ZA200509142B

ZA200509142B - Nitrogen-containing heteroaryl compounds and their use in increasing endogenous erythropoietin

Nitrogen-containing heteroaryl compounds and their use in increasing endogenous erythropoietin Download PDF

Info

Publication number: ZA200509142B
Authority: ZA; South Africa
Prior art keywords: hydroxy; isoquinoline; amino; carbonyl; acetic acid
Prior art date: 2003-06-06

Application number

ZA200509142A

Other languages

English (en)

Inventor

Michael P Arend

Lee A Flippen

Guenzler-Pukall Volkmar

Ho-Wen-Bin

Eric D Turtle

Du Xiaohui

Original Assignee

Fibrogen Inc

Priority date

2003-06-06

Filing date

2004-06-04

Publication date

2007-04-25

2004-06-04 Application filed by Fibrogen Inc filed Critical Fibrogen Inc

2007-04-25 Publication of ZA200509142B publication Critical patent/ZA200509142B/en

Links

102000003951 Erythropoietin Human genes 0.000 title claims description 76
108090000394 Erythropoietin Proteins 0.000 title claims description 76
229940105423 erythropoietin Drugs 0.000 title claims description 76
OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 title claims description 76
230000001965 increasing effect Effects 0.000 title description 16
-1 amino, substituted amino Chemical group 0.000 claims description 299
150000001875 compounds Chemical class 0.000 claims description 251
125000001072 heteroaryl group Chemical group 0.000 claims description 216
125000000623 heterocyclic group Chemical group 0.000 claims description 189
125000003118 aryl group Chemical group 0.000 claims description 156
125000000217 alkyl group Chemical group 0.000 claims description 153
229910052739 hydrogen Inorganic materials 0.000 claims description 135
239000001257 hydrogen Substances 0.000 claims description 135
239000000203 mixture Substances 0.000 claims description 130
125000000547 substituted alkyl group Chemical group 0.000 claims description 117
125000003107 substituted aryl group Chemical group 0.000 claims description 101
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 93
238000000034 method Methods 0.000 claims description 87
229910052760 oxygen Inorganic materials 0.000 claims description 57
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 55
239000001301 oxygen Substances 0.000 claims description 55
125000003545 alkoxy group Chemical group 0.000 claims description 53
150000003839 salts Chemical class 0.000 claims description 48
208000007502 anemia Diseases 0.000 claims description 47
125000005415 substituted alkoxy group Chemical group 0.000 claims description 43
206010021143 Hypoxia Diseases 0.000 claims description 41
150000002148 esters Chemical class 0.000 claims description 40
125000001424 substituent group Chemical group 0.000 claims description 39
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 39
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 37
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
239000000651 prodrug Substances 0.000 claims description 36
229940002612 prodrug Drugs 0.000 claims description 36
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
125000005843 halogen group Chemical group 0.000 claims description 33
125000004104 aryloxy group Chemical group 0.000 claims description 32
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
208000028867 ischemia Diseases 0.000 claims description 31
125000000753 cycloalkyl group Chemical group 0.000 claims description 30
230000007954 hypoxia Effects 0.000 claims description 29
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 27
229910052757 nitrogen Inorganic materials 0.000 claims description 25
208000035475 disorder Diseases 0.000 claims description 23
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
125000005553 heteroaryloxy group Chemical group 0.000 claims description 20
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 18
208000014674 injury Diseases 0.000 claims description 17
125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 16
229910052799 carbon Inorganic materials 0.000 claims description 16
208000010125 myocardial infarction Diseases 0.000 claims description 16
208000027418 Wounds and injury Diseases 0.000 claims description 15
LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
125000001153 fluoro group Chemical group F* 0.000 claims description 14
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
230000000694 effects Effects 0.000 claims description 13
239000000546 pharmaceutical excipient Substances 0.000 claims description 13
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 12
125000004414 alkyl thio group Chemical group 0.000 claims description 12
125000001309 chloro group Chemical group Cl* 0.000 claims description 12
229910052805 deuterium Inorganic materials 0.000 claims description 12
239000003814 drug Substances 0.000 claims description 12
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
208000006011 Stroke Diseases 0.000 claims description 11
125000001246 bromo group Chemical group Br* 0.000 claims description 11
235000019260 propionic acid Nutrition 0.000 claims description 11
208000010378 Pulmonary Embolism Diseases 0.000 claims description 10
125000000000 cycloalkoxy group Chemical group 0.000 claims description 10
230000006378 damage Effects 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 10
125000002252 acyl group Chemical group 0.000 claims description 9
125000004423 acyloxy group Chemical group 0.000 claims description 9
230000001939 inductive effect Effects 0.000 claims description 9
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
230000008733 trauma Effects 0.000 claims description 9
QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
208000025865 Ulcer Diseases 0.000 claims description 8
125000005110 aryl thio group Chemical group 0.000 claims description 8
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
150000001721 carbon Chemical group 0.000 claims description 8
230000001684 chronic effect Effects 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
206010063837 Reperfusion injury Diseases 0.000 claims description 7
206010052428 Wound Diseases 0.000 claims description 7
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 7
125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
125000002346 iodo group Chemical group I* 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 7
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 7
231100000397 ulcer Toxicity 0.000 claims description 7
125000006598 aminocarbonylamino group Chemical group 0.000 claims description 6
229910052792 caesium Inorganic materials 0.000 claims description 6
230000002401 inhibitory effect Effects 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
150000003573 thiols Chemical class 0.000 claims description 6
102000008109 Mixed Function Oxygenases Human genes 0.000 claims description 5
108010074633 Mixed Function Oxygenases Proteins 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
206010015037 epilepsy Diseases 0.000 claims description 5
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
210000004185 liver Anatomy 0.000 claims description 5
208000015122 neurodegenerative disease Diseases 0.000 claims description 5
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
125000005338 substituted cycloalkoxy group Chemical group 0.000 claims description 5
229940124597 therapeutic agent Drugs 0.000 claims description 5
QJWFWOUODUTVCE-ZCFIWIBFSA-N (2r)-2-[(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)N[C@H](C)C(O)=O)=NC(Cl)=C21 QJWFWOUODUTVCE-ZCFIWIBFSA-N 0.000 claims description 4
KTXIBXJQKYGZJU-GFCCVEGCSA-N (2r)-2-[[4-hydroxy-1-(methoxymethyl)-7-phenoxyisoquinoline-3-carbonyl]amino]propanoic acid Chemical compound C1=C2C(COC)=NC(C(=O)N[C@H](C)C(O)=O)=C(O)C2=CC=C1OC1=CC=CC=C1 KTXIBXJQKYGZJU-GFCCVEGCSA-N 0.000 claims description 4
WGHCPTMPKWJUDP-NSHDSACASA-N (2s)-2-[(7-cyclohexyloxy-4-hydroxyisoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=CC2=C(O)C(C(=O)N[C@@H](C)C(O)=O)=NC=C2C=C1OC1CCCCC1 WGHCPTMPKWJUDP-NSHDSACASA-N 0.000 claims description 4
208000012902 Nervous system disease Diseases 0.000 claims description 4
208000025966 Neurological disease Diseases 0.000 claims description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
230000001404 mediated effect Effects 0.000 claims description 4
230000004770 neurodegeneration Effects 0.000 claims description 4
ITTVOYWUUDHKHB-LLVKDONJSA-N (2r)-2-[(1-chloro-4-hydroxy-6-phenylmethoxyisoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C=1C2=C(O)C(C(=O)N[C@H](C)C(O)=O)=NC(Cl)=C2C=CC=1OCC1=CC=CC=C1 ITTVOYWUUDHKHB-LLVKDONJSA-N 0.000 claims description 3
WMHAINKACZWVSN-LLVKDONJSA-N (2r)-2-[(1-chloro-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carbonyl)amino]-3-hydroxypropanoic acid Chemical compound ClC1=NC(C(=O)N[C@H](CO)C(O)=O)=C(O)C2=CC(OC(C)C)=CC=C21 WMHAINKACZWVSN-LLVKDONJSA-N 0.000 claims description 3
SWMGXKRIPILTFR-CYBMUJFWSA-N (2r)-2-[(1-chloro-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carbonyl)amino]-3-methylbutanoic acid Chemical compound ClC1=NC(C(=O)N[C@H](C(C)C)C(O)=O)=C(O)C2=CC(OC(C)C)=CC=C21 SWMGXKRIPILTFR-CYBMUJFWSA-N 0.000 claims description 3
KBURMXBRBPEALW-LLVKDONJSA-N (2r)-2-[(1-chloro-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carbonyl)amino]butanedioic acid Chemical compound ClC1=NC(C(=O)N[C@H](CC(O)=O)C(O)=O)=C(O)C2=CC(OC(C)C)=CC=C21 KBURMXBRBPEALW-LLVKDONJSA-N 0.000 claims description 3
VRUYUVQNAMQHCJ-QGZVFWFLSA-N (2r)-2-[(1-chloro-4-hydroxy-7-propan-2-yloxyisoquinoline-3-carbonyl)amino]-3-(4-hydroxyphenyl)propanoic acid Chemical compound C([C@@H](NC(=O)C1=C(O)C2=CC=C(C=C2C(Cl)=N1)OC(C)C)C(O)=O)C1=CC=C(O)C=C1 VRUYUVQNAMQHCJ-QGZVFWFLSA-N 0.000 claims description 3
XMDDBTSZIBBIGL-LLVKDONJSA-N (2r)-2-[(1-chloro-4-hydroxy-7-propan-2-yloxyisoquinoline-3-carbonyl)amino]-3-hydroxypropanoic acid Chemical compound OC1=C(C(=O)N[C@H](CO)C(O)=O)N=C(Cl)C2=CC(OC(C)C)=CC=C21 XMDDBTSZIBBIGL-LLVKDONJSA-N 0.000 claims description 3
AHDFCJIMXKTQKA-QGZVFWFLSA-N (2r)-2-[(1-chloro-4-hydroxy-7-propan-2-yloxyisoquinoline-3-carbonyl)amino]-3-phenylpropanoic acid Chemical compound C([C@@H](NC(=O)C1=C(O)C2=CC=C(C=C2C(Cl)=N1)OC(C)C)C(O)=O)C1=CC=CC=C1 AHDFCJIMXKTQKA-QGZVFWFLSA-N 0.000 claims description 3
QHMVFDODSPOSTQ-LLVKDONJSA-N (2r)-2-[(1-chloro-4-hydroxy-7-propan-2-yloxyisoquinoline-3-carbonyl)amino]butanedioic acid Chemical compound OC1=C(C(=O)N[C@H](CC(O)=O)C(O)=O)N=C(Cl)C2=CC(OC(C)C)=CC=C21 QHMVFDODSPOSTQ-LLVKDONJSA-N 0.000 claims description 3
CMRBZAGEXPEKDW-CQSZACIVSA-N (2r)-2-[(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]-3-(4-hydroxyphenyl)propanoic acid Chemical compound C([C@H](C(=O)O)NC(=O)C=1C(=C2C=CC=CC2=C(Cl)N=1)O)C1=CC=C(O)C=C1 CMRBZAGEXPEKDW-CQSZACIVSA-N 0.000 claims description 3
HSUYTQLGVGVBSZ-MRVPVSSYSA-N (2r)-2-[(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]butanedioic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)N[C@H](CC(=O)O)C(O)=O)=NC(Cl)=C21 HSUYTQLGVGVBSZ-MRVPVSSYSA-N 0.000 claims description 3
RWNPSYWHXOSWNZ-LLVKDONJSA-N (2r)-2-[(4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=CC2=C(O)C(C(=O)N[C@H](C)C(O)=O)=NC=C2C=C1OC1=CC=CC=C1 RWNPSYWHXOSWNZ-LLVKDONJSA-N 0.000 claims description 3
OIKSVGNTJSMVFQ-LLVKDONJSA-N (2r)-2-[(4-hydroxy-7-phenylsulfanylisoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=CC2=C(O)C(C(=O)N[C@H](C)C(O)=O)=NC=C2C=C1SC1=CC=CC=C1 OIKSVGNTJSMVFQ-LLVKDONJSA-N 0.000 claims description 3
AJAXJHZVMPSFQE-SNVBAGLBSA-N (2r)-2-[[1-(4-chlorophenyl)sulfanyl-4-hydroxyisoquinoline-3-carbonyl]amino]propanoic acid Chemical compound C=12C=CC=CC2=C(O)C(C(=O)N[C@H](C)C(O)=O)=NC=1SC1=CC=C(Cl)C=C1 AJAXJHZVMPSFQE-SNVBAGLBSA-N 0.000 claims description 3
ZBVXGRVWMYUHIB-JTQLQIEISA-N (2s)-1-(1-chloro-4-hydroxyisoquinoline-3-carbonyl)pyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(=O)C1=NC(Cl)=C(C=CC=C2)C2=C1O ZBVXGRVWMYUHIB-JTQLQIEISA-N 0.000 claims description 3
ZNYCBDUMDGCVCR-ZDUSSCGKSA-N (2s)-2-[(1-chloro-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carbonyl)amino]pentanoic acid Chemical compound C1=CC(OC(C)C)=CC2=C(O)C(C(=O)N[C@@H](CCC)C(O)=O)=NC(Cl)=C21 ZNYCBDUMDGCVCR-ZDUSSCGKSA-N 0.000 claims description 3
MXDAYDGJKVLTJP-NSHDSACASA-N (2s)-2-[(1-chloro-4-hydroxy-7-phenylmethoxyisoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=CC2=C(O)C(C(=O)N[C@@H](C)C(O)=O)=NC(Cl)=C2C=C1OCC1=CC=CC=C1 MXDAYDGJKVLTJP-NSHDSACASA-N 0.000 claims description 3
XMDDBTSZIBBIGL-NSHDSACASA-N (2s)-2-[(1-chloro-4-hydroxy-7-propan-2-yloxyisoquinoline-3-carbonyl)amino]-3-hydroxypropanoic acid Chemical compound OC1=C(C(=O)N[C@@H](CO)C(O)=O)N=C(Cl)C2=CC(OC(C)C)=CC=C21 XMDDBTSZIBBIGL-NSHDSACASA-N 0.000 claims description 3
BNYWBSPWOHMZNE-JTQLQIEISA-N (2s)-2-[(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]-3-methylbutanoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)N[C@@H](C(C)C)C(O)=O)=NC(Cl)=C21 BNYWBSPWOHMZNE-JTQLQIEISA-N 0.000 claims description 3
QZRXYSFKUSQNIL-AWEZNQCLSA-N (2s)-2-[(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C(=C2C=CC=CC2=C(Cl)N=1)O)C1=CC=CC=C1 QZRXYSFKUSQNIL-AWEZNQCLSA-N 0.000 claims description 3
OIKSVGNTJSMVFQ-NSHDSACASA-N (2s)-2-[(4-hydroxy-7-phenylsulfanylisoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=CC2=C(O)C(C(=O)N[C@@H](C)C(O)=O)=NC=C2C=C1SC1=CC=CC=C1 OIKSVGNTJSMVFQ-NSHDSACASA-N 0.000 claims description 3
GZXASRBPKSJIOI-NSHDSACASA-N (2s)-2-[(7-phenoxy-4-sulfanylisoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=CC2=C(S)C(C(=O)N[C@@H](C)C(O)=O)=NC=C2C=C1OC1=CC=CC=C1 GZXASRBPKSJIOI-NSHDSACASA-N 0.000 claims description 3
AJAXJHZVMPSFQE-JTQLQIEISA-N (2s)-2-[[1-(4-chlorophenyl)sulfanyl-4-hydroxyisoquinoline-3-carbonyl]amino]propanoic acid Chemical compound C=12C=CC=CC2=C(O)C(C(=O)N[C@@H](C)C(O)=O)=NC=1SC1=CC=C(Cl)C=C1 AJAXJHZVMPSFQE-JTQLQIEISA-N 0.000 claims description 3
NVTGRVHNCWQLCS-NSHDSACASA-N (2s)-2-[[4-hydroxy-7-(4-methoxyphenoxy)isoquinoline-3-carbonyl]amino]propanoic acid Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(C(O)=C(N=C2)C(=O)N[C@@H](C)C(O)=O)C2=C1 NVTGRVHNCWQLCS-NSHDSACASA-N 0.000 claims description 3
FYCIPQQTSAXANG-JTQLQIEISA-N (2s)-2-[[7-(3-fluoro-5-methoxyphenoxy)-4-hydroxyisoquinoline-3-carbonyl]amino]propanoic acid Chemical compound COC1=CC(F)=CC(OC=2C=C3C=NC(=C(O)C3=CC=2)C(=O)N[C@@H](C)C(O)=O)=C1 FYCIPQQTSAXANG-JTQLQIEISA-N 0.000 claims description 3
ZZPJAWAZDFVHJV-JTQLQIEISA-N (2s)-2-[[7-(4-chlorophenoxy)-4-hydroxyisoquinoline-3-carbonyl]amino]propanoic acid Chemical compound C1=CC2=C(O)C(C(=O)N[C@@H](C)C(O)=O)=NC=C2C=C1OC1=CC=C(Cl)C=C1 ZZPJAWAZDFVHJV-JTQLQIEISA-N 0.000 claims description 3
BPSFIPGYXAJALI-NSHDSACASA-N (2s)-2-[[7-(4-fluorophenoxy)-4-hydroxy-1-methylisoquinoline-3-carbonyl]amino]propanoic acid Chemical compound C1=CC2=C(O)C(C(=O)N[C@@H](C)C(O)=O)=NC(C)=C2C=C1OC1=CC=C(F)C=C1 BPSFIPGYXAJALI-NSHDSACASA-N 0.000 claims description 3
ZSVXGXDLVCWNDK-NSHDSACASA-N (2s)-2-[[7-(benzenesulfonyl)-4-hydroxyisoquinoline-3-carbonyl]amino]propanoic acid Chemical compound C1=CC2=C(O)C(C(=O)N[C@@H](C)C(O)=O)=NC=C2C=C1S(=O)(=O)C1=CC=CC=C1 ZSVXGXDLVCWNDK-NSHDSACASA-N 0.000 claims description 3
VNKVKTPUKAWWTR-UHFFFAOYSA-N 2-[(1,7-dibromo-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=C(Br)C=CC2=C(O)C(C(=O)NCC(=O)O)=NC(Br)=C21 VNKVKTPUKAWWTR-UHFFFAOYSA-N 0.000 claims description 3
LZFBLELQFUANKK-UHFFFAOYSA-N 2-[(1-anilino-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=12C=CC=CC2=C(O)C(C(=O)NCC(=O)O)=NC=1NC1=CC=CC=C1 LZFBLELQFUANKK-UHFFFAOYSA-N 0.000 claims description 3
XJYVWBBYSRVPAH-UHFFFAOYSA-N 2-[(1-bromo-4-hydroxy-7-methylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound OC1=C(C(=O)NCC(O)=O)N=C(Br)C2=CC(C)=CC=C21 XJYVWBBYSRVPAH-UHFFFAOYSA-N 0.000 claims description 3
DBUIYLIIAOOSFP-UHFFFAOYSA-N 2-[(1-bromo-4-hydroxy-7-phenylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC2=C(O)C(C(=O)NCC(=O)O)=NC(Br)=C2C=C1C1=CC=CC=C1 DBUIYLIIAOOSFP-UHFFFAOYSA-N 0.000 claims description 3
HAYDDRQIZCDVFF-UHFFFAOYSA-N 2-[(1-bromo-4-hydroxy-7-phenylsulfanylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC2=C(O)C(C(=O)NCC(=O)O)=NC(Br)=C2C=C1SC1=CC=CC=C1 HAYDDRQIZCDVFF-UHFFFAOYSA-N 0.000 claims description 3
BITRBOJBLALYKV-UHFFFAOYSA-N 2-[(1-bromo-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)NCC(=O)O)=NC(Br)=C21 BITRBOJBLALYKV-UHFFFAOYSA-N 0.000 claims description 3
DKYDAIUSFRAUDT-UHFFFAOYSA-N 2-[(1-bromo-7-butoxy-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound OC1=C(C(=O)NCC(O)=O)N=C(Br)C2=CC(OCCCC)=CC=C21 DKYDAIUSFRAUDT-UHFFFAOYSA-N 0.000 claims description 3
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MXDAYDGJKVLTJP-LLVKDONJSA-N (2r)-2-[(1-chloro-4-hydroxy-7-phenylmethoxyisoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=CC2=C(O)C(C(=O)N[C@H](C)C(O)=O)=NC(Cl)=C2C=C1OCC1=CC=CC=C1 MXDAYDGJKVLTJP-LLVKDONJSA-N 0.000 claims description 2
OHJZDNKPKNFUNG-CYBMUJFWSA-N (2r)-2-[(1-chloro-4-hydroxy-7-propan-2-yloxyisoquinoline-3-carbonyl)amino]-3-methylbutanoic acid Chemical compound OC1=C(C(=O)N[C@H](C(C)C)C(O)=O)N=C(Cl)C2=CC(OC(C)C)=CC=C21 OHJZDNKPKNFUNG-CYBMUJFWSA-N 0.000 claims description 2
VLPWMPXAVDLICR-MRVPVSSYSA-N (2r)-2-[(1-chloro-4-hydroxy-7-propan-2-yloxyisoquinoline-3-carbonyl)amino]propanoic acid Chemical compound OC1=C(C(=O)N[C@H](C)C(O)=O)N=C(Cl)C2=CC(OC(C)C)=CC=C21 VLPWMPXAVDLICR-MRVPVSSYSA-N 0.000 claims description 2
XYGJJVIZDZGHOX-LLVKDONJSA-N (2r)-2-[(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]-3-(1h-imidazol-5-yl)propanoic acid Chemical compound C([C@H](C(=O)O)NC(=O)C=1C(=C2C=CC=CC2=C(Cl)N=1)O)C1=CNC=N1 XYGJJVIZDZGHOX-LLVKDONJSA-N 0.000 claims description 2
BHZCYTXADFEUIR-MRVPVSSYSA-N (2r)-2-[(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]-3-hydroxypropanoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)N[C@H](CO)C(O)=O)=NC(Cl)=C21 BHZCYTXADFEUIR-MRVPVSSYSA-N 0.000 claims description 2
BNYWBSPWOHMZNE-SNVBAGLBSA-N (2r)-2-[(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]-3-methylbutanoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)N[C@H](C(C)C)C(O)=O)=NC(Cl)=C21 BNYWBSPWOHMZNE-SNVBAGLBSA-N 0.000 claims description 2
KJMWOZKWSLSPPT-CQSZACIVSA-N (2r)-6-amino-2-[(1-chloro-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carbonyl)amino]hexanoic acid Chemical compound ClC1=NC(C(=O)N[C@H](CCCCN)C(O)=O)=C(O)C2=CC(OC(C)C)=CC=C21 KJMWOZKWSLSPPT-CQSZACIVSA-N 0.000 claims description 2
FAEUXUGPGAVTCW-CQSZACIVSA-N (2r)-6-amino-2-[(1-chloro-4-hydroxy-7-propan-2-yloxyisoquinoline-3-carbonyl)amino]hexanoic acid Chemical compound OC1=C(C(=O)N[C@H](CCCCN)C(O)=O)N=C(Cl)C2=CC(OC(C)C)=CC=C21 FAEUXUGPGAVTCW-CQSZACIVSA-N 0.000 claims description 2
OMGWEUOUDGHHBY-ZDUSSCGKSA-N (2s)-1-(1-chloro-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carbonyl)pyrrolidine-2-carboxylic acid Chemical compound OC=1C2=CC(OC(C)C)=CC=C2C(Cl)=NC=1C(=O)N1CCC[C@H]1C(O)=O OMGWEUOUDGHHBY-ZDUSSCGKSA-N 0.000 claims description 2
HIWTVSSFXPVEQI-KRWDZBQOSA-N (2s)-2-[(1-chloro-4-hydroxy-6-phenylmethoxyisoquinoline-3-carbonyl)amino]-3-methylbutanoic acid Chemical compound C=1C2=C(O)C(C(=O)N[C@@H](C(C)C)C(O)=O)=NC(Cl)=C2C=CC=1OCC1=CC=CC=C1 HIWTVSSFXPVEQI-KRWDZBQOSA-N 0.000 claims description 2
WMHAINKACZWVSN-NSHDSACASA-N (2s)-2-[(1-chloro-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carbonyl)amino]-3-hydroxypropanoic acid Chemical compound ClC1=NC(C(=O)N[C@@H](CO)C(O)=O)=C(O)C2=CC(OC(C)C)=CC=C21 WMHAINKACZWVSN-NSHDSACASA-N 0.000 claims description 2
SWMGXKRIPILTFR-ZDUSSCGKSA-N (2s)-2-[(1-chloro-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carbonyl)amino]-3-methylbutanoic acid Chemical compound ClC1=NC(C(=O)N[C@@H](C(C)C)C(O)=O)=C(O)C2=CC(OC(C)C)=CC=C21 SWMGXKRIPILTFR-ZDUSSCGKSA-N 0.000 claims description 2
KBURMXBRBPEALW-NSHDSACASA-N (2s)-2-[(1-chloro-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carbonyl)amino]butanedioic acid Chemical compound ClC1=NC(C(=O)N[C@@H](CC(O)=O)C(O)=O)=C(O)C2=CC(OC(C)C)=CC=C21 KBURMXBRBPEALW-NSHDSACASA-N 0.000 claims description 2
AKODIUCEFXSNKM-QMMMGPOBSA-N (2s)-2-[(1-chloro-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carbonyl)amino]propanoic acid Chemical compound ClC1=NC(C(=O)N[C@@H](C)C(O)=O)=C(O)C2=CC(OC(C)C)=CC=C21 AKODIUCEFXSNKM-QMMMGPOBSA-N 0.000 claims description 2
AHDFCJIMXKTQKA-KRWDZBQOSA-N (2s)-2-[(1-chloro-4-hydroxy-7-propan-2-yloxyisoquinoline-3-carbonyl)amino]-3-phenylpropanoic acid Chemical compound C([C@H](NC(=O)C1=C(O)C2=CC=C(C=C2C(Cl)=N1)OC(C)C)C(O)=O)C1=CC=CC=C1 AHDFCJIMXKTQKA-KRWDZBQOSA-N 0.000 claims description 2
XYGJJVIZDZGHOX-NSHDSACASA-N (2s)-2-[(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]-3-(1h-imidazol-5-yl)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C(=C2C=CC=CC2=C(Cl)N=1)O)C1=CNC=N1 XYGJJVIZDZGHOX-NSHDSACASA-N 0.000 claims description 2
CMRBZAGEXPEKDW-AWEZNQCLSA-N (2s)-2-[(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]-3-(4-hydroxyphenyl)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C(=C2C=CC=CC2=C(Cl)N=1)O)C1=CC=C(O)C=C1 CMRBZAGEXPEKDW-AWEZNQCLSA-N 0.000 claims description 2
BHZCYTXADFEUIR-QMMMGPOBSA-N (2s)-2-[(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]-3-hydroxypropanoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)N[C@@H](CO)C(O)=O)=NC(Cl)=C21 BHZCYTXADFEUIR-QMMMGPOBSA-N 0.000 claims description 2
HSUYTQLGVGVBSZ-QMMMGPOBSA-N (2s)-2-[(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]butanedioic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)N[C@@H](CC(=O)O)C(O)=O)=NC(Cl)=C21 HSUYTQLGVGVBSZ-QMMMGPOBSA-N 0.000 claims description 2
OFBPLXQLTAJHLH-LBPRGKRZSA-N (2s)-2-[(4-hydroxy-1-methyl-7-phenoxyisoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=CC2=C(O)C(C(=O)N[C@@H](C)C(O)=O)=NC(C)=C2C=C1OC1=CC=CC=C1 OFBPLXQLTAJHLH-LBPRGKRZSA-N 0.000 claims description 2
KTXIBXJQKYGZJU-LBPRGKRZSA-N (2s)-2-[[4-hydroxy-1-(methoxymethyl)-7-phenoxyisoquinoline-3-carbonyl]amino]propanoic acid Chemical compound C1=C2C(COC)=NC(C(=O)N[C@@H](C)C(O)=O)=C(O)C2=CC=C1OC1=CC=CC=C1 KTXIBXJQKYGZJU-LBPRGKRZSA-N 0.000 claims description 2
MHTNGPYRSCKLPI-JTQLQIEISA-N (2s)-2-[[4-hydroxy-7-[4-(trifluoromethyl)phenoxy]isoquinoline-3-carbonyl]amino]propanoic acid Chemical compound C1=CC2=C(O)C(C(=O)N[C@@H](C)C(O)=O)=NC=C2C=C1OC1=CC=C(C(F)(F)F)C=C1 MHTNGPYRSCKLPI-JTQLQIEISA-N 0.000 claims description 2
KJMWOZKWSLSPPT-AWEZNQCLSA-N (2s)-6-amino-2-[(1-chloro-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carbonyl)amino]hexanoic acid Chemical compound ClC1=NC(C(=O)N[C@@H](CCCCN)C(O)=O)=C(O)C2=CC(OC(C)C)=CC=C21 KJMWOZKWSLSPPT-AWEZNQCLSA-N 0.000 claims description 2
FAEUXUGPGAVTCW-AWEZNQCLSA-N (2s)-6-amino-2-[(1-chloro-4-hydroxy-7-propan-2-yloxyisoquinoline-3-carbonyl)amino]hexanoic acid Chemical compound OC1=C(C(=O)N[C@@H](CCCCN)C(O)=O)N=C(Cl)C2=CC(OC(C)C)=CC=C21 FAEUXUGPGAVTCW-AWEZNQCLSA-N 0.000 claims description 2
DNBFVVLLIUHUSX-NSHDSACASA-N (2s)-6-amino-2-[(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]hexanoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)N[C@@H](CCCCN)C(O)=O)=NC(Cl)=C21 DNBFVVLLIUHUSX-NSHDSACASA-N 0.000 claims description 2
ILFIRBGRMCGNOO-UHFFFAOYSA-N 1,1-bis($l^{1}-oxidanyl)ethene Chemical group [O]C([O])=C ILFIRBGRMCGNOO-UHFFFAOYSA-N 0.000 claims description 2
VXXFUUPGQCVILJ-UHFFFAOYSA-N 1-[(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]cyclopropane-1-carboxylic acid Chemical compound N=1C(Cl)=C2C=CC=CC2=C(O)C=1C(=O)NC1(C(=O)O)CC1 VXXFUUPGQCVILJ-UHFFFAOYSA-N 0.000 claims description 2
OAGHQTCGZORZNW-UHFFFAOYSA-N 1-chloro-4-hydroxy-n-(2-hydroxyethyl)-6-propan-2-yloxyisoquinoline-3-carboxamide Chemical compound ClC1=NC(C(=O)NCCO)=C(O)C2=CC(OC(C)C)=CC=C21 OAGHQTCGZORZNW-UHFFFAOYSA-N 0.000 claims description 2
YLYDVGDICQJMKX-UHFFFAOYSA-N 1-chloro-4-hydroxy-n-(2-hydroxyethyl)isoquinoline-3-carboxamide Chemical compound C1=CC=CC2=C(O)C(C(=O)NCCO)=NC(Cl)=C21 YLYDVGDICQJMKX-UHFFFAOYSA-N 0.000 claims description 2
HAMSJHDTXKWQJR-UHFFFAOYSA-N 1-chloro-4-hydroxy-n-(2-methoxyethyl)-6-propan-2-yloxyisoquinoline-3-carboxamide Chemical compound C1=CC(OC(C)C)=CC2=C(O)C(C(=O)NCCOC)=NC(Cl)=C21 HAMSJHDTXKWQJR-UHFFFAOYSA-N 0.000 claims description 2
XUIHUGWOEFVUIF-UHFFFAOYSA-N 1-chloro-4-hydroxy-n-(2-methoxyethyl)-7-propan-2-yloxyisoquinoline-3-carboxamide Chemical compound C1=C(OC(C)C)C=CC2=C(O)C(C(=O)NCCOC)=NC(Cl)=C21 XUIHUGWOEFVUIF-UHFFFAOYSA-N 0.000 claims description 2
PNBZVCGYURAHSP-UHFFFAOYSA-N 1-chloro-4-hydroxy-n-(2-methoxyethyl)isoquinoline-3-carboxamide Chemical compound C1=CC=CC2=C(O)C(C(=O)NCCOC)=NC(Cl)=C21 PNBZVCGYURAHSP-UHFFFAOYSA-N 0.000 claims description 2
CNPHYMXKGNATEG-UHFFFAOYSA-N 1-chloro-n-(1,3-dihydroxypropan-2-yl)-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carboxamide Chemical compound ClC1=NC(C(=O)NC(CO)CO)=C(O)C2=CC(OC(C)C)=CC=C21 CNPHYMXKGNATEG-UHFFFAOYSA-N 0.000 claims description 2
QRCDGQCXTWXABA-UHFFFAOYSA-N 1-chloro-n-(1,3-dihydroxypropan-2-yl)-4-hydroxy-7-propan-2-yloxyisoquinoline-3-carboxamide Chemical compound OC1=C(C(=O)NC(CO)CO)N=C(Cl)C2=CC(OC(C)C)=CC=C21 QRCDGQCXTWXABA-UHFFFAOYSA-N 0.000 claims description 2
HKDMZPPEVCYUCR-UHFFFAOYSA-N 1-chloro-n-(1,3-dihydroxypropan-2-yl)-4-hydroxyisoquinoline-3-carboxamide Chemical compound C1=CC=CC2=C(O)C(C(=O)NC(CO)CO)=NC(Cl)=C21 HKDMZPPEVCYUCR-UHFFFAOYSA-N 0.000 claims description 2
FWWDLDOAMRAZGX-UHFFFAOYSA-N 1-chloro-n-[2-(dimethylamino)ethyl]-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carboxamide Chemical compound ClC1=NC(C(=O)NCCN(C)C)=C(O)C2=CC(OC(C)C)=CC=C21 FWWDLDOAMRAZGX-UHFFFAOYSA-N 0.000 claims description 2
WHRIPCWHASQYKE-UHFFFAOYSA-N 1-chloro-n-[2-(dimethylamino)ethyl]-4-hydroxy-7-propan-2-yloxyisoquinoline-3-carboxamide Chemical compound OC1=C(C(=O)NCCN(C)C)N=C(Cl)C2=CC(OC(C)C)=CC=C21 WHRIPCWHASQYKE-UHFFFAOYSA-N 0.000 claims description 2
FQCLLIYTKXBBON-UHFFFAOYSA-N 2-[(1-bromo-4-hydroxy-6-phenylsulfanylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC(Br)=C2C=CC=1SC1=CC=CC=C1 FQCLLIYTKXBBON-UHFFFAOYSA-N 0.000 claims description 2
CNUPSYDUIZEIPO-UHFFFAOYSA-N 2-[(1-bromo-6-butoxy-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound BrC1=NC(C(=O)NCC(O)=O)=C(O)C2=CC(OCCCC)=CC=C21 CNUPSYDUIZEIPO-UHFFFAOYSA-N 0.000 claims description 2
GLMQFBODDPZQKK-UHFFFAOYSA-N 2-[(1-bromo-6-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC(Cl)=CC2=C(O)C(C(=O)NCC(=O)O)=NC(Br)=C21 GLMQFBODDPZQKK-UHFFFAOYSA-N 0.000 claims description 2
QDGVEHNZYSBJQY-UHFFFAOYSA-N 2-[(1-chloro-4-ethoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC=C2C(OCC)=C(C(=O)NCC(O)=O)N=C(Cl)C2=C1 QDGVEHNZYSBJQY-UHFFFAOYSA-N 0.000 claims description 2
OLKHXIWCDITTRS-UHFFFAOYSA-N 2-[(1-chloro-4-hydroxy-5-phenylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C12=C(O)C(C(=O)NCC(=O)O)=NC(Cl)=C2C=CC=C1C1=CC=CC=C1 OLKHXIWCDITTRS-UHFFFAOYSA-N 0.000 claims description 2
QMPBXOCKGUYVRW-UHFFFAOYSA-N 2-[(1-chloro-4-hydroxy-6,7-diphenoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C=CC=CC=1OC1=CC2=C(O)C(C(=O)NCC(=O)O)=NC(Cl)=C2C=C1OC1=CC=CC=C1 QMPBXOCKGUYVRW-UHFFFAOYSA-N 0.000 claims description 2
DIIGKDLXPXTJKF-UHFFFAOYSA-N 2-[(1-chloro-4-hydroxy-6-phenylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC(Cl)=C2C=CC=1C1=CC=CC=C1 DIIGKDLXPXTJKF-UHFFFAOYSA-N 0.000 claims description 2
TZLIRNWOSLSQHX-UHFFFAOYSA-N 2-[(1-chloro-4-hydroxy-6-phenylsulfanylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC(Cl)=C2C=CC=1SC1=CC=CC=C1 TZLIRNWOSLSQHX-UHFFFAOYSA-N 0.000 claims description 2
WIOJUNOKPQQDJW-UHFFFAOYSA-N 2-[(1-chloro-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carbonyl)amino]-2-methylpropanoic acid Chemical compound ClC1=NC(C(=O)NC(C)(C)C(O)=O)=C(O)C2=CC(OC(C)C)=CC=C21 WIOJUNOKPQQDJW-UHFFFAOYSA-N 0.000 claims description 2
HMKFUYCZXIXNIC-UHFFFAOYSA-N 2-[(1-chloro-4-phenylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound OC(=O)CNC(=O)C1=NC(Cl)=C2C=CC=CC2=C1C1=CC=CC=C1 HMKFUYCZXIXNIC-UHFFFAOYSA-N 0.000 claims description 2
IIFVLAFEBPCYBL-UHFFFAOYSA-N 2-[(1-ethoxy-4-phenylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C12=CC=CC=C2C(OCC)=NC(C(=O)NCC(O)=O)=C1C1=CC=CC=C1 IIFVLAFEBPCYBL-UHFFFAOYSA-N 0.000 claims description 2
ZJSHQZAFIQIXIE-UHFFFAOYSA-N 2-[(1-ethyl-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=C2C(CC)=NC(C(=O)NCC(O)=O)=C(O)C2=CC=C1OC1=CC=CC=C1 ZJSHQZAFIQIXIE-UHFFFAOYSA-N 0.000 claims description 2
RLLMAEJERKGPJA-UHFFFAOYSA-N 2-[(1-methyl-7-phenoxy-4-phenylmethoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C12=CC=C(OC=3C=CC=CC=3)C=C2C(C)=NC(C(=O)NCC(O)=O)=C1OCC1=CC=CC=C1 RLLMAEJERKGPJA-UHFFFAOYSA-N 0.000 claims description 2
YROXVVLIBAVXNW-UHFFFAOYSA-N 2-[(4-acetyloxy-1-phenylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C12=CC=CC=C2C(OC(=O)C)=C(C(=O)NCC(O)=O)N=C1C1=CC=CC=C1 YROXVVLIBAVXNW-UHFFFAOYSA-N 0.000 claims description 2
CKALORJROBANNZ-UHFFFAOYSA-N 2-[(4-ethoxy-1-methyl-7-phenoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C=C2C(OCC)=C(C(=O)NCC(O)=O)N=C(C)C2=CC=1OC1=CC=CC=C1 CKALORJROBANNZ-UHFFFAOYSA-N 0.000 claims description 2
ZLDYCVXVGXUSBB-UHFFFAOYSA-N 2-[(4-hydroxy-1-methyl-6-phenoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C=C2C(C)=NC(C(=O)NCC(O)=O)=C(O)C2=CC=1OC1=CC=CC=C1 ZLDYCVXVGXUSBB-UHFFFAOYSA-N 0.000 claims description 2
GZRPBUJBSUUTEZ-UHFFFAOYSA-N 2-[(4-hydroxy-1-pyridin-3-yloxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=12C=CC=CC2=C(O)C(C(=O)NCC(=O)O)=NC=1OC1=CC=CN=C1 GZRPBUJBSUUTEZ-UHFFFAOYSA-N 0.000 claims description 2
GEVROYBOHHONGQ-UHFFFAOYSA-N 2-[(4-hydroxy-5-phenylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C12=C(O)C(C(=O)NCC(=O)O)=NC=C2C=CC=C1C1=CC=CC=C1 GEVROYBOHHONGQ-UHFFFAOYSA-N 0.000 claims description 2
GNZJYFBNTBFKOU-UHFFFAOYSA-N 2-[(4-hydroxy-6,7-diphenoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C=CC=CC=1OC1=CC2=C(O)C(C(=O)NCC(=O)O)=NC=C2C=C1OC1=CC=CC=C1 GNZJYFBNTBFKOU-UHFFFAOYSA-N 0.000 claims description 2
OHSDRMQXZNHGAM-UHFFFAOYSA-N 2-[(4-hydroxy-6-phenoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC=C2C=CC=1OC1=CC=CC=C1 OHSDRMQXZNHGAM-UHFFFAOYSA-N 0.000 claims description 2
NGAQRGUVOHSSGV-UHFFFAOYSA-N 2-[(4-hydroxy-6-phenylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC=C2C=CC=1C1=CC=CC=C1 NGAQRGUVOHSSGV-UHFFFAOYSA-N 0.000 claims description 2
HFWAVTLCGIHQMB-UHFFFAOYSA-N 2-[(4-hydroxy-6-phenylsulfanylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC=C2C=CC=1SC1=CC=CC=C1 HFWAVTLCGIHQMB-UHFFFAOYSA-N 0.000 claims description 2
ASRGHBCJNDTHKI-UHFFFAOYSA-N 2-[(4-hydroxy-6-pyridin-2-ylsulfanylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC=C2C=CC=1SC1=CC=CC=N1 ASRGHBCJNDTHKI-UHFFFAOYSA-N 0.000 claims description 2
VWNWCZPSMKEODA-UHFFFAOYSA-N 2-[(4-hydroxy-6-pyridin-3-yloxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC=C2C=CC=1OC1=CC=CN=C1 VWNWCZPSMKEODA-UHFFFAOYSA-N 0.000 claims description 2
GNKMLRZMKDKKNS-UHFFFAOYSA-N 2-[(4-hydroxy-6-pyridin-4-ylsulfanylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC=C2C=CC=1SC1=CC=NC=C1 GNKMLRZMKDKKNS-UHFFFAOYSA-N 0.000 claims description 2
ADFUJMDKOMCCKK-UHFFFAOYSA-N 2-[(4-hydroxy-7-phenylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC2=C(O)C(C(=O)NCC(=O)O)=NC=C2C=C1C1=CC=CC=C1 ADFUJMDKOMCCKK-UHFFFAOYSA-N 0.000 claims description 2
VPTUYCAFRYDOJE-UHFFFAOYSA-N 2-[(4-hydroxy-8-phenylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C=CC2=C(O)C(C(=O)NCC(=O)O)=NC=C2C=1C1=CC=CC=C1 VPTUYCAFRYDOJE-UHFFFAOYSA-N 0.000 claims description 2
ZCNVEQRDYXFWCP-UHFFFAOYSA-N 2-[(4-phenylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound OC(=O)CNC(=O)C1=NC=C2C=CC=CC2=C1C1=CC=CC=C1 ZCNVEQRDYXFWCP-UHFFFAOYSA-N 0.000 claims description 2
OLXXLUHLRWPORH-UHFFFAOYSA-N 2-[(6-amino-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=NC(C(=O)NCC(O)=O)=C(O)C2=CC(N)=CC=C21 OLXXLUHLRWPORH-UHFFFAOYSA-N 0.000 claims description 2
TYIRVHCDLQWRPL-UHFFFAOYSA-N 2-[(6-bromo-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC(Br)=CC2=C(O)C(C(=O)NCC(=O)O)=NC=C21 TYIRVHCDLQWRPL-UHFFFAOYSA-N 0.000 claims description 2
DGRJRGJRBHJQER-UHFFFAOYSA-N 2-[(6-cyclohexyloxy-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC=C2C=CC=1OC1CCCCC1 DGRJRGJRBHJQER-UHFFFAOYSA-N 0.000 claims description 2
XPTKNZSLMJJIHN-UHFFFAOYSA-N 2-[(7-phenoxy-4-sulfanylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC2=C(S)C(C(=O)NCC(=O)O)=NC=C2C=C1OC1=CC=CC=C1 XPTKNZSLMJJIHN-UHFFFAOYSA-N 0.000 claims description 2
ZMPXGIKBERIEOB-UHFFFAOYSA-N 2-[[1-(dimethylcarbamoyl)-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2C(C(=O)N(C)C)=NC(C(=O)NCC(O)=O)=C(O)C2=CC=C1OC1=CC=CC=C1 ZMPXGIKBERIEOB-UHFFFAOYSA-N 0.000 claims description 2
QBLGJCXZDGUPFS-UHFFFAOYSA-N 2-[[1-chloro-4-hydroxy-6-(4-methoxyphenoxy)isoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(C(Cl)=NC(C(=O)NCC(O)=O)=C2O)C2=C1 QBLGJCXZDGUPFS-UHFFFAOYSA-N 0.000 claims description 2
AMMLCSAPYKXFOZ-UHFFFAOYSA-N 2-[[1-chloro-6-(4-fluorophenoxy)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC(Cl)=C2C=CC=1OC1=CC=C(F)C=C1 AMMLCSAPYKXFOZ-UHFFFAOYSA-N 0.000 claims description 2
PTOVSWQZNHNDDO-UHFFFAOYSA-N 2-[[4-hydroxy-1-(4-methylphenyl)isoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CC(C)=CC=C1C1=NC(C(=O)NCC(O)=O)=C(O)C2=CC=CC=C12 PTOVSWQZNHNDDO-UHFFFAOYSA-N 0.000 claims description 2
MHMUTVWPLKKCIN-UHFFFAOYSA-N 2-[[4-hydroxy-6-(4-methoxyphenoxy)-1-methylisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(C(C)=NC(C(=O)NCC(O)=O)=C2O)C2=C1 MHMUTVWPLKKCIN-UHFFFAOYSA-N 0.000 claims description 2
KJXPPUWCVVMWDK-UHFFFAOYSA-N 2-[[4-hydroxy-6-(phenylcarbamoylamino)isoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC=C2C=CC=1NC(=O)NC1=CC=CC=C1 KJXPPUWCVVMWDK-UHFFFAOYSA-N 0.000 claims description 2
IUCNGVKPJTZEQQ-UHFFFAOYSA-N 2-[[4-hydroxy-6-[4-(trifluoromethyl)phenoxy]isoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC=C2C=CC=1OC1=CC=C(C(F)(F)F)C=C1 IUCNGVKPJTZEQQ-UHFFFAOYSA-N 0.000 claims description 2
PIVSVWSBZQYGPI-UHFFFAOYSA-N 2-[[4-hydroxy-7-(4-methoxyphenoxy)isoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(C(O)=C(N=C2)C(=O)NCC(O)=O)C2=C1 PIVSVWSBZQYGPI-UHFFFAOYSA-N 0.000 claims description 2
FTYAJQMDLQHIKL-UHFFFAOYSA-N 2-[[4-sulfanyl-7-(trifluoromethyl)isoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C(C(F)(F)F)C=CC2=C(S)C(C(=O)NCC(=O)O)=NC=C21 FTYAJQMDLQHIKL-UHFFFAOYSA-N 0.000 claims description 2
KDIMIOTUJKLWOD-UHFFFAOYSA-N 2-[[6-(3,5-difluorophenoxy)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC=C2C=CC=1OC1=CC(F)=CC(F)=C1 KDIMIOTUJKLWOD-UHFFFAOYSA-N 0.000 claims description 2
CDXPIIGUOMPNQV-UHFFFAOYSA-N 2-[[6-(3-fluoro-5-methoxyphenoxy)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound COC1=CC(F)=CC(OC=2C=C3C(O)=C(C(=O)NCC(O)=O)N=CC3=CC=2)=C1 CDXPIIGUOMPNQV-UHFFFAOYSA-N 0.000 claims description 2
ODHBUHIHDIDLHE-UHFFFAOYSA-N 2-[[6-(4-chlorophenoxy)-4-hydroxy-1-methylisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=1C=C2C(C)=NC(C(=O)NCC(O)=O)=C(O)C2=CC=1OC1=CC=C(Cl)C=C1 ODHBUHIHDIDLHE-UHFFFAOYSA-N 0.000 claims description 2
XFBUBCHMRQZHHO-UHFFFAOYSA-N 2-[[6-(4-chlorophenoxy)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC=C2C=CC=1OC1=CC=C(Cl)C=C1 XFBUBCHMRQZHHO-UHFFFAOYSA-N 0.000 claims description 2
OCJDHRJPQLKLIR-UHFFFAOYSA-N 2-[[6-(4-fluorophenoxy)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC=C2C=CC=1OC1=CC=C(F)C=C1 OCJDHRJPQLKLIR-UHFFFAOYSA-N 0.000 claims description 2
CZYLECGAMJILIH-UHFFFAOYSA-N 2-[[6-(benzenesulfinyl)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC=C2C=CC=1S(=O)C1=CC=CC=C1 CZYLECGAMJILIH-UHFFFAOYSA-N 0.000 claims description 2
TYAMDOCBTOJPRP-UHFFFAOYSA-N 2-[[6-(benzenesulfonyl)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC=C2C=CC=1S(=O)(=O)C1=CC=CC=C1 TYAMDOCBTOJPRP-UHFFFAOYSA-N 0.000 claims description 2
AQYUYVIBVJBLPO-UHFFFAOYSA-N 2-[[7-(3-fluoro-5-methoxyphenoxy)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound COC1=CC(F)=CC(OC=2C=C3C=NC(=C(O)C3=CC=2)C(=O)NCC(O)=O)=C1 AQYUYVIBVJBLPO-UHFFFAOYSA-N 0.000 claims description 2
GNITUPICGGJLFJ-UHFFFAOYSA-N 2-[[7-(4-chlorophenoxy)-4-hydroxy-1-methylisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2C(C)=NC(C(=O)NCC(O)=O)=C(O)C2=CC=C1OC1=CC=C(Cl)C=C1 GNITUPICGGJLFJ-UHFFFAOYSA-N 0.000 claims description 2
VEDMHNBWIDHHSU-UHFFFAOYSA-N 2-[carboxymethyl-(1-chloro-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound ClC1=NC(C(=O)N(CC(O)=O)CC(O)=O)=C(O)C2=CC(OC(C)C)=CC=C21 VEDMHNBWIDHHSU-UHFFFAOYSA-N 0.000 claims description 2
YIEWCDQKRVWVCI-UHFFFAOYSA-N 2-[carboxymethyl-(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)N(CC(O)=O)CC(=O)O)=NC(Cl)=C21 YIEWCDQKRVWVCI-UHFFFAOYSA-N 0.000 claims description 2
125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
SWYYJDFYPGMOSY-UHFFFAOYSA-N n-(2-acetamidoethyl)-1-chloro-4-hydroxyisoquinoline-3-carboxamide Chemical compound C1=CC=CC2=C(O)C(C(=O)NCCNC(=O)C)=NC(Cl)=C21 SWYYJDFYPGMOSY-UHFFFAOYSA-N 0.000 claims description 2
GHLVWTMYTYGZBN-UHFFFAOYSA-N n-(2-aminoethyl)-1-chloro-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carboxamide Chemical compound ClC1=NC(C(=O)NCCN)=C(O)C2=CC(OC(C)C)=CC=C21 GHLVWTMYTYGZBN-UHFFFAOYSA-N 0.000 claims description 2
UGMHLZPIICIPEY-UHFFFAOYSA-N n-(2-aminoethyl)-1-chloro-4-hydroxy-7-propan-2-yloxyisoquinoline-3-carboxamide Chemical compound OC1=C(C(=O)NCCN)N=C(Cl)C2=CC(OC(C)C)=CC=C21 UGMHLZPIICIPEY-UHFFFAOYSA-N 0.000 claims description 2
RHLYDTUBALFNLP-UHFFFAOYSA-N n-(2-aminoethyl)-1-chloro-4-hydroxyisoquinoline-3-carboxamide Chemical compound C1=CC=CC2=C(O)C(C(=O)NCCN)=NC(Cl)=C21 RHLYDTUBALFNLP-UHFFFAOYSA-N 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 64
125000004356 hydroxy functional group Chemical group O* 0.000 claims 10
125000000896 monocarboxylic acid group Chemical group 0.000 claims 3
ALMCCXFZTYPBOF-UHFFFAOYSA-N 2-[(1-chloro-4-hydroxy-6-methoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound ClC1=NC(C(=O)NCC(O)=O)=C(O)C2=CC(OC)=CC=C21 ALMCCXFZTYPBOF-UHFFFAOYSA-N 0.000 claims 2
JSBQCFJTJOEUOJ-UHFFFAOYSA-N 2-[(1-chloro-4-hydroxy-7-phenylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC2=C(O)C(C(=O)NCC(=O)O)=NC(Cl)=C2C=C1C1=CC=CC=C1 JSBQCFJTJOEUOJ-UHFFFAOYSA-N 0.000 claims 2
RTSQETJLRNKNPT-UHFFFAOYSA-N 2-[(1-chloro-4-hydroxy-7-propan-2-yloxyisoquinoline-3-carbonyl)-methylamino]acetic acid Chemical compound OC1=C(C(=O)N(C)CC(O)=O)N=C(Cl)C2=CC(OC(C)C)=CC=C21 RTSQETJLRNKNPT-UHFFFAOYSA-N 0.000 claims 2
KEMTZLNIRPGOLO-UHFFFAOYSA-N 2-[(1-ethylsulfanyl-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC=C2C(SCC)=NC(C(=O)NCC(O)=O)=C(O)C2=C1 KEMTZLNIRPGOLO-UHFFFAOYSA-N 0.000 claims 2
FNDPBEBRHOPSBT-UHFFFAOYSA-N 2-[(4-hydroxy-1-methoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC=C2C(OC)=NC(C(=O)NCC(O)=O)=C(O)C2=C1 FNDPBEBRHOPSBT-UHFFFAOYSA-N 0.000 claims 2
ORYLMISPBGLFJW-UHFFFAOYSA-N 2-[(7-bromo-1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=C(Br)C=CC2=C(O)C(C(=O)NCC(=O)O)=NC(Cl)=C21 ORYLMISPBGLFJW-UHFFFAOYSA-N 0.000 claims 2
FKZXWWWVFWASHK-UHFFFAOYSA-N 2-[[1-(3-fluorophenoxy)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=12C=CC=CC2=C(O)C(C(=O)NCC(=O)O)=NC=1OC1=CC=CC(F)=C1 FKZXWWWVFWASHK-UHFFFAOYSA-N 0.000 claims 2
GITWQRJAIJTLTH-UHFFFAOYSA-N 2-[[1-(4-fluorophenoxy)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=12C=CC=CC2=C(O)C(C(=O)NCC(=O)O)=NC=1OC1=CC=C(F)C=C1 GITWQRJAIJTLTH-UHFFFAOYSA-N 0.000 claims 2
UIUUKHDOXNLGIY-UHFFFAOYSA-N 2-[[1-(benzenesulfinyl)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=12C=CC=CC2=C(O)C(C(=O)NCC(=O)O)=NC=1S(=O)C1=CC=CC=C1 UIUUKHDOXNLGIY-UHFFFAOYSA-N 0.000 claims 2
WKIRCIHJYIDICT-UHFFFAOYSA-N 2-[[1-(benzenesulfonyl)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=12C=CC=CC2=C(O)C(C(=O)NCC(=O)O)=NC=1S(=O)(=O)C1=CC=CC=C1 WKIRCIHJYIDICT-UHFFFAOYSA-N 0.000 claims 2
NZHUAHFZAMKAJM-UHFFFAOYSA-N 2-[[1-[(dimethylamino)methyl]-4-hydroxy-7-phenylsulfanylisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2C(CN(C)C)=NC(C(=O)NCC(O)=O)=C(O)C2=CC=C1SC1=CC=CC=C1 NZHUAHFZAMKAJM-UHFFFAOYSA-N 0.000 claims 2
LPEMEZTUAFAAHM-UHFFFAOYSA-N 2-[[1-bromo-4-hydroxy-7-(trifluoromethyl)isoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C(C(F)(F)F)C=CC2=C(O)C(C(=O)NCC(=O)O)=NC(Br)=C21 LPEMEZTUAFAAHM-UHFFFAOYSA-N 0.000 claims 2
WCUBPESBOHYRLD-UHFFFAOYSA-N 2-[[1-chloro-4-hydroxy-7-(4-methoxyphenoxy)isoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(C(O)=C(N=C2Cl)C(=O)NCC(O)=O)C2=C1 WCUBPESBOHYRLD-UHFFFAOYSA-N 0.000 claims 2
KVMFABXFXZTBSN-UHFFFAOYSA-N 2-[[1-chloro-7-(2,6-dimethylphenoxy)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound CC1=CC=CC(C)=C1OC1=CC=C(C(O)=C(N=C2Cl)C(=O)NCC(O)=O)C2=C1 KVMFABXFXZTBSN-UHFFFAOYSA-N 0.000 claims 2
SRTIUYOMKJZLPN-UHFFFAOYSA-N 2-[[4-hydroxy-1-(2-methoxyphenoxy)isoquinoline-3-carbonyl]amino]acetic acid Chemical compound COC1=CC=CC=C1OC1=NC(C(=O)NCC(O)=O)=C(O)C2=CC=CC=C12 SRTIUYOMKJZLPN-UHFFFAOYSA-N 0.000 claims 2
FTMVZYFFFRVDAP-UHFFFAOYSA-N 2-[[4-hydroxy-1-(4-methoxyphenoxy)isoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1OC1=NC(C(=O)NCC(O)=O)=C(O)C2=CC=CC=C12 FTMVZYFFFRVDAP-UHFFFAOYSA-N 0.000 claims 2
RTVZBFHGFMSPPV-UHFFFAOYSA-N 2-[[4-hydroxy-7-[(4-methoxyphenyl)sulfonylamino]isoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=C(C(O)=C(N=C2)C(=O)NCC(O)=O)C2=C1 RTVZBFHGFMSPPV-UHFFFAOYSA-N 0.000 claims 2
YOZBGTLTNGAVFU-UHFFFAOYSA-N roxadustat Chemical compound C1=C2C(C)=NC(C(=O)NCC(O)=O)=C(O)C2=CC=C1OC1=CC=CC=C1 YOZBGTLTNGAVFU-UHFFFAOYSA-N 0.000 claims 2
DNBFVVLLIUHUSX-LLVKDONJSA-N (2r)-6-amino-2-[(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]hexanoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)N[C@H](CCCCN)C(O)=O)=NC(Cl)=C21 DNBFVVLLIUHUSX-LLVKDONJSA-N 0.000 claims 1
SGFRPIDVHYWMID-KRWDZBQOSA-N (2s)-2-[(1-chloro-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carbonyl)amino]-3-(4-hydroxyphenyl)propanoic acid Chemical compound C([C@H](NC(=O)C=1N=C(Cl)C2=CC=C(C=C2C=1O)OC(C)C)C(O)=O)C1=CC=C(O)C=C1 SGFRPIDVHYWMID-KRWDZBQOSA-N 0.000 claims 1
WDKVAOYQIGNKIW-KRWDZBQOSA-N (2s)-2-[(1-chloro-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carbonyl)amino]-3-phenylpropanoic acid Chemical compound C([C@H](NC(=O)C=1N=C(Cl)C2=CC=C(C=C2C=1O)OC(C)C)C(O)=O)C1=CC=CC=C1 WDKVAOYQIGNKIW-KRWDZBQOSA-N 0.000 claims 1
VRUYUVQNAMQHCJ-KRWDZBQOSA-N (2s)-2-[(1-chloro-4-hydroxy-7-propan-2-yloxyisoquinoline-3-carbonyl)amino]-3-(4-hydroxyphenyl)propanoic acid Chemical compound C([C@H](NC(=O)C1=C(O)C2=CC=C(C=C2C(Cl)=N1)OC(C)C)C(O)=O)C1=CC=C(O)C=C1 VRUYUVQNAMQHCJ-KRWDZBQOSA-N 0.000 claims 1
OHJZDNKPKNFUNG-ZDUSSCGKSA-N (2s)-2-[(1-chloro-4-hydroxy-7-propan-2-yloxyisoquinoline-3-carbonyl)amino]-3-methylbutanoic acid Chemical compound OC1=C(C(=O)N[C@@H](C(C)C)C(O)=O)N=C(Cl)C2=CC(OC(C)C)=CC=C21 OHJZDNKPKNFUNG-ZDUSSCGKSA-N 0.000 claims 1
QJWFWOUODUTVCE-LURJTMIESA-N (2s)-2-[(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)N[C@@H](C)C(O)=O)=NC(Cl)=C21 QJWFWOUODUTVCE-LURJTMIESA-N 0.000 claims 1
LYDOLNZHTCXUJR-LBPRGKRZSA-N (2s)-2-[(4-hydroxy-1-methyl-7-phenylsulfanylisoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=CC2=C(O)C(C(=O)N[C@@H](C)C(O)=O)=NC(C)=C2C=C1SC1=CC=CC=C1 LYDOLNZHTCXUJR-LBPRGKRZSA-N 0.000 claims 1
NFJHPAJAWLUUAS-JTQLQIEISA-N (2s)-2-[[6-(4-chlorophenoxy)-4-hydroxyisoquinoline-3-carbonyl]amino]propanoic acid Chemical compound C=1C2=C(O)C(C(=O)N[C@@H](C)C(O)=O)=NC=C2C=CC=1OC1=CC=C(Cl)C=C1 NFJHPAJAWLUUAS-JTQLQIEISA-N 0.000 claims 1
QUOINBQXAQYTOR-UHFFFAOYSA-N 1-[(1-chloro-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carbonyl)amino]cyclopropane-1-carboxylic acid Chemical compound OC=1C2=CC(OC(C)C)=CC=C2C(Cl)=NC=1C(=O)NC1(C(O)=O)CC1 QUOINBQXAQYTOR-UHFFFAOYSA-N 0.000 claims 1
WDEHYUGVPBGBKG-UHFFFAOYSA-N 1-chloro-4-hydroxy-n-(2-hydroxyethyl)-7-propan-2-yloxyisoquinoline-3-carboxamide Chemical compound OC1=C(C(=O)NCCO)N=C(Cl)C2=CC(OC(C)C)=CC=C21 WDEHYUGVPBGBKG-UHFFFAOYSA-N 0.000 claims 1
QCDPBYGFMPOMMA-UHFFFAOYSA-N 1-chloro-n-[2-(dimethylamino)ethyl]-4-hydroxyisoquinoline-3-carboxamide Chemical compound C1=CC=CC2=C(O)C(C(=O)NCCN(C)C)=NC(Cl)=C21 QCDPBYGFMPOMMA-UHFFFAOYSA-N 0.000 claims 1
KHVSLXNRLRKJED-UHFFFAOYSA-N 2-[(1-bromo-4-hydroxy-5-phenylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C12=C(O)C(C(=O)NCC(=O)O)=NC(Br)=C2C=CC=C1C1=CC=CC=C1 KHVSLXNRLRKJED-UHFFFAOYSA-N 0.000 claims 1
UKTNDBCYSASECF-UHFFFAOYSA-N 2-[(1-bromo-4-hydroxy-6-phenoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC(Br)=C2C=CC=1OC1=CC=CC=C1 UKTNDBCYSASECF-UHFFFAOYSA-N 0.000 claims 1
OIRNKGQIXGTENL-UHFFFAOYSA-N 2-[(1-bromo-4-hydroxy-6-phenylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC(Br)=C2C=CC=1C1=CC=CC=C1 OIRNKGQIXGTENL-UHFFFAOYSA-N 0.000 claims 1
MOOCHEISIIMJAU-UHFFFAOYSA-N 2-[(1-bromo-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC2=C(O)C(C(=O)NCC(=O)O)=NC(Br)=C2C=C1OC1=CC=CC=C1 MOOCHEISIIMJAU-UHFFFAOYSA-N 0.000 claims 1
YQNGBSIUZGEBED-UHFFFAOYSA-N 2-[(1-bromo-4-hydroxy-8-phenylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C=CC2=C(O)C(C(=O)NCC(=O)O)=NC(Br)=C2C=1C1=CC=CC=C1 YQNGBSIUZGEBED-UHFFFAOYSA-N 0.000 claims 1
HRCCJZDIEKANKT-UHFFFAOYSA-N 2-[(1-chloro-4-hydroxy-6-iodoisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC(I)=CC2=C(O)C(C(=O)NCC(=O)O)=NC(Cl)=C21 HRCCJZDIEKANKT-UHFFFAOYSA-N 0.000 claims 1
FABNRFHZTJUOBE-UHFFFAOYSA-N 2-[(1-chloro-4-hydroxy-6-phenoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC(Cl)=C2C=CC=1OC1=CC=CC=C1 FABNRFHZTJUOBE-UHFFFAOYSA-N 0.000 claims 1
YZZGDMSQGIGRMB-UHFFFAOYSA-N 2-[(1-chloro-4-hydroxy-6-phenylmethoxyisoquinoline-3-carbonyl)-methylamino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)N(CC(O)=O)C)=NC(Cl)=C2C=CC=1OCC1=CC=CC=C1 YZZGDMSQGIGRMB-UHFFFAOYSA-N 0.000 claims 1
LNZSWDUDMPECOS-UHFFFAOYSA-N 2-[(1-chloro-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carbonyl)-methylamino]acetic acid Chemical compound ClC1=NC(C(=O)N(C)CC(O)=O)=C(O)C2=CC(OC(C)C)=CC=C21 LNZSWDUDMPECOS-UHFFFAOYSA-N 0.000 claims 1
HNKNRBCTSVOMTO-UHFFFAOYSA-N 2-[(1-chloro-4-hydroxy-8-phenylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C=CC2=C(O)C(C(=O)NCC(=O)O)=NC(Cl)=C2C=1C1=CC=CC=C1 HNKNRBCTSVOMTO-UHFFFAOYSA-N 0.000 claims 1
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