JP2013509442A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2013509442A5 JP2013509442A5 JP2012537157A JP2012537157A JP2013509442A5 JP 2013509442 A5 JP2013509442 A5 JP 2013509442A5 JP 2012537157 A JP2012537157 A JP 2012537157A JP 2012537157 A JP2012537157 A JP 2012537157A JP 2013509442 A5 JP2013509442 A5 JP 2013509442A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- fluoro
- heterocycle
- 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.)
- Ceased
Links
- 125000000217 alkyl group Chemical group 0.000 claims 41
- -1 —OH Chemical group 0.000 claims 39
- 125000000623 heterocyclic group Chemical group 0.000 claims 38
- 150000001875 compounds Chemical class 0.000 claims 30
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 20
- 229910052799 carbon Inorganic materials 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 20
- 229910052757 nitrogen Inorganic materials 0.000 claims 20
- 125000005843 halogen group Chemical group 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 125000001153 fluoro group Chemical group F* 0.000 claims 15
- 125000001424 substituent group Chemical group 0.000 claims 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- 150000002431 hydrogen Chemical group 0.000 claims 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 12
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 125000003003 spiro group Chemical group 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 0 **N1C(N=C(*)**2)=C2*C2C1(*)C2(*)* Chemical compound **N1C(N=C(*)**2)=C2*C2C1(*)C2(*)* 0.000 description 42
- YNAVUWVOSKDBBP-UHFFFAOYSA-N C1NCCOC1 Chemical compound C1NCCOC1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 5
- XWKFPIODWVPXLX-UHFFFAOYSA-N Cc1cnc(C)cc1 Chemical compound Cc1cnc(C)cc1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 5
- HPYNZHMRTTWQTB-UHFFFAOYSA-N Cc1c(C)nccc1 Chemical compound Cc1c(C)nccc1 HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 3
- BWZVCCNYKMEVEX-UHFFFAOYSA-N Cc1cc(C)nc(C)c1 Chemical compound Cc1cc(C)nc(C)c1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 3
- MXDRPNGTQDRKQM-UHFFFAOYSA-N Cc1cccnn1 Chemical compound Cc1cccnn1 MXDRPNGTQDRKQM-UHFFFAOYSA-N 0.000 description 3
- LVILGAOSPDLNRM-UHFFFAOYSA-N Cc1ccncn1 Chemical compound Cc1ccncn1 LVILGAOSPDLNRM-UHFFFAOYSA-N 0.000 description 3
- HWWYDZCSSYKIAD-UHFFFAOYSA-N Cc1cncc(C)c1 Chemical compound Cc1cncc(C)c1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 3
- VZWOXDYRBDIHMA-UHFFFAOYSA-N Cc1ncc[s]1 Chemical compound Cc1ncc[s]1 VZWOXDYRBDIHMA-UHFFFAOYSA-N 0.000 description 3
- ZICRALLMHKILDG-UHFFFAOYSA-N CC(C)c1ccn[nH]1 Chemical compound CC(C)c1ccn[nH]1 ZICRALLMHKILDG-UHFFFAOYSA-N 0.000 description 2
- WDWVZESPEBNLMI-UHFFFAOYSA-N CC(C)c1ccnc(OCC(CO)O)n1 Chemical compound CC(C)c1ccnc(OCC(CO)O)n1 WDWVZESPEBNLMI-UHFFFAOYSA-N 0.000 description 2
- KLNRGRAZDYBTKX-UHFFFAOYSA-N CC(C)c1nc(OCC(CO)O)cnc1 Chemical compound CC(C)c1nc(OCC(CO)O)cnc1 KLNRGRAZDYBTKX-UHFFFAOYSA-N 0.000 description 2
- NMILGIZTAZXMTM-UHFFFAOYSA-N CCCN1CCOCC1 Chemical compound CCCN1CCOCC1 NMILGIZTAZXMTM-UHFFFAOYSA-N 0.000 description 2
- WOHZPAAHKICDQP-UHFFFAOYSA-N CCN(CC1)CC1F Chemical compound CCN(CC1)CC1F WOHZPAAHKICDQP-UHFFFAOYSA-N 0.000 description 2
- HVCNXQOWACZAFN-UHFFFAOYSA-N CCN1CCOCC1 Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 2
- GFWWQGUAHZKPML-UHFFFAOYSA-N Cc(ncc(F)c1)c1F Chemical compound Cc(ncc(F)c1)c1F GFWWQGUAHZKPML-UHFFFAOYSA-N 0.000 description 2
- IRIHSZDBTACXCT-UHFFFAOYSA-N Cc(nccc1)c1F Chemical compound Cc(nccc1)c1F IRIHSZDBTACXCT-UHFFFAOYSA-N 0.000 description 2
- BAMPVSWRQZNDQC-UHFFFAOYSA-N Cc1c(C)[s]c(C)n1 Chemical compound Cc1c(C)[s]c(C)n1 BAMPVSWRQZNDQC-UHFFFAOYSA-N 0.000 description 2
- OBSLLHNATPQFMJ-UHFFFAOYSA-N Cc1c[s]c(C)n1 Chemical compound Cc1c[s]c(C)n1 OBSLLHNATPQFMJ-UHFFFAOYSA-N 0.000 description 2
- QMHIMXFNBOYPND-UHFFFAOYSA-N Cc1c[s]cn1 Chemical compound Cc1c[s]cn1 QMHIMXFNBOYPND-UHFFFAOYSA-N 0.000 description 2
- ZYFMSVSPGODTCZ-UHFFFAOYSA-N Cc1cc(N2CCOCC2)ncc1 Chemical compound Cc1cc(N2CCOCC2)ncc1 ZYFMSVSPGODTCZ-UHFFFAOYSA-N 0.000 description 2
- JBZFWJJJLREXJO-UHFFFAOYSA-N Cc1ccc(CN2CCOCC2)cc1 Chemical compound Cc1ccc(CN2CCOCC2)cc1 JBZFWJJJLREXJO-UHFFFAOYSA-N 0.000 description 2
- NWZGHEDTQILENR-UHFFFAOYSA-N Cc1ccc(CN2CCOCC2)nc1 Chemical compound Cc1ccc(CN2CCOCC2)nc1 NWZGHEDTQILENR-UHFFFAOYSA-N 0.000 description 2
- VJYXZJGDFJJDGF-UHFFFAOYSA-N Cc1cccc(C(F)(F)F)c1 Chemical compound Cc1cccc(C(F)(F)F)c1 VJYXZJGDFJJDGF-UHFFFAOYSA-N 0.000 description 2
- XQNQGAHLSZENHO-UHFFFAOYSA-N Cc1cccc(CN2CCOCC2)n1 Chemical compound Cc1cccc(CN2CCOCC2)n1 XQNQGAHLSZENHO-UHFFFAOYSA-N 0.000 description 2
- PGRMFTSBMKAGJM-UHFFFAOYSA-N Cc1cccc(N2CCCC2)n1 Chemical compound Cc1cccc(N2CCCC2)n1 PGRMFTSBMKAGJM-UHFFFAOYSA-N 0.000 description 2
- DACONEDXUXDOIE-UHFFFAOYSA-N Cc1cccc(N2CCOCC2)n1 Chemical compound Cc1cccc(N2CCOCC2)n1 DACONEDXUXDOIE-UHFFFAOYSA-N 0.000 description 2
- XKVUYEYANWFIJX-UHFFFAOYSA-N Cc1ccn[nH]1 Chemical compound Cc1ccn[nH]1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 2
- AGQOIYCTCOEHGR-UHFFFAOYSA-N Cc1ccn[o]1 Chemical compound Cc1ccn[o]1 AGQOIYCTCOEHGR-UHFFFAOYSA-N 0.000 description 2
- LBBKWEDRPDGXPM-UHFFFAOYSA-N Cc1ccn[s]1 Chemical compound Cc1ccn[s]1 LBBKWEDRPDGXPM-UHFFFAOYSA-N 0.000 description 2
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N Cc1ccnc(C)c1 Chemical compound Cc1ccnc(C)c1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
- WVUHHPQQQLBMOE-UHFFFAOYSA-N Cc1cnc(C)[s]1 Chemical compound Cc1cnc(C)[s]1 WVUHHPQQQLBMOE-UHFFFAOYSA-N 0.000 description 2
- TWGNOYAGHYUFFR-UHFFFAOYSA-N Cc1cncnc1 Chemical compound Cc1cncnc1 TWGNOYAGHYUFFR-UHFFFAOYSA-N 0.000 description 2
- SGDYCKIHBXCPAK-UHFFFAOYSA-N Cc1ncc(CN2CCCC2)cc1 Chemical compound Cc1ncc(CN2CCCC2)cc1 SGDYCKIHBXCPAK-UHFFFAOYSA-N 0.000 description 2
- PZKFSRWSQOQYNR-UHFFFAOYSA-N Cc1ncn[nH]1 Chemical compound Cc1ncn[nH]1 PZKFSRWSQOQYNR-UHFFFAOYSA-N 0.000 description 2
- QLXOJLUHWBDVKZ-UHFFFAOYSA-N Cc1ncn[s]1 Chemical compound Cc1ncn[s]1 QLXOJLUHWBDVKZ-UHFFFAOYSA-N 0.000 description 2
- CURYZAZKVRLRBB-UHFFFAOYSA-N FC(CC1)CN1c1c(C2)c2ccc1 Chemical compound FC(CC1)CN1c1c(C2)c2ccc1 CURYZAZKVRLRBB-UHFFFAOYSA-N 0.000 description 2
- JQSLDFFVNADTPO-WNEGIOFOSA-N C/C=C(/CCCN)\N(C)/N=C/C Chemical compound C/C=C(/CCCN)\N(C)/N=C/C JQSLDFFVNADTPO-WNEGIOFOSA-N 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N C1CC=CCC1 Chemical compound C1CC=CCC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- CGHIPELJOKMAEO-UHFFFAOYSA-N CC(C(C1)=C(C)CCC1F)F Chemical compound CC(C(C1)=C(C)CCC1F)F CGHIPELJOKMAEO-UHFFFAOYSA-N 0.000 description 1
- QBWHFKOHEXJZSV-UHFFFAOYSA-N CC(C)(C)c1c(C)[n](C)nc1 Chemical compound CC(C)(C)c1c(C)[n](C)nc1 QBWHFKOHEXJZSV-UHFFFAOYSA-N 0.000 description 1
- KKXCKCSYDIDGEX-UHFFFAOYSA-N CC(C)(C1)NC(C)(C)CC1C(C)=C Chemical compound CC(C)(C1)NC(C)(C)CC1C(C)=C KKXCKCSYDIDGEX-UHFFFAOYSA-N 0.000 description 1
- UMBUOZPBOPQESN-UHFFFAOYSA-N CC(C)N(C1)CC1(CC1)S1(=O)=O Chemical compound CC(C)N(C1)CC1(CC1)S1(=O)=O UMBUOZPBOPQESN-UHFFFAOYSA-N 0.000 description 1
- KZESYXUKHKOJBX-UHFFFAOYSA-N CC(C)c(c(F)c(c(F)c1F)F)c1F Chemical compound CC(C)c(c(F)c(c(F)c1F)F)c1F KZESYXUKHKOJBX-UHFFFAOYSA-N 0.000 description 1
- JPDPRXXLFYTTRV-UHFFFAOYSA-N CC(C)c1c(C)[o]nc1C Chemical compound CC(C)c1c(C)[o]nc1C JPDPRXXLFYTTRV-UHFFFAOYSA-N 0.000 description 1
- RMMFFMJLIHITAH-UHFFFAOYSA-N CC(C)c1c[n](C)nc1 Chemical compound CC(C)c1c[n](C)nc1 RMMFFMJLIHITAH-UHFFFAOYSA-N 0.000 description 1
- RZXLGATYHGEUHY-UHFFFAOYSA-N CC(C)c1c[o]nc1 Chemical compound CC(C)c1c[o]nc1 RZXLGATYHGEUHY-UHFFFAOYSA-N 0.000 description 1
- VGIPFSZAJPAOPJ-UHFFFAOYSA-N CC(C)c1cc(C)n[n]1C Chemical compound CC(C)c1cc(C)n[n]1C VGIPFSZAJPAOPJ-UHFFFAOYSA-N 0.000 description 1
- HIMSWDGNMPGEKG-UHFFFAOYSA-N CC(C)c1ccnc(OC)n1 Chemical compound CC(C)c1ccnc(OC)n1 HIMSWDGNMPGEKG-UHFFFAOYSA-N 0.000 description 1
- BMWFZLFBKVCXOQ-UHFFFAOYSA-N CC(C)c1cncc(CN2CCC2)n1 Chemical compound CC(C)c1cncc(CN2CCC2)n1 BMWFZLFBKVCXOQ-UHFFFAOYSA-N 0.000 description 1
- IMRJUCSOJVIHRK-UHFFFAOYSA-N CC(C)c1nc(OCC(CO)O)cc(C)n1 Chemical compound CC(C)c1nc(OCC(CO)O)cc(C)n1 IMRJUCSOJVIHRK-UHFFFAOYSA-N 0.000 description 1
- WVSAGBHAVUXHJC-UHFFFAOYSA-N CC(C)c1nccc(OCC(COC)O)c1 Chemical compound CC(C)c1nccc(OCC(COC)O)c1 WVSAGBHAVUXHJC-UHFFFAOYSA-N 0.000 description 1
- OVVUKJMVOPYVPB-UHFFFAOYSA-N CC(C1)C1(C)c1n[o]cc1 Chemical compound CC(C1)C1(C)c1n[o]cc1 OVVUKJMVOPYVPB-UHFFFAOYSA-N 0.000 description 1
- RQHPWKYMWIAXHM-UHFFFAOYSA-N CC(CC1)=CC=C1C(F)(F)F Chemical compound CC(CC1)=CC=C1C(F)(F)F RQHPWKYMWIAXHM-UHFFFAOYSA-N 0.000 description 1
- OPPDHIMEIJAYME-UHFFFAOYSA-N CC(CC1)C(C)CC1OCC(CO)O Chemical compound CC(CC1)C(C)CC1OCC(CO)O OPPDHIMEIJAYME-UHFFFAOYSA-N 0.000 description 1
- CUZAXCLLHKRCLZ-UHFFFAOYSA-N CC(CC1)C=CC1OCC(CO)O Chemical compound CC(CC1)C=CC1OCC(CO)O CUZAXCLLHKRCLZ-UHFFFAOYSA-N 0.000 description 1
- RKIRQSVYPLZQLD-UHFFFAOYSA-N CC(CC=C1)C=C1OC Chemical compound CC(CC=C1)C=C1OC RKIRQSVYPLZQLD-UHFFFAOYSA-N 0.000 description 1
- AMXIRIUXSPTQCN-UHFFFAOYSA-N CC(CCC1)C=C1C(F)(F)F Chemical compound CC(CCC1)C=C1C(F)(F)F AMXIRIUXSPTQCN-UHFFFAOYSA-N 0.000 description 1
- XNGBTKJFUJSUOU-UHFFFAOYSA-N CC(CCC1OCC(CO)O)C=C1C(F)(F)F Chemical compound CC(CCC1OCC(CO)O)C=C1C(F)(F)F XNGBTKJFUJSUOU-UHFFFAOYSA-N 0.000 description 1
- CMGZNIYYLCSKBD-UHFFFAOYSA-N CC(CCC=C1)=C1OC(F)(F)F Chemical compound CC(CCC=C1)=C1OC(F)(F)F CMGZNIYYLCSKBD-UHFFFAOYSA-N 0.000 description 1
- QGLBZNZGBLRJGS-UHFFFAOYSA-N CC(CCO1)C1=O Chemical compound CC(CCO1)C1=O QGLBZNZGBLRJGS-UHFFFAOYSA-N 0.000 description 1
- RALRWGYKDGGAHH-UHFFFAOYSA-N CC(N(CC1)CC1F)=C Chemical compound CC(N(CC1)CC1F)=C RALRWGYKDGGAHH-UHFFFAOYSA-N 0.000 description 1
- RTANPEKNOJJKBG-UHFFFAOYSA-N CC1=CC(C)=NC=CC1 Chemical compound CC1=CC(C)=NC=CC1 RTANPEKNOJJKBG-UHFFFAOYSA-N 0.000 description 1
- DONXDEXIIVWNCP-UHFFFAOYSA-N CC1=CCCC=C1OCC(CO)O Chemical compound CC1=CCCC=C1OCC(CO)O DONXDEXIIVWNCP-UHFFFAOYSA-N 0.000 description 1
- CHTUGUJVXTYWML-UHFFFAOYSA-N CC1=NC(C)=CCC=C1 Chemical compound CC1=NC(C)=CCC=C1 CHTUGUJVXTYWML-UHFFFAOYSA-N 0.000 description 1
- VWSLLSXLURJCDF-UHFFFAOYSA-N CC1=NCCN1 Chemical compound CC1=NCCN1 VWSLLSXLURJCDF-UHFFFAOYSA-N 0.000 description 1
- ABYIGSTWTBEAOS-UHFFFAOYSA-N CC1C(C)=CC(OCC(CO)O)=C=C1 Chemical compound CC1C(C)=CC(OCC(CO)O)=C=C1 ABYIGSTWTBEAOS-UHFFFAOYSA-N 0.000 description 1
- MGULZBCTPDFXHR-UHFFFAOYSA-N CC1C(CC(C)=C)=C(C)C=NC1 Chemical compound CC1C(CC(C)=C)=C(C)C=NC1 MGULZBCTPDFXHR-UHFFFAOYSA-N 0.000 description 1
- LAQPDMGSVFHQPT-UHFFFAOYSA-N CC1C=C(C(F)(F)F)C(OCC(CO)O)=CC1 Chemical compound CC1C=C(C(F)(F)F)C(OCC(CO)O)=CC1 LAQPDMGSVFHQPT-UHFFFAOYSA-N 0.000 description 1
- UWIDHRGMLKOWDP-UHFFFAOYSA-N CC1C=CC=CC1C(F)(F)F Chemical compound CC1C=CC=CC1C(F)(F)F UWIDHRGMLKOWDP-UHFFFAOYSA-N 0.000 description 1
- RUKXYQDREVCKFA-UHFFFAOYSA-N CC1CC(OCC(CO)O)=CCC1 Chemical compound CC1CC(OCC(CO)O)=CCC1 RUKXYQDREVCKFA-UHFFFAOYSA-N 0.000 description 1
- WAHFYBHQGSHRJD-UHFFFAOYSA-N CCCCc1nnc[s]1 Chemical compound CCCCc1nnc[s]1 WAHFYBHQGSHRJD-UHFFFAOYSA-N 0.000 description 1
- VZIIVQUZIOHZIL-UHFFFAOYSA-N CCc1cccc(CN(C)C)c1 Chemical compound CCc1cccc(CN(C)C)c1 VZIIVQUZIOHZIL-UHFFFAOYSA-N 0.000 description 1
- OPTJORCKCHZSIH-UHFFFAOYSA-N CCc1ccnc2c1nccc2 Chemical compound CCc1ccnc2c1nccc2 OPTJORCKCHZSIH-UHFFFAOYSA-N 0.000 description 1
- LKHMPQATAWRVRI-UHFFFAOYSA-N CN1CC=[O]CC1 Chemical compound CN1CC=[O]CC1 LKHMPQATAWRVRI-UHFFFAOYSA-N 0.000 description 1
- JAEQOSKUYPMJAT-UHFFFAOYSA-N COCCN1CCOCC1 Chemical compound COCCN1CCOCC1 JAEQOSKUYPMJAT-UHFFFAOYSA-N 0.000 description 1
- ZAZJGDUCNIVGED-UHFFFAOYSA-N C[n]1nccc1C=S Chemical compound C[n]1nccc1C=S ZAZJGDUCNIVGED-UHFFFAOYSA-N 0.000 description 1
- YYUSFELHBJJWPU-UHFFFAOYSA-N Cc(c(C(F)(F)F)c1)ccc1O Chemical compound Cc(c(C(F)(F)F)c1)ccc1O YYUSFELHBJJWPU-UHFFFAOYSA-N 0.000 description 1
- YEZPWKIUIAEMDJ-UHFFFAOYSA-N Cc(cc(cc1)[F]C)c1F Chemical compound Cc(cc(cc1)[F]C)c1F YEZPWKIUIAEMDJ-UHFFFAOYSA-N 0.000 description 1
- XURBBZGVJHPSFN-UHFFFAOYSA-N Cc(cc1)c(C(F)(F)F)cc1N1CCOCC1 Chemical compound Cc(cc1)c(C(F)(F)F)cc1N1CCOCC1 XURBBZGVJHPSFN-UHFFFAOYSA-N 0.000 description 1
- IKNQPNLSEBWZKX-UHFFFAOYSA-N Cc(cc1)cc(Cl)c1F Chemical compound Cc(cc1)cc(Cl)c1F IKNQPNLSEBWZKX-UHFFFAOYSA-N 0.000 description 1
- VCPZYLBOSFKSBF-UHFFFAOYSA-N Cc(cc1)cc2c1N(C)CCO2 Chemical compound Cc(cc1)cc2c1N(C)CCO2 VCPZYLBOSFKSBF-UHFFFAOYSA-N 0.000 description 1
- GHPODDMCSOYWNE-UHFFFAOYSA-N Cc(cc1)cc2c1OCO2 Chemical compound Cc(cc1)cc2c1OCO2 GHPODDMCSOYWNE-UHFFFAOYSA-N 0.000 description 1
- LXAHHHIGZXPRKQ-UHFFFAOYSA-N Cc(cc1)ncc1F Chemical compound Cc(cc1)ncc1F LXAHHHIGZXPRKQ-UHFFFAOYSA-N 0.000 description 1
- UHIGHLGTNVYXOP-UHFFFAOYSA-N Cc(cc1F)cc(F)c1F Chemical compound Cc(cc1F)cc(F)c1F UHIGHLGTNVYXOP-UHFFFAOYSA-N 0.000 description 1
- FZMPLKVGINKUJZ-UHFFFAOYSA-N Cc(cc1F)ccc1F Chemical compound Cc(cc1F)ccc1F FZMPLKVGINKUJZ-UHFFFAOYSA-N 0.000 description 1
- MPXDAIBTYWGBSL-UHFFFAOYSA-N Cc(ccc(F)c1)c1F Chemical compound Cc(ccc(F)c1)c1F MPXDAIBTYWGBSL-UHFFFAOYSA-N 0.000 description 1
- WZMOEPZZTTWDIA-UHFFFAOYSA-N Cc(ccnc1)c1F Chemical compound Cc(ccnc1)c1F WZMOEPZZTTWDIA-UHFFFAOYSA-N 0.000 description 1
- FOAKHDIVYPQRJT-UHFFFAOYSA-N Cc(nc1)ccc1[F]C Chemical compound Cc(nc1)ccc1[F]C FOAKHDIVYPQRJT-UHFFFAOYSA-N 0.000 description 1
- WFZHSHSZZPXBKG-UHFFFAOYSA-N Cc1c(C(F)(F)F)ccc(OCCNCCO)c1 Chemical compound Cc1c(C(F)(F)F)ccc(OCCNCCO)c1 WFZHSHSZZPXBKG-UHFFFAOYSA-N 0.000 description 1
- DGOGETLEZMHZSI-UHFFFAOYSA-N Cc1c(C(N(C)C)=O)[s]c(C)n1 Chemical compound Cc1c(C(N(C)C)=O)[s]c(C)n1 DGOGETLEZMHZSI-UHFFFAOYSA-N 0.000 description 1
- MGHKWBQZEBMFOH-UHFFFAOYSA-N Cc1c(C)[o]nc1C Chemical compound Cc1c(C)[o]nc1C MGHKWBQZEBMFOH-UHFFFAOYSA-N 0.000 description 1
- WFDDXLYAFSELPR-UHFFFAOYSA-N Cc1c(C)[s]c(NCCO)n1 Chemical compound Cc1c(C)[s]c(NCCO)n1 WFDDXLYAFSELPR-UHFFFAOYSA-N 0.000 description 1
- RIKMMFOAQPJVMX-UHFFFAOYSA-N Cc1c[nH]nc1 Chemical compound Cc1c[nH]nc1 RIKMMFOAQPJVMX-UHFFFAOYSA-N 0.000 description 1
- ZQESOGMUGVKUNW-UHFFFAOYSA-N Cc1cc(CN2CCOCC2)ncc1 Chemical compound Cc1cc(CN2CCOCC2)ncc1 ZQESOGMUGVKUNW-UHFFFAOYSA-N 0.000 description 1
- NWOHVQVBCFDBBP-UHFFFAOYSA-N Cc1cc(F)cc([F]C)c1 Chemical compound Cc1cc(F)cc([F]C)c1 NWOHVQVBCFDBBP-UHFFFAOYSA-N 0.000 description 1
- CKQXPRSCSFUGRC-UHFFFAOYSA-N Cc1cc(F)cnc1 Chemical compound Cc1cc(F)cnc1 CKQXPRSCSFUGRC-UHFFFAOYSA-N 0.000 description 1
- OGQWJMBRSUDXDK-UHFFFAOYSA-N Cc1cc(N2CCCC2)ncc1 Chemical compound Cc1cc(N2CCCC2)ncc1 OGQWJMBRSUDXDK-UHFFFAOYSA-N 0.000 description 1
- YZCGXVAUCXZDKF-UHFFFAOYSA-N Cc1cc(OCC(CO)O)ncc1 Chemical compound Cc1cc(OCC(CO)O)ncc1 YZCGXVAUCXZDKF-UHFFFAOYSA-N 0.000 description 1
- WWYQUVRQRXJULJ-UHFFFAOYSA-N Cc1cc(OCCN2C)c2nc1 Chemical compound Cc1cc(OCCN2C)c2nc1 WWYQUVRQRXJULJ-UHFFFAOYSA-N 0.000 description 1
- HYRMCQIKPBKIFA-UHFFFAOYSA-N Cc1ccc(C(F)[F]C)cc1 Chemical compound Cc1ccc(C(F)[F]C)cc1 HYRMCQIKPBKIFA-UHFFFAOYSA-N 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N Cc1ccc(C)nc1C Chemical compound Cc1ccc(C)nc1C UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- PIEPDUZQVDENCS-UHFFFAOYSA-N Cc1ccc(CN2CCOCC2)cn1 Chemical compound Cc1ccc(CN2CCOCC2)cn1 PIEPDUZQVDENCS-UHFFFAOYSA-N 0.000 description 1
- HHFJHCXBGHXHLU-UHFFFAOYSA-N Cc1ccc2NCCOc2c1 Chemical compound Cc1ccc2NCCOc2c1 HHFJHCXBGHXHLU-UHFFFAOYSA-N 0.000 description 1
- QUTSDZPSPCZXQP-UHFFFAOYSA-N Cc1cccc(CN2)c1C2=O Chemical compound Cc1cccc(CN2)c1C2=O QUTSDZPSPCZXQP-UHFFFAOYSA-N 0.000 description 1
- UWGGDBZLFAXETC-UHFFFAOYSA-N Cc1cccc(CN2CCCC2)n1 Chemical compound Cc1cccc(CN2CCCC2)n1 UWGGDBZLFAXETC-UHFFFAOYSA-N 0.000 description 1
- GIIBAUDXEXFBHL-UHFFFAOYSA-N Cc1cccc(OCC(CO)O)c1 Chemical compound Cc1cccc(OCC(CO)O)c1 GIIBAUDXEXFBHL-UHFFFAOYSA-N 0.000 description 1
- SLOSZSJYGVTRDR-UHFFFAOYSA-N Cc1cccc(OCC(CO)O)n1 Chemical compound Cc1cccc(OCC(CO)O)n1 SLOSZSJYGVTRDR-UHFFFAOYSA-N 0.000 description 1
- SLOSZSJYGVTRDR-MRVPVSSYSA-N Cc1cccc(OC[C@@H](CO)O)n1 Chemical compound Cc1cccc(OC[C@@H](CO)O)n1 SLOSZSJYGVTRDR-MRVPVSSYSA-N 0.000 description 1
- SLOSZSJYGVTRDR-QMMMGPOBSA-N Cc1cccc(OC[C@H](CO)O)n1 Chemical compound Cc1cccc(OC[C@H](CO)O)n1 SLOSZSJYGVTRDR-QMMMGPOBSA-N 0.000 description 1
- LSZQMSSIUQNTDX-UHFFFAOYSA-N Cc1ccn[n]1C Chemical compound Cc1ccn[n]1C LSZQMSSIUQNTDX-UHFFFAOYSA-N 0.000 description 1
- CBBHTELYBBUCAI-UHFFFAOYSA-N Cc1ccnc(CN2CCC2)n1 Chemical compound Cc1ccnc(CN2CCC2)n1 CBBHTELYBBUCAI-UHFFFAOYSA-N 0.000 description 1
- NHABXXMJWHQLHE-UHFFFAOYSA-N Cc1ccnc(CN2CCOCC2)n1 Chemical compound Cc1ccnc(CN2CCOCC2)n1 NHABXXMJWHQLHE-UHFFFAOYSA-N 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N Cc1cnc[nH]1 Chemical compound Cc1cnc[nH]1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- ZYMHCFYHVYGFMS-UHFFFAOYSA-N Cc1cnc[o]1 Chemical compound Cc1cnc[o]1 ZYMHCFYHVYGFMS-UHFFFAOYSA-N 0.000 description 1
- RLYUNPNLXMSXAX-UHFFFAOYSA-N Cc1cnc[s]1 Chemical compound Cc1cnc[s]1 RLYUNPNLXMSXAX-UHFFFAOYSA-N 0.000 description 1
- QEKZJNUCTSUAPX-UHFFFAOYSA-N Cc1cncc(CN2CCOCC2)n1 Chemical compound Cc1cncc(CN2CCOCC2)n1 QEKZJNUCTSUAPX-UHFFFAOYSA-N 0.000 description 1
- CAWHJQAVHZEVTJ-UHFFFAOYSA-N Cc1cnccn1 Chemical compound Cc1cnccn1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 1
- NODLZCJDRXTSJO-UHFFFAOYSA-N Cc1n[n](C)cc1 Chemical compound Cc1n[n](C)cc1 NODLZCJDRXTSJO-UHFFFAOYSA-N 0.000 description 1
- FICAQKBMCKEFDI-UHFFFAOYSA-N Cc1n[o]c(C)c1 Chemical compound Cc1n[o]c(C)c1 FICAQKBMCKEFDI-UHFFFAOYSA-N 0.000 description 1
- KJJMYYHQVJTGRW-UHFFFAOYSA-N Cc1nc(CN2CCC2)c[s]1 Chemical compound Cc1nc(CN2CCC2)c[s]1 KJJMYYHQVJTGRW-UHFFFAOYSA-N 0.000 description 1
- CDOSGNCKLTWOGE-UHFFFAOYSA-N Cc1nc(CN2CCOCC2)c[s]1 Chemical compound Cc1nc(CN2CCOCC2)c[s]1 CDOSGNCKLTWOGE-UHFFFAOYSA-N 0.000 description 1
- LCZUOKDVTBMCMX-UHFFFAOYSA-N Cc1ncc(C)nc1 Chemical compound Cc1ncc(C)nc1 LCZUOKDVTBMCMX-UHFFFAOYSA-N 0.000 description 1
- JQPJLAIKWBMUGT-UHFFFAOYSA-N Cc1ncc(CN2CCC2)[s]1 Chemical compound Cc1ncc(CN2CCC2)[s]1 JQPJLAIKWBMUGT-UHFFFAOYSA-N 0.000 description 1
- UFOYKQDCSIUCJT-UHFFFAOYSA-N Cc1ncc(CN2CCCC2)[s]1 Chemical compound Cc1ncc(CN2CCCC2)[s]1 UFOYKQDCSIUCJT-UHFFFAOYSA-N 0.000 description 1
- LVKJXFHAFLLIET-UHFFFAOYSA-N Cc1ncc(CN2CCOCC2)[s]1 Chemical compound Cc1ncc(CN2CCOCC2)[s]1 LVKJXFHAFLLIET-UHFFFAOYSA-N 0.000 description 1
- AFTHDBUWROCKNF-UHFFFAOYSA-N Cc1ncc([F]C)[s]1 Chemical compound Cc1ncc([F]C)[s]1 AFTHDBUWROCKNF-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N Cc1ncc[nH]1 Chemical compound Cc1ncc[nH]1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- ZCHCHJQEWYIJDQ-UHFFFAOYSA-N Cc1ncc[o]1 Chemical compound Cc1ncc[o]1 ZCHCHJQEWYIJDQ-UHFFFAOYSA-N 0.000 description 1
- VAWGXUBCGWYGEQ-UHFFFAOYSA-N Cc1nccc(C(F)(F)F)c1 Chemical compound Cc1nccc(C(F)(F)F)c1 VAWGXUBCGWYGEQ-UHFFFAOYSA-N 0.000 description 1
- KMHPWCYEDFBGFZ-UHFFFAOYSA-N Cc1nccc(CN2CCC2)c1 Chemical compound Cc1nccc(CN2CCC2)c1 KMHPWCYEDFBGFZ-UHFFFAOYSA-N 0.000 description 1
- DNBMKZDJEGPIQO-UHFFFAOYSA-N Cc1nccc(CN2CCOCC2)c1 Chemical compound Cc1nccc(CN2CCOCC2)c1 DNBMKZDJEGPIQO-UHFFFAOYSA-N 0.000 description 1
- LNJMHEJAYSYZKK-UHFFFAOYSA-N Cc1ncccn1 Chemical compound Cc1ncccn1 LNJMHEJAYSYZKK-UHFFFAOYSA-N 0.000 description 1
- GGFJPYWUQCOYLQ-UHFFFAOYSA-N Cc1ncnc(OC)c1 Chemical compound Cc1ncnc(OC)c1 GGFJPYWUQCOYLQ-UHFFFAOYSA-N 0.000 description 1
- YVDWFZIVIIKYBQ-UHFFFAOYSA-N Cc1nnc(C)[o]1 Chemical compound Cc1nnc(C)[o]1 YVDWFZIVIIKYBQ-UHFFFAOYSA-N 0.000 description 1
- JXQGICFGPUAVLJ-UHFFFAOYSA-N Cc1nnc(C)[s]1 Chemical compound Cc1nnc(C)[s]1 JXQGICFGPUAVLJ-UHFFFAOYSA-N 0.000 description 1
- ZMSIFDIKIXVLDF-UHFFFAOYSA-N Cc1nnc[o]1 Chemical compound Cc1nnc[o]1 ZMSIFDIKIXVLDF-UHFFFAOYSA-N 0.000 description 1
- RQSCFNPNNLWQBJ-UHFFFAOYSA-N Cc1nnc[s]1 Chemical compound Cc1nnc[s]1 RQSCFNPNNLWQBJ-UHFFFAOYSA-N 0.000 description 1
- ZJACKOJGPVCICU-UHFFFAOYSA-N FC(c1ncc(C2CC2)cc1)(F)F Chemical compound FC(c1ncc(C2CC2)cc1)(F)F ZJACKOJGPVCICU-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25626909P | 2009-10-29 | 2009-10-29 | |
| US61/256,269 | 2009-10-29 | ||
| PCT/US2010/054880 WO2011059839A1 (en) | 2009-10-29 | 2010-10-29 | Bicyclic pyridines and analogs as sirtuin modulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013509442A JP2013509442A (ja) | 2013-03-14 |
| JP2013509442A5 true JP2013509442A5 (https=) | 2013-12-05 |
Family
ID=43991957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012537157A Ceased JP2013509442A (ja) | 2009-10-29 | 2010-10-29 | サーチュイン調節因子としての二環式ピリジンおよび類似体 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9556201B2 (https=) |
| EP (1) | EP2493888B1 (https=) |
| JP (1) | JP2013509442A (https=) |
| KR (1) | KR20120092141A (https=) |
| CN (1) | CN102725291B (https=) |
| AU (1) | AU2010319842A1 (https=) |
| BR (1) | BR112012010010A2 (https=) |
| CA (1) | CA2779303A1 (https=) |
| ES (1) | ES2574927T3 (https=) |
| IL (1) | IL219372A0 (https=) |
| IN (1) | IN2012DN03799A (https=) |
| MX (1) | MX2012004995A (https=) |
| RU (1) | RU2550821C2 (https=) |
| WO (1) | WO2011059839A1 (https=) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CL2008003651A1 (es) | 2007-12-10 | 2009-06-19 | Novartis Ag | Compuestos derivados de 3,5-diamino-6-cloropirazinamida sustituida; composicion farmaceutica; combinacion farmaceutica; y uso en el tratamiento de una condición inflamatoria o alergica, en particular una enfermedad inflamatoria u obstructiva de las vias respiratorias. |
| MX2011003373A (es) | 2008-09-29 | 2011-06-09 | Sirtris Pharmaceuticals Inc | Quinazolinona, quinolona y analogos relacionados como moduladores de sirtuina. |
| NZ631258A (en) * | 2012-04-25 | 2016-11-25 | Takeda Pharmaceuticals Co | Nitrogenated heterocyclic compound |
| WO2013169704A2 (en) | 2012-05-08 | 2013-11-14 | Merck Sharp & Dohme Corp. | TETRAHYDRONAPHTHYRIDINE AND RELATED BICYCLIC COMPOUNDS FOR INHIBITION OF RORgamma ACTIVITY AND THE TREATMENT OF DISEASE |
| JP6242868B2 (ja) | 2012-05-08 | 2017-12-06 | リセラ・コーポレイションＬｙｃｅｒａ Ｃｏｒｐｏｒａｔｉｏｎ | ＲＯＲγのアゴニストとしての使用のためおよび疾患の処置のためのテトラヒドロ［１，８］ナフチリジンスルホンアミドおよび関連化合物 |
| WO2014010732A1 (ja) | 2012-07-13 | 2014-01-16 | 武田薬品工業株式会社 | 複素環化合物 |
| BR112015002493A8 (pt) * | 2012-08-30 | 2019-07-30 | Hoffmann La Roche | composto, composição farmacêutica, processo para a preparação de uma composição farmacêutica, kit e uso de um composto” |
| CN102977117A (zh) * | 2012-11-26 | 2013-03-20 | 盛世泰科生物医药技术(苏州)有限公司 | 一种6-溴-2,2-二甲基-2h-吡啶并[3,2-b][1,4]恶嗪-3(4h)-酮的合成方法 |
| GEP201606554B (en) * | 2012-12-26 | 2016-10-10 | Takeda Pharmaceuticals Co | Nitrogenated heterocyclic compound |
| EP2975031A4 (en) | 2013-03-14 | 2017-04-19 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| CN105392788B (zh) * | 2013-05-13 | 2018-10-23 | 葛兰素史密斯克莱有限责任公司 | 用作沉默调节蛋白调节剂的取代的桥连脲类似物 |
| WO2016081692A2 (en) * | 2014-11-19 | 2016-05-26 | Glaxosmithkline Llc | Substituted bridged urea analogs as sirtuin modulators |
| EP3018123B1 (en) | 2013-07-03 | 2023-05-10 | Takeda Pharmaceutical Company Limited | Amide compound |
| JP6427491B2 (ja) | 2013-07-03 | 2018-11-21 | 武田薬品工業株式会社 | 複素環化合物 |
| SI3050878T1 (sl) | 2013-09-24 | 2022-01-31 | Fujifilm Corporation | Nova dušik-vsebujoča spojina ali njena sol ali kovinski kompleks le-te |
| US10172915B2 (en) | 2013-10-20 | 2019-01-08 | Duke University | Methods and compositions for activation of sirtuins with Annexin A1 peptides |
| TN2016000115A1 (en) | 2013-10-25 | 2017-07-05 | Novartis Ag | Ring-fused bicyclic pyridyl derivatives as fgfr4 inhibitors. |
| WO2015095788A1 (en) | 2013-12-20 | 2015-06-25 | Merck Sharp & Dohme Corp. | 2-ACYLAMIDOMETHYL AND SULFONYLAMIDOMETHYL BENZOXAZINE CARBAMATES FOR INHIBITION OF RORgamma ACTIVITY AND THE TREATMENT OF DISEASE |
| US9783511B2 (en) | 2013-12-20 | 2017-10-10 | Lycera Corporation | Carbamate benzoxazine propionic acids and acid derivatives for modulation of RORgamma activity and the treatment of disease |
| US9809561B2 (en) | 2013-12-20 | 2017-11-07 | Merck Sharp & Dohme Corp. | Tetrahydronaphthyridine, benzoxazine, aza-benzoxazine and related bicyclic compounds for inhibition of RORgamma activity and the treatment of disease |
| US10087151B2 (en) | 2014-01-09 | 2018-10-02 | The J. David Gladstone Institutes, A Testimentary Trust Established Under The Will Of J. David Gladstone | Substituted benzoxazine and related compounds |
| JP2017507950A (ja) | 2014-02-27 | 2017-03-23 | リセラ・コーポレイションＬｙｃｅｒａ Ｃｏｒｐｏｒａｔｉｏｎ | レチノイン酸受容体関連オーファン受容体ガンマのアゴニストを使用する養子細胞療法及び関連治療方法 |
| JP2017114764A (ja) * | 2014-04-25 | 2017-06-29 | 武田薬品工業株式会社 | 片頭痛治療剤 |
| JP6523337B2 (ja) | 2014-05-05 | 2019-05-29 | リセラ・コーポレイションＬｙｃｅｒａ Ｃｏｒｐｏｒａｔｉｏｎ | ＲＯＲγのアゴニストとしての使用及び疾患治療のためのベンゼンスルホンアミド及び関連化合物 |
| EP3140291A4 (en) | 2014-05-05 | 2018-01-10 | Lycera Corporation | Tetrahydroquinoline sulfonamide and related compounds for use as agonists of rory and the treatment of disease |
| KR20170012449A (ko) | 2014-06-02 | 2017-02-02 | 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 | 결정질 베타-d-니코틴아미드 리보시드의 제조 및 용도 |
| CA2951287A1 (en) | 2014-06-06 | 2015-12-10 | Glaxosmithkline Intellectual Property (No. 2) Limited | Nicotinamide riboside analogs and pharmaceutical compositions and uses thereof |
| JP6585167B2 (ja) | 2014-10-03 | 2019-10-02 | ノバルティス アーゲー | Ｆｇｆｒ４阻害剤としての縮環二環式ピリジル誘導体の使用 |
| PE20171257A1 (es) * | 2014-11-19 | 2017-08-28 | Glaxosmithkline Intellectual Property (No 2) Ltd | Analogos de urea unidos sustituidos como moduladores de sirtuina |
| CA2975997A1 (en) | 2015-02-11 | 2016-08-18 | Merck Sharp & Dohme Corp. | Substituted pyrazole compounds as rorgammat inhibitors and uses thereof |
| US9802917B2 (en) | 2015-03-25 | 2017-10-31 | Novartis Ag | Particles of N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-formyl-6-((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide |
| US10421751B2 (en) | 2015-05-05 | 2019-09-24 | Lycera Corporation | Dihydro-2H-benzo[b][1,4]oxazine sulfonamide and related compounds for use as agonists of RORγ and the treatment of disease |
| AU2016276947A1 (en) | 2015-06-11 | 2017-12-14 | Lycera Corporation | Aryl dihydro-2h-benzo[b][1,4]oxazine sulfonamide and related compounds for use as agonists of RORy and the treatment of disease |
| EP3368535B1 (en) | 2015-10-27 | 2020-12-02 | Merck Sharp & Dohme Corp. | Heteroaryl substituted benzoic acids as rorgammat inhibitors and uses thereof |
| US10344000B2 (en) | 2015-10-27 | 2019-07-09 | Merck Sharp & Dohme Corp. | Substituted bicyclic pyrazole compounds as RORgammaT inhibitors and uses thereof |
| JP2018535958A (ja) | 2015-10-27 | 2018-12-06 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | ＲＯＲγＴ阻害薬としての置換インダゾール化合物及びその使用 |
| IL287136B2 (en) | 2016-02-05 | 2023-09-01 | Denali Therapeutics Inc | Receptor inhibitors - interacting with protein kinase 1 |
| CN106243045A (zh) * | 2016-07-27 | 2016-12-21 | 常州大学 | 一种2,5‑二甲氧基‑4‑氨基嘧啶的制备方法 |
| JOP20190053A1 (ar) | 2016-09-23 | 2019-03-21 | Novartis Ag | مركبات أزا إندازول للاستخدام في إصابات الأوتار و/ أو الرباط |
| AU2017359023B2 (en) | 2016-11-08 | 2021-12-09 | Bristol-Myers Squibb Company | 3-substituted propionic acids as alpha v integrin inhibitors |
| JP7208137B2 (ja) | 2016-12-09 | 2023-01-18 | デナリ セラピューティクス インコーポレイテッド | 化合物、組成物および方法 |
| US9969768B1 (en) | 2017-11-16 | 2018-05-15 | King Saud University | Oleanolic acid methyl ester derivatives |
| GB201817047D0 (en) | 2018-10-19 | 2018-12-05 | Heptares Therapeutics Ltd | H4 antagonist compounds |
| GB202019667D0 (en) * | 2020-12-14 | 2021-01-27 | Heptares Therapeutics Ltd | H4 antagonist comnpounds |
| CN116354937B (zh) * | 2021-12-27 | 2025-07-11 | 江苏恩华药业股份有限公司 | 吡啶(嘧啶)胺类衍生物及其应用 |
| TW202334164A (zh) | 2022-01-12 | 2023-09-01 | 美商戴納立製藥公司 | （Ｓ）－５－苄基－Ｎ－（５－甲基－４－側氧基－２，３，４，５－四氫吡啶並［３，２－ｂ］［１，４］氧氮呯－３－基）－４Ｈ－１，２，４－三唑－３－甲醯胺的晶型 |
| CN117362286B (zh) * | 2023-12-08 | 2024-03-12 | 清华大学 | 具有sirt6激动活性的化合物及其用途 |
Family Cites Families (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1108698B (de) | 1959-09-03 | 1961-06-15 | Hoechst Ag | Verfahren zur Herstellung von 2-(2'-Aminoaryl)-4, 5-arylen-1, 2, 3-triazolen |
| ATE437876T1 (de) * | 2003-06-20 | 2009-08-15 | Hoffmann La Roche | Hexahydropyridoisochinoline als dpp-iv- inhibitoren |
| WO2006058088A2 (en) * | 2004-11-23 | 2006-06-01 | Ptc Therapeutics, Inc. | Carbazole, carboline and indole derivatives useful in the inhibition of vegf production |
| EP1856099A2 (en) * | 2005-03-03 | 2007-11-21 | Sirtris Pharmaceuticals, Inc. | Acridine and quinoline derivatives as sirtuin modulators |
| EP1853610A1 (en) | 2005-03-03 | 2007-11-14 | Sirtris Pharmaceuticals, Inc. | N-phenyl benzamide derivatives as sirtuin modulators |
| WO2006094210A2 (en) * | 2005-03-03 | 2006-09-08 | Sirtris Pharmaceuticals, Inc. | Tetrahydroquinoxalinone sirtuin modulators |
| WO2006094246A2 (en) | 2005-03-03 | 2006-09-08 | Sirtris Pharmaceuticals, Inc. | N-arylmethyl benzamide sirtuin modulators |
| ATE544071T1 (de) | 2005-03-03 | 2012-02-15 | Sirtris Pharmaceuticals Inc | Fluoreszenzpolarisationstests für die acetyltransferase-deacetylase-aktivität |
| WO2006094248A1 (en) | 2005-03-03 | 2006-09-08 | Sirtris Pharmaceuticals, Inc. | Aryl-substituted cyclic sirtuin modulators |
| WO2006094235A1 (en) * | 2005-03-03 | 2006-09-08 | Sirtris Pharmaceuticals, Inc. | Fused heterocyclic compounds and their use as sirtuin modulators |
| WO2006094233A1 (en) | 2005-03-03 | 2006-09-08 | Sirtris Pharmaceuticals, Inc. | N,n'-dicyclic isothiourea sirtuin modulators |
| US20070014833A1 (en) | 2005-03-30 | 2007-01-18 | Sirtris Pharmaceuticals, Inc. | Treatment of eye disorders with sirtuin modulators |
| EP2805719A1 (en) | 2005-03-30 | 2014-11-26 | Glaxosmithkline LLC | Nicotinamide riboside and analogues thereof |
| CA2609549A1 (en) | 2005-05-25 | 2006-11-30 | Sirtris Pharmaceuticals, Inc. | Treatment of eye disorders with sirtuin modulators |
| DE102005026762A1 (de) * | 2005-06-09 | 2006-12-21 | Sanofi-Aventis Deutschland Gmbh | Azolopyridin-2-on-derivate als Inhibitoren von Lipasen und Phospholipasen |
| EP1898897A2 (en) | 2005-07-07 | 2008-03-19 | Sirtris Pharmaceuticals, Inc. | Methods and related compositions for treating or preventing obesity, insulin resistance disorders, and mitochondrial-associated disorders |
| US8088928B2 (en) | 2005-08-04 | 2012-01-03 | Sirtris Pharmaceuticals, Inc. | Sirtuin modulating compounds |
| US7855289B2 (en) | 2005-08-04 | 2010-12-21 | Sirtris Pharmaceuticals, Inc. | Sirtuin modulating compounds |
| DK1910384T3 (da) | 2005-08-04 | 2012-12-17 | Sirtris Pharmaceuticals Inc | Imidazo [2,1-b] thiazol-derivater som sirtuinmodulerende forbindelser |
| US8093401B2 (en) | 2005-08-04 | 2012-01-10 | Sirtris Pharmaceuticals, Inc. | Sirtuin modulating compounds |
| AU2006339607A1 (en) | 2005-12-02 | 2007-09-13 | Sirtris Pharmaceuticals, Inc. | Modulators of Cdc2-like kinases (Clks) and methods of use thereof |
| EP1955077B1 (en) | 2005-12-02 | 2012-06-13 | Sirtris Pharmaceuticals, Inc. | Mass spectrometry assays for acetyltransferase/deacetylase activity |
| DE102006014685A1 (de) * | 2006-03-28 | 2007-10-04 | Sanofi-Aventis | Imidazo-pyridin-2-on-derivate als Inhibitoren von Lipasen und Phospholiphasen |
| WO2008027379A2 (en) | 2006-08-29 | 2008-03-06 | Sirtris Pharmaceuticals, Inc. | Indicators of sirtuin activity and methods of use thereof |
| WO2008060400A2 (en) | 2006-11-15 | 2008-05-22 | Sirtris Pharmaceuticals, Inc. | Sirtuin polymorphisms and methods of use thereof |
| WO2008073451A2 (en) | 2006-12-11 | 2008-06-19 | Sirtris Pharmaceuticals, Inc. | Benzoimidazole derivatives as sirtuin (sir) modulating compounds |
| US20080249130A1 (en) | 2007-02-09 | 2008-10-09 | Sirtris Pharmaceuticals, Inc. | Gut microsomal triglyceride transport protein inhibitors |
| WO2008100376A2 (en) | 2007-02-15 | 2008-08-21 | Sirtris Pharmaceuticals, Inc. | Truncation variants of sirt1 and methods of use thereof |
| AU2008229385A1 (en) | 2007-03-19 | 2008-09-25 | Sirtris Pharmaceuticals, Inc. | Biomarkers of sirtuin activity and methods of use thereof |
| CL2008001822A1 (es) | 2007-06-20 | 2009-03-13 | Sirtris Pharmaceuticals Inc | Compuestos derivados de tiazolo[5,4-b]piridina; composicion farmaceutica que comprende a dichos compuestos; y uso del compuesto en el tratamiento de la resistencia a la insulina, sindrome metabolico, diabetes, entre otras. |
| TW200918542A (en) | 2007-06-20 | 2009-05-01 | Sirtris Pharmaceuticals Inc | Sirtuin modulating compounds |
| WO2009058348A1 (en) | 2007-11-01 | 2009-05-07 | Sirtris Pharmaceuticals, Inc. | Amide derivatives as sirtuin modulators |
| MX2010005186A (es) | 2007-11-08 | 2010-05-27 | Sirtris Pharmaceuticals Inc | Tiazolopiridinas solubilizadas. |
| WO2009085226A2 (en) | 2007-12-21 | 2009-07-09 | Sirtris Pharmaceuticals, Inc. | Inhibitors of cdc2-like kinases (clks) and methods of use thereof |
| WO2009089011A2 (en) | 2008-01-08 | 2009-07-16 | Sirtris Pharmaceuticals, Inc. | Resveratrol formulations |
| ES2586459T3 (es) | 2008-05-01 | 2016-10-14 | Glaxosmithkline Llc | Quinolinas y análogos relacionados como moduladores de sirtuina |
| US20110113498A1 (en) | 2008-05-15 | 2011-05-12 | Westphal Christoph H | Sirt1 polymorphic variants and methods of use thereof |
| WO2009146358A1 (en) | 2008-05-29 | 2009-12-03 | Sirtris Pharmaceuticals, Inc. | Imidazopyridine and related analogs as sirtuin modulators |
| CA2729128C (en) | 2008-07-03 | 2016-05-31 | Sirtris Pharmaceuticals, Inc. | Benzimidazoles and related analogs as sirtuin modulators |
| AU2009282076A1 (en) | 2008-08-12 | 2010-02-18 | Sirtris Pharmaceuticals, Inc. | Benzoxazoles, benzthiazoles and related analogs as sirtuin modulators |
| US20110172217A1 (en) * | 2008-09-05 | 2011-07-14 | Shionogi & Co., Ltd. | Ring-fused morpholine derivative having pi3k-inhibiting activity |
| MX2011003373A (es) | 2008-09-29 | 2011-06-09 | Sirtris Pharmaceuticals Inc | Quinazolinona, quinolona y analogos relacionados como moduladores de sirtuina. |
| RU2011121655A (ru) | 2008-10-29 | 2012-12-10 | Сертрис Фармасьютикалз, Инк. | Производные пиридина, бициклические производные пиридина и родственные аналоги в качестве модуляторов сиртуина |
| CA2743449C (en) | 2008-11-12 | 2016-10-18 | Ariad Pharmaceuticals, Inc. | Pyrazinopyrazines and derivatives as kinase inhibitors |
| EP2373645A4 (en) | 2008-12-08 | 2012-05-02 | Sirtris Pharmaceuticals Inc | ISOINDOLINONE AND RELATED ANALOGUES AS SIRTUIN MODULATORS |
| US20130190309A1 (en) | 2008-12-16 | 2013-07-25 | Chi B. Vu | Phthalazinone and related analogs as sirtuin modulators |
| BRPI0922435A2 (pt) | 2008-12-19 | 2018-09-11 | Sirtris Pharmaceuticals Inc | "composto de tiazolopiridina moduladores de sirtuina, composição farmacêutica compreendendo o mesmo e seu uso." |
| WO2010088574A1 (en) | 2009-01-30 | 2010-08-05 | Sirtris Pharmaceuticals, Inc. | Azabenzimidazoles and related analogs as sirtuin modulators |
| AU2010221417A1 (en) | 2009-03-02 | 2011-09-22 | Sirtris Pharmaceuticals, Inc. | 8-substituted quinolines and related analogs as sirtuin modulators |
| US8735406B2 (en) * | 2009-09-09 | 2014-05-27 | Dainippon Sumitomo Pharma Co., Ltd. | 8-oxodihydropurine derivative |
| WO2011116176A1 (en) | 2010-03-17 | 2011-09-22 | Sirtris Pharmaceuticals Inc. | 3-substitued imidazo (4, 5-b) pyridines and analogs as sirtuin modulators |
-
2010
- 2010-10-29 MX MX2012004995A patent/MX2012004995A/es not_active Application Discontinuation
- 2010-10-29 AU AU2010319842A patent/AU2010319842A1/en not_active Abandoned
- 2010-10-29 CN CN201080060180.2A patent/CN102725291B/zh not_active Expired - Fee Related
- 2010-10-29 US US13/504,134 patent/US9556201B2/en not_active Expired - Fee Related
- 2010-10-29 WO PCT/US2010/054880 patent/WO2011059839A1/en not_active Ceased
- 2010-10-29 JP JP2012537157A patent/JP2013509442A/ja not_active Ceased
- 2010-10-29 IN IN3799DEN2012 patent/IN2012DN03799A/en unknown
- 2010-10-29 CA CA2779303A patent/CA2779303A1/en not_active Abandoned
- 2010-10-29 KR KR1020127013635A patent/KR20120092141A/ko not_active Ceased
- 2010-10-29 BR BR112012010010A patent/BR112012010010A2/pt not_active IP Right Cessation
- 2010-10-29 ES ES10830519.4T patent/ES2574927T3/es active Active
- 2010-10-29 EP EP10830519.4A patent/EP2493888B1/en active Active
- 2010-10-29 RU RU2012122065/04A patent/RU2550821C2/ru not_active IP Right Cessation
-
2012
- 2012-04-23 IL IL219372A patent/IL219372A0/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2013509442A5 (https=) | ||
| JP2011519863A5 (https=) | ||
| RU2012122065A (ru) | Бициклические пиридины и аналоги в качестве модуляторов сиртуина | |
| RU2011121655A (ru) | Производные пиридина, бициклические производные пиридина и родственные аналоги в качестве модуляторов сиртуина | |
| JP2009535307A5 (https=) | ||
| JP2012523457A5 (https=) | ||
| JP2015503622A5 (https=) | ||
| JP2010504286A5 (https=) | ||
| JP2015511613A5 (https=) | ||
| RU2011117160A (ru) | Хиназолинон, хинолон и родственные аналоги в качестве модуляторов сиртутуина | |
| JP2018536648A5 (https=) | ||
| JP2012505871A5 (https=) | ||
| JP2015503621A5 (https=) | ||
| JP2009263394A5 (https=) | ||
| JP2006528621A5 (https=) | ||
| RU2008141239A (ru) | Соединения тетрагидропиридотиенопиримидина и способы их применения | |
| JP2011513305A5 (https=) | ||
| JP2012528166A5 (https=) | ||
| JP2011519854A5 (https=) | ||
| JP2013509392A5 (https=) | ||
| JP2009533323A5 (https=) | ||
| RU2014121390A (ru) | Новые дизамещенные соединения 3,4-диамино-3-циклобутен-1,2-диона для использования при лечении опосредованных цитокинами заболеваний | |
| EA201170099A1 (ru) | Замещенные пиримидин-4-оновые производные | |
| EA201071012A1 (ru) | Производные азетидинов, способ их получения и применение их в терапии | |
| JP2020517677A5 (https=) |