JP2009542608A5

JP2009542608A5 -

Info

Publication number: JP2009542608A5
Authority: JP; Japan
Prior art keywords: acid; compound; group; optionally; aurora
Prior art date: 2007-06-29
Legal status : Pending

Application number

JP2009517403A

Other languages

English (en)

Japanese (ja)

Other versions

JP2009542608A (ja

Filing date

2007-06-29

Publication date

2011-09-08

2007-06-29 Application filed filed Critical

2007-06-29 Priority claimed from PCT/GB2007/002428 external-priority patent/WO2008001101A2/en

2009-12-03 Publication of JP2009542608A publication Critical patent/JP2009542608A/ja

2011-09-08 Publication of JP2009542608A5 publication Critical patent/JP2009542608A5/ja

Status Pending legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 170
-1 cyano, nitro, carboxy, amino Chemical group 0.000 claims description 138
229910052739 hydrogen Inorganic materials 0.000 claims description 86
239000001257 hydrogen Substances 0.000 claims description 86
150000003839 salts Chemical class 0.000 claims description 80
125000000217 alkyl group Chemical group 0.000 claims description 68
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 67
125000000623 heterocyclic group Chemical group 0.000 claims description 62
125000003545 alkoxy group Chemical group 0.000 claims description 61
125000001183 hydrocarbyl group Chemical group 0.000 claims description 54
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 54
229910052736 halogen Inorganic materials 0.000 claims description 48
150000002367 halogens Chemical class 0.000 claims description 48
239000002253 acid Substances 0.000 claims description 46
201000010099 disease Diseases 0.000 claims description 46
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 46
229910052760 oxygen Inorganic materials 0.000 claims description 45
239000011737 fluorine Substances 0.000 claims description 44
229910052731 fluorine Inorganic materials 0.000 claims description 44
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 43
125000001424 substituent group Chemical group 0.000 claims description 43
230000002265 prevention Effects 0.000 claims description 39
229910005965 SO 2 Inorganic materials 0.000 claims description 38
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
239000003112 inhibitor Substances 0.000 claims description 35
125000002837 carbocyclic group Chemical group 0.000 claims description 32
229910052717 sulfur Inorganic materials 0.000 claims description 32
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
230000003827 upregulation Effects 0.000 claims description 30
102000003989 Aurora kinases Human genes 0.000 claims description 29
108090000433 Aurora kinases Proteins 0.000 claims description 29
241000124008 Mammalia Species 0.000 claims description 29
239000003795 chemical substances by application Substances 0.000 claims description 27
239000000460 chlorine Substances 0.000 claims description 26
229910052801 chlorine Inorganic materials 0.000 claims description 26
206010028980 Neoplasm Diseases 0.000 claims description 25
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
239000003814 drug Substances 0.000 claims description 24
201000011510 cancer Diseases 0.000 claims description 23
238000002405 diagnostic procedure Methods 0.000 claims description 22
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
239000012453 solvate Substances 0.000 claims description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 20
108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims description 19
102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 claims description 19
150000001204 N-oxides Chemical class 0.000 claims description 19
102000004000 Aurora Kinase A Human genes 0.000 claims description 18
108090000461 Aurora Kinase A Proteins 0.000 claims description 18
102000004228 Aurora kinase B Human genes 0.000 claims description 18
108090000749 Aurora kinase B Proteins 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 18
125000005842 heteroatom Chemical group 0.000 claims description 18
239000008194 pharmaceutical composition Substances 0.000 claims description 17
230000002159 abnormal effect Effects 0.000 claims description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 15
150000002431 hydrogen Chemical class 0.000 claims description 15
230000002401 inhibitory effect Effects 0.000 claims description 15
108090000266 Cyclin-dependent kinases Proteins 0.000 claims description 14
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LOLPPWBBNUVNQZ-UHFFFAOYSA-N chembl495727 Chemical compound C=1NN=C(C=2NC3=CC=C(CN4CCOCC4)C=C3N=2)C=1NC(=O)NC1CC1 LOLPPWBBNUVNQZ-UHFFFAOYSA-N 0.000 claims description 14
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 13
108091007914 CDKs Proteins 0.000 claims description 12
QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 claims description 12
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 12
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 12
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 12
125000004663 dialkyl amino group Chemical group 0.000 claims description 12
125000001153 fluoro group Chemical group F* 0.000 claims description 12
AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical group FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 12
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230000000694 effects Effects 0.000 claims description 11
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229910052757 nitrogen Inorganic materials 0.000 claims description 10
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FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 9
ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims description 9
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 9
229940100198 alkylating agent Drugs 0.000 claims description 9
239000002168 alkylating agent Substances 0.000 claims description 9
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239000000203 mixture Substances 0.000 claims description 9
150000003058 platinum compounds Chemical class 0.000 claims description 9
WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 claims description 8
KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 claims description 8
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 8
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 8
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 8
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
229940122803 Vinca alkaloid Drugs 0.000 claims description 8
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
238000002648 combination therapy Methods 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 8
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 8
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 8
229940121372 histone deacetylase inhibitor Drugs 0.000 claims description 8
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 8
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XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 claims description 8
PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 claims description 8
ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims description 7
101710160107 Outer membrane protein A Proteins 0.000 claims description 7
235000011054 acetic acid Nutrition 0.000 claims description 7
125000003282 alkyl amino group Chemical group 0.000 claims description 7
229940127093 camptothecin Drugs 0.000 claims description 7
229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 claims description 7
VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims description 7
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 6
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RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 6
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101710183280 Topoisomerase Proteins 0.000 claims description 6
239000001361 adipic acid Substances 0.000 claims description 6
235000011037 adipic acid Nutrition 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 6
239000005441 aurora Substances 0.000 claims description 6
239000004202 carbamide Substances 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
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125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 5
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims description 5
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KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 5
229940123237 Taxane Drugs 0.000 claims description 5
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125000001309 chloro group Chemical group Cl* 0.000 claims description 5
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125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 5
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229940098779 methanesulfonic acid Drugs 0.000 claims description 5
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 5
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 5
230000037361 pathway Effects 0.000 claims description 5
239000008117 stearic acid Substances 0.000 claims description 5
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 4
LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 claims description 4
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125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 4
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125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
KDKUVYLMPJIGKA-UHFFFAOYSA-N 4-[[5-amino-1-[(2,6-difluorophenyl)-oxomethyl]-1,2,4-triazol-3-yl]amino]benzenesulfonamide Chemical compound N=1N(C(=O)C=2C(=CC=CC=2F)F)C(N)=NC=1NC1=CC=C(S(N)(=O)=O)C=C1 KDKUVYLMPJIGKA-UHFFFAOYSA-N 0.000 claims description 4
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 4
BFYIZQONLCFLEV-DAELLWKTSA-N Aromasine Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 BFYIZQONLCFLEV-DAELLWKTSA-N 0.000 claims description 4
239000005711 Benzoic acid Substances 0.000 claims description 4
239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 claims description 4
IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims description 4
239000005642 Oleic acid Substances 0.000 claims description 4
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 4
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235000021314 Palmitic acid Nutrition 0.000 claims description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
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BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 4
229960002932 anastrozole Drugs 0.000 claims description 4
YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 claims description 4
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239000002256 antimetabolite Substances 0.000 claims description 4
235000010233 benzoic acid Nutrition 0.000 claims description 4
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229910052799 carbon Inorganic materials 0.000 claims description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 4
230000032823 cell division Effects 0.000 claims description 4
230000033077 cellular process Effects 0.000 claims description 4
239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 claims description 4
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 claims description 4
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 claims description 4
229940043264 dodecyl sulfate Drugs 0.000 claims description 4
AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 claims description 4
229960000255 exemestane Drugs 0.000 claims description 4
DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 claims description 4
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125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
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JP2009517403A 2006-06-29 2007-06-29 医薬組合せ剤 Pending JP2009542608A (ja)