RU2350604C2 - Производные тетрагидрохинолина, демонстрирующие защитное от вич-инфекции действие - Google Patents

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Publication number

RU2350604C2

RU2350604C2 RU2007105823/04A RU2007105823A RU2350604C2 RU 2350604 C2 RU2350604 C2 RU 2350604C2 RU 2007105823/04 A RU2007105823/04 A RU 2007105823/04A RU 2007105823 A RU2007105823 A RU 2007105823A RU 2350604 C2 RU2350604 C2 RU 2350604C2

Authority

RU

Russia

Prior art keywords

methyl

tetrahydro

benzimidazol

quinolinamine

het

Prior art date

2004-08-16

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• 208000031886 HIV Infections Diseases 0.000 title claims abstract description 14
• 208000037357 HIV infectious disease Diseases 0.000 title claims abstract description 14
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 title claims abstract description 14
• 230000001681 protective effect Effects 0.000 title description 4
• 125000000147 tetrahydroquinolinyl group Chemical class N1(CCCC2=CC=CC=C12)* 0.000 title 1
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 143
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 119
• 150000001412 amines Chemical class 0.000 claims abstract description 76
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 73
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 44
• 238000000034 method Methods 0.000 claims abstract description 43
• 238000011282 treatment Methods 0.000 claims abstract description 39
• 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 34
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 25
• 150000002367 halogens Chemical class 0.000 claims abstract description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 23
• 239000003814 drug Substances 0.000 claims abstract description 19
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 18
• 125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 18
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 18
• 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 18
• 125000005724 cycloalkenylene group Chemical group 0.000 claims abstract description 16
• 125000004450 alkenylene group Chemical group 0.000 claims abstract description 15
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 15
• 230000000694 effects Effects 0.000 claims abstract description 12
• 238000004519 manufacturing process Methods 0.000 claims abstract description 5
• 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 3
• 150000001875 compounds Chemical class 0.000 claims description 285
• -1 halogenated Chemical group 0.000 claims description 131
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 74
• 125000000304 alkynyl group Chemical group 0.000 claims description 66
• 150000003839 salts Chemical class 0.000 claims description 41
• 239000002253 acid Substances 0.000 claims description 39
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 33
• 229910052739 hydrogen Inorganic materials 0.000 claims description 31
• 150000003973 alkyl amines Chemical class 0.000 claims description 29
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
• 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 claims description 22
• 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 claims description 22
• 201000010099 disease Diseases 0.000 claims description 18
• 238000006268 reductive amination reaction Methods 0.000 claims description 17
• 150000002148 esters Chemical class 0.000 claims description 16
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
• 230000003993 interaction Effects 0.000 claims description 15
• 102000009410 Chemokine receptor Human genes 0.000 claims description 14
• 108050000299 Chemokine receptor Proteins 0.000 claims description 14
• 125000004419 alkynylene group Chemical group 0.000 claims description 14
• 125000001072 heteroaryl group Chemical group 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
• AIVVNDNIWAQWOH-UHFFFAOYSA-N n-methyl-n-[(4-piperazin-1-yl-1h-benzimidazol-2-yl)methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(NC1=CC=C2)=NC1=C2N1CCNCC1 AIVVNDNIWAQWOH-UHFFFAOYSA-N 0.000 claims description 13
• 125000006239 protecting group Chemical group 0.000 claims description 13
• 101710149870 C-C chemokine receptor type 5 Proteins 0.000 claims description 12
• 102100035875 C-C chemokine receptor type 5 Human genes 0.000 claims description 12
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
• 230000015572 biosynthetic process Effects 0.000 claims description 12
• FTIUDAIKGCFJLJ-UHFFFAOYSA-N (3-aminopyrrolidin-1-yl)-[2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-1h-benzimidazol-4-yl]methanone Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(NC1=CC=C2)=NC1=C2C(=O)N1CCC(N)C1 FTIUDAIKGCFJLJ-UHFFFAOYSA-N 0.000 claims description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 230000002265 prevention Effects 0.000 claims description 9
• NACDDZQXTMQNSA-UHFFFAOYSA-N (4-aminopiperidin-1-yl)-[2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-1h-benzimidazol-4-yl]methanone Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(NC1=CC=C2)=NC1=C2C(=O)N1CCC(N)CC1 NACDDZQXTMQNSA-UHFFFAOYSA-N 0.000 claims description 8
• RARYKEKXHDOFGV-LJQANCHMSA-N (8r)-n-methyl-n-[[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@H]1C2=NC=CC=C2CCC1)CC(NC1=CC=C2)=NC1=C2N1CCN(C)CC1 RARYKEKXHDOFGV-LJQANCHMSA-N 0.000 claims description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
• 125000003282 alkyl amino group Chemical group 0.000 claims description 8
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 7
• RARYKEKXHDOFGV-UHFFFAOYSA-N n-methyl-n-[[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(NC1=CC=C2)=NC1=C2N1CCN(C)CC1 RARYKEKXHDOFGV-UHFFFAOYSA-N 0.000 claims description 7
• DBJZTGDRXJYWAL-UHFFFAOYSA-N n-methyl-n-[[4-[4-(2-methylpropyl)piperazin-1-yl]-1h-benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(CC(C)C)CCN1C1=CC=CC2=C1N=C(CN(C)C1C3=NC=CC=C3CCC1)N2 DBJZTGDRXJYWAL-UHFFFAOYSA-N 0.000 claims description 7
• 125000004043 oxo group Chemical group O=* 0.000 claims description 7
• 229940124597 therapeutic agent Drugs 0.000 claims description 7
• JKAGHWHIEIKQQE-HXUWFJFHSA-N (8r)-n-methyl-n-[[1-methyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@H]1C2=NC=CC=C2CCC1)CC(N(C1=2)C)=NC1=CC=CC=2N1CCN(C)CC1 JKAGHWHIEIKQQE-HXUWFJFHSA-N 0.000 claims description 6
• XILRUNRCEGYBHT-QFIPXVFZSA-N (8s)-n-[[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl]-n-propan-2-yl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CC(C)N([C@@H]1C2=NC=CC=C2CCC1)CC(NC1=CC=C2)=NC1=C2N1CCN(C)CC1 XILRUNRCEGYBHT-QFIPXVFZSA-N 0.000 claims description 6
• YCEZDFREVJWARV-NRFANRHFSA-N (8s)-n-[[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl]-n-propyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CCCN([C@@H]1C2=NC=CC=C2CCC1)CC(NC1=CC=C2)=NC1=C2N1CCN(C)CC1 YCEZDFREVJWARV-NRFANRHFSA-N 0.000 claims description 6
• GJJZPHWMEXPWCE-MHZLTWQESA-N (8s)-n-benzyl-n-[[1-ethyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound N=1C2=CC=CC(N3CCN(C)CC3)=C2N(CC)C=1CN([C@@H]1C2=NC=CC=C2CCC1)CC1=CC=CC=C1 GJJZPHWMEXPWCE-MHZLTWQESA-N 0.000 claims description 6
• VQKSJFFHUQOXEV-FQEVSTJZSA-N (8s)-n-ethyl-n-[[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CCN([C@@H]1C2=NC=CC=C2CCC1)CC(NC1=CC=C2)=NC1=C2N1CCN(C)CC1 VQKSJFFHUQOXEV-FQEVSTJZSA-N 0.000 claims description 6
• UQUSGFGEARIPEG-IBGZPJMESA-N (8s)-n-methyl-n-[(1-methyl-7-piperazin-1-ylbenzimidazol-2-yl)methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(N(C1=2)C)=NC1=CC=CC=2N1CCNCC1 UQUSGFGEARIPEG-IBGZPJMESA-N 0.000 claims description 6
• JKAGHWHIEIKQQE-FQEVSTJZSA-N (8s)-n-methyl-n-[[1-methyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(N(C1=2)C)=NC1=CC=CC=2N1CCN(C)CC1 JKAGHWHIEIKQQE-FQEVSTJZSA-N 0.000 claims description 6
• QQRPHGDTDFELFZ-NRFANRHFSA-N 2-[[1-methyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]ethanol Chemical compound C1CN(C)CCN1C1=CC=CC2=C1N(C)C(CN(CCO)[C@@H]1C3=NC=CC=C3CCC1)=N2 QQRPHGDTDFELFZ-NRFANRHFSA-N 0.000 claims description 6
• FXPHCSJKYTUWQD-QFIPXVFZSA-N 3-[[1-methyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]propan-1-ol Chemical compound C1CN(C)CCN1C1=CC=CC2=C1N(C)C(CN(CCCO)[C@@H]1C3=NC=CC=C3CCC1)=N2 FXPHCSJKYTUWQD-QFIPXVFZSA-N 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• DWASOSKRUBULNA-UHFFFAOYSA-N n-(2-aminoethyl)-2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-1h-benzimidazole-4-carboxamide Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=C(C(=O)NCCN)C=CC=C2N1 DWASOSKRUBULNA-UHFFFAOYSA-N 0.000 claims description 6
• UOGDWUJAQURVRZ-UHFFFAOYSA-N n-(cyclopropylmethyl)-n-[[1-methyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(C)CCN1C1=CC=CC2=C1N(C)C(CN(CC1CC1)C1C3=NC=CC=C3CCC1)=N2 UOGDWUJAQURVRZ-UHFFFAOYSA-N 0.000 claims description 6
• CXNVDVURPCDBBQ-UHFFFAOYSA-N n-[2-(1-methylimidazol-4-yl)ethyl]-2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-1h-benzimidazole-4-carboxamide Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(NC1=CC=C2)=NC1=C2C(=O)NCCC1=CN(C)C=N1 CXNVDVURPCDBBQ-UHFFFAOYSA-N 0.000 claims description 6
• XAMZEKNCLIUYDE-UHFFFAOYSA-N n-[2-(1h-imidazol-5-yl)ethyl]-3-methyl-2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]benzimidazole-4-carboxamide Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(N(C1=2)C)=NC1=CC=CC=2C(=O)NCCC1=CNC=N1 XAMZEKNCLIUYDE-UHFFFAOYSA-N 0.000 claims description 6
• PHRYNVIBEQXSSX-UHFFFAOYSA-N n-[[1-methyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl]-n-propyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(CCC)CC(N(C1=2)C)=NC1=CC=CC=2N1CCN(C)CC1 PHRYNVIBEQXSSX-UHFFFAOYSA-N 0.000 claims description 6
• WOUDZZACVGCCAB-UHFFFAOYSA-N n-ethyl-n-[[1-methyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(CC)CC(N(C1=2)C)=NC1=CC=CC=2N1CCN(C)CC1 WOUDZZACVGCCAB-UHFFFAOYSA-N 0.000 claims description 6
• JKAGHWHIEIKQQE-UHFFFAOYSA-N n-methyl-n-[[1-methyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(N(C1=2)C)=NC1=CC=CC=2N1CCN(C)CC1 JKAGHWHIEIKQQE-UHFFFAOYSA-N 0.000 claims description 6
• XMEAWEYAOIOKAK-UHFFFAOYSA-N n-methyl-n-[[4-(4-propan-2-ylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(C(C)C)CCN1C1=CC=CC2=C1N=C(CN(C)C1C3=NC=CC=C3CCC1)N2 XMEAWEYAOIOKAK-UHFFFAOYSA-N 0.000 claims description 6
• HOTFDACOUFWRFX-UHFFFAOYSA-N n-methyl-n-[[4-(piperazin-1-ylmethyl)-1h-benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(NC1=CC=C2)=NC1=C2CN1CCNCC1 HOTFDACOUFWRFX-UHFFFAOYSA-N 0.000 claims description 6
• 238000011321 prophylaxis Methods 0.000 claims description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
• YCEZDFREVJWARV-OAQYLSRUSA-N (8r)-n-[[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl]-n-propyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CCCN([C@H]1C2=NC=CC=C2CCC1)CC(NC1=CC=C2)=NC1=C2N1CCN(C)CC1 YCEZDFREVJWARV-OAQYLSRUSA-N 0.000 claims description 5
• VQKSJFFHUQOXEV-HXUWFJFHSA-N (8r)-n-ethyl-n-[[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CCN([C@H]1C2=NC=CC=C2CCC1)CC(NC1=CC=C2)=NC1=C2N1CCN(C)CC1 VQKSJFFHUQOXEV-HXUWFJFHSA-N 0.000 claims description 5
• JEHABMXQHSEKPF-NRFANRHFSA-N (8s)-n-[[1-ethyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=12N(CC)C(CN(C)[C@@H]3C4=NC=CC=C4CCC3)=NC2=CC=CC=1N1CCN(C)CC1 JEHABMXQHSEKPF-NRFANRHFSA-N 0.000 claims description 5
• WMXSCDKRBQLQHT-QFIPXVFZSA-N (8s)-n-ethyl-n-[[1-ethyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CCN([C@@H]1C2=NC=CC=C2CCC1)CC(N(C1=2)CC)=NC1=CC=CC=2N1CCN(C)CC1 WMXSCDKRBQLQHT-QFIPXVFZSA-N 0.000 claims description 5
• RARYKEKXHDOFGV-IBGZPJMESA-N (8s)-n-methyl-n-[[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(NC1=CC=C2)=NC1=C2N1CCN(C)CC1 RARYKEKXHDOFGV-IBGZPJMESA-N 0.000 claims description 5
• ZFLVYJNHMZFULK-UHFFFAOYSA-N 2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-n-(2-piperidin-1-ylpropyl)-1h-benzimidazole-4-carboxamide Chemical compound C=1C=CC=2NC(CN(C)C3C4=NC=CC=C4CCC3)=NC=2C=1C(=O)NCC(C)N1CCCCC1 ZFLVYJNHMZFULK-UHFFFAOYSA-N 0.000 claims description 5
• PPCWMUFFNFNOTO-UHFFFAOYSA-N 2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-n-(3-pyrrolidin-1-ylpropyl)-1h-benzimidazole-4-carboxamide Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(NC1=CC=C2)=NC1=C2C(=O)NCCCN1CCCC1 PPCWMUFFNFNOTO-UHFFFAOYSA-N 0.000 claims description 5
• UZYUJPSWCDMVEI-UHFFFAOYSA-N [2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-1h-benzimidazol-4-yl]-piperazin-1-ylmethanone Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(NC1=CC=C2)=NC1=C2C(=O)N1CCNCC1 UZYUJPSWCDMVEI-UHFFFAOYSA-N 0.000 claims description 5
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• ITWVSYDHQQETDY-UHFFFAOYSA-N n,n,n'-trimethyl-n'-[2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-1h-benzimidazol-4-yl]ethane-1,2-diamine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(N1)=NC2=C1C=CC=C2N(C)CCN(C)C ITWVSYDHQQETDY-UHFFFAOYSA-N 0.000 claims description 5
• RSCQVCDQCNRTNS-UHFFFAOYSA-N n-[2-(1h-imidazol-5-yl)ethyl]-1-methyl-2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]benzimidazole-4-carboxamide Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(N(C1=CC=C2)C)=NC1=C2C(=O)NCCC1=CNC=N1 RSCQVCDQCNRTNS-UHFFFAOYSA-N 0.000 claims description 5
• VLMHVPDHRBQBED-UHFFFAOYSA-N n-[2-(1h-imidazol-5-yl)ethyl]-2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-1h-benzimidazole-4-carboxamide Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(NC1=CC=C2)=NC1=C2C(=O)NCCC1=CNC=N1 VLMHVPDHRBQBED-UHFFFAOYSA-N 0.000 claims description 5
• RNQICXXTWHOGDV-UHFFFAOYSA-N n-[2-[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]propan-2-yl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(C)CCN1C1=CC=CC2=C1N=C(C(C)(C)NC1C3=NC=CC=C3CCC1)N2 RNQICXXTWHOGDV-UHFFFAOYSA-N 0.000 claims description 5
• PQLNCSVIBGNJKT-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-1h-benzimidazole-4-carboxamide Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(N1)=NC2=C1C=CC=C2C(=O)NCCCN(C)C PQLNCSVIBGNJKT-UHFFFAOYSA-N 0.000 claims description 5
• XILRUNRCEGYBHT-UHFFFAOYSA-N n-[[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl]-n-propan-2-yl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C(C)C)CC(NC1=CC=C2)=NC1=C2N1CCN(C)CC1 XILRUNRCEGYBHT-UHFFFAOYSA-N 0.000 claims description 5
• TYTCWJIKJIONKI-QFIPXVFZSA-N (8s)-n-(cyclopropylmethyl)-n-[[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(C)CCN1C1=CC=CC2=C1N=C(CN(CC1CC1)[C@@H]1C3=NC=CC=C3CCC1)N2 TYTCWJIKJIONKI-QFIPXVFZSA-N 0.000 claims description 4
• WOUHFSTYAZRQGY-IRLDBZIGSA-N (8s)-n-[[4-[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]-1h-benzimidazol-2-yl]methyl]-n-ethyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2[C@H]1N(CC)CC1=NC2=C(N3C[C@H]4CCCN4CC3)C=CC=C2N1 WOUHFSTYAZRQGY-IRLDBZIGSA-N 0.000 claims description 4
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• HINBAFPNGJXEIX-SANMLTNESA-N (8s)-n-benzyl-n-[[1-methyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(C)CCN1C1=CC=CC2=C1N(C)C(CN(CC=1C=CC=CC=1)[C@@H]1C3=NC=CC=C3CCC1)=N2 HINBAFPNGJXEIX-SANMLTNESA-N 0.000 claims description 4
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