HRP20030752A2 - Pyridazinone aldose reductase inhibitors - Google Patents

Pyridazinone aldose reductase inhibitors

Info

Publication number: HRP20030752A2
Authority: HR; Croatia
Prior art keywords: sulfonyl; pyridazin; alkyl; chloro; methylbenzofuran
Prior art date: 2001-03-30

Application number

HR20030752A

Other languages

English (en)

Croatian (hr)

Inventor

Lakshman Mylari Banavara

Original Assignee

Pfizer Products Inc.

Priority date (The priority date 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 date listed.)

2001-03-30

Filing date

2003-09-17

Publication date

2005-06-30

2003-09-17 Application filed by Pfizer Products Inc. filed Critical Pfizer Products Inc.

2005-06-30 Publication of HRP20030752A2 publication Critical patent/HRP20030752A2/hr

Links

239000003288 aldose reductase inhibitor Substances 0.000 title description 13
229940090865 aldose reductase inhibitors used in diabetes Drugs 0.000 title description 8
AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 343
-1 cinolinyl Chemical group 0.000 claims description 252
229940002612 prodrug Drugs 0.000 claims description 102
239000000651 prodrug Substances 0.000 claims description 102
150000003839 salts Chemical class 0.000 claims description 86
238000000034 method Methods 0.000 claims description 83
125000001424 substituent group Chemical group 0.000 claims description 60
235000019000 fluorine Nutrition 0.000 claims description 59
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 55
125000001153 fluoro group Chemical group F* 0.000 claims description 41
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 40
239000000460 chlorine Substances 0.000 claims description 32
229910052801 chlorine Inorganic materials 0.000 claims description 32
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 32
241000124008 Mammalia Species 0.000 claims description 30
229910052736 halogen Inorganic materials 0.000 claims description 29
150000002367 halogens Chemical class 0.000 claims description 29
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 28
229910052794 bromium Inorganic materials 0.000 claims description 25
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 24
125000002883 imidazolyl group Chemical group 0.000 claims description 24
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
125000000842 isoxazolyl group Chemical group 0.000 claims description 23
125000002971 oxazolyl group Chemical group 0.000 claims description 23
125000003226 pyrazolyl group Chemical group 0.000 claims description 23
125000000335 thiazolyl group Chemical group 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 21
125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 21
208000028867 ischemia Diseases 0.000 claims description 21
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 20
229910052731 fluorine Inorganic materials 0.000 claims description 20
239000011737 fluorine Substances 0.000 claims description 20
125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 20
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 19
208000002249 Diabetes Complications Diseases 0.000 claims description 18
206010012655 Diabetic complications Diseases 0.000 claims description 18
125000004076 pyridyl group Chemical group 0.000 claims description 18
125000000168 pyrrolyl group Chemical group 0.000 claims description 18
125000001544 thienyl group Chemical group 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 17
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 17
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 17
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
125000002541 furyl group Chemical group 0.000 claims description 17
125000005956 isoquinolyl group Chemical group 0.000 claims description 17
125000001715 oxadiazolyl group Chemical group 0.000 claims description 17
125000002098 pyridazinyl group Chemical group 0.000 claims description 17
125000005493 quinolyl group Chemical group 0.000 claims description 17
125000003831 tetrazolyl group Chemical group 0.000 claims description 17
125000001113 thiadiazolyl group Chemical group 0.000 claims description 17
125000001425 triazolyl group Chemical group 0.000 claims description 17
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 15
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 15
125000004534 benzothien-2-yl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 15
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 description 14
125000005554 pyridyloxy group Chemical group 0.000 claims description 14
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 13
125000001624 naphthyl group Chemical group 0.000 claims description 13
239000000825 pharmaceutical preparation Substances 0.000 claims description 13
239000003085 diluting agent Substances 0.000 claims description 12
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 description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 9
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 9
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 description 9
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 description 9
210000005003 heart tissue Anatomy 0.000 claims description 9
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 description 8
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 description 8
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
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 description 7
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 7
125000004536 indazol-1-yl group Chemical group N1(N=CC2=CC=CC=C12)* 0.000 claims description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
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 description 6
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 description 6
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 description 6
RBZSSTPBYFHRSR-UHFFFAOYSA-N 3-(1-benzofuran-2-ylsulfonyl)-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)C=2OC3=CC=CC=C3C=2)=N1 RBZSSTPBYFHRSR-UHFFFAOYSA-N 0.000 claims description 5
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 description 5
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 description 5
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 description 5
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 description 5
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 description 5
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 description 5
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 description 5
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 description 5
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 description 5
PJMQRZZJOSLFBJ-UHFFFAOYSA-N 3-imidazo[1,2-a]pyridin-3-ylsulfonyl-1H-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)C=2N3C=CC=CC3=NC=2)=N1 PJMQRZZJOSLFBJ-UHFFFAOYSA-N 0.000 claims description 5
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 description 5
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
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 description 4
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 description 4
125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
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 description 3
UGTGRHZJGQIRBG-UHFFFAOYSA-N 3-imidazol-1-ylsulfonyl-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)N2C=NC=C2)=N1 UGTGRHZJGQIRBG-UHFFFAOYSA-N 0.000 claims description 3
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 description 3
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
125000001041 indolyl group Chemical group 0.000 claims description 3
125000001786 isothiazolyl group Chemical group 0.000 claims description 3
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 3
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 3
125000003373 pyrazinyl group Chemical group 0.000 claims description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
125000006085 pyrrolopyridyl group Chemical group 0.000 claims description 3
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
159000000000 sodium salts Chemical class 0.000 claims description 3
125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 claims description 3
CYXNLUKXQVTYHT-UHFFFAOYSA-N 3-[(5-chloro-3-methyl-1-benzofuran-2-yl)sulfanyl]-6-methoxypyridazine Chemical group N1=NC(OC)=CC=C1SC1=C(C)C2=CC(Cl)=CC=C2O1 CYXNLUKXQVTYHT-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
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 description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
239000011541 reaction mixture Substances 0.000 description 80
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 78
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150000003512 tertiary amines Chemical class 0.000 description 1
125000005888 tetrahydroindolyl group Chemical group 0.000 description 1
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230000002537 thrombolytic effect Effects 0.000 description 1
PBJUNZJWGZTSKL-MRXNPFEDSA-N tiagabine Chemical compound C1=CSC(C(=CCCN2C[C@@H](CCC2)C(O)=O)C2=C(C=CS2)C)=C1C PBJUNZJWGZTSKL-MRXNPFEDSA-N 0.000 description 1
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
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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

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HR20030752A 2001-03-30 2003-09-17 Pyridazinone aldose reductase inhibitors HRP20030752A2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US28005101P	2001-03-30	2001-03-30
PCT/IB2002/000320 WO2002079198A1 (en)	2001-03-30	2002-01-31	Pyridazinone aldose reductase inhibitors

Publications (1)

Publication Number	Publication Date
HRP20030752A2 true HRP20030752A2 (en)	2005-06-30

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ID=23071435

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Application Number	Title	Priority Date	Filing Date
HR20030752A HRP20030752A2 (en)	2001-03-30	2003-09-17	Pyridazinone aldose reductase inhibitors

Country Status (44)

Country	Link
US (2)	US6579879B2 (xx)
EP (3)	EP1491540B1 (xx)
JP (1)	JP2004528319A (xx)
KR (1)	KR100586138B1 (xx)
CN (1)	CN1215067C (xx)
AP (1)	AP2002002461A0 (xx)
AR (1)	AR035798A1 (xx)
AT (3)	ATE348100T1 (xx)
AU (1)	AU2002226634B2 (xx)
BG (1)	BG108179A (xx)
BR (1)	BR0208571A (xx)
CA (1)	CA2442476A1 (xx)
CZ (1)	CZ20032563A3 (xx)
DE (3)	DE60216823T2 (xx)
DK (2)	DK1491540T3 (xx)
EA (1)	EA006023B1 (xx)
EC (1)	ECSP034671A (xx)
EE (1)	EE200300470A (xx)
ES (2)	ES2274369T3 (xx)
GE (1)	GEP20053675B (xx)
HK (1)	HK1061678A1 (xx)
HR (1)	HRP20030752A2 (xx)
HU (1)	HUP0303644A3 (xx)
IL (1)	IL156462A0 (xx)
IS (3)	IS2205B (xx)
MA (1)	MA27003A1 (xx)
MX (1)	MXPA03008850A (xx)
MY (1)	MY134304A (xx)
NO (1)	NO20034345L (xx)
NZ (1)	NZ528406A (xx)
OA (1)	OA12453A (xx)
PA (1)	PA8541801A1 (xx)
PE (1)	PE20030007A1 (xx)
PL (1)	PL365294A1 (xx)
PT (2)	PT1491540E (xx)
SI (1)	SI1373259T1 (xx)
SK (1)	SK11852003A3 (xx)
TN (1)	TNSN02037A1 (xx)
TW (1)	TWI245762B (xx)
UA (1)	UA73236C2 (xx)
UY (1)	UY27237A1 (xx)
WO (1)	WO2002079198A1 (xx)
YU (1)	YU71403A (xx)
ZA (1)	ZA200304671B (xx)

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RU2618628C1 (ru)	2013-04-17	2017-05-05	Пфайзер Инк.	Производные N-пиперидин-3-илбензамида для лечения сердечно-сосудистых заболеваний
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- 2002-01-31 JP JP2002577823A patent/JP2004528319A/ja active Pending
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Also Published As

Publication number	Publication date
CA2442476A1 (en)	2002-10-10
DK1373259T3 (da)	2005-03-29
DE60217930T2 (de)	2007-10-18
DE60216823T2 (de)	2007-10-04
WO2002079198A1 (en)	2002-10-10
US6579879B2 (en)	2003-06-17
ES2231681T3 (es)	2005-05-16
CN1500087A (zh)	2004-05-26
EA006023B1 (ru)	2005-08-25
IS6845A (is)	2003-06-16
AP2002002461A0 (en)	2002-06-30
ATE348100T1 (de)	2007-01-15
SK11852003A3 (sk)	2004-07-07
YU71403A (sh)	2006-05-25
TNSN02037A1 (fr)	2005-12-23
EA200300673A1 (ru)	2003-12-25
UA73236C2 (en)	2005-06-15
OA12453A (en)	2006-05-24
EP1373259B1 (en)	2004-12-29
IS8251A (is)	2006-01-23
NO20034345D0 (no)	2003-09-29
EP1491541A1 (en)	2004-12-29
ATE286049T1 (de)	2005-01-15
TWI245762B (en)	2005-12-21
IL156462A0 (en)	2004-01-04
EP1491541B1 (en)	2007-01-24
DE60202452C5 (de)	2006-11-23
UY27237A1 (es)	2002-12-31
IS8250A (is)	2006-01-23
PE20030007A1 (es)	2003-01-28
US20030162784A1 (en)	2003-08-28
EP1491540A1 (en)	2004-12-29
AU2002226634B2 (en)	2007-01-25
PT1373259E (pt)	2005-03-31
MY134304A (en)	2007-12-31
DE60202452T2 (de)	2006-02-09
AR035798A1 (es)	2004-07-14
ECSP034671A (es)	2003-08-29
KR100586138B1 (ko)	2006-06-07
PT1491540E (pt)	2007-01-31
BG108179A (en)	2004-09-30
HK1061678A1 (en)	2004-09-30
GEP20053675B (en)	2005-11-25
EE200300470A (et)	2004-02-16
BR0208571A (pt)	2004-03-23
DK1491540T3 (da)	2007-03-26
ES2274369T3 (es)	2007-05-16
US6849629B2 (en)	2005-02-01
EP1491540B1 (en)	2006-12-13
JP2004528319A (ja)	2004-09-16
ZA200304671B (en)	2004-06-25
MA27003A1 (fr)	2004-12-20
DE60217930D1 (de)	2007-03-15
HUP0303644A2 (hu)	2004-03-01
MXPA03008850A (es)	2003-12-04
ATE352551T1 (de)	2007-02-15
PL365294A1 (en)	2004-12-27
KR20030088484A (ko)	2003-11-19
SI1373259T1 (en)	2005-04-30
DE60202452D1 (de)	2005-02-03
NO20034345L (no)	2003-09-29
CZ20032563A3 (cs)	2004-05-12
DE60216823D1 (de)	2007-01-25
PA8541801A1 (es)	2002-10-28
HUP0303644A3 (en)	2008-06-30
EP1373259A1 (en)	2004-01-02
IS2205B (is)	2007-02-15
NZ528406A (en)	2004-03-26
US20020143017A1 (en)	2002-10-03
CN1215067C (zh)	2005-08-17

Publication	Publication Date	Title
HRP20030752A2 (en)	2005-06-30	Pyridazinone aldose reductase inhibitors
AU2002226634A1 (en)	2003-04-03	Pyridazinone aldose reductase inhibitors
TWI855068B (zh)	2024-09-11	THR-β調節劑及其使用方法
US6570013B2 (en)	2003-05-27	Salts of zopolrestat
HRP20010716A2 (en)	2002-12-31	Aminopyrimidines as sorbitol dehydrogenase inhibitors
KR20080087841A (ko)	2008-10-01	무스카린 수용체의 조절제
EP2062898A2 (de)	2009-05-27	Spirocyclische Cyclohexan-Derivate
TWI258478B (en)	2006-07-21	Tetrazole derivatives and methods of treatment of metabolic-related disorders thereof
JP2001522374A (ja)	2001-11-13	ドパミンｄ３受容体モジュレーターとしての置換テトラヒドロイソキノリン類
US7572910B2 (en)	2009-08-11	Pyridazinone aldose reductase inhibitors
US20040198740A1 (en)	2004-10-07	Therapies relating to combinations of aldose reductase inhibitors and cyclooxygenase-2
AU2002236131A1 (en)	2003-04-17	Combinations of aldose reductase inhibitors and cyclooxygenase-2 inhibitors
WO2002098429A1 (en)	2002-12-12	Ethanolamine, diethanolamine or triethanolamine salt of zopolrestat

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Date	Code	Title
2005-06-30	A1OB	Publication of a patent application
2005-06-30	ARAI	Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application
2007-09-24	ODBC	Application rejected