JP2008529989A5 - - Google Patents
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- JP2008529989A5 JP2008529989A5 JP2007553625A JP2007553625A JP2008529989A5 JP 2008529989 A5 JP2008529989 A5 JP 2008529989A5 JP 2007553625 A JP2007553625 A JP 2007553625A JP 2007553625 A JP2007553625 A JP 2007553625A JP 2008529989 A5 JP2008529989 A5 JP 2008529989A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridine
- cyano
- dihydro
- thieno
- carboxylic acid
- Prior art date
- 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.)
- Pending
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- -1 2,3-dihydro-1,4-benzodioxinyl Chemical group 0.000 claims 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 16
- 125000004076 pyridyl group Chemical group 0.000 claims 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 13
- 125000004432 carbon atom Chemical group C* 0.000 claims 13
- 229910052801 chlorine Inorganic materials 0.000 claims 13
- 239000000460 chlorine Substances 0.000 claims 13
- 229910052799 carbon Inorganic materials 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 11
- 229910052731 fluorine Inorganic materials 0.000 claims 10
- 239000011737 fluorine Substances 0.000 claims 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- SXTYQHGVUDWKMX-UHFFFAOYSA-N 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylic acid Chemical compound C1N(C(=O)O)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=N1 SXTYQHGVUDWKMX-UHFFFAOYSA-N 0.000 claims 6
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims 6
- 125000004122 cyclic group Chemical group 0.000 claims 6
- 150000002148 esters Chemical class 0.000 claims 6
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- 239000002246 antineoplastic agent Substances 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 125000002541 furyl group Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000001544 thienyl group Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 230000003796 beauty Effects 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims 3
- HJUKZVDEKGIRHY-UHFFFAOYSA-N 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylic acid Chemical compound S1C=2CN(C(O)=O)CCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC=C1 HJUKZVDEKGIRHY-UHFFFAOYSA-N 0.000 claims 3
- ASLOEHSOKOANTH-UHFFFAOYSA-N 3-cyano-2-(3-pyridin-3-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylic acid Chemical compound S1C=2CN(C(O)=O)CCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CN=C1 ASLOEHSOKOANTH-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 239000000556 agonist Substances 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- FIKYVUYVAGBVGL-UHFFFAOYSA-N ethyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1 FIKYVUYVAGBVGL-UHFFFAOYSA-N 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 3
- LLKVZVINYADQJG-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC(=O)OC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=N1 LLKVZVINYADQJG-UHFFFAOYSA-N 0.000 claims 2
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims 2
- QAZBYKUZGBGZTD-UHFFFAOYSA-N 2,3-dihydroxypropyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC(O)CO)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=N1 QAZBYKUZGBGZTD-UHFFFAOYSA-N 0.000 claims 2
- KXGRJVLZEWQYEL-UHFFFAOYSA-N 2-[3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carbonyl]oxyacetic acid Chemical compound C1N(C(=O)OCC(=O)O)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=N1 KXGRJVLZEWQYEL-UHFFFAOYSA-N 0.000 claims 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- DEFLRAIQDAMFIB-UHFFFAOYSA-N 2-hydroxyethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCCO)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=N1 DEFLRAIQDAMFIB-UHFFFAOYSA-N 0.000 claims 2
- IDXDMHGZQWHGAV-UHFFFAOYSA-N 2-imidazol-1-ylethyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCN3C=NC=C3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=C1 IDXDMHGZQWHGAV-UHFFFAOYSA-N 0.000 claims 2
- WSHYFIVKQNBLOX-UHFFFAOYSA-N 2-imidazol-1-ylethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCN3C=NC=C3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=N1 WSHYFIVKQNBLOX-UHFFFAOYSA-N 0.000 claims 2
- VLGACCFXZWUYSY-UHFFFAOYSA-N 2-pyridin-3-ylethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCC=3C=NC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=N1 VLGACCFXZWUYSY-UHFFFAOYSA-N 0.000 claims 2
- IJSBTLYHVZFAQV-UHFFFAOYSA-N 2-pyridin-4-ylethyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound S1C=2CN(C(=O)OCCC=3C=CN=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=N1 IJSBTLYHVZFAQV-UHFFFAOYSA-N 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- SGWAXFPWEVQIER-UHFFFAOYSA-N 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylic acid Chemical compound S1C=2CN(C(O)=O)CCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC=N1 SGWAXFPWEVQIER-UHFFFAOYSA-N 0.000 claims 2
- MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 229940124613 TLR 7/8 agonist Drugs 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims 2
- 230000000973 chemotherapeutic effect Effects 0.000 claims 2
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims 2
- NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229960001433 erlotinib Drugs 0.000 claims 2
- AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 claims 2
- 229960002584 gefitinib Drugs 0.000 claims 2
- XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 claims 2
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims 2
- 230000009826 neoplastic cell growth Effects 0.000 claims 2
- 229960000435 oblimersen Drugs 0.000 claims 2
- MIMNFCVQODTQDP-NDLVEFNKSA-N oblimersen Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(S)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C3=NC=NC(N)=C3N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=NC=NC(N)=C3N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)CO)[C@@H](O)C1 MIMNFCVQODTQDP-NDLVEFNKSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 229930002330 retinoic acid Natural products 0.000 claims 2
- OHRURASPPZQGQM-GCCNXGTGSA-N romidepsin Chemical compound O1C(=O)[C@H](C(C)C)NC(=O)C(=C/C)/NC(=O)[C@H]2CSSCC\C=C\[C@@H]1CC(=O)N[C@H](C(C)C)C(=O)N2 OHRURASPPZQGQM-GCCNXGTGSA-N 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 229960003787 sorafenib Drugs 0.000 claims 2
- WINHZLLDWRZWRT-ATVHPVEESA-N sunitinib Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C WINHZLLDWRZWRT-ATVHPVEESA-N 0.000 claims 2
- AYUNIORJHRXIBJ-TXHRRWQRSA-N tanespimycin Chemical compound N1C(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC2=C(NCC=C)C(=O)C=C1C2=O AYUNIORJHRXIBJ-TXHRRWQRSA-N 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- 229940044655 toll-like receptor 9 agonist Drugs 0.000 claims 2
- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 claims 2
- 229960000604 valproic acid Drugs 0.000 claims 2
- 239000004066 vascular targeting agent Substances 0.000 claims 2
- BGSQSPCZKPLNDK-UHFFFAOYSA-N (1-methylimidazol-2-yl)methyl 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CN1C=CN=C1COC(=O)N1CC(SC(NC(=O)CCC=2C=CC=CC=2)=C2C#N)=C2CC1 BGSQSPCZKPLNDK-UHFFFAOYSA-N 0.000 claims 1
- LMVJCUHXYQLVMK-UHFFFAOYSA-N (1-methylimidazol-2-yl)methyl 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=NC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1=NC=CN1C LMVJCUHXYQLVMK-UHFFFAOYSA-N 0.000 claims 1
- FHGNBCOZVYLRND-UHFFFAOYSA-N (1-methylimidazol-2-yl)methyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound CN1C=CN=C1COC(=O)N1CC(SC(NC(=O)CCC=2N=CC=CC=2)=C2C#N)=C2CC1 FHGNBCOZVYLRND-UHFFFAOYSA-N 0.000 claims 1
- DLQIBKDKZHNKGR-UHFFFAOYSA-N (1-methylimidazol-2-yl)methyl 3-cyano-2-(3-pyridin-3-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CN=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1=NC=CN1C DLQIBKDKZHNKGR-UHFFFAOYSA-N 0.000 claims 1
- QISBTHYATJRJTR-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1COC(C)(C)O1 QISBTHYATJRJTR-UHFFFAOYSA-N 0.000 claims 1
- ZUGDTMRHFVDJEN-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-(3-pyridin-2-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CC=NC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1COC(C)(C)O1 ZUGDTMRHFVDJEN-UHFFFAOYSA-N 0.000 claims 1
- YVPMOHUBFAAEPH-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-(3-pyridin-2-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound O1C(C)(C)OCC1COC(=O)N1CC(SC(NC(=O)CCC=2N=CC=CC=2)=C2C#N)=C2CC1 YVPMOHUBFAAEPH-UHFFFAOYSA-N 0.000 claims 1
- XSYPHRKLEHRGCA-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-(3-pyridin-3-ylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C=1C=CN=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)OCC1COC(C)(C)O1 XSYPHRKLEHRGCA-UHFFFAOYSA-N 0.000 claims 1
- RLUUHGOPGDBVAS-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-cyano-2-(3-pyridin-3-ylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound O1C(C)(C)OCC1COC(=O)N1CC(SC(NC(=O)CCC=2C=NC=CC=2)=C2C#N)=C2CC1 RLUUHGOPGDBVAS-UHFFFAOYSA-N 0.000 claims 1
- SSSMCUBUVRFCNO-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-cyano-2-(3-phenylbutanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC(=O)OC)CCC(C=2C#N)=C1SC=2NC(=O)CC(C)C1=CC=CC=C1 SSSMCUBUVRFCNO-UHFFFAOYSA-N 0.000 claims 1
- IIXWTFCZHKOFOG-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridine-6-carboxylate Chemical compound C1N(C(=O)OCC(=O)OC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1 IIXWTFCZHKOFOG-UHFFFAOYSA-N 0.000 claims 1
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| WO2008066854A2 (en) * | 2006-11-28 | 2008-06-05 | Novartis Ag | Methods and compositions for inducing apoptosis in cancer cells |
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| CN111763217B (zh) * | 2019-03-30 | 2022-06-28 | 上海凌达生物医药有限公司 | 一类噻吩并氮杂环类化合物、制备方法和用途 |
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| HUP0104984A3 (en) * | 1998-03-12 | 2003-07-28 | Ontogen Corp Carlsbad | Modulators of protein tyrosine phosphatases (ptpases) pharmaceutical compositions containing them and their use |
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| GB0114185D0 (en) | 2001-06-12 | 2001-08-01 | Protherics Molecular Design Lt | Compounds |
| WO2002092076A1 (en) * | 2001-05-16 | 2002-11-21 | Cytovia, Inc. | Substituted coumarins and quinolines as caspases activators |
| US20040171603A1 (en) | 2001-05-18 | 2004-09-02 | Janos Pato | Novel therapeutic targets for the treatment of mycobacterial infections and compounds useful therefor |
| WO2003084947A1 (en) | 2002-04-09 | 2003-10-16 | Axxima Pharmaceuticals Ag | 4,5,6,7-tretrahydrobenzo[b] thiophene derivatives and methods for medical intervention against mycrobacterial infections |
| US20030232994A1 (en) | 2001-10-04 | 2003-12-18 | Shao-Po Lu | Bicyclic thiophene derivatives and combinatorial libraries thereof |
| NZ535959A (en) | 2002-03-27 | 2006-05-26 | Altana Pharma Ag | Novel alkoxypyridine-derivatives as selective inhibitors of inducible nitric oxidase synthase NOS |
| JP4103425B2 (ja) | 2002-03-28 | 2008-06-18 | セイコーエプソン株式会社 | 電気光学装置、電子機器及び投射型表示装置 |
| US7012100B1 (en) | 2002-06-04 | 2006-03-14 | Avolix Pharmaceuticals, Inc. | Cell migration inhibiting compositions and methods and compositions for treating cancer |
| DE60325985D1 (de) | 2002-09-12 | 2009-03-12 | Merck & Co Inc | Substituierte bizyklische thiophen-derivate, diese verbindungen enthaltende zusammensetzungen und anwendungsverfahren |
| CA2498399A1 (en) | 2002-09-12 | 2004-03-25 | Merck & Co., Inc. | Method of treating diabetes and related conditions |
| TW200503994A (en) | 2003-01-24 | 2005-02-01 | Novartis Ag | Organic compounds |
| IL154306A0 (en) | 2003-02-05 | 2003-09-17 | Rimonyx Pharmaceuticals Ltd | Pharmaceutical compositions comprising thieno [2,3-c] pyridine derivatives and use thereof |
| US7138529B2 (en) | 2003-04-16 | 2006-11-21 | Hoffmann-La Roche Inc. | Substituted 3-cyanothiophene acetamides as glucagon receptor antagonists |
| EP1670804A2 (en) | 2003-09-10 | 2006-06-21 | GPC Biotech AG | Heterobicyclic compounds as pharmaceutically active agents |
| EA200600607A1 (ru) | 2003-10-01 | 2006-10-27 | Алтана Фарма Аг | Производные имидазопиридина в качестве ингибиторов индуцируемой no-синтазы |
| US20050085531A1 (en) * | 2003-10-03 | 2005-04-21 | Hodge Carl N. | Thiophene-based compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions, and uses thereof |
| GB0324653D0 (en) | 2003-10-22 | 2003-11-26 | Syngenta Participations Ag | Fungicides |
| US20050250794A1 (en) | 2003-12-19 | 2005-11-10 | Andrew Napper | Methods of treating a disorder |
| US7745630B2 (en) | 2003-12-22 | 2010-06-29 | Justin Stephen Bryans | Triazolyl piperidine arginine vasopressin receptor modulators |
| ES2309765T3 (es) | 2004-05-28 | 2008-12-16 | 4Sc Ag | Tetrahidropiridotiofenos. |
| WO2005118592A1 (en) | 2004-06-04 | 2005-12-15 | Altana Pharma Ag | Tetrahydropyridothiophenes for use in the treatment of cancer |
| US7714134B2 (en) | 2004-06-11 | 2010-05-11 | 4Sc Ag | Compounds and use of tetrahydropyridothiophenes |
| SE0401970D0 (sv) | 2004-08-02 | 2004-08-02 | Astrazeneca Ab | Novel compounds |
| EP1851229A1 (en) | 2005-02-09 | 2007-11-07 | Nycomed GmbH | Tetrahydropyridothiophenes for the treatment of proliferative diseases such as cancer |
| AU2006212179A1 (en) | 2005-02-11 | 2006-08-17 | 4Sc Ag | Tetrahydropyridothiophenes as antripoliferative agents for the treatment of cancer |
| US7714136B2 (en) | 2005-05-25 | 2010-05-11 | 4Sc Ag | Tetrahydropyridothiophenes |
| US7763728B2 (en) | 2005-05-25 | 2010-07-27 | 4Sc Ag | Tetrahydropyridothiophenes |
| WO2008020045A1 (en) | 2006-08-16 | 2008-02-21 | 4Sc Ag | Tetrahydrobenzothiophene derivatives |
-
2006
- 2006-02-08 EP EP06708126A patent/EP1851229A1/en not_active Withdrawn
- 2006-02-08 CA CA002596202A patent/CA2596202A1/en not_active Abandoned
- 2006-02-08 JP JP2007553625A patent/JP2008529989A/ja active Pending
- 2006-02-08 WO PCT/EP2006/050782 patent/WO2006084869A1/en not_active Ceased
- 2006-02-08 AU AU2006212224A patent/AU2006212224A1/en not_active Abandoned
- 2006-02-08 US US11/883,596 patent/US7714135B2/en not_active Expired - Fee Related
-
2009
- 2009-03-26 US US12/411,486 patent/US20090227577A1/en not_active Abandoned
- 2009-07-28 US US12/510,362 patent/US20100324038A1/en not_active Abandoned
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