RU2457204C2 - Цианоизохинолиновые соединения (варианты), фармацевтическая композиция на их основе, способ ингибирования активности гидроксилазы гипоксия-индуцибельного фактора (hif) и способ лечения и/или профилактики состояния, связанного с hif, и/или состояния, связанного с эритропоэтином, и/или анемии - Google Patents
Цианоизохинолиновые соединения (варианты), фармацевтическая композиция на их основе, способ ингибирования активности гидроксилазы гипоксия-индуцибельного фактора (hif) и способ лечения и/или профилактики состояния, связанного с hif, и/или состояния, связанного с эритропоэтином, и/или анемии Download PDFInfo
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- RU2457204C2 RU2457204C2 RU2008134664/04A RU2008134664A RU2457204C2 RU 2457204 C2 RU2457204 C2 RU 2457204C2 RU 2008134664/04 A RU2008134664/04 A RU 2008134664/04A RU 2008134664 A RU2008134664 A RU 2008134664A RU 2457204 C2 RU2457204 C2 RU 2457204C2
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- Prior art keywords
- amino
- cyano
- carbonyl
- acetic acid
- group
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract 15
- 108010074633 Mixed Function Oxygenases Proteins 0.000 title claims abstract 9
- 102000008109 Mixed Function Oxygenases Human genes 0.000 title claims abstract 9
- 206010021143 Hypoxia Diseases 0.000 title claims abstract 7
- HJHXYSBRTVFEDD-UHFFFAOYSA-N isoquinoline-1-carbonitrile Chemical class C1=CC=C2C(C#N)=NC=CC2=C1 HJHXYSBRTVFEDD-UHFFFAOYSA-N 0.000 title claims abstract 6
- 208000007502 anemia Diseases 0.000 title claims abstract 3
- 230000002401 inhibitory effect Effects 0.000 title claims abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract 32
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 25
- 239000001257 hydrogen Substances 0.000 claims abstract 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 16
- 125000003118 aryl group Chemical group 0.000 claims abstract 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract 16
- 150000002367 halogens Chemical class 0.000 claims abstract 16
- 125000005842 heteroatom Chemical group 0.000 claims abstract 15
- -1 acryl Chemical group 0.000 claims abstract 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 11
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 8
- 150000002431 hydrogen Chemical class 0.000 claims abstract 8
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims abstract 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 7
- 239000001301 oxygen Substances 0.000 claims abstract 7
- 125000005843 halogen group Chemical group 0.000 claims abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 5
- 150000003839 salts Chemical class 0.000 claims abstract 5
- 102000003951 Erythropoietin Human genes 0.000 claims abstract 4
- 108090000394 Erythropoietin Proteins 0.000 claims abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 4
- 229940105423 erythropoietin Drugs 0.000 claims abstract 4
- 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 claims abstract 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 4
- 230000000694 effects Effects 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 125000001424 substituent group Chemical group 0.000 claims 7
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 230000007954 hypoxia Effects 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- 125000005605 benzo group Chemical group 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 230000001939 inductive effect Effects 0.000 claims 3
- 208000028867 ischemia Diseases 0.000 claims 3
- 230000000302 ischemic effect Effects 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- 108010043005 Prolyl Hydroxylases Proteins 0.000 claims 2
- 102000004079 Prolyl Hydroxylases Human genes 0.000 claims 2
- 125000000613 asparagine group Chemical group N[C@@H](CC(N)=O)C(=O)* 0.000 claims 2
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
- OINOLIGLRWFXAH-LLVKDONJSA-N (2r)-2-[(1-cyano-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(C#N)=C2C=C1OC1=CC=CC=C1 OINOLIGLRWFXAH-LLVKDONJSA-N 0.000 claims 1
- HEEJNIOLTLADLS-LLVKDONJSA-N (2r)-2-[(1-cyano-4-hydroxy-8-phenoxyisoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C=1C=CC2=C(O)C(C(=O)N[C@H](C)C(O)=O)=NC(C#N)=C2C=1OC1=CC=CC=C1 HEEJNIOLTLADLS-LLVKDONJSA-N 0.000 claims 1
- OINOLIGLRWFXAH-NSHDSACASA-N (2s)-2-[(1-cyano-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(C#N)=C2C=C1OC1=CC=CC=C1 OINOLIGLRWFXAH-NSHDSACASA-N 0.000 claims 1
- HEEJNIOLTLADLS-NSHDSACASA-N (2s)-2-[(1-cyano-4-hydroxy-8-phenoxyisoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C=1C=CC2=C(O)C(C(=O)N[C@@H](C)C(O)=O)=NC(C#N)=C2C=1OC1=CC=CC=C1 HEEJNIOLTLADLS-NSHDSACASA-N 0.000 claims 1
- XFDRTANSBXAQCX-ZETCQYMHSA-N (2s)-2-[(1-cyano-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(C#N)=C21 XFDRTANSBXAQCX-ZETCQYMHSA-N 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- PDZURKICFJDDOM-UHFFFAOYSA-N 2-[(1-cyano-4,7-dihydroxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=C(O)C=CC2=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C21 PDZURKICFJDDOM-UHFFFAOYSA-N 0.000 claims 1
- KAYGKLVVYZWVAG-UHFFFAOYSA-N 2-[(1-cyano-4-hydroxy-5-phenoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C12=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C2C=CC=C1OC1=CC=CC=C1 KAYGKLVVYZWVAG-UHFFFAOYSA-N 0.000 claims 1
- JYFBTINVQNCUOS-UHFFFAOYSA-N 2-[(1-cyano-4-hydroxy-5-phenylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C12=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C2C=CC=C1C1=CC=CC=C1 JYFBTINVQNCUOS-UHFFFAOYSA-N 0.000 claims 1
- FBIUHFAZXZTKLZ-UHFFFAOYSA-N 2-[(1-cyano-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(C#N)=C2C=C1OC1=CC=CC=C1 FBIUHFAZXZTKLZ-UHFFFAOYSA-N 0.000 claims 1
- MSQZIWYFGGVXFP-UHFFFAOYSA-N 2-[(1-cyano-4-hydroxy-6-methoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound N#CC1=NC(C(=O)NCC(O)=O)=C(O)C2=CC(OC)=CC=C21 MSQZIWYFGGVXFP-UHFFFAOYSA-N 0.000 claims 1
- HKXSOFOZSVJRHD-UHFFFAOYSA-N 2-[(1-cyano-4-hydroxy-6-phenoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C2C=CC=1OC1=CC=CC=C1 HKXSOFOZSVJRHD-UHFFFAOYSA-N 0.000 claims 1
- DHYMCJJAMYRROZ-UHFFFAOYSA-N 2-[(1-cyano-4-hydroxy-6-phenylsulfanylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C2C=CC=1SC1=CC=CC=C1 DHYMCJJAMYRROZ-UHFFFAOYSA-N 0.000 claims 1
- RGUITKKPHCEUJB-UHFFFAOYSA-N 2-[(1-cyano-4-hydroxy-6-propan-2-yloxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound N#CC1=NC(C(=O)NCC(O)=O)=C(O)C2=CC(OC(C)C)=CC=C21 RGUITKKPHCEUJB-UHFFFAOYSA-N 0.000 claims 1
- QHLJEZMZQWUWAF-UHFFFAOYSA-N 2-[(1-cyano-4-hydroxy-7-methoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound OC1=C(C(=O)NCC(O)=O)N=C(C#N)C2=CC(OC)=CC=C21 QHLJEZMZQWUWAF-UHFFFAOYSA-N 0.000 claims 1
- OOVXTEHRWZLELV-UHFFFAOYSA-N 2-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC2=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C2C=C1OC1=CC=CC=C1 OOVXTEHRWZLELV-UHFFFAOYSA-N 0.000 claims 1
- CHZFBCOJLDUOSX-UHFFFAOYSA-N 2-[(1-cyano-4-hydroxy-7-phenylmethoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC2=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C2C=C1OCC1=CC=CC=C1 CHZFBCOJLDUOSX-UHFFFAOYSA-N 0.000 claims 1
- NLWWCMRQWOUKFR-UHFFFAOYSA-N 2-[(1-cyano-4-hydroxy-7-phenylsulfanylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC2=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C2C=C1SC1=CC=CC=C1 NLWWCMRQWOUKFR-UHFFFAOYSA-N 0.000 claims 1
- ZEJZLPSYVPTCTJ-UHFFFAOYSA-N 2-[(1-cyano-4-hydroxy-7-propan-2-yloxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound OC1=C(C(=O)NCC(O)=O)N=C(C#N)C2=CC(OC(C)C)=CC=C21 ZEJZLPSYVPTCTJ-UHFFFAOYSA-N 0.000 claims 1
- LQINZCHSUDFFAO-UHFFFAOYSA-N 2-[(1-cyano-4-hydroxy-8-phenoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C=CC2=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C2C=1OC1=CC=CC=C1 LQINZCHSUDFFAO-UHFFFAOYSA-N 0.000 claims 1
- FQAPENLFTOTTGL-UHFFFAOYSA-N 2-[(1-cyano-4-hydroxy-8-phenylisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C=CC2=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C2C=1C1=CC=CC=C1 FQAPENLFTOTTGL-UHFFFAOYSA-N 0.000 claims 1
- BJAJGXRKYCBVJL-UHFFFAOYSA-N 2-[(1-cyano-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C21 BJAJGXRKYCBVJL-UHFFFAOYSA-N 0.000 claims 1
- RMTMNJJBCKGPBK-UHFFFAOYSA-N 2-[(1-cyano-4-methoxy-8-phenoxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC=C2C(OC)=C(C(=O)NCC(O)=O)N=C(C#N)C2=C1OC1=CC=CC=C1 RMTMNJJBCKGPBK-UHFFFAOYSA-N 0.000 claims 1
- TUQCVWJJKJPEKG-UHFFFAOYSA-N 2-[(1-cyano-6-cyclohexyloxy-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C2C=CC=1OC1CCCCC1 TUQCVWJJKJPEKG-UHFFFAOYSA-N 0.000 claims 1
- MSKIZMMYIZHWCR-UHFFFAOYSA-N 2-[(6-chloro-1-cyano-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC(Cl)=CC2=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C21 MSKIZMMYIZHWCR-UHFFFAOYSA-N 0.000 claims 1
- WBLKKRDZVHEAAU-UHFFFAOYSA-N 2-[(7-benzyl-1-cyano-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC2=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C2C=C1CC1=CC=CC=C1 WBLKKRDZVHEAAU-UHFFFAOYSA-N 0.000 claims 1
- DKJSLSRAJRSGOE-UHFFFAOYSA-N 2-[(7-butoxy-1-cyano-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound OC1=C(C(=O)NCC(O)=O)N=C(C#N)C2=CC(OCCCC)=CC=C21 DKJSLSRAJRSGOE-UHFFFAOYSA-N 0.000 claims 1
- SDHQACBELYIDMP-UHFFFAOYSA-N 2-[(7-chloro-1-cyano-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=C(Cl)C=CC2=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C21 SDHQACBELYIDMP-UHFFFAOYSA-N 0.000 claims 1
- QZOCAEGKWMHFHD-UHFFFAOYSA-N 2-[[1-cyano-4-hydroxy-6-(2,4,6-trimethylphenoxy)isoquinoline-3-carbonyl]amino]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1OC1=CC=C(C(=NC(C(=O)NCC(O)=O)=C2O)C#N)C2=C1 QZOCAEGKWMHFHD-UHFFFAOYSA-N 0.000 claims 1
- XBVNBYULQKVNHC-UHFFFAOYSA-N 2-[[1-cyano-4-hydroxy-6-(4-methoxyphenoxy)isoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(C(=NC(C(=O)NCC(O)=O)=C2O)C#N)C2=C1 XBVNBYULQKVNHC-UHFFFAOYSA-N 0.000 claims 1
- HCYSKTVEJZHSFD-UHFFFAOYSA-N 2-[[1-cyano-4-hydroxy-6-(4-propoxyphenoxy)isoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CC(OCCC)=CC=C1OC1=CC=C(C(=NC(C(=O)NCC(O)=O)=C2O)C#N)C2=C1 HCYSKTVEJZHSFD-UHFFFAOYSA-N 0.000 claims 1
- FAUBETIXJFVBCH-UHFFFAOYSA-N 2-[[1-cyano-4-hydroxy-6-[(2-methyl-1,3-benzothiazol-6-yl)oxy]isoquinoline-3-carbonyl]amino]acetic acid Chemical compound N#CC1=NC(C(=O)NCC(O)=O)=C(O)C2=CC(OC3=CC=C4N=C(SC4=C3)C)=CC=C21 FAUBETIXJFVBCH-UHFFFAOYSA-N 0.000 claims 1
- GOPZNHXMGANVJK-UHFFFAOYSA-N 2-[[1-cyano-4-hydroxy-6-[(2-methyl-1,3-benzoxazol-6-yl)oxy]isoquinoline-3-carbonyl]amino]acetic acid Chemical compound N#CC1=NC(C(=O)NCC(O)=O)=C(O)C2=CC(OC3=CC=C4N=C(OC4=C3)C)=CC=C21 GOPZNHXMGANVJK-UHFFFAOYSA-N 0.000 claims 1
- YNBFSPIHDGXQNV-UHFFFAOYSA-N 2-[[1-cyano-4-hydroxy-6-[(2-morpholin-4-yl-1,3-benzothiazol-6-yl)oxy]isoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C2C=CC=1OC(C=C1S2)=CC=C1N=C2N1CCOCC1 YNBFSPIHDGXQNV-UHFFFAOYSA-N 0.000 claims 1
- JYRMFIRRDIJDFS-UHFFFAOYSA-N 2-[[1-cyano-4-hydroxy-7-(4-methoxyphenoxy)isoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(C(O)=C(N=C2C#N)C(=O)NCC(O)=O)C2=C1 JYRMFIRRDIJDFS-UHFFFAOYSA-N 0.000 claims 1
- NJRNDFUKRCYEFU-UHFFFAOYSA-N 2-[[1-cyano-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(C#N)=C21 NJRNDFUKRCYEFU-UHFFFAOYSA-N 0.000 claims 1
- DRSMTYDBAZUBFH-UHFFFAOYSA-N 2-[[1-cyano-4-hydroxy-8-(2-methoxyphenoxy)isoquinoline-3-carbonyl]amino]acetic acid Chemical compound COC1=CC=CC=C1OC1=CC=CC2=C(O)C(C(=O)NCC(O)=O)=NC(C#N)=C12 DRSMTYDBAZUBFH-UHFFFAOYSA-N 0.000 claims 1
- SALJCCTTYSIVQA-UHFFFAOYSA-N 2-[[1-cyano-4-hydroxy-8-(3-methoxyphenoxy)isoquinoline-3-carbonyl]amino]acetic acid Chemical compound COC1=CC=CC(OC=2C3=C(C#N)N=C(C(O)=C3C=CC=2)C(=O)NCC(O)=O)=C1 SALJCCTTYSIVQA-UHFFFAOYSA-N 0.000 claims 1
- XDBURKQYHVRVLI-UHFFFAOYSA-N 2-[[1-cyano-4-hydroxy-8-(4-methoxyphenoxy)isoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1OC1=CC=CC2=C(O)C(C(=O)NCC(O)=O)=NC(C#N)=C12 XDBURKQYHVRVLI-UHFFFAOYSA-N 0.000 claims 1
- HSNQLQLDVYPRJG-UHFFFAOYSA-N 2-[[1-cyano-5-(4-fluorophenoxy)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C12=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C2C=CC=C1OC1=CC=C(F)C=C1 HSNQLQLDVYPRJG-UHFFFAOYSA-N 0.000 claims 1
- LJMTUQFYOVLJSE-UHFFFAOYSA-N 2-[[1-cyano-6-(2,3-dihydro-1-benzofuran-5-yloxy)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2OCCC2=CC(OC=2C=CC3=C(C#N)N=C(C(=C3C=2)O)C(=O)NCC(=O)O)=C1 LJMTUQFYOVLJSE-UHFFFAOYSA-N 0.000 claims 1
- VVORUAKDDQLUIX-UHFFFAOYSA-N 2-[[1-cyano-6-(2,6-dimethylphenoxy)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound CC1=CC=CC(C)=C1OC1=CC=C(C(=NC(C(=O)NCC(O)=O)=C2O)C#N)C2=C1 VVORUAKDDQLUIX-UHFFFAOYSA-N 0.000 claims 1
- JMXWSDDALPOIBO-UHFFFAOYSA-N 2-[[1-cyano-6-(2-ethyl-6-methylphenoxy)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound CCC1=CC=CC(C)=C1OC1=CC=C(C(=NC(C(=O)NCC(O)=O)=C2O)C#N)C2=C1 JMXWSDDALPOIBO-UHFFFAOYSA-N 0.000 claims 1
- KVNYGPJHHITWMI-UHFFFAOYSA-N 2-[[1-cyano-6-(4-fluorophenoxy)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C2C=CC=1OC1=CC=C(F)C=C1 KVNYGPJHHITWMI-UHFFFAOYSA-N 0.000 claims 1
- HLLVEWCXEKIHLI-UHFFFAOYSA-N 2-[[1-cyano-7-(2,6-dimethylphenoxy)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound CC1=CC=CC(C)=C1OC1=CC=C(C(O)=C(N=C2C#N)C(=O)NCC(O)=O)C2=C1 HLLVEWCXEKIHLI-UHFFFAOYSA-N 0.000 claims 1
- MCJFKBBQGCQYTJ-UHFFFAOYSA-N 2-[[1-cyano-7-(4-fluorophenoxy)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CC2=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C2C=C1OC1=CC=C(F)C=C1 MCJFKBBQGCQYTJ-UHFFFAOYSA-N 0.000 claims 1
- JKXJZQAZSGNTGM-UHFFFAOYSA-N 2-[[1-cyano-7-[[2-(dimethylamino)-1,3-benzoxazol-5-yl]oxy]-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound OC1=C(C(=O)NCC(O)=O)N=C(C#N)C2=CC(OC=3C=C4N=C(OC4=CC=3)N(C)C)=CC=C21 JKXJZQAZSGNTGM-UHFFFAOYSA-N 0.000 claims 1
- BHLOUTPUFBBGAA-UHFFFAOYSA-N 2-[[1-cyano-8-(4-fluorophenoxy)-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=1C=CC2=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C2C=1OC1=CC=C(F)C=C1 BHLOUTPUFBBGAA-UHFFFAOYSA-N 0.000 claims 1
- YANPNILRMLHKCS-UHFFFAOYSA-N 2-[[6-(1,3-benzodioxol-5-yloxy)-1-cyano-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2OCOC2=CC(OC=2C=CC3=C(C#N)N=C(C(=C3C=2)O)C(=O)NCC(=O)O)=C1 YANPNILRMLHKCS-UHFFFAOYSA-N 0.000 claims 1
- QUYBPKAPSBFZGU-UHFFFAOYSA-N 2-[[6-(4-chloro-2,6-dimethylphenoxy)-1-cyano-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound CC1=CC(Cl)=CC(C)=C1OC1=CC=C(C(=NC(C(=O)NCC(O)=O)=C2O)C#N)C2=C1 QUYBPKAPSBFZGU-UHFFFAOYSA-N 0.000 claims 1
- AHEVSKSJZFZUDM-UHFFFAOYSA-N 2-[[6-(benzenesulfonyl)-1-cyano-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=1C2=C(O)C(C(=O)NCC(=O)O)=NC(C#N)=C2C=CC=1S(=O)(=O)C1=CC=CC=C1 AHEVSKSJZFZUDM-UHFFFAOYSA-N 0.000 claims 1
- SSPYERFPIKHHDF-UHFFFAOYSA-N 2-[[7-(1,3-benzodioxol-5-yloxy)-1-cyano-4-hydroxyisoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2OCOC2=CC(OC2=CC3=C(C#N)N=C(C(=C3C=C2)O)C(=O)NCC(=O)O)=C1 SSPYERFPIKHHDF-UHFFFAOYSA-N 0.000 claims 1
- 206010054936 Cardiac cirrhosis Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 101000881648 Homo sapiens Egl nine homolog 1 Proteins 0.000 claims 1
- 101000881650 Homo sapiens Prolyl hydroxylase EGLN2 Proteins 0.000 claims 1
- 101000881678 Homo sapiens Prolyl hydroxylase EGLN3 Proteins 0.000 claims 1
- 206010022657 Intestinal infarction Diseases 0.000 claims 1
- 208000032382 Ischaemic stroke Diseases 0.000 claims 1
- 208000010378 Pulmonary Embolism Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000020832 chronic kidney disease Diseases 0.000 claims 1
- 208000022831 chronic renal failure syndrome Diseases 0.000 claims 1
- 102000053692 human EGLN1 Human genes 0.000 claims 1
- 102000048660 human EGLN2 Human genes 0.000 claims 1
- 102000050122 human EGLN3 Human genes 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000000977 initiatory effect Effects 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- ISUSJVGCVSHSAK-UHFFFAOYSA-N methyl 2-[(1-cyano-4-methoxy-8-phenoxyisoquinoline-3-carbonyl)amino]acetate Chemical compound C=1C=CC2=C(OC)C(C(=O)NCC(=O)OC)=NC(C#N)=C2C=1OC1=CC=CC=C1 ISUSJVGCVSHSAK-UHFFFAOYSA-N 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000000451 tissue damage Effects 0.000 claims 1
- 231100000827 tissue damage Toxicity 0.000 claims 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 9
- 125000005915 C6-C14 aryl group Chemical group 0.000 abstract 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 230000004071 biological effect Effects 0.000 abstract 1
- WDXARTMCIRVMAE-UHFFFAOYSA-N quinoline-2-carbonitrile Chemical class C1=CC=CC2=NC(C#N)=CC=C21 WDXARTMCIRVMAE-UHFFFAOYSA-N 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
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- Gastroenterology & Hepatology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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| PL1644336T3 (pl) | 2003-06-06 | 2011-07-29 | Fibrogen Inc | Związki heteroarylowe zawierające azot i ich zastosowanie w zwiększaniu poziomu endogennej erytropoetyny |
| US8614204B2 (en) * | 2003-06-06 | 2013-12-24 | Fibrogen, Inc. | Enhanced erythropoiesis and iron metabolism |
| KR101446499B1 (ko) * | 2006-01-27 | 2014-10-06 | 피브로겐, 인크. | 저산소증 유발가능 인자(ｈｉｆ)를 안정시키는 시아노이소퀴놀린 화합물 |
| AU2007218051A1 (en) * | 2006-02-16 | 2007-08-30 | Fibrogen, Inc. | Compounds and methods for treatment of stroke |
| CA2647596C (en) * | 2006-04-04 | 2012-06-12 | Fibrogen, Inc. | Pyrrolo- and thiazolo-pyridine compounds as hif modulators |
| WO2009002533A1 (en) * | 2007-06-27 | 2008-12-31 | The Brigham And Women's Hospital, Inc. | Inflammatory bowel disease therapies |
| US20110039878A1 (en) * | 2007-11-02 | 2011-02-17 | Volkmar Guenzler-Pukall | Methods for reducing blood pressure |
| US8269008B2 (en) * | 2007-12-03 | 2012-09-18 | Fibrogen, Inc. | Oxazolopyridine and isoxazolopyridine derivatives for use in the treatment of HIF-mediated conditions |
| US20110039885A1 (en) * | 2007-12-06 | 2011-02-17 | Fibrogen, Inc. | Methods for increasing endothelial progenitor cells |
| WO2009075826A1 (en) * | 2007-12-07 | 2009-06-18 | Fibrogen, Inc. | Methods for increasing white blood cells |
| EP2252619B1 (en) | 2008-01-11 | 2013-10-09 | Fibrogen, Inc. | Isothiazole-pyridine derivatives as modulators of hif (hypoxia inducible factor) activity |
| WO2009100250A1 (en) | 2008-02-05 | 2009-08-13 | Fibrogen, Inc. | Chromene derivatives and use thereof as hif hydroxylase activity inhibitors |
| ES2524883T3 (es) * | 2008-03-18 | 2014-12-15 | Merck Sharp & Dohme Corp. | 4-Hidroxipirimidina-5-carboxamidas sustituidas |
| WO2009134750A1 (en) | 2008-04-28 | 2009-11-05 | Janssen Pharmaceutica Nv | Benzoimidazoles as prolyl hydroxylase inhibitors |
| EP2334682B1 (en) | 2008-08-20 | 2017-10-04 | Fibrogen, Inc. | Pyrrolo [ 1, 2 -b] pyridazine derivatives and their use as hif modulators |
| WO2010024911A1 (en) * | 2008-08-26 | 2010-03-04 | Fibrogen, Inc. | Methods for increasing neurogenesis |
| EP2370422B1 (en) | 2008-11-14 | 2019-06-05 | Fibrogen, Inc. | Thiochromene derivatives as hif hydroxylase inhibitors |
| EP2483406A2 (en) | 2009-09-30 | 2012-08-08 | President and Fellows of Harvard College | Methods for modulation of autophagy through the modulation of autophagy-inhibiting gene products |
| EP2670750B1 (en) | 2011-02-02 | 2016-09-14 | Fibrogen, Inc. | Naphthyridine derivatives as inhibitors of hypoxia inducible factor |
| GB201102659D0 (en) | 2011-02-15 | 2011-03-30 | Isis Innovation | Assay |
| WO2012150221A2 (de) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Neue halogenierte benzylalkoholester der cyclopropancarbonsäure als schädlingsbekämpfungsmittel |
| WO2012150208A1 (de) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Verwendung von substituierten benzylalkoholestern der cyclopropancarbonsäure zur bekämpfung von insektizid-resistenten insekten |
| KR102029951B1 (ko) * | 2011-07-22 | 2019-11-08 | 베이징 베타 파머수티컬 컴퍼니 리미티드 | 프로릴 히드록실라제 억제제로서 화합물의 다형체형, 및 이의 용도 |
| GB201113101D0 (en) | 2011-07-28 | 2011-09-14 | Isis Innovation | Assay |
| ES2818977T3 (es) | 2011-10-25 | 2021-04-14 | Janssen Pharmaceutica Nv | Método para obtener cristales de sal de meglumina de ácido 1-(5,6-dicloro-1H-benzo[d]imidazol-2-il)-1H-pirazol-4-carboxílico |
| NZ700760A (en) | 2012-03-09 | 2016-08-26 | Fibrogen Inc | 4 -hydroxy- isoquinoline compounds as hif hydroxylase inhibitors |
| US8883823B2 (en) | 2012-07-16 | 2014-11-11 | Fibrogen, Inc. | Crystalline forms of a prolyl hydroxylase inhibitor |
| SG10201700873UA (en) | 2012-07-16 | 2017-04-27 | Fibrogen Inc | Crystalline forms of the prolyl hydroxylase inhibitor [(4-hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)-amino]-acetic acid |
| CA2879238C (en) | 2012-07-16 | 2021-08-10 | Fibrogen, Inc. | Process for making isoquinoline compounds |
| ES2668694T3 (es) * | 2012-07-27 | 2018-05-21 | Biogen Ma Inc. | Derivados de ácido 1-[7-(cis-4-metil-ciclohexiloxi)-8-trifluorometil-naftalen-2-ilmetil]-piperidin-4-carboxílico como moduladores de autotaxina (ATX) para tratar inflamaciones y trastornos autoinmunitarios |
| JP6437456B2 (ja) * | 2013-01-24 | 2018-12-12 | フィブロジェン インコーポレイテッド | ｛［１−シアノ−５−（４−クロロフェノキシ）−４−ヒドロキシ−イソキノリン−３−カルボニル］−アミノ｝−酢酸の結晶形態 |
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| EP2915878A1 (en) | 2014-03-07 | 2015-09-09 | Institut Pasteur | Method and device for conserving viable and functional human polymorphonuclear neutrophils |
| WO2016034108A1 (zh) | 2014-09-02 | 2016-03-10 | 广东东阳光药业有限公司 | 喹啉酮类化合物及其应用 |
| TWI770552B (zh) | 2014-12-24 | 2022-07-11 | 美商基利科學股份有限公司 | 喹唑啉化合物 |
| PT3237397T (pt) * | 2014-12-24 | 2019-02-08 | Gilead Sciences Inc | Compostos de isoquinolina para o tratamento de hiv |
| JP6385584B2 (ja) | 2014-12-24 | 2018-09-05 | ギリアード サイエンシーズ， インコーポレイテッド | Ｈｉｖの処置のための縮合ピリミジン化合物 |
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