JP2008540418A5 - - Google Patents
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- Publication number
- JP2008540418A5 JP2008540418A5 JP2008510090A JP2008510090A JP2008540418A5 JP 2008540418 A5 JP2008540418 A5 JP 2008540418A5 JP 2008510090 A JP2008510090 A JP 2008510090A JP 2008510090 A JP2008510090 A JP 2008510090A JP 2008540418 A5 JP2008540418 A5 JP 2008540418A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- thiadiazol
- heteroaryl
- difluorophenyl
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 98
- 125000000623 heterocyclic group Chemical group 0.000 claims description 89
- 125000000217 alkyl group Chemical group 0.000 claims description 88
- 125000001072 heteroaryl group Chemical group 0.000 claims description 88
- 125000003118 aryl group Chemical group 0.000 claims description 77
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 62
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 56
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 53
- -1 nitro, hydroxy Chemical group 0.000 claims description 52
- 229910052736 halogen Inorganic materials 0.000 claims description 44
- 125000003342 alkenyl group Chemical group 0.000 claims description 43
- 150000002367 halogens Chemical class 0.000 claims description 43
- 125000000304 alkynyl group Chemical group 0.000 claims description 38
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 37
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 33
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 33
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000004043 oxo group Chemical group O=* 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- BPXYEYJNCXITEY-UHFFFAOYSA-N diazonio(trifluoromethoxy)azanide Chemical compound FC(F)(F)ON=[N+]=[N-] BPXYEYJNCXITEY-UHFFFAOYSA-N 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 108010016626 Dipeptides Proteins 0.000 claims description 4
- 125000000539 amino acid group Chemical group 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 150000001723 carbon free-radicals Chemical class 0.000 claims description 3
- 229910004013 NO 2 Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- DYMRYCZRMAHYKE-UHFFFAOYSA-N n-diazonitramide Chemical compound [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 4
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 2
- WNZLRGQZDBXGAG-UHFFFAOYSA-N 3-[5-(2,5-difluorophenyl)-2-phenyl-3-(4,5,6,7-tetrahydro-[1,3]thiazolo[5,4-c]pyridin-2-yl)-1,3,4-thiadiazol-2-yl]propan-1-amine Chemical compound N=1N(C=2SC=3CNCCC=3N=2)C(CCCN)(C=2C=CC=CC=2)SC=1C1=CC(F)=CC=C1F WNZLRGQZDBXGAG-UHFFFAOYSA-N 0.000 claims 2
- BULAHLCUZJYHFT-UHFFFAOYSA-N 3-[5-(2,5-difluorophenyl)-3-(5-methyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)-2-phenyl-1,3,4-thiadiazol-2-yl]propan-1-amine Chemical compound S1C=2CN(C)CCC=2N=C1N1N=C(C=2C(=CC=C(F)C=2)F)SC1(CCCN)C1=CC=CC=C1 BULAHLCUZJYHFT-UHFFFAOYSA-N 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 230000010261 cell growth Effects 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- INFQYUDBHPFNDN-UHFFFAOYSA-N 2-[2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-n,n-dimethyl-1,3-thiazole-4-carboxamide Chemical compound CN(C)C(=O)C1=CSC(N2C(SC(=N2)C=2C(=CC=C(F)C=2)F)(CCCN)C=2C=CC=CC=2)=N1 INFQYUDBHPFNDN-UHFFFAOYSA-N 0.000 claims 1
- BJCBZJMQLAVBIF-UHFFFAOYSA-N 2-[2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-n-methyl-1,3-thiazole-4-carboxamide Chemical compound CNC(=O)C1=CSC(N2C(SC(=N2)C=2C(=CC=C(F)C=2)F)(CCCN)C=2C=CC=CC=2)=N1 BJCBZJMQLAVBIF-UHFFFAOYSA-N 0.000 claims 1
- MYZPOIGSXABPGN-UHFFFAOYSA-N 2-[5-(2,5-difluorophenyl)-2-(methoxymethoxymethyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-5-methyl-1,3,4-oxadiazole Chemical compound C=1C=CC=CC=1C1(COCOC)SC(C=2C(=CC=C(F)C=2)F)=NN1C1=NN=C(C)O1 MYZPOIGSXABPGN-UHFFFAOYSA-N 0.000 claims 1
- LXPFVZSELSJTHX-UHFFFAOYSA-N 2-[5-(2,5-difluorophenyl)-2-phenyl-3-(4,5,6,7-tetrahydro-[1,3]thiazolo[5,4-c]pyridin-2-yl)-1,3,4-thiadiazol-2-yl]ethanol Chemical compound N=1N(C=2SC=3CNCCC=3N=2)C(CCO)(C=2C=CC=CC=2)SC=1C1=CC(F)=CC=C1F LXPFVZSELSJTHX-UHFFFAOYSA-N 0.000 claims 1
- FTUMUULEVIXDNV-UHFFFAOYSA-N 2-[5-(2,5-difluorophenyl)-3-(5-methyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)-2-phenyl-1,3,4-thiadiazol-2-yl]ethanol Chemical compound S1C=2CN(C)CCC=2N=C1N1N=C(C=2C(=CC=C(F)C=2)F)SC1(CCO)C1=CC=CC=C1 FTUMUULEVIXDNV-UHFFFAOYSA-N 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 1
- UGDUCQDQRCDLPD-UHFFFAOYSA-N 3-[2-(3-aminopropyl)-5-(2,5-difluorophenyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-1,3,4-thiadiazol-2-yl]phenol Chemical compound S1C(C)=NN=C1N1C(C=2C=C(O)C=CC=2)(CCCN)SC(C=2C(=CC=C(F)C=2)F)=N1 UGDUCQDQRCDLPD-UHFFFAOYSA-N 0.000 claims 1
- UTUQGRAEROJSRH-UHFFFAOYSA-N 3-[3-(5-bromo-1,3,4-thiadiazol-2-yl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-2-yl]propan-1-amine Chemical compound C=1C=CC=CC=1C1(CCCN)SC(C=2C(=CC=C(F)C=2)F)=NN1C1=NN=C(Br)S1 UTUQGRAEROJSRH-UHFFFAOYSA-N 0.000 claims 1
- SPRJXWKDCVPPBP-UHFFFAOYSA-N 3-[5-(2,5-difluorophenyl)-2-(3-fluorophenyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-1,3,4-thiadiazol-2-yl]propan-1-amine Chemical compound S1C(C)=NN=C1N1C(C=2C=C(F)C=CC=2)(CCCN)SC(C=2C(=CC=C(F)C=2)F)=N1 SPRJXWKDCVPPBP-UHFFFAOYSA-N 0.000 claims 1
- KUMPBUIEGOXENM-UHFFFAOYSA-N 3-[5-(2,5-difluorophenyl)-2-(4-fluorophenyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-1,3,4-thiadiazol-2-yl]propan-1-amine Chemical compound S1C(C)=NN=C1N1C(C=2C=CC(F)=CC=2)(CCCN)SC(C=2C(=CC=C(F)C=2)F)=N1 KUMPBUIEGOXENM-UHFFFAOYSA-N 0.000 claims 1
- GAGJFBHRBPOIEI-UHFFFAOYSA-N 3-[5-(2,5-difluorophenyl)-2-phenyl-3-(1,3,4-thiadiazol-2-yl)-1,3,4-thiadiazol-2-yl]propan-1-amine Chemical compound C=1C=CC=CC=1C1(CCCN)SC(C=2C(=CC=C(F)C=2)F)=NN1C1=NN=CS1 GAGJFBHRBPOIEI-UHFFFAOYSA-N 0.000 claims 1
- QBIFTEIVPCDEDY-UHFFFAOYSA-N 3-[5-(2,5-difluorophenyl)-2-phenyl-3-(1,3-thiazol-2-yl)-1,3,4-thiadiazol-2-yl]propan-1-amine Chemical class C=1C=CC=CC=1C1(CCCN)SC(C=2C(=CC=C(F)C=2)F)=NN1C1=NC=CS1 QBIFTEIVPCDEDY-UHFFFAOYSA-N 0.000 claims 1
- BEJUJMAZTRHVIK-UHFFFAOYSA-N 3-[5-(2,5-difluorophenyl)-2-phenyl-3-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]-1,3,4-thiadiazol-2-yl]propan-1-amine Chemical compound C=1C=CC=CC=1C1(CCCN)SC(C=2C(=CC=C(F)C=2)F)=NN1C1=NN=C(C(F)(F)F)S1 BEJUJMAZTRHVIK-UHFFFAOYSA-N 0.000 claims 1
- HXXCNBAOPTTYNV-UHFFFAOYSA-N 3-[5-(2,5-difluorophenyl)-3-(1,3-oxazol-2-yl)-2-phenyl-1,3,4-thiadiazol-2-yl]propan-1-amine Chemical class C=1C=CC=CC=1C1(CCCN)SC(C=2C(=CC=C(F)C=2)F)=NN1C1=NC=CO1 HXXCNBAOPTTYNV-UHFFFAOYSA-N 0.000 claims 1
- LFZRYKXSUKNODO-UHFFFAOYSA-N 3-[5-(2,5-difluorophenyl)-3-(1-methyl-5-phenyl-1,2,4-triazol-3-yl)-2-phenyl-1,3,4-thiadiazol-2-yl]propan-1-amine Chemical compound CN1N=C(N2C(SC(=N2)C=2C(=CC=C(F)C=2)F)(CCCN)C=2C=CC=CC=2)N=C1C1=CC=CC=C1 LFZRYKXSUKNODO-UHFFFAOYSA-N 0.000 claims 1
- CULOKSDPHIJLER-UHFFFAOYSA-N 3-[5-(2,5-difluorophenyl)-3-(4,5-dihydro-1,3-thiazol-2-yl)-2-phenyl-1,3,4-thiadiazol-2-yl]propan-1-amine Chemical compound C=1C=CC=CC=1C1(CCCN)SC(C=2C(=CC=C(F)C=2)F)=NN1C1=NCCS1 CULOKSDPHIJLER-UHFFFAOYSA-N 0.000 claims 1
- RTBKZNPXNKACFP-UHFFFAOYSA-N 3-[5-(2,5-difluorophenyl)-3-(4-ethyl-1,3-thiazol-2-yl)-2-phenyl-1,3,4-thiadiazol-2-yl]propan-1-amine Chemical compound CCC1=CSC(N2C(SC(=N2)C=2C(=CC=C(F)C=2)F)(CCCN)C=2C=CC=CC=2)=N1 RTBKZNPXNKACFP-UHFFFAOYSA-N 0.000 claims 1
- LCBMRTJMCLIPJW-UHFFFAOYSA-N 3-[5-(2,5-difluorophenyl)-3-(4-methyl-1,3-thiazol-2-yl)-2-phenyl-1,3,4-thiadiazol-2-yl]propan-1-amine Chemical compound CC1=CSC(N2C(SC(=N2)C=2C(=CC=C(F)C=2)F)(CCCN)C=2C=CC=CC=2)=N1 LCBMRTJMCLIPJW-UHFFFAOYSA-N 0.000 claims 1
- GRBWNFVBJCKZST-UHFFFAOYSA-N 3-[5-(2,5-difluorophenyl)-3-(5-ethyl-1,3,4-oxadiazol-2-yl)-2-phenyl-1,3,4-thiadiazol-2-yl]propan-1-amine Chemical compound O1C(CC)=NN=C1N1C(C=2C=CC=CC=2)(CCCN)SC(C=2C(=CC=C(F)C=2)F)=N1 GRBWNFVBJCKZST-UHFFFAOYSA-N 0.000 claims 1
- KHCWRAXXQGCEJO-UHFFFAOYSA-N 3-[5-(2,5-difluorophenyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-phenyl-1,3,4-thiadiazol-2-yl]propan-1-amine Chemical compound S1C(C)=NN=C1N1C(C=2C=CC=CC=2)(CCCN)SC(C=2C(=CC=C(F)C=2)F)=N1 KHCWRAXXQGCEJO-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- HPZVXZVJSNVJIF-UHFFFAOYSA-N 5-(2,5-difluorophenyl)-2-methyl-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-phenyl-1,3,4-thiadiazole Chemical compound S1C(C)=NN=C1N1C(C=2C=CC=CC=2)(C)SC(C=2C(=CC=C(F)C=2)F)=N1 HPZVXZVJSNVJIF-UHFFFAOYSA-N 0.000 claims 1
- BLLPQBHVMOWYEK-UHFFFAOYSA-N 5-[2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-n-ethyl-1,3,4-oxadiazol-2-amine Chemical compound O1C(NCC)=NN=C1N1C(C=2C=CC=CC=2)(CCCN)SC(C=2C(=CC=C(F)C=2)F)=N1 BLLPQBHVMOWYEK-UHFFFAOYSA-N 0.000 claims 1
- BNTLWGQXYRQWGN-UHFFFAOYSA-N 5-[2-(3-aminopropyl)-5-(3-fluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-3,4-dihydropyrrol-2-one Chemical compound C=1C=CC=CC=1C1(CCCN)SC(C=2C=C(F)C=CC=2)=NN1C1=NC(=O)CC1 BNTLWGQXYRQWGN-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000000394 mitotic effect Effects 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 230000020347 spindle assembly Effects 0.000 claims 1
- 0 CC1=NN2I*C*C*CC2(*)*1 Chemical compound CC1=NN2I*C*C*CC2(*)*1 0.000 description 6
- 238000003556 assay Methods 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 102000003855 L-lactate dehydrogenase Human genes 0.000 description 2
- 108700023483 L-lactate dehydrogenases Proteins 0.000 description 2
- 102000013009 Pyruvate Kinase Human genes 0.000 description 2
- 108020005115 Pyruvate Kinase Proteins 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 2
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 1
- 241000239366 Euphausiacea Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 102000029749 Microtubule Human genes 0.000 description 1
- 108091022875 Microtubule Proteins 0.000 description 1
- 229930012538 Paclitaxel Natural products 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical class CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000001548 androgenic effect Effects 0.000 description 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
- 238000010256 biochemical assay Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N c1ccncc1 Chemical compound c1ccncc1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N c1cncnc1 Chemical compound c1cncnc1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N c1ncncn1 Chemical compound c1ncncn1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 238000001952 enzyme assay Methods 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 210000004688 microtubule Anatomy 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67689005P | 2005-05-02 | 2005-05-02 | |
| PCT/US2006/016526 WO2006119146A1 (en) | 2005-05-02 | 2006-05-01 | Mitotic kinesin inhibitors and methods of use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008540418A JP2008540418A (ja) | 2008-11-20 |
| JP2008540418A5 true JP2008540418A5 (enExample) | 2012-04-05 |
Family
ID=37308299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008510090A Pending JP2008540418A (ja) | 2005-05-02 | 2006-05-01 | 有糸分裂キネシンおよびその使用方法 |
Country Status (16)
| Country | Link |
|---|---|
| US (5) | US7795282B2 (enExample) |
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Families Citing this family (10)
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| US7449486B2 (en) | 2004-10-19 | 2008-11-11 | Array Biopharma Inc. | Mitotic kinesin inhibitors and methods of use thereof |
| UA95907C2 (en) | 2005-05-02 | 2011-09-26 | Эррей Биофарма Инк. | Mitotic kinesin inhibitors and methods of use thereof |
| MX2010004312A (es) * | 2007-10-19 | 2010-07-05 | Schering Corp | Derivados de 1,3,4-tiadiazol espiro-condensados para inhibir la actividad de quinesina de la proteina de quinesina del huso. |
| US9561214B2 (en) * | 2008-10-16 | 2017-02-07 | Array Biopharma Inc. | Method of treatment using inhibitors of mitosis |
| DE102009058280A1 (de) * | 2009-12-14 | 2011-06-16 | Merck Patent Gmbh | Thiazolderivate |
| EP2455456A1 (en) | 2010-11-22 | 2012-05-23 | Institut Curie | Use of kinesin inhibitors in HIV infection treatment and a method for screening them |
| WO2016094307A1 (en) | 2014-12-08 | 2016-06-16 | The Research Foundation For The State University Of New York | Anti-fungals targeting the synthesis of fungal shingolipids |
| WO2018232298A1 (en) | 2017-06-16 | 2018-12-20 | The Research Foundation For The State University Of New York | Anti-fungals compounds targeting the synthesis of fungal sphingolipids |
| JP2023537052A (ja) * | 2020-08-07 | 2023-08-30 | イタルファルマコ ソシエタ ペル アチオニ | 新規オキサジアゾール系の選択的ｈｄａｃ６阻害剤 |
| CN114014824B (zh) * | 2020-12-09 | 2023-06-13 | 上海科技大学 | 一种杂环化合物的应用 |
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-
2006
- 2006-01-05 UA UAA200713355A patent/UA95907C2/ru unknown
- 2006-05-01 AU AU2006242380A patent/AU2006242380A1/en not_active Abandoned
- 2006-05-01 RU RU2007144612/04A patent/RU2007144612A/ru not_active Application Discontinuation
- 2006-05-01 BR BRPI0610193-3A patent/BRPI0610193A2/pt not_active IP Right Cessation
- 2006-05-01 US US11/415,455 patent/US7795282B2/en not_active Expired - Fee Related
- 2006-05-01 EP EP06758821.0A patent/EP1879886B1/en active Active
- 2006-05-01 JP JP2008510090A patent/JP2008540418A/ja active Pending
- 2006-05-01 KR KR1020077027972A patent/KR101329901B1/ko not_active Expired - Fee Related
- 2006-05-01 CN CNA2006800242288A patent/CN101248068A/zh active Pending
- 2006-05-01 MX MX2007013539A patent/MX2007013539A/es not_active Application Discontinuation
- 2006-05-01 WO PCT/US2006/016526 patent/WO2006119146A1/en not_active Ceased
- 2006-05-01 CA CA2606708A patent/CA2606708C/en not_active Expired - Fee Related
- 2006-05-02 TW TW095115570A patent/TW200716153A/zh unknown
-
2007
- 2007-10-17 IL IL186707A patent/IL186707A/en active IP Right Grant
- 2007-11-27 ZA ZA200710218A patent/ZA200710218B/xx unknown
- 2007-11-30 NO NO20076186A patent/NO20076186L/no not_active Application Discontinuation
-
2010
- 2010-06-23 US US12/822,066 patent/US8268871B2/en not_active Expired - Fee Related
-
2012
- 2012-08-15 US US13/586,355 patent/US8580828B2/en not_active Expired - Fee Related
-
2013
- 2013-09-19 US US14/031,958 patent/US20140018399A1/en not_active Abandoned
-
2015
- 2015-03-19 US US14/663,286 patent/US9221841B2/en not_active Expired - Fee Related
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