MXPA06000216A - Producto que comprende por lo menos un inhibidor de cdc25 fosfatasa en combinacion con al menos algun otro agente anti-cancer. - Google Patents
Producto que comprende por lo menos un inhibidor de cdc25 fosfatasa en combinacion con al menos algun otro agente anti-cancer.Info
- Publication number
- MXPA06000216A MXPA06000216A MXPA06000216A MXPA06000216A MXPA06000216A MX PA06000216 A MXPA06000216 A MX PA06000216A MX PA06000216 A MXPA06000216 A MX PA06000216A MX PA06000216 A MXPA06000216 A MX PA06000216A MX PA06000216 A MXPA06000216 A MX PA06000216A
- Authority
- MX
- Mexico
- Prior art keywords
- radical
- alkyl
- radicals
- amino
- independently
- Prior art date
Links
- 229940127084 other anti-cancer agent Drugs 0.000 title claims abstract description 11
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 title abstract description 13
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 title abstract description 13
- WFRKJMRGXGWHBM-UHFFFAOYSA-M sodium;octyl sulfate Chemical compound [Na+].CCCCCCCCOS([O-])(=O)=O WFRKJMRGXGWHBM-UHFFFAOYSA-M 0.000 title abstract description 3
- -1 {(2R) -2-amino--3 -[(8S)-8 -(cyclohexylmethyl) -2-phenyl-5, 6-dihydroimidazo [1, 2-a]pyrazin- 7(8H)-yl] --3-oxopropyl} dithio Chemical group 0.000 claims abstract description 500
- 150000001875 compounds Chemical class 0.000 claims abstract description 253
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 93
- 150000003839 salts Chemical class 0.000 claims abstract description 60
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 47
- 239000003112 inhibitor Substances 0.000 claims abstract description 27
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 13
- 201000011510 cancer Diseases 0.000 claims abstract description 10
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims abstract description 9
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 7
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229940127093 camptothecin Drugs 0.000 claims abstract description 6
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003528 protein farnesyltransferase inhibitor Substances 0.000 claims abstract description 6
- 230000026683 transduction Effects 0.000 claims abstract description 5
- 238000010361 transduction Methods 0.000 claims abstract description 5
- 230000006820 DNA synthesis Effects 0.000 claims abstract description 3
- 108010006731 Dimethylallyltranstransferase Proteins 0.000 claims abstract description 3
- 102000005454 Dimethylallyltranstransferase Human genes 0.000 claims abstract description 3
- 239000002168 alkylating agent Substances 0.000 claims abstract description 3
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 3
- 210000004292 cytoskeleton Anatomy 0.000 claims abstract description 3
- 101710183280 Topoisomerase Proteins 0.000 claims abstract 2
- 102000034345 heterotrimeric G proteins Human genes 0.000 claims abstract 2
- 108091006093 heterotrimeric G proteins Proteins 0.000 claims abstract 2
- 150000003254 radicals Chemical class 0.000 claims description 234
- 125000000217 alkyl group Chemical group 0.000 claims description 182
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 155
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 143
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 105
- 125000005843 halogen group Chemical group 0.000 claims description 101
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 91
- 125000000623 heterocyclic group Chemical group 0.000 claims description 90
- 125000003118 aryl group Chemical group 0.000 claims description 73
- 125000001424 substituent group Chemical group 0.000 claims description 67
- 102000007588 cdc25 Phosphatases Human genes 0.000 claims description 65
- 108010046616 cdc25 Phosphatases Proteins 0.000 claims description 65
- 125000003545 alkoxy group Chemical group 0.000 claims description 58
- 125000001188 haloalkyl group Chemical group 0.000 claims description 52
- 210000004027 cell Anatomy 0.000 claims description 51
- 229940122907 Phosphatase inhibitor Drugs 0.000 claims description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
- 125000005842 heteroatom Chemical group 0.000 claims description 31
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 22
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 19
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 16
- 150000005840 aryl radicals Chemical class 0.000 claims description 15
- 125000003282 alkyl amino group Chemical group 0.000 claims description 14
- 125000002837 carbocyclic group Chemical group 0.000 claims description 14
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 13
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 13
- 241001024304 Mino Species 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 230000000295 complement effect Effects 0.000 claims description 11
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 10
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 9
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 8
- 150000001721 carbon Chemical class 0.000 claims description 8
- MJVAVZPDRWSRRC-UHFFFAOYSA-N vitamin K3 Natural products C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 239000003534 dna topoisomerase inhibitor Substances 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- BTIHMVBBUGXLCJ-OAHLLOKOSA-N seliciclib Chemical group C=12N=CN(C(C)C)C2=NC(N[C@@H](CO)CC)=NC=1NCC1=CC=CC=C1 BTIHMVBBUGXLCJ-OAHLLOKOSA-N 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
- 229940044693 topoisomerase inhibitor Drugs 0.000 claims description 4
- 235000012711 vitamin K3 Nutrition 0.000 claims description 4
- 239000011652 vitamin K3 Substances 0.000 claims description 4
- 229940041603 vitamin k 3 Drugs 0.000 claims description 4
- SGAOXTHFXVLOBH-KRWDZBQOSA-N (8s)-8-(cyclohexylmethyl)-2-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine Chemical compound C([C@H]1C2=NC(=CN2CCN1)C=1C=CC=CC=1)C1CCCCC1 SGAOXTHFXVLOBH-KRWDZBQOSA-N 0.000 claims description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
- 108091006027 G proteins Proteins 0.000 claims description 3
- 102000030782 GTP binding Human genes 0.000 claims description 3
- 108091000058 GTP-Binding Proteins 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 3
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 3
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000003880 polar aprotic solvent Substances 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 101100509371 Arabidopsis thaliana CHR11 gene Proteins 0.000 claims description 2
- 102000016736 Cyclin Human genes 0.000 claims description 2
- 108050006400 Cyclin Proteins 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- LFMFPKKYRXFHHZ-UHFFFAOYSA-N R24 Chemical group C1=C(Cl)C(C)=CC=C1NC1=NC(N)=C(C=CC=C2)C2=N1 LFMFPKKYRXFHHZ-UHFFFAOYSA-N 0.000 claims description 2
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000002785 azepinyl group Chemical group 0.000 claims description 2
- 125000005335 azido alkyl group Chemical group 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 230000032823 cell division Effects 0.000 claims description 2
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 2
- 239000000539 dimer Substances 0.000 claims description 2
- 150000002019 disulfides Chemical class 0.000 claims description 2
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 2
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 2
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 2
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000004589 thienofuryl group Chemical group O1C(=CC2=C1C=CS2)* 0.000 claims description 2
- 125000004587 thienothienyl group Chemical group S1C(=CC2=C1C=CS2)* 0.000 claims description 2
- 239000002875 cyclin dependent kinase inhibitor Substances 0.000 claims 4
- 229940124226 Farnesyltransferase inhibitor Drugs 0.000 claims 3
- 229940126074 CDK kinase inhibitor Drugs 0.000 claims 2
- 102100034770 Cyclin-dependent kinase inhibitor 3 Human genes 0.000 claims 2
- 101000945639 Homo sapiens Cyclin-dependent kinase inhibitor 3 Proteins 0.000 claims 2
- 229940121659 Prenyltransferase inhibitor Drugs 0.000 claims 2
- 125000006088 2-oxoazepinyl group Chemical group 0.000 claims 1
- 125000004638 2-oxopiperazinyl group Chemical group O=C1N(CCNC1)* 0.000 claims 1
- 125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 0.000 claims 1
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims 1
- 125000004600 benzothiopyranyl group Chemical group S1C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004597 dihydrobenzothiopyranyl group Chemical group S1C(CCC2=C1C=CC=C2)* 0.000 claims 1
- WOKPSXJEBSRSAT-UHFFFAOYSA-N dihydrobenzothiopyranyl sulfone group Chemical group S1C(CCC2=C1C=CC=C2)S(=O)(=O)C2SC1=C(CC2)C=CC=C1 WOKPSXJEBSRSAT-UHFFFAOYSA-N 0.000 claims 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 claims 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims 1
- 229940043355 kinase inhibitor Drugs 0.000 claims 1
- MZAVPBQCWWIYEQ-UHFFFAOYSA-N n-(6-chloro-1,3-benzothiazol-2-yl)-1-benzothiophene-2-sulfonamide Chemical group C1=CC=C2SC(S(=O)(=O)NC3=NC4=CC=C(C=C4S3)Cl)=CC2=C1 MZAVPBQCWWIYEQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
- 125000006089 thiamorpholinyl sulfoxide group Chemical group 0.000 claims 1
- 125000002769 thiazolinyl group Chemical group 0.000 claims 1
- 150000003716 vitamin K3 derivatives Chemical group 0.000 claims 1
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 abstract description 10
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 abstract description 10
- 102000003903 Cyclin-dependent kinases Human genes 0.000 abstract description 9
- 108090000266 Cyclin-dependent kinases Proteins 0.000 abstract description 9
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 abstract description 6
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 abstract description 5
- 229960004857 mitomycin Drugs 0.000 abstract description 5
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 abstract description 4
- 229960004316 cisplatin Drugs 0.000 abstract description 4
- 229960002949 fluorouracil Drugs 0.000 abstract description 4
- XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 abstract description 3
- 229960001220 amsacrine Drugs 0.000 abstract description 3
- 230000001413 cellular effect Effects 0.000 abstract description 3
- 229960004679 doxorubicin Drugs 0.000 abstract description 3
- 229960000485 methotrexate Drugs 0.000 abstract description 3
- 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 abstract description 3
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 abstract description 2
- 239000004052 folic acid antagonist Substances 0.000 abstract description 2
- 229960003048 vinblastine Drugs 0.000 abstract description 2
- 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 abstract description 2
- 239000000203 mixture Substances 0.000 description 159
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 138
- 238000005481 NMR spectroscopy Methods 0.000 description 97
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 73
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 71
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 67
- 239000000047 product Substances 0.000 description 65
- 239000000243 solution Substances 0.000 description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 238000002844 melting Methods 0.000 description 48
- 230000008018 melting Effects 0.000 description 48
- LOQLWFZHXKIBLK-UHFFFAOYSA-N 1,3-benzoxazole-2,4-dione Chemical group C1=CC(=O)C2=NC(=O)OC2=C1 LOQLWFZHXKIBLK-UHFFFAOYSA-N 0.000 description 46
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 36
- 238000012360 testing method Methods 0.000 description 36
- 239000000543 intermediate Substances 0.000 description 35
- 230000004663 cell proliferation Effects 0.000 description 32
- 239000000377 silicon dioxide Substances 0.000 description 32
- AFMPMSCZPVNPEM-UHFFFAOYSA-N 2-bromobenzonitrile Chemical compound BrC1=CC=CC=C1C#N AFMPMSCZPVNPEM-UHFFFAOYSA-N 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
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Classifications
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- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
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- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0307649A FR2856688B1 (fr) | 2003-06-25 | 2003-06-25 | PRODUIT COMPRENANT AU MOINS UN INHIBITEUR DE PHOSPHATASE CDc25 EN ASSOCIATION AVEC AU MOINS UN AUTRE AGENT ANTI-CANCEREUX |
| PCT/FR2004/001586 WO2005000852A2 (fr) | 2003-06-25 | 2004-06-24 | Produit comprenant au moins un inhibiteur de phosphates cdc25 en association avec au moins un autre agent anti-cancereux |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA06000216A true MXPA06000216A (es) | 2006-04-11 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| MXPA06000216A MXPA06000216A (es) | 2003-06-25 | 2004-06-24 | Producto que comprende por lo menos un inhibidor de cdc25 fosfatasa en combinacion con al menos algun otro agente anti-cancer. |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US20060281736A1 (enExample) |
| EP (3) | EP1792905A1 (enExample) |
| JP (2) | JP2007514639A (enExample) |
| AR (2) | AR044930A1 (enExample) |
| AT (1) | ATE439836T1 (enExample) |
| CA (1) | CA2530668A1 (enExample) |
| DE (1) | DE602004022674D1 (enExample) |
| DK (1) | DK1641453T3 (enExample) |
| ES (1) | ES2332137T3 (enExample) |
| FR (1) | FR2856688B1 (enExample) |
| MX (1) | MXPA06000216A (enExample) |
| MY (1) | MY141725A (enExample) |
| PL (1) | PL1641453T3 (enExample) |
| WO (1) | WO2005000852A2 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2834289B1 (fr) * | 2001-12-27 | 2004-03-19 | Sod Conseils Rech Applic | Derives de benzothiazole-4,7-diones et benzooxazole-4,7- diones, leur preparation et leurs applications therapeutiques |
| PT1461326E (pt) * | 2001-12-27 | 2007-10-16 | Sod Conseils Rech Applic | ''derivados de benzotiazole- e benzoxazole-4, 7- diona e sua utilização como inibidores de fosfatases cdc25'' |
| FR2856688B1 (fr) * | 2003-06-25 | 2008-05-30 | Sod Conseils Rech Applic | PRODUIT COMPRENANT AU MOINS UN INHIBITEUR DE PHOSPHATASE CDc25 EN ASSOCIATION AVEC AU MOINS UN AUTRE AGENT ANTI-CANCEREUX |
| DE10353792A1 (de) | 2003-11-13 | 2005-06-23 | Exner, Heinrich, Dr.med.vet. | Heil- und Wundsalbe auf der Basis einer wässrigen Emulsion |
| FR2877667B1 (fr) * | 2004-11-05 | 2007-03-23 | Sod Conseils Rech Applic | Derives de 4,7-dioxobenzothiazole-2-carboxamides, leur preparation et leurs applications therapeutiques |
| FR2879598B1 (fr) | 2004-12-17 | 2007-03-30 | Sod Conseils Rech Applic | Inhibiteurs de phosphatases cdc25 |
| FR2879460B1 (fr) * | 2004-12-17 | 2007-02-23 | Sod Conseils Rech Applic | Associations anti-douleur comprenant un derive de dihydroimidazopyrazine |
| US7723336B2 (en) | 2005-09-22 | 2010-05-25 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
| ATE510886T1 (de) * | 2007-09-06 | 2011-06-15 | Basf Se | Blends aus verzweigten polyarylethern und hydrophilen polymeren |
| CN101981033B (zh) | 2008-02-06 | 2015-02-04 | 百时美施贵宝公司 | 用作激酶抑制剂的取代的咪唑并哒嗪化合物 |
| AR077463A1 (es) | 2009-07-09 | 2011-08-31 | Irm Llc | Derivados de imidazo[1, 2 - a]pirazina y su uso en medicamentos para el tratamiento de enfermedades parasitarias |
| PL2786756T3 (pl) | 2010-11-12 | 2020-07-13 | Pharma Mar, S.A. | Terapia skojarzona z inhibitorem topoizomerazy |
| JP7377717B2 (ja) | 2017-04-24 | 2023-11-10 | ノバルティス アーゲー | ２－アミノ－ｌ－（２－（４－フルオロフェニル）－３－（４－フルオロフェニルアミノ）－８，８－ジメチル－５，６－ジヒドロイミダゾ［１，２－ａ］ピラジン－７（８ｈ）－イル）エタノン及びそれらの組み合わせの治療レジメン |
| WO2021067572A2 (en) * | 2019-10-01 | 2021-04-08 | United States Government As Represented By The Department Of Veterans Affairs | Compositions and methods for inhibiting carp-1 binding to nemo |
| JOP20220118A1 (ar) | 2019-11-21 | 2023-01-30 | Pharma Mar Sa | طرق لعلاج سرطان الرئة للخلايا الصغيرة بصيغ من لوربينيكتيدين |
| US11981645B1 (en) | 2023-10-10 | 2024-05-14 | King Faisal University | N′-(2-naphthoyloxy)-2-(benzo[d]oxazol-2-yl)acetimidamide as antimicrobial compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US735674A (en) * | 1902-01-29 | 1903-08-04 | William C Matthias | Sparking igniter for explosive-engines. |
| FR50000E (fr) | 1938-11-29 | 1939-09-29 | Moulin à café | |
| US5523430A (en) * | 1994-04-14 | 1996-06-04 | Bristol-Myers Squibb Company | Protein farnesyl transferase inhibitors |
| US6673927B2 (en) * | 1996-02-16 | 2004-01-06 | Societe De Conseils De Recherches Et D'applications Scientifiques, S.A.S. | Farnesyl transferase inhibitors |
| US6383871B1 (en) * | 1999-08-31 | 2002-05-07 | Micron Technology, Inc. | Method of forming multiple oxide thicknesses for merged memory and logic applications |
| RU2298417C2 (ru) * | 1999-11-09 | 2007-05-10 | Сосьете Де Консей Де Решерш Э Д`Аппликасьон Сьентифик (С.К.Р.А.С.) | Продукт, включающий ингибитор трансдукции сигналов гетеротримерных протеинов g в комбинации с другим цитостатическим средством, для терапевтического применения при лечении рака |
| FR2812198B1 (fr) * | 2000-07-28 | 2008-07-18 | Sod Conseils Rech Applic | DERIVES D'AMIDINES INHIBITEURS DE PHOSPHATASES cdc25 |
| WO2002050079A1 (fr) * | 2000-12-20 | 2002-06-27 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) | Inhibiteurs de kinases dependantes des cylines (cdk) et de la glycogene synthase kinase-3 (gsk-3) |
| FR2825278A1 (fr) * | 2001-05-30 | 2002-12-06 | Sod Conseils Rech Applic | Produit comprenant du mikanolide, du dihydromikanolide ou un analogue de ceux-ci en association avec un autre agent anti-cancereux pour une utilisation therapeutique dans le traitement du cancer |
| TW200304375A (en) * | 2001-12-06 | 2003-10-01 | Maxia Pharmaceuticals Inc | 2-Substituted thiazolidinone and oxazolidinone derivatives for the inhibition of phosphatases and the treatment of cancer |
| FR2834289B1 (fr) * | 2001-12-27 | 2004-03-19 | Sod Conseils Rech Applic | Derives de benzothiazole-4,7-diones et benzooxazole-4,7- diones, leur preparation et leurs applications therapeutiques |
| PT1461326E (pt) * | 2001-12-27 | 2007-10-16 | Sod Conseils Rech Applic | ''derivados de benzotiazole- e benzoxazole-4, 7- diona e sua utilização como inibidores de fosfatases cdc25'' |
| FR2856688B1 (fr) * | 2003-06-25 | 2008-05-30 | Sod Conseils Rech Applic | PRODUIT COMPRENANT AU MOINS UN INHIBITEUR DE PHOSPHATASE CDc25 EN ASSOCIATION AVEC AU MOINS UN AUTRE AGENT ANTI-CANCEREUX |
| FR2856686A1 (fr) * | 2003-06-25 | 2004-12-31 | Sod Conseils Rech Applic | Benzothiazole-4,7-diones et benzooxazole-4,7-diones substituees en position 5 ou 6 et leurs procedes de preparation |
| JP4273056B2 (ja) * | 2004-08-12 | 2009-06-03 | 不二越機械工業株式会社 | 研磨装置 |
-
2003
- 2003-06-25 FR FR0307649A patent/FR2856688B1/fr not_active Expired - Fee Related
-
2004
- 2004-06-17 MY MYPI20042361A patent/MY141725A/en unknown
- 2004-06-24 DK DK04767442T patent/DK1641453T3/da active
- 2004-06-24 EP EP07006144A patent/EP1792905A1/fr not_active Withdrawn
- 2004-06-24 AT AT04767442T patent/ATE439836T1/de not_active IP Right Cessation
- 2004-06-24 MX MXPA06000216A patent/MXPA06000216A/es active IP Right Grant
- 2004-06-24 JP JP2006516322A patent/JP2007514639A/ja active Pending
- 2004-06-24 WO PCT/FR2004/001586 patent/WO2005000852A2/fr not_active Ceased
- 2004-06-24 US US10/562,625 patent/US20060281736A1/en not_active Abandoned
- 2004-06-24 DE DE602004022674T patent/DE602004022674D1/de not_active Expired - Lifetime
- 2004-06-24 EP EP08020152A patent/EP2335702A1/fr not_active Withdrawn
- 2004-06-24 ES ES04767442T patent/ES2332137T3/es not_active Expired - Lifetime
- 2004-06-24 CA CA002530668A patent/CA2530668A1/fr not_active Abandoned
- 2004-06-24 EP EP04767442A patent/EP1641453B1/fr not_active Expired - Lifetime
- 2004-06-24 PL PL04767442T patent/PL1641453T3/pl unknown
- 2004-06-25 AR ARP040102257A patent/AR044930A1/es not_active Application Discontinuation
-
2008
- 2008-05-22 US US12/154,319 patent/US20090253685A1/en not_active Abandoned
- 2008-10-07 US US12/247,072 patent/US20090137596A1/en not_active Abandoned
-
2009
- 2009-03-09 AR ARP090100837A patent/AR070977A2/es unknown
- 2009-04-03 JP JP2009091214A patent/JP2009149694A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK1641453T3 (da) | 2009-12-14 |
| ES2332137T3 (es) | 2010-01-27 |
| AR070977A2 (es) | 2010-05-19 |
| US20060281736A1 (en) | 2006-12-14 |
| US20090137596A1 (en) | 2009-05-28 |
| US20090253685A1 (en) | 2009-10-08 |
| ATE439836T1 (de) | 2009-09-15 |
| JP2007514639A (ja) | 2007-06-07 |
| EP1641453A2 (fr) | 2006-04-05 |
| PL1641453T3 (pl) | 2010-01-29 |
| JP2009149694A (ja) | 2009-07-09 |
| WO2005000852A3 (fr) | 2005-06-30 |
| MY141725A (en) | 2010-06-15 |
| AR044930A1 (es) | 2005-10-12 |
| EP2335702A1 (fr) | 2011-06-22 |
| WO2005000852A2 (fr) | 2005-01-06 |
| EP1641453B1 (fr) | 2009-08-19 |
| DE602004022674D1 (de) | 2009-10-01 |
| CA2530668A1 (fr) | 2005-01-06 |
| FR2856688A1 (fr) | 2004-12-31 |
| FR2856688B1 (fr) | 2008-05-30 |
| EP1792905A1 (fr) | 2007-06-06 |
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