AU2007280984A1 - Quinoline derivatives - Google Patents
Quinoline derivatives Download PDFInfo
- Publication number
- AU2007280984A1 AU2007280984A1 AU2007280984A AU2007280984A AU2007280984A1 AU 2007280984 A1 AU2007280984 A1 AU 2007280984A1 AU 2007280984 A AU2007280984 A AU 2007280984A AU 2007280984 A AU2007280984 A AU 2007280984A AU 2007280984 A1 AU2007280984 A1 AU 2007280984A1
- Authority
- AU
- Australia
- Prior art keywords
- methyl
- hydroxyquinolin
- chloro
- acetamide
- pyridin
- 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.)
- Abandoned
Links
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 10
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title description 2
- -1 amino(3,4-dimethoxyphenyl)methyl Chemical group 0.000 claims description 337
- 150000001875 compounds Chemical class 0.000 claims description 202
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 191
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 146
- 102100029272 5-demethoxyubiquinone hydroxylase, mitochondrial Human genes 0.000 claims description 107
- 101000770593 Homo sapiens 5-demethoxyubiquinone hydroxylase, mitochondrial Proteins 0.000 claims description 101
- 101000738400 Homo sapiens Cyclin-dependent kinase 11B Proteins 0.000 claims description 100
- 230000000694 effects Effects 0.000 claims description 83
- 238000000034 method Methods 0.000 claims description 73
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 58
- 208000035475 disorder Diseases 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 39
- 239000000651 prodrug Substances 0.000 claims description 39
- 229940002612 prodrug Drugs 0.000 claims description 39
- 241001465754 Metazoa Species 0.000 claims description 35
- 150000003857 carboxamides Chemical class 0.000 claims description 31
- 230000005764 inhibitory process Effects 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 31
- 238000011282 treatment Methods 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 208000028867 ischemia Diseases 0.000 claims description 20
- 210000004556 brain Anatomy 0.000 claims description 17
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 claims description 17
- NTVCMEJZWNSEFW-ICSRJNTNSA-N 4-(diaminomethylideneamino)-n-[[(2s)-1-[(2s)-3-hydroxy-2-(naphthalen-2-ylsulfonylamino)propanoyl]pyrrolidin-2-yl]methyl]butanamide Chemical compound NC(N)=NCCCC(=O)NC[C@@H]1CCCN1C(=O)[C@H](CO)NS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 NTVCMEJZWNSEFW-ICSRJNTNSA-N 0.000 claims description 16
- 206010063837 Reperfusion injury Diseases 0.000 claims description 16
- 230000009286 beneficial effect Effects 0.000 claims description 16
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 208000024891 symptom Diseases 0.000 claims description 16
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- YJRRXUGZZNAGQS-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(3,4-dimethoxyphenyl)methyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1C(NC(C)=O)C1=CC(Cl)=C(C=CC=N2)C2=C1O YJRRXUGZZNAGQS-UHFFFAOYSA-N 0.000 claims description 15
- 206010061218 Inflammation Diseases 0.000 claims description 14
- 230000004054 inflammatory process Effects 0.000 claims description 14
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 12
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 12
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 11
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- 230000002401 inhibitory effect Effects 0.000 claims description 11
- 238000011321 prophylaxis Methods 0.000 claims description 11
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 11
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 10
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 10
- 229910000397 disodium phosphate Inorganic materials 0.000 claims description 9
- 235000019800 disodium phosphate Nutrition 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 208000017169 kidney disease Diseases 0.000 claims description 9
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 239000001488 sodium phosphate Substances 0.000 claims description 9
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 8
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 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 8
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
- 229910019142 PO4 Inorganic materials 0.000 claims description 7
- 210000004072 lung Anatomy 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 7
- 239000010452 phosphate Substances 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229940095102 methyl benzoate Drugs 0.000 claims description 6
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- QCDFBFJGMNKBDO-UHFFFAOYSA-N Clioquinol Chemical compound C1=CN=C2C(O)=C(I)C=C(Cl)C2=C1 QCDFBFJGMNKBDO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- RHJVIGLEIFVHIJ-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1[CH]CCCC1 RHJVIGLEIFVHIJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims description 5
- 125000003944 tolyl group Chemical group 0.000 claims description 5
- LYSTVVWUURZPGM-UHFFFAOYSA-N 5-chloro-7-(2-hydroxyphenyl)quinolin-8-ol Chemical compound Oc1ccccc1-c1cc(Cl)c2cccnc2c1O LYSTVVWUURZPGM-UHFFFAOYSA-N 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- 201000006474 Brain Ischemia Diseases 0.000 claims description 4
- 206010012289 Dementia Diseases 0.000 claims description 4
- DQTIFNBWFWGMEC-UHFFFAOYSA-N N-[(5-chloro-8-hydroxy-7-quinolinyl)-(2-furanyl)methyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C1=CC=CO1 DQTIFNBWFWGMEC-UHFFFAOYSA-N 0.000 claims description 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 4
- 206010035664 Pneumonia Diseases 0.000 claims description 4
- AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004188 dichlorophenyl group Chemical group 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 210000002216 heart Anatomy 0.000 claims description 4
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 208000023504 respiratory system disease Diseases 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- UJCCVEACHCYGFL-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-n-(8-hydroxyquinolin-2-yl)acetamide Chemical compound OC1=CC=CC(CC(=O)NC=2N=C3C(O)=CC=CC3=CC=2)=C1 UJCCVEACHCYGFL-UHFFFAOYSA-N 0.000 claims description 3
- JXWPLJIQVHADDA-UHFFFAOYSA-N 5-chloro-7-[4-(dimethylamino)phenyl]quinolin-8-ol Chemical compound C1=CC(N(C)C)=CC=C1C1=CC(Cl)=C(C=CC=N2)C2=C1O JXWPLJIQVHADDA-UHFFFAOYSA-N 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 208000002249 Diabetes Complications Diseases 0.000 claims description 3
- 208000019693 Lung disease Diseases 0.000 claims description 3
- 208000023178 Musculoskeletal disease Diseases 0.000 claims description 3
- 208000018262 Peripheral vascular disease Diseases 0.000 claims description 3
- 208000029162 bladder disease Diseases 0.000 claims description 3
- 201000006370 kidney failure Diseases 0.000 claims description 3
- 208000030159 metabolic disease Diseases 0.000 claims description 3
- HUMISYOZPNFBSJ-UHFFFAOYSA-N n-(8-hydroxyquinolin-2-yl)-2-thiophen-2-ylacetamide Chemical compound N1=C2C(O)=CC=CC2=CC=C1NC(=O)CC1=CC=CS1 HUMISYOZPNFBSJ-UHFFFAOYSA-N 0.000 claims description 3
- CIYVYRXBHSDPLD-UHFFFAOYSA-N n-[(8-hydroxyquinolin-7-yl)methyl]acetamide Chemical compound C1=CC=NC2=C(O)C(CNC(=O)C)=CC=C21 CIYVYRXBHSDPLD-UHFFFAOYSA-N 0.000 claims description 3
- VXTBFUPMJZNGSF-UHFFFAOYSA-N n-[1-(5-chloro-8-hydroxyquinolin-7-yl)ethyl]acetamide Chemical compound C1=CC=NC2=C(O)C(C(NC(C)=O)C)=CC(Cl)=C21 VXTBFUPMJZNGSF-UHFFFAOYSA-N 0.000 claims description 3
- 210000000056 organ Anatomy 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- VLLOOFRJJIMSLV-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-n-(8-hydroxyquinolin-2-yl)acetamide Chemical compound C1=CC(O)=CC=C1CC(=O)NC1=CC=C(C=CC=C2O)C2=N1 VLLOOFRJJIMSLV-UHFFFAOYSA-N 0.000 claims description 2
- BEIIUPXOBWYBOB-UHFFFAOYSA-N 4-[acetamido-(5-chloro-8-hydroxyquinolin-7-yl)methyl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C(NC(C)=O)C1=CC(Cl)=C(C=CC=N2)C2=C1O BEIIUPXOBWYBOB-UHFFFAOYSA-N 0.000 claims description 2
- 208000036982 Spinal cord ischaemia Diseases 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 210000004165 myocardium Anatomy 0.000 claims description 2
- RYNCRISZMOBICO-UHFFFAOYSA-N n-[(2,4-dichlorophenyl)-(8-hydroxyquinolin-7-yl)methyl]-3-methylbutanamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(NC(=O)CC(C)C)C1=CC=C(Cl)C=C1Cl RYNCRISZMOBICO-UHFFFAOYSA-N 0.000 claims description 2
- IQDLCSKSBHSKHI-UHFFFAOYSA-N n-[(2,4-dichlorophenyl)-(8-hydroxyquinolin-7-yl)methyl]acetamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C1=CC=C(Cl)C=C1Cl IQDLCSKSBHSKHI-UHFFFAOYSA-N 0.000 claims description 2
- VUZPLTKIMHSUFJ-UHFFFAOYSA-N n-[(2,4-dichlorophenyl)-(8-hydroxyquinolin-7-yl)methyl]butanamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(NC(=O)CCC)C1=CC=C(Cl)C=C1Cl VUZPLTKIMHSUFJ-UHFFFAOYSA-N 0.000 claims description 2
- RBZNNYFJAHVKOM-UHFFFAOYSA-N n-[(2,4-dichlorophenyl)-(8-hydroxyquinolin-7-yl)methyl]pentanamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(NC(=O)CCCC)C1=CC=C(Cl)C=C1Cl RBZNNYFJAHVKOM-UHFFFAOYSA-N 0.000 claims description 2
- JMTVJWPQYBJTGF-UHFFFAOYSA-N n-[(2,4-dichlorophenyl)-(8-hydroxyquinolin-7-yl)methyl]propanamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(NC(=O)CC)C1=CC=C(Cl)C=C1Cl JMTVJWPQYBJTGF-UHFFFAOYSA-N 0.000 claims description 2
- FQHJZWPFSOOPSC-UHFFFAOYSA-N n-[(2-butyl-1h-imidazol-5-yl)-(5-chloro-8-hydroxyquinolin-7-yl)methyl]acetamide Chemical compound N1C(CCCC)=NC=C1C(NC(C)=O)C1=CC(Cl)=C(C=CC=N2)C2=C1O FQHJZWPFSOOPSC-UHFFFAOYSA-N 0.000 claims description 2
- DFVYGAJFBQCMQR-UHFFFAOYSA-N n-[(2-chlorophenyl)-(8-hydroxyquinolin-7-yl)methyl]-3-phenylpropanamide Chemical compound C1=CC2=CC=CN=C2C(O)=C1C(C=1C(=CC=CC=1)Cl)NC(=O)CCC1=CC=CC=C1 DFVYGAJFBQCMQR-UHFFFAOYSA-N 0.000 claims description 2
- PHCZZCIRGOHMGT-UHFFFAOYSA-N n-[(3,4-dimethoxyphenyl)-(8-hydroxyquinolin-7-yl)methyl]-3-methylbutanamide Chemical compound C1=C(OC)C(OC)=CC=C1C(NC(=O)CC(C)C)C1=CC=C(C=CC=N2)C2=C1O PHCZZCIRGOHMGT-UHFFFAOYSA-N 0.000 claims description 2
- ZAAFQAWOULZVHU-UHFFFAOYSA-N n-[(3,4-dimethoxyphenyl)-(8-hydroxyquinolin-7-yl)methyl]-3-phenylpropanamide Chemical compound C1=C(OC)C(OC)=CC=C1C(C=1C(=C2N=CC=CC2=CC=1)O)NC(=O)CCC1=CC=CC=C1 ZAAFQAWOULZVHU-UHFFFAOYSA-N 0.000 claims description 2
- DABPCQYLGSZBAM-UHFFFAOYSA-N n-[(3,4-dimethoxyphenyl)-(8-hydroxyquinolin-7-yl)methyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1C(NC(C)=O)C1=CC=C(C=CC=N2)C2=C1O DABPCQYLGSZBAM-UHFFFAOYSA-N 0.000 claims description 2
- FEMAOGCTYDYUOH-UHFFFAOYSA-N n-[(4-chlorophenyl)-(8-hydroxyquinolin-7-yl)methyl]cyclohexanecarboxamide Chemical compound C1=CC2=CC=CN=C2C(O)=C1C(C=1C=CC(Cl)=CC=1)NC(=O)C1CCCCC1 FEMAOGCTYDYUOH-UHFFFAOYSA-N 0.000 claims description 2
- MPANGTHZKAYICZ-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(1h-indol-7-yl)methyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C1=CC=CC2=C1NC=C2 MPANGTHZKAYICZ-UHFFFAOYSA-N 0.000 claims description 2
- JJXIGWGOBRKULC-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(3,4-dimethoxyphenyl)methyl]-2,2-diphenylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1C(C=1C(=C2N=CC=CC2=C(Cl)C=1)O)NC(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 JJXIGWGOBRKULC-UHFFFAOYSA-N 0.000 claims description 2
- CTYUAEZIHUBFNB-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(3,4-dimethoxyphenyl)methyl]-n-methylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1C(N(C)C(C)=O)C1=CC(Cl)=C(C=CC=N2)C2=C1O CTYUAEZIHUBFNB-UHFFFAOYSA-N 0.000 claims description 2
- RNVDOTVHDOVUGT-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(3,4-dimethoxyphenyl)methyl]benzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(C=1C(=C2N=CC=CC2=C(Cl)C=1)O)NC(=O)C1=CC=CC=C1 RNVDOTVHDOVUGT-UHFFFAOYSA-N 0.000 claims description 2
- BGOQCSKPNQNTCQ-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(4-hydroxyphenyl)methyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C1=CC=C(O)C=C1 BGOQCSKPNQNTCQ-UHFFFAOYSA-N 0.000 claims description 2
- AOGPGSDKLYPWGC-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(4-pyrazol-1-ylphenyl)methyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C(C=C1)=CC=C1N1C=CC=N1 AOGPGSDKLYPWGC-UHFFFAOYSA-N 0.000 claims description 2
- SURVYJGJBZNGRQ-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-[4-(morpholine-4-carbonyl)phenyl]methyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C(C=C1)=CC=C1C(=O)N1CCOCC1 SURVYJGJBZNGRQ-UHFFFAOYSA-N 0.000 claims description 2
- PFAGOWWNQYNZCI-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-pyridin-3-ylmethyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C1=CC=CN=C1 PFAGOWWNQYNZCI-UHFFFAOYSA-N 0.000 claims description 2
- NLXDRYMLVUXGAC-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-quinolin-3-ylmethyl]acetamide Chemical compound C1=CC=NC2=C(O)C(C(C=3C=C4C=CC=CC4=NC=3)NC(=O)C)=CC(Cl)=C21 NLXDRYMLVUXGAC-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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US83293706P | 2006-07-25 | 2006-07-25 | |
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PCT/CA2007/001324 WO2008014602A1 (fr) | 2006-07-25 | 2007-07-25 | Dérivés de quinoline |
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CA (1) | CA2658793A1 (fr) |
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EP1888548B1 (fr) | 2005-05-26 | 2012-08-22 | Neuron Systems, Inc | Dérivé de quinoline pour le traitement de maladies rétiniennes |
WO2009151972A1 (fr) * | 2008-05-28 | 2009-12-17 | , The United States Of America, As Represented By The Secretary Of The Army, On Behalf Of U.S. Army Medical Research And Materiel Command | Inhibiteurs à petites molécules de neurotoxines botuliniques |
US9000009B2 (en) * | 2008-12-10 | 2015-04-07 | The Trustees Of The University Of Pennsylvania | Small molecule activators of mitochondrial function |
US9150600B2 (en) | 2009-05-07 | 2015-10-06 | Regents Of The University Of Minnesota | Triptolide prodrugs |
DK2427467T3 (en) | 2009-05-07 | 2015-11-09 | Univ Minnesota | Triptolid prodrugs |
WO2011041655A1 (fr) | 2009-10-01 | 2011-04-07 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Dérivés de la quinazolin-4-amine; et méthodes d'utilisation |
US9814701B2 (en) | 2009-12-11 | 2017-11-14 | Aldeyra Therapeutics, Inc. | Compositions and methods for the treatment of macular degeneration |
EP2345642A1 (fr) * | 2009-12-29 | 2011-07-20 | Polichem S.A. | Dérivés de 8-hydroxyquinoline-7-carboxamide secondaire pour une utilisation en tant qu'agents antifongiques |
EP2345641A1 (fr) * | 2009-12-29 | 2011-07-20 | Polichem S.A. | Nouveaux dérivés de 8-hydroxyquinoline-7-carboxamide secondaire |
US8658170B2 (en) | 2010-01-06 | 2014-02-25 | Joseph P. Errico | Combination therapy with MDM2 and EFGR inhibitors |
EP2521553A4 (fr) * | 2010-01-06 | 2013-08-28 | Errico Joseph P | Méthodes et compositions pour le développement de médicaments ciblés |
CN102858763B (zh) * | 2010-02-23 | 2015-01-21 | 康奈尔大学 | 脯氨酰羟化酶抑制剂及其使用方法 |
HUP1000243A2 (en) * | 2010-05-06 | 2012-01-30 | Avidin Kft | 8-hidroxy-quinoline derivatives |
CA2799792A1 (fr) * | 2010-05-18 | 2011-11-24 | The United States Of America, As Represented By The Secretary, Departmen T Of Health And Human Services | Inhibiteurs de la 12-lipoxygenase humaine |
MX2013015058A (es) | 2011-06-24 | 2014-01-20 | Amgen Inc | Antagonistas de melastatina 8 de potencial receptor transitorio y su uso en tratamientos. |
CA2839699A1 (fr) | 2011-06-24 | 2012-12-27 | Amgen Inc. | Antagonistes de trpm8 et leur utilisation dans des traitements |
US8952009B2 (en) | 2012-08-06 | 2015-02-10 | Amgen Inc. | Chroman derivatives as TRPM8 inhibitors |
RU2015120478A (ru) * | 2012-12-20 | 2017-01-25 | Альдейра Терапьютикс, Инк. | Пери-карбинолы |
US9687481B2 (en) | 2013-01-23 | 2017-06-27 | Aldeyra Therapeutics, Inc. | Toxic aldehyde related diseases and treatment |
AU2014209585A1 (en) | 2013-01-25 | 2015-07-23 | Aldeyra Therapeutics, Inc. | Novel traps in the treatment of macular degeneration |
KR101802048B1 (ko) * | 2013-04-02 | 2017-12-28 | 안지 파마슈티컬 코퍼레이션 리미티드 | 항신경퇴행성제로서의 다작용성 퀴놀린 유도체 |
US10716783B2 (en) | 2013-12-12 | 2020-07-21 | Cornell University | Prolylhydroxylase/ATF4 inhibitors and methods of use for treating neural cell injury or death and conditions resulting therefrom |
HUP1500098A2 (hu) * | 2015-03-09 | 2016-09-28 | Avidin Kft | 8-hidroxikinolin származékok új enantiomerjei és szintézisük |
KR102439852B1 (ko) * | 2015-04-17 | 2022-09-05 | 가천대학교 산학협력단 | 2-아미노퀴놀린-8-올 유도체, 및 이의 용도 |
AU2016311158A1 (en) | 2015-08-21 | 2018-04-05 | Aldeyra Therapeutics, Inc. | Deuterated compounds and uses thereof |
WO2017175842A1 (fr) * | 2016-04-07 | 2017-10-12 | 国立大学法人京都大学 | Composé et composition pharmaceutique concernant la modification de l'épissage |
MX2018013472A (es) | 2016-05-09 | 2019-02-28 | Aldeyra Therapeutics Inc | Tratamiento de combinacion de trastornos y enfermedades inflamatorios oculares. |
WO2018043674A1 (fr) * | 2016-08-31 | 2018-03-08 | 国立大学法人京都大学 | Composition pour activer la neurogenèse |
WO2018108627A1 (fr) | 2016-12-12 | 2018-06-21 | Bayer Cropscience Aktiengesellschaft | Utilisation d'indolinylméthylsulfonamides substitués ou de leurs sels pour accroître la tolérance au stress chez les plantes |
EP3596040B1 (fr) | 2017-03-16 | 2023-10-11 | Aldeyra Therapeutics, Inc. | Composés polymorphes de sels de 6-chloro-3-amino-2(2-hydroxypropyl)quinoline et leurs utilisations |
EP3388419A1 (fr) | 2017-04-12 | 2018-10-17 | Leadiant Biosciences SA | Inhibiteurs de gli1 et utilisations associées |
AU2018348174A1 (en) | 2017-10-10 | 2020-04-23 | Aldeyra Therapeutics, Inc. | Treatment of inflammatory disorders |
CN111920811B (zh) * | 2018-06-13 | 2021-09-21 | 四川轻化工大学 | 一种治疗抗痛风、抗高尿酸血症的药物组合物ⅲ |
CN112714762A (zh) | 2018-08-06 | 2021-04-27 | 奥尔德拉医疗公司 | 多晶型化合物及其用途 |
AU2019359823A1 (en) * | 2018-10-17 | 2021-05-20 | Duke University | Quinone reductase 2 inhibitors for use as neuroprotective agents |
EP3962894A4 (fr) | 2019-05-02 | 2023-01-11 | Aldeyra Therapeutics, Inc. | Composés polymorphes et leurs utilisations |
CN114650988A (zh) * | 2019-11-01 | 2022-06-21 | 詹森生物科技公司 | 作为二氢乳清酸脱氢酶(dhodh)抑制剂用于治疗癌症、自身免疫性和炎性疾病的氟化喹啉和喹喔啉衍生物 |
US20230108479A1 (en) * | 2020-03-04 | 2023-04-06 | University Of Kentucky Research Foundation | Substituted N-Benzhydrylacetamide Inhibitors of Jamanji Domain Histone Demethylases for the Treatment of Cancer |
WO2021231792A1 (fr) | 2020-05-13 | 2021-11-18 | Aldeyra Therapeutics, Inc. | Formulations pharmaceutiques et leurs utilisations |
CN111689944B (zh) * | 2020-06-10 | 2021-11-16 | 中山大学 | 喹啉色胺杂联体及其在制备治疗阿尔茨海默病的药物中的应用 |
CN111595990A (zh) * | 2020-07-27 | 2020-08-28 | 天津泰普制药有限公司 | 一种8-羟基喹诺酮有关物质的检测方法及应用 |
US20240124419A1 (en) * | 2021-02-02 | 2024-04-18 | The Regents Of The University Of Michigan | Small molecule inhibitors of grp78 and uses thereof |
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JP2002505660A (ja) * | 1996-09-10 | 2002-02-19 | ファルマシア・アンド・アップジョン・カンパニー | 抗ウィルス剤としての8―ヒドロキシ―7―置換キノリン |
EA200300449A1 (ru) * | 2000-10-12 | 2003-10-30 | Мерк Энд Ко., Инк. | Аза- и полиаза-нафталинилкарбоксамиды, полезные в качестве ингибиторов вич-интегразы |
EP2033952B1 (fr) * | 2001-03-01 | 2012-08-29 | Shionogi&Co., Ltd. | Composés d'hétéroaryle contenant de l'azote exerçant un effet inhibiteur sur l'intégrase du VIH |
AU2002950217A0 (en) * | 2002-07-16 | 2002-09-12 | Prana Biotechnology Limited | 8- Hydroxy Quinoline Derivatives |
-
2007
- 2007-07-25 CA CA002658793A patent/CA2658793A1/fr not_active Abandoned
- 2007-07-25 WO PCT/CA2007/001324 patent/WO2008014602A1/fr active Application Filing
- 2007-07-25 AU AU2007280984A patent/AU2007280984A1/en not_active Abandoned
- 2007-07-25 RU RU2009106461/04A patent/RU2009106461A/ru not_active Application Discontinuation
- 2007-07-25 JP JP2009521076A patent/JP2009544631A/ja active Pending
- 2007-07-25 CN CNA2007800346135A patent/CN101611009A/zh active Pending
- 2007-07-25 EP EP07815779A patent/EP2079699A1/fr not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
RU2009106461A (ru) | 2010-08-27 |
CA2658793A1 (fr) | 2008-02-07 |
WO2008014602A1 (fr) | 2008-02-07 |
EP2079699A1 (fr) | 2009-07-22 |
JP2009544631A (ja) | 2009-12-17 |
CN101611009A (zh) | 2009-12-23 |
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