PT1732926E - Inibidores de cinesinas mitóticas - Google Patents

Info

Publication number

PT1732926E

PT1732926E PT05732607T PT05732607T PT1732926E PT 1732926 E PT1732926 E PT 1732926E PT 05732607 T PT05732607 T PT 05732607T PT 05732607 T PT05732607 T PT 05732607T PT 1732926 E PT1732926 E PT 1732926E

Authority

PT

Portugal

Prior art keywords

quot

group

compound

alkyl

pyrido

Prior art date

2004-04-06

Links

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• Global Dossier
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• 108010063296 Kinesin Proteins 0.000 title claims description 13
• 102000010638 Kinesin Human genes 0.000 title claims description 13
• 239000003112 inhibitor Substances 0.000 title description 25
• 230000000394 mitotic effect Effects 0.000 title description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 162
• 239000000203 mixture Substances 0.000 claims abstract description 80
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 46
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 31
• 201000011510 cancer Diseases 0.000 claims abstract description 29
• 201000010099 disease Diseases 0.000 claims abstract description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
• 230000001404 mediated effect Effects 0.000 claims abstract description 11
• -1 substituted Chemical group 0.000 claims description 129
• 125000000217 alkyl group Chemical group 0.000 claims description 72
• 125000003118 aryl group Chemical group 0.000 claims description 49
• 125000000623 heterocyclic group Chemical group 0.000 claims description 41
• 238000011282 treatment Methods 0.000 claims description 39
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims description 24
• 239000001257 hydrogen Substances 0.000 claims description 24
• 239000003795 chemical substances by application Substances 0.000 claims description 21
• 239000003814 drug Substances 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 18
• 150000003839 salts Chemical class 0.000 claims description 15
• 208000035475 disorder Diseases 0.000 claims description 14
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 230000004663 cell proliferation Effects 0.000 claims description 12
• 239000003937 drug carrier Substances 0.000 claims description 11
• 125000000304 alkynyl group Chemical group 0.000 claims description 10
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 8
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 8
• 239000005517 L01XE01 - Imatinib Substances 0.000 claims description 8
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 8
• KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 claims description 8
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 6
• 150000002431 hydrogen Chemical class 0.000 claims description 6
• UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims description 6
• 210000000244 kidney pelvis Anatomy 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 229960000575 trastuzumab Drugs 0.000 claims description 6
• 125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 claims description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
• PNNDGLXCMNOPHN-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-2-yl)-2-methylpropyl]-4-methylbenzamide Chemical compound N1=C2CCCCN2C(=O)C(CC=2C=CC=CC=2)=C1C(C(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 PNNDGLXCMNOPHN-UHFFFAOYSA-N 0.000 claims description 5
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 5
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 4
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 4
• 208000034578 Multiple myelomas Diseases 0.000 claims description 4
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 4
• ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 4
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 4
• 229930012538 Paclitaxel Natural products 0.000 claims description 4
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 4
• 210000004556 brain Anatomy 0.000 claims description 4
• 210000000481 breast Anatomy 0.000 claims description 4
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 4
• 229960004316 cisplatin Drugs 0.000 claims description 4
• 210000003238 esophagus Anatomy 0.000 claims description 4
• 229960002949 fluorouracil Drugs 0.000 claims description 4
• 229960002411 imatinib Drugs 0.000 claims description 4
• 229960004768 irinotecan Drugs 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 229960001592 paclitaxel Drugs 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 229960004641 rituximab Drugs 0.000 claims description 4
• 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 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 claims description 3
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 3
• 208000028018 Lymphocytic leukaemia Diseases 0.000 claims description 3
• 229930013930 alkaloid Natural products 0.000 claims description 3
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
• 229940045799 anthracyclines and related substance Drugs 0.000 claims description 3
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
• VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims description 3
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
• 208000035269 cancer or benign tumor Diseases 0.000 claims description 3
• 229960004562 carboplatin Drugs 0.000 claims description 3
• 210000003679 cervix uteri Anatomy 0.000 claims description 3
• 210000001072 colon Anatomy 0.000 claims description 3
• 229960004397 cyclophosphamide Drugs 0.000 claims description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• 229960003668 docetaxel Drugs 0.000 claims description 3
• VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 claims description 3
• 235000008191 folinic acid Nutrition 0.000 claims description 3
• 239000011672 folinic acid Substances 0.000 claims description 3
• 210000003228 intrahepatic bile duct Anatomy 0.000 claims description 3
• 210000000867 larynx Anatomy 0.000 claims description 3
• 229960001691 leucovorin Drugs 0.000 claims description 3
• 210000004185 liver Anatomy 0.000 claims description 3
• 210000004072 lung Anatomy 0.000 claims description 3
• 208000003747 lymphoid leukemia Diseases 0.000 claims description 3
• 201000001441 melanoma Diseases 0.000 claims description 3
• 210000000214 mouth Anatomy 0.000 claims description 3
• 208000025113 myeloid leukemia Diseases 0.000 claims description 3
• PNJJTYFWKNHNAA-UHFFFAOYSA-N n-[1-(3-benzyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-2-yl)-2-methylpropyl]-4-methyl-n-[3-(methylamino)propyl]benzamide Chemical compound C=1C=C(C)C=CC=1C(=O)N(CCCNC)C(C(C)C)C=1N=C2CCCCN2C(=O)C=1CC1=CC=CC=C1 PNJJTYFWKNHNAA-UHFFFAOYSA-N 0.000 claims description 3
• 210000001672 ovary Anatomy 0.000 claims description 3
• 210000000496 pancreas Anatomy 0.000 claims description 3
• 210000003800 pharynx Anatomy 0.000 claims description 3
• 210000002307 prostate Anatomy 0.000 claims description 3
• 210000000664 rectum Anatomy 0.000 claims description 3
• 210000000813 small intestine Anatomy 0.000 claims description 3
• 210000002784 stomach Anatomy 0.000 claims description 3
• 229950006410 tezacitabine Drugs 0.000 claims description 3
• GFFXZLZWLOBBLO-ASKVSEFXSA-N tezacitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 GFFXZLZWLOBBLO-ASKVSEFXSA-N 0.000 claims description 3
• 210000001685 thyroid gland Anatomy 0.000 claims description 3
• UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims description 3
• 229960000303 topotecan Drugs 0.000 claims description 3
• 210000004291 uterus Anatomy 0.000 claims description 3
• 208000024051 villous adenoma of colon Diseases 0.000 claims description 3
• 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 2
• 241000863480 Vinca Species 0.000 claims description 2
• 229940122803 Vinca alkaloid Drugs 0.000 claims description 2
• 229960005277 gemcitabine Drugs 0.000 claims description 2
• SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims description 2
• BWZYNWCMTYBERI-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-2-yl)-2-methylpropyl]-3-fluoro-4-methylbenzamide Chemical compound N1=C2CCCCN2C(=O)C(CC=2C=CC=CC=2)=C1C(C(C)C)N(CCCN)C(=O)C1=CC=C(C)C(F)=C1 BWZYNWCMTYBERI-UHFFFAOYSA-N 0.000 claims description 2
• HEATZYKZKIPBCT-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-8-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-2-yl)propyl]-4-methylbenzamide Chemical compound N1=C2CC(C)CCN2C(=O)C(CC=2C=CC=CC=2)=C1C(CC)N(CCCN)C(=O)C1=CC=C(C)C=C1 HEATZYKZKIPBCT-UHFFFAOYSA-N 0.000 claims description 2
• XXHQDSFHABTCHE-UHFFFAOYSA-N n-[1-(3-benzyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-2-yl)-2-methylpropyl]-n-[3-(ethylamino)propyl]-3-fluoro-4-methylbenzamide Chemical compound C=1C=C(C)C(F)=CC=1C(=O)N(CCCNCC)C(C(C)C)C=1N=C2CCCCN2C(=O)C=1CC1=CC=CC=C1 XXHQDSFHABTCHE-UHFFFAOYSA-N 0.000 claims description 2
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