MXPA03008269A - Derivados quimicos y su aplicacion como agente antitelomerasa. - Google Patents
Derivados quimicos y su aplicacion como agente antitelomerasa.Info
- Publication number
- MXPA03008269A MXPA03008269A MXPA03008269A MXPA03008269A MXPA03008269A MX PA03008269 A MXPA03008269 A MX PA03008269A MX PA03008269 A MXPA03008269 A MX PA03008269A MX PA03008269 A MXPA03008269 A MX PA03008269A MX PA03008269 A MXPA03008269 A MX PA03008269A
- Authority
- MX
- Mexico
- Prior art keywords
- radical
- alkyl
- optionally substituted
- amino
- radicals
- Prior art date
Links
- 239000000126 substance Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 149
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 7
- -1 C1-C4 alkyl radical Chemical class 0.000 claims description 466
- 150000003254 radicals Chemical class 0.000 claims description 255
- 125000000217 alkyl group Chemical group 0.000 claims description 242
- 239000001257 hydrogen Substances 0.000 claims description 92
- 229910052739 hydrogen Inorganic materials 0.000 claims description 92
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 90
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 75
- 229910052757 nitrogen Inorganic materials 0.000 claims description 64
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 53
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 47
- 125000003545 alkoxy group Chemical group 0.000 claims description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 37
- 125000004193 piperazinyl group Chemical group 0.000 claims description 29
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 29
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 27
- 125000005842 heteroatom Chemical group 0.000 claims description 27
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 26
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- 125000003282 alkyl amino group Chemical group 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 24
- 125000004076 pyridyl group Chemical group 0.000 claims description 23
- 125000005936 piperidyl group Chemical group 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000004434 sulfur atom Chemical group 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 18
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 108010017842 Telomerase Proteins 0.000 claims description 14
- 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 13
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000002619 bicyclic group Chemical group 0.000 claims description 11
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 claims description 11
- 229910052701 rubidium Inorganic materials 0.000 claims description 11
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 10
- 125000004450 alkenylene group Chemical group 0.000 claims description 10
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000003386 piperidinyl group Chemical group 0.000 claims description 10
- 125000005493 quinolyl group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 9
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims description 8
- XNMYNYSCEJBRPZ-UHFFFAOYSA-N 2-[(3-butyl-1-isoquinolinyl)oxy]-N,N-dimethylethanamine Chemical compound C1=CC=C2C(OCCN(C)C)=NC(CCCC)=CC2=C1 XNMYNYSCEJBRPZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000005237 alkyleneamino group Chemical group 0.000 claims description 8
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
- 238000004172 nitrogen cycle Methods 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 108091035539 telomere Proteins 0.000 claims description 5
- 102000055501 telomere Human genes 0.000 claims description 5
- 210000003411 telomere Anatomy 0.000 claims description 5
- 108020004414 DNA Proteins 0.000 claims description 4
- 108090000790 Enzymes Proteins 0.000 claims description 4
- 102000004190 Enzymes Human genes 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-O isoquinolin-2-ium Chemical compound C1=[NH+]C=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-O 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000003246 quinazolines Chemical class 0.000 claims description 3
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 101710183280 Topoisomerase Proteins 0.000 claims description 2
- 150000003838 adenosines Chemical class 0.000 claims description 2
- 230000001548 androgenic effect Effects 0.000 claims description 2
- 229940045799 anthracyclines and related substance Drugs 0.000 claims description 2
- 230000003115 biocidal effect Effects 0.000 claims description 2
- 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 description 2
- 150000005699 fluoropyrimidines Chemical class 0.000 claims description 2
- 229940022353 herceptin Drugs 0.000 claims description 2
- 239000005556 hormone Substances 0.000 claims description 2
- 229940088597 hormone Drugs 0.000 claims description 2
- 150000002537 isoquinolines Chemical class 0.000 claims description 2
- 210000004940 nucleus Anatomy 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 229940127557 pharmaceutical product Drugs 0.000 claims description 2
- 150000003057 platinum Chemical class 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 239000004066 vascular targeting agent Substances 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 40
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 23
- 125000002757 morpholinyl group Chemical group 0.000 claims 12
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 125000002883 imidazolyl group Chemical group 0.000 claims 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical compound NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 claims 4
- 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 4
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthalene Natural products C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 claims 4
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 claims 4
- 239000012964 benzotriazole Substances 0.000 claims 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- 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 3
- 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 3
- 230000001093 anti-cancer Effects 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 239000001301 oxygen 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
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-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
- 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 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-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
- 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 2
- HIUZQDBZKUCNDC-UHFFFAOYSA-N NC1=NC(=NC=N1)OC1=CC=NC=C1 Chemical compound NC1=NC(=NC=N1)OC1=CC=NC=C1 HIUZQDBZKUCNDC-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
- 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
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 2
- 125000005208 trialkylammonium group Chemical group 0.000 claims 2
- BMKDZUISNHGIBY-ZETCQYMHSA-N (+)-dexrazoxane Chemical compound C([C@H](C)N1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1 BMKDZUISNHGIBY-ZETCQYMHSA-N 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 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
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 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
- 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 1
- 108010024976 Asparaginase Proteins 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
- 229940044684 anti-microtubule 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
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 229960000605 dexrazoxane Drugs 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229940088598 enzyme Drugs 0.000 claims 1
- 229940011871 estrogen Drugs 0.000 claims 1
- 239000000262 estrogen Substances 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
- 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
- 150000003230 pyrimidines Chemical class 0.000 claims 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 229930002330 retinoic acid Natural products 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical group C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 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
- 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
- 229960001727 tretinoin Drugs 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 8
- 238000011275 oncology therapy Methods 0.000 abstract description 2
- 239000002246 antineoplastic agent Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 77
- 239000000243 solution Substances 0.000 description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- 239000000047 product Substances 0.000 description 58
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 44
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Classifications
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- 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 (1)
| Publication Number | Publication Date |
|---|---|
| MXPA03008269A true MXPA03008269A (es) | 2004-10-15 |
Family
ID=26212933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA03008269A MXPA03008269A (es) | 2001-03-23 | 2002-03-22 | Derivados quimicos y su aplicacion como agente antitelomerasa. |
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) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2002314252A1 (en) * | 2001-05-28 | 2002-12-09 | Aventis Pharma S.A. | Chemical derivatives and the use thereof as an anti-telomerase agent |
| 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 |
| CA2608463C (en) * | 2005-05-19 | 2015-02-03 | Prometic Biosciences Inc. | Compounds, compositions containing such compounds, and methods of treatment of metastatic melanoma and other cancers |
| EP2046763A2 (en) * | 2006-07-31 | 2009-04-15 | Praecis Pharmaceuticals Incorporated | Aurora kinase inhibitors from an encoded small molecule library |
| KR20100038108A (ko) * | 2007-07-25 | 2010-04-12 | 브리스톨-마이어스 스큅 컴퍼니 | 트리아진 키나제 억제제 |
| FR2948686B1 (fr) * | 2009-07-30 | 2011-08-19 | Biomerieux Sa | Nouveaux substrats de peptidase |
| US20210024455A1 (en) * | 2018-03-20 | 2021-01-28 | Hiroshima University | Compound which inhibits telomere-binding protein, and telomere-binding protein inhibitor containing same |
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 |
| IL149402A0 (en) * | 1999-11-29 | 2002-11-10 | Aventis Pharma Sa | Arylamine derivatives and their use as anti-telomerase agent |
| AU2003244463A1 (en) * | 2002-02-05 | 2003-09-02 | Yamanouchi Pharmaceutical Co., Ltd. | 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 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
Also Published As
| Publication number | Publication date |
|---|---|
| IL158056A0 (en) | 2004-03-28 |
| IL158056A (en) | 2010-02-17 |
| JP2004524349A (ja) | 2004-08-12 |
| AU2002251140B2 (en) | 2007-03-15 |
| AR034297A1 (es) | 2004-02-18 |
| MY130957A (en) | 2007-07-31 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |