JP2008533082A5 - - Google Patents
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- Publication number
- JP2008533082A5 JP2008533082A5 JP2008501242A JP2008501242A JP2008533082A5 JP 2008533082 A5 JP2008533082 A5 JP 2008533082A5 JP 2008501242 A JP2008501242 A JP 2008501242A JP 2008501242 A JP2008501242 A JP 2008501242A JP 2008533082 A5 JP2008533082 A5 JP 2008533082A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- naphthyridine
- ylamino
- benzofuran
- dihydro
- 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
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 9
- 239000012453 solvate Substances 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- -1 (2,3-Dihydro-1-benzofuran-4-ylamino) -8-methyl-N 6 -[(2S) -tetrahydro-2-furanylmethyl] -1,7-naphthyridine-3,6-dicarboxamide tri Fluoroacetate Chemical compound 0.000 claims 2
- WMLSRQMNZCPXSD-YDALLXLXSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-6-n-[(2s)-1-methoxypropan-2-yl]-8-methyl-1,7-naphthyridine-3,6-dicarboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NC(=O)C1=CN=C2C(C)=NC(C(=O)N[C@@H](C)COC)=CC2=C1NC1=CC=CC2=C1CCO2 WMLSRQMNZCPXSD-YDALLXLXSA-N 0.000 claims 2
- ZYTHBUUTZVNQMF-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-6-(4-methylpiperazine-1-carbonyl)-1,7-naphthyridine-3-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CN(C)CCN1C(=O)C(N=C(C)C1=NC=C2C(N)=O)=CC1=C2NC1=CC=CC2=C1CCO2 ZYTHBUUTZVNQMF-UHFFFAOYSA-N 0.000 claims 2
- VESPFYNUUYIJSG-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-6-n-(2-methylsulfonylethyl)-1,7-naphthyridine-3,6-dicarboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NC(=O)C1=CN=C2C(C)=NC(C(=O)NCCS(C)(=O)=O)=CC2=C1NC1=CC=CC2=C1CCO2 VESPFYNUUYIJSG-UHFFFAOYSA-N 0.000 claims 2
- WCBQNDSQUDWMLB-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-6-n-(oxan-3-yl)-1,7-naphthyridine-3,6-dicarboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C2=C(NC=3C=4CCOC=4C=CC=3)C(C(N)=O)=CN=C2C(C)=NC=1C(=O)NC1CCCOC1 WCBQNDSQUDWMLB-UHFFFAOYSA-N 0.000 claims 2
- PQHVYRGOQRIFRY-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-6-n-(oxan-4-ylmethyl)-1,7-naphthyridine-3,6-dicarboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C2=C(NC=3C=4CCOC=4C=CC=3)C(C(N)=O)=CN=C2C(C)=NC=1C(=O)NCC1CCOCC1 PQHVYRGOQRIFRY-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- HEEMXKXXZIULOP-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-6-(2,6-dimethylmorpholine-4-carbonyl)-8-methyl-1,7-naphthyridine-3-carboxamide Chemical compound C1C(C)OC(C)CN1C(=O)C(N=C(C)C1=NC=C2C(N)=O)=CC1=C2NC1=CC=CC2=C1CCO2 HEEMXKXXZIULOP-UHFFFAOYSA-N 0.000 claims 1
- YISAICXITYETNB-XFULWGLBSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-6-[(3r)-3-(dimethylamino)pyrrolidine-1-carbonyl]-8-methyl-1,7-naphthyridine-3-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1[C@H](N(C)C)CCN1C(=O)C(N=C(C)C1=NC=C2C(N)=O)=CC1=C2NC1=CC=CC2=C1CCO2 YISAICXITYETNB-XFULWGLBSA-N 0.000 claims 1
- RJODAOXAHAZVAY-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-6-n,6-n,8-trimethyl-1,7-naphthyridine-3,6-dicarboxamide Chemical compound NC(=O)C1=CN=C2C(C)=NC(C(=O)N(C)C)=CC2=C1NC1=CC=CC2=C1CCO2 RJODAOXAHAZVAY-UHFFFAOYSA-N 0.000 claims 1
- PKQUNEBZMCQSBG-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-6-n,8-dimethyl-6-n-(1-methylpyrrolidin-3-yl)-1,7-naphthyridine-3,6-dicarboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C2=C(NC=3C=4CCOC=4C=CC=3)C(C(N)=O)=CN=C2C(C)=NC=1C(=O)N(C)C1CCN(C)C1 PKQUNEBZMCQSBG-UHFFFAOYSA-N 0.000 claims 1
- NWBHAJUSBHFUCV-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-6-n,8-dimethyl-6-n-(oxan-4-yl)-1,7-naphthyridine-3,6-dicarboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C2=C(NC=3C=4CCOC=4C=CC=3)C(C(N)=O)=CN=C2C(C)=NC=1C(=O)N(C)C1CCOCC1 NWBHAJUSBHFUCV-UHFFFAOYSA-N 0.000 claims 1
- RCLFVICEGJEFCV-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-6-n,8-dimethyl-6-n-propan-2-yl-1,7-naphthyridine-3,6-dicarboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NC(=O)C1=CN=C2C(C)=NC(C(=O)N(C)C(C)C)=CC2=C1NC1=CC=CC2=C1CCO2 RCLFVICEGJEFCV-UHFFFAOYSA-N 0.000 claims 1
- OYSRBXLSHFOWOO-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-6-n-(2-hydroxyethyl)-6-n,8-dimethyl-1,7-naphthyridine-3,6-dicarboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NC(=O)C1=CN=C2C(C)=NC(C(=O)N(CCO)C)=CC2=C1NC1=CC=CC2=C1CCO2 OYSRBXLSHFOWOO-UHFFFAOYSA-N 0.000 claims 1
- DKTSFUZIZPSSMC-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-6-n-(2-methoxyethyl)-6-n,8-dimethyl-1,7-naphthyridine-3,6-dicarboxamide Chemical compound NC(=O)C1=CN=C2C(C)=NC(C(=O)N(C)CCOC)=CC2=C1NC1=CC=CC2=C1CCO2 DKTSFUZIZPSSMC-UHFFFAOYSA-N 0.000 claims 1
- STFCAFIJJZGGMP-UTONKHPSSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-6-n-[(2r)-2-methoxypropyl]-8-methyl-1,7-naphthyridine-3,6-dicarboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NC(=O)C1=CN=C2C(C)=NC(C(=O)NC[C@@H](C)OC)=CC2=C1NC1=CC=CC2=C1CCO2 STFCAFIJJZGGMP-UTONKHPSSA-N 0.000 claims 1
- RQSFMEQSQSSUEU-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-6-n-[2-(dimethylamino)-2-oxoethyl]-8-methyl-1,7-naphthyridine-3,6-dicarboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NC(=O)C1=CN=C2C(C)=NC(C(=O)NCC(=O)N(C)C)=CC2=C1NC1=CC=CC2=C1CCO2 RQSFMEQSQSSUEU-UHFFFAOYSA-N 0.000 claims 1
- FLPXYJGAVYSLOJ-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-6-(2-methylmorpholine-4-carbonyl)-1,7-naphthyridine-3-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1COC(C)CN1C(=O)C(N=C(C)C1=NC=C2C(N)=O)=CC1=C2NC1=CC=CC2=C1CCO2 FLPXYJGAVYSLOJ-UHFFFAOYSA-N 0.000 claims 1
- WNNCNADAFDNJMI-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-6-(2-sulfamoylethyl)-5H-1,7-naphthyridine-3,6-dicarboxamide 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.NS(=O)(=O)CCC1(CC=2C(=C(C=NC2C(=N1)C)C(=O)N)NC1=CC=CC2=C1CCO2)C(=O)N WNNCNADAFDNJMI-UHFFFAOYSA-N 0.000 claims 1
- NOHNJQPELAOBOZ-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-6-(3-oxopiperazine-1-carbonyl)-1,7-naphthyridine-3-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C2=C(NC=3C=4CCOC=4C=CC=3)C(C(N)=O)=CN=C2C(C)=NC=1C(=O)N1CCNC(=O)C1 NOHNJQPELAOBOZ-UHFFFAOYSA-N 0.000 claims 1
- CGIHKJZDTZFEAI-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-6-(morpholine-4-carbonyl)-1,7-naphthyridine-3-carboxamide Chemical compound C=1C2=C(NC=3C=4CCOC=4C=CC=3)C(C(N)=O)=CN=C2C(C)=NC=1C(=O)N1CCOCC1 CGIHKJZDTZFEAI-UHFFFAOYSA-N 0.000 claims 1
- NTOCVHDSNDEPDI-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-6-(piperidine-1-carbonyl)-1,7-naphthyridine-3-carboxamide Chemical compound C=1C2=C(NC=3C=4CCOC=4C=CC=3)C(C(N)=O)=CN=C2C(C)=NC=1C(=O)N1CCCCC1 NTOCVHDSNDEPDI-UHFFFAOYSA-N 0.000 claims 1
- UWGDMKIHAJDDCE-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-6-(pyrrolidine-1-carbonyl)-1,7-naphthyridine-3-carboxamide Chemical compound C=1C2=C(NC=3C=4CCOC=4C=CC=3)C(C(N)=O)=CN=C2C(C)=NC=1C(=O)N1CCCC1 UWGDMKIHAJDDCE-UHFFFAOYSA-N 0.000 claims 1
- HMNOZIYVYNXEND-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-6-n-(1-methylpiperidin-4-yl)-1,7-naphthyridine-3,6-dicarboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CN(C)CCC1NC(=O)C(N=C(C)C1=NC=C2C(N)=O)=CC1=C2NC1=CC=CC2=C1CCO2 HMNOZIYVYNXEND-UHFFFAOYSA-N 0.000 claims 1
- VKTIHCZHPWHSME-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-6-n-(oxan-4-yl)-1,7-naphthyridine-3,6-dicarboxamide Chemical compound C=1C2=C(NC=3C=4CCOC=4C=CC=3)C(C(N)=O)=CN=C2C(C)=NC=1C(=O)NC1CCOCC1 VKTIHCZHPWHSME-UHFFFAOYSA-N 0.000 claims 1
- YSTCQHXFCCWEPP-UQKRIMTDSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-6-n-[[(2s)-oxolan-2-yl]methyl]-1,7-naphthyridine-3,6-dicarboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C2=C(NC=3C=4CCOC=4C=CC=3)C(C(N)=O)=CN=C2C(C)=NC=1C(=O)NC[C@@H]1CCCO1 YSTCQHXFCCWEPP-UQKRIMTDSA-N 0.000 claims 1
- ZBLBXQXSSPEADG-UHFFFAOYSA-N 6-cyclobutyl-4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-5H-1,7-naphthyridine-3,6-dicarboxamide 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.C1(CCC1)C1(CC=2C(=C(C=NC2C(=N1)C)C(=O)N)NC1=CC=CC2=C1CCO2)C(=O)N ZBLBXQXSSPEADG-UHFFFAOYSA-N 0.000 claims 1
- UZHZYSWBYDTYHH-UHFFFAOYSA-N 6-cyclopentyl-4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-5H-1,7-naphthyridine-3,6-dicarboxamide Chemical compound C1(CCCC1)C1(CC=2C(=C(C=NC2C(=N1)C)C(=O)N)NC1=CC=CC2=C1CCO2)C(=O)N UZHZYSWBYDTYHH-UHFFFAOYSA-N 0.000 claims 1
- GFYJSNURQLHVOR-UHFFFAOYSA-N FC(C(=O)O)(F)F.C1(CCCC1)CC1(CC=2C(=C(C=NC2C(=N1)C)C(=O)N)NC1=CC=CC2=C1CCO2)C(=O)N Chemical compound FC(C(=O)O)(F)F.C1(CCCC1)CC1(CC=2C(=C(C=NC2C(=N1)C)C(=O)N)NC1=CC=CC2=C1CCO2)C(=O)N GFYJSNURQLHVOR-UHFFFAOYSA-N 0.000 claims 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0505621.3A GB0505621D0 (en) | 2005-03-18 | 2005-03-18 | Novel compounds |
| PCT/EP2006/002543 WO2006097340A1 (en) | 2005-03-18 | 2006-03-16 | 1,7-naphthyridines as pde4 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008533082A JP2008533082A (ja) | 2008-08-21 |
| JP2008533082A5 true JP2008533082A5 (enExample) | 2008-12-11 |
Family
ID=34531502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008501242A Pending JP2008533082A (ja) | 2005-03-18 | 2006-03-16 | Ｐｄｅ４阻害剤としての１，７−ナフチリジン |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20080146563A1 (enExample) |
| EP (1) | EP1866305A1 (enExample) |
| JP (1) | JP2008533082A (enExample) |
| GB (1) | GB0505621D0 (enExample) |
| WO (1) | WO2006097340A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0425572D0 (en) * | 2004-11-19 | 2004-12-22 | Glaxo Group Ltd | 1,7-Naphthyridines |
| ES2433109T3 (es) | 2009-01-13 | 2013-12-09 | Glaxo Group Limited | Derivados de pirimidin-carboxamida como inhibidores de la Syk cinasa |
| NZ603332A (en) | 2010-04-02 | 2014-11-28 | Senomyx Inc | Sweet flavor modifier |
| MX336378B (es) | 2011-08-12 | 2016-01-15 | Senomyx Inc | Modificador del sabor dulce. |
| AU2015343463A1 (en) | 2014-11-07 | 2017-06-15 | Senomyx, Inc. | Substituted 4-amino-5-(cyclohexyloxy)quinoline-3-carboxylic acids as sweet flavor modifiers |
| EP4423074A4 (en) | 2021-10-28 | 2025-09-03 | Insilico Medicine Ip Ltd | PROLYL HYDROXYLASE DOMAIN-CONTAINING PROTEIN (PHD) INHIBITORS AND USES THEREOF |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0229281D0 (en) * | 2002-12-16 | 2003-01-22 | Novartis Ag | Organic compounds |
| TWI328009B (en) * | 2003-05-21 | 2010-08-01 | Glaxo Group Ltd | Quinoline derivatives as phosphodiesterase inhibitors |
| GB0425572D0 (en) * | 2004-11-19 | 2004-12-22 | Glaxo Group Ltd | 1,7-Naphthyridines |
-
2005
- 2005-03-18 GB GBGB0505621.3A patent/GB0505621D0/en not_active Ceased
-
2006
- 2006-03-16 EP EP06707615A patent/EP1866305A1/en not_active Withdrawn
- 2006-03-16 US US11/908,188 patent/US20080146563A1/en not_active Abandoned
- 2006-03-16 WO PCT/EP2006/002543 patent/WO2006097340A1/en not_active Ceased
- 2006-03-16 JP JP2008501242A patent/JP2008533082A/ja active Pending
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