NZ532586A - Naphthyridine derivatives, their preparation and their use as phosphodiesterase isoenzyme 4 (PDE4) inhibitors - Google Patents
Naphthyridine derivatives, their preparation and their use as phosphodiesterase isoenzyme 4 (PDE4) inhibitorsInfo
- Publication number
- NZ532586A NZ532586A NZ532586A NZ53258602A NZ532586A NZ 532586 A NZ532586 A NZ 532586A NZ 532586 A NZ532586 A NZ 532586A NZ 53258602 A NZ53258602 A NZ 53258602A NZ 532586 A NZ532586 A NZ 532586A
- Authority
- NZ
- New Zealand
- Prior art keywords
- phenyl
- compound
- formula
- naphthyridin
- carboxy
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 108010044467 Isoenzymes Proteins 0.000 title description 11
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 title description 7
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 title description 7
- 239000003112 inhibitor Substances 0.000 title description 6
- 150000005054 naphthyridines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 96
- 238000011282 treatment Methods 0.000 claims abstract description 47
- 150000003839 salts Chemical group 0.000 claims abstract description 41
- -1 carboxy, aminocarbonyl Chemical group 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 23
- 125000001424 substituent group Chemical group 0.000 claims abstract description 23
- 201000010099 disease Diseases 0.000 claims abstract description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
- 150000002367 halogens Chemical class 0.000 claims abstract description 16
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 16
- 239000003814 drug Substances 0.000 claims abstract description 15
- 230000005764 inhibitory process Effects 0.000 claims abstract description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 10
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- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims abstract description 9
- 230000008569 process Effects 0.000 claims abstract description 9
- 125000006413 ring segment Chemical group 0.000 claims abstract description 9
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000001404 mediated effect Effects 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 239000005864 Sulphur Substances 0.000 claims abstract description 3
- 230000003828 downregulation Effects 0.000 claims abstract description 3
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 3
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 claims abstract 2
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 claims abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 63
- 239000000203 mixture Substances 0.000 claims description 43
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 29
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- 229940093499 ethyl acetate Drugs 0.000 claims description 21
- 235000019439 ethyl acetate Nutrition 0.000 claims description 21
- 239000000243 solution Substances 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000010410 layer Substances 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 10
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 8
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- 239000012267 brine Substances 0.000 claims description 8
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 7
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 2
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 abstract 1
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Landscapes
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| GB0209882A GB0209882D0 (en) | 2002-04-30 | 2002-04-30 | Organic compounds |
| PCT/EP2002/012300 WO2003039544A1 (en) | 2001-11-05 | 2002-11-04 | Naphtyridine derivatives, their preparation and their use as phosphodiesterase isoenzyme 4 (pde4) inhibitors |
Publications (1)
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| NZ532586A true NZ532586A (en) | 2005-12-23 |
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| NZ532586A NZ532586A (en) | 2001-11-05 | 2002-11-04 | Naphthyridine derivatives, their preparation and their use as phosphodiesterase isoenzyme 4 (PDE4) inhibitors |
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| JP2010504933A (ja) | 2006-09-29 | 2010-02-18 | ノバルティス アーゲー | Ｐｉ３ｋ脂質キナーゼ阻害剤としてのピラゾロピリミジン |
| BRPI0718266A2 (pt) | 2006-10-30 | 2014-01-07 | Novartis Ag | Compostos heterocíclicos como agentes anti-inflamatórios. |
| AU2007342223B2 (en) | 2007-01-10 | 2011-02-24 | Irm Llc | Compounds and compositions as channel activating protease inhibitors |
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