diethylamino) propyl Chemical group 0.000 claims 48
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 33
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
125000003396 thiol group Chemical group [H]S* 0.000 claims 10
VDEUYMSGMPQMIK-UHFFFAOYSA-N benzhydroxamic acid Chemical compound ONC(=O)C1=CC=CC=C1 VDEUYMSGMPQMIK-UHFFFAOYSA-N 0.000 claims 9
239000002253 acid Substances 0.000 claims 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
229910052739 hydrogen Inorganic materials 0.000 claims 5
229910052760 oxygen Inorganic materials 0.000 claims 5
239000008194 pharmaceutical composition Substances 0.000 claims 5
VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 claims 4
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
125000000217 alkyl group Chemical group 0.000 claims 4
229910052799 carbon Inorganic materials 0.000 claims 4
229910052717 sulfur Inorganic materials 0.000 claims 4
125000004432 carbon atom Chemical group C* 0.000 claims 3
125000000753 cycloalkyl group Chemical group 0.000 claims 3
229910052736 halogen Inorganic materials 0.000 claims 3
229910052757 nitrogen Inorganic materials 0.000 claims 3
125000006516 2-(benzyloxy)ethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 2
GMZWCDSFCCBBAI-UHFFFAOYSA-N 4-[[5-(2-fluorophenyl)tetrazol-2-yl]methyl]-N-hydroxybenzamide Chemical compound FC1=C(C=CC=C1)C=1N=NN(N=1)CC1=CC=C(C=C1)C(=O)NO GMZWCDSFCCBBAI-UHFFFAOYSA-N 0.000 claims 2
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 2
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 2
229940076838 Immune checkpoint inhibitor Drugs 0.000 claims 2
125000003545 alkoxy group Chemical group 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 claims 2
125000004122 cyclic group Chemical group 0.000 claims 2
125000004981 cycloalkylmethyl group Chemical group 0.000 claims 2
125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims 2
201000010099 disease Diseases 0.000 claims 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
239000003814 drug Substances 0.000 claims 2
229940079593 drug Drugs 0.000 claims 2
125000005843 halogen group Chemical group 0.000 claims 2
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 2
125000001072 heteroaryl group Chemical group 0.000 claims 2
125000005842 heteroatom Chemical group 0.000 claims 2
239000012274 immune-checkpoint protein inhibitor Substances 0.000 claims 2
239000003112 inhibitor Substances 0.000 claims 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
229940002612 prodrug Drugs 0.000 claims 2
239000000651 prodrug Substances 0.000 claims 2
125000004076 pyridyl group Chemical group 0.000 claims 2
SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical group C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 claims 2
150000003839 salts Chemical class 0.000 claims 2
229930192474 thiophene Chemical group 0.000 claims 2
125000003944 tolyl group Chemical group 0.000 claims 2
ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 claims 1
UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 claims 1
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims 1
GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims 1
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims 1
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims 1
GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 claims 1
IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 claims 1
YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 claims 1
VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 claims 1
ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 claims 1
STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 claims 1
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 claims 1
UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 claims 1
OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 claims 1
MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 claims 1
YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 claims 1
OIIOPWHTJZYKIL-PMACEKPBSA-N (5S)-5-[[[5-[2-chloro-3-[2-chloro-3-[6-methoxy-5-[[[(2S)-5-oxopyrrolidin-2-yl]methylamino]methyl]pyrazin-2-yl]phenyl]phenyl]-3-methoxypyrazin-2-yl]methylamino]methyl]pyrrolidin-2-one Chemical compound C1(=C(N=C(C2=C(C(C3=CC=CC(=C3Cl)C3=NC(OC)=C(N=C3)CNC[C@H]3NC(=O)CC3)=CC=C2)Cl)C=N1)OC)CNC[C@H]1NC(=O)CC1 OIIOPWHTJZYKIL-PMACEKPBSA-N 0.000 claims 1
IOQORVDNYPOZPL-VQTJNVASSA-N (5S,6R)-5-(4-chlorophenyl)-6-cyclopropyl-3-[6-methoxy-5-(4-methylimidazol-1-yl)pyridin-2-yl]-5,6-dihydro-2H-1,2,4-oxadiazine Chemical compound ClC1=CC=C(C=C1)[C@@H]1NC(=NO[C@@H]1C1CC1)C1=NC(=C(C=C1)N1C=NC(=C1)C)OC IOQORVDNYPOZPL-VQTJNVASSA-N 0.000 claims 1
VUEGYUOUAAVYAS-JGGQBBKZSA-N (6ar,9s,10ar)-9-(dimethylsulfamoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CNC3=C1 VUEGYUOUAAVYAS-JGGQBBKZSA-N 0.000 claims 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
ZYZCALPXKGUGJI-DDVDASKDSA-M (e,3r,5s)-7-[3-(4-fluorophenyl)-2-phenyl-5-propan-2-ylimidazol-4-yl]-3,5-dihydroxyhept-6-enoate Chemical compound C=1C=C(F)C=CC=1N1C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C(C)C)N=C1C1=CC=CC=C1 ZYZCALPXKGUGJI-DDVDASKDSA-M 0.000 claims 1
DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 claims 1
FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical group C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims 1
FZQXMGLQANXZRP-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-(3-imidazol-1-ylpropyl)thiourea Chemical compound C1=C(OC)C(OC)=CC=C1NC(=S)NCCCN1C=NC=C1 FZQXMGLQANXZRP-UHFFFAOYSA-N 0.000 claims 1
MHSLDASSAFCCDO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 MHSLDASSAFCCDO-UHFFFAOYSA-N 0.000 claims 1
KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 claims 1
WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 claims 1
ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 claims 1
UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 claims 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 claims 1
FQMZXMVHHKXGTM-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(2-hydroxyethylamino)ethylamino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCNCCO)=CC=C21 FQMZXMVHHKXGTM-UHFFFAOYSA-N 0.000 claims 1
VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 claims 1
QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 claims 1
125000000134 2-(methylsulfanyl)ethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])[*] 0.000 claims 1
QTMAZYGAVHCKKX-UHFFFAOYSA-N 2-[(4-amino-5-bromopyrrolo[2,3-d]pyrimidin-7-yl)methoxy]propane-1,3-diol Chemical compound NC1=NC=NC2=C1C(Br)=CN2COC(CO)CO QTMAZYGAVHCKKX-UHFFFAOYSA-N 0.000 claims 1
PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 claims 1
FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 claims 1
PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 claims 1
VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 claims 1
YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 claims 1
TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 claims 1
NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 claims 1
LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 claims 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical group CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 claims 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
MDRPNGAGPUOFPA-UHFFFAOYSA-N 3,5-difluoro-4-[[4-(4-fluorophenyl)-5-(piperidin-1-ylmethyl)-1,2,4-triazol-3-yl]sulfanyl]-N-hydroxybenzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C1=CC=C(C=C1)F)CN1CCCCC1)F)C(=O)NO MDRPNGAGPUOFPA-UHFFFAOYSA-N 0.000 claims 1
VRDGWNVYPNEZML-UHFFFAOYSA-N 3,5-difluoro-4-[[4-(furan-2-ylmethyl)-5-pyridin-3-yl-1,2,4-triazol-3-yl]sulfanyl]-N-hydroxybenzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1CC=1OC=CC=1)C=1C=NC=CC=1)F)C(=O)NO VRDGWNVYPNEZML-UHFFFAOYSA-N 0.000 claims 1
RHZJAJYSZPVEIW-UHFFFAOYSA-N 3,5-difluoro-4-[[4-(furan-2-ylmethyl)-5-pyrrolidin-1-yl-1,2,4-triazol-3-yl]sulfanyl]-N-hydroxybenzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1CC=1OC=CC=1)N1CCCC1)F)C(=O)NO RHZJAJYSZPVEIW-UHFFFAOYSA-N 0.000 claims 1
YOIHDAPDYCUJHM-UHFFFAOYSA-N 3,5-difluoro-4-[[5-(2-fluorophenyl)-4-(furan-2-ylmethyl)-1,2,4-triazol-3-yl]sulfanyl]-N-hydroxybenzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1CC=1OC=CC=1)C1=C(C=CC=C1)F)F)C(=O)NO YOIHDAPDYCUJHM-UHFFFAOYSA-N 0.000 claims 1
XRAYCVXGTQBWKM-UHFFFAOYSA-N 3,5-difluoro-4-[[5-(4-fluorophenyl)-4-(2-morpholin-4-ylethyl)-1,2,4-triazol-3-yl]sulfanyl]-N-hydroxybenzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1CCN1CCOCC1)C1=CC=C(C=C1)F)F)C(=O)NO XRAYCVXGTQBWKM-UHFFFAOYSA-N 0.000 claims 1
UBDPSCAYEZDVAG-UHFFFAOYSA-N 3,5-difluoro-4-[[5-(furan-2-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]-N-hydroxybenzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C)C=1OC=CC=1)F)C(=O)NO UBDPSCAYEZDVAG-UHFFFAOYSA-N 0.000 claims 1
QBHMLIUTCIQHKA-UHFFFAOYSA-N 3,5-difluoro-4-[[5-(furan-2-yl)tetrazol-1-yl]methyl]-N-hydroxybenzamide Chemical compound FC=1C=C(C=C(C=1CN1N=NN=C1C=1OC=CC=1)F)C(=O)NO QBHMLIUTCIQHKA-UHFFFAOYSA-N 0.000 claims 1
KVIGMGRUSRSDGB-UHFFFAOYSA-N 3,5-difluoro-4-[[5-(furan-2-yl)tetrazol-2-yl]methyl]-N-hydroxybenzamide Chemical compound FC=1C=C(C(=O)NO)C=C(C=1CN1N=C(N=N1)C=1OC=CC=1)F KVIGMGRUSRSDGB-UHFFFAOYSA-N 0.000 claims 1
UGUDMXQVODIFJW-UHFFFAOYSA-N 3,5-difluoro-4-[[5-[1-(3-fluorophenyl)cyclopentyl]-4-methyl-1,2,4-triazol-3-yl]sulfanyl]-N-hydroxybenzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C)C1(CCCC1)C1=CC(=CC=C1)F)F)C(=O)NO UGUDMXQVODIFJW-UHFFFAOYSA-N 0.000 claims 1
CJGRKGSKAKFUNC-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[(4-methyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C)C=1C=NC=CC=1)F)C(=O)NO CJGRKGSKAKFUNC-UHFFFAOYSA-N 0.000 claims 1
PKFOLSOUZPYTPC-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[(5-isoquinolin-1-yltetrazol-1-yl)methyl]benzamide Chemical compound FC=1C=C(C=C(C=1CN1N=NN=C1C1=NC=CC2=CC=CC=C12)F)C(=O)NO PKFOLSOUZPYTPC-UHFFFAOYSA-N 0.000 claims 1
MCQKRHGWAAJJEJ-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[(5-isoquinolin-1-yltetrazol-2-yl)methyl]benzamide Chemical compound FC=1C=C(C=C(C=1CN1N=C(N=N1)C1=NC=CC2=CC=CC=C12)F)C(=O)NO MCQKRHGWAAJJEJ-UHFFFAOYSA-N 0.000 claims 1
UYCATXNNQQDGPV-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC=1OC(=NN=1)C1=CC=CC=C1)F)C(=O)NO UYCATXNNQQDGPV-UHFFFAOYSA-N 0.000 claims 1
OJELVCJPFBYLMH-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[(5-pyrimidin-2-yltetrazol-1-yl)methyl]benzamide Chemical compound FC=1C=C(C=C(C=1CN1N=NN=C1C1=NC=CC=N1)F)C(=O)NO OJELVCJPFBYLMH-UHFFFAOYSA-N 0.000 claims 1
ZSCIHQFQADRGED-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[(5-quinolin-2-yltetrazol-1-yl)methyl]benzamide Chemical compound FC=1C=C(C=C(C=1CN1N=NN=C1C1=NC2=CC=CC=C2C=C1)F)C(=O)NO ZSCIHQFQADRGED-UHFFFAOYSA-N 0.000 claims 1
WXGQBLNIJTZXJM-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[(5-quinolin-2-yltetrazol-2-yl)methyl]benzamide Chemical compound FC=1C=C(C=C(C=1CN1N=C(N=N1)C1=NC2=CC=CC=C2C=C1)F)C(=O)NO WXGQBLNIJTZXJM-UHFFFAOYSA-N 0.000 claims 1
YSEBLHGDHUUXHS-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[(5-thiophen-2-yl-1H-1,2,4-triazol-3-yl)sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1)C=1SC=CC=1)F)C(=O)NO YSEBLHGDHUUXHS-UHFFFAOYSA-N 0.000 claims 1
JWDMKAQBWAPIKN-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[(5-thiophen-2-yltetrazol-2-yl)methyl]benzamide Chemical compound FC=1C=C(C=C(C=1CN1N=C(N=N1)C=1SC=CC=1)F)C(=O)NO JWDMKAQBWAPIKN-UHFFFAOYSA-N 0.000 claims 1
YIJBXZDUOXPQPK-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[4-methyl-5-(1-phenylcyclobutyl)-1,2,4-triazol-3-yl]sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C)C1(CCC1)C1=CC=CC=C1)F)C(=O)NO YIJBXZDUOXPQPK-UHFFFAOYSA-N 0.000 claims 1
QUIFKTZMXAZFEO-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[4-methyl-5-(1-pyridin-2-ylcyclopropyl)-1,2,4-triazol-3-yl]sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C)C1(CC1)C1=NC=CC=C1)F)C(=O)NO QUIFKTZMXAZFEO-UHFFFAOYSA-N 0.000 claims 1
VDKGWVJGSMPFAP-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[4-methyl-5-(1-pyridin-3-ylcyclopropyl)-1,2,4-triazol-3-yl]sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C)C1(CC1)C=1C=NC=CC=1)F)C(=O)NO VDKGWVJGSMPFAP-UHFFFAOYSA-N 0.000 claims 1
TZWZUMKATWENRF-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[4-methyl-5-(2-pyridin-3-ylpropan-2-yl)-1,2,4-triazol-3-yl]sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C)C(C)(C=1C=NC=CC=1)C)F)C(=O)NO TZWZUMKATWENRF-UHFFFAOYSA-N 0.000 claims 1
SQNZQNAKNNZPAU-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[4-methyl-5-(quinolin-8-ylmethyl)-1,2,4-triazol-3-yl]sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C)CC=1C=CC=C2C=CC=NC=12)F)C(=O)NO SQNZQNAKNNZPAU-UHFFFAOYSA-N 0.000 claims 1
SBFADQWXHBTXKP-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[4-methyl-5-[3-(4-methylpiperazin-1-yl)phenyl]-1,2,4-triazol-3-yl]sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C)C1=CC(=CC=C1)N1CCN(CC1)C)F)C(=O)NO SBFADQWXHBTXKP-UHFFFAOYSA-N 0.000 claims 1
TVVDSGKQYWUWOY-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[4-methyl-5-[3-(4-methylpiperazin-1-yl)sulfonylphenyl]-1,2,4-triazol-3-yl]sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C)C1=CC(=CC=C1)S(=O)(=O)N1CCN(CC1)C)F)C(=O)NO TVVDSGKQYWUWOY-UHFFFAOYSA-N 0.000 claims 1
ISIHLVRMOJXWBE-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[4-methyl-5-[3-(morpholin-4-ylmethyl)phenyl]-1,2,4-triazol-3-yl]sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C)C1=CC(=CC=C1)CN1CCOCC1)F)C(=O)NO ISIHLVRMOJXWBE-UHFFFAOYSA-N 0.000 claims 1
NBUAJLZAQVKMIK-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[4-methyl-5-[3-(piperidin-1-ylmethyl)phenyl]-1,2,4-triazol-3-yl]sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C)C1=CC(=CC=C1)CN1CCCCC1)F)C(=O)NO NBUAJLZAQVKMIK-UHFFFAOYSA-N 0.000 claims 1
UTUAWSCNKHKUFP-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[4-methyl-5-[5-(morpholin-4-ylmethyl)furan-2-yl]-1,2,4-triazol-3-yl]sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C)C=1OC(=CC=1)CN1CCOCC1)F)C(=O)NO UTUAWSCNKHKUFP-UHFFFAOYSA-N 0.000 claims 1
XUZJZJHLHYMFGX-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[4-methyl-5-[5-(morpholin-4-ylmethyl)furan-3-yl]-1,2,4-triazol-3-yl]sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C)C1=COC(=C1)CN1CCOCC1)F)C(=O)NO XUZJZJHLHYMFGX-UHFFFAOYSA-N 0.000 claims 1
XGZMXWGZWLKVOZ-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[4-methyl-5-[5-(piperidin-1-ylmethyl)furan-2-yl]-1,2,4-triazol-3-yl]sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C)C=1OC(=CC=1)CN1CCCCC1)F)C(=O)NO XGZMXWGZWLKVOZ-UHFFFAOYSA-N 0.000 claims 1
MMPYKZTWJVMXFU-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[4-methyl-5-[5-(pyrrolidin-1-ylmethyl)furan-2-yl]-1,2,4-triazol-3-yl]sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C)C=1OC(=CC=1)CN1CCCC1)F)C(=O)NO MMPYKZTWJVMXFU-UHFFFAOYSA-N 0.000 claims 1
YAEJKUQRIZKKPN-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[4-methyl-5-[5-[(4-methylpiperazin-1-yl)methyl]furan-2-yl]-1,2,4-triazol-3-yl]sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C)C=1OC(=CC=1)CN1CCN(CC1)C)F)C(=O)NO YAEJKUQRIZKKPN-UHFFFAOYSA-N 0.000 claims 1
IQDIFZUHWJSIJK-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[4-methyl-5-[6-(2-pyrrolidin-1-ylethyl)pyridin-3-yl]-1,2,4-triazol-3-yl]sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C)C=1C=NC(=CC=1)CCN1CCCC1)F)C(=O)NO IQDIFZUHWJSIJK-UHFFFAOYSA-N 0.000 claims 1
AQMQMNKZLYXPRG-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[5-(5-morpholin-4-ylpyridin-3-yl)-1,3,4-thiadiazol-2-yl]methyl]benzamide Chemical compound FC=1C=C(C=C(C=1CC=1SC(=NN=1)C=1C=NC=C(C=1)N1CCOCC1)F)C(=O)NO AQMQMNKZLYXPRG-UHFFFAOYSA-N 0.000 claims 1
KZXLLMSNNWGSAH-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[5-(pyridin-2-ylmethyl)tetrazol-1-yl]methyl]benzamide Chemical compound FC=1C=C(C=C(C=1CN1N=NN=C1CC1=NC=CC=C1)F)C(=O)NO KZXLLMSNNWGSAH-UHFFFAOYSA-N 0.000 claims 1
RDELMWQNFVZMTE-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[5-(pyridin-2-ylmethyl)tetrazol-2-yl]methyl]benzamide Chemical compound FC=1C=C(C=C(C=1CN1N=C(N=N1)CC1=NC=CC=C1)F)C(=O)NO RDELMWQNFVZMTE-UHFFFAOYSA-N 0.000 claims 1
KQMYJGXFCFBRJU-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[5-[1-(4-methoxyphenyl)cyclohexyl]-4-methyl-1,2,4-triazol-3-yl]sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C)C1(CCCCC1)C1=CC=C(C=C1)OC)F)C(=O)NO KQMYJGXFCFBRJU-UHFFFAOYSA-N 0.000 claims 1
OQYMBEMGXVJBGZ-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[5-[1-(4-methoxyphenyl)cyclopropyl]-4-methyl-1,2,4-triazol-3-yl]sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC1=NN=C(N1C)C1(CC1)C1=CC=C(C=C1)OC)F)C(=O)NO OQYMBEMGXVJBGZ-UHFFFAOYSA-N 0.000 claims 1
CHTFDUHTFXFYPY-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[5-[3-(pentafluoro-lambda6-sulfanyl)phenyl]tetrazol-1-yl]methyl]benzamide Chemical compound FC=1C=C(C=C(C=1CN1N=NN=C1C1=CC(=CC=C1)S(F)(F)(F)(F)F)F)C(=O)NO CHTFDUHTFXFYPY-UHFFFAOYSA-N 0.000 claims 1
LUUCPQYOTUFOCI-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[5-[3-(pentafluoro-lambda6-sulfanyl)phenyl]tetrazol-2-yl]methyl]benzamide Chemical compound FC=1C=C(C=C(C=1CN1N=C(N=N1)C1=CC(=CC=C1)S(F)(F)(F)(F)F)F)C(=O)NO LUUCPQYOTUFOCI-UHFFFAOYSA-N 0.000 claims 1
RCNHCCQIDIQQTQ-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[5-[4-(pentafluoro-lambda6-sulfanyl)phenyl]tetrazol-1-yl]methyl]benzamide Chemical compound FC=1C=C(C=C(C=1CN1N=NN=C1C1=CC=C(C=C1)S(F)(F)(F)(F)F)F)C(=O)NO RCNHCCQIDIQQTQ-UHFFFAOYSA-N 0.000 claims 1
RDQGHCOUPVCQFW-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[5-[4-(pentafluoro-lambda6-sulfanyl)phenyl]tetrazol-2-yl]methyl]benzamide Chemical compound FC=1C=C(C=C(C=1CN1N=C(N=N1)C1=CC=C(C=C1)S(F)(F)(F)(F)F)F)C(=O)NO RDQGHCOUPVCQFW-UHFFFAOYSA-N 0.000 claims 1
XUXWOYYRUZQHER-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[5-[4-[methyl(methylsulfonyl)amino]phenyl]-1,3,4-thiadiazol-2-yl]sulfanyl]benzamide Chemical compound FC=1C=C(C=C(C=1SC=1SC(=NN=1)C1=CC=C(C=C1)N(S(=O)(=O)C)C)F)C(=O)NO XUXWOYYRUZQHER-UHFFFAOYSA-N 0.000 claims 1
BAQYHXGCBRBPKR-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[5-[5-(pyrrolidin-1-ylmethyl)furan-2-yl]-1,2,4-oxadiazol-3-yl]methyl]benzamide Chemical compound FC=1C=C(C=C(C=1CC1=NOC(=N1)C=1OC(=CC=1)CN1CCCC1)F)C(=O)NO BAQYHXGCBRBPKR-UHFFFAOYSA-N 0.000 claims 1
ZCKCYMDWFCXIBX-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[5-[5-(trifluoromethyl)pyridin-2-yl]tetrazol-1-yl]methyl]benzamide Chemical compound FC=1C=C(C=C(C=1CN1N=NN=C1C1=NC=C(C=C1)C(F)(F)F)F)C(=O)NO ZCKCYMDWFCXIBX-UHFFFAOYSA-N 0.000 claims 1
QCJAURREOKXNGT-UHFFFAOYSA-N 3,5-difluoro-N-hydroxy-4-[[5-[5-(trifluoromethyl)pyridin-2-yl]tetrazol-2-yl]methyl]benzamide Chemical compound FC=1C=C(C=C(C=1CN1N=C(N=N1)C1=NC=C(C=C1)C(F)(F)F)F)C(=O)NO QCJAURREOKXNGT-UHFFFAOYSA-N 0.000 claims 1
DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 claims 1
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims 1
WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 claims 1
GQPAXWRYFWUOFN-UHFFFAOYSA-N 3-[2-[[4-(hydroxycarbamoyl)phenyl]methyl]tetrazol-5-yl]benzoic acid Chemical compound ONC(=O)C1=CC=C(C=C1)CN1N=C(N=N1)C=1C=C(C(=O)O)C=CC=1 GQPAXWRYFWUOFN-UHFFFAOYSA-N 0.000 claims 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
CDUYFJPDIWPQPP-UHFFFAOYSA-N 4-[(4,5-diphenyl-1,2,4-triazol-3-yl)sulfanyl]-N-hydroxybenzamide Chemical compound C1(=CC=CC=C1)N1C(=NN=C1C1=CC=CC=C1)SC1=CC=C(C=C1)C(=O)NO CDUYFJPDIWPQPP-UHFFFAOYSA-N 0.000 claims 1
OQBWJRJSJINSGX-UHFFFAOYSA-N 4-[(4-benzyl-5-morpholin-4-yl-1,2,4-triazol-3-yl)sulfanyl]-3,5-difluoro-N-hydroxybenzamide Chemical compound ONC(=O)c1cc(F)c(Sc2nnc(N3CCOCC3)n2Cc2ccccc2)c(F)c1 OQBWJRJSJINSGX-UHFFFAOYSA-N 0.000 claims 1
UCBXZMCXVQQVOJ-UHFFFAOYSA-N 4-[(4-benzyl-5-thiophen-2-yl-1,2,4-triazol-3-yl)sulfanyl]-3,5-difluoro-N-hydroxybenzamide Chemical compound C(C1=CC=CC=C1)N1C(=NN=C1C=1SC=CC=1)SC1=C(C=C(C=C1F)C(=O)NO)F UCBXZMCXVQQVOJ-UHFFFAOYSA-N 0.000 claims 1
PCYHBXKLYGHNDS-UHFFFAOYSA-N 4-[(5-benzhydryl-4-methyl-1,2,4-triazol-3-yl)sulfanyl]-3,5-difluoro-N-hydroxybenzamide Chemical compound C(C1=CC=CC=C1)(C1=CC=CC=C1)C=1N(C(=NN=1)SC1=C(C=C(C=C1F)C(=O)NO)F)C PCYHBXKLYGHNDS-UHFFFAOYSA-N 0.000 claims 1
RCGOPOWTQAZTHO-UHFFFAOYSA-N 4-[(5-benzyltetrazol-1-yl)methyl]-N-hydroxybenzamide Chemical compound C(C1=CC=CC=C1)C1=NN=NN1CC1=CC=C(C=C1)C(=O)NO RCGOPOWTQAZTHO-UHFFFAOYSA-N 0.000 claims 1
CHNIGSHQRARKPH-UHFFFAOYSA-N 4-[5-[(3,4-dimethoxyphenyl)methyl]-1,3,4-oxadiazol-2-yl]-N-hydroxybenzamide Chemical compound COC=1C=C(C=CC=1OC)CC1=NN=C(O1)C1=CC=C(C=C1)C(=O)NO CHNIGSHQRARKPH-UHFFFAOYSA-N 0.000 claims 1
WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 claims 1
MPMKMQHJHDHPBE-RUZDIDTESA-N 4-[[(2r)-1-(1-benzothiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-[(3-chlorophenyl)methyl]amino]butanoic acid Chemical compound O=C([C@@]1(N(CC1)C(=O)C=1C2=CC=CC=C2SC=1)C)N(CCCC(O)=O)CC1=CC=CC(Cl)=C1 MPMKMQHJHDHPBE-RUZDIDTESA-N 0.000 claims 1
LUSBUCOMWZUIOP-UHFFFAOYSA-N 4-[[1-[[2,6-difluoro-4-(hydroxycarbamoyl)phenyl]methyl]tetrazol-5-yl]methyl]benzoic acid Chemical compound FC1=C(C(=CC(=C1)C(NO)=O)F)CN1N=NN=C1CC1=CC=C(C(=O)O)C=C1 LUSBUCOMWZUIOP-UHFFFAOYSA-N 0.000 claims 1
QAIDGUBGLMYNFX-UHFFFAOYSA-N 4-[[1-[[4-(hydroxycarbamoyl)phenyl]methyl]tetrazol-5-yl]methyl]benzoic acid Chemical compound ONC(=O)C1=CC=C(C=C1)CN1N=NN=C1CC1=CC=C(C(=O)O)C=C1 QAIDGUBGLMYNFX-UHFFFAOYSA-N 0.000 claims 1
PHDIYKQYARFZSR-UHFFFAOYSA-N 4-[[2-[[2,6-difluoro-4-(hydroxycarbamoyl)phenyl]methyl]tetrazol-5-yl]methyl]benzoic acid Chemical compound FC1=C(C(=CC(=C1)C(NO)=O)F)CN1N=C(N=N1)CC1=CC=C(C(=O)O)C=C1 PHDIYKQYARFZSR-UHFFFAOYSA-N 0.000 claims 1
GRRGMIBWMGKFDF-UHFFFAOYSA-N 4-[[2-[[4-(hydroxycarbamoyl)phenyl]methyl]tetrazol-5-yl]methyl]benzoic acid Chemical compound ONC(=O)C1=CC=C(C=C1)CN1N=C(N=N1)CC1=CC=C(C(=O)O)C=C1 GRRGMIBWMGKFDF-UHFFFAOYSA-N 0.000 claims 1
YMVRSRJFUBUMLC-UHFFFAOYSA-N 4-[[2-benzyl-5-(4-chlorophenyl)-1,2,4-triazol-3-yl]methyl]-N-hydroxybenzamide Chemical compound C(C1=CC=CC=C1)N1N=C(N=C1CC1=CC=C(C=C1)C(=O)NO)C1=CC=C(C=C1)Cl YMVRSRJFUBUMLC-UHFFFAOYSA-N 0.000 claims 1
WYCMKETXPDPDDN-UHFFFAOYSA-N 4-[[3-[(3,4-dimethoxyphenyl)methyl]-5-thiophen-2-yl-1,2,4-triazol-4-yl]methyl]-N-hydroxybenzamide Chemical compound COC=1C=C(C=CC=1OC)CC1=NN=C(N1CC1=CC=C(C=C1)C(=O)NO)C=1SC=CC=1 WYCMKETXPDPDDN-UHFFFAOYSA-N 0.000 claims 1
SQFCRUKKOCFQTP-UHFFFAOYSA-N 4-[[4-amino-5-[3-(diethylsulfamoyl)phenyl]-1,2,4-triazol-3-yl]sulfanyl]-N-hydroxybenzamide Chemical compound NN1C(=NN=C1C1=CC(=CC=C1)S(N(CC)CC)(=O)=O)SC1=CC=C(C=C1)C(=O)NO SQFCRUKKOCFQTP-UHFFFAOYSA-N 0.000 claims 1
MWYSXGSBUCIMQO-UHFFFAOYSA-N 4-[[4-amino-5-[4-(difluoromethoxy)phenyl]-1,2,4-triazol-3-yl]sulfanyl]-N-hydroxybenzamide Chemical compound NN1C(=NN=C1C1=CC=C(C=C1)OC(F)F)SC1=CC=C(C=C1)C(=O)NO MWYSXGSBUCIMQO-UHFFFAOYSA-N 0.000 claims 1
OPNLIJDFJBQDFQ-UHFFFAOYSA-N 4-[[4-benzyl-5-(furan-2-yl)-1,2,4-triazol-3-yl]sulfanyl]-3,5-difluoro-N-hydroxybenzamide Chemical compound C(C1=CC=CC=C1)N1C(=NN=C1C=1OC=CC=1)SC1=C(C=C(C=C1F)C(=O)NO)F OPNLIJDFJBQDFQ-UHFFFAOYSA-N 0.000 claims 1
SLXZFQZPDDBHRK-UHFFFAOYSA-N 4-[[4-benzyl-5-(pyrrolidin-1-ylmethyl)-1,2,4-triazol-3-yl]sulfanyl]-3,5-difluoro-N-hydroxybenzamide Chemical compound ONC(=O)c1cc(F)c(Sc2nnc(CN3CCCC3)n2Cc2ccccc2)c(F)c1 SLXZFQZPDDBHRK-UHFFFAOYSA-N 0.000 claims 1
JXAGTYCOYIZUGQ-UHFFFAOYSA-N 4-[[4-ethyl-5-(4-fluorophenyl)-1,2,4-triazol-3-yl]sulfanyl]-N-hydroxybenzamide Chemical compound C(C)N1C(=NN=C1C1=CC=C(C=C1)F)SC1=CC=C(C=C1)C(=O)NO JXAGTYCOYIZUGQ-UHFFFAOYSA-N 0.000 claims 1
QUQUSDQDAPUQID-UHFFFAOYSA-N 4-[[5-(1,3-benzodioxol-5-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]-N-hydroxybenzamide Chemical compound O1COC2=C1C=CC(=C2)C=1N(C(=NN=1)SC1=CC=C(C=C1)C(=O)NO)C QUQUSDQDAPUQID-UHFFFAOYSA-N 0.000 claims 1
VWTLMTSFZGOVNA-UHFFFAOYSA-N 4-[[5-(1-benzothiophen-2-yl)tetrazol-2-yl]methyl]-N-hydroxybenzamide Chemical compound S1C(=CC2=C1C=CC=C2)C=1N=NN(N=1)CC1=CC=C(C=C1)C(=O)NO VWTLMTSFZGOVNA-UHFFFAOYSA-N 0.000 claims 1
HRHPYDMAIAATJY-UHFFFAOYSA-N 4-[[5-(1-benzothiophen-3-yl)tetrazol-2-yl]methyl]-N-hydroxybenzamide Chemical compound S1C=C(C2=C1C=CC=C2)C=1N=NN(N=1)CC1=CC=C(C=C1)C(=O)NO HRHPYDMAIAATJY-UHFFFAOYSA-N 0.000 claims 1
FIMNANSLMVIHGY-UHFFFAOYSA-N 4-[[5-(1-benzyl-4-phenylpiperidin-4-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]-3,5-difluoro-N-hydroxybenzamide Chemical compound Cn1c(Sc2c(F)cc(cc2F)C(=O)NO)nnc1C1(CCN(Cc2ccccc2)CC1)c1ccccc1 FIMNANSLMVIHGY-UHFFFAOYSA-N 0.000 claims 1
WINVBIJCUQMCMZ-UHFFFAOYSA-N 4-[[5-(2,3-dihydro-1,4-benzodioxin-3-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]-N-hydroxybenzamide Chemical compound O1CC(OC2=C1C=CC=C2)C=1N(C(=NN=1)SC1=CC=C(C=C1)C(=O)NO)C WINVBIJCUQMCMZ-UHFFFAOYSA-N 0.000 claims 1
DEFQPMMOLPOQPB-UHFFFAOYSA-N 4-[[5-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-4-methyl-1,2,4-triazol-3-yl]sulfanyl]-3,5-difluoro-N-hydroxybenzamide Chemical compound Cn1c(Sc2c(F)cc(cc2F)C(=O)NO)nnc1-c1scc2OCCOc12 DEFQPMMOLPOQPB-UHFFFAOYSA-N 0.000 claims 1
QXIXPEHSCYDHRP-UHFFFAOYSA-N 4-[[5-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)tetrazol-1-yl]methyl]-3,5-difluoro-N-hydroxybenzamide Chemical compound O1C=2C(OCC1)=C(SC=2)C1=NN=NN1CC1=C(C=C(C(=O)NO)C=C1F)F QXIXPEHSCYDHRP-UHFFFAOYSA-N 0.000 claims 1
KWQUDGCDOJCMQM-UHFFFAOYSA-N 4-[[5-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)tetrazol-2-yl]methyl]-N-hydroxybenzamide Chemical compound O1C=2C(OCC1)=C(SC=2)C=1N=NN(N=1)CC1=CC=C(C=C1)C(=O)NO KWQUDGCDOJCMQM-UHFFFAOYSA-N 0.000 claims 1
MHFFHARKVRZCBY-UHFFFAOYSA-N 4-[[5-(2,4-dichlorophenyl)tetrazol-2-yl]methyl]-N-hydroxybenzamide Chemical compound ClC1=C(C=CC(=C1)Cl)C=1N=NN(N=1)CC1=CC=C(C=C1)C(=O)NO MHFFHARKVRZCBY-UHFFFAOYSA-N 0.000 claims 1
ZHWRXLIMCXWAPA-UHFFFAOYSA-N 4-[[5-(2,4-difluorophenyl)-1,3,4-oxadiazol-2-yl]methyl]-N-hydroxybenzamide Chemical compound FC1=C(C=CC(=C1)F)C1=NN=C(O1)CC1=CC=C(C=C1)C(=O)NO ZHWRXLIMCXWAPA-UHFFFAOYSA-N 0.000 claims 1
YKVDSYRMMKFAHY-UHFFFAOYSA-N 4-[[5-(3,4-dimethoxyphenyl)-1,2,4-oxadiazol-3-yl]methyl]-N-hydroxybenzamide Chemical compound COC=1C=C(C=CC=1OC)C1=NC(=NO1)CC1=CC=C(C=C1)C(=O)NO YKVDSYRMMKFAHY-UHFFFAOYSA-N 0.000 claims 1
WKCCDZMYDVMVHJ-UHFFFAOYSA-N 4-[[5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl]-N-hydroxybenzamide Chemical compound COC=1C=C(C=CC=1OC)C1=NN=C(O1)CC1=CC=C(C=C1)C(=O)NO WKCCDZMYDVMVHJ-UHFFFAOYSA-N 0.000 claims 1
DOLHDROPQIUIBW-UHFFFAOYSA-N 4-[[5-(4-aminophenyl)tetrazol-1-yl]methyl]-3,5-difluoro-N-hydroxybenzamide Chemical compound Nc1ccc(cc1)-c1nnnn1Cc1c(F)cc(cc1F)C(=O)NO DOLHDROPQIUIBW-UHFFFAOYSA-N 0.000 claims 1
XBXTYIIDMXYZQN-UHFFFAOYSA-N 4-[[5-(4-aminophenyl)tetrazol-1-yl]methyl]-N-hydroxybenzamide Chemical compound NC1=CC=C(C=C1)C1=NN=NN1CC1=CC=C(C=C1)C(=O)NO XBXTYIIDMXYZQN-UHFFFAOYSA-N 0.000 claims 1
LHBOAIADGXZNHD-UHFFFAOYSA-N 4-[[5-(4-aminophenyl)tetrazol-2-yl]methyl]-3,5-difluoro-N-hydroxybenzamide Chemical compound Nc1ccc(cc1)-c1nnn(Cc2c(F)cc(cc2F)C(=O)NO)n1 LHBOAIADGXZNHD-UHFFFAOYSA-N 0.000 claims 1
WXNCLPGZPAFVKD-UHFFFAOYSA-N 4-[[5-(4-aminophenyl)tetrazol-2-yl]methyl]-N-hydroxybenzamide Chemical compound NC1=CC=C(C=C1)C=1N=NN(N=1)CC1=CC=C(C=C1)C(=O)NO WXNCLPGZPAFVKD-UHFFFAOYSA-N 0.000 claims 1
LPUNNRMWGSBZMU-UHFFFAOYSA-N 4-[[5-(4-chlorophenyl)tetrazol-2-yl]methyl]-N-hydroxybenzamide Chemical compound ClC1=CC=C(C=C1)C=1N=NN(N=1)CC1=CC=C(C=C1)C(=O)NO LPUNNRMWGSBZMU-UHFFFAOYSA-N 0.000 claims 1
NXKUCAYUQKFPGR-UHFFFAOYSA-N 4-[[5-(4-fluorophenyl)-1H-1,2,4-triazol-3-yl]sulfanyl]-N-hydroxybenzamide Chemical compound FC1=CC=C(C=C1)C=1NC(=NN=1)SC1=CC=C(C=C1)C(=O)NO NXKUCAYUQKFPGR-UHFFFAOYSA-N 0.000 claims 1
IRZGFXCJBZBORR-UHFFFAOYSA-N 4-[[5-(4-fluorophenyl)tetrazol-2-yl]methyl]-N-hydroxybenzamide Chemical compound FC1=CC=C(C=C1)C=1N=NN(N=1)CC1=CC=C(C=C1)C(=O)NO IRZGFXCJBZBORR-UHFFFAOYSA-N 0.000 claims 1
KIUYANLPOYKLHJ-UHFFFAOYSA-N 4-[[5-(5-bromopyridin-3-yl)-1,3,4-thiadiazol-2-yl]sulfanyl]-3,5-difluoro-N-hydroxybenzamide Chemical compound ONC(=O)c1cc(F)c(Sc2nnc(s2)-c2cncc(Br)c2)c(F)c1 KIUYANLPOYKLHJ-UHFFFAOYSA-N 0.000 claims 1
ZGJLWPCNZQWLGR-UHFFFAOYSA-N 4-[[5-(5-chlorothiophen-2-yl)tetrazol-2-yl]methyl]-N-hydroxybenzamide Chemical compound ClC1=CC=C(S1)C=1N=NN(N=1)CC1=CC=C(C=C1)C(=O)NO ZGJLWPCNZQWLGR-UHFFFAOYSA-N 0.000 claims 1
DCKAQDQZDMERAL-UHFFFAOYSA-N 4-[[5-(6,6-dimethyl-3-methylsulfanyl-4-oxo-5,7-dihydro-2-benzothiophen-1-yl)tetrazol-2-yl]methyl]-N-hydroxybenzamide Chemical compound CC1(CC(C=2C(=C(SC=2SC)C=2N=NN(N=2)CC2=CC=C(C=C2)C(=O)NO)C1)=O)C DCKAQDQZDMERAL-UHFFFAOYSA-N 0.000 claims 1
WDPFHXJFRPMVTE-UHFFFAOYSA-N 4-[[5-(furan-2-yl)tetrazol-1-yl]methyl]-N-hydroxybenzamide Chemical compound O1C(=CC=C1)C1=NN=NN1CC1=CC=C(C=C1)C(=O)NO WDPFHXJFRPMVTE-UHFFFAOYSA-N 0.000 claims 1
QNQIDISKSGGWRL-LBPRGKRZSA-N 4-[[5-[(1S)-1-amino-2-(1,3-thiazol-4-yl)ethyl]-1,2,4-oxadiazol-3-yl]methyl]-N-hydroxybenzamide Chemical compound N[C@@H](CC=1N=CSC=1)C1=NC(=NO1)CC1=CC=C(C=C1)C(=O)NO QNQIDISKSGGWRL-LBPRGKRZSA-N 0.000 claims 1
GJMYJSZRWSWVFY-UHFFFAOYSA-N 4-[[5-[(3,4-dimethoxyphenyl)methyl]-1,3,4-oxadiazol-2-yl]methyl]-N-hydroxybenzamide Chemical compound COC=1C=C(C=CC=1OC)CC1=NN=C(O1)CC1=CC=C(C=C1)C(=O)NO GJMYJSZRWSWVFY-UHFFFAOYSA-N 0.000 claims 1
ZUJMBFPVDVLZPI-UHFFFAOYSA-N 4-[[5-[(3,4-dimethoxyphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,2,4-triazol-3-yl]methyl]-N-hydroxybenzamide Chemical compound COC=1C=C(C=CC=1OC)CC=1N=C(N(N=1)C1=CC=C(C=C1)C(F)(F)F)CC1=CC=C(C=C1)C(=O)NO ZUJMBFPVDVLZPI-UHFFFAOYSA-N 0.000 claims 1
IBLOHTSZXKCCAW-UHFFFAOYSA-N 4-[[5-[3-(4-benzylpiperazin-1-yl)sulfonylphenyl]-4-methyl-1,2,4-triazol-3-yl]sulfanyl]-3,5-difluoro-N-hydroxybenzamide Chemical compound Cn1c(Sc2c(F)cc(cc2F)C(=O)NO)nnc1-c1cccc(c1)S(=O)(=O)N1CCN(Cc2ccccc2)CC1 IBLOHTSZXKCCAW-UHFFFAOYSA-N 0.000 claims 1
FVPXQKCEJHRCRK-UHFFFAOYSA-N 4-[[5-[3-(azepan-1-ylmethyl)phenyl]-4-methyl-1,2,4-triazol-3-yl]sulfanyl]-3,5-difluoro-N-hydroxybenzamide Chemical compound Cn1c(Sc2c(F)cc(cc2F)C(=O)NO)nnc1-c1cccc(CN2CCCCCC2)c1 FVPXQKCEJHRCRK-UHFFFAOYSA-N 0.000 claims 1
HTWSGOAKJGRUTD-UHFFFAOYSA-N 4-[[5-[3-(diethylsulfamoyl)phenyl]-4-methyl-1,2,4-triazol-3-yl]sulfanyl]-N-hydroxybenzamide Chemical compound C(C)N(S(=O)(=O)C=1C=C(C=CC=1)C=1N(C(=NN=1)SC1=CC=C(C=C1)C(=O)NO)C)CC HTWSGOAKJGRUTD-UHFFFAOYSA-N 0.000 claims 1
OIYDIDZWKQULQJ-UHFFFAOYSA-N 4-[[5-[3-(dimethylamino)phenyl]-4-methyl-1,2,4-triazol-3-yl]sulfanyl]-3,5-difluoro-N-hydroxybenzamide Chemical compound CN(C)c1cccc(c1)-c1nnc(Sc2c(F)cc(cc2F)C(=O)NO)n1C OIYDIDZWKQULQJ-UHFFFAOYSA-N 0.000 claims 1
BMBUVWIWLFOQIW-UHFFFAOYSA-N 4-[[5-[3-(dimethylamino)phenyl]-4-methyl-1,2,4-triazol-3-yl]sulfanyl]-N-hydroxybenzamide Chemical compound CN(C=1C=C(C=CC=1)C=1N(C(=NN=1)SC1=CC=C(C=C1)C(=O)NO)C)C BMBUVWIWLFOQIW-UHFFFAOYSA-N 0.000 claims 1
SUHYHACFWDPRSO-UHFFFAOYSA-N 4-[[5-[3-(dimethylsulfamoyl)phenyl]-1,3,4-oxadiazol-2-yl]methyl]-N-hydroxybenzamide Chemical compound CN(S(=O)(=O)C=1C=C(C=CC=1)C1=NN=C(O1)CC1=CC=C(C(=O)NO)C=C1)C SUHYHACFWDPRSO-UHFFFAOYSA-N 0.000 claims 1
SDWOZBLJNQUKAR-UHFFFAOYSA-N 4-[[5-[3-(dimethylsulfamoyl)phenyl]tetrazol-2-yl]methyl]-N-hydroxybenzamide Chemical compound CN(S(=O)(=O)C=1C=C(C=CC=1)C=1N=NN(N=1)CC1=CC=C(C=C1)C(=O)NO)C SDWOZBLJNQUKAR-UHFFFAOYSA-N 0.000 claims 1
NLEYXVZVINBVID-UHFFFAOYSA-N 4-[[5-[3-[[benzyl(methyl)amino]methyl]phenyl]-4-methyl-1,2,4-triazol-3-yl]sulfanyl]-3,5-difluoro-N-hydroxybenzamide Chemical compound CN(Cc1ccccc1)Cc1cccc(c1)-c1nnc(Sc2c(F)cc(cc2F)C(=O)NO)n1C NLEYXVZVINBVID-UHFFFAOYSA-N 0.000 claims 1
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JP2019556238A 2017-04-14 2018-04-12 選択的ｈｄａｃ６阻害剤 Active JP7241025B2 (ja)