CA3034994A1 - Substituted aryl-2 pyridone compounds and use thereof for treating inflammatory and fibrotic disorders - Google Patents
Substituted aryl-2 pyridone compounds and use thereof for treating inflammatory and fibrotic disorders Download PDFInfo
- Publication number
- CA3034994A1 CA3034994A1 CA3034994A CA3034994A CA3034994A1 CA 3034994 A1 CA3034994 A1 CA 3034994A1 CA 3034994 A CA3034994 A CA 3034994A CA 3034994 A CA3034994 A CA 3034994A CA 3034994 A1 CA3034994 A1 CA 3034994A1
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- CA
- Canada
- Prior art keywords
- compound
- group
- hydrogen
- yield
- synthesis
- 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.)
- Abandoned
Links
- 0 CC(C(c1c[n](C)nc1)=CN1c(cc2)ccc2OC(F)(F)F)=C*1=* Chemical compound CC(C(c1c[n](C)nc1)=CN1c(cc2)ccc2OC(F)(F)F)=C*1=* 0.000 description 9
- QXDPRKYSNCJLQC-UHFFFAOYSA-N O=C(C=CC(c1c[nH]nc1)=C1)N1c1ccccc1 Chemical compound O=C(C=CC(c1c[nH]nc1)=C1)N1c1ccccc1 QXDPRKYSNCJLQC-UHFFFAOYSA-N 0.000 description 2
- VJMUNJRNUZTVBV-NCQKPLOXSA-N CC(C(/C(/C=N)=C/NC)=CN1c(cc2)ccc2OC(F)(F)F)=CC1=O Chemical compound CC(C(/C(/C=N)=C/NC)=CN1c(cc2)ccc2OC(F)(F)F)=CC1=O VJMUNJRNUZTVBV-NCQKPLOXSA-N 0.000 description 1
- ZAJLZDXSKYJWSF-UHFFFAOYSA-N CC(Nc1cc(N(C=C(C=C2)c3c[nH]nc3)C2=O)ccc1)=O Chemical compound CC(Nc1cc(N(C=C(C=C2)c3c[nH]nc3)C2=O)ccc1)=O ZAJLZDXSKYJWSF-UHFFFAOYSA-N 0.000 description 1
- BYPNBDAFKRKJMT-UHFFFAOYSA-N CC(Nc1cccc(N(C=C(C=C2)c(cc3)ccc3OC)C2=O)c1)=O Chemical compound CC(Nc1cccc(N(C=C(C=C2)c(cc3)ccc3OC)C2=O)c1)=O BYPNBDAFKRKJMT-UHFFFAOYSA-N 0.000 description 1
- KCKWYESHHIXBJN-UHFFFAOYSA-N CC(Nc1cccc(N(C=C(C=C2)c3c(C)[nH]nc3C)C2=O)c1)=O Chemical compound CC(Nc1cccc(N(C=C(C=C2)c3c(C)[nH]nc3C)C2=O)c1)=O KCKWYESHHIXBJN-UHFFFAOYSA-N 0.000 description 1
- YGOZGSKNKAINOW-UHFFFAOYSA-N CC(Nc1cccc(N(C=C(C=C2)c3c(C)[n](C)nc3C)C2=O)c1)=O Chemical compound CC(Nc1cccc(N(C=C(C=C2)c3c(C)[n](C)nc3C)C2=O)c1)=O YGOZGSKNKAINOW-UHFFFAOYSA-N 0.000 description 1
- AROMFMQGYQSUFI-UHFFFAOYSA-N CC(Nc1cccc(N(C=C(C=C2)c3ncc[nH]3)C2=O)c1)=O Chemical compound CC(Nc1cccc(N(C=C(C=C2)c3ncc[nH]3)C2=O)c1)=O AROMFMQGYQSUFI-UHFFFAOYSA-N 0.000 description 1
- BIAXMYPXFSWQQZ-UHFFFAOYSA-N CC(Nc1cccc(N(C=C(C=C2)c3ncccn3)C2=O)c1)=O Chemical compound CC(Nc1cccc(N(C=C(C=C2)c3ncccn3)C2=O)c1)=O BIAXMYPXFSWQQZ-UHFFFAOYSA-N 0.000 description 1
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- ZCJWFMKDNMYCKK-UHFFFAOYSA-N CCOc(cc1)cc(C)c1N(C=C(c1c[n](C)nc1)C(C)=C1)C1=O Chemical compound CCOc(cc1)cc(C)c1N(C=C(c1c[n](C)nc1)C(C)=C1)C1=O ZCJWFMKDNMYCKK-UHFFFAOYSA-N 0.000 description 1
- MTYVVPWFQPHGMO-UHFFFAOYSA-N CCOc(cc1C)ccc1N(C=C(C=C1)S(N)(=O)=O)C1=O Chemical compound CCOc(cc1C)ccc1N(C=C(C=C1)S(N)(=O)=O)C1=O MTYVVPWFQPHGMO-UHFFFAOYSA-N 0.000 description 1
- LUCJRMYXZPTHMA-UHFFFAOYSA-N CCOc(cc1C)ccc1N(C=C(C=C1)c(cccc2)c2F)C1=O Chemical compound CCOc(cc1C)ccc1N(C=C(C=C1)c(cccc2)c2F)C1=O LUCJRMYXZPTHMA-UHFFFAOYSA-N 0.000 description 1
- KMMKBNHGWVWYFW-UHFFFAOYSA-N CCOc(cc1C)ccc1N(CC=C1)C=C1c1cncnc1 Chemical compound CCOc(cc1C)ccc1N(CC=C1)C=C1c1cncnc1 KMMKBNHGWVWYFW-UHFFFAOYSA-N 0.000 description 1
- BNQPHNPBPIYALN-VEOHUUKXSA-N CC[O](C)c(cc1C)ccc1N(C=C(C=C1)/C(/C=N)=C/NC)C1=O Chemical compound CC[O](C)c(cc1C)ccc1N(C=C(C=C1)/C(/C=N)=C/NC)C1=O BNQPHNPBPIYALN-VEOHUUKXSA-N 0.000 description 1
- DLIDQKDPJKZAFX-UHFFFAOYSA-N COc(cc1)ccc1C(C=C1)=CN(c(cc2)ccc2OC(F)(F)F)C1=O Chemical compound COc(cc1)ccc1C(C=C1)=CN(c(cc2)ccc2OC(F)(F)F)C1=O DLIDQKDPJKZAFX-UHFFFAOYSA-N 0.000 description 1
- RVQVWQLDZYWSPA-UHFFFAOYSA-N COc(cccc1)c1C(C=C1)=CN(c(cc2)ccc2OC(F)(F)F)C1=O Chemical compound COc(cccc1)c1C(C=C1)=CN(c(cc2)ccc2OC(F)(F)F)C1=O RVQVWQLDZYWSPA-UHFFFAOYSA-N 0.000 description 1
- LGIITMSATMOOAC-UHFFFAOYSA-N COc1cc(C(C=C2)=CN(c(cc3)ccc3OC(F)(F)F)C2=O)ccc1 Chemical compound COc1cc(C(C=C2)=CN(c(cc3)ccc3OC(F)(F)F)C2=O)ccc1 LGIITMSATMOOAC-UHFFFAOYSA-N 0.000 description 1
- NZSXYCVENLWBIY-UHFFFAOYSA-N C[n](c(C(Nc1ncc[s]1)=O)c1)c(N2c(cc3)ccc3OC(F)(F)F)c1C=CC2=O Chemical compound C[n](c(C(Nc1ncc[s]1)=O)c1)c(N2c(cc3)ccc3OC(F)(F)F)c1C=CC2=O NZSXYCVENLWBIY-UHFFFAOYSA-N 0.000 description 1
- ZQPGZVXJCHADAW-UHFFFAOYSA-N C[n]1ncc(C(C=C2)=CN(c(cc3)ccc3OC(F)(F)F)C2=O)c1 Chemical compound C[n]1ncc(C(C=C2)=CN(c(cc3)ccc3OC(F)(F)F)C2=O)c1 ZQPGZVXJCHADAW-UHFFFAOYSA-N 0.000 description 1
- NZXHSLUUYJFOKD-UHFFFAOYSA-N Cc([nH]nc1C)c1C(C=C1)=CN(c2ccccc2)C1=O Chemical compound Cc([nH]nc1C)c1C(C=C1)=CN(c2ccccc2)C1=O NZXHSLUUYJFOKD-UHFFFAOYSA-N 0.000 description 1
- GPODOGHKEDMKLO-UHFFFAOYSA-N Cc([n](C)nc1C)c1C(C=C1)=CN(c2ccccc2)C1=O Chemical compound Cc([n](C)nc1C)c1C(C=C1)=CN(c2ccccc2)C1=O GPODOGHKEDMKLO-UHFFFAOYSA-N 0.000 description 1
- USSAPSWAUWOASP-UHFFFAOYSA-N NS(c(cc1)ccc1C(C=C1)=CN(c(cc2)ccc2OC(F)(F)F)C1=O)(=O)=O Chemical compound NS(c(cc1)ccc1C(C=C1)=CN(c(cc2)ccc2OC(F)(F)F)C1=O)(=O)=O USSAPSWAUWOASP-UHFFFAOYSA-N 0.000 description 1
- JQNKAHQBKGEXAG-UHFFFAOYSA-N NS(c(cc1)ccc1N(C=C(C=C1)c(cc2)ccc2F)C1=O)(=O)=O Chemical compound NS(c(cc1)ccc1N(C=C(C=C1)c(cc2)ccc2F)C1=O)(=O)=O JQNKAHQBKGEXAG-UHFFFAOYSA-N 0.000 description 1
- WDCDDDQVPKQIAR-UHFFFAOYSA-N O=C(C=CC(c(cc1)ccc1F)=C1)N1c(cc1)ccc1OC(F)(F)F Chemical compound O=C(C=CC(c(cc1)ccc1F)=C1)N1c(cc1)ccc1OC(F)(F)F WDCDDDQVPKQIAR-UHFFFAOYSA-N 0.000 description 1
- SAKUULGBQOVBLU-UHFFFAOYSA-N O=C(C=CC(c1cc(F)ccc1)=C1)N1c(cc1)ccc1OC(F)(F)F Chemical compound O=C(C=CC(c1cc(F)ccc1)=C1)N1c(cc1)ccc1OC(F)(F)F SAKUULGBQOVBLU-UHFFFAOYSA-N 0.000 description 1
- SQZHFSVQICMBRF-UHFFFAOYSA-N O=C(C=CC(c1ncc[s]1)=C1)N1c(cc1)ccc1OC(F)(F)F Chemical compound O=C(C=CC(c1ncc[s]1)=C1)N1c(cc1)ccc1OC(F)(F)F SQZHFSVQICMBRF-UHFFFAOYSA-N 0.000 description 1
- HXUCVVBZWISANQ-UHFFFAOYSA-N O=C(C=CC(c1ncc[s]1)=C1)N1c1ccccc1 Chemical compound O=C(C=CC(c1ncc[s]1)=C1)N1c1ccccc1 HXUCVVBZWISANQ-UHFFFAOYSA-N 0.000 description 1
- CQBRXNOKJINDRW-UHFFFAOYSA-N O=C(C=CC(c1ncccn1)=C1)N1c(cc1)ccc1OC(F)(F)F Chemical compound O=C(C=CC(c1ncccn1)=C1)N1c(cc1)ccc1OC(F)(F)F CQBRXNOKJINDRW-UHFFFAOYSA-N 0.000 description 1
- PWNMBPLVSCOSEN-UHFFFAOYSA-N O=C(C=CC(c1ncccn1)=C1)N1c1ccccc1 Chemical compound O=C(C=CC(c1ncccn1)=C1)N1c1ccccc1 PWNMBPLVSCOSEN-UHFFFAOYSA-N 0.000 description 1
- QBIYGHDEISYYEK-UHFFFAOYSA-N O=C(c([nH]1)cc(C=C2)c1N(c(cc1)ccc1Cl)C2=O)NCc1ccncc1 Chemical compound O=C(c([nH]1)cc(C=C2)c1N(c(cc1)ccc1Cl)C2=O)NCc1ccncc1 QBIYGHDEISYYEK-UHFFFAOYSA-N 0.000 description 1
- JFZQAMUNIFCMFI-UHFFFAOYSA-N O=C(c([nH]1)cc(C=C2)c1N(c(cc1)ccc1F)C2=O)NCC1OCCC1 Chemical compound O=C(c([nH]1)cc(C=C2)c1N(c(cc1)ccc1F)C2=O)NCC1OCCC1 JFZQAMUNIFCMFI-UHFFFAOYSA-N 0.000 description 1
- WJJHADMPMKXWGB-UHFFFAOYSA-N O=C(c([nH]1)cc(C=C2)c1N(c(cc1)ccc1F)C2=O)NCc1nc2ccccc2[nH]1 Chemical compound O=C(c([nH]1)cc(C=C2)c1N(c(cc1)ccc1F)C2=O)NCc1nc2ccccc2[nH]1 WJJHADMPMKXWGB-UHFFFAOYSA-N 0.000 description 1
- JRQNTNNHIVDJQD-UHFFFAOYSA-N O=C(c([nH]1)cc(C=C2)c1N(c(cc1)ccc1OC(F)(F)F)C2=O)NCc1ccccc1 Chemical compound O=C(c([nH]1)cc(C=C2)c1N(c(cc1)ccc1OC(F)(F)F)C2=O)NCc1ccccc1 JRQNTNNHIVDJQD-UHFFFAOYSA-N 0.000 description 1
- QQLBSUIKAJDWEL-UHFFFAOYSA-N O=C(c([nH]1)cc(C=C2)c1N(c(cc1)ccc1OC(F)(F)F)C2=O)Nc1ncc[s]1 Chemical compound O=C(c([nH]1)cc(C=C2)c1N(c(cc1)ccc1OC(F)(F)F)C2=O)Nc1ncc[s]1 QQLBSUIKAJDWEL-UHFFFAOYSA-N 0.000 description 1
- QDEYGWAHFVFOAN-UHFFFAOYSA-N O=C(c([nH]1)cc(C=C2)c1N(c1ccc(C(F)(F)F)cc1)C2=O)NCCN1CCCC1 Chemical compound O=C(c([nH]1)cc(C=C2)c1N(c1ccc(C(F)(F)F)cc1)C2=O)NCCN1CCCC1 QDEYGWAHFVFOAN-UHFFFAOYSA-N 0.000 description 1
- HXWROQCOBKORSZ-UHFFFAOYSA-N OC(C=CC(c1ncc[o]1)=C1)N1c1ccccc1 Chemical compound OC(C=CC(c1ncc[o]1)=C1)N1c1ccccc1 HXWROQCOBKORSZ-UHFFFAOYSA-N 0.000 description 1
- SGCUGGBKTIYHNT-UHFFFAOYSA-N Oc1cccc(N(c([nH]c(C(N2CCCC2)=O)c2)c2C=C2)C2=O)c1 Chemical compound Oc1cccc(N(c([nH]c(C(N2CCCC2)=O)c2)c2C=C2)C2=O)c1 SGCUGGBKTIYHNT-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
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- 2009-06-03 JP JP2011512616A patent/JP5627574B2/ja not_active Expired - Fee Related
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- 2009-06-03 CA CA3034994A patent/CA3034994A1/en not_active Abandoned
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- 2009-06-03 ES ES09759347.9T patent/ES2567283T3/es active Active
- 2009-06-03 US US12/477,715 patent/US8304413B2/en not_active Ceased
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Also Published As
| Publication number | Publication date |
|---|---|
| MX2010012848A (es) | 2011-03-01 |
| EP2296653B1 (en) | 2016-01-27 |
| WO2009149188A1 (en) | 2009-12-10 |
| JP2014210809A (ja) | 2014-11-13 |
| JP2011522056A (ja) | 2011-07-28 |
| US20090318455A1 (en) | 2009-12-24 |
| CN102099036B (zh) | 2015-05-27 |
| US20140235637A1 (en) | 2014-08-21 |
| CA2726588A1 (en) | 2009-12-10 |
| USRE47142E1 (en) | 2018-11-27 |
| CN102099036A (zh) | 2011-06-15 |
| US8969347B2 (en) | 2015-03-03 |
| HK1155374A1 (zh) | 2012-05-18 |
| US9290450B2 (en) | 2016-03-22 |
| JP5627574B2 (ja) | 2014-11-19 |
| US8304413B2 (en) | 2012-11-06 |
| EP2296653A1 (en) | 2011-03-23 |
| EP2296653A4 (en) | 2012-03-07 |
| CA2726588C (en) | 2019-04-16 |
| US20130102597A1 (en) | 2013-04-25 |
| ES2567283T3 (es) | 2016-04-21 |
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