JP2016512515A5 - - Google Patents
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- Publication number
- JP2016512515A5 JP2016512515A5 JP2016501072A JP2016501072A JP2016512515A5 JP 2016512515 A5 JP2016512515 A5 JP 2016512515A5 JP 2016501072 A JP2016501072 A JP 2016501072A JP 2016501072 A JP2016501072 A JP 2016501072A JP 2016512515 A5 JP2016512515 A5 JP 2016512515A5
- Authority
- JP
- Japan
- Prior art keywords
- triazol
- tautomer
- acryloylpyrrolidin
- compound
- oxy
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 36
- 150000003839 salts Chemical class 0.000 claims 26
- 125000005843 halogen group Chemical group 0.000 claims 21
- 125000001424 substituent group Chemical group 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 4
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 238000003419 tautomerization reaction Methods 0.000 claims 3
- HIMUHMBGRATXMK-LBPRGKRZSA-N 5-[1-[(3s)-1-prop-2-enoylpyrrolidin-3-yl]oxyisoquinolin-3-yl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound C1N(C(=O)C=C)CC[C@@H]1OC1=NC(C=2NC(=O)NN=2)=CC2=CC=CC=C12 HIMUHMBGRATXMK-LBPRGKRZSA-N 0.000 claims 2
- QINYPBHHGRXHJN-IAQYHMDHSA-N 5-[1-[(3s,4r)-4-methyl-1-prop-2-enoylpyrrolidin-3-yl]oxyisoquinolin-3-yl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound C[C@@H]1CN(C(=O)C=C)C[C@H]1OC1=NC(C=2NC(=O)NN=2)=CC2=CC=CC=C12 QINYPBHHGRXHJN-IAQYHMDHSA-N 0.000 claims 2
- XFGPZKICEZNJQR-WHUIICBVSA-N 5-[1-[[(3S)-1-prop-2-enoylpyrrolidin-3-yl]amino]isoquinolin-3-yl]-1,2,4-triazolidin-3-one Chemical compound C=CC(=O)N1CC[C@@H](C1)Nc1nc(cc2ccccc12)C1NNC(=O)N1 XFGPZKICEZNJQR-WHUIICBVSA-N 0.000 claims 2
- OUXQVZPHPUFGSB-LBPRGKRZSA-N 5-[7-chloro-1-[(3s)-1-prop-2-enoylpyrrolidin-3-yl]oxyisoquinolin-3-yl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound C12=CC(Cl)=CC=C2C=C(C=2NC(=O)NN=2)N=C1O[C@H]1CCN(C(=O)C=C)C1 OUXQVZPHPUFGSB-LBPRGKRZSA-N 0.000 claims 2
- FNCLMGJYUVZZML-LBPRGKRZSA-N 5-[7-chloro-1-[[(3s)-1-prop-2-enoylpyrrolidin-3-yl]amino]isoquinolin-3-yl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound C12=CC(Cl)=CC=C2C=C(C=2NC(=O)NN=2)N=C1N[C@H]1CCN(C(=O)C=C)C1 FNCLMGJYUVZZML-LBPRGKRZSA-N 0.000 claims 2
- USQOMEVAHLSQJM-VPHXOMNUSA-N 5-[8-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]oxy-1,7-naphthyridin-6-yl]-1,2,4-triazolidin-3-one Chemical compound C=CC(=O)N1CC[C@@H](C1)Oc1nc(cc2cccnc12)C1NNC(=O)N1 USQOMEVAHLSQJM-VPHXOMNUSA-N 0.000 claims 2
- FDHUJLGPJOKPPZ-VPHXOMNUSA-N 5-[8-[[(3S)-1-prop-2-enoylpyrrolidin-3-yl]amino]-1,7-naphthyridin-6-yl]-1,2,4-triazolidin-3-one Chemical compound C=CC(=O)N1CC[C@@H](C1)Nc1nc(cc2cccnc12)C1NNC(=O)N1 FDHUJLGPJOKPPZ-VPHXOMNUSA-N 0.000 claims 2
- KLOPMWUFPGQSEQ-NSHDSACASA-N 5-[8-chloro-1-[(3s)-1-prop-2-enoylpyrrolidin-3-yl]oxyisoquinolin-3-yl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound C=12C(Cl)=CC=CC2=CC(C=2NC(=O)NN=2)=NC=1O[C@H]1CCN(C(=O)C=C)C1 KLOPMWUFPGQSEQ-NSHDSACASA-N 0.000 claims 2
- OUBGQRGWUQEITD-NSHDSACASA-N 5-[8-chloro-1-[[(3s)-1-prop-2-enoylpyrrolidin-3-yl]amino]isoquinolin-3-yl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound C=12C(Cl)=CC=CC2=CC(C=2NC(=O)NN=2)=NC=1N[C@H]1CCN(C(=O)C=C)C1 OUBGQRGWUQEITD-NSHDSACASA-N 0.000 claims 2
- WIWSEHXQQRGARM-NSHDSACASA-N 5-[8-fluoro-1-[(3s)-1-prop-2-enoylpyrrolidin-3-yl]oxyisoquinolin-3-yl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound C=12C(F)=CC=CC2=CC(C=2NC(=O)NN=2)=NC=1O[C@H]1CCN(C(=O)C=C)C1 WIWSEHXQQRGARM-NSHDSACASA-N 0.000 claims 2
- UMXKAMXGCAUISS-CHPOKUKFSA-N 5-[8-fluoro-1-[[(3S)-1-prop-2-enoylpyrrolidin-3-yl]amino]isoquinolin-3-yl]-1,2,4-triazolidin-3-one Chemical compound Fc1cccc2cc(nc(N[C@H]3CCN(C3)C(=O)C=C)c12)C1NNC(=O)N1 UMXKAMXGCAUISS-CHPOKUKFSA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- -1 selected optionally Chemical group 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- QCSCZKIYJIOFBF-JBZHPUCOSA-N 5-[1-[(3R)-1-(2-methylprop-2-enoyl)pyrrolidin-3-yl]oxyisoquinolin-3-yl]-1,2,4-triazolidin-3-one Chemical compound CC(=C)C(=O)N1CC[C@H](C1)Oc1nc(cc2ccccc12)C1NNC(=O)N1 QCSCZKIYJIOFBF-JBZHPUCOSA-N 0.000 claims 1
- ISPMRSGRUAZGRQ-ZGTOLYCTSA-N 5-[1-[(3R)-1-prop-2-enoylpyrrolidin-3-yl]oxyisoquinolin-3-yl]-1,2,4-triazolidin-3-one Chemical compound C=CC(=O)N1CC[C@H](C1)Oc1nc(cc2ccccc12)C1NNC(=O)N1 ISPMRSGRUAZGRQ-ZGTOLYCTSA-N 0.000 claims 1
- QCSCZKIYJIOFBF-KNVGNIICSA-N 5-[1-[(3S)-1-(2-methylprop-2-enoyl)pyrrolidin-3-yl]oxyisoquinolin-3-yl]-1,2,4-triazolidin-3-one Chemical compound CC(=C)C(=O)N1CC[C@@H](C1)Oc1nc(cc2ccccc12)C1NNC(=O)N1 QCSCZKIYJIOFBF-KNVGNIICSA-N 0.000 claims 1
- HOUPMJUJPOUWRQ-CWQZNGJJSA-N 5-[1-[(3S)-1-prop-2-enoylpiperidin-3-yl]oxyisoquinolin-3-yl]-1,2,4-triazolidin-3-one Chemical compound C=CC(=O)N1CCC[C@@H](C1)Oc1nc(cc2ccccc12)C1NNC(=O)N1 HOUPMJUJPOUWRQ-CWQZNGJJSA-N 0.000 claims 1
- MCDBLBRGYQTRGF-ADQTWTKMSA-N 5-[1-[(3r)-1-[(e)-but-2-enoyl]pyrrolidin-3-yl]oxyisoquinolin-3-yl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound C1N(C(=O)/C=C/C)CC[C@H]1OC1=NC(C=2NC(=O)NN=2)=CC2=CC=CC=C12 MCDBLBRGYQTRGF-ADQTWTKMSA-N 0.000 claims 1
- QINYPBHHGRXHJN-NHYWBVRUSA-N 5-[1-[(3r,4s)-4-methyl-1-prop-2-enoylpyrrolidin-3-yl]oxyisoquinolin-3-yl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound C[C@H]1CN(C(=O)C=C)C[C@@H]1OC1=NC(C=2NC(=O)NN=2)=CC2=CC=CC=C12 QINYPBHHGRXHJN-NHYWBVRUSA-N 0.000 claims 1
- UKIVMPXDGIAZID-PXTSUWAFSA-N 5-[1-[(3s)-1-[(e)-4-(dimethylamino)but-2-enoyl]pyrrolidin-3-yl]oxyisoquinolin-3-yl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound C1N(C(=O)/C=C/CN(C)C)CC[C@@H]1OC1=NC(C=2NC(=O)NN=2)=CC2=CC=CC=C12 UKIVMPXDGIAZID-PXTSUWAFSA-N 0.000 claims 1
- YFGTVWDQSBQMBM-LBPRGKRZSA-N 5-[1-[(3s)-1-acetylpyrrolidin-3-yl]oxyisoquinolin-3-yl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound C1N(C(=O)C)CC[C@@H]1OC1=NC(C=2NC(=O)NN=2)=CC2=CC=CC=C12 YFGTVWDQSBQMBM-LBPRGKRZSA-N 0.000 claims 1
- HTXPJYDZXSMZTC-LBPRGKRZSA-N 5-[1-[(3s)-1-propanoylpyrrolidin-3-yl]oxyisoquinolin-3-yl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound C1N(C(=O)CC)CC[C@@H]1OC1=NC(C=2NC(=O)NN=2)=CC2=CC=CC=C12 HTXPJYDZXSMZTC-LBPRGKRZSA-N 0.000 claims 1
- MAOVXCGPQOZNFR-FWJOYPJLSA-N 5-[1-[[(2R)-1-prop-2-enoylpyrrolidin-2-yl]methoxy]isoquinolin-3-yl]-1,2,4-triazolidin-3-one Chemical compound C=CC(=O)N1CCC[C@@H]1COc1nc(cc2ccccc12)C1NNC(=O)N1 MAOVXCGPQOZNFR-FWJOYPJLSA-N 0.000 claims 1
- MAOVXCGPQOZNFR-CWQZNGJJSA-N 5-[1-[[(2S)-1-prop-2-enoylpyrrolidin-2-yl]methoxy]isoquinolin-3-yl]-1,2,4-triazolidin-3-one Chemical compound C=CC(=O)N1CCC[C@H]1COc1nc(cc2ccccc12)C1NNC(=O)N1 MAOVXCGPQOZNFR-CWQZNGJJSA-N 0.000 claims 1
- JDEQOOCHKQRYDQ-FVRDMJKUSA-N 5-[1-[[(2S)-1-prop-2-enoylpyrrolidin-2-yl]methylamino]isoquinolin-3-yl]-1,2,4-triazolidin-3-one Chemical compound C=CC(=O)N1CCC[C@H]1CNc1nc(cc2ccccc12)C1NNC(=O)N1 JDEQOOCHKQRYDQ-FVRDMJKUSA-N 0.000 claims 1
- DZZBILFXXHCMMJ-CWQZNGJJSA-N 5-[1-[[(3S)-1-(2-methylprop-2-enoyl)pyrrolidin-3-yl]amino]isoquinolin-3-yl]-1,2,4-triazolidin-3-one Chemical compound CC(=C)C(=O)N1CC[C@@H](C1)Nc1nc(cc2ccccc12)C1NNC(=O)N1 DZZBILFXXHCMMJ-CWQZNGJJSA-N 0.000 claims 1
- ZUQGJXLGZFVQMF-FVRDMJKUSA-N 5-[1-[[(3S)-1-prop-2-enoylpyrrolidin-3-yl]oxymethyl]isoquinolin-3-yl]-1,2,4-triazolidin-3-one Chemical compound C=CC(=O)N1CC[C@@H](C1)OCc1nc(cc2ccccc12)C1NNC(=O)N1 ZUQGJXLGZFVQMF-FVRDMJKUSA-N 0.000 claims 1
- UTDUWAWPKONJGQ-NSHDSACASA-N 5-[1-[[(3s)-1-(2-chloroacetyl)pyrrolidin-3-yl]amino]isoquinolin-3-yl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound C1N(C(=O)CCl)CC[C@@H]1NC1=NC(C=2NC(=O)NN=2)=CC2=CC=CC=C12 UTDUWAWPKONJGQ-NSHDSACASA-N 0.000 claims 1
- CYMOLUOXIMMCFW-NDRDAGNVSA-N 5-[1-[[(3s)-1-[(e)-but-2-enoyl]pyrrolidin-3-yl]amino]isoquinolin-3-yl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound C1N(C(=O)/C=C/C)CC[C@@H]1NC1=NC(C=2NC(=O)NN=2)=CC2=CC=CC=C12 CYMOLUOXIMMCFW-NDRDAGNVSA-N 0.000 claims 1
- FULFXIOQHHEWEZ-CWQZNGJJSA-N 5-[1-[methyl-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]amino]isoquinolin-3-yl]-1,2,4-triazolidin-3-one Chemical compound CN([C@H]1CCN(C1)C(=O)C=C)c1nc(cc2ccccc12)C1NNC(=O)N1 FULFXIOQHHEWEZ-CWQZNGJJSA-N 0.000 claims 1
- ZLWLFHUPLISYBJ-XLLULAGJSA-N 5-[4-methyl-6-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]oxypyridin-2-yl]-1,2,4-triazolidin-3-one Chemical compound Cc1cc(O[C@H]2CCN(C2)C(=O)C=C)nc(c1)C1NNC(=O)N1 ZLWLFHUPLISYBJ-XLLULAGJSA-N 0.000 claims 1
- IWLBOOQOHPAHJE-NKUHCKNESA-N 5-[5-methyl-6-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]oxypyridin-2-yl]-1,2,4-triazolidin-3-one Chemical compound Cc1ccc(nc1O[C@H]1CCN(C1)C(=O)C=C)C1NNC(=O)N1 IWLBOOQOHPAHJE-NKUHCKNESA-N 0.000 claims 1
- NKPZVXJYRKMJIY-LLTODGECSA-N 5-[6-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]oxypyridin-2-yl]-1,2,4-triazolidin-3-one Chemical compound C=CC(=O)N1CC[C@@H](C1)Oc1cccc(n1)C1NNC(=O)N1 NKPZVXJYRKMJIY-LLTODGECSA-N 0.000 claims 1
- MTCIVWJQXPPNAS-LBPRGKRZSA-N 5-[7-fluoro-1-[(3s)-1-prop-2-enoylpyrrolidin-3-yl]oxyisoquinolin-3-yl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound C12=CC(F)=CC=C2C=C(C=2NC(=O)NN=2)N=C1O[C@H]1CCN(C(=O)C=C)C1 MTCIVWJQXPPNAS-LBPRGKRZSA-N 0.000 claims 1
- IQQZPESQANJEIH-LBPRGKRZSA-N 5-[7-fluoro-1-[[(3s)-1-prop-2-enoylpyrrolidin-3-yl]amino]isoquinolin-3-yl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound C12=CC(F)=CC=C2C=C(C=2NC(=O)NN=2)N=C1N[C@H]1CCN(C(=O)C=C)C1 IQQZPESQANJEIH-LBPRGKRZSA-N 0.000 claims 1
- FLDYREMAARAHTJ-LBPRGKRZSA-N 5-[8-methoxy-1-[[(3s)-1-prop-2-enoylpyrrolidin-3-yl]amino]isoquinolin-3-yl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound C=12C(OC)=CC=CC2=CC(C=2NC(=O)NN=2)=NC=1N[C@H]1CCN(C(=O)C=C)C1 FLDYREMAARAHTJ-LBPRGKRZSA-N 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 1
- 208000003950 B-cell lymphoma Diseases 0.000 claims 1
- 208000009137 Behcet syndrome Diseases 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 208000028622 Immune thrombocytopenia Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000005777 Lupus Nephritis Diseases 0.000 claims 1
- 208000008771 Lymphadenopathy Diseases 0.000 claims 1
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- RDAUVLJFXVQEQM-UHFFFAOYSA-N N-[1-[3-(5-oxo-1,2,4-triazolidin-3-yl)isoquinolin-1-yl]pyrrolidin-3-yl]prop-2-enamide Chemical compound C=CC(=O)NC1CCN(C1)c1nc(cc2ccccc12)C1NNC(=O)N1 RDAUVLJFXVQEQM-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 201000011152 Pemphigus Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000010216 atopic IgE responsiveness Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 208000018555 lymphatic system disease Diseases 0.000 claims 1
- 230000003211 malignant effect Effects 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 201000001976 pemphigus vulgaris Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 210000004180 plasmocyte Anatomy 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361776445P | 2013-03-11 | 2013-03-11 | |
| US61/776,445 | 2013-03-11 | ||
| PCT/US2014/022801 WO2014164558A1 (en) | 2013-03-11 | 2014-03-10 | Pyridinyl and fused pyridinyl triazolone derivatives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017252294A Division JP6462842B2 (ja) | 2013-03-11 | 2017-12-27 | ピリジニルトリアゾロン誘導体及び縮合ピリジニルトリアゾロン誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016512515A JP2016512515A (ja) | 2016-04-28 |
| JP2016512515A5 true JP2016512515A5 (enExample) | 2017-04-13 |
| JP6271700B2 JP6271700B2 (ja) | 2018-01-31 |
Family
ID=50543655
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016501072A Active JP6271700B2 (ja) | 2013-03-11 | 2014-03-10 | ピリジニルトリアゾロン誘導体及び縮合ピリジニルトリアゾロン誘導体 |
| JP2017252294A Active JP6462842B2 (ja) | 2013-03-11 | 2017-12-27 | ピリジニルトリアゾロン誘導体及び縮合ピリジニルトリアゾロン誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017252294A Active JP6462842B2 (ja) | 2013-03-11 | 2017-12-27 | ピリジニルトリアゾロン誘導体及び縮合ピリジニルトリアゾロン誘導体 |
Country Status (43)
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2013312296B2 (en) | 2012-09-10 | 2017-06-22 | Principia Biopharma Inc. | Pyrazolopyrimidine compounds as kinase inhibitors |
| JO3377B1 (ar) * | 2013-03-11 | 2019-03-13 | Takeda Pharmaceuticals Co | مشتقات بيريدينيل وبيريدينيل مندمج |
| KR20160117614A (ko) | 2014-02-21 | 2016-10-10 | 프린시피아 바이오파마, 인코퍼레이티드 | Btk 억제제의 염 및 고체 형태 |
| CN104447530A (zh) * | 2014-12-11 | 2015-03-25 | 苏州欧凯医药技术有限公司 | 4-甲基-2,6-二羧基吡啶的制备方法 |
| EA036269B1 (ru) | 2014-12-18 | 2020-10-21 | Принсипиа Биофарма Инк. | Лечение пузырчатки |
| WO2016210165A1 (en) | 2015-06-24 | 2016-12-29 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| ES2877089T3 (es) | 2015-12-24 | 2021-11-16 | Takeda Pharmaceuticals Co | Cocristal, método de producción del mismo, y medicamento que contiene dicho cocristal |
| WO2017122175A1 (en) * | 2016-01-13 | 2017-07-20 | Acerta Pharma B.V. | Therapeutic combinations of an antifolate and a btk inhibitor |
| ES2886080T3 (es) | 2016-03-31 | 2021-12-16 | Takeda Pharmaceuticals Co | Complejos de isoquinolinil triazolona |
| EP3478273A1 (en) | 2016-06-29 | 2019-05-08 | Principia Biopharma Inc. | Modified release formulations of 2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile |
| CN112424207B (zh) | 2018-07-25 | 2024-03-19 | 诺华股份有限公司 | Nlrp3炎性小体抑制剂 |
| BR112021018168B1 (pt) | 2019-03-21 | 2023-11-28 | Onxeo | Composição farmacêutica, combinação e kit compreendendo uma molécula dbait e um inibidor de quinase para o tratamento de câncer |
| KR102459858B1 (ko) * | 2019-04-02 | 2022-10-27 | 연세대학교 산학협력단 | 신규 화합물 및 이를 유효성분으로 포함하는 호흡기 질환의 예방 또는 치료용 조성물 |
| UY38687A (es) | 2019-05-17 | 2023-05-15 | Novartis Ag | Inhibidores del inflamasoma nlrp3, composiciones, combinaciones de los mismos y métodos para su uso |
| EP4045051A1 (en) | 2019-10-14 | 2022-08-24 | Principia Biopharma Inc. | Methods for treating immune thrombocytopenia by administering (r)-2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile |
| CA3159348A1 (en) | 2019-11-08 | 2021-05-14 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Methods for the treatment of cancers that have acquired resistance to kinase inhibitors |
| PH12022551787A1 (en) | 2020-01-22 | 2024-02-12 | Principia Biopharma Inc | Crystalline forms of 2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)-1h-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| EP4196478A1 (en) | 2020-08-14 | 2023-06-21 | Novartis AG | Heteroaryl substituted spiropiperidinyl derivatives and pharmaceutical uses thereof |
| UY40374A (es) | 2022-08-03 | 2024-02-15 | Novartis Ag | Inhibidores de inflamasoma nlrp3 |
| WO2025116652A1 (ko) * | 2023-11-30 | 2025-06-05 | 주식회사 지엔티파마 | 자가면역 질환 치료용 조성물 및 방법 |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| GB9518953D0 (en) | 1995-09-15 | 1995-11-15 | Pfizer Ltd | Pharmaceutical formulations |
| US5733849A (en) * | 1996-03-15 | 1998-03-31 | Rohm And Haas Company | Halopyridyl triazolinone herbicides and herbicidal use thereof |
| GB9711643D0 (en) | 1997-06-05 | 1997-07-30 | Janssen Pharmaceutica Nv | Glass thermoplastic systems |
| CA2328962A1 (en) | 1998-04-17 | 1999-10-28 | Parker Hughes Institute | Btk inhibitors and methods for their identification and use |
| DK1318997T3 (da) * | 2000-09-15 | 2006-09-25 | Vertex Pharma | Pyrazolforbindelser der er nyttige som proteinkinase-inhibitorer |
| ES2257461T3 (es) | 2000-12-21 | 2006-08-01 | Bristol-Myers Squibb Company | Inhibidores de tiazolilo de tirosina quinasas de la familia tec. |
| US7572809B2 (en) * | 2005-12-19 | 2009-08-11 | Hoffmann-La Roche Inc. | Isoquinoline aminopyrazole derivatives |
| RU2008133161A (ru) | 2006-01-13 | 2010-02-20 | Фармасайкликс, Инк. (Us) | Ингибиторы тирозин киназ и их применение |
| AU2007267859B2 (en) * | 2006-05-25 | 2012-04-12 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate Hsp90 activity |
| MX2008015843A (es) | 2006-06-20 | 2009-01-09 | Hoffmann La Roche | Derivados de tetralina e indano y usos de los mismos. |
| AR063946A1 (es) | 2006-09-11 | 2009-03-04 | Cgi Pharmaceuticals Inc | Determinadas pirimidinas sustituidas, el uso de las mismas para el tratamiento de enfermedades mediadas por la inhibicion de la actividad de btk y composiciones farmaceuticas que las comprenden. |
| EA018573B1 (ru) | 2006-09-22 | 2013-09-30 | Фармасайкликс, Инк. | Ингибиторы тирозинкиназы брутона |
| SG10201508035TA (en) | 2007-03-28 | 2015-10-29 | Pharmacyclics Inc | Inhibitors of bruton's tyrosine kinase |
| JP5643105B2 (ja) | 2007-12-14 | 2014-12-17 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 新規イミダゾ［１，２−ａ］ピリジン及びイミダゾ［１，２−ｂ］ピリダジン誘導体 |
| WO2009098144A1 (en) | 2008-02-05 | 2009-08-13 | F. Hoffmann-La Roche Ag | Novel pyridinones and pyridazinones |
| WO2009156284A1 (en) | 2008-06-24 | 2009-12-30 | F. Hoffmann-La Roche Ag | Novel substituted pyridin-2-ones and pyridazin-3-ones |
| AU2009265813B2 (en) | 2008-07-02 | 2014-04-10 | F. Hoffmann-La Roche Ag | Novel phenylpyrazinones as kinase inhibitors |
| EP2307413B1 (en) | 2008-07-15 | 2015-09-09 | F. Hoffmann-La Roche AG | Novel phenyl-imidazopyridines and pyridazines |
| US8598174B2 (en) | 2008-11-12 | 2013-12-03 | Genetech, Inc. | Pyridazinones, method of making, and method of use thereof |
| WO2010068810A2 (en) | 2008-12-10 | 2010-06-17 | Cgi Pharmaceuticals, Inc. | Certain substituted amides, method of making, and method of use thereof |
| WO2010068788A1 (en) * | 2008-12-10 | 2010-06-17 | Cgi Pharmaceuticals, Inc. | Heterocyclic amides as btk inhibitors |
| US8497265B2 (en) | 2010-05-13 | 2013-07-30 | Amgen Inc. | Heteroaryloxyheterocyclyl compounds as PDE10 inhibitors |
| WO2011153553A2 (en) | 2010-06-04 | 2011-12-08 | The Regents Of The University Of California | Methods and compositions for kinase inhibition |
| AR083267A1 (es) * | 2010-10-04 | 2013-02-13 | Novartis Ag | Combinaciones farmaceuticas |
| AU2011317855B2 (en) | 2010-10-20 | 2015-04-30 | Grunenthal Gmbh | Substituted 6-amino-nicotinamides as KCNQ2/3 modulators |
| US9308585B2 (en) | 2010-11-10 | 2016-04-12 | Stc.Unm | Aerosol reduction/expansion synthesis (A-RES) for zero valent metal particles |
| JO3377B1 (ar) | 2013-03-11 | 2019-03-13 | Takeda Pharmaceuticals Co | مشتقات بيريدينيل وبيريدينيل مندمج |
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