JP2008508357A5 - - Google Patents
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- Publication number
- JP2008508357A5 JP2008508357A5 JP2007524853A JP2007524853A JP2008508357A5 JP 2008508357 A5 JP2008508357 A5 JP 2008508357A5 JP 2007524853 A JP2007524853 A JP 2007524853A JP 2007524853 A JP2007524853 A JP 2007524853A JP 2008508357 A5 JP2008508357 A5 JP 2008508357A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- tetrahydro
- benzimidazol
- quinolinamine
- piperidinyl
- 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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- 150000001875 compounds Chemical class 0.000 claims description 52
- 125000003342 alkenyl group Chemical group 0.000 claims description 32
- 125000000304 alkynyl group Chemical group 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 10
- -1 2-{[methyl (5,6,7,8-tetrahydro-8-quinolinyl) amino] methyl} -1H-benzimidazol-1-yl Chemical group 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims 38
- 150000003973 alkyl amines Chemical class 0.000 claims 14
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 14
- 125000001188 haloalkyl group Chemical group 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 150000001540 azides Chemical class 0.000 claims 8
- 125000004450 alkenylene group Chemical group 0.000 claims 7
- 125000002947 alkylene group Chemical group 0.000 claims 7
- 125000004419 alkynylene group Chemical group 0.000 claims 7
- 125000003118 aryl 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
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 125000002883 imidazolyl group Chemical group 0.000 claims 7
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- VETGEHMWKIZMPG-UHFFFAOYSA-N n-methyl-n-[[1-[(1-methylpiperidin-3-yl)methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CC1CCCN(C)C1 VETGEHMWKIZMPG-UHFFFAOYSA-N 0.000 claims 5
- QSKQVYGGIODIIN-BWKNWUBXSA-N (8s)-n-methyl-n-[[1-[[(3r)-1-propan-2-ylpiperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1N(C(C)C)CCC[C@H]1CN1C2=CC=CC=C2N=C1CN(C)[C@@H]1C2=NC=CC=C2CCC1 QSKQVYGGIODIIN-BWKNWUBXSA-N 0.000 claims 4
- SUVTXSXXZWCMHL-NVQXNPDNSA-N (8s)-n-methyl-n-[[1-[[(3s)-1-(2-methylpropyl)piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1N(CC(C)C)CCC[C@@H]1CN1C2=CC=CC=C2N=C1CN(C)[C@@H]1C2=NC=CC=C2CCC1 SUVTXSXXZWCMHL-NVQXNPDNSA-N 0.000 claims 4
- VETGEHMWKIZMPG-CVDCTZTESA-N (8s)-n-methyl-n-[[1-[[(3s)-1-methylpiperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC1=NC2=CC=CC=C2N1C[C@H]1CCCN(C)C1 VETGEHMWKIZMPG-CVDCTZTESA-N 0.000 claims 4
- ASCHSOKJVZUWMP-UHFFFAOYSA-N n-[[1-(3-aminopropyl)benzimidazol-2-yl]methyl]-n-ethyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(CC)CC1=NC2=CC=CC=C2N1CCCN ASCHSOKJVZUWMP-UHFFFAOYSA-N 0.000 claims 4
- JEPDGRCNPREMJT-UHFFFAOYSA-N n-[[1-[3-(dimethylamino)propyl]benzimidazol-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1=CC=C2N(CCCN(C)C)C(CN(C)C3C4=NC=CC=C4CCC3)=NC2=C1 JEPDGRCNPREMJT-UHFFFAOYSA-N 0.000 claims 4
- IBMXMPNDZLRVME-UHFFFAOYSA-N n-methyl-n-[[1-[(1-methylazetidin-3-yl)methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CC1CN(C)C1 IBMXMPNDZLRVME-UHFFFAOYSA-N 0.000 claims 4
- NTSBJKADBVYMSM-UHFFFAOYSA-N n-methyl-n-[[1-[(1-methylpyrrolidin-3-yl)methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CC1CCN(C)C1 NTSBJKADBVYMSM-UHFFFAOYSA-N 0.000 claims 4
- MFZFCJAAAVWRCZ-OFVILXPXSA-N (8s)-n-[[1-[[(3s)-1-methylpiperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-n-propyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CCCN([C@@H]1C2=NC=CC=C2CCC1)CC1=NC2=CC=CC=C2N1C[C@H]1CCCN(C)C1 MFZFCJAAAVWRCZ-OFVILXPXSA-N 0.000 claims 3
- OVVVPNSGDFVCAW-HOFKKMOUSA-N (8s)-n-[[1-[[(3s)-1-propan-2-ylpiperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-n-propyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CCCN([C@@H]1C2=NC=CC=C2CCC1)CC1=NC2=CC=CC=C2N1C[C@H]1CCCN(C(C)C)C1 OVVVPNSGDFVCAW-HOFKKMOUSA-N 0.000 claims 3
- VETGEHMWKIZMPG-XXBNENTESA-N (8s)-n-methyl-n-[[1-[[(3r)-1-methylpiperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC1=NC2=CC=CC=C2N1C[C@@H]1CCCN(C)C1 VETGEHMWKIZMPG-XXBNENTESA-N 0.000 claims 3
- XHRXIYNWBWPAAC-GCJKJVERSA-N (8s)-n-methyl-n-[[1-[[(3r)-piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC1=NC2=CC=CC=C2N1C[C@@H]1CCCNC1 XHRXIYNWBWPAAC-GCJKJVERSA-N 0.000 claims 3
- GHZOBXUUQBAKHP-HOFKKMOUSA-N (8s)-n-methyl-n-[[1-[[(3s)-1-(3-methylbutyl)piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1N(CCC(C)C)CCC[C@@H]1CN1C2=CC=CC=C2N=C1CN(C)[C@@H]1C2=NC=CC=C2CCC1 GHZOBXUUQBAKHP-HOFKKMOUSA-N 0.000 claims 3
- QSKQVYGGIODIIN-OFVILXPXSA-N (8s)-n-methyl-n-[[1-[[(3s)-1-propan-2-ylpiperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1N(C(C)C)CCC[C@@H]1CN1C2=CC=CC=C2N=C1CN(C)[C@@H]1C2=NC=CC=C2CCC1 QSKQVYGGIODIIN-OFVILXPXSA-N 0.000 claims 3
- XHRXIYNWBWPAAC-AVRDEDQJSA-N (8s)-n-methyl-n-[[1-[[(3s)-piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC1=NC2=CC=CC=C2N1C[C@H]1CCCNC1 XHRXIYNWBWPAAC-AVRDEDQJSA-N 0.000 claims 3
- OGKYHMHLZSDZND-RDPSFJRHSA-N 2-[(3s)-3-[[2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]benzimidazol-1-yl]methyl]piperidin-1-yl]ethanol Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC1=NC2=CC=CC=C2N1C[C@H]1CCCN(CCO)C1 OGKYHMHLZSDZND-RDPSFJRHSA-N 0.000 claims 3
- JSIVRGPWVYZZRY-RDPSFJRHSA-N 2-[[1-[[(3s)-1-methylpiperidin-3-yl]methyl]benzimidazol-2-yl]methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]ethanol Chemical compound C1N(C)CCC[C@@H]1CN1C2=CC=CC=C2N=C1CN(CCO)[C@@H]1C2=NC=CC=C2CCC1 JSIVRGPWVYZZRY-RDPSFJRHSA-N 0.000 claims 3
- USAIXVIEVCGFRQ-NVQXNPDNSA-N 2-[[1-[[(3s)-1-propan-2-ylpiperidin-3-yl]methyl]benzimidazol-2-yl]methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]ethanol Chemical compound C1N(C(C)C)CCC[C@@H]1CN1C2=CC=CC=C2N=C1CN(CCO)[C@@H]1C2=NC=CC=C2CCC1 USAIXVIEVCGFRQ-NVQXNPDNSA-N 0.000 claims 3
- ZGXWKJJTZYBTPX-OFVILXPXSA-N 3-[(3s)-3-[[2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]benzimidazol-1-yl]methyl]piperidin-1-yl]propan-1-ol Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC1=NC2=CC=CC=C2N1C[C@H]1CCCN(CCCO)C1 ZGXWKJJTZYBTPX-OFVILXPXSA-N 0.000 claims 3
- PXSYBAMOAXOVKV-OFVILXPXSA-N 3-[[1-[[(3s)-1-methylpiperidin-3-yl]methyl]benzimidazol-2-yl]methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]propan-1-ol Chemical compound C1N(C)CCC[C@@H]1CN1C2=CC=CC=C2N=C1CN(CCCO)[C@@H]1C2=NC=CC=C2CCC1 PXSYBAMOAXOVKV-OFVILXPXSA-N 0.000 claims 3
- HNPRTVLVYBDBAL-HOFKKMOUSA-N 3-[[1-[[(3s)-1-propan-2-ylpiperidin-3-yl]methyl]benzimidazol-2-yl]methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]propan-1-ol Chemical compound C1N(C(C)C)CCC[C@@H]1CN1C2=CC=CC=C2N=C1CN(CCCO)[C@@H]1C2=NC=CC=C2CCC1 HNPRTVLVYBDBAL-HOFKKMOUSA-N 0.000 claims 3
- HEPWOFBXMDSUEO-UHFFFAOYSA-N n-[[1-(3-aminopropyl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1=CC=C2N(CCCN)C(CNC3C4=NC=CC=C4CCC3)=NC2=C1 HEPWOFBXMDSUEO-UHFFFAOYSA-N 0.000 claims 3
- FFROZRURSWKTSQ-UHFFFAOYSA-N n-methyl-n-[[1-(1-methylpiperidin-4-yl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1C1CCN(C)CC1 FFROZRURSWKTSQ-UHFFFAOYSA-N 0.000 claims 3
- SIQJINIEOSWWSC-UHFFFAOYSA-N n-methyl-n-[[1-(piperidin-4-ylmethyl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CC1CCNCC1 SIQJINIEOSWWSC-UHFFFAOYSA-N 0.000 claims 3
- 238000006268 reductive amination reaction Methods 0.000 claims 3
- MSEIVERZUJBQCE-AVRDEDQJSA-N (3r)-3-[[2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]benzimidazol-1-yl]methyl]piperidine-1-carboximidamide Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC1=NC2=CC=CC=C2N1C[C@H]1CCCN(C(N)=N)C1 MSEIVERZUJBQCE-AVRDEDQJSA-N 0.000 claims 2
- CPNLVENHHDENTG-CVDCTZTESA-N (3r)-n'-cyano-3-[[2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]benzimidazol-1-yl]methyl]piperidine-1-carboximidamide Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC1=NC2=CC=CC=C2N1C[C@H]1CCCN(C(N)=NC#N)C1 CPNLVENHHDENTG-CVDCTZTESA-N 0.000 claims 2
- QSKQVYGGIODIIN-PXDATVDWSA-N (8r)-n-methyl-n-[[1-[[(3r)-1-propan-2-ylpiperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1N(C(C)C)CCC[C@H]1CN1C2=CC=CC=C2N=C1CN(C)[C@H]1C2=NC=CC=C2CCC1 QSKQVYGGIODIIN-PXDATVDWSA-N 0.000 claims 2
- GHZOBXUUQBAKHP-WNCULLNHSA-N (8r)-n-methyl-n-[[1-[[(3s)-1-(3-methylbutyl)piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1N(CCC(C)C)CCC[C@@H]1CN1C2=CC=CC=C2N=C1CN(C)[C@H]1C2=NC=CC=C2CCC1 GHZOBXUUQBAKHP-WNCULLNHSA-N 0.000 claims 2
- QSKQVYGGIODIIN-SQJMNOBHSA-N (8r)-n-methyl-n-[[1-[[(3s)-1-propan-2-ylpiperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1N(C(C)C)CCC[C@@H]1CN1C2=CC=CC=C2N=C1CN(C)[C@H]1C2=NC=CC=C2CCC1 QSKQVYGGIODIIN-SQJMNOBHSA-N 0.000 claims 2
- BTACNCKTZXBULU-CUBQBAPOSA-N (8s)-n-(2-methylpropyl)-n-[[1-[[(3s)-1-propan-2-ylpiperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CC(C)CN([C@@H]1C2=NC=CC=C2CCC1)CC1=NC2=CC=CC=C2N1C[C@H]1CCCN(C(C)C)C1 BTACNCKTZXBULU-CUBQBAPOSA-N 0.000 claims 2
- UPBCAKKETXMWBJ-IBGZPJMESA-N (8s)-n-[[1-(3-aminopropyl)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=CC=CC=C2N1CCCN UPBCAKKETXMWBJ-IBGZPJMESA-N 0.000 claims 2
- CGSWUZHHBXFQBH-OFVILXPXSA-N (8s)-n-[[1-[[(3s)-1-(1h-imidazol-2-ylmethyl)piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C([C@@H](C1)CN2C3=CC=CC=C3N=C2CN(C)[C@@H]2C3=NC=CC=C3CCC2)CCN1CC1=NC=CN1 CGSWUZHHBXFQBH-OFVILXPXSA-N 0.000 claims 2
- ITBGCVICESLOAL-NVQXNPDNSA-N (8s)-n-[[1-[[(3s)-1-[2-(dimethylamino)ethyl]piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1N(CCN(C)C)CCC[C@@H]1CN1C2=CC=CC=C2N=C1CN(C)[C@@H]1C2=NC=CC=C2CCC1 ITBGCVICESLOAL-NVQXNPDNSA-N 0.000 claims 2
- QIDLXLXPSJTZEG-CUBQBAPOSA-N (8s)-n-[[1-[[(3s)-1-[3-(dimethylamino)-2,2-dimethylpropyl]piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1N(CC(C)(C)CN(C)C)CCC[C@@H]1CN1C2=CC=CC=C2N=C1CN(C)[C@@H]1C2=NC=CC=C2CCC1 QIDLXLXPSJTZEG-CUBQBAPOSA-N 0.000 claims 2
- PTEDXWWFEGUZEY-SVEHJYQDSA-N (8s)-n-[[1-[[(3s)-1-benzylpiperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C([C@@H](C1)CN2C3=CC=CC=C3N=C2CN(C)[C@@H]2C3=NC=CC=C3CCC2)CCN1CC1=CC=CC=C1 PTEDXWWFEGUZEY-SVEHJYQDSA-N 0.000 claims 2
- GHZOBXUUQBAKHP-KCWPFWIISA-N (8s)-n-methyl-n-[[1-[[(3r)-1-(3-methylbutyl)piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1N(CCC(C)C)CCC[C@H]1CN1C2=CC=CC=C2N=C1CN(C)[C@@H]1C2=NC=CC=C2CCC1 GHZOBXUUQBAKHP-KCWPFWIISA-N 0.000 claims 2
- KNNLCWNQAVHYHR-FIPFOOKPSA-N (8s)-n-methyl-n-[[1-[[(3s)-1-(pyridin-2-ylmethyl)piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C([C@@H](C1)CN2C3=CC=CC=C3N=C2CN(C)[C@@H]2C3=NC=CC=C3CCC2)CCN1CC1=CC=CC=N1 KNNLCWNQAVHYHR-FIPFOOKPSA-N 0.000 claims 2
- AZXYEYLEAPSWTK-CUBQBAPOSA-N (8s)-n-methyl-n-[[1-[[(3s)-1-(pyridin-3-ylmethyl)piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C([C@@H](C1)CN2C3=CC=CC=C3N=C2CN(C)[C@@H]2C3=NC=CC=C3CCC2)CCN1CC1=CC=CN=C1 AZXYEYLEAPSWTK-CUBQBAPOSA-N 0.000 claims 2
- KSHLOXFXDIORRL-CUBQBAPOSA-N (8s)-n-methyl-n-[[1-[[(3s)-1-(pyridin-4-ylmethyl)piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C([C@@H](C1)CN2C3=CC=CC=C3N=C2CN(C)[C@@H]2C3=NC=CC=C3CCC2)CCN1CC1=CC=NC=C1 KSHLOXFXDIORRL-CUBQBAPOSA-N 0.000 claims 2
- CMSCMGVPSNOUIM-CUNXSJBXSA-N (8s)-n-methyl-n-[[1-[[(3s)-1-(thiophen-2-ylmethyl)piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C([C@@H](C1)CN2C3=CC=CC=C3N=C2CN(C)[C@@H]2C3=NC=CC=C3CCC2)CCN1CC1=CC=CS1 CMSCMGVPSNOUIM-CUNXSJBXSA-N 0.000 claims 2
- ICASOSHOAZDLCQ-CKOJHNACSA-N (8s)-n-methyl-n-[[1-[[(3s)-1-[[(2r)-1-methylpyrrolidin-2-yl]methyl]piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C([C@@H](C1)CN2C3=CC=CC=C3N=C2CN(C)[C@@H]2C3=NC=CC=C3CCC2)CCN1C[C@H]1CCCN1C ICASOSHOAZDLCQ-CKOJHNACSA-N 0.000 claims 2
- ICASOSHOAZDLCQ-AGJHTDJMSA-N (8s)-n-methyl-n-[[1-[[(3s)-1-[[(2s)-1-methylpyrrolidin-2-yl]methyl]piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C([C@@H](C1)CN2C3=CC=CC=C3N=C2CN(C)[C@@H]2C3=NC=CC=C3CCC2)CCN1C[C@@H]1CCCN1C ICASOSHOAZDLCQ-AGJHTDJMSA-N 0.000 claims 2
- RYNSAIDPKSCSKJ-XXJPWZBZSA-N (8s)-n-methyl-n-[[1-[[(3s)-1-[[(2s)-1-propan-2-ylpyrrolidin-2-yl]methyl]piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CC(C)N1CCC[C@H]1CN1C[C@@H](CN2C3=CC=CC=C3N=C2CN(C)[C@@H]2C3=NC=CC=C3CCC2)CCC1 RYNSAIDPKSCSKJ-XXJPWZBZSA-N 0.000 claims 2
- LILSBXJJIIFDGR-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinolin-8-amine Chemical compound C1CCNC2=C1C=CC=C2N LILSBXJJIIFDGR-UHFFFAOYSA-N 0.000 claims 2
- RJUSPAJEXRXMFD-UHFFFAOYSA-N 2-[2,2-dimethyl-3-[2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]benzimidazol-1-yl]propyl]guanidine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CC(C)(C)CNC(N)=N RJUSPAJEXRXMFD-UHFFFAOYSA-N 0.000 claims 2
- PTJSFJFYRHYIAG-UHFFFAOYSA-N 2-[2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]benzimidazol-1-yl]-n-(pyridin-3-ylmethyl)acetamide Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CC(=O)NCC1=CC=CN=C1 PTJSFJFYRHYIAG-UHFFFAOYSA-N 0.000 claims 2
- XVBHJNYVOUOSQU-UHFFFAOYSA-N 2-[3-[2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]benzimidazol-1-yl]propyl]guanidine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CCCN=C(N)N XVBHJNYVOUOSQU-UHFFFAOYSA-N 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- AMJRGYWDPGQUFD-SREVYHEPSA-N n-[[1-[(z)-4-(dimethylamino)but-2-enyl]benzimidazol-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1=CC=C2N(C\C=C/CN(C)C)C(CN(C)C3C4=NC=CC=C4CCC3)=NC2=C1 AMJRGYWDPGQUFD-SREVYHEPSA-N 0.000 claims 2
- WGGZMASUPJMNOJ-UHFFFAOYSA-N n-[[1-[3-(dimethylamino)-2,2-dimethylpropyl]benzimidazol-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1=CC=C2N(CC(C)(C)CN(C)C)C(CN(C)C3C4=NC=CC=C4CCC3)=NC2=C1 WGGZMASUPJMNOJ-UHFFFAOYSA-N 0.000 claims 2
- DYMRYCZRMAHYKE-UHFFFAOYSA-N n-diazonitramide Chemical compound [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 claims 2
- CEZDJMFFDIZREC-UHFFFAOYSA-N n-methyl-n-[[1-(2-piperidin-2-ylethyl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CCC1CCCCN1 CEZDJMFFDIZREC-UHFFFAOYSA-N 0.000 claims 2
- LJLXFECAEZYHOF-UHFFFAOYSA-N n-methyl-n-[[1-(pyrrolidin-3-ylmethyl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CC1CCNC1 LJLXFECAEZYHOF-UHFFFAOYSA-N 0.000 claims 2
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- MSEIVERZUJBQCE-PGRDOPGGSA-N (3r)-3-[[2-[[methyl-[(8r)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]benzimidazol-1-yl]methyl]piperidine-1-carboximidamide Chemical compound CN([C@H]1C2=NC=CC=C2CCC1)CC1=NC2=CC=CC=C2N1C[C@H]1CCCN(C(N)=N)C1 MSEIVERZUJBQCE-PGRDOPGGSA-N 0.000 claims 1
- NTXFYIUIGQCZRF-OFVILXPXSA-N (3r)-n'-cyano-n,n-dimethyl-3-[[2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]benzimidazol-1-yl]methyl]piperidine-1-carboximidamide Chemical compound C1N(C(=NC#N)N(C)C)CCC[C@@H]1CN1C2=CC=CC=C2N=C1CN(C)[C@@H]1C2=NC=CC=C2CCC1 NTXFYIUIGQCZRF-OFVILXPXSA-N 0.000 claims 1
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- JRXTWPLHXHGEEV-OFVILXPXSA-N (8s)-n-methyl-n-[[1-[[(3s)-1-(1,3-thiazol-2-ylmethyl)piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C([C@@H](C1)CN2C3=CC=CC=C3N=C2CN(C)[C@@H]2C3=NC=CC=C3CCC2)CCN1CC1=NC=CS1 JRXTWPLHXHGEEV-OFVILXPXSA-N 0.000 claims 1
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| EP2657235A1 (en) | 2005-10-28 | 2013-10-30 | Ono Pharmaceutical Co., Ltd. | Compound containing basic group and use thereof |
| US8168783B2 (en) | 2005-11-18 | 2012-05-01 | Ono Pharmaceutical Co., Ltd. | Chemokine receptor antagonists and use thereof |
| WO2007132846A1 (ja) | 2006-05-16 | 2007-11-22 | Ono Pharmaceutical Co., Ltd. | 保護されていてもよい酸性基を含有する化合物およびその用途 |
| US20090325992A1 (en) | 2006-07-31 | 2009-12-31 | Ono Pharmaceutical Co., Ltd. | Compound having cyclic group bound thereto through spiro binding and use thereof |
| WO2009126675A1 (en) * | 2008-04-09 | 2009-10-15 | Boehringer Ingelheim International Gmbh | 2-sulfonylamino-4-heteroaryl butyramide antagonists of ccr10 |
| EP2646430B1 (en) * | 2010-12-03 | 2016-09-21 | Emory University | Chemokine cxcr4 receptor modulators and uses related thereto |
| BR112013014914B8 (pt) | 2010-12-16 | 2020-08-04 | Hoffmann La Roche | composto, composição farmacêutica e uso de um composto |
| WO2012107465A1 (en) * | 2011-02-09 | 2012-08-16 | F. Hoffmann-La Roche Ag | Heterocyclic compounds as pi3 kinase inhibitors |
| US10450293B2 (en) | 2014-05-16 | 2019-10-22 | Emory University | Chemokine CXCR4 and CCR5 receptor modulators and uses related thereto |
| CN104447567B (zh) * | 2014-11-02 | 2016-06-29 | 湖南华腾制药有限公司 | 一种1位取代苯并咪唑衍生物的制备方法 |
| JP6958820B2 (ja) | 2015-12-14 | 2021-11-02 | 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 | がんを処置する方法 |
| EP3389634B1 (en) | 2015-12-14 | 2021-10-06 | X4 Pharmaceuticals, Inc. | Methods for treating cancer |
| JP7055380B2 (ja) | 2015-12-22 | 2022-04-18 | 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 | 免疫不全疾患を処置するための方法 |
| WO2017177230A1 (en) | 2016-04-08 | 2017-10-12 | X4 Pharmaceuticals, Inc. | Methods for treating cancer |
| US11433048B2 (en) | 2016-06-16 | 2022-09-06 | Centre National De La Recherche Scientifique | CXCR4 receptor-binding compounds useful for increasing interferon level |
| CA3027500A1 (en) | 2016-06-21 | 2017-12-28 | X4 Pharmaceuticals, Inc. | Cxcr4 inhibitors and uses thereof |
| EP3808748A1 (en) | 2016-06-21 | 2021-04-21 | X4 Pharmaceuticals, Inc. | Substituted piperidines as cxcr4-inhibitors |
| CN109640988A (zh) | 2016-06-21 | 2019-04-16 | X4 制药有限公司 | Cxcr4抑制剂及其用途 |
| EP3585387A4 (en) | 2017-02-21 | 2020-08-12 | Emory University | CHEMIOKIN CXCR4 RECEIVER MODULATORS AND THEIR USES |
| WO2019183133A1 (en) | 2018-03-19 | 2019-09-26 | Emory University | Pan-Tropic Entry Inhibitors |
| CN108373466B (zh) * | 2018-04-16 | 2020-04-10 | 宏冠生物药业有限公司 | 一种达比加群酯的制备方法 |
| US10548889B1 (en) | 2018-08-31 | 2020-02-04 | X4 Pharmaceuticals, Inc. | Compositions of CXCR4 inhibitors and methods of preparation and use |
| JP2023517956A (ja) | 2020-03-10 | 2023-04-27 | 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 | 好中球減少症を処置する方法 |
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| ATE405277T1 (de) * | 1999-04-26 | 2008-09-15 | Edwards Lifesciences Ag | Substitutions-infusionflüssigkeit und zitratanticoagulation |
| NZ524421A (en) * | 2000-09-15 | 2005-02-25 | Anormed Inc | Chemokine receptor binding heterocyclic compounds |
| DK1317451T3 (da) * | 2000-09-15 | 2006-12-18 | Anormed Inc | Kemokinreceptorbindende heterocykliske forbindelser |
| 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 |
| MXPA04006136A (es) * | 2001-12-21 | 2004-11-01 | Anormed Inc | Compuestos heterociclicos que se unen a receptor de quimiocina con eficacia incrementada. |
| US6743194B2 (en) * | 2002-03-28 | 2004-06-01 | Igal Sharon | Multi-compartment syringe |
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- 2005-07-29 US US11/573,116 patent/US20080096861A1/en not_active Abandoned
- 2005-07-29 TW TW094125858A patent/TW200612935A/zh unknown
- 2005-07-29 CA CA002575560A patent/CA2575560A1/en not_active Abandoned
- 2005-07-29 WO PCT/US2005/026797 patent/WO2006020415A1/en not_active Ceased
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