JP2004524349A5 - - Google Patents
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- JP2004524349A5 JP2004524349A5 JP2002576233A JP2002576233A JP2004524349A5 JP 2004524349 A5 JP2004524349 A5 JP 2004524349A5 JP 2002576233 A JP2002576233 A JP 2002576233A JP 2002576233 A JP2002576233 A JP 2002576233A JP 2004524349 A5 JP2004524349 A5 JP 2004524349A5
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- JP
- Japan
- Prior art keywords
- group
- alkyl
- optionally substituted
- amino
- groups
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 96
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 61
- 150000001875 compounds Chemical class 0.000 claims 43
- -1 homopiperazinyl group Chemical group 0.000 claims 38
- 229910052739 hydrogen Inorganic materials 0.000 claims 31
- 239000001257 hydrogen Substances 0.000 claims 31
- 125000005936 piperidyl group Chemical group 0.000 claims 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 30
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 29
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 29
- 125000004193 piperazinyl group Chemical group 0.000 claims 26
- 125000004076 pyridyl group Chemical group 0.000 claims 26
- 229910052757 nitrogen Chemical group 0.000 claims 25
- 125000003884 phenylalkyl group Chemical group 0.000 claims 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 20
- 125000002757 morpholinyl group Chemical group 0.000 claims 20
- 125000003118 aryl group Chemical group 0.000 claims 19
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 18
- 125000003277 amino group Chemical group 0.000 claims 18
- 125000004663 dialkyl amino group Chemical group 0.000 claims 17
- 125000003545 alkoxy group Chemical group 0.000 claims 15
- 125000003282 alkyl amino group Chemical group 0.000 claims 15
- AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 15
- 125000003386 piperidinyl group Chemical group 0.000 claims 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 12
- 125000005842 heteroatom Chemical group 0.000 claims 12
- 229910052717 sulfur Inorganic materials 0.000 claims 12
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 125000001624 naphthyl group Chemical group 0.000 claims 10
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical group C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims 10
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 8
- 125000002619 bicyclic group Chemical group 0.000 claims 8
- 125000002950 monocyclic group Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 125000004434 sulfur atom Chemical group 0.000 claims 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 7
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 7
- 125000002252 acyl group Chemical group 0.000 claims 7
- 125000002883 imidazolyl group Chemical group 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 7
- 125000004442 acylamino group Chemical group 0.000 claims 6
- 125000004450 alkenylene group Chemical group 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000005843 halogen group Chemical class 0.000 claims 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 6
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 6
- 150000002829 nitrogen Chemical class 0.000 claims 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical class COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 6
- 125000005309 thioalkoxy group Chemical group 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 125000002947 alkylene group Chemical group 0.000 claims 5
- 125000005237 alkyleneamino group Chemical group 0.000 claims 5
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical class NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims 5
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000002636 imidazolinyl group Chemical group 0.000 claims 5
- 125000005956 isoquinolyl group Chemical group 0.000 claims 5
- 125000005493 quinolyl group Chemical group 0.000 claims 5
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 4
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims 4
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 claims 4
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 4
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 125000000169 tricyclic heterocycle group Chemical group 0.000 claims 4
- OKSXITPKUOLCED-UHFFFAOYSA-N 6-[1-amino-4-[4-(dimethylamino)-2-methylquinolin-6-yl]-6-(4-pyridin-4-ylpiperazin-1-yl)-2h-1,3,5-triazin-2-yl]-n,n,2-trimethylquinolin-4-amine Chemical compound C1=C2C(N(C)C)=CC(C)=NC2=CC=C1C(N1N)N=C(C=2C=C3C(N(C)C)=CC(C)=NC3=CC=2)N=C1N(CC1)CCN1C1=CC=NC=C1 OKSXITPKUOLCED-UHFFFAOYSA-N 0.000 claims 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 3
- 230000001093 anti-cancer Effects 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 3
- 238000000638 solvent extraction Methods 0.000 claims 3
- 125000005208 trialkylammonium group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 claims 2
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 2
- FNJLDQWKHZNBEE-UHFFFAOYSA-N 2,4-bis[4-(dimethylamino)-2-methylquinolin-6-yl]-6-n-methyl-6-n-(1-methylpiperidin-4-yl)-2h-1,3,5-triazine-1,6-diamine Chemical compound C1=C2C(N(C)C)=CC(C)=NC2=CC=C1C(N1N)N=C(C=2C=C3C(N(C)C)=CC(C)=NC3=CC=2)N=C1N(C)C1CCN(C)CC1 FNJLDQWKHZNBEE-UHFFFAOYSA-N 0.000 claims 2
- GYSITELFIHMOFS-UHFFFAOYSA-N 6-[1-amino-4,6-bis(4-amino-2-methylquinolin-6-yl)-2h-1,3,5-triazin-2-yl]-2-methylquinolin-4-amine Chemical compound N1=C(C)C=C(N)C2=CC(C3=NC(N(C(=N3)C=3C=C4C(N)=CC(C)=NC4=CC=3)N)C3=CC4=C(N)C=C(N=C4C=C3)C)=CC=C21 GYSITELFIHMOFS-UHFFFAOYSA-N 0.000 claims 2
- YFIBXWINRALTBT-UHFFFAOYSA-N 6-[1-amino-4-(4-amino-2-methylquinolin-6-yl)-6-phenylmethoxy-2h-1,3,5-triazin-2-yl]-2-methylquinolin-4-amine Chemical compound C1=CC2=NC(C)=CC(N)=C2C=C1C(N1N)N=C(C=2C=C3C(N)=CC(C)=NC3=CC=2)N=C1OCC1=CC=CC=C1 YFIBXWINRALTBT-UHFFFAOYSA-N 0.000 claims 2
- SGECERHOWPZOTF-UHFFFAOYSA-N 6-[1-amino-4-[4-(dimethylamino)-2-methylquinolin-6-yl]-6-(4-methyl-1,4-diazepan-1-yl)-2h-1,3,5-triazin-2-yl]-n,n,2-trimethylquinolin-4-amine Chemical compound C1=C2C(N(C)C)=CC(C)=NC2=CC=C1C(N1N)N=C(C=2C=C3C(N(C)C)=CC(C)=NC3=CC=2)N=C1N1CCCN(C)CC1 SGECERHOWPZOTF-UHFFFAOYSA-N 0.000 claims 2
- ICSSKLUEDTUPJA-UHFFFAOYSA-N 6-[1-amino-4-[4-(dimethylamino)-2-methylquinolin-6-yl]-6-(4-methylpiperazin-1-yl)-2h-1,3,5-triazin-2-yl]-n,n,2-trimethylquinolin-4-amine Chemical compound C1=C2C(N(C)C)=CC(C)=NC2=CC=C1C(N1N)N=C(C=2C=C3C(N(C)C)=CC(C)=NC3=CC=2)N=C1N1CCN(C)CC1 ICSSKLUEDTUPJA-UHFFFAOYSA-N 0.000 claims 2
- RIMWCSACWKRKDP-UHFFFAOYSA-N 6-[1-amino-4-[4-(dimethylamino)-2-methylquinolin-6-yl]-6-[4-[3-(dimethylamino)propyl]piperazin-1-yl]-2h-1,3,5-triazin-2-yl]-n,n,2-trimethylquinolin-4-amine Chemical compound C1CN(CCCN(C)C)CCN1C1=NC(C=2C=C3C(N(C)C)=CC(C)=NC3=CC=2)=NC(C=2C=C3C(N(C)C)=CC(C)=NC3=CC=2)N1N RIMWCSACWKRKDP-UHFFFAOYSA-N 0.000 claims 2
- CQPQEJRGRATQOV-UHFFFAOYSA-N CN(C1=CC(=NC2=CC=C(C=C12)C1N(C(=NC(=N1)C=1C=C2C(=CC(=NC2=CC=1)C)N(C)C)CN1C=NC=C1)NN)C)C Chemical compound CN(C1=CC(=NC2=CC=C(C=C12)C1N(C(=NC(=N1)C=1C=C2C(=CC(=NC2=CC=1)C)N(C)C)CN1C=NC=C1)NN)C)C CQPQEJRGRATQOV-UHFFFAOYSA-N 0.000 claims 2
- 108091081406 G-quadruplex Proteins 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- GHXKDSSTHVBFHS-UHFFFAOYSA-N NC1=CC(=NC2=CC=C(C=C12)C1N(C(=NC(=N1)C=1C=C2C(=CC(=NC2=CC=1)C)N)C=1C=C2C(=CC(=NC2=CC=1)C)N(C)C)NN)C Chemical compound NC1=CC(=NC2=CC=C(C=C12)C1N(C(=NC(=N1)C=1C=C2C(=CC(=NC2=CC=1)C)N)C=1C=C2C(=CC(=NC2=CC=1)C)N(C)C)NN)C GHXKDSSTHVBFHS-UHFFFAOYSA-N 0.000 claims 2
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 2
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims 2
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims 2
- 125000006542 morpholinylalkyl group Chemical group 0.000 claims 2
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 claims 2
- 238000005192 partition Methods 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical group C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 1
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 102100025573 1-alkyl-2-acetylglycerophosphocholine esterase Human genes 0.000 claims 1
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- TVJCWFRAXNLAJH-UHFFFAOYSA-N 2-n,4-n-bis[4-(dimethylamino)-2-methylquinolin-6-yl]-6-n-[3-(dimethylamino)propyl]-1,3,5-triazine-2,4,6-triamine Chemical compound N1=C(C)C=C(N(C)C)C2=CC(NC=3N=C(NC=4C=C5C(N(C)C)=CC(C)=NC5=CC=4)N=C(N=3)NCCCN(C)C)=CC=C21 TVJCWFRAXNLAJH-UHFFFAOYSA-N 0.000 claims 1
- KVNBKXXDKUNBKG-UHFFFAOYSA-N 3-N',4-N,4-N-trimethyl-2-methylsulfanylmorpholine-3,3,4-triamine Chemical compound CSC1C(N(CCO1)N(C)C)(NC)N KVNBKXXDKUNBKG-UHFFFAOYSA-N 0.000 claims 1
- XXIGIWNERZUIDI-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-amine Chemical compound C1CN(C)CCN1C1=NC=NC(N)=N1 XXIGIWNERZUIDI-UHFFFAOYSA-N 0.000 claims 1
- OKPNOXDDQGTUAH-UHFFFAOYSA-N 4-[3-(dimethylamino)propyl]-1,3,5-triazin-2-amine Chemical compound CN(CCCC1=NC(=NC=N1)N)C OKPNOXDDQGTUAH-UHFFFAOYSA-N 0.000 claims 1
- WRSOLHKLTRTXOC-UHFFFAOYSA-N 6-[1-amino-4-(4-amino-2-methylquinolin-6-yl)-6-[3-(dimethylamino)propoxy]-2h-1,3,5-triazin-2-yl]-2-methylquinolin-4-amine Chemical compound N1=C(C)C=C(N)C2=CC(C=3N=C(N(C(N=3)C=3C=C4C(N)=CC(C)=NC4=CC=3)N)OCCCN(C)C)=CC=C21 WRSOLHKLTRTXOC-UHFFFAOYSA-N 0.000 claims 1
- HCYRPDINFBLRFU-UHFFFAOYSA-N 6-[1-amino-4-(4-amino-2-methylquinolin-6-yl)-6-phenoxy-2h-1,3,5-triazin-2-yl]-2-methylquinolin-4-amine Chemical compound C1=CC2=NC(C)=CC(N)=C2C=C1C(N1N)N=C(C=2C=C3C(N)=CC(C)=NC3=CC=2)N=C1OC1=CC=CC=C1 HCYRPDINFBLRFU-UHFFFAOYSA-N 0.000 claims 1
- ZSCKZGZVIVDZIH-UHFFFAOYSA-N 6-[1-amino-4-(4-amino-2-methylquinolin-6-yl)-6-pyridin-4-yloxy-2h-1,3,5-triazin-2-yl]-2-methylquinolin-4-amine Chemical compound C1=CC2=NC(C)=CC(N)=C2C=C1C(N1N)N=C(C=2C=C3C(N)=CC(C)=NC3=CC=2)N=C1OC1=CC=NC=C1 ZSCKZGZVIVDZIH-UHFFFAOYSA-N 0.000 claims 1
- UNKZQAAIYDJZKA-UHFFFAOYSA-N 6-[1-amino-4-[4-(dimethylamino)-2-methylquinolin-6-yl]-6-(1-methylpiperidin-4-yl)-2h-1,3,5-triazin-2-yl]-n,n,2-trimethylquinolin-4-amine Chemical compound C1=C2C(N(C)C)=CC(C)=NC2=CC=C1C(N1N)N=C(C=2C=C3C(N(C)C)=CC(C)=NC3=CC=2)N=C1C1CCN(C)CC1 UNKZQAAIYDJZKA-UHFFFAOYSA-N 0.000 claims 1
- CREAUNICNJGPFA-UHFFFAOYSA-N 6-[1-amino-4-[4-(dimethylamino)-2-methylquinolin-6-yl]-6-(4-piperidin-4-ylpiperazin-1-yl)-2h-1,3,5-triazin-2-yl]-n,n,2-trimethylquinolin-4-amine Chemical compound C1=C2C(N(C)C)=CC(C)=NC2=CC=C1C(N1N)N=C(C=2C=C3C(N(C)C)=CC(C)=NC3=CC=2)N=C1N(CC1)CCN1C1CCNCC1 CREAUNICNJGPFA-UHFFFAOYSA-N 0.000 claims 1
- VPAQLNJLEWUGOL-UAJNXHJVSA-N 6-[1-amino-4-[4-(dimethylamino)-2-methylquinolin-6-yl]-6-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]-2h-1,3,5-triazin-2-yl]-n,n,2-trimethylquinolin-4-amine Chemical compound C([C@@H]1CCCN1C1=NC(=NC(N1N)C1=CC=C2N=C(C)C=C(C2=C1)N(C)C)C=1C=C2C(N(C)C)=CC(C)=NC2=CC=1)N1CCCC1 VPAQLNJLEWUGOL-UAJNXHJVSA-N 0.000 claims 1
- LOQNQDGUHXZQDT-UHFFFAOYSA-N 6-[1-amino-4-[4-(dimethylamino)-2-methylquinolin-6-yl]-6-[4-[2-(dipropylamino)ethyl]piperazin-1-yl]-2h-1,3,5-triazin-2-yl]-n,n,2-trimethylquinolin-4-amine Chemical compound C1CN(CCN(CCC)CCC)CCN1C1=NC(C=2C=C3C(N(C)C)=CC(C)=NC3=CC=2)=NC(C=2C=C3C(N(C)C)=CC(C)=NC3=CC=2)N1N LOQNQDGUHXZQDT-UHFFFAOYSA-N 0.000 claims 1
- BVNZWVRSCSDVQW-UHFFFAOYSA-N 6-[1-amino-4-[4-(dimethylamino)-2-methylquinolin-6-yl]-6-phenyl-2h-1,3,5-triazin-2-yl]-n,n,2-trimethylquinolin-4-amine Chemical compound C1=C2C(N(C)C)=CC(C)=NC2=CC=C1C(N1N)N=C(C=2C=C3C(N(C)C)=CC(C)=NC3=CC=2)N=C1C1=CC=CC=C1 BVNZWVRSCSDVQW-UHFFFAOYSA-N 0.000 claims 1
- YCGMZDNRCSBINU-UHFFFAOYSA-N 6-[1-amino-4-[4-(dimethylamino)-2-methylquinolin-6-yl]-6-pyridin-4-yloxy-2h-1,3,5-triazin-2-yl]-n,n,2-trimethylquinolin-4-amine Chemical compound C1=C2C(N(C)C)=CC(C)=NC2=CC=C1C(N1N)N=C(C=2C=C3C(N(C)C)=CC(C)=NC3=CC=2)N=C1OC1=CC=NC=C1 YCGMZDNRCSBINU-UHFFFAOYSA-N 0.000 claims 1
- 108010024976 Asparaginase Proteins 0.000 claims 1
- AHKGASQNMBSMMV-UHFFFAOYSA-N CN(C1=CC(=NC2=CC=C(C=C12)C1N(C(=NC(=N1)C=1C=C2C(=CC(=NC2=CC1)C)N(C)C)C1=CC=NC=C1)N(C)N)C)C Chemical compound CN(C1=CC(=NC2=CC=C(C=C12)C1N(C(=NC(=N1)C=1C=C2C(=CC(=NC2=CC1)C)N(C)C)C1=CC=NC=C1)N(C)N)C)C AHKGASQNMBSMMV-UHFFFAOYSA-N 0.000 claims 1
- YDURJGCAZNKCIC-UHFFFAOYSA-N CN(C1=CC(=NC2=CC=C(C=C12)C1N(C(=NC(=N1)C=1C=C2C(=CC(=NC2=CC=1)C)N(C)C)CCCCN1CCCCC1)NN)C)C Chemical compound CN(C1=CC(=NC2=CC=C(C=C12)C1N(C(=NC(=N1)C=1C=C2C(=CC(=NC2=CC=1)C)N(C)C)CCCCN1CCCCC1)NN)C)C YDURJGCAZNKCIC-UHFFFAOYSA-N 0.000 claims 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 108020004414 DNA Proteins 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- FVLQBWIJLZPMNG-UHFFFAOYSA-N NC1=CC(=NC2=CC=C(C=C12)C1N(C(=NC(=N1)C=1C=C2C(=CC(=NC2=CC=1)C)N)C1CN2CCC1CC2)NN)C Chemical compound NC1=CC(=NC2=CC=C(C=C12)C1N(C(=NC(=N1)C=1C=C2C(=CC(=NC2=CC=1)C)N)C1CN2CCC1CC2)NN)C FVLQBWIJLZPMNG-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 108010017842 Telomerase Proteins 0.000 claims 1
- 101710183280 Topoisomerase Proteins 0.000 claims 1
- 150000003838 adenosines Chemical class 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims 1
- JKOQGQFVAUAYPM-UHFFFAOYSA-N amifostine Chemical compound NCCCNCCSP(O)(O)=O JKOQGQFVAUAYPM-UHFFFAOYSA-N 0.000 claims 1
- 229960001097 amifostine Drugs 0.000 claims 1
- 239000003098 androgen Substances 0.000 claims 1
- 229940045799 anthracyclines and related substance Drugs 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 229940044684 anti-microtubule agent Drugs 0.000 claims 1
- 229940088710 antibiotic agent Drugs 0.000 claims 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical class O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940088598 enzyme Drugs 0.000 claims 1
- 230000012173 estrus Effects 0.000 claims 1
- 150000005699 fluoropyrimidines Chemical class 0.000 claims 1
- 229940022353 herceptin Drugs 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims 1
- 229960004768 irinotecan Drugs 0.000 claims 1
- 150000002537 isoquinolines Chemical group 0.000 claims 1
- 125000001288 lysyl group Chemical group 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 150000003057 platinum Chemical class 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 229930002330 retinoic acid Natural products 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 229960005314 suramin Drugs 0.000 claims 1
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 claims 1
- 108091035539 telomere Proteins 0.000 claims 1
- 102000055501 telomere Human genes 0.000 claims 1
- 210000003411 telomere Anatomy 0.000 claims 1
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims 1
- 229960000303 topotecan Drugs 0.000 claims 1
- 238000011282 treatment Methods 0.000 claims 1
- 229960001727 tretinoin Drugs 0.000 claims 1
- 239000004066 vascular targeting agent Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0103916A FR2822468B1 (fr) | 2001-03-23 | 2001-03-23 | Derives chimiques et leur application comme agent anti-telomerase |
| FR0110370 | 2001-08-02 | ||
| PCT/FR2002/001005 WO2002076975A1 (fr) | 2001-03-23 | 2002-03-22 | Derives chimiques et leur application comme agent antitelomerase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004524349A JP2004524349A (ja) | 2004-08-12 |
| JP2004524349A5 true JP2004524349A5 (enrdf_load_stackoverflow) | 2005-12-22 |
Family
ID=26212933
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| Application Number | Title | Priority Date | Filing Date |
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| JP2002576233A Ceased JP2004524349A (ja) | 2001-03-23 | 2002-03-22 | 化学的誘導体および抗テロメラーゼ剤としてのその使用 |
Country Status (11)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004534046A (ja) | 2001-05-28 | 2004-11-11 | アベンティス・ファーマ・ソシエテ・アノニム | 化学誘導体および抗テロメラーゼ剤としてのその使用 |
| US7173032B2 (en) * | 2001-09-21 | 2007-02-06 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
| AU2002361846A1 (en) * | 2001-12-21 | 2003-07-15 | Bayer Pharmaceuticals Corporation | Quinazoline and quinoline derivative compounds as inhibitors of prolylpeptidase, inducers of apoptosis and cancer treatment agents |
| WO2004001018A2 (en) * | 2002-06-25 | 2003-12-31 | The Center For Blood Research, Inc. | Vacuolins |
| FR2850970B1 (fr) * | 2003-02-07 | 2006-07-07 | Aventis Pharma Sa | Derives chimiques se liant de maniere tres specifique aux structures d'adn en g-quadruplexe et leur application comme agent anticancereux specifique |
| US8309562B2 (en) | 2003-07-03 | 2012-11-13 | Myrexis, Inc. | Compounds and therapeutical use thereof |
| WO2006074147A2 (en) | 2005-01-03 | 2006-07-13 | Myriad Genetics, Inc. | Nitrogen containing bicyclic compounds and therapeutical use thereof |
| CA2531327A1 (en) | 2003-07-03 | 2005-01-13 | Myriad Genetics, Inc. | Compounds and therapeutical use thereof |
| US8258145B2 (en) | 2005-01-03 | 2012-09-04 | Myrexis, Inc. | Method of treating brain cancer |
| NZ563245A (en) * | 2005-05-19 | 2011-04-29 | Prometic Biosciences Inc | Triazine compounds and compositions thereof for the treatment of cancers |
| JP2009545592A (ja) * | 2006-07-31 | 2009-12-24 | プリーシス・ファーマシューティカルズ・インコーポレイテッド | コード化小分子ライブラリーからのオーロラキナーゼ阻害剤 |
| JP5282091B2 (ja) * | 2007-07-25 | 2013-09-04 | ブリストル−マイヤーズ スクイブ カンパニー | トリアジンキナーゼ阻害剤 |
| FR2948686B1 (fr) * | 2009-07-30 | 2011-08-19 | Biomerieux Sa | Nouveaux substrats de peptidase |
| JP7284518B2 (ja) * | 2018-03-20 | 2023-05-31 | 国立大学法人広島大学 | テロメア結合タンパク質を阻害する化合物、及びそれを含むテロメア結合タンパク質阻害剤 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9206768D0 (en) * | 1992-03-27 | 1992-05-13 | Jarman Michael | New compounds for use in the treatment of cancer |
| JPH1160573A (ja) * | 1997-08-22 | 1999-03-02 | Nippon Kayaku Co Ltd | トリアジン誘導体及びテロメラーゼ阻害剤 |
| US6262053B1 (en) * | 1999-06-23 | 2001-07-17 | Parker Hughes Institute | Melamine derivatives as potent anti-cancer agents |
| CA2392507A1 (fr) * | 1999-11-29 | 2001-06-07 | Aventis Pharma S.A. | Derives arylamines et leur application comme agent antitelomerase |
| EP1479397B1 (en) * | 2002-02-05 | 2011-06-08 | Astellas Pharma Inc. | 2,4,6-triamino-1,3,5-triazine derivative |
-
2002
- 2002-03-21 CO CO02025874A patent/CO5380035A1/es not_active Application Discontinuation
- 2002-03-22 MX MXPA03008269A patent/MXPA03008269A/es not_active Application Discontinuation
- 2002-03-22 AU AU2002251140A patent/AU2002251140B2/en not_active Ceased
- 2002-03-22 EP EP02720068A patent/EP1373252A1/fr not_active Withdrawn
- 2002-03-22 WO PCT/FR2002/001005 patent/WO2002076975A1/fr active IP Right Grant
- 2002-03-22 PE PE2002000227A patent/PE20020959A1/es not_active Application Discontinuation
- 2002-03-22 MY MYPI20021036A patent/MY130957A/en unknown
- 2002-03-22 CA CA002442012A patent/CA2442012A1/fr not_active Abandoned
- 2002-03-22 AR ARP020101060A patent/AR034297A1/es unknown
- 2002-03-22 IL IL15805602A patent/IL158056A0/xx unknown
- 2002-03-22 JP JP2002576233A patent/JP2004524349A/ja not_active Ceased
-
2003
- 2003-09-22 IL IL158056A patent/IL158056A/en not_active IP Right Cessation
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