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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| GB0126511A GB0126511D0 (en) | 2001-11-05 | 2001-11-05 | Organic compounds |
| 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 |
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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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| EP2464649A1 (en) | 2009-08-12 | 2012-06-20 | Novartis AG | Heterocyclic hydrazone compounds and their uses to treat cancer and inflammation |
| ES2709108T3 (es) | 2009-08-17 | 2019-04-15 | Intellikine Llc | Compuestos heterocíclicos y usos de los mismos |
| BR112012008061A2 (pt) | 2009-08-20 | 2016-03-01 | Novartis Ag | compostos de oxima heterocíclica |
| EP2482798A1 (en) * | 2009-10-01 | 2012-08-08 | Alcon Research, Ltd. | Olopatadine compositions and uses thereof |
| CN102665715A (zh) | 2009-10-22 | 2012-09-12 | 沃泰克斯药物股份有限公司 | 治疗囊性纤维化和其他慢性疾病的组合物 |
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| WO2012034095A1 (en) | 2010-09-09 | 2012-03-15 | Irm Llc | Compounds and compositions as trk inhibitors |
| US8637516B2 (en) | 2010-09-09 | 2014-01-28 | Irm Llc | Compounds and compositions as TRK inhibitors |
| US8372845B2 (en) | 2010-09-17 | 2013-02-12 | Novartis Ag | Pyrazine derivatives as enac blockers |
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| AU2012220572A1 (en) | 2011-02-25 | 2013-08-29 | Irm Llc | Compounds and compositions as trk inhibitors |
| TW201311149A (zh) * | 2011-06-24 | 2013-03-16 | Ishihara Sangyo Kaisha | 有害生物防治劑 |
| UY34305A (es) | 2011-09-01 | 2013-04-30 | Novartis Ag | Derivados de heterociclos bicíclicos para el tratamiento de la hipertensión arterial pulmonar |
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| JP2015512425A (ja) | 2012-04-03 | 2015-04-27 | ノバルティス アーゲー | チロシンキナーゼ阻害剤との組合せ製品及びそれらの使用 |
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| KR20160141856A (ko) | 2014-04-24 | 2016-12-09 | 노파르티스 아게 | 포스파티딜이노시톨 3-키나제 억제제로서의 피라진 유도체 |
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| WO2016011658A1 (en) | 2014-07-25 | 2016-01-28 | Novartis Ag | Combination therapy |
| WO2016016822A1 (en) | 2014-07-31 | 2016-02-04 | Novartis Ag | Combination therapy |
| CN106795165B (zh) | 2014-08-06 | 2019-09-10 | 辉瑞公司 | 咪唑并哒嗪化合物 |
| GB201417002D0 (en) | 2014-09-26 | 2014-11-12 | Glaxosmithkline Ip Dev Ltd | Novel compound |
| GB201417094D0 (en) * | 2014-09-26 | 2014-11-12 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| CN106146491B (zh) * | 2015-03-27 | 2017-12-12 | 沈阳三生制药有限责任公司 | 被芳基或杂芳基取代的5‑羟基‑1,7‑萘啶化合物、其制备方法及其制药用途 |
| GB201604680D0 (en) | 2016-03-21 | 2016-05-04 | Glaxosmithkline Ip Dev Ltd | Chemical Compounds |
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| EP3980121A1 (en) | 2019-06-10 | 2022-04-13 | Novartis AG | Pyridine and pyrazine derivative for the treatment of cf, copd, and bronchiectasis |
| CN110339192A (zh) * | 2019-08-22 | 2019-10-18 | 吉林大学 | 一种掌叶防己碱用于治疗急性肺损伤的实验方法 |
| AU2020338971B2 (en) | 2019-08-28 | 2023-11-23 | Novartis Ag | Substituted 1,3-phenyl heteroaryl derivatives and their use in the treatment of disease |
| EP3805206A1 (en) * | 2019-10-08 | 2021-04-14 | Novaled GmbH | Compound and an organic semiconducting layer, an organic electronic device, a display device and a lighting device comprising the same |
| TW202140550A (zh) | 2020-01-29 | 2021-11-01 | 瑞士商諾華公司 | 使用抗ｔｓｌｐ抗體治療炎性或阻塞性氣道疾病之方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8800397D0 (en) * | 1988-01-08 | 1988-02-10 | Sandoz Ltd | Improvements in/relating to organic compounds |
| IE903911A1 (en) * | 1989-11-20 | 1991-05-22 | Ici Plc | Diazine derivatives |
| US5466697A (en) * | 1994-07-13 | 1995-11-14 | Syntex (U.S.A.) Inc. | 8-phenyl-1,6-naphthyridin-5-ones |
| RU2174123C2 (ru) * | 1996-10-28 | 2001-09-27 | Новартис Аг | Производные 8-арил-1,7-нафтиридина и фармацевтическая композиция, обладающая противовоспалительной активностью |
| GB9622386D0 (en) * | 1996-10-28 | 1997-01-08 | Sandoz Ltd | Organic compounds |
| WO1999018077A1 (en) | 1997-10-02 | 1999-04-15 | Eisai Co., Ltd. | Fused pyridine derivatives |
| JP2002114684A (ja) | 2000-10-03 | 2002-04-16 | Eisai Co Ltd | 尿路疾患治療剤 |
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