JP2004524349A - 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 - Google Patents
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 Download PDFInfo
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- JP2004524349A JP2004524349A JP2002576233A JP2002576233A JP2004524349A JP 2004524349 A JP2004524349 A JP 2004524349A JP 2002576233 A JP2002576233 A JP 2002576233A JP 2002576233 A JP2002576233 A JP 2002576233A JP 2004524349 A JP2004524349 A JP 2004524349A
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- 239000000126 substance Substances 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 140
- 238000011282 treatment Methods 0.000 claims abstract description 8
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 7
- -1 homopiperazinyl group Chemical group 0.000 claims description 313
- 125000000217 alkyl group Chemical group 0.000 claims description 298
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 161
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 101
- 229910052739 hydrogen Inorganic materials 0.000 claims description 94
- 239000001257 hydrogen Substances 0.000 claims description 93
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 91
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 85
- 125000005936 piperidyl group Chemical group 0.000 claims description 83
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 80
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 78
- 125000004193 piperazinyl group Chemical group 0.000 claims description 74
- 125000004076 pyridyl group Chemical group 0.000 claims description 70
- 229910052757 nitrogen Chemical group 0.000 claims description 68
- 125000003118 aryl group Chemical group 0.000 claims description 62
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 62
- 125000002757 morpholinyl group Chemical group 0.000 claims description 54
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 52
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 52
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 51
- 125000003545 alkoxy group Chemical group 0.000 claims description 48
- 125000003282 alkyl amino group Chemical group 0.000 claims description 46
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 42
- 125000003277 amino group Chemical group 0.000 claims description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 42
- 125000005842 heteroatom Chemical group 0.000 claims description 34
- AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 229910052717 sulfur Inorganic materials 0.000 claims description 32
- 125000001624 naphthyl group Chemical group 0.000 claims description 30
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 28
- 125000003386 piperidinyl group Chemical group 0.000 claims description 27
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical group C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims description 27
- 125000005843 halogen group Chemical class 0.000 claims description 26
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 23
- 125000002619 bicyclic group Chemical group 0.000 claims description 22
- 125000002950 monocyclic group Chemical group 0.000 claims description 22
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical class COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 21
- 125000004434 sulfur atom Chemical group 0.000 claims description 21
- 125000002252 acyl group Chemical group 0.000 claims description 20
- 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 description 18
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical class NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
- 108010017842 Telomerase Proteins 0.000 claims description 17
- 125000004442 acylamino group Chemical group 0.000 claims description 17
- 229910052705 radium Inorganic materials 0.000 claims description 17
- 229910052701 rubidium Inorganic materials 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 16
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 16
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 15
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 15
- 125000004450 alkenylene group Chemical group 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000002883 imidazolyl group Chemical group 0.000 claims description 14
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 125000005237 alkyleneamino group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 12
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 12
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 12
- 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 description 11
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 11
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000005493 quinolyl group Chemical group 0.000 claims description 11
- 125000000169 tricyclic heterocycle group Chemical group 0.000 claims description 11
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 10
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 10
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 10
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 10
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 claims description 10
- 108091035539 telomere Proteins 0.000 claims description 10
- 102000055501 telomere Human genes 0.000 claims description 10
- 210000003411 telomere Anatomy 0.000 claims description 10
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 9
- 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 description 9
- 108091081406 G-quadruplex Proteins 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 7
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 238000000638 solvent extraction Methods 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 claims description 6
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 6
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical group C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 108020004414 DNA Proteins 0.000 claims description 5
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
- 125000004954 trialkylamino group Chemical group 0.000 claims description 5
- 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 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 108090000790 Enzymes Proteins 0.000 claims description 4
- 102000004190 Enzymes Human genes 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 229940088598 enzyme Drugs 0.000 claims description 4
- 125000006542 morpholinylalkyl group Chemical group 0.000 claims description 4
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
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- CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical compound C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- 102000053632 repetitive DNA sequence Human genes 0.000 description 1
- 108091035233 repetitive DNA sequence Proteins 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 229960003440 semustine Drugs 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012475 sodium chloride buffer Substances 0.000 description 1
- IHQKEDIOMGYHEB-UHFFFAOYSA-M sodium dimethylarsinate Chemical compound [Na+].C[As](C)([O-])=O IHQKEDIOMGYHEB-UHFFFAOYSA-M 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 210000001082 somatic cell Anatomy 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229960001052 streptozocin Drugs 0.000 description 1
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 239000003277 telomerase inhibitor Substances 0.000 description 1
- 229960004964 temozolomide Drugs 0.000 description 1
- NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
- 229960001278 teniposide Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229960001196 thiotepa Drugs 0.000 description 1
- 229960003087 tioguanine Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LHJCZOXMCGQVDQ-UHFFFAOYSA-N tri(propan-2-yl)silyl trifluoromethanesulfonate Chemical compound CC(C)[Si](C(C)C)(C(C)C)OS(=O)(=O)C(F)(F)F LHJCZOXMCGQVDQ-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- HHJUWIANJFBDHT-KOTLKJBCSA-N vindesine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(N)=O)N4C)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 HHJUWIANJFBDHT-KOTLKJBCSA-N 0.000 description 1
- 229960004355 vindesine Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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 true JP2004524349A (ja) | 2004-08-12 |
| JP2004524349A5 JP2004524349A5 (enExample) | 2005-12-22 |
Family
ID=26212933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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)
| Country | Link |
|---|---|
| EP (1) | EP1373252A1 (enExample) |
| JP (1) | JP2004524349A (enExample) |
| AR (1) | AR034297A1 (enExample) |
| AU (1) | AU2002251140B2 (enExample) |
| CA (1) | CA2442012A1 (enExample) |
| CO (1) | CO5380035A1 (enExample) |
| IL (2) | IL158056A0 (enExample) |
| MX (1) | MXPA03008269A (enExample) |
| MY (1) | MY130957A (enExample) |
| PE (1) | PE20020959A1 (enExample) |
| WO (1) | WO2002076975A1 (enExample) |
Cited By (6)
| 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 |
| JP2008540585A (ja) * | 2005-05-19 | 2008-11-20 | プロメティック・バイオサイエンスィズ・インコーポレーテッド | 転移性メラノーマ及び他の癌を治療するための化合物、そのような化合物を含有する組成物、および治療方法 |
| 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 |
| JP2010534677A (ja) * | 2007-07-25 | 2010-11-11 | 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 |
| JP2013500036A (ja) * | 2009-07-30 | 2013-01-07 | ビオメリュー | 新規ペプチダーゼ基質 |
| WO2019181714A1 (ja) * | 2018-03-20 | 2019-09-26 | 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 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| AU2004253967B2 (en) | 2003-07-03 | 2010-02-18 | Cytovia, Inc. | 4-arylamino-quinazolines as activators of caspases and inducers of apoptosis |
| US8309562B2 (en) | 2003-07-03 | 2012-11-13 | Myrexis, Inc. | Compounds and therapeutical use thereof |
| EP1833482A4 (en) | 2005-01-03 | 2011-02-16 | Myriad Genetics Inc | COMPOUNDS AND ITS THERAPEUTIC USE |
| US8258145B2 (en) | 2005-01-03 | 2012-09-04 | Myrexis, Inc. | Method of treating brain cancer |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2003066099A1 (en) * | 2002-02-05 | 2003-08-14 | Yamanouchi Pharmaceutical Co., Ltd. | 2,4,6-triamino-1,3,5-triazine derivative |
Family Cites Families (3)
| 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 |
| US6262053B1 (en) * | 1999-06-23 | 2001-07-17 | Parker Hughes Institute | Melamine derivatives as potent anti-cancer agents |
| IL149402A0 (en) * | 1999-11-29 | 2002-11-10 | Aventis Pharma Sa | Arylamine derivatives and their use as anti-telomerase agent |
-
2002
- 2002-03-21 CO CO02025874A patent/CO5380035A1/es not_active Application Discontinuation
- 2002-03-22 AR ARP020101060A patent/AR034297A1/es unknown
- 2002-03-22 CA CA002442012A patent/CA2442012A1/fr not_active Abandoned
- 2002-03-22 WO PCT/FR2002/001005 patent/WO2002076975A1/fr not_active Ceased
- 2002-03-22 IL IL15805602A patent/IL158056A0/xx unknown
- 2002-03-22 JP JP2002576233A patent/JP2004524349A/ja not_active Ceased
- 2002-03-22 PE PE2002000227A patent/PE20020959A1/es not_active Application Discontinuation
- 2002-03-22 AU AU2002251140A patent/AU2002251140B2/en not_active Ceased
- 2002-03-22 MX MXPA03008269A patent/MXPA03008269A/es not_active Application Discontinuation
- 2002-03-22 MY MYPI20021036A patent/MY130957A/en unknown
- 2002-03-22 EP EP02720068A patent/EP1373252A1/fr not_active Withdrawn
-
2003
- 2003-09-22 IL IL158056A patent/IL158056A/en not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2003066099A1 (en) * | 2002-02-05 | 2003-08-14 | Yamanouchi Pharmaceutical Co., Ltd. | 2,4,6-triamino-1,3,5-triazine derivative |
Cited By (8)
| 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 |
| JP2008540585A (ja) * | 2005-05-19 | 2008-11-20 | プロメティック・バイオサイエンスィズ・インコーポレーテッド | 転移性メラノーマ及び他の癌を治療するための化合物、そのような化合物を含有する組成物、および治療方法 |
| 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 |
| JP2010534677A (ja) * | 2007-07-25 | 2010-11-11 | 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 |
| JP2013500036A (ja) * | 2009-07-30 | 2013-01-07 | ビオメリュー | 新規ペプチダーゼ基質 |
| WO2019181714A1 (ja) * | 2018-03-20 | 2019-09-26 | 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 |
| JPWO2019181714A1 (ja) * | 2018-03-20 | 2021-04-08 | 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 |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| IL158056A0 (en) | 2004-03-28 |
| IL158056A (en) | 2010-02-17 |
| AU2002251140B2 (en) | 2007-03-15 |
| AR034297A1 (es) | 2004-02-18 |
| MY130957A (en) | 2007-07-31 |
| MXPA03008269A (es) | 2004-10-15 |
| PE20020959A1 (es) | 2002-12-17 |
| CA2442012A1 (fr) | 2002-10-03 |
| EP1373252A1 (fr) | 2004-01-02 |
| CO5380035A1 (es) | 2004-03-31 |
| WO2002076975A1 (fr) | 2002-10-03 |
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