TWI449703B - 新穎三環化合物 - Google Patents

Info

Publication number

TWI449703B

TWI449703B TW098119270A TW98119270A TWI449703B TW I449703 B TWI449703 B TW I449703B TW 098119270 A TW098119270 A TW 098119270A TW 98119270 A TW98119270 A TW 98119270A TW I449703 B TWI449703 B TW I449703B

Authority

TW

Taiwan

Prior art keywords

optionally substituted

alkyl

cycloalkyl

group

heteroaryl

Prior art date

2008-06-10

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims description 236
• -1 -N(R a )(R b ) Chemical class 0.000 claims description 421
• 125000000623 heterocyclic group Chemical group 0.000 claims description 256
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 179
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 156
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 149
• 229910052757 nitrogen Inorganic materials 0.000 claims description 148
• 125000006573 (C1-C10) heteroaryl group Chemical group 0.000 claims description 142
• 229910052739 hydrogen Inorganic materials 0.000 claims description 136
• 239000001257 hydrogen Substances 0.000 claims description 136
• 125000006694 (C2-C10) heterocyclyl group Chemical group 0.000 claims description 111
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 107
• 150000002431 hydrogen Chemical class 0.000 claims description 102
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 85
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 83
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 76
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 74
• 229910052805 deuterium Inorganic materials 0.000 claims description 74
• 125000003118 aryl group Chemical group 0.000 claims description 69
• 229910052736 halogen Inorganic materials 0.000 claims description 69
• 150000002367 halogens Chemical class 0.000 claims description 69
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 66
• 125000001072 heteroaryl group Chemical group 0.000 claims description 62
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 57
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 51
• 125000000304 alkynyl group Chemical group 0.000 claims description 41
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 39
• 239000003814 drug Substances 0.000 claims description 34
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
• 125000004432 carbon atom Chemical group C* 0.000 claims description 31
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 31
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 29
• 229910052799 carbon Inorganic materials 0.000 claims description 29
• 150000003839 salts Chemical class 0.000 claims description 29
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
• 239000003112 inhibitor Substances 0.000 claims description 27
• 125000003342 alkenyl group Chemical group 0.000 claims description 26
• 102000004127 Cytokines Human genes 0.000 claims description 25
• 108090000695 Cytokines Proteins 0.000 claims description 25
• 125000002947 alkylene group Chemical group 0.000 claims description 25
• 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims description 24
• 239000003795 chemical substances by application Substances 0.000 claims description 24
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 24
• 230000019491 signal transduction Effects 0.000 claims description 24
• 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 22
• 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims description 21
• 239000000460 chlorine Substances 0.000 claims description 21
• 229940124597 therapeutic agent Drugs 0.000 claims description 21
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 20
• 229910052770 Uranium Inorganic materials 0.000 claims description 20
• 125000000217 alkyl group Chemical group 0.000 claims description 20
• CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims description 20
• 239000005557 antagonist Substances 0.000 claims description 19
• OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims description 19
• FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 claims description 18
• 210000001744 T-lymphocyte Anatomy 0.000 claims description 18
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 claims description 17
• GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims description 17
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 17
• 108010065805 Interleukin-12 Proteins 0.000 claims description 16
• 102000013462 Interleukin-12 Human genes 0.000 claims description 16
• FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 16
• 229960000485 methotrexate Drugs 0.000 claims description 16
• UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 claims description 15
• 229960002170 azathioprine Drugs 0.000 claims description 15
• 229960001940 sulfasalazine Drugs 0.000 claims description 15
• NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 claims description 15
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 14
• 102000000589 Interleukin-1 Human genes 0.000 claims description 14
• 108010002352 Interleukin-1 Proteins 0.000 claims description 14
• 239000003246 corticosteroid Substances 0.000 claims description 14
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 14
• 229910052717 sulfur Inorganic materials 0.000 claims description 14
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 14
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 13
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
• 239000011724 folic acid Substances 0.000 claims description 13
• 235000019152 folic acid Nutrition 0.000 claims description 13
• 239000001301 oxygen Substances 0.000 claims description 13
• XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims description 13
• 229960004618 prednisone Drugs 0.000 claims description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
• NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 claims description 12
• PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 12
• 108010036949 Cyclosporine Proteins 0.000 claims description 12
• 102000004388 Interleukin-4 Human genes 0.000 claims description 12
• 108090000978 Interleukin-4 Proteins 0.000 claims description 12
• 229960001265 ciclosporin Drugs 0.000 claims description 12
• 229960001334 corticosteroids Drugs 0.000 claims description 12
• RMRCNWBMXRMIRW-BYFNXCQMSA-M cyanocobalamin Chemical compound N#C[Co+]N([C@]1([H])[C@H](CC(N)=O)[C@]\2(CCC(=O)NC[C@H](C)OP(O)(=O)OC3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)C)C/2=C(C)\C([C@H](C/2(C)C)CCC(N)=O)=N\C\2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O RMRCNWBMXRMIRW-BYFNXCQMSA-M 0.000 claims description 12
• 229930182912 cyclosporin Natural products 0.000 claims description 12
• 229960001193 diclofenac sodium Drugs 0.000 claims description 12
• 229960004584 methylprednisolone Drugs 0.000 claims description 12
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
• 102000005962 receptors Human genes 0.000 claims description 12
• JGMJQSFLQWGYMQ-UHFFFAOYSA-M sodium;2,6-dichloro-n-phenylaniline;acetate Chemical compound [Na+].CC([O-])=O.ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 JGMJQSFLQWGYMQ-UHFFFAOYSA-M 0.000 claims description 12
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 11
• 239000005541 ACE inhibitor Substances 0.000 claims description 11
• HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 11
• CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 11
• 125000004429 atom Chemical group 0.000 claims description 11
• DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 11
• 229960001259 diclofenac Drugs 0.000 claims description 11
• 229960001680 ibuprofen Drugs 0.000 claims description 11
• OJLOPKGSLYJEMD-URPKTTJQSA-N methyl 7-[(1r,2r,3r)-3-hydroxy-2-[(1e)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate Chemical compound CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC OJLOPKGSLYJEMD-URPKTTJQSA-N 0.000 claims description 11
• 229960005249 misoprostol Drugs 0.000 claims description 11
• 229960002009 naproxen Drugs 0.000 claims description 11
• CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 11
• 150000003222 pyridines Chemical class 0.000 claims description 11
• 108020003175 receptors Proteins 0.000 claims description 11
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 11
• 125000006586 (C3-C10) cycloalkylene group Chemical group 0.000 claims description 10
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 10
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 10
• 108090000426 Caspase-1 Proteins 0.000 claims description 10
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• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 10
• QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 claims description 10
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• VHOGYURTWQBHIL-UHFFFAOYSA-N leflunomide Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)=C1C VHOGYURTWQBHIL-UHFFFAOYSA-N 0.000 claims description 10
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• 229960004963 mesalazine Drugs 0.000 claims description 10
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• 102000003815 Interleukin-11 Human genes 0.000 claims description 9
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• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 9
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 9
• 125000002393 azetidinyl group Chemical group 0.000 claims description 9
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
• 229960000681 leflunomide Drugs 0.000 claims description 9
• 239000003446 ligand Substances 0.000 claims description 9
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• 150000003053 piperidines Chemical class 0.000 claims description 9
• RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 claims description 9
• 229960000371 rofecoxib Drugs 0.000 claims description 9
• QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 claims description 9
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 8
• 101000914484 Homo sapiens T-lymphocyte activation antigen CD80 Proteins 0.000 claims description 8
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• 108010050904 Interferons Proteins 0.000 claims description 8
• 102100027222 T-lymphocyte activation antigen CD80 Human genes 0.000 claims description 8
• MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims description 8
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
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• 229960003957 dexamethasone Drugs 0.000 claims description 8
• UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 8
• 229940079322 interferon Drugs 0.000 claims description 8
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• YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 claims description 8
• 229960002117 triamcinolone acetonide Drugs 0.000 claims description 8
• LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 claims description 8
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• RTGDFNSFWBGLEC-SYZQJQIISA-N mycophenolate mofetil Chemical compound COC1=C(C)C=2COC(=O)C=2C(O)=C1C\C=C(/C)CCC(=O)OCCN1CCOCC1 RTGDFNSFWBGLEC-SYZQJQIISA-N 0.000 claims description 7
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• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
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