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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- FEHKLDRBMKRELY-UHFFFAOYSA-N n-methyl-n-[[1-[2-(1-methylimidazol-4-yl)ethyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CCC1=CN(C)C=N1 FEHKLDRBMKRELY-UHFFFAOYSA-N 0.000 claims 1
- IEIXJEORNZDGHV-UHFFFAOYSA-N n-methyl-n-[[1-[2-(3-methylimidazol-4-yl)ethyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CCC1=CN=CN1C IEIXJEORNZDGHV-UHFFFAOYSA-N 0.000 claims 1
- ZPPFIEZIZKYHFC-UHFFFAOYSA-N n-methyl-n-[[1-[3-(pyridin-2-ylmethylamino)propyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CCCNCC1=CC=CC=N1 ZPPFIEZIZKYHFC-UHFFFAOYSA-N 0.000 claims 1
- SLDUKYQEMGDZLU-UHFFFAOYSA-N n-methyl-n-[[1-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CC(C=C1)=CC=C1CNCC1=CC=CC=N1 SLDUKYQEMGDZLU-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 10
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
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- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical class CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 1
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- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
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| JP (1) | JP2008508357A (enExample) |
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|---|---|---|---|---|
| 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 |
| PT1961744E (pt) | 2005-11-18 | 2013-05-15 | Ono Pharmaceutical Co | Composto que contém um grupo básico e sua utilização |
| US8618122B2 (en) | 2006-05-16 | 2013-12-31 | Ono Pharmaceutical Co., Ltd. | Compound having acidic group which may be protected, and use thereof |
| WO2008016006A1 (fr) | 2006-07-31 | 2008-02-07 | Ono Pharmaceutical Co., Ltd. | Composé auquel un groupe cyclique est lié par une liaison spiro et son utilisation |
| US8586748B2 (en) * | 2008-04-09 | 2013-11-19 | Boehringer Ingelheim International Gmbh | 2-sulfonylamino-4-heteroaryl butyramide antagonists of CCR10 |
| AU2011336397B2 (en) | 2010-12-03 | 2016-12-15 | Emory University | Chemokine CXCR4 receptor modulators and uses related thereto |
| EA026134B1 (ru) | 2010-12-16 | 2017-03-31 | Ф. Хоффманн-Ля Рош Аг | Трициклические ингибиторы pi3k и способы их применения |
| US8653089B2 (en) | 2011-02-09 | 2014-02-18 | F. Hoffmann-La Roche Ag | Heterocyclic compounds and methods of use |
| WO2015175855A1 (en) | 2014-05-16 | 2015-11-19 | Emory University | Chemokine cxcr4 and ccr5 receptor modulators and used 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 |
| CN109069426B (zh) | 2015-12-14 | 2021-10-29 | X4 制药有限公司 | 治疗癌症的方法 |
| CN109069486A (zh) | 2015-12-14 | 2018-12-21 | X4 制药有限公司 | 治疗癌症的方法 |
| US10610527B2 (en) | 2015-12-22 | 2020-04-07 | X4 Pharmaceuticals, Inc. | Methods for treating immunodeficiency disease |
| US11337969B2 (en) | 2016-04-08 | 2022-05-24 | X4 Pharmaceuticals, Inc. | Methods for treating cancer |
| EP3471716A1 (en) * | 2016-06-16 | 2019-04-24 | Centre National De La Recherche Scientifique | Cxcr4 receptor-binding compounds useful for increasing interferon level |
| JP6994767B2 (ja) | 2016-06-21 | 2022-01-14 | 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 | Ｃｘｃｒ４阻害剤およびその使用 |
| EP3808748B1 (en) | 2016-06-21 | 2026-05-20 | X4 Pharmaceuticals, Inc. | Substituted piperidines as cxcr4-inhibitors |
| US10988465B2 (en) | 2016-06-21 | 2021-04-27 | X4 Pharmaceuticals, Inc. | CXCR4 inhibitors and uses thereof |
| US11497744B2 (en) | 2017-02-21 | 2022-11-15 | Emory University | Chemokine CXCR4 receptor modulators and uses related thereto |
| EP3768256A4 (en) | 2018-03-19 | 2021-11-24 | Emory University | PAN-TROPICAL ENTRANCE 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 |
| CN115515585A (zh) | 2020-03-10 | 2022-12-23 | X4 制药有限公司 | 用于治疗中性粒细胞减少症的方法 |
| WO2023003862A1 (en) | 2021-07-19 | 2023-01-26 | Emory University | Cxcr4 modulators and uses related thereto |
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| WO2000064456A2 (en) * | 1999-04-26 | 2000-11-02 | Pe Chou Chang | Substitution infusion fluid and citrate anticoagulation |
| NZ524421A (en) * | 2000-09-15 | 2005-02-25 | Anormed Inc | Chemokine receptor binding heterocyclic compounds |
| 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 |
| KR20030034184A (ko) * | 2000-09-15 | 2003-05-01 | 아노르메드 인코포레이티드 | 케모킨 수용체 결합 헤테로사이클릭 화합물 |
| CA2467718C (en) * | 2001-12-21 | 2011-04-26 | Anormed Inc. | Chemokine receptor binding heterocyclic compounds with enhanced efficacy |
| US6743194B2 (en) * | 2002-03-28 | 2004-06-01 | Igal Sharon | Multi-compartment syringe |
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2005
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- 2005-07-29 EP EP05776484A patent/EP1778231A4/en not_active Withdrawn
- 2005-07-29 JP JP2007524853A patent/JP2008508357A/ja active Pending
- 2005-07-29 MX MX2007001514A patent/MX2007001514A/es not_active Application Discontinuation
- 2005-07-29 CA CA002575560A patent/CA2575560A1/en not_active Abandoned
- 2005-07-29 WO PCT/US2005/026797 patent/WO2006020415A1/en not_active Ceased
- 2005-07-29 US US11/573,116 patent/US20080096861A1/en not_active Abandoned
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