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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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Public Health (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
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- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Ophthalmology & Optometry (AREA)
- Gastroenterology & Hepatology (AREA)
- Vascular Medicine (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)
Applications Claiming Priority (2)
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| US76278006P | 2006-01-27 | 2006-01-27 | |
| US60/762,780 | 2006-01-27 |
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| RU2008134664A RU2008134664A (ru) | 2010-03-10 |
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| MX (1) | MX2008009581A (https=) |
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Families Citing this family (54)
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| US8614204B2 (en) * | 2003-06-06 | 2013-12-24 | Fibrogen, Inc. | Enhanced erythropoiesis and iron metabolism |
| WO2004108681A1 (en) | 2003-06-06 | 2004-12-16 | Fibrogen, Inc. | Nitrogen-containing heteroaryl compounds and their use in increasing endogenous erythropoietin |
| BRPI0707302B8 (pt) * | 2006-01-27 | 2021-05-25 | Fibrogen Inc | compostos de cianoisoquinolina que atuam no dano tecidual associado com isquemia, hipóxia e anemia, bem como composição farmacêutica que os compreende |
| WO2007097929A1 (en) * | 2006-02-16 | 2007-08-30 | Fibrogen, Inc. | Compounds and methods for treatment of stroke |
| BRPI0710527B8 (pt) * | 2006-04-04 | 2021-05-25 | Fibrogen Inc | compostos de pirrolo- e tiazolo-piridina e composição farmacêutica que os compreende |
| US8962530B2 (en) * | 2007-06-27 | 2015-02-24 | Regents Of The University Of Colorado | Inflammatory bowel disease therapies |
| WO2009058403A1 (en) * | 2007-11-02 | 2009-05-07 | Fibrogen, Inc. | Methods for reducing blood pressure |
| WO2009073669A1 (en) | 2007-12-03 | 2009-06-11 | Fibrogen, Inc. | Isoxazolopyridine derivatives for use in the treatment of hif-mediated conditions |
| EP2231157A1 (en) * | 2007-12-06 | 2010-09-29 | Fibrogen, Inc. | Methods for increasing endothelial progentior 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 |
| PT2294066E (pt) | 2008-04-28 | 2014-11-21 | Janssen Pharmaceutica Nv | Benzoimidazoles como inibidores da prolil-hidroxilase |
| US8217043B2 (en) * | 2008-08-20 | 2012-07-10 | Fibrogen, Inc. | Compounds and methods for their use |
| WO2010024911A1 (en) * | 2008-08-26 | 2010-03-04 | Fibrogen, Inc. | Methods for increasing neurogenesis |
| JP5649584B2 (ja) * | 2008-11-14 | 2015-01-07 | フィブロジェン インコーポレイテッド | Ｈｉｆヒドロキシラーゼ阻害剤としてのチオクロメン誘導体 |
| US20120301463A1 (en) | 2009-09-30 | 2012-11-29 | President And Fellows Of Harvard College | Methods for Modulation of Autophagy Through the Modulation of Autophagy-Enhancing Gene Products |
| WO2012106472A1 (en) | 2011-02-02 | 2012-08-09 | Fibrogen, Inc. | Naphthyridine derivatives as inhibitors of hypoxia inducible factor (hif) hydroxylase |
| 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 |
| CN104024227B8 (zh) * | 2011-07-22 | 2025-07-29 | 北京贝美拓新药研发有限公司 | 抑制脯氨酸羟化酶活性的化合物的晶型及其应用 |
| GB201113101D0 (en) | 2011-07-28 | 2011-09-14 | Isis Innovation | Assay |
| WO2013063221A1 (en) | 2011-10-25 | 2013-05-02 | Janssen Pharmaceutica Nv | Meglumine salt formulations of 1-(5,6-dichloro-1h-benzo[d]imidazol-2-yl)-1h-pyrazole-4-carboxylic acid |
| WO2013134660A1 (en) | 2012-03-09 | 2013-09-12 | Fibrogen, Inc. | 4 -hydroxy- isoquinoline compounds as hif hydroxylase inhibitors |
| AU2013290438C1 (en) | 2012-07-16 | 2019-01-03 | Kyntra Bio, Inc. | Crystalline forms of the prolyl hydroxylase inhibitor [(4-hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)-amino]-acetic acid |
| US8883823B2 (en) | 2012-07-16 | 2014-11-11 | Fibrogen, Inc. | Crystalline forms of a prolyl hydroxylase inhibitor |
| EP3219706A1 (en) * | 2012-07-16 | 2017-09-20 | Fibrogen, Inc. | Process for making isoquinoline compounds |
| TWI616430B (zh) * | 2012-07-27 | 2018-03-01 | 百健Ｍａ公司 | Ａｔｘ調節劑 |
| AU2014209319B2 (en) * | 2013-01-24 | 2018-04-19 | Fibrogen, Inc. | Crystalline forms of {[1-cyano-5-(4-chlorophenoxy)-4-hydroxy-isoquinoline-3-carbonyl]-amino}-acetic acid |
| HRP20200615T1 (hr) | 2013-06-06 | 2020-07-10 | Fibrogen, Inc. | Farmaceutske formulacije inhibitora hif hidroksilaze |
| 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 |
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| BR112017013440A2 (pt) * | 2014-12-24 | 2018-01-09 | Gilead Sciences, Inc. | compostos de isoquinolina para o tratamento de hiv |
| SG11201705192PA (en) | 2014-12-24 | 2017-07-28 | Gilead Sciences Inc | Fused pyrimidine compounds for the treatment of hiv |
| CN106146395B (zh) | 2015-03-27 | 2019-01-01 | 沈阳三生制药有限责任公司 | 3-羟基吡啶化合物、其制备方法及其制药用途 |
| CN104892509B (zh) * | 2015-06-04 | 2018-03-09 | 苏州明锐医药科技有限公司 | 诺得司他的制备方法 |
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| CN109180580B (zh) | 2016-02-28 | 2021-01-12 | 深圳市塔吉瑞生物医药有限公司 | 一种取代的杂芳基化合物及包含该化合物的组合物及其用途 |
| CN106478503A (zh) * | 2016-09-29 | 2017-03-08 | 上海勋和医药科技有限公司 | Roxadustat中间体的制备方法 |
| CN107954931B (zh) * | 2016-10-17 | 2021-06-22 | 上海医药集团青岛国风药业股份有限公司 | 一种诺得司他的制备方法 |
| CN108017583B (zh) * | 2016-11-01 | 2021-04-06 | 徐州万邦金桥制药有限公司 | 一种可博美的制备方法 |
| CN110878096A (zh) * | 2018-09-05 | 2020-03-13 | 石药集团中奇制药技术（石家庄）有限公司 | 一种1,7-萘啶类衍生物及其制备方法和用途 |
| IT201800009318A1 (it) * | 2018-10-10 | 2020-04-10 | Luigi Frati | Composizioni antiossidanti |
| KR20210108367A (ko) | 2018-11-09 | 2021-09-02 | 비바체 테라퓨틱스, 인크. | 비시클릭 화합물 |
| PY2012000A (es) | 2019-02-26 | 2023-07-25 | Bayer Ag | Derivados de heterociclos bicíclicos fusionados como pesticidas |
| PY2011993A (es) | 2019-02-26 | 2021-07-05 | Bayer Ag | Derivados heterocíclos bicíclicos condensados como plaguicida |
| MX2021012638A (es) | 2019-04-16 | 2022-01-04 | Vivace Therapeutics Inc | Compuestos biciclicos. |
| TWI865563B (zh) | 2019-07-30 | 2024-12-11 | 德商拜耳動物保健有限公司 | 新穎異喹啉衍生物 |
| CN113292494B (zh) * | 2020-02-24 | 2025-12-30 | 苏中药业集团股份有限公司 | 异喹啉羧酸化合物及其制备方法与应用 |
| US12410140B2 (en) * | 2020-06-19 | 2025-09-09 | Jumpcan (Shanghai) Medical Technology Co., Ltd | Method for synthesis of roxadustat and intermediate thereof, and intermediate thereof |
| JP2025500888A (ja) * | 2021-12-17 | 2025-01-15 | アケビア セラピューティクス インコーポレイテッド | 選択的ｐｈｄ１阻害剤としてのピコリンアミド化合物、組成物、及び使用方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2159613C2 (ru) * | 1995-06-06 | 2000-11-27 | Пфайзер Инк. | ЗАМЕЩЕННЫЕ N-(ИНДОЛ-2-КАРБОНИЛ)-β-АЛАНИНАМИДЫ И ИХ ПРОИЗВОДНЫЕ, СПОСОБ ЛЕЧЕНИЯ ГЛИКОГЕНФОСФОРИЛАЗОЗАВИСИМЫХ ЗАБОЛЕВАНИЙ, СПОСОБ ПРЕДУПРЕЖДЕНИЯ ИШЕМИЧЕСКОГО ПОВРЕЖДЕНИЯ МИОКАРДА, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ |
Family Cites Families (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036964A (en) * | 1973-10-11 | 1977-07-19 | Beecham Group Limited | Isocarbostyril-3-carboxylic acid derivatives for the prophylaxis of asthma, hayfever and rhinitis |
| US3989704A (en) * | 1973-10-30 | 1976-11-02 | Sandoz, Inc. | 3-Substituted-4-aryl isoquinolines |
| DE2818423A1 (de) * | 1978-04-27 | 1979-11-08 | Hoechst Ag | Neue isochinolinderivate und verfahren zu ihrer herstellung |
| DE3233424A1 (de) * | 1982-09-09 | 1984-03-15 | Hoechst Ag, 6230 Frankfurt | Isochinolinderivate, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen und ihre verwendung |
| US4559403A (en) * | 1983-05-19 | 1985-12-17 | Hoffmann-La Roche Inc. | Substituted isoquinolines |
| US4584379A (en) * | 1985-01-22 | 1986-04-22 | Merrell Dow Pharmaceuticals Inc. | Isoquinoline thromboxane synthetase inhibitors |
| US4822800A (en) * | 1986-06-09 | 1989-04-18 | Ortho Pharmaceutical Corporation | Isoquinolinol compounds having cardiotonic and phosphodiesterase fraction III inhibiting properties and/or renal vasodilating properties |
| US4966906A (en) * | 1987-11-27 | 1990-10-30 | Hoechst-Roussel Pharmaceuticals Inc. | 1-aryl-3-isoquinolinecarboxamides |
| US4952588A (en) * | 1987-11-27 | 1990-08-28 | Hoechst-Roussel Pharmaceuticals Inc. | 1-aryl-3-quinoline-and 1-aryl-3-isoquinoline-carboxamides |
| EP0532466A3 (en) | 1991-09-12 | 1993-06-16 | Ciba-Geigy Ag | Derivatives of 5-amino-4-hydroxy-hexanoic acid and their therapeutical use |
| EP0626178A1 (de) | 1993-05-17 | 1994-11-30 | Ciba-Geigy Ag | Verwendung von Hemmstoffen von HIV-Aspartatproteasen zur Bekämpfung von Tumorerkrankungen |
| ATE149485T1 (de) | 1993-11-02 | 1997-03-15 | Hoechst Ag | Substituierte heterocyclische carbonsäureamidester, ihre herstellung und ihre verwendung als arzneimittel |
| DK0650961T3 (da) | 1993-11-02 | 1997-09-15 | Hoechst Ag | Substituerede heterocykliske carboxylsyreamider, deres fremstilling og deres anvendelse som lægemidler. |
| NZ270267A (en) * | 1993-12-30 | 1997-03-24 | Hoechst Ag | 3-hydroxypyridin-2yl (and -quinolin-2-yl) carboxamide derivatives and pharmaceutical compositions |
| US5563143A (en) | 1994-09-21 | 1996-10-08 | Pfizer Inc. | Catechol diether compounds as inhibitors of TNF release |
| WO1996018616A1 (en) | 1994-12-12 | 1996-06-20 | Merck & Co., Inc. | Substituted 2-aminopyridines as inhibitors of nitric oxide synthase |
| IL135495A (en) * | 1995-09-28 | 2002-12-01 | Hoechst Ag | Intermediate compounds for the preparation of quinoline-converted amines - 2 - carboxylic acid |
| IL129344A0 (en) * | 1996-11-27 | 2000-02-17 | Du Pont Pharm Co | Novel integrin receptor antagonists |
| AU7526798A (en) | 1997-04-18 | 1998-11-27 | Smithkline Beecham Plc | Acetamide and urea derivatives, process for their preparation and their use in the treatment of cns disorders |
| GB9707830D0 (en) | 1997-04-18 | 1997-06-04 | Smithkline Beecham Plc | Novel compounds |
| DE19746287A1 (de) | 1997-10-20 | 1999-04-22 | Hoechst Marion Roussel De Gmbh | Substituierte Isochinolin-2-Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel |
| FR2779963A1 (fr) * | 1998-06-22 | 1999-12-24 | Centre Nat Rech Scient | Utilisation d'un compose possedant une affinite pour le recepteur mitochondrial des benzodiazepines en therapie du cancer |
| IT1302677B1 (it) * | 1998-10-15 | 2000-09-29 | Zambon Spa | Derivati benzazinici inibitori della fosfodiesterasi 4 |
| WO2000064877A1 (en) * | 1999-04-26 | 2000-11-02 | Neurogen Corporation | 2-aminoquinolinecarboxamides: neurokinin receptor ligands |
| IT1320162B1 (it) | 2000-02-09 | 2003-11-18 | Rotta Research Lab | Derivati della tirosina ad attivita' anti leucotrienica, procedimentoper la loro preparazione e loro uso farmaceutico. |
| US7622503B2 (en) * | 2000-08-24 | 2009-11-24 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
| FI20002044A0 (fi) * | 2000-09-15 | 2000-09-15 | Orion Yhtymae Oyj | Comt-entsyymiä estäviä naftaleenijohdannaisia |
| DE10110750A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| JP4590157B2 (ja) | 2001-03-21 | 2010-12-01 | アイシス イノヴェイション リミテッド | アッセイ、方法および手段 |
| CA2450625A1 (en) * | 2001-06-13 | 2002-12-19 | Genesoft Pharmaceuticals, Inc. | Isoquinoline compounds having antiinfective activity |
| WO2002101073A2 (en) | 2001-06-13 | 2002-12-19 | Genesoft Pharmaceuticals, Inc. | Aryl-benzimidazole compounds having antiinfective activity |
| US7105544B2 (en) * | 2001-07-05 | 2006-09-12 | Synaptic Pharmaceutical Corporation | Substituted alkyl amido piperidines |
| CA2448737C (en) | 2001-07-20 | 2010-06-01 | Boehringer Ingelheim (Canada) Ltd. | Viral polymerase inhibitors |
| EP2335700A1 (en) | 2001-07-25 | 2011-06-22 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis C virus polymerase inhibitors with a heterobicylic structure |
| US7294457B2 (en) | 2001-08-07 | 2007-11-13 | Boehringer Ingelheim (Canada) Ltd. | Direct binding assay for identifying inhibitors of HCV polymerase |
| US6930086B2 (en) | 2001-09-25 | 2005-08-16 | Hoffmann-La Roche Inc. | Diglycosylated erythropoietin |
| US6762318B2 (en) * | 2001-12-03 | 2004-07-13 | Novo Nordisk A/S | Glucagon antagonists |
| DK2298301T3 (en) * | 2001-12-06 | 2018-10-01 | Fibrogen Inc | MEDICINALS FOR TREATMENT OF ANEMIA ASSOCIATED WITH Kidney Disease |
| GB0206711D0 (en) | 2002-03-21 | 2002-05-01 | Isis Innovation | HIF Inhibitor |
| US8124582B2 (en) * | 2002-12-06 | 2012-02-28 | Fibrogen, Inc. | Treatment of diabetes |
| US7618940B2 (en) * | 2002-12-06 | 2009-11-17 | Fibrogen, Inc. | Fat regulation |
| US20060251638A1 (en) * | 2003-06-06 | 2006-11-09 | Volkmar Guenzler-Pukall | Cytoprotection through the use of hif hydroxylase inhibitors |
| US8614204B2 (en) | 2003-06-06 | 2013-12-24 | Fibrogen, Inc. | Enhanced erythropoiesis and iron metabolism |
| WO2004108681A1 (en) * | 2003-06-06 | 2004-12-16 | Fibrogen, Inc. | Nitrogen-containing heteroaryl compounds and their use in increasing endogenous erythropoietin |
| WO2005009962A1 (en) | 2003-07-15 | 2005-02-03 | Merck & Co., Inc. | Hydroxypyridine cgrp receptor antagonists |
| US7544699B2 (en) | 2003-08-08 | 2009-06-09 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds, compositions, and methods of use |
| US7208601B2 (en) * | 2003-08-08 | 2007-04-24 | Mjalli Adnan M M | Aryl and heteroaryl compounds, compositions, and methods of use |
| ZA200610164B (en) | 2004-05-28 | 2008-02-27 | Fibrogen Inc | HIF prolyl hydroxylase activity assay |
| US7248053B2 (en) * | 2004-07-15 | 2007-07-24 | Powerprecise Solutions, Inc. | One time operating state detecting method and apparatus |
| EP1676834A1 (en) | 2004-12-30 | 2006-07-05 | Sanofi-Aventis Deutschland GmbH | Fused bicyclic carboxamide derivates for use as CXCR2 inhibitors in the treatment of inflammation |
| US8703795B2 (en) * | 2005-03-02 | 2014-04-22 | Fibrogen, Inc. | Thienopyridine compounds, and methods of use thereof |
| AU2006254897A1 (en) * | 2005-06-06 | 2006-12-14 | Fibrogen, Inc. | Improved treatment for anemia using a HIF-alpha stabilising agent |
| MX2007016160A (es) * | 2005-06-15 | 2008-03-07 | Fibrogen Inc | Uso de moduladoers de hif-1 alfa para el tratamiento contra el cancer. |
| BRPI0707302B8 (pt) * | 2006-01-27 | 2021-05-25 | Fibrogen Inc | compostos de cianoisoquinolina que atuam no dano tecidual associado com isquemia, hipóxia e anemia, bem como composição farmacêutica que os compreende |
| BRPI0710527B8 (pt) * | 2006-04-04 | 2021-05-25 | Fibrogen Inc | compostos de pirrolo- e tiazolo-piridina e composição farmacêutica que os compreende |
| US20070293575A1 (en) * | 2006-06-15 | 2007-12-20 | Fibrogen, Inc. | Compounds and methods for treatment of cancer-related anemia |
| US7713986B2 (en) * | 2006-06-15 | 2010-05-11 | Fibrogen, Inc. | Compounds and methods for treatment of chemotherapy-induced anemia |
-
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2159613C2 (ru) * | 1995-06-06 | 2000-11-27 | Пфайзер Инк. | ЗАМЕЩЕННЫЕ N-(ИНДОЛ-2-КАРБОНИЛ)-β-АЛАНИНАМИДЫ И ИХ ПРОИЗВОДНЫЕ, СПОСОБ ЛЕЧЕНИЯ ГЛИКОГЕНФОСФОРИЛАЗОЗАВИСИМЫХ ЗАБОЛЕВАНИЙ, СПОСОБ ПРЕДУПРЕЖДЕНИЯ ИШЕМИЧЕСКОГО ПОВРЕЖДЕНИЯ МИОКАРДА, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ |
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