JP2008510006A5 - - Google Patents
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- Publication number
- JP2008510006A5 JP2008510006A5 JP2007527895A JP2007527895A JP2008510006A5 JP 2008510006 A5 JP2008510006 A5 JP 2008510006A5 JP 2007527895 A JP2007527895 A JP 2007527895A JP 2007527895 A JP2007527895 A JP 2007527895A JP 2008510006 A5 JP2008510006 A5 JP 2008510006A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- tetrahydro
- benzimidazol
- piperazinyl
- quinolinamine
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 62
- 125000000753 cycloalkyl group Chemical group 0.000 claims 62
- 125000003342 alkenyl group Chemical group 0.000 claims 48
- 125000000304 alkynyl group Chemical group 0.000 claims 48
- -1 5,6,7,8-tetrahydro-8-quinolinyl Chemical group 0.000 claims 32
- 150000001875 compounds Chemical class 0.000 claims 31
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 28
- 125000001188 haloalkyl group Chemical group 0.000 claims 27
- 150000001412 amines Chemical class 0.000 claims 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 17
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims 14
- 150000001540 azides Chemical class 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 125000004450 alkenylene group Chemical group 0.000 claims 7
- 150000003973 alkyl amines Chemical group 0.000 claims 7
- 125000002947 alkylene group Chemical group 0.000 claims 7
- 125000004419 alkynylene group Chemical group 0.000 claims 7
- 125000005724 cycloalkenylene group Chemical group 0.000 claims 7
- 125000002993 cycloalkylene group Chemical group 0.000 claims 7
- 101150008896 hetR gene Proteins 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 125000003107 substituted aryl group Chemical group 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 4
- 238000006268 reductive amination reaction Methods 0.000 claims 4
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 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 3
- 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 3
- 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 3
- 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 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- VUJPYVQEUCGIRD-CTNGQTDRSA-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-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2[C@H]1N(C)CC1=NC2=C(N3C[C@H]4CCCN4CC3)C=CC=C2N1 VUJPYVQEUCGIRD-CTNGQTDRSA-N 0.000 claims 2
- KAXGLACAYVKTCC-GGAORHGYSA-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-propyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2[C@H]1N(CCC)CC1=NC2=C(N3C[C@H]4CCCN4CC3)C=CC=C2N1 KAXGLACAYVKTCC-GGAORHGYSA-N 0.000 claims 2
- 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 2
- FFKHNWAOHAYKCR-VWLOTQADSA-N (8s)-n-benzyl-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(CC=1C=CC=CC=1)[C@@H]1C3=NC=CC=C3CCC1)N2 FFKHNWAOHAYKCR-VWLOTQADSA-N 0.000 claims 2
- WOUDZZACVGCCAB-NRFANRHFSA-N (8s)-n-ethyl-n-[[1-methyl-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)C)=NC1=CC=CC=2N1CCN(C)CC1 WOUDZZACVGCCAB-NRFANRHFSA-N 0.000 claims 2
- 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 2
- 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 2
- QQXCIIQQEYYVIU-FQEVSTJZSA-N 2-[[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]ethanol Chemical compound C1CN(C)CCN1C1=CC=CC2=C1N=C(CN(CCO)[C@@H]1C3=NC=CC=C3CCC1)N2 QQXCIIQQEYYVIU-FQEVSTJZSA-N 0.000 claims 2
- BKLAKQKYHQAMPO-NRFANRHFSA-N 3-[[4-(4-methylpiperazin-1-yl)-1h-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(CN(CCCO)[C@@H]1C3=NC=CC=C3CCC1)N2 BKLAKQKYHQAMPO-NRFANRHFSA-N 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 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 2
- KEQUDHCKFFYHDG-UHFFFAOYSA-N (2-methylpiperazin-1-yl)-[2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-1h-benzimidazol-4-yl]methanone Chemical compound CC1CNCCN1C(=O)C1=CC=CC2=C1N=C(CN(C)C1C3=NC=CC=C3CCC1)N2 KEQUDHCKFFYHDG-UHFFFAOYSA-N 0.000 claims 1
- SEIGKYUPWXPYOF-UHFFFAOYSA-N (4-methyl-1,4-diazepan-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)N1CCCN(C)CC1 SEIGKYUPWXPYOF-UHFFFAOYSA-N 0.000 claims 1
- TYTCWJIKJIONKI-JOCHJYFZSA-N (8r)-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-JOCHJYFZSA-N 0.000 claims 1
- 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 1
- 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 1
- GFKAWKPZHDXHQF-DWACAAAGSA-N (8s)-n-[(1s)-1-(4-methoxyphenyl)ethyl]-n-[[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1=CC(OC)=CC=C1[C@H](C)N([C@@H]1C2=NC=CC=C2CCC1)CC1=NC2=C(N3CCN(C)CC3)C=CC=C2N1 GFKAWKPZHDXHQF-DWACAAAGSA-N 0.000 claims 1
- PHRYNVIBEQXSSX-QFIPXVFZSA-N (8s)-n-[[1-methyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl]-n-propyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CCCN([C@@H]1C2=NC=CC=C2CCC1)CC(N(C1=2)C)=NC1=CC=CC=2N1CCN(C)CC1 PHRYNVIBEQXSSX-QFIPXVFZSA-N 0.000 claims 1
- SPAZYPFSZCWRHW-MHZLTWQESA-N (8s)-n-[[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl]-n-(2-phenylmethoxyethyl)-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(C)CCN1C1=CC=CC2=C1N=C(CN(CCOCC=1C=CC=CC=1)[C@@H]1C3=NC=CC=C3CCC1)N2 SPAZYPFSZCWRHW-MHZLTWQESA-N 0.000 claims 1
- AOSZKCJHOXNRRQ-KNKQGSTJSA-N (8s)-n-methyl-n-[[4-[(1r,5r)-7-methyl-3,7-diazabicyclo[3.3.1]nonan-3-yl]-1h-benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2[C@H]1N(C)CC(N1)=NC2=C1C=CC=C2N1C[C@]([H])(C2)CN(C)C[C@]2([H])C1 AOSZKCJHOXNRRQ-KNKQGSTJSA-N 0.000 claims 1
- PLCPGWAKLYOXGH-UHFFFAOYSA-N 1,4-diazepan-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)N1CCCNCC1 PLCPGWAKLYOXGH-UHFFFAOYSA-N 0.000 claims 1
- TUTCEJURRXOTCW-FQEVSTJZSA-N 2-[(1-methyl-7-piperazin-1-ylbenzimidazol-2-yl)methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]ethanol Chemical compound C=12N(C)C(CN(CCO)[C@@H]3C4=NC=CC=C4CCC3)=NC2=CC=CC=1N1CCNCC1 TUTCEJURRXOTCW-FQEVSTJZSA-N 0.000 claims 1
- ZYJDJJZRBPKYHA-UHFFFAOYSA-N 2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-3h-benzimidazole-5-carboxamide Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC(C(N)=O)=CC=C2N1 ZYJDJJZRBPKYHA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- KZZCKGOROMDOGS-UHFFFAOYSA-N 2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-n-(3-morpholin-4-ylpropyl)-1h-benzimidazole-4-carboxamide Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(NC1=CC=C2)=NC1=C2C(=O)NCCCN1CCOCC1 KZZCKGOROMDOGS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- BXRGVNBGSSKVQV-UHFFFAOYSA-N 2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-n-pyrrolidin-3-yl-1h-benzimidazole-4-carboxamide Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(NC1=CC=C2)=NC1=C2C(=O)NC1CCNC1 BXRGVNBGSSKVQV-UHFFFAOYSA-N 0.000 claims 1
- LKKJUYYLZICHDK-UHFFFAOYSA-N 2-amino-1-[4-[2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-1h-benzimidazol-4-yl]piperazin-1-yl]ethanone Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(NC1=CC=C2)=NC1=C2N1CCN(C(=O)CN)CC1 LKKJUYYLZICHDK-UHFFFAOYSA-N 0.000 claims 1
- FRZVZLBUYAQLLQ-NRFANRHFSA-N 3-[(1-methyl-7-piperazin-1-ylbenzimidazol-2-yl)methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]propan-1-ol Chemical compound C=12N(C)C(CN(CCCO)[C@@H]3C4=NC=CC=C4CCC3)=NC2=CC=CC=1N1CCNCC1 FRZVZLBUYAQLLQ-NRFANRHFSA-N 0.000 claims 1
- AYUHGILYDIWLTB-NBJLRHFZSA-N [(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-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(N1)=NC2=C1C=CC=C2C(=O)N1C[C@@]2([H])NC[C@]1([H])C2 AYUHGILYDIWLTB-NBJLRHFZSA-N 0.000 claims 1
- 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 1
- 239000002253 acid Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 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 1
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- CQQDKTZHTMVCMI-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-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)NCCCN1C=CN=C1 CQQDKTZHTMVCMI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- DPKLWXGZKISPJR-UHFFFAOYSA-N n-[2-(1h-imidazol-5-yl)ethyl]-n-methyl-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)N(C)CCC1=CNC=N1 DPKLWXGZKISPJR-UHFFFAOYSA-N 0.000 claims 1
- CFNWGVHJUZTQAE-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-3h-benzimidazole-5-carboxamide Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC(C(=O)NCCN(C)C)=CC=C2N1 CFNWGVHJUZTQAE-UHFFFAOYSA-N 0.000 claims 1
- NIPDTHOZOIZMEB-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-n-methyl-2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-3h-benzimidazole-5-carboxamide Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC(C(=O)N(C)CCN(C)C)=CC=C2N1 NIPDTHOZOIZMEB-UHFFFAOYSA-N 0.000 claims 1
- AZGPTXXUFQWOAI-UHFFFAOYSA-N n-[2-(methylamino)ethyl]-2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-3h-benzimidazole-5-carboxamide Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC(C(=O)NCCNC)=CC=C2N1 AZGPTXXUFQWOAI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- PCHFSEFNDXTJDN-UHFFFAOYSA-N n-[[4-(3-aminopropyl)-1h-benzimidazol-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=C(CCCN)C=CC=C2N1 PCHFSEFNDXTJDN-UHFFFAOYSA-N 0.000 claims 1
- AUJRGNBGQHHJBI-UHFFFAOYSA-N n-[[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl]-6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-amine Chemical compound C1CN(C)CCN1C1=CC=CC2=C1N=C(CNC1C3=NC=CC=C3CCCC1)N2 AUJRGNBGQHHJBI-UHFFFAOYSA-N 0.000 claims 1
- TXSSWGGJUUVKKX-UHFFFAOYSA-N n-[[4-[3-(dimethylamino)propyl]-1h-benzimidazol-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(N1)=NC2=C1C=CC=C2CCCN(C)C TXSSWGGJUUVKKX-UHFFFAOYSA-N 0.000 claims 1
- FWOUHVFETOOCEE-UHFFFAOYSA-N n-[[4-[[2-(1h-imidazol-5-yl)ethylamino]methyl]-1h-benzimidazol-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(NC1=CC=C2)=NC1=C2CNCCC1=CNC=N1 FWOUHVFETOOCEE-UHFFFAOYSA-N 0.000 claims 1
- MNOSDBUSRSZMAH-UHFFFAOYSA-N n-[[4-chloro-7-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(NC1=2)=NC1=C(Cl)C=CC=2N1CCN(C)CC1 MNOSDBUSRSZMAH-UHFFFAOYSA-N 0.000 claims 1
- JXVIGRBEAZIWFL-UHFFFAOYSA-N n-[[5-chloro-4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(NC1=CC=C2Cl)=NC1=C2N1CCN(C)CC1 JXVIGRBEAZIWFL-UHFFFAOYSA-N 0.000 claims 1
- PEEKKEHJKFLYMX-RXBHZZDJSA-N n-methyl-n-[(1r)-1-[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]-2-phenylmethoxyethyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C([C@H](N(C)C1C2=NC=CC=C2CCC1)C=1NC2=CC=CC(=C2N=1)N1CCN(C)CC1)OCC1=CC=CC=C1 PEEKKEHJKFLYMX-RXBHZZDJSA-N 0.000 claims 1
- SCLHDSJQXSNULJ-DIAVIDTQSA-N n-methyl-n-[(1r)-1-[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]ethyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1=CC=C2NC([C@H](N(C)C3C4=NC=CC=C4CCC3)C)=NC2=C1N1CCN(C)CC1 SCLHDSJQXSNULJ-DIAVIDTQSA-N 0.000 claims 1
- PEEKKEHJKFLYMX-SVNIRARHSA-N n-methyl-n-[(1s)-1-[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]-2-phenylmethoxyethyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C([C@@H](N(C)C1C2=NC=CC=C2CCC1)C=1NC2=CC=CC(=C2N=1)N1CCN(C)CC1)OCC1=CC=CC=C1 PEEKKEHJKFLYMX-SVNIRARHSA-N 0.000 claims 1
- 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 1
- KKMUCSXJJSSXRO-UHFFFAOYSA-N n-methyl-n-[2-(methylamino)ethyl]-2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-3h-benzimidazole-5-carboxamide Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC(C(=O)N(C)CCNC)=CC=C2N1 KKMUCSXJJSSXRO-UHFFFAOYSA-N 0.000 claims 1
- ADLDLGPOAXVPAX-UHFFFAOYSA-N n-methyl-n-[2-[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]propan-2-yl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)C(C)(C)C(NC1=CC=C2)=NC1=C2N1CCN(C)CC1 ADLDLGPOAXVPAX-UHFFFAOYSA-N 0.000 claims 1
- MKNFQYOGYHJLFR-UHFFFAOYSA-N n-methyl-n-[[4-(3-piperidin-1-ylpropyl)-1h-benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(NC1=CC=C2)=NC1=C2CCCN1CCCCC1 MKNFQYOGYHJLFR-UHFFFAOYSA-N 0.000 claims 1
- JFCUMHNRFWTSSD-UHFFFAOYSA-N n-methyl-n-[[4-(3-pyrrolidin-1-ylpropyl)-1h-benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(NC1=CC=C2)=NC1=C2CCCN1CCCC1 JFCUMHNRFWTSSD-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- PLEVUJATIJXXQN-UHFFFAOYSA-N n-methyl-n-[[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl]-6,7-dihydro-5h-cyclopenta[b]pyridin-7-amine Chemical compound C1CC2=CC=CN=C2C1N(C)CC(NC1=CC=C2)=NC1=C2N1CCN(C)CC1 PLEVUJATIJXXQN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- AOYUFWJGGKRAOW-UHFFFAOYSA-N n-propan-2-yl-n-[[4-(4-propan-2-ylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C(C)C)CC(NC1=CC=C2)=NC1=C2N1CCN(C(C)C)CC1 AOYUFWJGGKRAOW-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
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| WO2006110683A1 (en) * | 2005-04-11 | 2006-10-19 | Abbott Laboratories | 2-substituted-1h-benzimidazole-4-carboxamides are parp inhibitors |
| WO2007049771A1 (ja) | 2005-10-28 | 2007-05-03 | Ono Pharmaceutical Co., Ltd. | 塩基性基を含有する化合物およびその用途 |
| WO2007058322A1 (ja) | 2005-11-18 | 2007-05-24 | Ono Pharmaceutical Co., Ltd. | 塩基性基を含有する化合物およびその用途 |
| US8618122B2 (en) | 2006-05-16 | 2013-12-31 | Ono Pharmaceutical Co., Ltd. | Compound having acidic group which may be protected, and use thereof |
| EP2055705A4 (en) | 2006-07-31 | 2014-08-20 | Ono Pharmaceutical Co | COMPOUND WITH A CYCLIC GROUP BOUND BY A SPIRO BINDING THEREOF AND APPLY THEREOF |
| GB0702695D0 (en) * | 2007-02-12 | 2007-03-21 | Ark Therapeutics Ltd | Production of vectors |
| CL2008002242A1 (es) * | 2007-07-31 | 2009-08-21 | Bayer Cropscience Ag | Compuestos derivados de n-cicloalquil-n-carboxamida, tiocarboxamida, biciclicas o derivados de carboximidamida n-sustituida; composicion fungicida; y metodo para controlar los hongos fitopatogenos de los cultivos. |
| TW201035088A (en) | 2009-02-27 | 2010-10-01 | Supergen Inc | Cyclopentathiophene/cyclohexathiophene DNA methyltransferase inhibitors |
| JP5541454B2 (ja) * | 2009-09-16 | 2014-07-09 | Ｊｓｒ株式会社 | 液晶配向剤および液晶表示素子 |
| JP5712524B2 (ja) * | 2009-10-28 | 2015-05-07 | Jsr株式会社 | 液晶配向剤および液晶表示素子 |
| MA34591B1 (fr) | 2010-10-06 | 2013-10-02 | Glaxosmithkline Llc | Dérivés de benzimidazole utilisés comme inhibiteurs de pi3 kinase |
| CN102675305B (zh) * | 2011-03-08 | 2014-11-12 | 中国科学院上海药物研究所 | 一类咪唑并吡啶类化合物及其制备方法和用途 |
| CN103570683B (zh) * | 2012-07-30 | 2018-04-17 | 中国科学院上海药物研究所 | 多取代胺类化合物及其制备方法和用途 |
| CA3008272A1 (en) | 2015-12-14 | 2017-06-22 | X4 Pharmaceuticals, Inc. | Methods for treating cancer |
| CA3008279A1 (en) | 2015-12-14 | 2017-06-22 | X4 Pharmaceuticals, Inc. | Methods for treating cancer |
| EP3393468B1 (en) | 2015-12-22 | 2022-09-14 | X4 Pharmaceuticals, Inc. | Methods for treating immunodeficiency disease |
| JP2019510785A (ja) | 2016-04-08 | 2019-04-18 | エックス４ ファーマシューティカルズ， インコーポレイテッド | 癌を処置する方法 |
| CA3027498A1 (en) | 2016-06-21 | 2017-12-28 | X4 Pharmaceuticals, Inc. | Cxcr4 inhibitors and uses thereof |
| US10988465B2 (en) | 2016-06-21 | 2021-04-27 | X4 Pharmaceuticals, Inc. | CXCR4 inhibitors and uses thereof |
| WO2017223243A1 (en) | 2016-06-21 | 2017-12-28 | X4 Pharmaceuticals, Inc. | Cxcr4 inhibitors and uses thereof |
| WO2018156595A1 (en) | 2017-02-21 | 2018-08-30 | Emory University | Chemokine cxcr4 receptor modulators and uses related thereto |
| US11396501B2 (en) * | 2017-09-25 | 2022-07-26 | Cgenetech (Suzhou, China) Co., Ltd. | Heteroaryl compounds as CXCR4 inhibitors, composition and method using the same |
| KR102678977B1 (ko) * | 2017-09-25 | 2024-06-28 | 씨젠테크 (쑤저우, 차이나) 컴퍼니 리미티드 | Cxcr4 저해제로서 헤테로아릴 화합물, 그 조성물 및 이용 방법 |
| US11649235B2 (en) | 2018-03-19 | 2023-05-16 | Emory University | Pan-tropic entry inhibitors |
| US10548889B1 (en) | 2018-08-31 | 2020-02-04 | X4 Pharmaceuticals, Inc. | Compositions of CXCR4 inhibitors and methods of preparation and use |
| EP4117662A4 (en) | 2020-03-10 | 2024-04-03 | X4 Pharmaceuticals, Inc. | METHODS OF TREATING NEUTROPENIA |
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| EP1317445B1 (en) * | 2000-09-15 | 2009-03-11 | Anormed Inc. | Chemokine receptor binding heterocyclic compounds |
| BR0113932A (pt) * | 2000-09-15 | 2003-06-24 | Anormed Inc | Compostos heterocìclicos que se ligam ao receptor da quimiocina |
| JP2004512336A (ja) * | 2000-09-15 | 2004-04-22 | アノーメッド インコーポレイティド | ケモカインレセプター結合複素環式化合物 |
| SG126006A1 (en) * | 2000-09-15 | 2006-10-30 | Anormed Inc | Chemokine receptor binding heterocyclic compounds |
| CN1596255A (zh) * | 2001-12-21 | 2005-03-16 | 阿诺麦德股份有限公司 | 具有强效的与趋化因子受体结合的杂环化合物 |
| RU2006136381A (ru) * | 2004-03-15 | 2008-04-27 | Анормед, Инк. (Ca) | Способ получения антагониста cxcr4 |
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2005
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- 2005-08-12 AU AU2005277638A patent/AU2005277638A1/en not_active Abandoned
- 2005-08-12 CN CNA2005800351651A patent/CN101039672A/zh active Pending
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- 2005-08-12 RU RU2007105823/04A patent/RU2350604C2/ru not_active IP Right Cessation
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- 2005-08-12 TW TW094127423A patent/TW200619217A/zh unknown
- 2005-08-12 PE PE2005000940A patent/PE20060646A1/es not_active Application Discontinuation
- 2005-08-12 BR BRPI0514438-8A patent/BRPI0514438A/pt not_active IP Right Cessation
- 2005-08-12 MX MX2007001958A patent/MX2007001958A/es not_active Application Discontinuation
- 2005-08-12 US US11/573,729 patent/US20080045537A1/en not_active Abandoned
- 2005-08-12 KR KR1020077005000A patent/KR20070042568A/ko not_active Withdrawn
- 2005-08-12 EP EP05786708A patent/EP1789045A2/en not_active Withdrawn
- 2005-08-12 WO PCT/US2005/028811 patent/WO2006023400A2/en not_active Ceased
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2007
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- 2007-02-13 ZA ZA200701282A patent/ZA200701282B/xx unknown
- 2007-02-21 MA MA29700A patent/MA28814B1/fr unknown
- 2007-03-01 NO NO20071161A patent/NO20071161L/no not_active Application Discontinuation
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