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
-
- 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
- A61P11/16—Central respiratory analeptics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/04—Artificial tears; Irrigation solutions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/12—Ophthalmic agents for cataracts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P35/00—Antineoplastic agents
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- 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
- C07D215/28—Alcohols; Ethers thereof with halogen atoms or nitro radicals in positions 5, 6 or 7
-
- 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
- C07D215/32—Esters
-
- 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
- C07D215/38—Nitrogen atoms
-
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/60—Quinoline or hydrogenated quinoline ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurology (AREA)
- Ophthalmology & Optometry (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pulmonology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Vascular Medicine (AREA)
- Psychiatry (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83293706P | 2006-07-25 | 2006-07-25 | |
| US60/832,937 | 2006-07-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2009106461A true RU2009106461A (ru) | 2010-08-27 |
Family
ID=38996820
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2009106461/04A RU2009106461A (ru) | 2006-07-25 | 2007-07-25 | Хинолиновые производные |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP2079699A1 (de) |
| JP (1) | JP2009544631A (de) |
| CN (1) | CN101611009A (de) |
| AU (1) | AU2007280984A1 (de) |
| CA (1) | CA2658793A1 (de) |
| RU (1) | RU2009106461A (de) |
| WO (1) | WO2008014602A1 (de) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1888548B1 (de) | 2005-05-26 | 2012-08-22 | Neuron Systems, Inc | Chinolinderivat zur Behandlung von Netzhauterkrankungen |
| WO2009151972A1 (en) * | 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 | 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 |
| 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 (en) | 2009-10-01 | 2011-04-07 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Quinazolin-4-amine derivatives; and methods of use |
| US9814701B2 (en) | 2009-12-11 | 2017-11-14 | Aldeyra Therapeutics, Inc. | Compositions and methods for the treatment of macular degeneration |
| EP2345642A1 (de) * | 2009-12-29 | 2011-07-20 | Polichem S.A. | Sekundäre 8-Hydroxychinolin-7-Carboxamid-Derivate zur Verwendung als Fungizid |
| EP2345641A1 (de) * | 2009-12-29 | 2011-07-20 | Polichem S.A. | Neue sekundäre 8-Hydroxychinolin-7-Carboxamid-Derivate |
| US8658170B2 (en) | 2010-01-06 | 2014-02-25 | Joseph P. Errico | Combination therapy with MDM2 and EFGR inhibitors |
| EP2521553A4 (de) * | 2010-01-06 | 2013-08-28 | Errico Joseph P | Verfahren und zusammensetzungen für gezielte wirkstoffentwicklung |
| 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 (en) * | 2010-05-18 | 2011-11-24 | The United States Of America, As Represented By The Secretary, Departmen T Of Health And Human Services | Inhibitors of human 12-lipoxygenase |
| MX2013015058A (es) | 2011-06-24 | 2014-01-20 | Amgen Inc | Antagonistas de melastatina 8 de potencial receptor transitorio y su uso en tratamientos. |
| CA2839699A1 (en) | 2011-06-24 | 2012-12-27 | Amgen Inc. | Trpm8 antagonists and their use in treatments |
| 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 (ja) * | 2016-04-07 | 2017-10-12 | 国立大学法人京都大学 | スプライシングの改変に関する化合物及び医薬組成物 |
| MX2018013472A (es) | 2016-05-09 | 2019-02-28 | Aldeyra Therapeutics Inc | Tratamiento de combinacion de trastornos y enfermedades inflamatorios oculares. |
| WO2018043674A1 (ja) * | 2016-08-31 | 2018-03-08 | 国立大学法人京都大学 | 神経新生を活性化するための組成物 |
| WO2018108627A1 (de) | 2016-12-12 | 2018-06-21 | Bayer Cropscience Aktiengesellschaft | Verwendung substituierter indolinylmethylsulfonamide oder deren salze zur steigerung der stresstoleranz in pflanzen |
| EP3596040B1 (de) | 2017-03-16 | 2023-10-11 | Aldeyra Therapeutics, Inc. | Polymorphe salze von 6-chlor-3amino-2-(2-hydroxypropyl)chinolin und verwendungen davon |
| EP3388419A1 (de) | 2017-04-12 | 2018-10-17 | Leadiant Biosciences SA | Gli1-inhibitoren und deren verwendungen |
| 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 (de) | 2019-05-02 | 2023-01-11 | Aldeyra Therapeutics, Inc. | Polymorphe verbindungen und verwendungen davon |
| 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 (en) | 2020-05-13 | 2021-11-18 | Aldeyra Therapeutics, Inc. | Pharmaceutical formulations and uses thereof |
| 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 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 (de) * | 2001-03-01 | 2012-08-29 | Shionogi&Co., Ltd. | Stickstoffhaltige Heteroarylverbindungen mit HIV-Integrase inhibierender Wirkung |
| AU2002950217A0 (en) * | 2002-07-16 | 2002-09-12 | Prana Biotechnology Limited | 8- Hydroxy Quinoline Derivatives |
-
2007
- 2007-07-25 CA CA002658793A patent/CA2658793A1/en not_active Abandoned
- 2007-07-25 WO PCT/CA2007/001324 patent/WO2008014602A1/en 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/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CA2658793A1 (en) | 2008-02-07 |
| AU2007280984A1 (en) | 2008-02-07 |
| WO2008014602A1 (en) | 2008-02-07 |
| EP2079699A1 (de) | 2009-07-22 |
| JP2009544631A (ja) | 2009-12-17 |
| CN101611009A (zh) | 2009-12-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2009106461A (ru) | Хинолиновые производные | |
| RU2019131111A (ru) | ПРОИЗВОДНОЕ ГЕТЕРОАРИЛ[4,3-с]ПИРИМИДИН-5-АМИНА, СПОСОБ ЕГО ПОЛУЧЕНИЯ И ЕГО МЕДИЦИНСКИЕ ПРИМЕНЕНИЯ | |
| DE60131844T2 (de) | 2-amino-3-(alkyl)-pyrimidonderivate als gsk3.beta.-hemmer | |
| JP2013532668A5 (de) | ||
| KR101861942B1 (ko) | 신경 발생을 자극할 수 있는 n-페닐-락탐 유도체 및 이의 신경 장애 치료에서의 용도 | |
| CA2722776A1 (en) | Nmda receptor antagonists for the treatment of neuropsychiatric disorders | |
| CN106795165B (zh) | 咪唑并哒嗪化合物 | |
| JP2010518153A5 (de) | ||
| JP2005516067A5 (de) | ||
| RU2002125495A (ru) | Гидроксифенил-пиперидин-4-илиден-метил-бензамидные производные для лечения боли | |
| CN103270023A (zh) | 作为用于治疗疾病诸如癌症的nampt 抑制剂的4-{[(吡啶-3-基-甲基)氨基羰基]氨基}苯-砜衍生物 | |
| JP5916730B2 (ja) | アミド化合物 | |
| US20140243350A1 (en) | Use of serotonin receptor agonists for treatment of movement disorders | |
| MX2008009655A (es) | Metodo para tratar o reducir los sintomas de la esquizofrenia. | |
| CA2420568A1 (en) | Pharmaceutically active benzsulfonamide derivatives as inhibitors of protein junkinases | |
| US20190328736A1 (en) | Methods Of Treating Dyskinesia And Related Disorders | |
| JP2019537592A5 (de) | ||
| JP2005505583A5 (de) | ||
| RU2006142896A (ru) | Замещенные енаминоны, их производные и их применение | |
| JP6273349B2 (ja) | ニトロキソリンの塩基付加塩及びその使用 | |
| RU2007112501A (ru) | Бензимидазольные производные, содержащие их композиции, их получение и применение | |
| JP2020531574A (ja) | 化合物、その医薬組成物及びその使用及び応用 | |
| KR20130090144A (ko) | 신규한 피리미딘계 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 포함하는 ｒａｇｅ 수용체 관련 질환의 예방 또는 치료용 약학적 조성물 | |
| RU2002114343A (ru) | Новые соединения | |
| EP4228650A1 (de) | Inhalierte formulierungen von pgdh-inhibitoren und verfahren zur verwendung davon |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20111004 |