ES2392489T3 - Dicarbazoles y procedimientos de uso - Google Patents

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Publication number

ES2392489T3

ES2392489T3 ES09762885T ES09762885T ES2392489T3 ES 2392489 T3 ES2392489 T3 ES 2392489T3 ES 09762885 T ES09762885 T ES 09762885T ES 09762885 T ES09762885 T ES 09762885T ES 2392489 T3 ES2392489 T3 ES 2392489T3

Authority

ES

Spain

Prior art keywords

alkyl

cr14r15

groups

aryl

heteroaryl

Prior art date

2008-06-11

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.)

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• 238000000034 method Methods 0.000 title claims description 91
• 150000001875 compounds Chemical class 0.000 claims abstract description 257
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 132
• 125000003118 aryl group Chemical group 0.000 claims abstract description 93
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 89
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 78
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 74
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 63
• 150000002367 halogens Chemical class 0.000 claims abstract description 57
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 47
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 45
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 40
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 39
• 150000003839 salts Chemical class 0.000 claims abstract description 37
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 35
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 32
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 32
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 31
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 29
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 21
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 21
• 125000004429 atom Chemical group 0.000 claims abstract description 20
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 19
• 239000012453 solvate Substances 0.000 claims abstract description 19
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims abstract description 15
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 14
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims abstract description 13
• 125000005843 halogen group Chemical group 0.000 claims abstract description 13
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims abstract description 12
• 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims abstract description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
• 101100173726 Arabidopsis thaliana OR23 gene Proteins 0.000 claims abstract description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
• -1 furanoyl Chemical group 0.000 claims description 111
• 206010028980 Neoplasm Diseases 0.000 claims description 37
• 241000124008 Mammalia Species 0.000 claims description 26
• 201000011510 cancer Diseases 0.000 claims description 26
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
• 239000002246 antineoplastic agent Substances 0.000 claims description 19
• 229940127089 cytotoxic agent Drugs 0.000 claims description 19
• 125000002619 bicyclic group Chemical group 0.000 claims description 18
• 208000035475 disorder Diseases 0.000 claims description 18
• 238000011282 treatment Methods 0.000 claims description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 13
• 239000003795 chemical substances by application Substances 0.000 claims description 12
• 230000010261 cell growth Effects 0.000 claims description 11
• 230000002401 inhibitory effect Effects 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 230000002159 abnormal effect Effects 0.000 claims description 10
• 230000003463 hyperproliferative effect Effects 0.000 claims description 10
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• 206010009944 Colon cancer Diseases 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 8
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 7
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 7
• 206010025323 Lymphomas Diseases 0.000 claims description 7
• 206010033128 Ovarian cancer Diseases 0.000 claims description 7
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 7
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 7
• 206010039491 Sarcoma Diseases 0.000 claims description 7
• 208000032839 leukemia Diseases 0.000 claims description 7
• 201000001441 melanoma Diseases 0.000 claims description 7
• 201000000050 myeloid neoplasm Diseases 0.000 claims description 7
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 7
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 7
• 206010006187 Breast cancer Diseases 0.000 claims description 6
• 208000026310 Breast neoplasm Diseases 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 6
• 230000006378 damage Effects 0.000 claims description 5
• 125000006413 ring segment Chemical group 0.000 claims description 5
• BQMPGKPTOHKYHS-UHFFFAOYSA-N 1h-pyrrole-2-carbonitrile Chemical compound N#CC1=CC=CN1 BQMPGKPTOHKYHS-UHFFFAOYSA-N 0.000 claims description 4
• 229910006074 SO2NH2 Inorganic materials 0.000 claims description 4
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• JZXCUAXRQTZRMK-UHFFFAOYSA-N 4-chloro-8-[4-(4-methylpiperazin-1-yl)phenyl]-2-(1-methylpyrazol-4-yl)-5h-pyrido[2,3]pyrrolo[2,4-b]pyrimidine Chemical compound C1CN(C)CCN1C1=CC=C(C=2C=C3C4=NC(=NC(Cl)=C4NC3=NC=2)C2=CN(C)N=C2)C=C1 JZXCUAXRQTZRMK-UHFFFAOYSA-N 0.000 claims description 3
• DDGVPZWMJCOHFQ-UHFFFAOYSA-N 4-chloro-8-[4-(4-methylpiperazin-1-yl)phenyl]-2-(2-methylpyrazol-3-yl)-5h-pyrido[2,3]pyrrolo[2,4-b]pyrimidine Chemical compound C1CN(C)CCN1C1=CC=C(C=2C=C3C4=NC(=NC(Cl)=C4NC3=NC=2)C=2N(N=CC=2)C)C=C1 DDGVPZWMJCOHFQ-UHFFFAOYSA-N 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• SUZJJFSEMWCPNP-UHFFFAOYSA-N 12-[4-(4-methylpiperazin-1-yl)phenyl]-4-(1-methylpyrazol-3-yl)-3,5,8,10-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,10,12-pentaen-6-one Chemical compound CN1CCN(CC1)c1ccc(cc1)-c1cnc2[nH]c3c(nc([nH]c3=O)-c3ccn(C)n3)c2c1 SUZJJFSEMWCPNP-UHFFFAOYSA-N 0.000 claims description 2
• TXNDZVYZZLWBTK-UHFFFAOYSA-N 12-bromo-4-(1-methylpyrazol-3-yl)-3,5,8,10-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,10,12-pentaen-6-one Chemical compound Cn1ccc(n1)-c1nc2c3cc(Br)cnc3[nH]c2c(=O)[nH]1 TXNDZVYZZLWBTK-UHFFFAOYSA-N 0.000 claims description 2
• YCWZHHSOULJUNZ-UHFFFAOYSA-N 12-bromo-4-(2-methylpyrazol-3-yl)-3,5,8,10-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,10,12-pentaen-6-one Chemical compound Cn1nccc1-c1nc2c3cc(Br)cnc3[nH]c2c(=O)[nH]1 YCWZHHSOULJUNZ-UHFFFAOYSA-N 0.000 claims description 2
• SVWXFUREAWPDOW-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-8-[4-(piperidin-1-ylmethyl)phenyl]-1,5-dihydropyrido[2,3]pyrrolo[2,4-b]pyrimidin-4-one Chemical compound C1=NN(C)C=C1C(N1)=NC(=O)C2=C1C1=CC(C=3C=CC(CN4CCCCC4)=CC=3)=CN=C1N2 SVWXFUREAWPDOW-UHFFFAOYSA-N 0.000 claims description 2
• QZLMKMURPTUNHK-UHFFFAOYSA-N 2-[1-[(4-methoxyphenyl)methyl]pyrazol-4-yl]-8-[4-(4-methylpiperazin-1-yl)phenyl]-1,5-dihydropyrido[2,3]pyrrolo[2,4-b]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1CN1N=CC(C=2NC=3C4=CC(=CN=C4NC=3C(=O)N=2)C=2C=CC(=CC=2)N2CCN(C)CC2)=C1 QZLMKMURPTUNHK-UHFFFAOYSA-N 0.000 claims description 2
• TWZOGBRUQMLDLI-UHFFFAOYSA-N 4-chloro-8-[4-(4-methylpiperazin-1-yl)phenyl]-2-(1h-pyrazol-4-yl)-5h-pyrido[2,3]pyrrolo[2,4-b]pyrimidine Chemical compound C1CN(C)CCN1C1=CC=C(C=2C=C3C4=NC(=NC(Cl)=C4NC3=NC=2)C2=CNN=C2)C=C1 TWZOGBRUQMLDLI-UHFFFAOYSA-N 0.000 claims description 2
• PVFMWZKSCAHMFL-UHFFFAOYSA-N 4-chloro-8-[4-(4-methylpiperazin-1-yl)phenyl]-2-pyridin-3-yl-5h-pyrido[2,3]pyrrolo[2,4-b]pyrimidine Chemical compound C1CN(C)CCN1C1=CC=C(C=2C=C3C4=NC(=NC(Cl)=C4NC3=NC=2)C=2C=NC=CC=2)C=C1 PVFMWZKSCAHMFL-UHFFFAOYSA-N 0.000 claims description 2
• HXIPOURWZRATPT-UHFFFAOYSA-N 4-methyl-8-[4-(4-methylpiperazin-1-yl)phenyl]-2-(1-methylpyrazol-4-yl)-5h-pyrido[4,5]pyrrolo[1,2-d]pyrimidine Chemical compound C1CN(C)CCN1C1=CC=C(C=2C=C3C4=NC(=NC(C)=C4NC3=NC=2)C2=CN(C)N=C2)C=C1 HXIPOURWZRATPT-UHFFFAOYSA-N 0.000 claims description 2
• UHPKDZSLPXKOFD-UHFFFAOYSA-N 8-[4-(4-methylpiperazin-1-yl)phenyl]-2-(1-methylpyrazol-4-yl)-1,5-dihydropyrido[2,3]pyrrolo[2,4-b]pyrimidin-4-one Chemical compound C1CN(C)CCN1C1=CC=C(C=2C=C3C4=C(C(N=C(N4)C4=CN(C)N=C4)=O)NC3=NC=2)C=C1 UHPKDZSLPXKOFD-UHFFFAOYSA-N 0.000 claims description 2
• HMVHRSIRUWIFMC-UHFFFAOYSA-N 8-[4-(4-methylpiperazin-1-yl)phenyl]-2-(2-methylpyrazol-3-yl)-5h-pyrido[4,5]pyrrolo[1,2-d]pyrimidine Chemical compound C1CN(C)CCN1C1=CC=C(C=2C=C3C4=NC(=NC=C4NC3=NC=2)C=2N(N=CC=2)C)C=C1 HMVHRSIRUWIFMC-UHFFFAOYSA-N 0.000 claims description 2
• UAIMRIUSFMTVER-UHFFFAOYSA-N 8-bromo-2-(1-methylpyrazol-4-yl)-1,5-dihydropyrido[2,3]pyrrolo[2,4-b]pyrimidin-4-one Chemical compound C1=NN(C)C=C1C(N1)=NC(=O)C2=C1C1=CC(Br)=CN=C1N2 UAIMRIUSFMTVER-UHFFFAOYSA-N 0.000 claims description 2
• YOPLIAQFMNTBFT-UHFFFAOYSA-N 8-bromo-2-pyridin-3-yl-1,5-dihydropyrido[2,3]pyrrolo[2,4-b]pyrimidin-4-one Chemical compound C12=CC(Br)=CN=C2NC(C(N=2)=O)=C1NC=2C1=CC=CN=C1 YOPLIAQFMNTBFT-UHFFFAOYSA-N 0.000 claims description 2
• OTWLWCNHDNQNFV-UHFFFAOYSA-N 4-chloro-2-(1-methylpyrazol-4-yl)-8-[4-(piperidin-1-ylmethyl)phenyl]-5h-pyrido[2,3]pyrrolo[2,4-b]pyrimidine Chemical compound C1=NN(C)C=C1C1=NC(Cl)=C(NC=2C3=CC(=CN=2)C=2C=CC(CN4CCCCC4)=CC=2)C3=N1 OTWLWCNHDNQNFV-UHFFFAOYSA-N 0.000 claims 1
• QIAOHWLWXSYDSV-UHFFFAOYSA-N 8-[4-(4-methylpiperazin-1-yl)phenyl]-2-pyridin-3-yl-1,5-dihydropyrido[2,3]pyrrolo[2,4-b]pyrimidin-4-one Chemical compound C1CN(C)CCN1C1=CC=C(C=2C=C3C4=C(C(N=C(N4)C=4C=NC=CC=4)=O)NC3=NC=2)C=C1 QIAOHWLWXSYDSV-UHFFFAOYSA-N 0.000 claims 1
• HWGYMVNWFRGPOC-UHFFFAOYSA-N 8-bromo-2-[1-[(4-methoxyphenyl)methyl]pyrazol-4-yl]-1,5-dihydropyrido[2,3]pyrrolo[2,4-b]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1CN1N=CC(C=2NC=3C4=CC(Br)=CN=C4NC=3C(=O)N=2)=C1 HWGYMVNWFRGPOC-UHFFFAOYSA-N 0.000 claims 1
• IFGGMDIZTDIOSI-UHFFFAOYSA-N CN1CCN(CC1)C1=CC=C(C=C1)C=1C=NC=2NC3=CN=C(N=C3C2C1)C=1C=NN(C1)C.CN1CCN(CC1)C1=CC=C(C=C1)C=1C=NC=2NC3=CN=C(N=C3C2C1)C=1C=NC=CC1 Chemical compound CN1CCN(CC1)C1=CC=C(C=C1)C=1C=NC=2NC3=CN=C(N=C3C2C1)C=1C=NN(C1)C.CN1CCN(CC1)C1=CC=C(C=C1)C=1C=NC=2NC3=CN=C(N=C3C2C1)C=1C=NC=CC1 IFGGMDIZTDIOSI-UHFFFAOYSA-N 0.000 claims 1
• 239000002904 solvent Substances 0.000 description 106
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 63
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 62
• 239000000203 mixture Substances 0.000 description 56
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
• 239000002585 base Substances 0.000 description 39
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 38
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 33
• 238000006243 chemical reaction Methods 0.000 description 33
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 31
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
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• 239000002253 acid Substances 0.000 description 24
• 239000003054 catalyst Substances 0.000 description 23
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• 239000003112 inhibitor Substances 0.000 description 18
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• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
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• 239000000543 intermediate Substances 0.000 description 15
• 125000004043 oxo group Chemical group O=* 0.000 description 15
• 125000006239 protecting group Chemical group 0.000 description 15
• 101150050673 CHK1 gene Proteins 0.000 description 14
• 150000004677 hydrates Chemical class 0.000 description 14
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 14
• 125000001424 substituent group Chemical group 0.000 description 14
• 239000000243 solution Substances 0.000 description 13
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• 125000004432 carbon atom Chemical group C* 0.000 description 10
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 10
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