DE60202452C5 - Pyridazinonaldose reductase inhibitoren - Google Patents
Pyridazinonaldose reductase inhibitoren Download PDFInfo
- Publication number
- DE60202452C5 DE60202452C5 DE60202452T DE60202452T DE60202452C5 DE 60202452 C5 DE60202452 C5 DE 60202452C5 DE 60202452 T DE60202452 T DE 60202452T DE 60202452 T DE60202452 T DE 60202452T DE 60202452 C5 DE60202452 C5 DE 60202452C5
- Authority
- DE
- Germany
- Prior art keywords
- pyridazin
- alkyl
- sulfonyl
- het
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 239000003112 inhibitor Substances 0.000 title 1
- -1 pyrazinopyrazinyl Chemical group 0.000 claims abstract 146
- 150000001875 compounds Chemical class 0.000 claims abstract 29
- 239000000651 prodrug Substances 0.000 claims abstract 28
- 229940002612 prodrug Drugs 0.000 claims abstract 28
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract 17
- 125000000842 isoxazolyl group Chemical group 0.000 claims abstract 17
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract 17
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract 17
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract 16
- 150000003839 salts Chemical class 0.000 claims abstract 14
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims abstract 13
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims abstract 13
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims abstract 13
- 125000002541 furyl group Chemical group 0.000 claims abstract 13
- 125000005956 isoquinolyl group Chemical group 0.000 claims abstract 13
- 125000001715 oxadiazolyl group Chemical group 0.000 claims abstract 13
- 125000002098 pyridazinyl group Chemical group 0.000 claims abstract 13
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 13
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract 13
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract 13
- 125000001113 thiadiazolyl group Chemical group 0.000 claims abstract 13
- 125000001544 thienyl group Chemical group 0.000 claims abstract 13
- 125000001425 triazolyl group Chemical group 0.000 claims abstract 13
- 125000005493 quinolyl group Chemical group 0.000 claims abstract 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 11
- 239000001257 hydrogen Substances 0.000 claims abstract 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 3
- 125000003118 aryl group Chemical group 0.000 claims abstract 3
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims abstract 3
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims abstract 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract 3
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims abstract 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims abstract 3
- 125000001041 indolyl group Chemical group 0.000 claims abstract 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims abstract 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims abstract 3
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims abstract 3
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims abstract 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract 3
- 125000006085 pyrrolopyridyl group Chemical group 0.000 claims abstract 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims abstract 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims abstract 3
- 125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 claims abstract 3
- 125000001424 substituent group Chemical group 0.000 claims 28
- 125000001153 fluoro group Chemical group F* 0.000 claims 26
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 125000005554 pyridyloxy group Chemical group 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 125000001624 naphthyl group Chemical group 0.000 claims 8
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 239000000460 chlorine Substances 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 4
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 3
- FXFPQPNUMWQRAO-UHFFFAOYSA-N 6-[(5-chloro-3-methyl-1-benzofuran-2-yl)sulfonyl]pyridazin-3(2h)-one Chemical compound O1C2=CC=C(Cl)C=C2C(C)=C1S(=O)(=O)C=1C=CC(=O)NN=1 FXFPQPNUMWQRAO-UHFFFAOYSA-N 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- BVGVSUYAYNIIGE-UHFFFAOYSA-N 3-[(5-fluoro-3-methyl-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound O1C2=CC=C(F)C=C2C(C)=C1S(=O)(=O)C=1C=CC(=O)NN=1 BVGVSUYAYNIIGE-UHFFFAOYSA-N 0.000 claims 2
- DXMRTFOZJATGPZ-UHFFFAOYSA-N 3-[[3-methyl-5-(trifluoromethyl)-1-benzofuran-2-yl]sulfonyl]-1h-pyridazin-6-one Chemical compound O1C2=CC=C(C(F)(F)F)C=C2C(C)=C1S(=O)(=O)C=1C=CC(=O)NN=1 DXMRTFOZJATGPZ-UHFFFAOYSA-N 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims 2
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims 1
- UIJXWCKFKVXTRU-UHFFFAOYSA-N 2-[(6-oxo-1h-pyridazin-3-yl)sulfonyl]-5h-furo[3,2-c]pyridin-4-one Chemical compound N1C(=O)C=CC(S(=O)(=O)C=2OC3=C(C(NC=C3)=O)C=2)=N1 UIJXWCKFKVXTRU-UHFFFAOYSA-N 0.000 claims 1
- WFJJYKJYGCGPFS-UHFFFAOYSA-N 3-(1-benzylindol-5-yl)sulfonyl-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)C=2C=C3C=CN(CC=4C=CC=CC=4)C3=CC=2)=N1 WFJJYKJYGCGPFS-UHFFFAOYSA-N 0.000 claims 1
- YVEUDWZQMUISKP-UHFFFAOYSA-N 3-(1-methylindol-2-yl)sulfonyl-1h-pyridazin-6-one Chemical compound C=1C2=CC=CC=C2N(C)C=1S(=O)(=O)C=1C=CC(=O)NN=1 YVEUDWZQMUISKP-UHFFFAOYSA-N 0.000 claims 1
- HXNAGYMCTAINEA-UHFFFAOYSA-N 3-(1h-indol-2-ylsulfonyl)-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)C=2NC3=CC=CC=C3C=2)=N1 HXNAGYMCTAINEA-UHFFFAOYSA-N 0.000 claims 1
- ZCHJRGKQXZDDOT-UHFFFAOYSA-N 3-(1h-indol-3-ylsulfonyl)-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)C=2C3=CC=CC=C3NC=2)=N1 ZCHJRGKQXZDDOT-UHFFFAOYSA-N 0.000 claims 1
- NQJFBHVHPOEWLC-UHFFFAOYSA-N 3-(3,4,4a,5-tetrahydro-2h-quinolin-1-ylsulfonyl)-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)N2C3=CC=CCC3CCC2)=N1 NQJFBHVHPOEWLC-UHFFFAOYSA-N 0.000 claims 1
- ULUKHVCKTFCDRT-UHFFFAOYSA-N 3-(3-chloroindazol-1-yl)sulfonyl-1h-pyridazin-6-one Chemical compound C12=CC=CC=C2C(Cl)=NN1S(=O)(=O)C=1C=CC(=O)NN=1 ULUKHVCKTFCDRT-UHFFFAOYSA-N 0.000 claims 1
- MUEYUVJYJZJUIE-UHFFFAOYSA-N 3-(3-chloroindol-1-yl)sulfonyl-1h-pyridazin-6-one Chemical compound C12=CC=CC=C2C(Cl)=CN1S(=O)(=O)C=1C=CC(=O)NN=1 MUEYUVJYJZJUIE-UHFFFAOYSA-N 0.000 claims 1
- FFQYWMOJPDVLPU-UHFFFAOYSA-N 3-(3-methylindol-1-yl)sulfonyl-1h-pyridazin-6-one Chemical compound C12=CC=CC=C2C(C)=CN1S(=O)(=O)C=1C=CC(=O)NN=1 FFQYWMOJPDVLPU-UHFFFAOYSA-N 0.000 claims 1
- LCVXWZKNHISEPA-UHFFFAOYSA-N 3-(5h-[1,3]dioxolo[4,5-f]indol-6-ylsulfonyl)-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)C=2NC3=CC=4OCOC=4C=C3C=2)=N1 LCVXWZKNHISEPA-UHFFFAOYSA-N 0.000 claims 1
- NTJWJLZMOKBOFA-UHFFFAOYSA-N 3-[(3,5-dimethyl-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound O1C2=CC=C(C)C=C2C(C)=C1S(=O)(=O)C=1C=CC(=O)NN=1 NTJWJLZMOKBOFA-UHFFFAOYSA-N 0.000 claims 1
- SOVXTIRUOWJZSS-UHFFFAOYSA-N 3-[(3-chloro-1h-indol-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound N1C2=CC=CC=C2C(Cl)=C1S(=O)(=O)C=1C=CC(=O)NN=1 SOVXTIRUOWJZSS-UHFFFAOYSA-N 0.000 claims 1
- CABVMWOKBSURKS-UHFFFAOYSA-N 3-[(3-hydroxy-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound O1C2=CC=CC=C2C(O)=C1S(=O)(=O)C=1C=CC(=O)NN=1 CABVMWOKBSURKS-UHFFFAOYSA-N 0.000 claims 1
- HTJQFBOZQJFYDR-UHFFFAOYSA-N 3-[(3-methyl-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound O1C2=CC=CC=C2C(C)=C1S(=O)(=O)C=1C=CC(=O)NN=1 HTJQFBOZQJFYDR-UHFFFAOYSA-N 0.000 claims 1
- YWFVMRGAGDNRMA-UHFFFAOYSA-N 3-[(3-phenyl-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)C2=C(C3=CC=CC=C3O2)C=2C=CC=CC=2)=N1 YWFVMRGAGDNRMA-UHFFFAOYSA-N 0.000 claims 1
- OLKIXQGJDUXXTC-UHFFFAOYSA-N 3-[(5,7-dichloro-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound C=1C2=CC(Cl)=CC(Cl)=C2OC=1S(=O)(=O)C=1C=CC(=O)NN=1 OLKIXQGJDUXXTC-UHFFFAOYSA-N 0.000 claims 1
- ZDIDXSOYTUCPQE-UHFFFAOYSA-N 3-[(5-chloro-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound C=1C2=CC(Cl)=CC=C2OC=1S(=O)(=O)C=1C=CC(=O)NN=1 ZDIDXSOYTUCPQE-UHFFFAOYSA-N 0.000 claims 1
- WGSUFIBFKNDTGJ-UHFFFAOYSA-N 3-[(5-chloro-1h-indol-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound C=1C2=CC(Cl)=CC=C2NC=1S(=O)(=O)C=1C=CC(=O)NN=1 WGSUFIBFKNDTGJ-UHFFFAOYSA-N 0.000 claims 1
- DDADXEQGUNIKPT-UHFFFAOYSA-N 3-[(5-chloro-3-ethyl-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound O1C2=CC=C(Cl)C=C2C(CC)=C1S(=O)(=O)C=1C=CC(=O)NN=1 DDADXEQGUNIKPT-UHFFFAOYSA-N 0.000 claims 1
- MDZSNXLRKIMZRY-UHFFFAOYSA-N 3-[(5-chloro-3-hydroxy-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound O1C2=CC=C(Cl)C=C2C(O)=C1S(=O)(=O)C=1C=CC(=O)NN=1 MDZSNXLRKIMZRY-UHFFFAOYSA-N 0.000 claims 1
- CYXNLUKXQVTYHT-UHFFFAOYSA-N 3-[(5-chloro-3-methyl-1-benzofuran-2-yl)sulfanyl]-6-methoxypyridazine Chemical compound N1=NC(OC)=CC=C1SC1=C(C)C2=CC(Cl)=CC=C2O1 CYXNLUKXQVTYHT-UHFFFAOYSA-N 0.000 claims 1
- GTSQOJISPPCBEE-UHFFFAOYSA-N 3-[(5-chloro-3-methyl-1-benzofuran-2-yl)sulfinyl]-6-methoxypyridazine Chemical compound N1=NC(OC)=CC=C1S(=O)C1=C(C)C2=CC(Cl)=CC=C2O1 GTSQOJISPPCBEE-UHFFFAOYSA-N 0.000 claims 1
- PESVWIXUZNFVOB-UHFFFAOYSA-N 3-[(5-chloro-3-methyl-1-benzofuran-2-yl)sulfonyl]-6-methoxypyridazine Chemical compound N1=NC(OC)=CC=C1S(=O)(=O)C1=C(C)C2=CC(Cl)=CC=C2O1 PESVWIXUZNFVOB-UHFFFAOYSA-N 0.000 claims 1
- JOGGJDKLNQCAQJ-UHFFFAOYSA-N 3-[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound S1C2=CC=C(Cl)C=C2C(C)=C1S(=O)(=O)C=1C=CC(=O)NN=1 JOGGJDKLNQCAQJ-UHFFFAOYSA-N 0.000 claims 1
- MVDAJCXOQBRPQC-UHFFFAOYSA-N 3-[(5-chloro-3-propan-2-yl-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound O1C2=CC=C(Cl)C=C2C(C(C)C)=C1S(=O)(=O)C=1C=CC(=O)NN=1 MVDAJCXOQBRPQC-UHFFFAOYSA-N 0.000 claims 1
- BRGJYGOQKYCMGP-UHFFFAOYSA-N 3-[(5-methoxy-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound C=1C2=CC(OC)=CC=C2OC=1S(=O)(=O)C=1C=CC(=O)NN=1 BRGJYGOQKYCMGP-UHFFFAOYSA-N 0.000 claims 1
- IIWJPLYZNNZNGB-UHFFFAOYSA-N 3-[(5-methoxy-1h-indol-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound C=1C2=CC(OC)=CC=C2NC=1S(=O)(=O)C=1C=CC(=O)NN=1 IIWJPLYZNNZNGB-UHFFFAOYSA-N 0.000 claims 1
- QSROOXVEHSOUBU-UHFFFAOYSA-N 3-[(5-methyl-1-benzothiophen-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound C=1C2=CC(C)=CC=C2SC=1S(=O)(=O)C=1C=CC(=O)NN=1 QSROOXVEHSOUBU-UHFFFAOYSA-N 0.000 claims 1
- YCAYZFGZUUVLMY-UHFFFAOYSA-N 3-[(6-chloro-1h-indol-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound N1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)C=1C=CC(=O)NN=1 YCAYZFGZUUVLMY-UHFFFAOYSA-N 0.000 claims 1
- VTAPFQFGVVPFNM-UHFFFAOYSA-N 3-[(6-chloro-3-methyl-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound O1C2=CC(Cl)=CC=C2C(C)=C1S(=O)(=O)C=1C=CC(=O)NN=1 VTAPFQFGVVPFNM-UHFFFAOYSA-N 0.000 claims 1
- PGWALDLWZWXTRU-UHFFFAOYSA-N 3-[(6-fluoro-1h-indol-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound N1C2=CC(F)=CC=C2C=C1S(=O)(=O)C=1C=CC(=O)NN=1 PGWALDLWZWXTRU-UHFFFAOYSA-N 0.000 claims 1
- VOZMFKBTMUXWCT-UHFFFAOYSA-N 3-[(7-chloro-1h-indol-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound N1C=2C(Cl)=CC=CC=2C=C1S(=O)(=O)C=1C=CC(=O)NN=1 VOZMFKBTMUXWCT-UHFFFAOYSA-N 0.000 claims 1
- GJSIXQDXGNTUSN-UHFFFAOYSA-N 3-[[3-(4-fluorophenyl)-1-benzofuran-2-yl]sulfonyl]-1h-pyridazin-6-one Chemical compound C1=CC(F)=CC=C1C1=C(S(=O)(=O)C2=NNC(=O)C=C2)OC2=CC=CC=C12 GJSIXQDXGNTUSN-UHFFFAOYSA-N 0.000 claims 1
- BCXKKVQJDYCMAD-UHFFFAOYSA-N 3-indol-1-ylsulfonyl-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)N2C3=CC=CC=C3C=C2)=N1 BCXKKVQJDYCMAD-UHFFFAOYSA-N 0.000 claims 1
- NTGNYOSDAOGFDV-UHFFFAOYSA-N 3-pyridin-2-ylsulfinyl-1H-pyridazin-6-one Chemical compound N1=C(C=CC=C1)S(=O)C=1C=CC(NN=1)=O NTGNYOSDAOGFDV-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- TWBJWMKHMNWGNT-UHFFFAOYSA-N 3-pyrrol-1-ylsulfonyl-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)N2C=CC=C2)=N1 TWBJWMKHMNWGNT-UHFFFAOYSA-N 0.000 claims 1
- CJENBJORWKGVTB-UHFFFAOYSA-N 3-thieno[2,3-b]pyridin-2-ylsulfonyl-1H-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)C=2SC3=NC=CC=C3C=2)=N1 CJENBJORWKGVTB-UHFFFAOYSA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 1
- 208000002177 Cataract Diseases 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 1
- 208000032781 Diabetic cardiomyopathy Diseases 0.000 claims 1
- 206010063547 Diabetic macroangiopathy Diseases 0.000 claims 1
- 206010054044 Diabetic microangiopathy Diseases 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 208000003790 Foot Ulcer Diseases 0.000 claims 1
- 125000004534 benzothien-2-yl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 201000009101 diabetic angiopathy Diseases 0.000 claims 1
- 208000033679 diabetic kidney disease Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 210000005003 heart tissue Anatomy 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 1
- 125000004536 indazol-1-yl group Chemical group N1(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 0 CC(C(**)=NN1)=C(C)C1=O Chemical compound CC(C(**)=NN1)=C(C)C1=O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28005101P | 2001-03-30 | 2001-03-30 | |
| US280051P | 2001-03-30 | ||
| PCT/IB2002/000320 WO2002079198A1 (en) | 2001-03-30 | 2002-01-31 | Pyridazinone aldose reductase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE60202452D1 DE60202452D1 (de) | 2005-02-03 |
| DE60202452T2 DE60202452T2 (de) | 2006-02-09 |
| DE60202452C5 true DE60202452C5 (de) | 2006-11-23 |
Family
ID=23071435
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60202452T Expired - Fee Related DE60202452C5 (de) | 2001-03-30 | 2002-01-31 | Pyridazinonaldose reductase inhibitoren |
| DE60216823T Expired - Fee Related DE60216823T2 (de) | 2001-03-30 | 2002-01-31 | Zwischenprodukten für die Herstellung von Pyridazinon Aldose Reductase Inhibitoren. |
| DE60217930T Expired - Fee Related DE60217930T2 (de) | 2001-03-30 | 2002-01-31 | Pyridazinon Aldose Reductase Inhibitoren |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60216823T Expired - Fee Related DE60216823T2 (de) | 2001-03-30 | 2002-01-31 | Zwischenprodukten für die Herstellung von Pyridazinon Aldose Reductase Inhibitoren. |
| DE60217930T Expired - Fee Related DE60217930T2 (de) | 2001-03-30 | 2002-01-31 | Pyridazinon Aldose Reductase Inhibitoren |
Country Status (43)
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6001876A (en) | 1996-07-24 | 1999-12-14 | Warner-Lambert Company | Isobutylgaba and its derivatives for the treatment of pain |
| ES2240657T3 (es) * | 2001-02-28 | 2005-10-16 | Pfizer Products Inc. | Compuestos de sulfonilpiridazinona utiles como inhibidores de aldosa reductasa. |
| ATE348100T1 (de) * | 2001-03-30 | 2007-01-15 | Pfizer Prod Inc | Zwischenprodukten für die herstellung von pyridazinon aldose reductase inhibitoren. |
| AU761191B2 (en) * | 2001-05-24 | 2003-05-29 | Pfizer Products Inc. | Therapies for tissue damage resulting from ischemia |
| CN1269814C (zh) | 2002-01-09 | 2006-08-16 | 辉瑞产品公司 | 哒嗪酮抗糖尿病药的制备方法和中间体 |
| US20040092522A1 (en) * | 2002-08-15 | 2004-05-13 | Field Mark John | Synergistic combinations |
| US7419981B2 (en) * | 2002-08-15 | 2008-09-02 | Pfizer Inc. | Synergistic combinations of an alpha-2-delta ligand and a cGMP phosphodieterse 5 inhibitor |
| US6872833B2 (en) * | 2003-04-14 | 2005-03-29 | Hoffmann-La Roche Inc. | Adenosine receptor ligands |
| US8017634B2 (en) | 2003-12-29 | 2011-09-13 | President And Fellows Of Harvard College | Compositions for treating obesity and insulin resistance disorders |
| US7262318B2 (en) * | 2004-03-10 | 2007-08-28 | Pfizer, Inc. | Substituted heteroaryl- and phenylsulfamoyl compounds |
| PE20060272A1 (es) | 2004-05-24 | 2006-05-22 | Glaxo Group Ltd | (2r,3r,4s,5r,2'r,3'r,4's,5's)-2,2'-{trans-1,4-ciclohexanodiilbis-[imino(2-{[2-(1-metil-1h-imidazol-4-il)etil]amino}-9h-purin-6,9-diil)]}bis[5-(2-etil-2h-tetrazol-5-il)tetrahidro-3,4-furanodiol] como agonista a2a |
| CA2568640C (en) | 2004-06-04 | 2011-08-09 | Teva Pharmaceutical Industries Ltd. | Pharmaceutical composition containing irbesartan |
| US20050288340A1 (en) * | 2004-06-29 | 2005-12-29 | Pfizer Inc | Substituted heteroaryl- and phenylsulfamoyl compounds |
| US20060035251A1 (en) * | 2004-06-30 | 2006-02-16 | Whitehead Institute For Biomedical Research | Novel methods for high-throughput genome-wide location analysis |
| GB0514809D0 (en) | 2005-07-19 | 2005-08-24 | Glaxo Group Ltd | Compounds |
| US7741317B2 (en) | 2005-10-21 | 2010-06-22 | Bristol-Myers Squibb Company | LXR modulators |
| US7888376B2 (en) | 2005-11-23 | 2011-02-15 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
| BRPI0706523A2 (pt) * | 2006-01-13 | 2011-01-04 | Wyeth Corp | composto de fórmula i; composição farmacêutica; método de tratamento de distúrbios que estão relacionados com ou são afetados pela inibição da recaptação de norepinefrina, o receptor de 5-ht6 ou o receptor de 5-ht2a; método de tratamento de um distúrbio de aprendizado, de um distúrbio cognitivo, de um distúrbio de memória, de um distúrbio de personalidade, de um distúrbio comportamental, de um distúrbio de movimento, de um distúrbio neurodegenerativo, de abstinência de droga, de distúrbio de sono, de um distúrbio alimentar, de uma toxicidade de droga aguda, de um distúrbio cardiovascular, de uma disfunção sexual, de um distúrbio gastrintestinal, de um distúrbio genitourinário, de um distúrbio de dor, de um distúrbio nervoso ou de um distúrbio de sintoma vasomotor; método de tratamento de doença de alzheimer, de um distúrbio de deficiência da atenção, de esquizofrenia, de doença de parkinson, de discinésia tardia, de ataxia, de bradicinésia, de discinésias paroxìsmicas, de sìndrome da perna irrequieta, de tremor, de tremor essencial, de epilepsia, de apoplexia ou de trauma na cabeça; método de tratamento de doença arterial coronariana, de enfarte do miocárdio, de ataque isquêmico transitório, de angina, de fibrilação atrial, de agregação plaquetária, de risco de formação de coágulo sanguìneo, de sìndrome do intestino irritável, de constipação crÈnica, de doença do refluxo gastrintestinal, de dispepsia, de incontinência urinária por estresse ou de incontinência urinária de urgência; método de tratamento de depressão, de distúrbio compulsivo obsessivo, de tendência ao suicìdio, de distúrbio de ansiedade, de distúrbio bipolar, de distúrbio de pánico, de abstinência de nicotina, de abstinência de álcool, de abstinência de cocaìna, de abstinência de heroìna, de abstinência de anfetamina, de abstinência de drogas narcóticas, de insÈnia, de apnéia do sono, de narcolepsia, de distúrbio afetivo sanzonal, de sìndrome da perna irrequieta, de distúrbio de sono de turno de trabalho, de sìndrome da fase do sono retardada, de anorexia nervosa, de bulimia nervosa, de sìndrome do comer noturno, de superalimentação compulsiva, de sìndrome da fadiga crÈnica, de fibromialgia, de neuropatia de dor, de dor antinociceptiva, de sìndrome da dor crÈnica, de neuropatia diabética, de fogacho ou de suor noturno; e uso de um composto |
| CL2007001873A1 (es) * | 2006-06-27 | 2008-01-04 | Takeda Pharmaceutical | Acido((3s))-6-((¨2,6-dimetil-4-(3-(metilsulfonil)-propoxi)bifenil-3-il)metoxi-2,3-dihidro-1-benzofuran-3-il)acetico o una sal del mismo |
| JP5498168B2 (ja) | 2006-12-01 | 2014-05-21 | ブリストル−マイヤーズ スクイブ カンパニー | アテローム性動脈硬化および循環器疾患の治療のためのcetp阻害剤としてのn−((3−ベンジル)−2,2−(ビス−フェニル)−プロパン−1−アミン誘導体 |
| WO2008116107A2 (en) * | 2007-03-21 | 2008-09-25 | Takeda San Diego, Inc. | Piperazine derivatives as glucokinase activators |
| SG176464A1 (en) | 2008-05-09 | 2011-12-29 | Agency Science Tech & Res | Diagnosis and treatment of kawasaki disease |
| EP2509596B1 (en) | 2009-12-08 | 2019-08-28 | Case Western Reserve University | Gamma aminoacids for treating ocular disorders |
| US8916563B2 (en) | 2010-07-16 | 2014-12-23 | The Trustees Of Columbia University In The City Of New York | Aldose reductase inhibitors and uses thereof |
| CA2848877A1 (en) * | 2011-09-15 | 2013-03-21 | Taipei Medical University | Use of indolyl and indolinvl hvdroxamates for treating heart failure or neuronal injury |
| US9339542B2 (en) * | 2013-04-16 | 2016-05-17 | John L Couvaras | Hypertension reducing composition |
| SG11201507496UA (en) | 2013-04-17 | 2015-11-27 | Pfizer | N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases |
| CN103739547B (zh) * | 2014-01-03 | 2015-09-02 | 沈阳药科大学 | 2-[6-甲氧基-3-(2,3-二氯苯基)甲基-4-氧代-1,4-二氢-1(4h)-喹啉基]乙酸的合成方法 |
| WO2016055901A1 (en) | 2014-10-08 | 2016-04-14 | Pfizer Inc. | Substituted amide compounds |
| JP2018511616A (ja) * | 2015-04-14 | 2018-04-26 | ケース ウエスタン リザーブ ユニバーシティ | 短鎖デヒドロゲナーゼ活性を調節する組成物および方法 |
| WO2017168174A1 (en) | 2016-04-02 | 2017-10-05 | N4 Pharma Uk Limited | New pharmaceutical forms of sildenafil |
| IL283809B2 (en) | 2016-06-21 | 2024-01-01 | Univ Columbia | Compounds for use in a method of treating neuropathy, retinopathy, nephropathy, or cardiomyopathy |
| WO2018002673A1 (en) | 2016-07-01 | 2018-01-04 | N4 Pharma Uk Limited | Novel formulations of angiotensin ii receptor antagonists |
| US10344002B2 (en) | 2016-09-26 | 2019-07-09 | Nusirt Sciences, Inc. | Compositions and methods for treating metabolic disorders |
| EP3548035A4 (en) | 2016-11-30 | 2020-07-22 | Case Western Reserve University | COMBINATIONS OF 15-PGDH INHIBITORS WITH CORCOSTEROIDS AND / OR TNF INHIBITORS AND THEIR USES |
| AU2018215678A1 (en) | 2017-02-06 | 2019-08-22 | Board Of Regents Of The University Of Texas System | Compositions and methods of modulating short-chain dehydrogenase activity |
| IL272246B2 (en) | 2017-07-28 | 2026-01-01 | Applied Therapeutics Inc | History of 2-(4-oxo/thioketone/azo-3-((substituted)benzo[d]thiazol-2-yl)methyl)- 3,4-dihydrothieno[3,4-d]pyridazin-1-yl)acetic acid for use as an aldose reductase inhibitor for the treatment of galactosemia or prevention of galactosemia-related complications |
| IL321451A (en) | 2018-11-21 | 2025-08-01 | Univ Case Western Reserve | Compositions and methods of modulating short-chain dehydrogenase activity |
| US11248001B2 (en) | 2019-01-18 | 2022-02-15 | Astrazeneca Ab | PCSK9 inhibitors and methods of use thereof |
| AU2020254610A1 (en) | 2019-04-01 | 2021-11-18 | Applied Therapeutics Inc. | Inhibitors of aldose reductase |
| CN113966396A (zh) | 2019-05-07 | 2022-01-21 | 迈阿密大学 | 遗传性神经病和相关障碍的治疗和检测 |
| US11274082B2 (en) | 2019-05-31 | 2022-03-15 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
| WO2020243423A1 (en) | 2019-05-31 | 2020-12-03 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
| MX2022010258A (es) | 2020-02-21 | 2023-01-24 | Univ Case Western Reserve | Composiciones y métodos para tratar la lesión renal. |
| WO2022120353A1 (en) * | 2020-12-02 | 2022-06-09 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
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| IE47592B1 (en) | 1977-12-29 | 1984-05-02 | Ici Ltd | Enzyme inhibitory phthalazin-4-ylacetic acid derivatives, pharmaceutical compositions thereof,and process for their manufacture |
| US4939140A (en) | 1985-11-07 | 1990-07-03 | Pfizer Inc. | Heterocyclic oxophthalazinyl acetic acids |
| US4996204A (en) | 1989-05-11 | 1991-02-26 | Pfizer Inc. | Pyrido[2,3-d]pyridazinones as aldose reductase inhibitors |
| FR2647676A1 (fr) | 1989-06-05 | 1990-12-07 | Union Pharma Scient Appl | Nouveaux derives de pyridazinone, leurs procedes de preparation, medicaments les contenant, utiles notamment comme inhibiteurs de l'aldose reductase |
| EP0516860A4 (en) * | 1990-11-30 | 1993-12-01 | Tsumura & Co. | Chromone derivative and aldose reductase inhibitor containing the same as active ingredient |
| CZ387092A3 (en) | 1991-03-28 | 1994-02-16 | Pfizer | Pyridazinoacetic acids, their derivatives, process of their preparation and use |
| US5834466A (en) | 1994-12-22 | 1998-11-10 | The Regents Of The University Of California | Method for protecting of heart by limiting metabolic and ionic abnormalities developed during ischemia, following ischemia or resulting from ischemia |
| TW438587B (en) | 1995-06-20 | 2001-06-07 | Takeda Chemical Industries Ltd | A pharmaceutical composition for prophylaxis and treatment of diabetes |
| TR200000764T2 (tr) * | 1997-09-24 | 2001-03-21 | Orion Corporation | Fosfolamban inhibitörleri olarak, 1-okza, aza ve tiyanaftalin-2-on'ların biseterleri. |
| FR2822827B1 (fr) * | 2001-03-28 | 2003-05-16 | Sanofi Synthelabo | Nouveaux derives de n-(arylsulfonyl) beta-aminoacides comportant un groupe aminomethyle substitue, leur procede de preparation et les compositions pharmaceutiques en contenant |
| ATE348100T1 (de) * | 2001-03-30 | 2007-01-15 | Pfizer Prod Inc | Zwischenprodukten für die herstellung von pyridazinon aldose reductase inhibitoren. |
| AU2002236131B2 (en) * | 2001-04-30 | 2005-04-14 | Pfizer Products Inc. | Combinations of aldose reductase inhibitors and cyclooxygenase-2 inhibitors |
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2002
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- 2002-01-31 HU HU0303644A patent/HUP0303644A3/hu unknown
- 2002-01-31 CA CA002442476A patent/CA2442476A1/en not_active Abandoned
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- 2002-01-31 DK DK02716247T patent/DK1373259T3/da active
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- 2002-01-31 NZ NZ528406A patent/NZ528406A/en unknown
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- 2002-01-31 EP EP02716247A patent/EP1373259B1/en not_active Expired - Lifetime
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- 2002-01-31 CN CNB028076001A patent/CN1215067C/zh not_active Expired - Fee Related
- 2002-01-31 SI SI200230071T patent/SI1373259T1/xx unknown
- 2002-01-31 JP JP2002577823A patent/JP2004528319A/ja active Pending
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- 2002-01-31 DK DK04023149T patent/DK1491540T3/da active
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- 2002-01-31 EP EP04023149A patent/EP1491540B1/en not_active Expired - Lifetime
- 2002-01-31 GE GE5314A patent/GEP20053675B/en unknown
- 2002-01-31 PT PT02716247T patent/PT1373259E/pt unknown
- 2002-01-31 EE EEP200300470A patent/EE200300470A/xx unknown
- 2002-01-31 AT AT04023150T patent/ATE352551T1/de not_active IP Right Cessation
- 2002-01-31 UA UA2003098846A patent/UA73236C2/uk unknown
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- 2002-01-31 DE DE60202452T patent/DE60202452C5/de not_active Expired - Fee Related
- 2002-01-31 OA OA1200300222A patent/OA12453A/en unknown
- 2002-01-31 WO PCT/IB2002/000320 patent/WO2002079198A1/en not_active Ceased
- 2002-01-31 DE DE60216823T patent/DE60216823T2/de not_active Expired - Fee Related
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