CA2530668A1 - Produit comprenant au moins un inhibiteur de phosphatase cdc25 en association avec au moins un autre agent anti-cancereux - Google Patents
Produit comprenant au moins un inhibiteur de phosphatase cdc25 en association avec au moins un autre agent anti-cancereux Download PDFInfo
- Publication number
- CA2530668A1 CA2530668A1 CA002530668A CA2530668A CA2530668A1 CA 2530668 A1 CA2530668 A1 CA 2530668A1 CA 002530668 A CA002530668 A CA 002530668A CA 2530668 A CA2530668 A CA 2530668A CA 2530668 A1 CA2530668 A1 CA 2530668A1
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- Prior art keywords
- radical
- alkyl
- independently
- radicals
- amino
- Prior art date
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- Abandoned
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- 229940127084 other anti-cancer agent Drugs 0.000 title claims abstract description 9
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 title claims description 21
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 title claims description 21
- WFRKJMRGXGWHBM-UHFFFAOYSA-M sodium;octyl sulfate Chemical compound [Na+].CCCCCCCCOS([O-])(=O)=O WFRKJMRGXGWHBM-UHFFFAOYSA-M 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 245
- 150000003839 salts Chemical class 0.000 claims abstract description 62
- 102000007588 cdc25 Phosphatases Human genes 0.000 claims abstract description 56
- 108010046616 cdc25 Phosphatases Proteins 0.000 claims abstract description 56
- 239000003112 inhibitor Substances 0.000 claims abstract description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 41
- 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 abstract description 24
- 108091007914 CDKs Proteins 0.000 claims abstract description 13
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 12
- 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
- 201000011510 cancer Diseases 0.000 claims abstract description 9
- 230000001413 cellular 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
- 230000019491 signal transduction Effects 0.000 claims abstract description 6
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 6
- 101710183280 Topoisomerase Proteins 0.000 claims abstract description 5
- 102000034345 heterotrimeric G proteins Human genes 0.000 claims abstract description 4
- 108091006093 heterotrimeric G proteins Proteins 0.000 claims abstract description 4
- 102000005454 Dimethylallyltranstransferase Human genes 0.000 claims abstract description 3
- 108010006731 Dimethylallyltranstransferase Proteins 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
- 230000032823 cell division Effects 0.000 claims abstract description 3
- 210000004292 cytoskeleton Anatomy 0.000 claims abstract description 3
- -1 alkoxyalkyl radical Chemical group 0.000 claims description 416
- 125000000217 alkyl group Chemical group 0.000 claims description 211
- 150000003254 radicals Chemical class 0.000 claims description 206
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 132
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 114
- 125000005843 halogen group Chemical group 0.000 claims description 98
- 125000000623 heterocyclic group Chemical group 0.000 claims description 93
- 125000003118 aryl group Chemical group 0.000 claims description 75
- 125000003545 alkoxy group Chemical group 0.000 claims description 72
- 125000001424 substituent group Chemical group 0.000 claims description 63
- 229940122907 Phosphatase inhibitor Drugs 0.000 claims description 49
- 229910052757 nitrogen Inorganic materials 0.000 claims description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 36
- 125000004429 atom Chemical group 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 32
- 125000001188 haloalkyl group Chemical group 0.000 claims description 30
- 125000005842 heteroatom Chemical group 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 20
- 150000005840 aryl radicals Chemical class 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000004414 alkyl thio group Chemical group 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 15
- 125000003282 alkyl amino group Chemical group 0.000 claims description 14
- 125000000392 cycloalkenyl 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
- 230000000295 complement effect Effects 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 10
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 10
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 230000001093 anti-cancer Effects 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- MJVAVZPDRWSRRC-UHFFFAOYSA-N vitamin K3 Natural products C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 claims description 9
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 8
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000002837 carbocyclic group Chemical group 0.000 claims description 8
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 8
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 claims description 7
- LFQCJSBXBZRMTN-OAQYLSRUSA-N diflomotecan Chemical compound CC[C@@]1(O)CC(=O)OCC(C2=O)=C1C=C1N2CC2=CC3=CC(F)=C(F)C=C3N=C21 LFQCJSBXBZRMTN-OAQYLSRUSA-N 0.000 claims description 7
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 108091000080 Phosphotransferase Proteins 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 5
- 102000020233 phosphotransferase Human genes 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 5
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 5
- 235000012711 vitamin K3 Nutrition 0.000 claims description 5
- 239000011652 vitamin K3 Substances 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 102000007317 Farnesyltranstransferase Human genes 0.000 claims description 4
- 108010007508 Farnesyltranstransferase Proteins 0.000 claims description 4
- SVSARCCKBMZNMR-UHFFFAOYSA-N [1-[2-[methyl-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethyl]amino]ethyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1CCN(C)CCN1C=CC(=C[NH+]=O)C=C1 SVSARCCKBMZNMR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 4
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 239000002798 polar solvent Substances 0.000 claims description 4
- BTIHMVBBUGXLCJ-OAHLLOKOSA-N seliciclib Chemical compound 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
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 229940041603 vitamin k 3 Drugs 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 102000016736 Cyclin Human genes 0.000 claims description 3
- 108050006400 Cyclin Proteins 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
- 230000001419 dependent effect Effects 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
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 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 2
- GNYQLPKGXMSQNY-UHFFFAOYSA-N 2-methyl-5-(2-piperidin-1-ylethylamino)-1,3-benzothiazole-4,7-dione Chemical compound S1C(C)=NC(C2=O)=C1C(=O)C=C2NCCN1CCCCC1 GNYQLPKGXMSQNY-UHFFFAOYSA-N 0.000 claims description 2
- LSDWHZYIIRIPCU-UHFFFAOYSA-N 2-methyl-5-(2-pyrrolidin-1-ylethylamino)-1,3-benzothiazole-4,7-dione Chemical compound S1C(C)=NC(C2=O)=C1C(=O)C=C2NCCN1CCCC1 LSDWHZYIIRIPCU-UHFFFAOYSA-N 0.000 claims description 2
- 125000006088 2-oxoazepinyl group Chemical group 0.000 claims description 2
- 125000004638 2-oxopiperazinyl group Chemical group O=C1N(CCNC1)* 0.000 claims description 2
- 125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 0.000 claims description 2
- MTUYOFGUEXWKLC-UHFFFAOYSA-N 5-[2-(dimethylamino)ethylamino]-2-methyl-1,3-benzothiazole-4,7-dione Chemical compound O=C1C(NCCN(C)C)=CC(=O)C2=C1N=C(C)S2 MTUYOFGUEXWKLC-UHFFFAOYSA-N 0.000 claims description 2
- 101100509371 Arabidopsis thaliana CHR11 gene Proteins 0.000 claims description 2
- 108091006027 G proteins Proteins 0.000 claims description 2
- 102000030782 GTP binding Human genes 0.000 claims description 2
- 108091000058 GTP-Binding Proteins 0.000 claims description 2
- LFMFPKKYRXFHHZ-UHFFFAOYSA-N R24 Chemical compound C1=C(Cl)C(C)=CC=C1NC1=NC(N)=C(C=CC=C2)C2=N1 LFMFPKKYRXFHHZ-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
- BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000005099 aryl alkyl carbonyl 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
- 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
- 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
- 125000004600 benzothiopyranyl group Chemical group S1C(C=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
- 229920001577 copolymer Chemical group 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 2
- 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004597 dihydrobenzothiopyranyl group Chemical group S1C(CCC2=C1C=CC=C2)* 0.000 claims description 2
- 239000000539 dimer Substances 0.000 claims description 2
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 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
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001786 isothiazolyl 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
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000005476 oxopyrrolidinyl 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
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000006089 thiamorpholinyl sulfoxide group Chemical group 0.000 claims description 2
- 125000002769 thiazolinyl 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
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 4
- 102000019337 Prenyltransferases Human genes 0.000 claims 2
- 108050006837 Prenyltransferases Proteins 0.000 claims 2
- WCUXJAHSNPROCI-UHFFFAOYSA-N 2-(2-chloro-6-fluorophenyl)-5-[2-(dimethylamino)ethylamino]-1,3-benzothiazole-4,7-dione Chemical compound N=1C=2C(=O)C(NCCN(C)C)=CC(=O)C=2SC=1C1=C(F)C=CC=C1Cl WCUXJAHSNPROCI-UHFFFAOYSA-N 0.000 claims 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims 1
- 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 claims 1
- 150000002019 disulfides Chemical class 0.000 claims 1
- 239000003534 dna topoisomerase inhibitor Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 claims 1
- 150000003716 vitamin K3 derivatives Chemical group 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 abstract description 44
- 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 12
- 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
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 abstract description 9
- 229960004857 mitomycin Drugs 0.000 abstract description 6
- 229960004316 cisplatin 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
- 229960004679 doxorubicin Drugs 0.000 abstract description 4
- 102000003903 Cyclin-dependent kinases Human genes 0.000 abstract description 3
- 108090000266 Cyclin-dependent kinases Proteins 0.000 abstract description 3
- 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
- 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
- 230000006820 DNA synthesis Effects 0.000 abstract description 2
- 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
- 239000003528 protein farnesyltransferase inhibitor Substances 0.000 abstract description 2
- 229960003048 vinblastine Drugs 0.000 abstract description 2
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- CQTDVDBFPSMFRR-UHFFFAOYSA-N n-[2-[4-[(4-fluorophenyl)sulfonylamino]phenyl]ethyl]-3,7-dihydroxynaphthalene-2-carboxamide Chemical compound C=1C2=CC(O)=CC=C2C=C(O)C=1C(=O)NCCC(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(F)C=C1 CQTDVDBFPSMFRR-UHFFFAOYSA-N 0.000 description 1
- WYOOPENEUHDZIT-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)phenyl]butanamide Chemical compound C1=CC(NC(=O)CCC)=CC=C1N1CCN(C)CC1 WYOOPENEUHDZIT-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 101150115538 nero gene Proteins 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- GTVPOLSIJWJJNY-UHFFFAOYSA-N olomoucine Chemical compound N1=C(NCCO)N=C2N(C)C=NC2=C1NCC1=CC=CC=C1 GTVPOLSIJWJJNY-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 230000000865 phosphorylative effect Effects 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- IHSLHAZEJBXKMN-UHFFFAOYSA-L potassium nitrosodisulfonate Chemical compound [K+].[K+].[O-]S(=O)(=O)N([O])S([O-])(=O)=O IHSLHAZEJBXKMN-UHFFFAOYSA-L 0.000 description 1
- 229910001487 potassium perchlorate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011535 reaction buffer Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008521 reorganization Effects 0.000 description 1
- YNWSXIWHOSSPCO-UHFFFAOYSA-N rhodium(2+) Chemical compound [Rh+2] YNWSXIWHOSSPCO-UHFFFAOYSA-N 0.000 description 1
- 239000010979 ruby Substances 0.000 description 1
- 229910001750 ruby Inorganic materials 0.000 description 1
- 108091052345 ryanodine receptor (TC 1.A.3.1) family Proteins 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
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 235000004400 serine Nutrition 0.000 description 1
- 150000003355 serines Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- LDTLADDKFLAYJA-UHFFFAOYSA-L sodium metabisulphite Chemical compound [Na+].[Na+].[O-]S(=O)OS([O-])=O LDTLADDKFLAYJA-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- HKSZLNNOFSGOKW-FYTWVXJKSA-N staurosporine Chemical compound C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1[C@H]1C[C@@H](NC)[C@@H](OC)[C@]4(C)O1 HKSZLNNOFSGOKW-FYTWVXJKSA-N 0.000 description 1
- CGPUWJWCVCFERF-UHFFFAOYSA-N staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(OC)O1 CGPUWJWCVCFERF-UHFFFAOYSA-N 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229940063683 taxotere Drugs 0.000 description 1
- YJBKVPRVZAQTPY-UHFFFAOYSA-J tetrachlorostannane;dihydrate Chemical compound O.O.Cl[Sn](Cl)(Cl)Cl YJBKVPRVZAQTPY-UHFFFAOYSA-J 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 235000008521 threonine Nutrition 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-UHFFFAOYSA-N 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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)
- Urology & Nephrology (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Neurosurgery (AREA)
- Endocrinology (AREA)
- Reproductive Health (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 Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR03/07649 | 2003-06-25 | ||
| 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 |
|---|---|
| CA2530668A1 true CA2530668A1 (fr) | 2005-01-06 |
Family
ID=33515382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002530668A Abandoned CA2530668A1 (fr) | 2003-06-25 | 2004-06-24 | Produit comprenant au moins un inhibiteur de phosphatase cdc25 en association avec au moins un autre agent anti-cancereux |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US20060281736A1 (cg-RX-API-DMAC7.html) |
| EP (3) | EP1641453B1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP2007514639A (cg-RX-API-DMAC7.html) |
| AR (2) | AR044930A1 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE439836T1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2530668A1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE602004022674D1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK1641453T3 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2332137T3 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2856688B1 (cg-RX-API-DMAC7.html) |
| MX (1) | MXPA06000216A (cg-RX-API-DMAC7.html) |
| MY (1) | MY141725A (cg-RX-API-DMAC7.html) |
| PL (1) | PL1641453T3 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2005000852A2 (cg-RX-API-DMAC7.html) |
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 |
| ATE368654T1 (de) * | 2001-12-27 | 2007-08-15 | Sod Conseils Rech Applic | Benzothiazol- und benzoxazol-4,7-dionderivate und ihre verwendung als cdc25-phosphatasen- inhibitoren |
| 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 |
| ES2366874T3 (es) * | 2007-09-06 | 2011-10-26 | Basf Se | Mezclas de poliariléteres ramificados y polímeros hidrófilos. |
| WO2009100375A1 (en) | 2008-02-06 | 2009-08-13 | Bristol-Myers Squibb Company | Substituted imidazopyridazines useful as kinase inhibitors |
| UY32776A (es) | 2009-07-09 | 2011-02-28 | Irm Llc | Compuestos de imidazopirazinas sustituidas para el tratamiento de enfermedades parasitarias,composiciones farmacéuticas que los contienen y aplicación. |
| EP2786755A3 (en) | 2010-11-12 | 2014-10-29 | Pharma Mar S.A. | Combination therapy with an antitumor alkaloid |
| CN110691597A (zh) | 2017-04-24 | 2020-01-14 | 诺华股份有限公司 | 2-氨基-1-(2-(4-氟苯基)-3-(4-氟苯基氨基)-8,8-二甲基-5,6-二氢咪唑并[1,2-a]吡嗪-7(8H)-基)乙酮及其组合的治疗方案 |
| US20210106567A1 (en) * | 2019-10-01 | 2021-04-15 | United States Government As Represented By The Department Of Veterans Affairs | Compositions and methods for inhibiting carp-1 binding to nemo |
| CA3158733A1 (en) | 2019-11-21 | 2021-05-27 | Pilar Calvo | Methods of treating small cell lung cancer with lurbinectedin formulations |
| US11981645B1 (en) | 2023-10-10 | 2024-05-14 | King Faisal University | N′-(2-naphthoyloxy)-2-(benzo[d]oxazol-2-yl)acetimidamide as antimicrobial compound |
Family Cites Families (15)
| 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 |
| PT1233787E (pt) * | 1999-11-09 | 2005-04-29 | Conseils Rech S Et D Applic Sc | Produto contendo um inibidor da transducao dos sinais das proteinas g heterotrimericas em associacao com um outro agente anticanceroso para utilizacao terapeutica no tratamento do cancro |
| FR2812198B1 (fr) * | 2000-07-28 | 2008-07-18 | Sod Conseils Rech Applic | DERIVES D'AMIDINES INHIBITEURS DE PHOSPHATASES cdc25 |
| JP2004516297A (ja) * | 2000-12-20 | 2004-06-03 | ソシエテ・ド・コンセイユ・ド・ルシエルシエ・エ・ダアツプリカーション・シヤンテイフイツク・（エス．セー．エール．アー．エス） | サイクリン依存性キナーゼ（ｃｄｋ）及びグリコーゲンシンターゼキナーゼ−３（ｇｓｋ−３）の阻害剤 |
| 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 |
| ATE368654T1 (de) * | 2001-12-27 | 2007-08-15 | Sod Conseils Rech Applic | Benzothiazol- und benzoxazol-4,7-dionderivate und ihre verwendung als cdc25-phosphatasen- inhibitoren |
| 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 |
| 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 US US10/562,625 patent/US20060281736A1/en not_active Abandoned
- 2004-06-24 WO PCT/FR2004/001586 patent/WO2005000852A2/fr not_active Ceased
- 2004-06-24 EP EP04767442A patent/EP1641453B1/fr not_active Expired - Lifetime
- 2004-06-24 PL PL04767442T patent/PL1641453T3/pl unknown
- 2004-06-24 CA CA002530668A patent/CA2530668A1/fr not_active Abandoned
- 2004-06-24 EP EP08020152A patent/EP2335702A1/fr not_active Withdrawn
- 2004-06-24 DE DE602004022674T patent/DE602004022674D1/de not_active Expired - Lifetime
- 2004-06-24 AT AT04767442T patent/ATE439836T1/de not_active IP Right Cessation
- 2004-06-24 EP EP07006144A patent/EP1792905A1/fr not_active Withdrawn
- 2004-06-24 JP JP2006516322A patent/JP2007514639A/ja active Pending
- 2004-06-24 MX MXPA06000216A patent/MXPA06000216A/es active IP Right Grant
- 2004-06-24 DK DK04767442T patent/DK1641453T3/da active
- 2004-06-24 ES ES04767442T patent/ES2332137T3/es not_active Expired - Lifetime
- 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 |
|---|---|
| AR044930A1 (es) | 2005-10-12 |
| DE602004022674D1 (de) | 2009-10-01 |
| MY141725A (en) | 2010-06-15 |
| WO2005000852A3 (fr) | 2005-06-30 |
| EP1641453B1 (fr) | 2009-08-19 |
| EP1792905A1 (fr) | 2007-06-06 |
| FR2856688A1 (fr) | 2004-12-31 |
| WO2005000852A2 (fr) | 2005-01-06 |
| AR070977A2 (es) | 2010-05-19 |
| JP2009149694A (ja) | 2009-07-09 |
| FR2856688B1 (fr) | 2008-05-30 |
| MXPA06000216A (es) | 2006-04-11 |
| EP2335702A1 (fr) | 2011-06-22 |
| US20060281736A1 (en) | 2006-12-14 |
| ES2332137T3 (es) | 2010-01-27 |
| US20090253685A1 (en) | 2009-10-08 |
| DK1641453T3 (da) | 2009-12-14 |
| PL1641453T3 (pl) | 2010-01-29 |
| US20090137596A1 (en) | 2009-05-28 |
| EP1641453A2 (fr) | 2006-04-05 |
| JP2007514639A (ja) | 2007-06-07 |
| ATE439836T1 (de) | 2009-09-15 |
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