RU2351592C2 - Производные тетрагидрохинолина и фармацевтическая композиция на их основе для лечения и профилактики вич-инфекции - Google Patents
Производные тетрагидрохинолина и фармацевтическая композиция на их основе для лечения и профилактики вич-инфекции Download PDFInfo
- Publication number
- RU2351592C2 RU2351592C2 RU2007106779/04A RU2007106779A RU2351592C2 RU 2351592 C2 RU2351592 C2 RU 2351592C2 RU 2007106779/04 A RU2007106779/04 A RU 2007106779/04A RU 2007106779 A RU2007106779 A RU 2007106779A RU 2351592 C2 RU2351592 C2 RU 2351592C2
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- RU
- Russia
- Prior art keywords
- methyl
- pyridin
- imidazo
- tetrahydro
- quinolinamine
- Prior art date
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- 208000031886 HIV Infections Diseases 0.000 title claims abstract 6
- 208000037357 HIV infectious disease Diseases 0.000 title claims abstract 6
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 title claims abstract 6
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract 3
- 238000011282 treatment Methods 0.000 title claims 5
- 230000002265 prevention Effects 0.000 title claims 3
- 125000000147 tetrahydroquinolinyl group Chemical class N1(CCCC2=CC=CC=C12)* 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract 84
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 69
- 125000000217 alkyl group Chemical group 0.000 claims abstract 68
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 38
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract 27
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 22
- -1 -Racycloalkyl Chemical group 0.000 claims abstract 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract 12
- 150000002367 halogens Chemical class 0.000 claims abstract 12
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- 238000000034 method Methods 0.000 claims abstract 11
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- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 9
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- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 9
- 150000002148 esters Chemical class 0.000 claims abstract 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 25
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 17
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 8
- 125000002947 alkylene group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
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- 238000006268 reductive amination reaction Methods 0.000 claims 4
- ZNYNQVPNMSPERK-QHCPKHFHSA-N (8s)-n-(cyclopropylmethyl)-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(C)CCN1C1=CC=CC2=NC(CN(CC3CC3)[C@@H]3C4=NC=CC=C4CCC3)=CN12 ZNYNQVPNMSPERK-QHCPKHFHSA-N 0.000 claims 3
- XCBGMXUKNZCYDY-RPWUZVMVSA-N (8s)-n-(cyclopropylmethyl)-n-[[5-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1[C@H](N(C)C)CCN1C1=CC=CC2=NC(CN(CC3CC3)[C@@H]3C4=NC=CC=C4CCC3)=CN12 XCBGMXUKNZCYDY-RPWUZVMVSA-N 0.000 claims 3
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- DUXQJVSQUNTORQ-PKTZIBPZSA-N (8s)-n-[[5-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]imidazo[1,2-a]pyridin-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(N=C1C=CC=2)=CN1C=2N1CC[C@@H](N(C)C)C1 DUXQJVSQUNTORQ-PKTZIBPZSA-N 0.000 claims 3
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- OLNFUKUUTXMWRQ-NRFANRHFSA-N 2-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]ethanol Chemical compound C1CN(C)CCN1C1=CC=CC2=NC(CN(CCO)[C@@H]3C4=NC=CC=C4CCC3)=CN12 OLNFUKUUTXMWRQ-NRFANRHFSA-N 0.000 claims 3
- VVCKQGVIFYLFLK-QFIPXVFZSA-N 3-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]propan-1-ol Chemical compound C1CN(C)CCN1C1=CC=CC2=NC(CN(CCCO)[C@@H]3C4=NC=CC=C4CCC3)=CN12 VVCKQGVIFYLFLK-QFIPXVFZSA-N 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
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- MFPNAWHIPSNSRA-QFIPXVFZSA-N (8s)-n-methyl-n-[[5-(4-propan-2-ylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(C(C)C)CCN1C1=CC=CC2=NC(CN(C)[C@@H]3C4=NC=CC=C4CCC3)=CN12 MFPNAWHIPSNSRA-QFIPXVFZSA-N 0.000 claims 2
- IJRADFNTAYCYKO-QFIPXVFZSA-N (8s)-n-methyl-n-[[5-[methyl-(1-methylpiperidin-4-yl)amino]imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(N=C1C=CC=2)=CN1C=2N(C)C1CCN(C)CC1 IJRADFNTAYCYKO-QFIPXVFZSA-N 0.000 claims 2
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
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- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
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- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- JPVKWRVSRZEMDF-FQEVSTJZSA-N n,n,n'-trimethyl-n'-[2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]imidazo[1,2-a]pyridin-5-yl]ethane-1,2-diamine Chemical compound C1CCC2=CC=CN=C2[C@H]1N(C)CC1=CN2C(N(C)CCN(C)C)=CC=CC2=N1 JPVKWRVSRZEMDF-FQEVSTJZSA-N 0.000 claims 2
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- ITPSDEVJHDJOQI-UHFFFAOYSA-N n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(C)CCN1C1=CC=CC2=NC(CNC3C4=NC=CC=C4CCC3)=CN12 ITPSDEVJHDJOQI-UHFFFAOYSA-N 0.000 claims 2
- QJSUPMMHOXHUJT-UHFFFAOYSA-N n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-n-propan-2-yl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C(C)C)CC(N=C1C=CC=2)=CN1C=2N1CCN(C)CC1 QJSUPMMHOXHUJT-UHFFFAOYSA-N 0.000 claims 2
- KCYJZDNOWILGPM-VQCQRNETSA-N n-[[5-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]imidazo[1,2-a]pyridin-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1[C@H](N(C)C)CCN1C1=CC=CC2=NC(CN(C)C3C4=NC=CC=C4CCC3)=CN12 KCYJZDNOWILGPM-VQCQRNETSA-N 0.000 claims 2
- LLTLSDYWBUFMNN-DUSLRRAJSA-N n-[[5-[(3r)-3-aminopyrrolidin-1-yl]imidazo[1,2-a]pyridin-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(N=C1C=CC=2)=CN1C=2N1CC[C@@H](N)C1 LLTLSDYWBUFMNN-DUSLRRAJSA-N 0.000 claims 2
- VRZMFUIDEOPILH-UHFFFAOYSA-N n-[[5-[4-(2-methoxyethyl)piperazin-1-yl]imidazo[1,2-a]pyridin-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(CCOC)CCN1C1=CC=CC2=NC(CN(C)C3C4=NC=CC=C4CCC3)=CN12 VRZMFUIDEOPILH-UHFFFAOYSA-N 0.000 claims 2
- LAXBNABGPSQIHG-UHFFFAOYSA-N n-[[5-[4-(dimethylamino)piperidin-1-yl]imidazo[1,2-a]pyridin-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CC(N(C)C)CCN1C1=CC=CC2=NC(CN(C)C3C4=NC=CC=C4CCC3)=CN12 LAXBNABGPSQIHG-UHFFFAOYSA-N 0.000 claims 2
- ZPGMMMUFUCRFPZ-UHFFFAOYSA-N n-cyclopropyl-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(C)CCN1C1=CC=CC2=NC(CN(C3CC3)C3C4=NC=CC=C4CCC3)=CN12 ZPGMMMUFUCRFPZ-UHFFFAOYSA-N 0.000 claims 2
- AQOBWZRQYWFSAW-UHFFFAOYSA-N n-methyl-n-[(5-piperazin-1-ylimidazo[1,2-a]pyridin-2-yl)methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(N=C1C=CC=2)=CN1C=2N1CCNCC1 AQOBWZRQYWFSAW-UHFFFAOYSA-N 0.000 claims 2
- VMDADMFTSYKUBK-UHFFFAOYSA-N n-methyl-n-[[5-(4-methyl-1,4-diazepan-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(N=C1C=CC=2)=CN1C=2N1CCCN(C)CC1 VMDADMFTSYKUBK-UHFFFAOYSA-N 0.000 claims 2
- FRHRAPSVOIMXJY-UHFFFAOYSA-N n-methyl-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(N=C1C=CC=2)=CN1C=2N1CCN(C)CC1 FRHRAPSVOIMXJY-UHFFFAOYSA-N 0.000 claims 2
- IXNIIYLSQFRXKT-UHFFFAOYSA-N n-methyl-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-amine Chemical compound C1CCCC2=CC=CN=C2C1N(C)CC(N=C1C=CC=2)=CN1C=2N1CCN(C)CC1 IXNIIYLSQFRXKT-UHFFFAOYSA-N 0.000 claims 2
- NTZBKAPQFLBYKJ-UHFFFAOYSA-N n-methyl-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-6,7-dihydro-5h-cyclopenta[b]pyridin-7-amine Chemical compound C1CC2=CC=CN=C2C1N(C)CC(N=C1C=CC=2)=CN1C=2N1CCN(C)CC1 NTZBKAPQFLBYKJ-UHFFFAOYSA-N 0.000 claims 2
- MFPNAWHIPSNSRA-UHFFFAOYSA-N n-methyl-n-[[5-(4-propan-2-ylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(C(C)C)CCN1C1=CC=CC2=NC(CN(C)C3C4=NC=CC=C4CCC3)=CN12 MFPNAWHIPSNSRA-UHFFFAOYSA-N 0.000 claims 2
- NGWDLBUQTRJLNR-UHFFFAOYSA-N n-methyl-n-[[5-[4-(methylamino)piperidin-1-yl]imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CC(NC)CCN1C1=CC=CC2=NC(CN(C)C3C4=NC=CC=C4CCC3)=CN12 NGWDLBUQTRJLNR-UHFFFAOYSA-N 0.000 claims 2
- KGGOEFQJWNRJEG-UHFFFAOYSA-N n-methyl-n-[[5-[methyl-(1-methylpyrrolidin-3-yl)amino]imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(N=C1C=CC=2)=CN1C=2N(C)C1CCN(C)C1 KGGOEFQJWNRJEG-UHFFFAOYSA-N 0.000 claims 2
- JPTZJWVMCKRUDC-UHFFFAOYSA-N n-propan-2-yl-n-[[5-(4-propan-2-ylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C(C)C)CC(N=C1C=CC=2)=CN1C=2N1CCN(C(C)C)CC1 JPTZJWVMCKRUDC-UHFFFAOYSA-N 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- FRHRAPSVOIMXJY-HXUWFJFHSA-N (8r)-n-methyl-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@H]1C2=NC=CC=C2CCC1)CC(N=C1C=CC=2)=CN1C=2N1CCN(C)CC1 FRHRAPSVOIMXJY-HXUWFJFHSA-N 0.000 claims 1
- FAFYHBSFPVJQDP-SANMLTNESA-N (8s)-n-[(2-methoxyphenyl)methyl]-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound COC1=CC=CC=C1CN([C@@H]1C2=NC=CC=C2CCC1)CC1=CN(C(=CC=C2)N3CCN(C)CC3)C2=N1 FAFYHBSFPVJQDP-SANMLTNESA-N 0.000 claims 1
- NRNCNGNZSXHFCR-MHZLTWQESA-N (8s)-n-[(3-methoxyphenyl)methyl]-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound COC1=CC=CC(CN(CC=2N=C3C=CC=C(N3C=2)N2CCN(C)CC2)[C@@H]2C3=NC=CC=C3CCC2)=C1 NRNCNGNZSXHFCR-MHZLTWQESA-N 0.000 claims 1
- KZJFXCOQWHOXAP-MHZLTWQESA-N (8s)-n-[(4-methoxyphenyl)methyl]-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1=CC(OC)=CC=C1CN([C@@H]1C2=NC=CC=C2CCC1)CC1=CN(C(=CC=C2)N3CCN(C)CC3)C2=N1 KZJFXCOQWHOXAP-MHZLTWQESA-N 0.000 claims 1
- JALJTKRUKDCSQJ-YTTGMZPUSA-N (8s)-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-n-[(4-phenylphenyl)methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(C)CCN1C1=CC=CC2=NC(CN(CC=3C=CC(=CC=3)C=3C=CC=CC=3)[C@@H]3C4=NC=CC=C4CCC3)=CN12 JALJTKRUKDCSQJ-YTTGMZPUSA-N 0.000 claims 1
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- BSXVSUGBNPANRN-SANMLTNESA-N (8s)-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-n-[[3-(trifluoromethyl)phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(C)CCN1C1=CC=CC2=NC(CN(CC=3C=C(C=CC=3)C(F)(F)F)[C@@H]3C4=NC=CC=C4CCC3)=CN12 BSXVSUGBNPANRN-SANMLTNESA-N 0.000 claims 1
- MJKGXNDWAPDFFX-SANMLTNESA-N (8s)-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-n-[[4-(trifluoromethyl)phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(C)CCN1C1=CC=CC2=NC(CN(CC=3C=CC(=CC=3)C(F)(F)F)[C@@H]3C4=NC=CC=C4CCC3)=CN12 MJKGXNDWAPDFFX-SANMLTNESA-N 0.000 claims 1
- QGTROIYUDZXOLO-IBGZPJMESA-N (8s)-n-[[5-[2-(dimethylamino)ethoxy]imidazo[1,2-a]pyridin-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2[C@H]1N(C)CC1=CN2C(OCCN(C)C)=CC=CC2=N1 QGTROIYUDZXOLO-IBGZPJMESA-N 0.000 claims 1
- BNOPLAIRDVCQBH-SANMLTNESA-N (8s)-n-benzyl-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(C)CCN1C1=CC=CC2=NC(CN(CC=3C=CC=CC=3)[C@@H]3C4=NC=CC=C4CCC3)=CN12 BNOPLAIRDVCQBH-SANMLTNESA-N 0.000 claims 1
- PLWPORJLNOVZAM-QFIPXVFZSA-N (8s)-n-methyl-n-[[5-(2-piperidin-1-ylethoxy)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(N=C1C=CC=2)=CN1C=2OCCN1CCCCC1 PLWPORJLNOVZAM-QFIPXVFZSA-N 0.000 claims 1
- FIHSQKVAYHSCPE-QFIPXVFZSA-N (8s)-n-methyl-n-[[5-(2-piperidin-1-ylethylamino)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(N=C1C=CC=2)=CN1C=2NCCN1CCCCC1 FIHSQKVAYHSCPE-QFIPXVFZSA-N 0.000 claims 1
- SAUNXVLNCQIKEY-NRFANRHFSA-N (8s)-n-methyl-n-[[5-(2-pyrrolidin-1-ylethylamino)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(N=C1C=CC=2)=CN1C=2NCCN1CCCC1 SAUNXVLNCQIKEY-NRFANRHFSA-N 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- JPVKWRVSRZEMDF-UHFFFAOYSA-N n,n,n'-trimethyl-n'-[2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]imidazo[1,2-a]pyridin-5-yl]ethane-1,2-diamine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=CN2C(N(C)CCN(C)C)=CC=CC2=N1 JPVKWRVSRZEMDF-UHFFFAOYSA-N 0.000 claims 1
- ROQQDVQEYJVOLI-UHFFFAOYSA-N n-[(5-piperazin-1-ylimidazo[1,2-a]pyridin-2-yl)methyl]-n-propan-2-yl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C(C)C)CC(N=C1C=CC=2)=CN1C=2N1CCNCC1 ROQQDVQEYJVOLI-UHFFFAOYSA-N 0.000 claims 1
- GMZLORPERFPBOQ-UHFFFAOYSA-N n-[[5-(3,5-dimethylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1C(C)NC(C)CN1C1=CC=CC2=NC(CN(C)C3C4=NC=CC=C4CCC3)=CN12 GMZLORPERFPBOQ-UHFFFAOYSA-N 0.000 claims 1
- KCYJZDNOWILGPM-BGERDNNASA-N n-[[5-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]imidazo[1,2-a]pyridin-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1[C@@H](N(C)C)CCN1C1=CC=CC2=NC(CN(C)C3C4=NC=CC=C4CCC3)=CN12 KCYJZDNOWILGPM-BGERDNNASA-N 0.000 claims 1
- BABAEMPTYIHDCU-UHFFFAOYSA-N n-[[5-[4-[(dimethylamino)methyl]phenyl]imidazo[1,2-a]pyridin-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1=CC(CN(C)C)=CC=C1C1=CC=CC2=NC(CN(C)C3C4=NC=CC=C4CCC3)=CN12 BABAEMPTYIHDCU-UHFFFAOYSA-N 0.000 claims 1
- DNTSUXKFOYLEMP-UHFFFAOYSA-N n-methyl-n-[[5-(3,4,5-trimethylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1C(C)N(C)C(C)CN1C1=CC=CC2=NC(CN(C)C3C4=NC=CC=C4CCC3)=CN12 DNTSUXKFOYLEMP-UHFFFAOYSA-N 0.000 claims 1
- 239000012038 nucleophile Substances 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 5
- 102000005962 receptors Human genes 0.000 abstract 2
- 108020003175 receptors Proteins 0.000 abstract 2
- 239000003446 ligand Substances 0.000 abstract 1
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Classifications
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
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| US60/606,742 | 2004-09-02 | ||
| US61076504P | 2004-09-17 | 2004-09-17 | |
| US60/610,765 | 2004-09-17 |
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| RU2007106779A RU2007106779A (ru) | 2008-10-10 |
| RU2351592C2 true RU2351592C2 (ru) | 2009-04-10 |
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| RU2007106780/04A RU2352567C2 (ru) | 2004-09-02 | 2005-08-31 | Производные тетрагидрохинолина, демонстрирующие защитное от вич-инфекции действие |
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| RU2007106780/04A RU2352567C2 (ru) | 2004-09-02 | 2005-08-31 | Производные тетрагидрохинолина, демонстрирующие защитное от вич-инфекции действие |
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| US (2) | US20070254910A1 (https=) |
| EP (2) | EP1799671A4 (https=) |
| JP (2) | JP2008511669A (https=) |
| KR (2) | KR20070049682A (https=) |
| AR (2) | AR050302A1 (https=) |
| AU (2) | AU2005279835A1 (https=) |
| BR (1) | BRPI0514881A (https=) |
| CA (2) | CA2578746A1 (https=) |
| IL (1) | IL181419A0 (https=) |
| MA (1) | MA28872B1 (https=) |
| MX (2) | MX2007002679A (https=) |
| NO (2) | NO20071366L (https=) |
| PE (2) | PE20060712A1 (https=) |
| RU (2) | RU2351592C2 (https=) |
| TW (2) | TW200621754A (https=) |
| WO (2) | WO2006026703A2 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2798107C2 (ru) * | 2018-10-10 | 2023-06-15 | Куровир Аб | Производные 2,6-диметил-n-((пиридин-4-ил)метил)имидазо[1,2-b]пиридазин-8-амина и 2,5-диметил-n-[(пиридин-4-ил)метил]пиразоло[1,5-a]пиримидин-7-амина для лечения вирусных инфекций |
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| JP2008511669A (ja) * | 2004-09-02 | 2008-04-17 | スミスクライン ビーチャム コーポレーション | 化合物 |
| PE20070946A1 (es) * | 2006-01-25 | 2007-10-16 | Smithkline Beecham Corp | COMPUESTOS DERIVADOS DE IMIDAZO[1,2-a]PIRIDINA COMO MODULADORES DEL RECEPTOR DE QUIMIOQUINA (CXCR4) |
| EP2042503B1 (en) | 2006-05-16 | 2013-01-30 | 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 |
| US7767826B2 (en) * | 2007-10-05 | 2010-08-03 | Pharmatech International, Inc. | Process for the synthesis of L-(+)-ergothioneine |
| EP2217069A4 (en) * | 2007-11-09 | 2012-03-14 | Salk Inst For Biological Studi | INHIBITORS OF NON-NUCLEOSIDE INHIBITORS OF THE REVERSE TRANSCRIPTASE |
| 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 |
| MX373103B (es) | 2014-02-13 | 2020-04-17 | Incyte Holdings Corp | Ciclopropilaminas como inhibidores de desmetilasa específica de lisina 1 (lsd1). |
| SI3105218T1 (sl) | 2014-02-13 | 2019-11-29 | Incyte Corp | Ciklopropilamini kot inhibitorji LSD1 |
| WO2016007722A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| EP3277689B1 (en) | 2015-04-03 | 2019-09-04 | Incyte Corporation | Heterocyclic compounds as lsd1 inhibitors |
| LT3334709T (lt) | 2015-08-12 | 2025-03-10 | Incyte Holdings Corporation | Lsd1 inhibitoriaus druskos |
| WO2017106332A1 (en) | 2015-12-14 | 2017-06-22 | X4 Pharmaceuticals, Inc. | Methods for treating cancer |
| CN109069426B (zh) | 2015-12-14 | 2021-10-29 | X4 制药有限公司 | 治疗癌症的方法 |
| KR102738306B1 (ko) * | 2015-12-15 | 2024-12-03 | 브리스톨-마이어스 스큅 컴퍼니 | Cxcr4 수용체 길항제 |
| PL3393468T3 (pl) | 2015-12-22 | 2023-01-23 | X4 Pharmaceuticals, Inc. | Metody leczenia niedoboru odporności |
| US11337969B2 (en) | 2016-04-08 | 2022-05-24 | X4 Pharmaceuticals, Inc. | Methods for treating cancer |
| WO2017223243A1 (en) | 2016-06-21 | 2017-12-28 | X4 Pharmaceuticals, Inc. | Cxcr4 inhibitors and uses thereof |
| CN109640988A (zh) | 2016-06-21 | 2019-04-16 | X4 制药有限公司 | Cxcr4抑制剂及其用途 |
| ES2870920T3 (es) | 2016-06-21 | 2021-10-28 | X4 Pharmaceuticals Inc | Inhibidores de CXCR4 y usos de los mismos |
| EP3585387A4 (en) | 2017-02-21 | 2020-08-12 | Emory University | CHEMIOKIN CXCR4 RECEIVER MODULATORS AND THEIR USES |
| JP7282786B2 (ja) * | 2017-09-25 | 2023-05-29 | シージーンテック （スーチョウ， チャイナ） カンパニー リミテッド | Ｃｘｃｒ４阻害剤としてのヘテロアリール化合物、それを用いた組成物及び方法 |
| 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 |
| WO2020047198A1 (en) | 2018-08-31 | 2020-03-05 | Incyte Corporation | Salts of an lsd1 inhibitor and processes for preparing the same |
| CA3171250A1 (en) | 2020-03-10 | 2021-09-16 | E. Lynne KELLEY | Methods for treating neutropenia |
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| SU1738088A3 (ru) * | 1987-07-17 | 1992-05-30 | Жансен Фармасетика Н.В. (Фирма) | Способ получени цис-производных N-(3-окси-4-пиперидинил)бензамида |
| US6734191B2 (en) * | 2000-09-15 | 2004-05-11 | Anormed, Inc. | Chemokine receptor binding heterocyclic compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| US6835731B2 (en) * | 2000-09-15 | 2004-12-28 | Anormed, Inc. | Chemokine receptor binding heterocyclic compounds |
| CA2419224A1 (en) * | 2000-09-15 | 2002-03-21 | Anormed Inc. | Chemokine receptor binding heterocyclic compounds |
| CA2467718C (en) * | 2001-12-21 | 2011-04-26 | Anormed Inc. | Chemokine receptor binding heterocyclic compounds with enhanced efficacy |
| EP1613613B1 (en) * | 2003-04-11 | 2021-06-02 | Genzyme Corporation | Cxcr4 chemokine receptor binding compounds |
| JP2008511669A (ja) * | 2004-09-02 | 2008-04-17 | スミスクライン ビーチャム コーポレーション | 化合物 |
| WO2006036816A2 (en) * | 2004-09-24 | 2006-04-06 | Smithkline Beecham Corporation | Chemical compounds |
| EP1919872A4 (en) * | 2005-08-31 | 2009-08-05 | Smithkline Beecham Corp | CHEMICAL COMPOUNDS |
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2005
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- 2005-08-28 WO PCT/US2005/031099 patent/WO2006026703A2/en not_active Ceased
- 2005-08-28 MX MX2007002679A patent/MX2007002679A/es not_active Application Discontinuation
- 2005-08-28 EP EP05815072A patent/EP1799671A4/en not_active Withdrawn
- 2005-08-31 US US11/574,586 patent/US20070254910A1/en not_active Abandoned
- 2005-08-31 RU RU2007106779/04A patent/RU2351592C2/ru not_active IP Right Cessation
- 2005-08-31 US US11/574,583 patent/US20070232615A1/en not_active Abandoned
- 2005-08-31 CA CA002578746A patent/CA2578746A1/en not_active Abandoned
- 2005-08-31 KR KR1020077007349A patent/KR20070049682A/ko not_active Withdrawn
- 2005-08-31 KR KR1020077007549A patent/KR20070053313A/ko not_active Withdrawn
- 2005-08-31 RU RU2007106780/04A patent/RU2352567C2/ru not_active IP Right Cessation
- 2005-08-31 AU AU2005279835A patent/AU2005279835A1/en not_active Abandoned
- 2005-08-31 JP JP2007530352A patent/JP2008511668A/ja active Pending
- 2005-08-31 EP EP05794929A patent/EP1784185A4/en not_active Withdrawn
- 2005-08-31 AU AU2005282753A patent/AU2005282753A1/en not_active Abandoned
- 2005-08-31 CA CA002579059A patent/CA2579059A1/en not_active Abandoned
- 2005-08-31 BR BRPI0514881-2A patent/BRPI0514881A/pt not_active IP Right Cessation
- 2005-08-31 MX MX2007002615A patent/MX2007002615A/es not_active Application Discontinuation
- 2005-08-31 WO PCT/US2005/031098 patent/WO2006028896A2/en not_active Ceased
- 2005-09-01 AR ARP050103665A patent/AR050302A1/es not_active Application Discontinuation
- 2005-09-01 AR ARP050103666A patent/AR051565A1/es not_active Application Discontinuation
- 2005-09-01 PE PE2005001007A patent/PE20060712A1/es not_active Application Discontinuation
- 2005-09-01 PE PE2005001008A patent/PE20060656A1/es not_active Application Discontinuation
- 2005-09-02 TW TW094130018A patent/TW200621754A/zh unknown
- 2005-09-02 TW TW094130013A patent/TW200612921A/zh unknown
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2007
- 2007-02-19 IL IL181419A patent/IL181419A0/en unknown
- 2007-03-14 NO NO20071366A patent/NO20071366L/no not_active Application Discontinuation
- 2007-03-15 NO NO20071418A patent/NO20071418L/no not_active Application Discontinuation
- 2007-03-23 MA MA29772A patent/MA28872B1/fr unknown
Patent Citations (2)
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| SU1738088A3 (ru) * | 1987-07-17 | 1992-05-30 | Жансен Фармасетика Н.В. (Фирма) | Способ получени цис-производных N-(3-окси-4-пиперидинил)бензамида |
| US6734191B2 (en) * | 2000-09-15 | 2004-05-11 | Anormed, Inc. | Chemokine receptor binding heterocyclic compounds |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2798107C2 (ru) * | 2018-10-10 | 2023-06-15 | Куровир Аб | Производные 2,6-диметил-n-((пиридин-4-ил)метил)имидазо[1,2-b]пиридазин-8-амина и 2,5-диметил-n-[(пиридин-4-ил)метил]пиразоло[1,5-a]пиримидин-7-амина для лечения вирусных инфекций |
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