JP2008542242A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2008542242A5 JP2008542242A5 JP2008512845A JP2008512845A JP2008542242A5 JP 2008542242 A5 JP2008542242 A5 JP 2008542242A5 JP 2008512845 A JP2008512845 A JP 2008512845A JP 2008512845 A JP2008512845 A JP 2008512845A JP 2008542242 A5 JP2008542242 A5 JP 2008542242A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- cyano
- thieno
- tetrahydro
- phenyl
- 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
Links
- -1 2,2-difluoro-1,3-benzodioxolyl Chemical group 0.000 claims 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 20
- 229910052801 chlorine Inorganic materials 0.000 claims 20
- 239000000460 chlorine Substances 0.000 claims 20
- 125000004076 pyridyl group Chemical group 0.000 claims 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 14
- 229910052731 fluorine Inorganic materials 0.000 claims 14
- 239000011737 fluorine Substances 0.000 claims 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 13
- 125000004432 carbon atom Chemical group C* 0.000 claims 13
- 206010028980 Neoplasm Diseases 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000004122 cyclic group Chemical group 0.000 claims 6
- 125000002541 furyl group Chemical group 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000001544 thienyl group Chemical group 0.000 claims 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 239000002246 antineoplastic agent Substances 0.000 claims 5
- 230000003796 beauty Effects 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 208000017604 Hodgkin disease Diseases 0.000 claims 4
- 208000010747 Hodgkins lymphoma Diseases 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
- 201000011510 cancer Diseases 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 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 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
- 210000003734 kidney Anatomy 0.000 claims 4
- 230000009826 neoplastic cell growth Effects 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
- ZYLKMRMEIHZITI-UHFFFAOYSA-N 2-(6-acetyl-3-cyano-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl)-3-phenylpropanamide Chemical compound C1N(C(=O)C)CCC(C=2C#N)=C1SC=2C(C(N)=O)CC1=CC=CC=C1 ZYLKMRMEIHZITI-UHFFFAOYSA-N 0.000 claims 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 3
- 206010038389 Renal cancer Diseases 0.000 claims 3
- 239000000556 agonist Substances 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 201000010982 kidney cancer Diseases 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
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 2
- 208000030507 AIDS Diseases 0.000 claims 2
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 2
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 2
- 208000031261 Acute myeloid leukaemia Diseases 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
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 2
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims 2
- 206010023825 Laryngeal cancer Diseases 0.000 claims 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
- 206010025323 Lymphomas Diseases 0.000 claims 2
- 206010027406 Mesothelioma Diseases 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 2
- 201000000582 Retinoblastoma Diseases 0.000 claims 2
- 206010039491 Sarcoma Diseases 0.000 claims 2
- 206010042971 T-cell lymphoma Diseases 0.000 claims 2
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims 2
- 229940124613 TLR 7/8 agonist Drugs 0.000 claims 2
- 208000008383 Wilms tumor Diseases 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
- 210000000988 bone and bone Anatomy 0.000 claims 2
- 210000004556 brain Anatomy 0.000 claims 2
- 210000000481 breast Anatomy 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
- 210000003169 central nervous system Anatomy 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
- 230000001684 chronic effect Effects 0.000 claims 2
- 210000001072 colon Anatomy 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 210000003372 endocrine gland Anatomy 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
- 210000003238 esophagus Anatomy 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
- 210000004602 germ cell Anatomy 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 210000003128 head Anatomy 0.000 claims 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 201000006866 hypopharynx cancer Diseases 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
- 206010023841 laryngeal neoplasm Diseases 0.000 claims 2
- 208000032839 leukemia Diseases 0.000 claims 2
- 210000004185 liver Anatomy 0.000 claims 2
- 201000007270 liver cancer Diseases 0.000 claims 2
- 208000014018 liver neoplasm Diseases 0.000 claims 2
- 210000004072 lung Anatomy 0.000 claims 2
- 201000005202 lung cancer Diseases 0.000 claims 2
- 208000020816 lung neoplasm Diseases 0.000 claims 2
- 230000036210 malignancy Effects 0.000 claims 2
- 208000026037 malignant tumor of neck Diseases 0.000 claims 2
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 210000003739 neck Anatomy 0.000 claims 2
- 230000001613 neoplastic effect Effects 0.000 claims 2
- 201000008026 nephroblastoma Diseases 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
- 210000001672 ovary Anatomy 0.000 claims 2
- 210000000496 pancreas Anatomy 0.000 claims 2
- 210000001428 peripheral nervous system Anatomy 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 210000004180 plasmocyte Anatomy 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 2
- 229940080818 propionamide Drugs 0.000 claims 2
- 210000002307 prostate Anatomy 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 210000000664 rectum Anatomy 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
- 210000003491 skin Anatomy 0.000 claims 2
- 210000000813 small intestine Anatomy 0.000 claims 2
- 210000004872 soft tissue Anatomy 0.000 claims 2
- 229960003787 sorafenib Drugs 0.000 claims 2
- 210000002784 stomach Anatomy 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
- 210000001550 testis Anatomy 0.000 claims 2
- WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims 2
- 229940044655 toll-like receptor 9 agonist Drugs 0.000 claims 2
- 210000003932 urinary bladder Anatomy 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
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- ZGNLFUXWZJGETL-YUSKDDKASA-N (Z)-[(2S)-2-amino-2-carboxyethyl]-hydroxyimino-oxidoazanium Chemical compound N[C@@H](C\[N+]([O-])=N\O)C(O)=O ZGNLFUXWZJGETL-YUSKDDKASA-N 0.000 claims 1
- BWDQBBCUWLSASG-MDZDMXLPSA-N (e)-n-hydroxy-3-[4-[[2-hydroxyethyl-[2-(1h-indol-3-yl)ethyl]amino]methyl]phenyl]prop-2-enamide Chemical compound C=1NC2=CC=CC=C2C=1CCN(CCO)CC1=CC=C(\C=C\C(=O)NO)C=C1 BWDQBBCUWLSASG-MDZDMXLPSA-N 0.000 claims 1
- NVKGVBZZSJFQLM-UHFFFAOYSA-N 1-(2-chloroethyl)-1-nitrosourea Chemical compound NC(=O)N(N=O)CCCl NVKGVBZZSJFQLM-UHFFFAOYSA-N 0.000 claims 1
- CKTSBUTUHBMZGZ-SHYZEUOFSA-N 2'‐deoxycytidine Chemical class O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 CKTSBUTUHBMZGZ-SHYZEUOFSA-N 0.000 claims 1
- ZFKYCRVGESMZKS-UHFFFAOYSA-N 2-amino-6-(2-pyridin-4-ylacetyl)-5,7-dihydro-4H-thieno[2,3-c]pyridine-3-carbonitrile Chemical compound C1CC=2C(C#N)=C(N)SC=2CN1C(=O)CC1=CC=NC=C1 ZFKYCRVGESMZKS-UHFFFAOYSA-N 0.000 claims 1
- RVSRKPSRXHQSNI-UHFFFAOYSA-N 2-amino-6-(3-imidazol-1-ylpropanoyl)-5,7-dihydro-4H-thieno[2,3-c]pyridine-3-carbonitrile Chemical compound C1CC=2C(C#N)=C(N)SC=2CN1C(=O)CCN1C=CN=C1 RVSRKPSRXHQSNI-UHFFFAOYSA-N 0.000 claims 1
- ZZVMTTYYCJKWEP-UHFFFAOYSA-N 2-amino-6-(3-pyridin-3-ylpropanoyl)-5,7-dihydro-4H-thieno[2,3-c]pyridine-3-carbonitrile Chemical compound C1CC=2C(C#N)=C(N)SC=2CN1C(=O)CCC1=CC=CN=C1 ZZVMTTYYCJKWEP-UHFFFAOYSA-N 0.000 claims 1
- AHDDRJBFJBDEPW-UHFFFAOYSA-N 2-phenylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1C1=CC=CC=C1 AHDDRJBFJBDEPW-UHFFFAOYSA-N 0.000 claims 1
- NMUSYJAQQFHJEW-UHFFFAOYSA-N 5-Azacytidine Natural products O=C1N=C(N)N=CN1C1C(O)C(O)C(CO)O1 NMUSYJAQQFHJEW-UHFFFAOYSA-N 0.000 claims 1
- TZYVRXZQAWPIAB-FCLHUMLKSA-N 5-amino-3-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4h-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dione Chemical compound O=C1SC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O TZYVRXZQAWPIAB-FCLHUMLKSA-N 0.000 claims 1
- XAUDJQYHKZQPEU-KVQBGUIXSA-N 5-aza-2'-deoxycytidine Chemical compound O=C1N=C(N)N=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 XAUDJQYHKZQPEU-KVQBGUIXSA-N 0.000 claims 1
- NMUSYJAQQFHJEW-KVTDHHQDSA-N 5-azacytidine Chemical compound O=C1N=C(N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NMUSYJAQQFHJEW-KVTDHHQDSA-N 0.000 claims 1
- 206010061424 Anal cancer Diseases 0.000 claims 1
- 208000007860 Anus Neoplasms Diseases 0.000 claims 1
- 108010006654 Bleomycin Proteins 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 1
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims 1
- GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 claims 1
- GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 claims 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims 1
- 102000004127 Cytokines Human genes 0.000 claims 1
- 108090000695 Cytokines Proteins 0.000 claims 1
- 102000009058 Death Domain Receptors Human genes 0.000 claims 1
- 108010049207 Death Domain Receptors Proteins 0.000 claims 1
- 108010002156 Depsipeptides Proteins 0.000 claims 1
- 102000015212 Fas Ligand Protein Human genes 0.000 claims 1
- 108010039471 Fas Ligand Protein Proteins 0.000 claims 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 1
- 206010021042 Hypopharyngeal cancer Diseases 0.000 claims 1
- 206010056305 Hypopharyngeal neoplasm Diseases 0.000 claims 1
- 102000008394 Immunoglobulin Fragments Human genes 0.000 claims 1
- 108010021625 Immunoglobulin Fragments Proteins 0.000 claims 1
- 108010078049 Interferon alpha-2 Proteins 0.000 claims 1
- 102100039350 Interferon alpha-7 Human genes 0.000 claims 1
- 102000008070 Interferon-gamma Human genes 0.000 claims 1
- 108010074328 Interferon-gamma Proteins 0.000 claims 1
- 108010050904 Interferons Proteins 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 claims 1
- 102000000588 Interleukin-2 Human genes 0.000 claims 1
- 108010002350 Interleukin-2 Proteins 0.000 claims 1
- MLFKVJCWGUZWNV-UHFFFAOYSA-N L-alanosine Natural products OC(=O)C(N)CN(O)N=O MLFKVJCWGUZWNV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 239000005517 L01XE01 - Imatinib Substances 0.000 claims 1
- 239000005411 L01XE02 - Gefitinib Substances 0.000 claims 1
- 239000005551 L01XE03 - Erlotinib Substances 0.000 claims 1
- 239000002147 L01XE04 - Sunitinib Substances 0.000 claims 1
- 239000005511 L01XE05 - Sorafenib Substances 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 229940121849 Mitotic inhibitor Drugs 0.000 claims 1
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims 1
- HRNLUBSXIHFDHP-UHFFFAOYSA-N N-(2-aminophenyl)-4-[[[4-(3-pyridinyl)-2-pyrimidinyl]amino]methyl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CNC1=NC=CC(C=2C=NC=CC=2)=N1 HRNLUBSXIHFDHP-UHFFFAOYSA-N 0.000 claims 1
- 108091034117 Oligonucleotide Proteins 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 229940079156 Proteasome inhibitor Drugs 0.000 claims 1
- 208000015634 Rectal Neoplasms Diseases 0.000 claims 1
- 208000000453 Skin Neoplasms Diseases 0.000 claims 1
- 208000032383 Soft tissue cancer Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 229940123237 Taxane Drugs 0.000 claims 1
- 208000024313 Testicular Neoplasms Diseases 0.000 claims 1
- 206010057644 Testis cancer Diseases 0.000 claims 1
- FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 claims 1
- 102000002689 Toll-like receptor Human genes 0.000 claims 1
- 108020000411 Toll-like receptor Proteins 0.000 claims 1
- 208000023915 Ureteral Neoplasms Diseases 0.000 claims 1
- 206010046392 Ureteric cancer Diseases 0.000 claims 1
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims 1
- 102000016549 Vascular Endothelial Growth Factor Receptor-2 Human genes 0.000 claims 1
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 claims 1
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 claims 1
- 229940122803 Vinca alkaloid Drugs 0.000 claims 1
- DYGKALZZBMZIGH-UHFFFAOYSA-N [2-[3-cyano-2-(3-phenylpropanoylamino)-5,7-dihydro-4h-thieno[2,3-c]pyridin-6-yl]-2-oxoethyl] acetate Chemical compound C1N(C(=O)COC(=O)C)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1 DYGKALZZBMZIGH-UHFFFAOYSA-N 0.000 claims 1
- 229950005033 alanosine Drugs 0.000 claims 1
- 229940060265 aldara Drugs 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 229940045799 anthracyclines and related substance Drugs 0.000 claims 1
- 230000002280 anti-androgenic effect Effects 0.000 claims 1
- 230000001772 anti-angiogenic effect Effects 0.000 claims 1
- 229940046836 anti-estrogen Drugs 0.000 claims 1
- 230000001833 anti-estrogenic effect Effects 0.000 claims 1
- 239000000051 antiandrogen Substances 0.000 claims 1
- 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 claims 1
- 201000011165 anus cancer Diseases 0.000 claims 1
- 230000006907 apoptotic process Effects 0.000 claims 1
- 239000003886 aromatase inhibitor Substances 0.000 claims 1
- 229940046844 aromatase inhibitors Drugs 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 229960002756 azacitidine Drugs 0.000 claims 1
- 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 1
- 229960003094 belinostat Drugs 0.000 claims 1
- NCNRHFGMJRPRSK-MDZDMXLPSA-N belinostat Chemical compound ONC(=O)\C=C\C1=CC=CC(S(=O)(=O)NC=2C=CC=CC=2)=C1 NCNRHFGMJRPRSK-MDZDMXLPSA-N 0.000 claims 1
- 125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 claims 1
- 229960000397 bevacizumab Drugs 0.000 claims 1
- 229960001561 bleomycin Drugs 0.000 claims 1
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 claims 1
- 229940127093 camptothecin Drugs 0.000 claims 1
- 229960004117 capecitabine Drugs 0.000 claims 1
- 229960004562 carboplatin Drugs 0.000 claims 1
- 229960005395 cetuximab Drugs 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 1
- 229960004316 cisplatin Drugs 0.000 claims 1
- WDOGQTQEKVLZIJ-WAYWQWQTSA-N combretastatin a-4 phosphate Chemical compound C1=C(OP(O)(O)=O)C(OC)=CC=C1\C=C/C1=CC(OC)=C(OC)C(OC)=C1 WDOGQTQEKVLZIJ-WAYWQWQTSA-N 0.000 claims 1
- 229960004397 cyclophosphamide Drugs 0.000 claims 1
- 229960000684 cytarabine Drugs 0.000 claims 1
- 229960003603 decitabine Drugs 0.000 claims 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims 1
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 claims 1
- 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 1
- 239000003534 dna topoisomerase inhibitor Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 210000004696 endometrium Anatomy 0.000 claims 1
- INVTYAOGFAGBOE-UHFFFAOYSA-N entinostat Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CNC(=O)OCC1=CC=CN=C1 INVTYAOGFAGBOE-UHFFFAOYSA-N 0.000 claims 1
- YJGVMLPVUAXIQN-UHFFFAOYSA-N epipodophyllotoxin Natural products COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YJGVMLPVUAXIQN-UHFFFAOYSA-N 0.000 claims 1
- 229930013356 epothilone Natural products 0.000 claims 1
- HESCAJZNRMSMJG-KKQRBIROSA-N epothilone A Chemical class C/C([C@@H]1C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(C)=N1 HESCAJZNRMSMJG-KKQRBIROSA-N 0.000 claims 1
- 239000000328 estrogen antagonist Substances 0.000 claims 1
- 229960000390 fludarabine Drugs 0.000 claims 1
- GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229960002949 fluorouracil Drugs 0.000 claims 1
- 239000004052 folic acid antagonist Substances 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 229960005277 gemcitabine Drugs 0.000 claims 1
- 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 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 1
- 239000003481 heat shock protein 90 inhibitor Substances 0.000 claims 1
- 229940121372 histone deacetylase inhibitor Drugs 0.000 claims 1
- 239000003276 histone deacetylase inhibitor Substances 0.000 claims 1
- 230000003054 hormonal effect Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims 1
- 229960001101 ifosfamide Drugs 0.000 claims 1
- 229960002411 imatinib Drugs 0.000 claims 1
- 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 1
- 229960002751 imiquimod Drugs 0.000 claims 1
- 230000003308 immunostimulating effect Effects 0.000 claims 1
- 230000006698 induction Effects 0.000 claims 1
- 230000006882 induction of apoptosis Effects 0.000 claims 1
- 229960003130 interferon gamma Drugs 0.000 claims 1
- 229940047124 interferons Drugs 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 229950003954 isatoribine Drugs 0.000 claims 1
- 229940043355 kinase inhibitor Drugs 0.000 claims 1
- 210000000867 larynx Anatomy 0.000 claims 1
- 201000004962 larynx cancer Diseases 0.000 claims 1
- 230000003211 malignant effect Effects 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 claims 1
- 229960001924 melphalan Drugs 0.000 claims 1
- 229960001428 mercaptopurine Drugs 0.000 claims 1
- 229960000485 methotrexate Drugs 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 239000003697 methyltransferase inhibitor Substances 0.000 claims 1
- 230000000394 mitotic effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- MGGUTZGJDZLFMA-UHFFFAOYSA-N n-(6-butanoyl-3-cyano-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl)-3-(furan-2-yl)propanamide Chemical compound C1N(C(=O)CCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CO1 MGGUTZGJDZLFMA-UHFFFAOYSA-N 0.000 claims 1
- KSXQQRANKSRZPL-UHFFFAOYSA-N n-(6-butanoyl-3-cyano-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl)-3-phenylbutanamide Chemical compound C1N(C(=O)CCC)CCC(C=2C#N)=C1SC=2NC(=O)CC(C)C1=CC=CC=C1 KSXQQRANKSRZPL-UHFFFAOYSA-N 0.000 claims 1
- POTFHQIEFBHKPE-UHFFFAOYSA-N n-(6-butanoyl-3-cyano-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl)-3-phenylpropanamide Chemical compound C1N(C(=O)CCC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1 POTFHQIEFBHKPE-UHFFFAOYSA-N 0.000 claims 1
- XFLCEDQNMYYLIN-UHFFFAOYSA-N n-[3-cyano-6-(2-hydroxyacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-(furan-2-yl)propanamide Chemical compound C1N(C(=O)CO)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CO1 XFLCEDQNMYYLIN-UHFFFAOYSA-N 0.000 claims 1
- FAUQTKUFFLVGRH-UHFFFAOYSA-N n-[3-cyano-6-(2-hydroxyacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-cyclohexylpropanamide Chemical compound C1N(C(=O)CO)CCC(C=2C#N)=C1SC=2NC(=O)CCC1CCCCC1 FAUQTKUFFLVGRH-UHFFFAOYSA-N 0.000 claims 1
- KJPKDRMKZGWMRX-UHFFFAOYSA-N n-[3-cyano-6-(2-hydroxyacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylbutanamide Chemical compound S1C=2CN(C(=O)CO)CCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC=C1 KJPKDRMKZGWMRX-UHFFFAOYSA-N 0.000 claims 1
- CWHMUSRBIGRSSU-UHFFFAOYSA-N n-[3-cyano-6-(2-hydroxyacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylpropanamide Chemical compound C1N(C(=O)CO)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1 CWHMUSRBIGRSSU-UHFFFAOYSA-N 0.000 claims 1
- LEEIFYGOQQMDEH-UHFFFAOYSA-N n-[3-cyano-6-(2-hydroxyacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-pyridin-2-ylpropanamide Chemical compound C1N(C(=O)CO)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=N1 LEEIFYGOQQMDEH-UHFFFAOYSA-N 0.000 claims 1
- FSFPVZSDGOXOCT-UHFFFAOYSA-N n-[3-cyano-6-(2-hydroxyacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-pyridin-3-ylpropanamide Chemical compound C1N(C(=O)CO)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CN=C1 FSFPVZSDGOXOCT-UHFFFAOYSA-N 0.000 claims 1
- HVDJCWQZUMVCNN-UHFFFAOYSA-N n-[3-cyano-6-(2-imidazol-1-ylacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-(furan-2-yl)propanamide Chemical compound S1C=2CN(C(=O)CN3C=NC=C3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CO1 HVDJCWQZUMVCNN-UHFFFAOYSA-N 0.000 claims 1
- SXLVPBKWOFGQBF-UHFFFAOYSA-N n-[3-cyano-6-(2-imidazol-1-ylacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-cyclohexylpropanamide Chemical compound S1C=2CN(C(=O)CN3C=NC=C3)CCC=2C(C#N)=C1NC(=O)CCC1CCCCC1 SXLVPBKWOFGQBF-UHFFFAOYSA-N 0.000 claims 1
- NDKACLHVZDYZRM-UHFFFAOYSA-N n-[3-cyano-6-(2-imidazol-1-ylacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylbutanamide Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)CN1C=CN=C1 NDKACLHVZDYZRM-UHFFFAOYSA-N 0.000 claims 1
- JMWDBMPDXBDGGQ-UHFFFAOYSA-N n-[3-cyano-6-(2-imidazol-1-ylacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylpropanamide Chemical compound S1C=2CN(C(=O)CN3C=NC=C3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=C1 JMWDBMPDXBDGGQ-UHFFFAOYSA-N 0.000 claims 1
- GNNNQRVSPUSECJ-UHFFFAOYSA-N n-[3-cyano-6-(2-methoxyacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-(furan-2-yl)propanamide Chemical compound C1N(C(=O)COC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CO1 GNNNQRVSPUSECJ-UHFFFAOYSA-N 0.000 claims 1
- LUQJTXYIPYYSNL-UHFFFAOYSA-N n-[3-cyano-6-(2-methoxyacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylpropanamide Chemical compound C1N(C(=O)COC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1 LUQJTXYIPYYSNL-UHFFFAOYSA-N 0.000 claims 1
- QFLJVEOWTJLVBF-UHFFFAOYSA-N n-[3-cyano-6-(2-pyridin-2-ylacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-(furan-2-yl)propanamide Chemical compound S1C=2CN(C(=O)CC=3N=CC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CO1 QFLJVEOWTJLVBF-UHFFFAOYSA-N 0.000 claims 1
- CEVJEJBQTXYDOM-UHFFFAOYSA-N n-[3-cyano-6-(2-pyridin-2-ylacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-cyclohexylpropanamide Chemical compound S1C=2CN(C(=O)CC=3N=CC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1CCCCC1 CEVJEJBQTXYDOM-UHFFFAOYSA-N 0.000 claims 1
- XRAUUGFQFBALJV-UHFFFAOYSA-N n-[3-cyano-6-(2-pyridin-2-ylacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylbutanamide Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)CC1=CC=CC=N1 XRAUUGFQFBALJV-UHFFFAOYSA-N 0.000 claims 1
- HTVYUQKTMWFMDV-UHFFFAOYSA-N n-[3-cyano-6-(2-pyridin-3-ylacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-(furan-2-yl)propanamide Chemical compound S1C=2CN(C(=O)CC=3C=NC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CO1 HTVYUQKTMWFMDV-UHFFFAOYSA-N 0.000 claims 1
- RDKLYCOFBPRQQH-UHFFFAOYSA-N n-[3-cyano-6-(2-pyridin-3-ylacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-cyclohexylpropanamide Chemical compound S1C=2CN(C(=O)CC=3C=NC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1CCCCC1 RDKLYCOFBPRQQH-UHFFFAOYSA-N 0.000 claims 1
- LXHXMTKTMVBJIS-UHFFFAOYSA-N n-[3-cyano-6-(2-pyridin-3-ylacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylbutanamide Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)CC1=CC=CN=C1 LXHXMTKTMVBJIS-UHFFFAOYSA-N 0.000 claims 1
- YKOGEHLBCMZVLU-UHFFFAOYSA-N n-[3-cyano-6-(2-pyridin-4-ylacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-2-phenylcyclopropane-1-carboxamide Chemical compound C1CC(C(=C(NC(=O)C2C(C2)C=2C=CC=CC=2)S2)C#N)=C2CN1C(=O)CC1=CC=NC=C1 YKOGEHLBCMZVLU-UHFFFAOYSA-N 0.000 claims 1
- FTOXQBDKYHOWMR-UHFFFAOYSA-N n-[3-cyano-6-(2-pyridin-4-ylacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-(furan-2-yl)propanamide Chemical compound S1C=2CN(C(=O)CC=3C=CN=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CO1 FTOXQBDKYHOWMR-UHFFFAOYSA-N 0.000 claims 1
- ISJSEIDXELCWNV-UHFFFAOYSA-N n-[3-cyano-6-(2-pyridin-4-ylacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-cyclohexylpropanamide Chemical compound S1C=2CN(C(=O)CC=3C=CN=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1CCCCC1 ISJSEIDXELCWNV-UHFFFAOYSA-N 0.000 claims 1
- CWHRGXRLRVTVMU-UHFFFAOYSA-N n-[3-cyano-6-(2-pyridin-4-ylacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylbutanamide Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)CC1=CC=NC=C1 CWHRGXRLRVTVMU-UHFFFAOYSA-N 0.000 claims 1
- VHQFJCFYJZTKJZ-UHFFFAOYSA-N n-[3-cyano-6-(2-pyridin-4-ylacetyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylpropanamide Chemical compound S1C=2CN(C(=O)CC=3C=CN=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=C1 VHQFJCFYJZTKJZ-UHFFFAOYSA-N 0.000 claims 1
- XRDQEWKKQRGPMU-UHFFFAOYSA-N n-[3-cyano-6-(3-hydroxypropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-2-phenylcyclopropane-1-carboxamide Chemical compound C1N(C(=O)CCO)CCC(C=2C#N)=C1SC=2NC(=O)C1CC1C1=CC=CC=C1 XRDQEWKKQRGPMU-UHFFFAOYSA-N 0.000 claims 1
- PWUAWIGBQNMRMK-UHFFFAOYSA-N n-[3-cyano-6-(3-hydroxypropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-(furan-2-yl)propanamide Chemical compound C1N(C(=O)CCO)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CO1 PWUAWIGBQNMRMK-UHFFFAOYSA-N 0.000 claims 1
- YXLXUVSMBPLECJ-UHFFFAOYSA-N n-[3-cyano-6-(3-hydroxypropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-cyclohexylpropanamide Chemical compound C1N(C(=O)CCO)CCC(C=2C#N)=C1SC=2NC(=O)CCC1CCCCC1 YXLXUVSMBPLECJ-UHFFFAOYSA-N 0.000 claims 1
- VEZWRANBGONAPR-UHFFFAOYSA-N n-[3-cyano-6-(3-hydroxypropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylbutanamide Chemical compound S1C=2CN(C(=O)CCO)CCC=2C(C#N)=C1NC(=O)CC(C)C1=CC=CC=C1 VEZWRANBGONAPR-UHFFFAOYSA-N 0.000 claims 1
- ALRHDQWPSGCEKC-UHFFFAOYSA-N n-[3-cyano-6-(3-hydroxypropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylpropanamide Chemical compound C1N(C(=O)CCO)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1 ALRHDQWPSGCEKC-UHFFFAOYSA-N 0.000 claims 1
- MDOLPVCYUJERQW-UHFFFAOYSA-N n-[3-cyano-6-(3-hydroxypropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-pyridin-2-ylpropanamide Chemical compound C1N(C(=O)CCO)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=N1 MDOLPVCYUJERQW-UHFFFAOYSA-N 0.000 claims 1
- NXMQIIUYTXEZPV-UHFFFAOYSA-N n-[3-cyano-6-(3-hydroxypropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-pyridin-3-ylpropanamide Chemical compound C1N(C(=O)CCO)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CN=C1 NXMQIIUYTXEZPV-UHFFFAOYSA-N 0.000 claims 1
- YRPLFJYIEHHVTG-UHFFFAOYSA-N n-[3-cyano-6-(3-imidazol-1-ylpropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-(furan-2-yl)propanamide Chemical compound S1C=2CN(C(=O)CCN3C=NC=C3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CO1 YRPLFJYIEHHVTG-UHFFFAOYSA-N 0.000 claims 1
- DBCGEHYLLPCZDL-UHFFFAOYSA-N n-[3-cyano-6-(3-imidazol-1-ylpropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-cyclohexylpropanamide Chemical compound S1C=2CN(C(=O)CCN3C=NC=C3)CCC=2C(C#N)=C1NC(=O)CCC1CCCCC1 DBCGEHYLLPCZDL-UHFFFAOYSA-N 0.000 claims 1
- CPLNAKKFDSIEIX-UHFFFAOYSA-N n-[3-cyano-6-(3-imidazol-1-ylpropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylbutanamide Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)CCN1C=CN=C1 CPLNAKKFDSIEIX-UHFFFAOYSA-N 0.000 claims 1
- VVJNSMLNUPOAKO-UHFFFAOYSA-N n-[3-cyano-6-(3-imidazol-1-ylpropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylpropanamide Chemical compound S1C=2CN(C(=O)CCN3C=NC=C3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=C1 VVJNSMLNUPOAKO-UHFFFAOYSA-N 0.000 claims 1
- KBBVQGLMLCDJEC-UHFFFAOYSA-N n-[3-cyano-6-(3-morpholin-4-ylpropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylpropanamide Chemical compound S1C=2CN(C(=O)CCN3CCOCC3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=C1 KBBVQGLMLCDJEC-UHFFFAOYSA-N 0.000 claims 1
- HWWCLRRYTPUKBI-UHFFFAOYSA-N n-[3-cyano-6-(3-pyridin-2-ylpropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-(furan-2-yl)propanamide Chemical compound S1C=2CN(C(=O)CCC=3N=CC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CO1 HWWCLRRYTPUKBI-UHFFFAOYSA-N 0.000 claims 1
- VMYVOABNZJBWAV-UHFFFAOYSA-N n-[3-cyano-6-(3-pyridin-2-ylpropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-cyclohexylpropanamide Chemical compound S1C=2CN(C(=O)CCC=3N=CC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1CCCCC1 VMYVOABNZJBWAV-UHFFFAOYSA-N 0.000 claims 1
- GXVZBAMBKWFKLU-UHFFFAOYSA-N n-[3-cyano-6-(3-pyridin-2-ylpropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylbutanamide Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)CCC1=CC=CC=N1 GXVZBAMBKWFKLU-UHFFFAOYSA-N 0.000 claims 1
- XLZOEJDLSKLHAH-UHFFFAOYSA-N n-[3-cyano-6-(3-pyridin-2-ylpropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylpropanamide Chemical compound S1C=2CN(C(=O)CCC=3N=CC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=C1 XLZOEJDLSKLHAH-UHFFFAOYSA-N 0.000 claims 1
- WVEDGEBWPLIERU-UHFFFAOYSA-N n-[3-cyano-6-(3-pyridin-3-ylpropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-(furan-2-yl)propanamide Chemical compound S1C=2CN(C(=O)CCC=3C=NC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CO1 WVEDGEBWPLIERU-UHFFFAOYSA-N 0.000 claims 1
- IVSAMTUKOSPFTC-UHFFFAOYSA-N n-[3-cyano-6-(3-pyridin-3-ylpropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-cyclohexylpropanamide Chemical compound S1C=2CN(C(=O)CCC=3C=NC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1CCCCC1 IVSAMTUKOSPFTC-UHFFFAOYSA-N 0.000 claims 1
- KKNPTXNPQAMXTQ-UHFFFAOYSA-N n-[3-cyano-6-(3-pyridin-3-ylpropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylbutanamide Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)CCC1=CC=CN=C1 KKNPTXNPQAMXTQ-UHFFFAOYSA-N 0.000 claims 1
- QXOQDYYFHSJWSV-UHFFFAOYSA-N n-[3-cyano-6-(3-pyridin-3-ylpropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylpropanamide Chemical compound S1C=2CN(C(=O)CCC=3C=NC=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=C1 QXOQDYYFHSJWSV-UHFFFAOYSA-N 0.000 claims 1
- NKGLHHZNQWIJAQ-UHFFFAOYSA-N n-[3-cyano-6-(3-pyridin-4-ylpropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-(furan-2-yl)propanamide Chemical compound S1C=2CN(C(=O)CCC=3C=CN=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CO1 NKGLHHZNQWIJAQ-UHFFFAOYSA-N 0.000 claims 1
- QNNBNUUYJLPYAQ-UHFFFAOYSA-N n-[3-cyano-6-(3-pyridin-4-ylpropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-cyclohexylpropanamide Chemical compound S1C=2CN(C(=O)CCC=3C=CN=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1CCCCC1 QNNBNUUYJLPYAQ-UHFFFAOYSA-N 0.000 claims 1
- QBARGTRXDPSJEP-UHFFFAOYSA-N n-[3-cyano-6-(3-pyridin-4-ylpropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylbutanamide Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)CCC1=CC=NC=C1 QBARGTRXDPSJEP-UHFFFAOYSA-N 0.000 claims 1
- INLWDAOBQKKDMT-UHFFFAOYSA-N n-[3-cyano-6-(3-pyridin-4-ylpropanoyl)-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylpropanamide Chemical compound S1C=2CN(C(=O)CCC=3C=CN=CC=3)CCC=2C(C#N)=C1NC(=O)CCC1=CC=CC=C1 INLWDAOBQKKDMT-UHFFFAOYSA-N 0.000 claims 1
- SJXRIUOYYDQKBU-UHFFFAOYSA-N n-[3-cyano-6-[2-(2,4-dimethylimidazol-1-yl)acetyl]-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylbutanamide Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)CN1C=C(C)N=C1C SJXRIUOYYDQKBU-UHFFFAOYSA-N 0.000 claims 1
- KDASPCTYOCDCQR-UHFFFAOYSA-N n-[3-cyano-6-[2-(2,4-dimethylimidazol-1-yl)acetyl]-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylpropanamide Chemical compound CC1=NC(C)=CN1CC(=O)N1CC(SC(NC(=O)CCC=2C=CC=CC=2)=C2C#N)=C2CC1 KDASPCTYOCDCQR-UHFFFAOYSA-N 0.000 claims 1
- VQBXXRDTKCDWQC-UHFFFAOYSA-N n-[3-cyano-6-[2-(2-methoxyethoxy)acetyl]-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-(furan-2-yl)propanamide Chemical compound C1N(C(=O)COCCOC)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CO1 VQBXXRDTKCDWQC-UHFFFAOYSA-N 0.000 claims 1
- OCSGUJIIYJOENJ-UHFFFAOYSA-N n-[3-cyano-6-[2-(2-methylimidazol-1-yl)acetyl]-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylbutanamide Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)CN1C=CN=C1C OCSGUJIIYJOENJ-UHFFFAOYSA-N 0.000 claims 1
- JILCFODLOPNJBT-UHFFFAOYSA-N n-[3-cyano-6-[2-(2-methylimidazol-1-yl)acetyl]-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylpropanamide Chemical compound CC1=NC=CN1CC(=O)N1CC(SC(NC(=O)CCC=2C=CC=CC=2)=C2C#N)=C2CC1 JILCFODLOPNJBT-UHFFFAOYSA-N 0.000 claims 1
- FPIWESVWYSWWHM-UHFFFAOYSA-N n-[3-cyano-6-[2-(4-methylimidazol-1-yl)acetyl]-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylbutanamide Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)CN1C=NC(C)=C1 FPIWESVWYSWWHM-UHFFFAOYSA-N 0.000 claims 1
- IHBHXMOLABDYGX-UHFFFAOYSA-N n-[3-cyano-6-[2-(4-methylimidazol-1-yl)acetyl]-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylpropanamide Chemical compound C1=NC(C)=CN1CC(=O)N1CC(SC(NC(=O)CCC=2C=CC=CC=2)=C2C#N)=C2CC1 IHBHXMOLABDYGX-UHFFFAOYSA-N 0.000 claims 1
- DDBGCJUWHQCZIW-UHFFFAOYSA-N n-[3-cyano-6-[3-(1-methylimidazol-2-yl)propanoyl]-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-2-phenylcyclopropane-1-carboxamide Chemical compound CN1C=CN=C1CCC(=O)N1CC(SC(NC(=O)C2C(C2)C=2C=CC=CC=2)=C2C#N)=C2CC1 DDBGCJUWHQCZIW-UHFFFAOYSA-N 0.000 claims 1
- ZQPCJWYHDOXKOH-UHFFFAOYSA-N n-[3-cyano-6-[3-(1-methylimidazol-2-yl)propanoyl]-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-(furan-2-yl)propanamide Chemical compound CN1C=CN=C1CCC(=O)N1CC(SC(NC(=O)CCC=2OC=CC=2)=C2C#N)=C2CC1 ZQPCJWYHDOXKOH-UHFFFAOYSA-N 0.000 claims 1
- NYBCXLVSZXDQST-UHFFFAOYSA-N n-[3-cyano-6-[3-(1-methylimidazol-2-yl)propanoyl]-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-cyclohexylpropanamide Chemical compound CN1C=CN=C1CCC(=O)N1CC(SC(NC(=O)CCC2CCCCC2)=C2C#N)=C2CC1 NYBCXLVSZXDQST-UHFFFAOYSA-N 0.000 claims 1
- MWEQUOMTDLATDU-UHFFFAOYSA-N n-[3-cyano-6-[3-(1-methylimidazol-2-yl)propanoyl]-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylbutanamide Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)CCC1=NC=CN1C MWEQUOMTDLATDU-UHFFFAOYSA-N 0.000 claims 1
- BXTQAFVLBZVOOJ-UHFFFAOYSA-N n-[3-cyano-6-[3-(1-methylimidazol-2-yl)propanoyl]-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylpropanamide Chemical compound CN1C=CN=C1CCC(=O)N1CC(SC(NC(=O)CCC=2C=CC=CC=2)=C2C#N)=C2CC1 BXTQAFVLBZVOOJ-UHFFFAOYSA-N 0.000 claims 1
- UEEZCUWDAPAMJO-UHFFFAOYSA-N n-[3-cyano-6-[3-(2,4-dimethylimidazol-1-yl)propanoyl]-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylbutanamide Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)CCN1C=C(C)N=C1C UEEZCUWDAPAMJO-UHFFFAOYSA-N 0.000 claims 1
- ZTLPJVAQFRCUHD-UHFFFAOYSA-N n-[3-cyano-6-[3-(2,4-dimethylimidazol-1-yl)propanoyl]-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylpropanamide Chemical compound CC1=NC(C)=CN1CCC(=O)N1CC(SC(NC(=O)CCC=2C=CC=CC=2)=C2C#N)=C2CC1 ZTLPJVAQFRCUHD-UHFFFAOYSA-N 0.000 claims 1
- ZBPNTRORTMJYLJ-UHFFFAOYSA-N n-[3-cyano-6-[3-(2-methylbenzimidazol-1-yl)propanoyl]-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylpropanamide Chemical compound CC1=NC2=CC=CC=C2N1CCC(=O)N(C1)CCC(C=2C#N)=C1SC=2NC(=O)CCC1=CC=CC=C1 ZBPNTRORTMJYLJ-UHFFFAOYSA-N 0.000 claims 1
- MQHHBJNSKLIERZ-UHFFFAOYSA-N n-[3-cyano-6-[3-(2-methylimidazol-1-yl)propanoyl]-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylbutanamide Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)CCN1C=CN=C1C MQHHBJNSKLIERZ-UHFFFAOYSA-N 0.000 claims 1
- WNRJUPQPIPAYTJ-UHFFFAOYSA-N n-[3-cyano-6-[3-(2-methylimidazol-1-yl)propanoyl]-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylpropanamide Chemical compound CC1=NC=CN1CCC(=O)N1CC(SC(NC(=O)CCC=2C=CC=CC=2)=C2C#N)=C2CC1 WNRJUPQPIPAYTJ-UHFFFAOYSA-N 0.000 claims 1
- DJRMERNMKCNQHV-UHFFFAOYSA-N n-[3-cyano-6-[3-(4-methylimidazol-1-yl)propanoyl]-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylbutanamide Chemical compound C=1C=CC=CC=1C(C)CC(=O)NC(=C(C=1CC2)C#N)SC=1CN2C(=O)CCN1C=NC(C)=C1 DJRMERNMKCNQHV-UHFFFAOYSA-N 0.000 claims 1
- ODTCACCBWDCCGH-UHFFFAOYSA-N n-[3-cyano-6-[3-(4-methylimidazol-1-yl)propanoyl]-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylpropanamide Chemical compound C1=NC(C)=CN1CCC(=O)N1CC(SC(NC(=O)CCC=2C=CC=CC=2)=C2C#N)=C2CC1 ODTCACCBWDCCGH-UHFFFAOYSA-N 0.000 claims 1
- LFNALUSNPSXUDB-UHFFFAOYSA-N n-[3-cyano-6-[3-(4-methylpiperazin-1-yl)propanoyl]-5,7-dihydro-4h-thieno[2,3-c]pyridin-2-yl]-3-phenylpropanamide Chemical compound C1CN(C)CCN1CCC(=O)N1CC(SC(NC(=O)CCC=2C=CC=CC=2)=C2C#N)=C2CC1 LFNALUSNPSXUDB-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229960001756 oxaliplatin Drugs 0.000 claims 1
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- FPOHNWQLNRZRFC-ZHACJKMWSA-N panobinostat Chemical compound CC=1NC2=CC=CC=C2C=1CCNCC1=CC=C(\C=C\C(=O)NO)C=C1 FPOHNWQLNRZRFC-ZHACJKMWSA-N 0.000 claims 1
- 229960005079 pemetrexed Drugs 0.000 claims 1
- QOFFJEBXNKRSPX-ZDUSSCGKSA-N pemetrexed Chemical compound C1=N[C]2NC(N)=NC(=O)C2=C1CCC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 QOFFJEBXNKRSPX-ZDUSSCGKSA-N 0.000 claims 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims 1
- 150000003057 platinum Chemical class 0.000 claims 1
- 229960001237 podophyllotoxin Drugs 0.000 claims 1
- YJGVMLPVUAXIQN-XVVDYKMHSA-N podophyllotoxin Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-XVVDYKMHSA-N 0.000 claims 1
- YVCVYCSAAZQOJI-UHFFFAOYSA-N podophyllotoxin Natural products COC1=C(O)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YVCVYCSAAZQOJI-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000003207 proteasome inhibitor Substances 0.000 claims 1
- 239000000649 purine antagonist Substances 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 239000003790 pyrimidine antagonist Substances 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 229940044601 receptor agonist Drugs 0.000 claims 1
- 239000000018 receptor agonist Substances 0.000 claims 1
- 206010038038 rectal cancer Diseases 0.000 claims 1
- 201000001275 rectum cancer Diseases 0.000 claims 1
- 229950010550 resiquimod Drugs 0.000 claims 1
- BXNMTOQRYBFHNZ-UHFFFAOYSA-N resiquimod Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CC(C)(C)O)C3=C(N)N=C21 BXNMTOQRYBFHNZ-UHFFFAOYSA-N 0.000 claims 1
- 229960004641 rituximab Drugs 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 201000002314 small intestine cancer Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 229960001796 sunitinib Drugs 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 201000003120 testicular cancer Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 229960001196 thiotepa Drugs 0.000 claims 1
- 229960003087 tioguanine Drugs 0.000 claims 1
- 229940044616 toll-like receptor 7 agonist Drugs 0.000 claims 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 claims 1
- 229960000575 trastuzumab Drugs 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 239000003744 tubulin modulator Substances 0.000 claims 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 claims 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 claims 1
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 claims 1
- 210000000626 ureter Anatomy 0.000 claims 1
- 210000004291 uterus Anatomy 0.000 claims 1
- 210000001215 vagina Anatomy 0.000 claims 1
- 206010046885 vaginal cancer Diseases 0.000 claims 1
- 208000013139 vaginal neoplasm Diseases 0.000 claims 1
- 239000004066 vascular targeting agent Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05104499 | 2005-05-25 | ||
| EP05112150 | 2005-12-14 | ||
| PCT/EP2006/062613 WO2006125813A2 (en) | 2005-05-25 | 2006-05-24 | Tetrahydropyridothiophenes for use in the treatment of cancer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008542242A JP2008542242A (ja) | 2008-11-27 |
| JP2008542242A5 true JP2008542242A5 (enExample) | 2009-05-14 |
Family
ID=36658837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008512845A Pending JP2008542242A (ja) | 2005-05-25 | 2006-05-24 | 新規のテトラヒドロピリドチオフェン |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7714136B2 (enExample) |
| EP (1) | EP1896484A2 (enExample) |
| JP (1) | JP2008542242A (enExample) |
| AU (1) | AU2006251167A1 (enExample) |
| CA (1) | CA2609003A1 (enExample) |
| WO (1) | WO2006125813A2 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20070037578A (ko) | 2004-05-28 | 2007-04-05 | 알타나 파마 아게 | 테트라히드로피리도티오펜 |
| JP2008501768A (ja) | 2004-06-11 | 2008-01-24 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規の化合物及びテトラヒドロピリドチオフェンの使用 |
| EP1851229A1 (en) | 2005-02-09 | 2007-11-07 | Nycomed GmbH | Tetrahydropyridothiophenes for the treatment of proliferative diseases such as cancer |
| JP2008530053A (ja) | 2005-02-11 | 2008-08-07 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | 癌の治療のための抗増殖性剤としてのテトラヒドロピリドチオフェン |
| US7763728B2 (en) | 2005-05-25 | 2010-07-27 | 4Sc Ag | Tetrahydropyridothiophenes |
| EP1896484A2 (en) | 2005-05-25 | 2008-03-12 | Nycomed GmbH | Tetrahydropyridothiophenes for use in the treatment of cancer |
| JP2009533436A (ja) * | 2006-04-11 | 2009-09-17 | メルク エンド カムパニー インコーポレーテッド | ナイアシン受容体アゴニスト、かかる化合物を含有する組成物、及び治療法 |
| AR077405A1 (es) | 2009-07-10 | 2011-08-24 | Sanofi Aventis | Derivados del indol inhibidores de hsp90, composiciones que los contienen y utilizacion de los mismos para el tratamiento del cancer |
| FR2949467B1 (fr) | 2009-09-03 | 2011-11-25 | Sanofi Aventis | Nouveaux derives de 5,6,7,8-tetrahydroindolizine inhibiteurs d'hsp90, compositions les contenant et utilisation |
| CA3100957A1 (en) | 2018-06-19 | 2019-12-26 | Novartis Ag | N-substituted tetrahydrothienopyridine derivatives and uses thereof |
Family Cites Families (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE272078C (enExample) | ||||
| SE338693B (enExample) * | 1965-02-10 | 1971-09-13 | Rotax Ltd | |
| DE1225167B (de) | 1965-04-07 | 1966-09-22 | Huels Chemische Werke Ag | Verfahren zur Herstellung aliphatischer, aromatischer oder gemischt aliphatisch-aromatischer Sulfone |
| JPS5498337A (en) * | 1978-01-06 | 1979-08-03 | Dai Ichi Seiyaku Co Ltd | Anticarcinogenic and/or antimetastatic agent |
| JPS61129126A (ja) * | 1984-11-28 | 1986-06-17 | Kureha Chem Ind Co Ltd | 抗腫瘍剤 |
| DE4039734A1 (de) | 1990-12-13 | 1992-06-17 | Basf Ag | Substituierte 2-aminothiophene enthaltende herbizide mittel |
| GB9310700D0 (en) | 1993-05-24 | 1993-07-07 | Zeneca Ltd | Novel composition |
| JP3074640B2 (ja) | 1995-12-22 | 2000-08-07 | インターナショナル・ビジネス・マシーンズ・コーポレ−ション | 液晶表示装置の駆動方法 |
| GB9614718D0 (en) | 1996-07-12 | 1996-09-04 | Bayer Ag | 3-ureido-pyridofurans and -pyridothiophenes |
| EP1014962A4 (en) * | 1997-06-26 | 2007-06-27 | Lilly Co Eli | ANTITHROMBOTIC AGENTS |
| WO1999046267A1 (en) | 1998-03-12 | 1999-09-16 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (ptpases) |
| AU5154699A (en) | 1998-09-02 | 2000-03-27 | Novo Nordisk A/S | 4,5,6,7-tetrahydro-thieno(2,3-c)pyridine derivatives |
| JP4548882B2 (ja) * | 1999-11-30 | 2010-09-22 | 興和創薬株式会社 | ４，５，６，７−テトラヒドロチエノ〔２，３−ｃ〕ピリジン化合物 |
| US6414013B1 (en) * | 2000-06-19 | 2002-07-02 | Pharmacia & Upjohn S.P.A. | Thiophene compounds, process for preparing the same, and pharmaceutical compositions containing the same background of the invention |
| GB0114185D0 (en) | 2001-06-12 | 2001-08-01 | Protherics Molecular Design Lt | Compounds |
| EP1392283A4 (en) | 2001-05-16 | 2004-10-20 | Cytovia Inc | SUBSTITUTED CUMARINE AND CHINOLINE AS CASPASE ACTIVATORS |
| US20040171603A1 (en) | 2001-05-18 | 2004-09-02 | Janos Pato | Novel therapeutic targets for the treatment of mycobacterial infections and compounds useful therefor |
| US20030232994A1 (en) * | 2001-10-04 | 2003-12-18 | Shao-Po Lu | Bicyclic thiophene derivatives and combinatorial libraries thereof |
| JP4448695B2 (ja) | 2002-03-27 | 2010-04-14 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規アルコキシピリジン−誘導体 |
| 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 |
| AU2003224054A1 (en) | 2002-04-09 | 2003-10-20 | Axxima Pharmaceuticals Ag | 4,5,6,7-tretrahydrobenzo(b) thiophene derivatives and methods for medical intervention against mycrobacterial infections |
| US7227540B2 (en) * | 2002-04-25 | 2007-06-05 | Fujifilm Corporation | Image display unit and method of manufacturing the same |
| US7012100B1 (en) | 2002-06-04 | 2006-03-14 | Avolix Pharmaceuticals, Inc. | Cell migration inhibiting compositions and methods and compositions for treating cancer |
| CA2498399A1 (en) | 2002-09-12 | 2004-03-25 | Merck & Co., Inc. | Method of treating diabetes and related conditions |
| ATE421519T1 (de) | 2002-09-12 | 2009-02-15 | Merck & Co Inc | Substituierte bizyklische thiophen-derivate, diese verbindungen enthaltende zusammensetzungen und anwendungsverfahren |
| 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 |
| ATE399168T1 (de) | 2003-10-01 | 2008-07-15 | Nycomed Gmbh | Imidazopyridin-derivate und ihre verwendung als induzierbare no-synthase inhibitoren |
| 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 |
| CA2550091A1 (en) | 2003-12-19 | 2005-07-07 | Elixir Pharmaceuticals, Inc. | Methods of treating a disorder |
| US7745630B2 (en) | 2003-12-22 | 2010-06-29 | Justin Stephen Bryans | Triazolyl piperidine arginine vasopressin receptor modulators |
| KR20070037578A (ko) | 2004-05-28 | 2007-04-05 | 알타나 파마 아게 | 테트라히드로피리도티오펜 |
| ATE397000T1 (de) * | 2004-06-04 | 2008-06-15 | Nycomed Gmbh | Tetrahydropyridothiophenen zur verwendung in der behandlung von krebs |
| JP2008501768A (ja) | 2004-06-11 | 2008-01-24 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規の化合物及びテトラヒドロピリドチオフェンの使用 |
| 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 |
| JP2008530053A (ja) | 2005-02-11 | 2008-08-07 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | 癌の治療のための抗増殖性剤としてのテトラヒドロピリドチオフェン |
| EP1896484A2 (en) | 2005-05-25 | 2008-03-12 | Nycomed GmbH | Tetrahydropyridothiophenes for use in the treatment of cancer |
| US7763728B2 (en) | 2005-05-25 | 2010-07-27 | 4Sc Ag | Tetrahydropyridothiophenes |
| WO2008020045A1 (en) | 2006-08-16 | 2008-02-21 | 4Sc Ag | Tetrahydrobenzothiophene derivatives |
-
2006
- 2006-05-24 EP EP06755301A patent/EP1896484A2/en not_active Withdrawn
- 2006-05-24 JP JP2008512845A patent/JP2008542242A/ja active Pending
- 2006-05-24 US US11/920,572 patent/US7714136B2/en not_active Expired - Fee Related
- 2006-05-24 CA CA002609003A patent/CA2609003A1/en not_active Abandoned
- 2006-05-24 AU AU2006251167A patent/AU2006251167A1/en not_active Abandoned
- 2006-05-24 WO PCT/EP2006/062613 patent/WO2006125813A2/en not_active Ceased
-
2009
- 2009-03-26 US US12/412,021 patent/US20090258873A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2364328T3 (es) | Compuesto de pirimidina y composición medicinal del mismo. | |
| KR20240021188A (ko) | 체크포인트 키나제 1(chk1) 억제제 및 그의 용도 | |
| KR101546693B1 (ko) | 치환된 퀴놀린 화합물 및 그 사용 방법 | |
| CN113214287B (zh) | Hpk1抑制剂及其使用方法 | |
| TW200426147A (en) | Quinazolines useful as modulators of ion channels | |
| CA3023161A1 (en) | Modulators of the integrated stress pathway | |
| TW201808888A (zh) | 整合應激途徑之調節劑 | |
| KR20100137551A (ko) | 벤조피란 및 벤족세핀 ｐｉ３ｋ 저해제 화합물 및 이의 사용 방법 | |
| PT2727918T (pt) | Compostos e composições como inibidores de proteína quinase | |
| WO2013189237A1 (zh) | 穿心莲内酯类似物及其治疗的应用 | |
| EP3625228A1 (en) | Pyrimidine derivatives as pge2 receptor modulators | |
| KR20040004705A (ko) | 카스파제의 활성제 및 아폽토시스의 유도제로서의 치환된3-아릴-5-아릴-[1,2,4]-옥사디아졸과 유사체 및 이의 용도 | |
| WO2014164767A1 (en) | Novel compounds and compositions for inhibition of fasn | |
| WO2023230477A1 (en) | Pyridine checkpoint kinase 1 (chk1) inhibitors and uses thereof | |
| CN114748622A (zh) | P38激酶抑制剂降低dux4和下游基因表达以用于治疗fshd | |
| RU2013144571A (ru) | Алинзамещенные хиназолины и способы их применения | |
| JP2008542242A5 (enExample) | ||
| WO2017157882A1 (en) | Serine biosynthetic pathway inhibitors | |
| EP3556761A1 (en) | Pyrrolo-aromatic heterocyclic compound, preparation method therefor, and medical use thereof | |
| WO2024118564A1 (en) | Checkpoint kinase 1 (chk1) inhibitors and uses thereof | |
| CN120917003A (zh) | 酰基磺酰胺kat6a抑制剂 | |
| JP2018514557A (ja) | Ｓｔａｔ３経路阻害薬およびキナーゼ阻害薬を用いて癌を治療するための方法 | |
| KR20240101555A (ko) | 사이클릭 설폰아미드 리보뉴클레오타이드 환원효소(rnr) 억제제 및 이의 용도 | |
| JP2014504258A5 (enExample) | ||
| JP2008529989A5 (enExample) |