PT1761515E - Derivados de tetra-hidroquinolina 2-(hetero)-aril substituídos - Google Patents

Info

Publication number

PT1761515E

PT1761515E PT04803833T PT04803833T PT1761515E PT 1761515 E PT1761515 E PT 1761515E PT 04803833 T PT04803833 T PT 04803833T PT 04803833 T PT04803833 T PT 04803833T PT 1761515 E PT1761515 E PT 1761515E

Authority

PT

Portugal

Prior art keywords

phenyl

compounds

quinoline

formula

hexahydro

Prior art date

2003-12-20

Links

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• Global Dossier
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• 125000003118 aryl group Chemical group 0.000 title claims abstract description 10
• 125000000147 tetrahydroquinolinyl group Chemical class N1(CCCC2=CC=CC=C12)* 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 174
• -1 (CY 2) n-Q 1> Chemical group 0.000 claims abstract description 137
• 150000003839 salts Chemical class 0.000 claims abstract description 57
• 239000000203 mixture Substances 0.000 claims abstract description 55
• XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 claims abstract description 33
• 229960004448 pentamidine Drugs 0.000 claims abstract description 30
• 239000012453 solvate Substances 0.000 claims abstract description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 15
• 230000000394 mitotic effect Effects 0.000 claims abstract description 12
• 238000002360 preparation method Methods 0.000 claims abstract description 11
• 108090000623 proteins and genes Proteins 0.000 claims abstract description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
• 102000004169 proteins and genes Human genes 0.000 claims abstract description 8
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
• 239000002207 metabolite Substances 0.000 claims abstract description 7
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims abstract 3
• 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims abstract 3
• 101150065749 Churc1 gene Proteins 0.000 claims abstract 3
• 102100038239 Protein Churchill Human genes 0.000 claims abstract 3
• 239000003112 inhibitor Substances 0.000 claims description 43
• 239000003814 drug Substances 0.000 claims description 35
• 206010028980 Neoplasm Diseases 0.000 claims description 33
• 238000006243 chemical reaction Methods 0.000 claims description 26
• 239000003795 chemical substances by application Substances 0.000 claims description 25
• 238000000034 method Methods 0.000 claims description 25
• 238000011282 treatment Methods 0.000 claims description 24
• 239000002253 acid Substances 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 201000010099 disease Diseases 0.000 claims description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
• 230000005764 inhibitory process Effects 0.000 claims description 16
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 14
• 239000000126 substance Substances 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 230000008569 process Effects 0.000 claims description 11
• 230000001028 anti-proliverative effect Effects 0.000 claims description 9
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 238000011321 prophylaxis Methods 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 229910002651 NO3 Inorganic materials 0.000 claims description 5
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 5
• 229940127089 cytotoxic agent Drugs 0.000 claims description 5
• 239000002254 cytotoxic agent Substances 0.000 claims description 5
• 231100000599 cytotoxic agent Toxicity 0.000 claims description 5
• 230000036961 partial effect Effects 0.000 claims description 5
• 210000002784 stomach Anatomy 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
• FNZXKBQNQHNXPH-UHFFFAOYSA-N 8-chloro-4-phenyl-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline Chemical compound C12CCOC2C2=CC(Cl)=CC=C2NC1C1=CC=CC=C1 FNZXKBQNQHNXPH-UHFFFAOYSA-N 0.000 claims description 4
• CXOFUBJHHGOFDV-UHFFFAOYSA-N 9-chloro-5-phenyl-3,4,4a,5,6,10b-hexahydro-2h-pyrano[3,2-c]quinoline Chemical compound C12CCCOC2C2=CC(Cl)=CC=C2NC1C1=CC=CC=C1 CXOFUBJHHGOFDV-UHFFFAOYSA-N 0.000 claims description 4
• 206010009944 Colon cancer Diseases 0.000 claims description 4
• 208000009956 adenocarcinoma Diseases 0.000 claims description 4
• 201000008275 breast carcinoma Diseases 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
• 239000002834 estrogen receptor modulator Substances 0.000 claims description 4
• 230000012010 growth Effects 0.000 claims description 4
• 102000027483 retinoid hormone receptors Human genes 0.000 claims description 4
• 108091008679 retinoid hormone receptors Proteins 0.000 claims description 4
• 239000000849 selective androgen receptor modulator Substances 0.000 claims description 4
• 239000002841 Lewis acid Substances 0.000 claims description 3
• 239000004037 angiogenesis inhibitor Substances 0.000 claims description 3
• 229940121369 angiogenesis inhibitor Drugs 0.000 claims description 3
• JHXKRIRFYBPWGE-UHFFFAOYSA-K bismuth chloride Chemical compound Cl[Bi](Cl)Cl JHXKRIRFYBPWGE-UHFFFAOYSA-K 0.000 claims description 3
• 210000004369 blood Anatomy 0.000 claims description 3
• 239000008280 blood Substances 0.000 claims description 3
• 125000004432 carbon atom Chemical group C* 0.000 claims description 3
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 3
• 229910052736 halogen Inorganic materials 0.000 claims description 3
• 150000002367 halogens Chemical class 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• 229910052740 iodine Inorganic materials 0.000 claims description 3
• 150000007517 lewis acids Chemical class 0.000 claims description 3
• 210000004072 lung Anatomy 0.000 claims description 3
• 210000004324 lymphatic system Anatomy 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
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 3
• 230000002685 pulmonary effect Effects 0.000 claims description 3
• 238000001959 radiotherapy Methods 0.000 claims description 3
• HZXJVDYQRYYYOR-UHFFFAOYSA-K scandium(iii) trifluoromethanesulfonate Chemical compound [Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HZXJVDYQRYYYOR-UHFFFAOYSA-K 0.000 claims description 3
• AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 claims description 3
• YEDDVXZFXSHDIB-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoropropan-1-ol Chemical compound OC(F)(F)C(F)(F)C(F)F YEDDVXZFXSHDIB-UHFFFAOYSA-N 0.000 claims description 2
• VAGNKUQGTBABTE-UHFFFAOYSA-N 1-(2-phenyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-one Chemical compound O=C1CCCN1C1C2=CC=CC=C2NC(C=2C=CC=CC=2)C1 VAGNKUQGTBABTE-UHFFFAOYSA-N 0.000 claims description 2
• UZDNKJKKXDCBGT-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-methoxy-1,2,3,4-tetrahydroquinoline Chemical compound N1C2=CC=CC=C2C(OC)CC1C1=CC=C(F)C=C1 UZDNKJKKXDCBGT-UHFFFAOYSA-N 0.000 claims description 2
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
• DBXYUUYKYZXEFL-UHFFFAOYSA-N 3-methyl-2-phenyl-1,2,3,4-tetrahydro-1,5-naphthyridine Chemical compound CC1CC2=NC=CC=C2NC1C1=CC=CC=C1 DBXYUUYKYZXEFL-UHFFFAOYSA-N 0.000 claims description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• XLBQVAQDNWMICV-UHFFFAOYSA-N 4-methoxy-2-phenyl-1,2,3,4-tetrahydroquinoline Chemical compound N1C2=CC=CC=C2C(OC)CC1C1=CC=CC=C1 XLBQVAQDNWMICV-UHFFFAOYSA-N 0.000 claims description 2
• OWYBYIRQJYHJLT-UHFFFAOYSA-N 4-phenyl-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinolin-6-ol Chemical compound N1C=2C(O)=CC=CC=2C2OCCC2C1C1=CC=CC=C1 OWYBYIRQJYHJLT-UHFFFAOYSA-N 0.000 claims description 2
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• GBMXBGXKOREWBD-UHFFFAOYSA-N 5-(4-bromophenyl)-3,4,4a,5,6,10b-hexahydro-2h-pyrano[3,2-c]quinoline Chemical compound C1=CC(Br)=CC=C1C1C2CCCOC2C2=CC=CC=C2N1 GBMXBGXKOREWBD-UHFFFAOYSA-N 0.000 claims description 2
• DSFLYERGGXHKMK-UHFFFAOYSA-N 5-(4-chlorophenyl)-3,4,4a,5,6,10b-hexahydro-2h-pyrano[3,2-c]quinoline Chemical compound C1=CC(Cl)=CC=C1C1C2CCCOC2C2=CC=CC=C2N1 DSFLYERGGXHKMK-UHFFFAOYSA-N 0.000 claims description 2
• RTUBPOOBXWIPKT-UHFFFAOYSA-N 5-(4-methoxyphenyl)-3,4,4a,5,6,10b-hexahydro-2h-pyrano[3,2-c]quinoline Chemical compound C1=CC(OC)=CC=C1C1C2CCCOC2C2=CC=CC=C2N1 RTUBPOOBXWIPKT-UHFFFAOYSA-N 0.000 claims description 2
• HBOQRLPDQWQTAV-UHFFFAOYSA-N 5-phenyl-3,4,4a,5,6,10b-hexahydro-2h-pyrano[3,2-c]quinolin-7-ol Chemical compound N1C=2C(O)=CC=CC=2C2OCCCC2C1C1=CC=CC=C1 HBOQRLPDQWQTAV-UHFFFAOYSA-N 0.000 claims description 2
• KABZQPIZFDQGHN-UHFFFAOYSA-N 7-chloro-5-phenyl-3,4,4a,5,6,10b-hexahydro-2h-pyrano[3,2-c]quinoline Chemical compound N1C=2C(Cl)=CC=CC=2C2OCCCC2C1C1=CC=CC=C1 KABZQPIZFDQGHN-UHFFFAOYSA-N 0.000 claims description 2
• DWUFEZNROBRNMQ-UHFFFAOYSA-N 7-methyl-5-phenyl-3,4,4a,5,6,10b-hexahydro-2h-pyrano[3,2-c]quinoline Chemical compound N1C=2C(C)=CC=CC=2C2OCCCC2C1C1=CC=CC=C1 DWUFEZNROBRNMQ-UHFFFAOYSA-N 0.000 claims description 2
• NWWOTCODERDUTN-UHFFFAOYSA-N 8-methoxy-4-phenyl-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline Chemical compound C12CCOC2C2=CC(OC)=CC=C2NC1C1=CC=CC=C1 NWWOTCODERDUTN-UHFFFAOYSA-N 0.000 claims description 2
• KMWMLXYKAILFAQ-UHFFFAOYSA-N 9-methyl-5-phenyl-3,4,4a,5,6,10b-hexahydro-2h-pyrano[3,2-c]quinoline Chemical compound C12CCCOC2C2=CC(C)=CC=C2NC1C1=CC=CC=C1 KMWMLXYKAILFAQ-UHFFFAOYSA-N 0.000 claims description 2
• 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 2
• 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 2
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 2
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 2
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 2
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 2
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 2
• 206010024305 Leukaemia monocytic Diseases 0.000 claims description 2
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 2
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 2
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 2
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
• 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 2
• 125000005418 aryl aryl group Chemical group 0.000 claims description 2
• 230000033228 biological regulation Effects 0.000 claims description 2
• 239000004305 biphenyl Substances 0.000 claims description 2
• 235000010290 biphenyl Nutrition 0.000 claims description 2
• 210000004556 brain Anatomy 0.000 claims description 2
• 210000003679 cervix uteri Anatomy 0.000 claims description 2
• 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 claims description 2
• 210000000981 epithelium Anatomy 0.000 claims description 2
• 210000003238 esophagus Anatomy 0.000 claims description 2
• 125000002541 furyl group Chemical group 0.000 claims description 2
• 208000005017 glioblastoma Diseases 0.000 claims description 2
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 2
• 210000003734 kidney Anatomy 0.000 claims description 2
• 210000000867 larynx Anatomy 0.000 claims description 2
• 210000004185 liver Anatomy 0.000 claims description 2
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
• 201000006894 monocytic leukemia Diseases 0.000 claims description 2
• 125000001624 naphthyl group Chemical group 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
• 201000002528 pancreatic cancer Diseases 0.000 claims description 2
• 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 2
• 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims description 2
• 210000002307 prostate Anatomy 0.000 claims description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 2
• 208000000587 small cell lung carcinoma Diseases 0.000 claims description 2
• 125000004434 sulfur atom Chemical group 0.000 claims description 2
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
• 125000001544 thienyl group Chemical class 0.000 claims description 2
• 210000001685 thyroid gland Anatomy 0.000 claims description 2
• IXMSGNCKMHNZCQ-UHFFFAOYSA-N 10-chloro-5-phenyl-3,4,4a,5,6,10b-hexahydro-2h-pyrano[3,2-c]quinoline Chemical compound C12CCCOC2C=2C(Cl)=CC=CC=2NC1C1=CC=CC=C1 IXMSGNCKMHNZCQ-UHFFFAOYSA-N 0.000 claims 1
• MWWHXZPAPQDRES-UHFFFAOYSA-N 4-(4-chlorophenyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline Chemical compound C1=CC(Cl)=CC=C1C1C2CCOC2C2=CC=CC=C2N1 MWWHXZPAPQDRES-UHFFFAOYSA-N 0.000 claims 1
• LZVNOMSZAGXFQZ-UHFFFAOYSA-N 4-phenyl-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline Chemical compound O1CCC2C1C1=CC=CC=C1NC2C1=CC=CC=C1 LZVNOMSZAGXFQZ-UHFFFAOYSA-N 0.000 claims 1
• UVAODHNOAAFHMP-UHFFFAOYSA-N 8-chloro-5-phenyl-3,4,4a,5,6,10b-hexahydro-2h-pyrano[3,2-c]quinoline Chemical compound N1C2=CC(Cl)=CC=C2C2OCCCC2C1C1=CC=CC=C1 UVAODHNOAAFHMP-UHFFFAOYSA-N 0.000 claims 1
• 230000003463 hyperproliferative effect Effects 0.000 claims 1
• 210000000987 immune system Anatomy 0.000 claims 1
• 210000000936 intestine Anatomy 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 125000003107 substituted aryl group Chemical group 0.000 claims 1
• 230000000694 effects Effects 0.000 abstract description 9
• LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical class C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 abstract description 5
• 238000012360 testing method Methods 0.000 abstract description 5
• VIESAWGOYVNHLV-UHFFFAOYSA-N 1,3-dihydropyrrol-2-one Chemical compound O=C1CC=CN1 VIESAWGOYVNHLV-UHFFFAOYSA-N 0.000 abstract description 4
• 230000022131 cell cycle Effects 0.000 abstract description 4
• 125000000175 2-thienyl group Chemical class S1C([*])=C([H])C([H])=C1[H] 0.000 abstract description 2
• 230000010534 mechanism of action Effects 0.000 abstract description 2
• 125000005843 halogen group Chemical group 0.000 abstract 8
• OALXTMWCXNPUKJ-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,5-naphthyridine Chemical class C1=CN=C2CCCNC2=C1 OALXTMWCXNPUKJ-UHFFFAOYSA-N 0.000 abstract 2
• LXCHFFXACSHXRY-UHFFFAOYSA-N 1-butyl-2-thiophen-3-yl-3,4-dihydro-2H-quinoline Chemical class C(CCC)N1C(CCC2=CC=CC=C12)C1=CSC=C1 LXCHFFXACSHXRY-UHFFFAOYSA-N 0.000 abstract 2
• HGFMFKSDOFFKRV-UHFFFAOYSA-N 8h-pyrano[2,3-h]quinoline Chemical class C1=CC=NC2=C(C=CCO3)C3=CC=C21 HGFMFKSDOFFKRV-UHFFFAOYSA-N 0.000 abstract 1
• 230000004668 G2/M phase Effects 0.000 abstract 1
• 241000972349 Ocoa Species 0.000 abstract 1
• YKOWBJJOJNGCAD-SHYZEUOFSA-N [(2r,3s,5r)-3-hydroxy-5-[4-(hydroxyamino)-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl dihydrogen phosphate Chemical compound O=C1N=C(NO)C=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)C1 YKOWBJJOJNGCAD-SHYZEUOFSA-N 0.000 abstract 1
• 125000003545 alkoxy group Chemical group 0.000 abstract 1
• 125000005110 aryl thio group Chemical group 0.000 abstract 1
• 125000004104 aryloxy group Chemical group 0.000 abstract 1
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 1
• 239000000824 cytostatic agent Substances 0.000 abstract 1
• 230000001085 cytostatic effect Effects 0.000 abstract 1
• 125000004970 halomethyl group Chemical group 0.000 abstract 1
• 125000002962 imidazol-1-yl group Chemical class [*]N1C([H])=NC([H])=C1[H] 0.000 abstract 1
• 125000004283 imidazolin-2-yl group Chemical group [H]N1C(*)=NC([H])([H])C1([H])[H] 0.000 abstract 1
• 229940126261 motor protein inhibitor Drugs 0.000 abstract 1
• 229940076155 protein modulator Drugs 0.000 abstract 1
• 125000002112 pyrrolidino group Chemical class [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 abstract 1
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 42
• 235000002639 sodium chloride Nutrition 0.000 description 37
• 210000004027 cell Anatomy 0.000 description 31
• 239000000243 solution Substances 0.000 description 26
• 239000013543 active substance Substances 0.000 description 22
• 230000006907 apoptotic process Effects 0.000 description 18
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 18
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 16
• 239000008194 pharmaceutical composition Substances 0.000 description 16
• 150000003254 radicals Chemical class 0.000 description 16
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
• UBJAHGAUPNGZFF-XOVTVWCYSA-N bms-184476 Chemical compound O([C@H]1[C@@H]2[C@]3(OC(C)=O)CO[C@@H]3C[C@@H]([C@]2(C(=O)[C@H](OC(C)=O)C2=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)C=3C=CC=CC=3)C=3C=CC=CC=3)C[C@]1(O)C2(C)C)C)OCSC)C(=O)C1=CC=CC=C1 UBJAHGAUPNGZFF-XOVTVWCYSA-N 0.000 description 15
• IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 14
• 239000002585 base Substances 0.000 description 14
• 238000009472 formulation Methods 0.000 description 14
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• 102100027629 Kinesin-like protein KIF11 Human genes 0.000 description 13
• 239000000843 powder Substances 0.000 description 13
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