RU2009106461A - Хинолиновые производные - Google Patents
Хинолиновые производные Download PDFInfo
- Publication number
- RU2009106461A RU2009106461A RU2009106461/04A RU2009106461A RU2009106461A RU 2009106461 A RU2009106461 A RU 2009106461A RU 2009106461/04 A RU2009106461/04 A RU 2009106461/04A RU 2009106461 A RU2009106461 A RU 2009106461A RU 2009106461 A RU2009106461 A RU 2009106461A
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- hydroxyquinolin
- chloro
- acetamide
- pyridin
- Prior art date
Links
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- -1 amino (3,4-dimethoxyphenyl) methyl Chemical group 0.000 claims abstract 140
- 150000001875 compounds Chemical class 0.000 claims abstract 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 30
- 239000000651 prodrug Substances 0.000 claims abstract 13
- 229940002612 prodrug Drugs 0.000 claims abstract 13
- 150000003839 salts Chemical class 0.000 claims abstract 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 9
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims abstract 8
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract 8
- 150000002367 halogens Chemical class 0.000 claims abstract 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 8
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 7
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract 6
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims abstract 5
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims abstract 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract 5
- 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 abstract 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract 5
- 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 abstract 5
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims abstract 5
- 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 abstract 5
- 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 abstract 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims abstract 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract 4
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims abstract 4
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims abstract 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims abstract 4
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims abstract 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 4
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims abstract 4
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims abstract 4
- 125000001424 substituent group Chemical group 0.000 claims abstract 4
- XHPVOSNOIWGRQQ-UHFFFAOYSA-N 4-pyridin-2-ylmorpholine Chemical compound C1COCCN1C1=CC=CC=N1 XHPVOSNOIWGRQQ-UHFFFAOYSA-N 0.000 claims abstract 2
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 claims 10
- 102100029272 5-demethoxyubiquinone hydroxylase, mitochondrial Human genes 0.000 claims 8
- 101000770593 Homo sapiens 5-demethoxyubiquinone hydroxylase, mitochondrial Proteins 0.000 claims 8
- 101000738400 Homo sapiens Cyclin-dependent kinase 11B Proteins 0.000 claims 8
- 241001465754 Metazoa Species 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 230000000694 effects Effects 0.000 claims 6
- LYSTVVWUURZPGM-UHFFFAOYSA-N 5-chloro-7-(2-hydroxyphenyl)quinolin-8-ol Chemical compound Oc1ccccc1-c1cc(Cl)c2cccnc2c1O LYSTVVWUURZPGM-UHFFFAOYSA-N 0.000 claims 5
- 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 5
- 229910000397 disodium phosphate Inorganic materials 0.000 claims 4
- 235000019800 disodium phosphate Nutrition 0.000 claims 4
- 239000003937 drug carrier Substances 0.000 claims 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 4
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims 4
- 239000001488 sodium phosphate Substances 0.000 claims 4
- 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 3
- QCDFBFJGMNKBDO-UHFFFAOYSA-N Clioquinol Chemical compound C1=CN=C2C(O)=C(I)C=C(Cl)C2=C1 QCDFBFJGMNKBDO-UHFFFAOYSA-N 0.000 claims 3
- 206010061218 Inflammation Diseases 0.000 claims 3
- 206010063837 Reperfusion injury Diseases 0.000 claims 3
- 230000004054 inflammatory process Effects 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 230000005764 inhibitory process Effects 0.000 claims 3
- 208000037906 ischaemic injury Diseases 0.000 claims 3
- 230000000302 ischemic effect Effects 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 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 3
- 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 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 210000003734 kidney Anatomy 0.000 claims 2
- 229940095102 methyl benzoate Drugs 0.000 claims 2
- VXOYNYANFXYNKY-UHFFFAOYSA-N n-[(8-hydroxyquinolin-7-yl)-(4-methylphenyl)methyl]cyclohexanecarboxamide Chemical compound C1=CC(C)=CC=C1C(C=1C(=C2N=CC=CC2=CC=1)O)NC(=O)C1CCCCC1 VXOYNYANFXYNKY-UHFFFAOYSA-N 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- 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 1
- 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 1
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- IDJVLLNMVKSMRX-UHFFFAOYSA-N 4-[acetamido-(5-chloro-8-hydroxyquinolin-7-yl)methyl]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1C(NC(C)=O)C1=CC(Cl)=C(C=CC=N2)C2=C1O IDJVLLNMVKSMRX-UHFFFAOYSA-N 0.000 claims 1
- ZDASUJMDVPTNTF-UHFFFAOYSA-N 5,7-dibromo-8-quinolinol Chemical compound C1=CN=C2C(O)=C(Br)C=C(Br)C2=C1 ZDASUJMDVPTNTF-UHFFFAOYSA-N 0.000 claims 1
- GPRMTKROYXLBIF-UHFFFAOYSA-N 5-chloro-7-(2-methoxypyridin-3-yl)quinolin-8-ol Chemical compound COC1=NC=CC=C1C1=CC(Cl)=C(C=CC=N2)C2=C1O GPRMTKROYXLBIF-UHFFFAOYSA-N 0.000 claims 1
- KPPTZFAWYRDLEQ-UHFFFAOYSA-N 5-chloro-7-(3-hydroxyphenyl)quinolin-8-ol Chemical compound OC1=CC=CC(C=2C(=C3N=CC=CC3=C(Cl)C=2)O)=C1 KPPTZFAWYRDLEQ-UHFFFAOYSA-N 0.000 claims 1
- RAQLEKDJOWLWFN-UHFFFAOYSA-N 5-chloro-7-(4-hydroxyphenyl)quinolin-8-ol Chemical compound Oc1ccc(cc1)-c1cc(Cl)c2cccnc2c1O RAQLEKDJOWLWFN-UHFFFAOYSA-N 0.000 claims 1
- CDBKJODRUSBBIW-UHFFFAOYSA-N 5-chloro-7-pyridin-4-ylquinolin-8-ol hydrochloride Chemical compound Cl.Oc1c(cc(Cl)c2cccnc12)-c1ccncc1 CDBKJODRUSBBIW-UHFFFAOYSA-N 0.000 claims 1
- QTLXRPAAYBNQOW-UHFFFAOYSA-N 7-[amino-(3,4-dimethoxyphenyl)methyl]-5-chloroquinolin-8-ol Chemical compound C1=C(OC)C(OC)=CC=C1C(N)C1=CC(Cl)=C(C=CC=N2)C2=C1O QTLXRPAAYBNQOW-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 208000002249 Diabetes Complications Diseases 0.000 claims 1
- 206010012655 Diabetic complications Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 208000023178 Musculoskeletal disease Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000018262 Peripheral vascular disease Diseases 0.000 claims 1
- 206010035664 Pneumonia Diseases 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- WDFKMLRRRCGAKS-UHFFFAOYSA-N chloroxine Chemical compound C1=CN=C2C(O)=C(Cl)C=C(Cl)C2=C1 WDFKMLRRRCGAKS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 210000002216 heart Anatomy 0.000 claims 1
- UXZFQZANDVDGMM-UHFFFAOYSA-N iodoquinol Chemical compound C1=CN=C2C(O)=C(I)C=C(I)C2=C1 UXZFQZANDVDGMM-UHFFFAOYSA-N 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 210000004165 myocardium Anatomy 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- MWTVNGJQJROBGN-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(1h-indol-3-yl)methyl]acetamide Chemical compound C1=CC=NC2=C(O)C(C(C=3C4=CC=CC=C4NC=3)NC(=O)C)=CC(Cl)=C21 MWTVNGJQJROBGN-UHFFFAOYSA-N 0.000 claims 1
- USRJEHHHBZYAMA-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(1h-indol-4-yl)methyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C1=CC=CC2=C1C=CN2 USRJEHHHBZYAMA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- DUICHCGSDFOJKH-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(2,4-dichlorophenyl)methyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C1=CC=C(Cl)C=C1Cl DUICHCGSDFOJKH-UHFFFAOYSA-N 0.000 claims 1
- MWOGDLJTXTYVOT-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(2-chlorophenyl)methyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C1=CC=CC=C1Cl MWOGDLJTXTYVOT-UHFFFAOYSA-N 0.000 claims 1
- AIHIZRKOSJIJRP-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(2-methoxyphenyl)methyl]-2-methylpropanamide Chemical compound COC1=CC=CC=C1C(NC(=O)C(C)C)C1=CC(Cl)=C(C=CC=N2)C2=C1O AIHIZRKOSJIJRP-UHFFFAOYSA-N 0.000 claims 1
- VBZSJOLGJVSKSW-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(2-methoxyphenyl)methyl]acetamide Chemical compound COC1=CC=CC=C1C(NC(C)=O)C1=CC(Cl)=C(C=CC=N2)C2=C1O VBZSJOLGJVSKSW-UHFFFAOYSA-N 0.000 claims 1
- AKOYFLRLPAVVCZ-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(2-methoxyphenyl)methyl]butanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)CCC)C1=CC=CC=C1OC AKOYFLRLPAVVCZ-UHFFFAOYSA-N 0.000 claims 1
- BUMPAWLVAKLTNJ-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(2-methoxyphenyl)methyl]pentanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)CCCC)C1=CC=CC=C1OC BUMPAWLVAKLTNJ-UHFFFAOYSA-N 0.000 claims 1
- HLJCTESVUQYBST-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(2-methoxyphenyl)methyl]propanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)CC)C1=CC=CC=C1OC HLJCTESVUQYBST-UHFFFAOYSA-N 0.000 claims 1
- OODTVVGQUNPKOB-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(2-methoxypyridin-3-yl)methyl]acetamide Chemical compound COC1=NC=CC=C1C(NC(C)=O)C1=CC(Cl)=C(C=CC=N2)C2=C1O OODTVVGQUNPKOB-UHFFFAOYSA-N 0.000 claims 1
- IBAUVLUKFOUIRF-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(2-morpholin-4-ylpyridin-3-yl)methyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C1=CC=CN=C1N1CCOCC1 IBAUVLUKFOUIRF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- MDXIDWIREKGPHO-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(3,4-dimethoxyphenyl)methyl]-2-methylpropanamide Chemical compound C1=C(OC)C(OC)=CC=C1C(NC(=O)C(C)C)C1=CC(Cl)=C(C=CC=N2)C2=C1O MDXIDWIREKGPHO-UHFFFAOYSA-N 0.000 claims 1
- GCLJYXCLTDTIIC-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(3,4-dimethoxyphenyl)methyl]-2-phenoxyacetamide Chemical compound C1=C(OC)C(OC)=CC=C1C(C=1C(=C2N=CC=CC2=C(Cl)C=1)O)NC(=O)COC1=CC=CC=C1 GCLJYXCLTDTIIC-UHFFFAOYSA-N 0.000 claims 1
- LCEIWBQLKCKCDA-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(3,4-dimethoxyphenyl)methyl]-2-phenylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1C(C=1C(=C2N=CC=CC2=C(Cl)C=1)O)NC(=O)CC1=CC=CC=C1 LCEIWBQLKCKCDA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- XJWSHMLACZWDDN-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(3,4-dimethoxyphenyl)methyl]butanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)CCC)C1=CC=C(OC)C(OC)=C1 XJWSHMLACZWDDN-UHFFFAOYSA-N 0.000 claims 1
- FYKDHTLZHOHMJP-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(3,4-dimethoxyphenyl)methyl]pentanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)CCCC)C1=CC=C(OC)C(OC)=C1 FYKDHTLZHOHMJP-UHFFFAOYSA-N 0.000 claims 1
- ZMWXCFUGRBATKA-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(3,4-dimethoxyphenyl)methyl]propanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)CC)C1=CC=C(OC)C(OC)=C1 ZMWXCFUGRBATKA-UHFFFAOYSA-N 0.000 claims 1
- CBYHMZRBLIHVFI-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(3,4-dimethoxyphenyl)methyl]pyridine-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(C=1C(=C2N=CC=CC2=C(Cl)C=1)O)NC(=O)C1=CC=CC=N1 CBYHMZRBLIHVFI-UHFFFAOYSA-N 0.000 claims 1
- JVQDKPGGCMHFRG-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(3,4-dimethoxyphenyl)methyl]pyridine-3-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(C=1C(=C2N=CC=CC2=C(Cl)C=1)O)NC(=O)C1=CC=CN=C1 JVQDKPGGCMHFRG-UHFFFAOYSA-N 0.000 claims 1
- SCQLWZOWCFUPSE-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(3-hydroxyphenyl)methyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C1=CC=CC(O)=C1 SCQLWZOWCFUPSE-UHFFFAOYSA-N 0.000 claims 1
- AUTOYIDLVMFZPX-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(4-chlorophenyl)methyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C1=CC=C(Cl)C=C1 AUTOYIDLVMFZPX-UHFFFAOYSA-N 0.000 claims 1
- VTPUBOAPEQSTFS-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(4-chlorophenyl)methyl]butanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)CCC)C1=CC=C(Cl)C=C1 VTPUBOAPEQSTFS-UHFFFAOYSA-N 0.000 claims 1
- GGYJSXXRHXMBCY-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(4-cyanophenyl)methyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C1=CC=C(C#N)C=C1 GGYJSXXRHXMBCY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- RVDHGGKEOWVTGO-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(4-methoxyphenyl)methyl]butanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)CCC)C1=CC=C(OC)C=C1 RVDHGGKEOWVTGO-UHFFFAOYSA-N 0.000 claims 1
- PZIGIJXIFUBGOH-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(4-methoxyphenyl)methyl]pentanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)CCCC)C1=CC=C(OC)C=C1 PZIGIJXIFUBGOH-UHFFFAOYSA-N 0.000 claims 1
- NSHKLFCPKDWPFW-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(4-methylphenyl)methyl]-2-methylpropanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C(C)C)C1=CC=C(C)C=C1 NSHKLFCPKDWPFW-UHFFFAOYSA-N 0.000 claims 1
- NTUQQFGFRQITLD-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(4-methylphenyl)methyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C1=CC=C(C)C=C1 NTUQQFGFRQITLD-UHFFFAOYSA-N 0.000 claims 1
- UVSUHNPGFMUNCC-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(4-methylphenyl)methyl]butanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)CCC)C1=CC=C(C)C=C1 UVSUHNPGFMUNCC-UHFFFAOYSA-N 0.000 claims 1
- ICCASRDXJRTDIJ-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(4-methylphenyl)methyl]pentanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)CCCC)C1=CC=C(C)C=C1 ICCASRDXJRTDIJ-UHFFFAOYSA-N 0.000 claims 1
- BHJWVIQRDPSQPF-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(4-propan-2-ylphenyl)methyl]-2-methylpropanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C(C)C)C1=CC=C(C(C)C)C=C1 BHJWVIQRDPSQPF-UHFFFAOYSA-N 0.000 claims 1
- IPSGXKAFCLXWMU-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(4-propan-2-ylphenyl)methyl]acetamide Chemical compound C1=CC(C(C)C)=CC=C1C(NC(C)=O)C1=CC(Cl)=C(C=CC=N2)C2=C1O IPSGXKAFCLXWMU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- VKOUSUVSULMSJS-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(4-pyridin-2-ylphenyl)methyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C(C=C1)=CC=C1C1=CC=CC=N1 VKOUSUVSULMSJS-UHFFFAOYSA-N 0.000 claims 1
- LHYMZCFJDIJAMJ-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(6-methoxypyridin-3-yl)methyl]acetamide Chemical compound C1=NC(OC)=CC=C1C(NC(C)=O)C1=CC(Cl)=C(C=CC=N2)C2=C1O LHYMZCFJDIJAMJ-UHFFFAOYSA-N 0.000 claims 1
- BQRPYUQFDJOQBA-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(6-morpholin-4-ylpyridin-3-yl)methyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C(C=N1)=CC=C1N1CCOCC1 BQRPYUQFDJOQBA-UHFFFAOYSA-N 0.000 claims 1
- HGCDZBOQEHGLGD-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(8-hydroxyquinolin-2-yl)methyl]acetamide Chemical compound C1=CC=NC2=C(O)C(C(C=3N=C4C(O)=CC=CC4=CC=3)NC(=O)C)=CC(Cl)=C21 HGCDZBOQEHGLGD-UHFFFAOYSA-N 0.000 claims 1
- WVFMBPBMXPRWHY-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(furan-2-yl)methyl]-2-methylpropanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C(C)C)C1=CC=CO1 WVFMBPBMXPRWHY-UHFFFAOYSA-N 0.000 claims 1
- UPLAQKIMKDWICQ-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-(furan-2-yl)methyl]propanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)CC)C1=CC=CO1 UPLAQKIMKDWICQ-UHFFFAOYSA-N 0.000 claims 1
- LHHBXTYLAYAKHI-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-[4-(dimethylamino)phenyl]methyl]butanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)CCC)C1=CC=C(N(C)C)C=C1 LHHBXTYLAYAKHI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- OGOXQDKTBGYXDB-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-phenylmethyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C1=CC=CC=C1 OGOXQDKTBGYXDB-UHFFFAOYSA-N 0.000 claims 1
- RSHNZQIRXYERPR-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-phenylmethyl]butanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)CCC)C1=CC=CC=C1 RSHNZQIRXYERPR-UHFFFAOYSA-N 0.000 claims 1
- QJPPDBAPLCTLOY-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-phenylmethyl]pentanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)CCCC)C1=CC=CC=C1 QJPPDBAPLCTLOY-UHFFFAOYSA-N 0.000 claims 1
- RIYTZYXHQHIITB-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-pyridin-2-ylmethyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C1=CC=CC=N1 RIYTZYXHQHIITB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- QHVGNWSCCBZQFX-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-pyridin-3-ylmethyl]acetamide;hydrochloride Chemical compound Cl.C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C1=CC=CN=C1 QHVGNWSCCBZQFX-UHFFFAOYSA-N 0.000 claims 1
- FHBMRJKJKLXYBZ-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-pyridin-4-ylmethyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C1=CC=NC=C1 FHBMRJKJKLXYBZ-UHFFFAOYSA-N 0.000 claims 1
- LLAYWUYIZHSHNY-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-pyridin-4-ylmethyl]acetamide;hydrochloride Chemical compound Cl.C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C1=CC=NC=C1 LLAYWUYIZHSHNY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- YDOYJKVOIQSHDC-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-quinolin-4-ylmethyl]acetamide Chemical compound C1=CC=C2C(C(C=3C(=C4N=CC=CC4=C(Cl)C=3)O)NC(=O)C)=CC=NC2=C1 YDOYJKVOIQSHDC-UHFFFAOYSA-N 0.000 claims 1
- MUXXALTZLCUMQQ-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-thiophen-2-ylmethyl]-2-methylpropanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C(C)C)C1=CC=CS1 MUXXALTZLCUMQQ-UHFFFAOYSA-N 0.000 claims 1
- SRLJNSQTNHJWPA-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-thiophen-2-ylmethyl]-3-phenylpropanamide Chemical compound C1=C(Cl)C2=CC=CN=C2C(O)=C1C(C=1SC=CC=1)NC(=O)CCC1=CC=CC=C1 SRLJNSQTNHJWPA-UHFFFAOYSA-N 0.000 claims 1
- UZLBHGBBHNHZNS-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-thiophen-2-ylmethyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)C1=CC=CS1 UZLBHGBBHNHZNS-UHFFFAOYSA-N 0.000 claims 1
- YGWFEEPDVXIOHB-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-thiophen-2-ylmethyl]butanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)CCC)C1=CC=CS1 YGWFEEPDVXIOHB-UHFFFAOYSA-N 0.000 claims 1
- YXHNNUCABLCYSD-UHFFFAOYSA-N n-[(5-chloro-8-hydroxyquinolin-7-yl)-thiophen-2-ylmethyl]pentanamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)CCCC)C1=CC=CS1 YXHNNUCABLCYSD-UHFFFAOYSA-N 0.000 claims 1
- RFCCQJJHFAITGH-UHFFFAOYSA-N n-[(8-hydroxyquinolin-7-yl)-(4-methoxyphenyl)methyl]-3-phenylpropanamide Chemical compound C1=CC(OC)=CC=C1C(C=1C(=C2N=CC=CC2=CC=1)O)NC(=O)CCC1=CC=CC=C1 RFCCQJJHFAITGH-UHFFFAOYSA-N 0.000 claims 1
- HLKCSMARQNIDMS-UHFFFAOYSA-N n-[(8-hydroxyquinolin-7-yl)-(4-methoxyphenyl)methyl]cyclohexanecarboxamide Chemical compound C1=CC(OC)=CC=C1C(C=1C(=C2N=CC=CC2=CC=1)O)NC(=O)C1CCCCC1 HLKCSMARQNIDMS-UHFFFAOYSA-N 0.000 claims 1
- NTOMTWHLAMHYRJ-UHFFFAOYSA-N n-[(8-hydroxyquinolin-7-yl)-(4-methylphenyl)methyl]-3-phenylpropanamide Chemical compound C1=CC(C)=CC=C1C(C=1C(=C2N=CC=CC2=CC=1)O)NC(=O)CCC1=CC=CC=C1 NTOMTWHLAMHYRJ-UHFFFAOYSA-N 0.000 claims 1
- GFTQCVMCUADNIJ-UHFFFAOYSA-N n-[(8-hydroxyquinolin-7-yl)-(4-propan-2-ylphenyl)methyl]-3-methylbutanamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(NC(=O)CC(C)C)C1=CC=C(C(C)C)C=C1 GFTQCVMCUADNIJ-UHFFFAOYSA-N 0.000 claims 1
- MWQWZIWMSWUMLW-UHFFFAOYSA-N n-[(8-hydroxyquinolin-7-yl)-(4-propan-2-ylphenyl)methyl]acetamide Chemical compound C1=CC(C(C)C)=CC=C1C(NC(C)=O)C1=CC=C(C=CC=N2)C2=C1O MWQWZIWMSWUMLW-UHFFFAOYSA-N 0.000 claims 1
- SXKDUVDASYEAQZ-UHFFFAOYSA-N n-[(8-hydroxyquinolin-7-yl)-(4-propan-2-ylphenyl)methyl]pentanamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(NC(=O)CCCC)C1=CC=C(C(C)C)C=C1 SXKDUVDASYEAQZ-UHFFFAOYSA-N 0.000 claims 1
- UECHRCZFFNFJCG-UHFFFAOYSA-N n-[(8-hydroxyquinolin-7-yl)-phenylmethyl]-3-methylbutanamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(NC(=O)CC(C)C)C1=CC=CC=C1 UECHRCZFFNFJCG-UHFFFAOYSA-N 0.000 claims 1
- MDLWLVWPYPTEPB-UHFFFAOYSA-N n-[(8-hydroxyquinolin-7-yl)-thiophen-2-ylmethyl]-3-methylbutanamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(NC(=O)CC(C)C)C1=CC=CS1 MDLWLVWPYPTEPB-UHFFFAOYSA-N 0.000 claims 1
- JCMVPOVHTZCXCY-UHFFFAOYSA-N n-[(8-hydroxyquinolin-7-yl)-thiophen-2-ylmethyl]cyclohexanecarboxamide Chemical compound C1=CC2=CC=CN=C2C(O)=C1C(C=1SC=CC=1)NC(=O)C1CCCCC1 JCMVPOVHTZCXCY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- AZEPADTWZLWBJX-UHFFFAOYSA-N n-[1-(5-chloro-8-hydroxyquinolin-7-yl)-2-phenylethyl]acetamide Chemical compound C=1C(Cl)=C2C=CC=NC2=C(O)C=1C(NC(=O)C)CC1=CC=CC=C1 AZEPADTWZLWBJX-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- KUCRHUULIMRKAL-UHFFFAOYSA-N n-[2-(5-chloro-8-hydroxyquinolin-7-yl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1C1=CC(Cl)=C(C=CC=N2)C2=C1O KUCRHUULIMRKAL-UHFFFAOYSA-N 0.000 claims 1
- WTVLPUWOVVAQKG-UHFFFAOYSA-N n-[[4-(diethylamino)phenyl]-(8-hydroxyquinolin-7-yl)methyl]pentanamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(NC(=O)CCCC)C1=CC=C(N(CC)CC)C=C1 WTVLPUWOVVAQKG-UHFFFAOYSA-N 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- 230000002685 pulmonary effect Effects 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 210000000278 spinal cord Anatomy 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
Classifications
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
-
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| EP2325171B1 (fr) | 2005-05-26 | 2013-10-09 | Aldexa Therapeutics, Inc. | Dérivés de quinoline pour le traitement des maladies rétiniennes |
| US10301265B2 (en) * | 2008-05-28 | 2019-05-28 | Virginia I. Roxas-Duncan | Small molecule inhibitors of botulinum neurotoxins |
| US9000009B2 (en) * | 2008-12-10 | 2015-04-07 | The Trustees Of The University Of Pennsylvania | Small molecule activators of mitochondrial function |
| WO2010129918A1 (fr) * | 2009-05-07 | 2010-11-11 | Regents Of The University Of Minnesota | Promédicaments à base de triptolide |
| US9150600B2 (en) | 2009-05-07 | 2015-10-06 | Regents Of The University Of Minnesota | Triptolide 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 |
| CA2782015C (fr) | 2009-12-11 | 2020-08-25 | Neuron Systems, Inc. | Compositions ophthalmiques topiques et methodes de traitement de la degenerescence maculaire |
| 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 |
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| US8658170B2 (en) | 2010-01-06 | 2014-02-25 | Joseph P. Errico | Combination therapy with MDM2 and EFGR inhibitors |
| JP2013516479A (ja) | 2010-01-06 | 2013-05-13 | ジョゼフ・ピー・エリコ | 標的薬物を開発する方法および組成物 |
| WO2011106226A2 (fr) * | 2010-02-23 | 2011-09-01 | Cornell University | Inhibiteurs de la prolylhydroxylase et procédés d'utilisation |
| HUP1000243A2 (en) * | 2010-05-06 | 2012-01-30 | Avidin Kft | 8-hidroxy-quinoline derivatives |
| AU2011255627A1 (en) * | 2010-05-18 | 2012-12-06 | Eastern Virginia Medical School | Inhibitors of human 12-lipoxygenase |
| JP2014527511A (ja) | 2011-06-24 | 2014-10-16 | アムジエン・インコーポレーテツド | Ｔｒｐｍ８拮抗剤及び治療におけるそれらの使用 |
| WO2012177896A1 (fr) | 2011-06-24 | 2012-12-27 | Amgen Inc. | Antagonistes de trpm8 et leur utilisation dans le cadre thérapeutique |
| 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 |
| KR102435676B1 (ko) | 2013-01-23 | 2022-08-24 | 알데이라 테라퓨틱스, 아이엔씨. | 독성 알데히드 관련된 질병 및 치료 |
| JP6266023B2 (ja) | 2013-01-25 | 2018-01-24 | アルデイラ セラピューティクス， インコーポレイテッド | 黄斑変性症の処置における新規トラップ |
| RU2642466C2 (ru) * | 2013-04-02 | 2018-01-25 | Аннцзи Фармасьютикал Ко., Лтд. | Многофункциональные производные хинолина в качестве антинейродегенеративных агентов |
| 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 |
| WO2017035077A1 (fr) | 2015-08-21 | 2017-03-02 | Aldeyra Therapeutics, Inc. | Composés deutérés et leurs utilisations |
| 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 |
| CA3022665A1 (fr) | 2016-05-09 | 2017-11-16 | Aldeyra Therapeutics, Inc. | Polytherapie de troubles et de maladies inflammatoires oculaires |
| EP3508223B1 (fr) * | 2016-08-31 | 2022-05-04 | Kyoto University | 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 |
| CA3054811A1 (fr) | 2017-03-16 | 2018-09-20 | Aldeyra Therapeutics, Inc. | Composes polymorphes et leurs utilisations |
| EP3388419A1 (fr) | 2017-04-12 | 2018-10-17 | Leadiant Biosciences SA | Inhibiteurs de gli1 et utilisations associées |
| CN111356451A (zh) | 2017-10-10 | 2020-06-30 | 奥尔德拉医疗公司 | 炎性病症的治疗 |
| CN111803499B (zh) * | 2018-06-13 | 2021-09-14 | 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ⅱ |
| WO2020033344A1 (fr) | 2018-08-06 | 2020-02-13 | Aldeyra Therapeutics, Inc. | Composés polymorphes et leurs utilisations |
| EP3866802A1 (fr) * | 2018-10-17 | 2021-08-25 | Duke University | Inhibiteurs de la quinone réductase 2 destinés à être utilisés en tant qu'agents neuroprotecteurs |
| KR20220097438A (ko) * | 2019-11-01 | 2022-07-07 | 얀센 바이오테크 인코포레이티드 | 암, 자가면역, 및 염증성 질환의 치료를 위한 다이하이드로오로테이트 데하이드로게나제(dhodh) 억제제로서의 플루오르화 퀴놀린 및 퀴녹살린 유도체 |
| WO2021178721A1 (fr) * | 2020-03-04 | 2021-09-10 | University Of Kentucky Research Foundation | Inhibiteurs n-benzhydrylacétamide substitués d'histone déméthylases à domaine jumanji pour le traitement du cancer |
| 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 |
| WO2022169834A2 (fr) * | 2021-02-02 | 2022-08-11 | The Regents Of The University Of Michigan | Inhibiteurs à petites molécules de grp78 et leurs utilisations |
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|---|---|---|---|---|
| EP0927164A1 (fr) * | 1996-09-10 | 1999-07-07 | PHARMACIA & UPJOHN COMPANY | 8-hydroxyquinoleines 7-substituees utilisees comme agents antiviraux |
| CZ20031028A3 (cs) * | 2000-10-12 | 2003-08-13 | Merck & Co., Inc. | Aza- a polyazanaftalenylkarboxamidy |
| CN1659143A (zh) * | 2001-03-01 | 2005-08-24 | 盐野义制药株式会社 | 具有hiv整合酶抑制活性的含氮杂芳基化合物 |
| AU2002950217A0 (en) * | 2002-07-16 | 2002-09-12 | Prana Biotechnology Limited | 8- Hydroxy Quinoline Derivatives |
-
2007
- 2007-07-25 WO PCT/CA2007/001324 patent/WO2008014602A1/fr active Application Filing
- 2007-07-25 JP JP2009521076A patent/JP2009544631A/ja active Pending
- 2007-07-25 CA CA002658793A patent/CA2658793A1/fr not_active Abandoned
- 2007-07-25 RU RU2009106461/04A patent/RU2009106461A/ru not_active Application Discontinuation
- 2007-07-25 CN CNA2007800346135A patent/CN101611009A/zh active Pending
- 2007-07-25 AU AU2007280984A patent/AU2007280984A1/en not_active Abandoned
- 2007-07-25 EP EP07815779A patent/EP2079699A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CA2658793A1 (fr) | 2008-02-07 |
| JP2009544631A (ja) | 2009-12-17 |
| EP2079699A1 (fr) | 2009-07-22 |
| CN101611009A (zh) | 2009-12-23 |
| AU2007280984A1 (en) | 2008-02-07 |
| WO2008014602A1 (fr) | 2008-02-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20111004 |