JPWO2022138888A5 - - Google Patents
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- JPWO2022138888A5 JPWO2022138888A5 JP2021577857A JP2021577857A JPWO2022138888A5 JP WO2022138888 A5 JPWO2022138888 A5 JP WO2022138888A5 JP 2021577857 A JP2021577857 A JP 2021577857A JP 2021577857 A JP2021577857 A JP 2021577857A JP WO2022138888 A5 JPWO2022138888 A5 JP WO2022138888A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- tetrahydroquinolin
- phenyl
- atom
- hydrogen atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 206
- 125000004432 carbon atom Chemical group C* 0.000 claims 96
- 229910052731 fluorine Inorganic materials 0.000 claims 61
- 125000001153 fluoro group Chemical group F* 0.000 claims 61
- -1 4-hydroxymethylphenyl group Chemical group 0.000 claims 54
- 125000000217 alkyl group Chemical group 0.000 claims 51
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 37
- 229910052801 chlorine Inorganic materials 0.000 claims 22
- 125000001309 chloro group Chemical group Cl* 0.000 claims 22
- 125000003545 alkoxy group Chemical group 0.000 claims 19
- 229910052757 nitrogen Inorganic materials 0.000 claims 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 19
- 125000004430 oxygen atom Chemical group O* 0.000 claims 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 15
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 13
- 150000003530 tetrahydroquinolines Chemical class 0.000 claims 13
- 125000002393 azetidinyl group Chemical group 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 9
- 125000004193 piperazinyl group Chemical group 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 8
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 8
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical group O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 7
- FJEVKSNLTIDJED-UHFFFAOYSA-N 1-(3-hydroxyazetidin-1-yl)-2-(2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)ethanone Chemical compound OC(C1)CN1C(CC(C=C1CC2)=CC=C1NC2C1=CC=CC=C1)=O FJEVKSNLTIDJED-UHFFFAOYSA-N 0.000 claims 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 6
- VUWXUFSLPKGYKI-UHFFFAOYSA-N 4-(1,2,3,4-tetrahydroquinolin-2-yl)benzamide Chemical compound NC(C1=CC=C(C2NC3=CC=CC=C3CC2)C=C1)=O VUWXUFSLPKGYKI-UHFFFAOYSA-N 0.000 claims 6
- GURZVBOXVCFIEH-UHFFFAOYSA-N 4-(1,2,3,4-tetrahydroquinolin-2-yl)benzenesulfonamide Chemical compound NS(C1=CC=C(C2NC3=CC=CC=C3CC2)C=C1)(=O)=O GURZVBOXVCFIEH-UHFFFAOYSA-N 0.000 claims 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000003386 piperidinyl group Chemical group 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 5
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical group O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims 5
- KBYVOJODXSCTBW-UHFFFAOYSA-N (2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)urea Chemical compound NC(NC(C=C1CC2)=CC=C1NC2C1=CC=CC=C1)=O KBYVOJODXSCTBW-UHFFFAOYSA-N 0.000 claims 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical group CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 4
- UMPFHPQRDOXERT-UHFFFAOYSA-N 1-tert-butyl-3-(2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)urea Chemical compound CC(C)(C)NC(NC(C=C1CC2)=CC=C1NC2C1=CC=CC=C1)=O UMPFHPQRDOXERT-UHFFFAOYSA-N 0.000 claims 4
- OKCGWVRITQWJFQ-UHFFFAOYSA-N 2,2-dimethyl-N-(2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)propanamide Chemical compound CC(C)(C)C(NC(C=C1CC2)=CC=C1NC2C1=CC=CC=C1)=O OKCGWVRITQWJFQ-UHFFFAOYSA-N 0.000 claims 4
- DCFOXIZCQPXKQQ-UHFFFAOYSA-N 2-(2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)acetamide Chemical compound NC(CC(C=C1CC2)=CC=C1NC2C1=CC=CC=C1)=O DCFOXIZCQPXKQQ-UHFFFAOYSA-N 0.000 claims 4
- YGUOUWSREMLQBK-UHFFFAOYSA-N 4-[(2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)methyl]morpholine Chemical compound C(C(C=C1CC2)=CC=C1NC2C1=CC=CC=C1)N1CCOCC1 YGUOUWSREMLQBK-UHFFFAOYSA-N 0.000 claims 4
- BTXHOJYRTXKZOY-UHFFFAOYSA-N 5-(1,2,3,4-tetrahydroquinolin-2-yl)-2,3-dihydroisoindol-1-one Chemical compound O=C1NCC2=CC(C3NC4=CC=CC=C4CC3)=CC=C12 BTXHOJYRTXKZOY-UHFFFAOYSA-N 0.000 claims 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 4
- BLRAEFFHSHGCFY-UHFFFAOYSA-N N-(2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)acetamide Chemical compound CC(NC(C=C1CC2)=CC=C1NC2C1=CC=CC=C1)=O BLRAEFFHSHGCFY-UHFFFAOYSA-N 0.000 claims 4
- ZWTIQTZATYFULM-UHFFFAOYSA-N N-(2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)methanesulfonamide Chemical compound CS(NC(C=C1CC2)=CC=C1NC2C1=CC=CC=C1)(=O)=O ZWTIQTZATYFULM-UHFFFAOYSA-N 0.000 claims 4
- AGTLSVHZPFXXPO-UHFFFAOYSA-N [4-(1,2,3,4-tetrahydroquinolin-2-yl)phenyl]methanol Chemical compound OCC1=CC=C(C2NC3=CC=CC=C3CC2)C=C1 AGTLSVHZPFXXPO-UHFFFAOYSA-N 0.000 claims 4
- 239000004480 active ingredient Substances 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000002541 furyl group Chemical group 0.000 claims 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N gamma-butyrolactam Natural products O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims 4
- 125000002971 oxazolyl group Chemical group 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- HNJBEVLQSNELDL-YZRHJBSPSA-N pyrrolidin-2-one Chemical group O=C1CC[14CH2]N1 HNJBEVLQSNELDL-YZRHJBSPSA-N 0.000 claims 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims 4
- OHRZWGGQKHJSHN-UHFFFAOYSA-N tert-butyl N-(2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)carbamate Chemical compound CC(C)(C)OC(NC(C=C1CC2)=CC=C1NC2C1=CC=CC=C1)=O OHRZWGGQKHJSHN-UHFFFAOYSA-N 0.000 claims 4
- 125000000335 thiazolyl group Chemical group 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- QAUGNTRYNWFNBL-UHFFFAOYSA-N 2-phenyl-1,2,3,4-tetrahydroquinoline Chemical compound C1CC2=CC=CC=C2NC1C1=CC=CC=C1 QAUGNTRYNWFNBL-UHFFFAOYSA-N 0.000 claims 3
- QUHVRXKSQHIZNV-UHFFFAOYSA-N 3,3-difluoroazetidine Chemical group FC1(F)CNC1 QUHVRXKSQHIZNV-UHFFFAOYSA-N 0.000 claims 3
- RLVVIGIYIMDCAU-UHFFFAOYSA-N 3,3-dimethylazetidine Chemical group CC1(C)CNC1 RLVVIGIYIMDCAU-UHFFFAOYSA-N 0.000 claims 3
- AVPAYFOQPGPSCC-UHFFFAOYSA-N 3-methoxyazetidine Chemical group COC1CNC1 AVPAYFOQPGPSCC-UHFFFAOYSA-N 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- GMWFCJXSQQHBPI-UHFFFAOYSA-N azetidin-3-ol Chemical group OC1CNC1 GMWFCJXSQQHBPI-UHFFFAOYSA-N 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- PQJCMCAEPNDTHE-UHFFFAOYSA-N (2-phenyl-1,2,3,4-tetrahydroquinolin-5-yl)methanol Chemical compound OCC1=C(CCC(C2=CC=CC=C2)N2)C2=CC=C1 PQJCMCAEPNDTHE-UHFFFAOYSA-N 0.000 claims 2
- GMKZNAIJHLZYCC-UHFFFAOYSA-N (2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)methanol Chemical compound OCC(C=C1CC2)=CC=C1NC2C1=CC=CC=C1 GMKZNAIJHLZYCC-UHFFFAOYSA-N 0.000 claims 2
- PHOGZPMFHLHRDH-UHFFFAOYSA-N (2-phenyl-1,2,3,4-tetrahydroquinolin-7-yl)methanol Chemical compound OCC1=CC=C(CCC(C2=CC=CC=C2)N2)C2=C1 PHOGZPMFHLHRDH-UHFFFAOYSA-N 0.000 claims 2
- JOYFZHQLDJBVOQ-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-(1,2,3,4-tetrahydroquinolin-2-yl)phenyl]methanone Chemical compound CN(CC1)CCN1C(C1=CC=C(C2NC3=CC=CC=C3CC2)C=C1)=O JOYFZHQLDJBVOQ-UHFFFAOYSA-N 0.000 claims 2
- YKWPZUCBWXRZGV-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-(2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)ethanone Chemical compound O=C(CC(C=C1CC2)=CC=C1NC2C1=CC=CC=C1)N(C1)CC1(F)F YKWPZUCBWXRZGV-UHFFFAOYSA-N 0.000 claims 2
- QTJJLKLVCCRWPR-UHFFFAOYSA-N 1-(3-methoxyazetidin-1-yl)-2-(2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)ethanone Chemical compound COC(C1)CN1C(CC(C=C1CC2)=CC=C1NC2C1=CC=CC=C1)=O QTJJLKLVCCRWPR-UHFFFAOYSA-N 0.000 claims 2
- COFQPUQIOWWUIE-UHFFFAOYSA-N 1-methyl-6-(1,2,3,4-tetrahydroquinolin-2-yl)-3,4-dihydroquinolin-2-one Chemical compound CN1C2=CC=C(C3NC4=CC=CC=C4CC3)C=C2CCC1=O COFQPUQIOWWUIE-UHFFFAOYSA-N 0.000 claims 2
- FTDKCCONIQQDPX-UHFFFAOYSA-N 2-(1,2,3,4-tetrahydroquinolin-2-yl)benzenesulfonamide Chemical compound NS(C1=C(C2NC3=CC=CC=C3CC2)C=CC=C1)(=O)=O FTDKCCONIQQDPX-UHFFFAOYSA-N 0.000 claims 2
- ZIGAUXVRTWLLSD-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-1,2,3,4-tetrahydroquinoline Chemical compound C1OC(C=C(C2NC3=CC=CC=C3CC2)C=C2)=C2O1 ZIGAUXVRTWLLSD-UHFFFAOYSA-N 0.000 claims 2
- KLYHVKDWMDNQGO-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-6-methoxy-1,2,3,4-tetrahydroquinoline Chemical compound COC(C=C1CC2)=CC=C1NC2C(C=C1)=CC2=C1OCO2 KLYHVKDWMDNQGO-UHFFFAOYSA-N 0.000 claims 2
- BOFRZRNYLNLNQS-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-1,2,3,4-tetrahydroquinoline Chemical compound C1=NN(C)C=C1C1NC2=CC=CC=C2CC1 BOFRZRNYLNLNQS-UHFFFAOYSA-N 0.000 claims 2
- DHUATWKMZXAYEG-UHFFFAOYSA-N 2-(2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)-1-piperazin-1-ylethanone Chemical compound O=C(CC(C=C1CC2)=CC=C1NC2C1=CC=CC=C1)N1CCNCC1 DHUATWKMZXAYEG-UHFFFAOYSA-N 0.000 claims 2
- BIXKNASFBVHWEC-UHFFFAOYSA-N 2-(2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)propan-2-ol Chemical compound CC(C)(C(C=C1CC2)=CC=C1NC2C1=CC=CC=C1)O BIXKNASFBVHWEC-UHFFFAOYSA-N 0.000 claims 2
- ODOCNGAMZXMQQH-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-1,2,3,4-tetrahydroquinoline Chemical compound CS(C1=CC=C(C2NC3=CC=CC=C3CC2)C=C1)(=O)=O ODOCNGAMZXMQQH-UHFFFAOYSA-N 0.000 claims 2
- YXWZKGWLCMMACF-UHFFFAOYSA-N 2-[4-(1,2,3,4-tetrahydroquinolin-2-yl)phenyl]propan-2-ol Chemical compound CC(C)(C1=CC=C(C2NC3=CC=CC=C3CC2)C=C1)O YXWZKGWLCMMACF-UHFFFAOYSA-N 0.000 claims 2
- NFDIPSWQRJZVTL-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]-1,2,3,4-tetrahydroquinoline Chemical compound FC(OC1=CC=C(C2NC3=CC=CC=C3CC2)C=C1)(F)F NFDIPSWQRJZVTL-UHFFFAOYSA-N 0.000 claims 2
- DKYZUMQZYONNLJ-UHFFFAOYSA-N 2-phenyl-1,2,3,4-tetrahydroquinolin-6-amine Chemical compound NC(C=C1CC2)=CC=C1NC2C1=CC=CC=C1 DKYZUMQZYONNLJ-UHFFFAOYSA-N 0.000 claims 2
- JSVOTMDZUQSKPP-UHFFFAOYSA-N 2-phenyl-6-(trifluoromethoxy)-1,2,3,4-tetrahydroquinoline Chemical compound FC(OC(C=C1CC2)=CC=C1NC2C1=CC=CC=C1)(F)F JSVOTMDZUQSKPP-UHFFFAOYSA-N 0.000 claims 2
- MZCLETFZZXITLQ-UHFFFAOYSA-N 2-phenyl-6-piperidin-1-yl-1,2,3,4-tetrahydroquinoline Chemical compound C(CC1)CCN1C(C=C1CC2)=CC=C1NC2C1=CC=CC=C1 MZCLETFZZXITLQ-UHFFFAOYSA-N 0.000 claims 2
- CVPYCNUJKCTAPS-UHFFFAOYSA-N 2-phenyl-6-propan-2-yl-1,2,3,4-tetrahydroquinoline Chemical compound CC(C)C(C=C1CC2)=CC=C1NC2C1=CC=CC=C1 CVPYCNUJKCTAPS-UHFFFAOYSA-N 0.000 claims 2
- MVFKLUIPIMUMOQ-UHFFFAOYSA-N 3-(1,2,3,4-tetrahydroquinolin-2-yl)benzenesulfonamide Chemical compound NS(C1=CC=CC(C2NC3=CC=CC=C3CC2)=C1)(=O)=O MVFKLUIPIMUMOQ-UHFFFAOYSA-N 0.000 claims 2
- CDNJIRLEVISZHK-UHFFFAOYSA-N 3-(1,2,3,4-tetrahydroquinolin-2-yl)benzonitrile Chemical compound N#CC1=CC(C2NC3=CC=CC=C3CC2)=CC=C1 CDNJIRLEVISZHK-UHFFFAOYSA-N 0.000 claims 2
- HZHPXUUSNAROKA-UHFFFAOYSA-N 3-(2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)oxetan-3-ol Chemical compound OC1(COC1)C(C=C1CC2)=CC=C1NC2C1=CC=CC=C1 HZHPXUUSNAROKA-UHFFFAOYSA-N 0.000 claims 2
- AILSQIUVXDNOGH-UHFFFAOYSA-N 4-(1,2,3,4-tetrahydroquinolin-3-yl)benzenesulfonamide Chemical compound NS(C1=CC=C(C(C2)CNC3=C2C=CC=C3)C=C1)(=O)=O AILSQIUVXDNOGH-UHFFFAOYSA-N 0.000 claims 2
- GXBJMOFCINKTGX-UHFFFAOYSA-N 4-(5-chloro-1,2,3,4-tetrahydroquinolin-2-yl)benzamide Chemical compound NC(C1=CC=C(C2NC3=CC=CC(Cl)=C3CC2)C=C1)=O GXBJMOFCINKTGX-UHFFFAOYSA-N 0.000 claims 2
- QQBHIAHIIGQFNX-UHFFFAOYSA-N 4-(5-chloro-1,2,3,4-tetrahydroquinolin-2-yl)benzenesulfonamide Chemical compound NS(C1=CC=C(C2NC3=CC=CC(Cl)=C3CC2)C=C1)(=O)=O QQBHIAHIIGQFNX-UHFFFAOYSA-N 0.000 claims 2
- OFPNGSHFWAGOPK-UHFFFAOYSA-N 4-(5-fluoro-1,2,3,4-tetrahydroquinolin-2-yl)benzamide Chemical compound NC(C1=CC=C(C2NC3=CC=CC(F)=C3CC2)C=C1)=O OFPNGSHFWAGOPK-UHFFFAOYSA-N 0.000 claims 2
- SPXDDSJKDOTUDC-UHFFFAOYSA-N 4-(5-methyl-1,2,3,4-tetrahydroquinolin-2-yl)benzenesulfonamide Chemical compound CC1=C(CCC(C(C=C2)=CC=C2S(N)(=O)=O)N2)C2=CC=C1 SPXDDSJKDOTUDC-UHFFFAOYSA-N 0.000 claims 2
- GBQFQOCNOXTIHL-UHFFFAOYSA-N 4-(6-chloro-1,2,3,4-tetrahydroquinolin-2-yl)benzamide Chemical compound NC(C1=CC=C(C(CCC2=C3)NC2=CC=C3Cl)C=C1)=O GBQFQOCNOXTIHL-UHFFFAOYSA-N 0.000 claims 2
- UVBOOVJNBDZSDO-UHFFFAOYSA-N 4-(6-chloro-1,2,3,4-tetrahydroquinolin-2-yl)benzenesulfonamide Chemical compound NS(C1=CC=C(C(CCC2=C3)NC2=CC=C3Cl)C=C1)(=O)=O UVBOOVJNBDZSDO-UHFFFAOYSA-N 0.000 claims 2
- BSXCAZNORUDENS-UHFFFAOYSA-N 4-(6-fluoro-1,2,3,4-tetrahydroquinolin-2-yl)benzenesulfonamide Chemical compound NS(C1=CC=C(C(CCC2=C3)NC2=CC=C3F)C=C1)(=O)=O BSXCAZNORUDENS-UHFFFAOYSA-N 0.000 claims 2
- JPEMXVWXGJMXIT-UHFFFAOYSA-N 4-(6-methyl-1,2,3,4-tetrahydroquinolin-2-yl)benzamide Chemical compound CC(C=C1CC2)=CC=C1NC2C(C=C1)=CC=C1C(N)=O JPEMXVWXGJMXIT-UHFFFAOYSA-N 0.000 claims 2
- LVZJGVQFJDGUGY-UHFFFAOYSA-N 4-(6-methyl-1,2,3,4-tetrahydroquinolin-2-yl)benzenesulfonamide Chemical compound CC(C=C1CC2)=CC=C1NC2C(C=C1)=CC=C1S(N)(=O)=O LVZJGVQFJDGUGY-UHFFFAOYSA-N 0.000 claims 2
- MYGOEZWSQHCDLY-UHFFFAOYSA-N 4-(7-fluoro-1,2,3,4-tetrahydroquinolin-2-yl)benzenesulfonamide Chemical compound NS(C1=CC=C(C2NC3=CC(F)=CC=C3CC2)C=C1)(=O)=O MYGOEZWSQHCDLY-UHFFFAOYSA-N 0.000 claims 2
- YGWFDZRWYOLDDX-UHFFFAOYSA-N 4-(7-methyl-1,2,3,4-tetrahydroquinolin-2-yl)benzamide Chemical compound CC1=CC=C(CCC(C(C=C2)=CC=C2C(N)=O)N2)C2=C1 YGWFDZRWYOLDDX-UHFFFAOYSA-N 0.000 claims 2
- URDBZTLDBVMWBU-UHFFFAOYSA-N 6,7-difluoro-2-phenyl-1,2,3,4-tetrahydroquinoline Chemical compound FC(C=C(CCC(C1=CC=CC=C1)N1)C1=C1)=C1F URDBZTLDBVMWBU-UHFFFAOYSA-N 0.000 claims 2
- OYNDJLFTKGHXKI-UHFFFAOYSA-N 6-(1,2,3,4-tetrahydroquinolin-2-yl)-3,4-dihydro-1H-quinolin-2-one Chemical compound O=C1NC2=CC=C(C3NC4=CC=CC=C4CC3)C=C2CC1 OYNDJLFTKGHXKI-UHFFFAOYSA-N 0.000 claims 2
- SZQABMMFJHSPJZ-UHFFFAOYSA-N N,N-diethyl-4-(1,2,3,4-tetrahydroquinolin-2-yl)benzamide Chemical compound CCN(CC)C(C1=CC=C(C2NC3=CC=CC=C3CC2)C=C1)=O SZQABMMFJHSPJZ-UHFFFAOYSA-N 0.000 claims 2
- FCEZMFQOGCESQH-UHFFFAOYSA-N N-(2-hydroxyethyl)-N-methyl-2-(2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)acetamide Chemical compound CN(CCO)C(CC(C=C1CC2)=CC=C1NC2C1=CC=CC=C1)=O FCEZMFQOGCESQH-UHFFFAOYSA-N 0.000 claims 2
- YJVKYPOSNRLMRA-UHFFFAOYSA-N N-(oxetan-3-yl)-2-(2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)acetamide Chemical compound O=C(CC(C=C1CC2)=CC=C1NC2C1=CC=CC=C1)NC1COC1 YJVKYPOSNRLMRA-UHFFFAOYSA-N 0.000 claims 2
- ZXIRQZNRGNVVQL-UHFFFAOYSA-N N-cyclobutyl-2-(2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)acetamide Chemical compound O=C(CC(C=C1CC2)=CC=C1NC2C1=CC=CC=C1)NC1CCC1 ZXIRQZNRGNVVQL-UHFFFAOYSA-N 0.000 claims 2
- BYCDAZPZSZNTTQ-UHFFFAOYSA-N N-cyclopropyl-2-(2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)acetamide Chemical compound O=C(CC(C=C1CC2)=CC=C1NC2C1=CC=CC=C1)NC1CC1 BYCDAZPZSZNTTQ-UHFFFAOYSA-N 0.000 claims 2
- MADKHAMYNYKGSO-UHFFFAOYSA-N N-ethyl-4-(1,2,3,4-tetrahydroquinolin-2-yl)benzamide Chemical compound CCNC(C1=CC=C(C2NC3=CC=CC=C3CC2)C=C1)=O MADKHAMYNYKGSO-UHFFFAOYSA-N 0.000 claims 2
- NXBRFXSNKXMGGZ-UHFFFAOYSA-N N-methyl-3-(1,2,3,4-tetrahydroquinolin-2-yl)benzamide Chemical compound CNC(C1=CC(C2NC3=CC=CC=C3CC2)=CC=C1)=O NXBRFXSNKXMGGZ-UHFFFAOYSA-N 0.000 claims 2
- VIYSVBLACAABTN-UHFFFAOYSA-N N-tert-butyl-2-(2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)acetamide Chemical compound CC(C)(C)NC(CC(C=C1)=CC(CC2)=C1NC2C1=CC=CC=C1)=O VIYSVBLACAABTN-UHFFFAOYSA-N 0.000 claims 2
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- ZECJDJZLOIWCPL-UHFFFAOYSA-N [2-(1,2,3,4-tetrahydroquinolin-2-yl)phenyl]methanol Chemical compound OCC1=C(C2NC3=CC=CC=C3CC2)C=CC=C1 ZECJDJZLOIWCPL-UHFFFAOYSA-N 0.000 claims 2
- UKYCJPGPDOQCRI-UHFFFAOYSA-N [3-(1,2,3,4-tetrahydroquinolin-2-yl)phenyl]methanol Chemical compound OCC1=CC(C2NC3=CC=CC=C3CC2)=CC=C1 UKYCJPGPDOQCRI-UHFFFAOYSA-N 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- YNIBBNQBLBSDAS-UHFFFAOYSA-N morpholin-4-yl-[4-(1,2,3,4-tetrahydroquinolin-2-yl)phenyl]methanone Chemical compound O=C(C1=CC=C(C2NC3=CC=CC=C3CC2)C=C1)N1CCOCC1 YNIBBNQBLBSDAS-UHFFFAOYSA-N 0.000 claims 2
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- LRSIMNSKDKBWDG-UHFFFAOYSA-N piperidin-1-yl-[4-(1,2,3,4-tetrahydroquinolin-2-yl)phenyl]methanone Chemical compound O=C(C1=CC=C(C2NC3=CC=CC=C3CC2)C=C1)N1CCCCC1 LRSIMNSKDKBWDG-UHFFFAOYSA-N 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- GKBFIFHNRMKWIY-UHFFFAOYSA-N 2-(6-methoxypyridin-3-yl)-1,2,3,4-tetrahydroquinoline Chemical compound COC1=CC=C(C2NC3=CC=CC=C3CC2)C=N1 GKBFIFHNRMKWIY-UHFFFAOYSA-N 0.000 claims 1
- FTXIEHOUUFATFS-UHFFFAOYSA-N 3-phenyl-1,2,3,4-tetrahydroquinoline Chemical compound C1NC2=CC=CC=C2CC1C1=CC=CC=C1 FTXIEHOUUFATFS-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 1
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- 230000004806 ferroptosis Effects 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 150000003951 lactams Chemical group 0.000 claims 1
- YHAXSRWHIHSDSI-UHFFFAOYSA-N methyl 2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate Chemical compound C1CC2=CC(C(=O)OC)=CC=C2NC1C1=CC=C(OC)C=C1 YHAXSRWHIHSDSI-UHFFFAOYSA-N 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
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| US4801593A (en) | 1979-09-13 | 1989-01-31 | Burroughs Wellcome Co. | Chemotherapeutic agents |
| JP3209568B2 (ja) | 1991-04-16 | 2001-09-17 | 杏林製薬株式会社 | 新規環状アミノフェニル酢酸誘導体、その製造法及びそれらを有効成分とする免疫応答の修飾剤 |
| KR100236910B1 (ko) | 1992-12-14 | 2000-04-01 | 김영환 | 고집적 반도체 기억소자의 메모리셀어레이 제조방법 |
| DE10236910A1 (de) | 2002-08-12 | 2004-03-11 | Grünenthal GmbH | Substituierte 1,2,3,4-Tetrahydrochinolinderivate |
| EP2033959B1 (de) | 2003-12-20 | 2011-04-27 | Merck Patent GmbH | Tetrahydropyranochinolinderivate |
| DE102005027170A1 (de) | 2005-06-13 | 2006-12-14 | Merck Patent Gmbh | Substituierte Tetrahydrochinoline |
| CN1817863A (zh) | 2006-03-13 | 2006-08-16 | 中国科学院上海药物研究所 | 3－取代的1，2，3，4－四氢喹啉衍生物及其合成方法和用途 |
| CN101147737A (zh) | 2006-09-22 | 2008-03-26 | 中国科学院上海药物研究所 | 选择性雌激素受体亚型调节剂及其合成方法和医药用途 |
| SG11201506924YA (en) | 2013-03-15 | 2015-09-29 | Incyte Corp | Tricyclic heterocycles as bet protein inhibitors |
| CN104647270A (zh) | 2013-11-18 | 2015-05-27 | 张祥 | 一种新型材料安装工具 |
| WO2016075137A1 (en) * | 2014-11-10 | 2016-05-19 | Helmholtz Zentrum München - Deutsches Forschungszentrum für Gesundheit und Umwelt (GmbH) | Spiropyrazine derivatives as inhibitors of non-apoptotic regulated cell-death |
| TW201741307A (zh) | 2016-02-22 | 2017-12-01 | 艾洛斯生物製藥公司 | Ｆｘｒ調節劑及其使用方法 |
| WO2019106434A1 (en) * | 2017-12-01 | 2019-06-06 | Collaborative Medicinal Development Pty. Ltd. | Heterobicyclic aromatic derivatives for the treatment of ferroptosis-related disorders |
| BR112021017831A2 (pt) | 2019-03-11 | 2021-11-30 | Collaborative Medicinal Dev Llc | Derivados heteroaromáticos e aromáticos heterobicíclicos para o tratamento de distúrbios relacionados com ferroptose |
| CN111848675B (zh) | 2019-04-25 | 2021-09-07 | 中国科学院化学研究所 | 四氢喹啉骨架手性膦-氮配体及其制备方法和应用 |
| CN110372614B (zh) | 2019-07-03 | 2020-09-29 | 山东师范大学 | 一种四氢喹喔啉类化合物及制备方法与应用 |
| CN110464727B (zh) | 2019-09-06 | 2025-09-23 | 山东师范大学 | 3,4-二氢-2h-苯并-[1,4]恶嗪类药物或其盐在制备抑制铁死亡药物中的应用 |
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