AU2006242380A1 - Mitotic kinesin inhibitors and methods of use thereof - Google Patents
Mitotic kinesin inhibitors and methods of use thereof Download PDFInfo
- Publication number
- AU2006242380A1 AU2006242380A1 AU2006242380A AU2006242380A AU2006242380A1 AU 2006242380 A1 AU2006242380 A1 AU 2006242380A1 AU 2006242380 A AU2006242380 A AU 2006242380A AU 2006242380 A AU2006242380 A AU 2006242380A AU 2006242380 A1 AU2006242380 A1 AU 2006242380A1
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- thiadiazol
- compound
- phenyl
- difluorophenyl
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims description 78
- 230000000394 mitotic effect Effects 0.000 title claims description 47
- 102000010638 Kinesin Human genes 0.000 title claims description 35
- 108010063296 Kinesin Proteins 0.000 title claims description 35
- 239000003112 inhibitor Substances 0.000 title description 39
- 150000001875 compounds Chemical class 0.000 claims description 266
- -1 nitro, hydroxy Chemical group 0.000 claims description 220
- 125000000217 alkyl group Chemical group 0.000 claims description 195
- 125000000623 heterocyclic group Chemical group 0.000 claims description 138
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 134
- 125000001072 heteroaryl group Chemical group 0.000 claims description 126
- 125000003118 aryl group Chemical group 0.000 claims description 122
- 239000000203 mixture Substances 0.000 claims description 115
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 100
- 150000002367 halogens Chemical class 0.000 claims description 86
- 229910052736 halogen Inorganic materials 0.000 claims description 84
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 78
- 238000011282 treatment Methods 0.000 claims description 75
- 125000003342 alkenyl group Chemical group 0.000 claims description 71
- 150000003839 salts Chemical class 0.000 claims description 66
- 125000000304 alkynyl group Chemical group 0.000 claims description 65
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 63
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 60
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 47
- 229920006395 saturated elastomer Polymers 0.000 claims description 45
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 43
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 40
- 210000004027 cell Anatomy 0.000 claims description 38
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims description 38
- 239000012453 solvate Substances 0.000 claims description 38
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 38
- 206010028980 Neoplasm Diseases 0.000 claims description 34
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 31
- 239000002207 metabolite Substances 0.000 claims description 29
- 230000002159 abnormal effect Effects 0.000 claims description 27
- 239000008194 pharmaceutical composition Substances 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
- 125000005842 heteroatom Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000004043 oxo group Chemical group O=* 0.000 claims description 22
- 102000029749 Microtubule Human genes 0.000 claims description 21
- 108091022875 Microtubule Proteins 0.000 claims description 21
- 210000004688 microtubule Anatomy 0.000 claims description 21
- 230000010261 cell growth Effects 0.000 claims description 20
- 230000002401 inhibitory effect Effects 0.000 claims description 20
- 241000124008 Mammalia Species 0.000 claims description 19
- 201000011510 cancer Diseases 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
- 241000282414 Homo sapiens Species 0.000 claims description 18
- 241001465754 Metazoa Species 0.000 claims description 18
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 229910004013 NO 2 Inorganic materials 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000000539 amino acid group Chemical group 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- GRHZLQBPAJAHDM-SPRQWYLLSA-N [(3as,4r,6ar)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] n-[(2s,4s,5s)-5-[[2-(2,6-dimethylphenoxy)acetyl]amino]-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate Chemical compound CC1=CC=CC(C)=C1OCC(=O)N[C@H]([C@@H](O)C[C@H](CC=1C=CC=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)CC1=CC=CC=C1 GRHZLQBPAJAHDM-SPRQWYLLSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 125000002837 carbocyclic group Chemical group 0.000 claims description 9
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 8
- 108010016626 Dipeptides Proteins 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 230000020347 spindle assembly Effects 0.000 claims description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000005605 benzo group Chemical group 0.000 claims description 6
- 150000001723 carbon free-radicals Chemical class 0.000 claims description 6
- 230000035755 proliferation Effects 0.000 claims description 6
- 238000002560 therapeutic procedure Methods 0.000 claims description 6
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 208000015181 infectious disease Diseases 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
- 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 description 4
- 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 compound C=1C=CC=CC=1C1(CCCN)SC(C=2C(=CC=C(F)C=2)F)=NN1C1=NC=CS1 QBIFTEIVPCDEDY-UHFFFAOYSA-N 0.000 claims description 4
- DJPGYJOPRYQWNQ-UHFFFAOYSA-N 3-[5-(2,5-difluorophenyl)-3-(3-methyl-1,2,4-oxadiazol-5-yl)-2-phenyl-1,3,4-thiadiazol-2-yl]propan-1-amine Chemical compound CC1=NOC(N2C(SC(=N2)C=2C(=CC=C(F)C=2)F)(CCCN)C=2C=CC=CC=2)=N1 DJPGYJOPRYQWNQ-UHFFFAOYSA-N 0.000 claims description 4
- NAWQNSWTDDCFFZ-UHFFFAOYSA-N 3-[5-(2,5-difluorophenyl)-3-(5-methyl-1,3,4-oxadiazol-2-yl)-2-phenyl-1,3,4-thiadiazol-2-yl]propan-1-amine Chemical compound O1C(C)=NN=C1N1C(C=2C=CC=CC=2)(CCCN)SC(C=2C(=CC=C(F)C=2)F)=N1 NAWQNSWTDDCFFZ-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
- 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 description 4
- 150000001721 carbon Chemical class 0.000 claims description 4
- 230000002538 fungal effect Effects 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- MRFMKVLOAVTAHC-UHFFFAOYSA-N 3-[5-(2,5-difluorophenyl)-2-phenyl-3-(5-phenyl-1h-1,2,4-triazol-3-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)=NN1C(N1)=NN=C1C1=CC=CC=C1 MRFMKVLOAVTAHC-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 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 description 3
- 241000206602 Eukaryota Species 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- 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 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
- 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
- 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
- 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 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
- 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 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
- 102100021850 Nardilysin Human genes 0.000 claims 1
- 108090000970 Nardilysin Proteins 0.000 claims 1
- KOCXAKZNVBAIJU-UHFFFAOYSA-N ethyl 5-[2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-1,3,4-oxadiazole-2-carboxylate Chemical compound O1C(C(=O)OCC)=NN=C1N1C(C=2C=CC=CC=2)(CCCN)SC(C=2C(=CC=C(F)C=2)F)=N1 KOCXAKZNVBAIJU-UHFFFAOYSA-N 0.000 claims 1
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 1
- 230000032297 kinesis Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 237
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 206
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 130
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 122
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 100
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 90
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 85
- 239000000047 product Substances 0.000 description 85
- 239000000243 solution Substances 0.000 description 80
- 235000019439 ethyl acetate Nutrition 0.000 description 76
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 67
- 239000000543 intermediate Substances 0.000 description 57
- 239000002904 solvent Substances 0.000 description 55
- 238000002360 preparation method Methods 0.000 description 45
- 229940002612 prodrug Drugs 0.000 description 44
- 239000000651 prodrug Substances 0.000 description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- 230000002829 reductive effect Effects 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 41
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 39
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 38
- 238000003756 stirring Methods 0.000 description 38
- 239000011734 sodium Substances 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 33
- 229940086542 triethylamine Drugs 0.000 description 33
- 238000005481 NMR spectroscopy Methods 0.000 description 32
- 239000002585 base Substances 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 28
- 238000003818 flash chromatography Methods 0.000 description 28
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
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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
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
- C07D419/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D419/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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- C07D487/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
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- C07D495/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D497/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
- C07F9/65392—Five-membered rings containing two nitrogen atoms
- C07F9/65395—Five-membered rings containing two nitrogen atoms having the two nitrogen atoms in positions 1 and 2
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- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Fertilizers (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
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| PCT/US2006/016526 WO2006119146A1 (en) | 2005-05-02 | 2006-05-01 | Mitotic kinesin inhibitors and methods of use thereof |
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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 |
| ES2565983T3 (es) * | 2007-10-19 | 2016-04-08 | Merck Sharp & Dohme Corp. | Derivados de 1,3,4-tiadiazol espiro-condensados para inhibir la actividad quinesina de KSP |
| 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 |
| CA3189738A1 (en) * | 2020-08-07 | 2022-02-10 | Italfarmaco S.P.A. | Novel oxadiazole-based selective hdac6 inhibitors |
| 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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| US7449486B2 (en) | 2004-10-19 | 2008-11-11 | Array Biopharma Inc. | Mitotic kinesin inhibitors and methods of use thereof |
| WO2006050962A1 (en) * | 2004-11-10 | 2006-05-18 | Basf Aktiengesellschaft | A method of regenerating a catalyst |
| UA95907C2 (en) * | 2005-05-02 | 2011-09-26 | Эррей Биофарма Инк. | Mitotic kinesin inhibitors and methods of use thereof |
| WO2008042982A2 (en) | 2006-10-03 | 2008-04-10 | Cola Jr Gary M | Microtreatment of iron-based alloy, apparatus and method therefor, and articles resulting therefrom |
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| CN101248068A (zh) | 2008-08-20 |
| JP2008540418A (ja) | 2008-11-20 |
| UA95907C2 (en) | 2011-09-26 |
| US7795282B2 (en) | 2010-09-14 |
| CA2606708C (en) | 2015-01-06 |
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| US9221841B2 (en) | 2015-12-29 |
| AU2006242380A2 (en) | 2008-07-03 |
| KR101329901B1 (ko) | 2013-11-14 |
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| US20060247178A1 (en) | 2006-11-02 |
| EP1879886A4 (en) | 2010-09-08 |
| US20100331283A1 (en) | 2010-12-30 |
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| US8268871B2 (en) | 2012-09-18 |
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| EP1879886A1 (en) | 2008-01-23 |
| BRPI0610193A2 (pt) | 2010-06-01 |
| ZA200710218B (en) | 2009-07-29 |
| IL186707A (en) | 2013-04-30 |
| US20150191490A1 (en) | 2015-07-09 |
| US20140018399A1 (en) | 2014-01-16 |
| IL186707A0 (en) | 2008-02-09 |
| TW200716153A (en) | 2007-05-01 |
| US20130109656A1 (en) | 2013-05-02 |
| NO20076186L (no) | 2008-02-01 |
| HK1115376A1 (en) | 2008-11-28 |
| US8580828B2 (en) | 2013-11-12 |
| KR20080003934A (ko) | 2008-01-08 |
| EP1879886B1 (en) | 2014-07-09 |
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