NO329093B1 - Naftyridinderivater, deres fremstilling og deres anvendelse samt farmasoytisk sammensetning omfattende en slik forbindelse - Google Patents
Naftyridinderivater, deres fremstilling og deres anvendelse samt farmasoytisk sammensetning omfattende en slik forbindelse Download PDFInfo
- Publication number
- NO329093B1 NO329093B1 NO20042097A NO20042097A NO329093B1 NO 329093 B1 NO329093 B1 NO 329093B1 NO 20042097 A NO20042097 A NO 20042097A NO 20042097 A NO20042097 A NO 20042097A NO 329093 B1 NO329093 B1 NO 329093B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- alkoxy
- group
- compound according
- naphthyridin
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 82
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 150000005054 naphthyridines Chemical class 0.000 title 1
- 238000011282 treatment Methods 0.000 claims description 41
- 150000003839 salts Chemical group 0.000 claims description 36
- -1 4-[8-(5-fluoro-2-fluoro-2-methoxyphenyl)-[1,7]naphthyridin-6-yl]-cyclohexanecarboxylic acid Chemical compound 0.000 claims description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 18
- 230000002757 inflammatory effect Effects 0.000 claims description 14
- 230000005764 inhibitory process Effects 0.000 claims description 13
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 claims description 12
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 208000023504 respiratory system disease Diseases 0.000 claims description 12
- 230000000414 obstructive effect Effects 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 9
- 102100040247 Tumor necrosis factor Human genes 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- ZHLTXMKVCCTAHU-UHFFFAOYSA-N ethyl 4-[8-(3-cyanophenyl)-1,7-naphthyridin-6-yl]cyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OCC)CCC1C1=CC2=CC=CN=C2C(C=2C=C(C=CC=2)C#N)=N1 ZHLTXMKVCCTAHU-UHFFFAOYSA-N 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
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- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 230000003828 downregulation Effects 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
- JAZMOBNQGPEOPM-UHFFFAOYSA-N 4-[8-(3-carbamoylphenyl)-1,7-naphthyridin-6-yl]cyclohexane-1-carboxylic acid Chemical compound NC(=O)C1=CC=CC(C=2C3=NC=CC=C3C=C(N=2)C2CCC(CC2)C(O)=O)=C1 JAZMOBNQGPEOPM-UHFFFAOYSA-N 0.000 claims description 2
- TWWNJXWEOLLKJT-UHFFFAOYSA-N 4-[8-(3-cyanophenyl)-1,7-naphthyridin-6-yl]cyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1C1=CC2=CC=CN=C2C(C=2C=C(C=CC=2)C#N)=N1 TWWNJXWEOLLKJT-UHFFFAOYSA-N 0.000 claims description 2
- NBJPVPWHRDXZFE-UHFFFAOYSA-M potassium;4-[8-(3-cyanophenyl)-1,7-naphthyridin-6-yl]cyclohexane-1-carboxylate Chemical compound [K+].C1CC(C(=O)[O-])CCC1C1=CC2=CC=CN=C2C(C=2C=C(C=CC=2)C#N)=N1 NBJPVPWHRDXZFE-UHFFFAOYSA-M 0.000 claims description 2
- BZTUWDYLJHYCFI-UHFFFAOYSA-M sodium;4-[8-(5-fluoro-2-methoxyphenyl)-1,7-naphthyridin-6-yl]cyclohexane-1-carboxylate Chemical compound [Na+].COC1=CC=C(F)C=C1C1=NC(C2CCC(CC2)C([O-])=O)=CC2=CC=CN=C12 BZTUWDYLJHYCFI-UHFFFAOYSA-M 0.000 claims description 2
- DAKILIIJZBBNLO-UHFFFAOYSA-N 3-[6-(4-carboxycyclohexyl)-1,7-naphthyridin-8-yl]benzoic acid Chemical compound C1CC(C(=O)O)CCC1C1=CC2=CC=CN=C2C(C=2C=C(C=CC=2)C(O)=O)=N1 DAKILIIJZBBNLO-UHFFFAOYSA-N 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- GEBSAZQUXWFKCV-UHFFFAOYSA-N ethyl 4-[8-(5-fluoro-2-methoxyphenyl)-1,7-naphthyridin-6-yl]cyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OCC)CCC1C1=CC2=CC=CN=C2C(C=2C(=CC=C(F)C=2)OC)=N1 GEBSAZQUXWFKCV-UHFFFAOYSA-N 0.000 claims 1
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| GB0209882A GB0209882D0 (en) | 2002-04-30 | 2002-04-30 | Organic compounds |
| PCT/EP2002/012300 WO2003039544A1 (fr) | 2001-11-05 | 2002-11-04 | Derives de naphthyridine, preparation et utilisation en tant qu'inhibiteurs de l'iso-enzyme phosphodiesterase 4(pde4) |
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| CN105078978A (zh) | 2009-08-17 | 2015-11-25 | 因特利凯公司 | 杂环化合物及其用途 |
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| EP2813227A1 (fr) | 2009-10-22 | 2014-12-17 | Vertex Pharmaceuticals Incorporated | Compositions pour le traitement de la mucoviscidose et d'autres maladies chroniques |
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| WO2012034095A1 (fr) | 2010-09-09 | 2012-03-15 | Irm Llc | Composés et compositions comme inhibiteurs de trk |
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| JP5808826B2 (ja) | 2011-02-23 | 2015-11-10 | インテリカイン， エルエルシー | 複素環化合物およびその使用 |
| CA2828219A1 (fr) | 2011-02-25 | 2012-08-30 | Irm Llc | Composes et compositions en tant qu'inhibiteurs de trk |
| TW201311149A (zh) * | 2011-06-24 | 2013-03-16 | Ishihara Sangyo Kaisha | 有害生物防治劑 |
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| JP5886433B2 (ja) | 2011-09-16 | 2016-03-16 | ノバルティス アーゲー | 嚢胞性線維症処置のためのヘテロ環式化合物 |
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| EP2793893A4 (fr) | 2011-11-23 | 2015-07-08 | Intellikine Llc | Régimes de traitement améliorés utilisant des inhibiteurs de mtor |
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| CN103969300B (zh) * | 2013-01-24 | 2016-08-17 | 湖北大学 | 一种识别cgg三核苷酸重复序列的双功能电活性探针、探针的制备及试剂盒 |
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| CN105121439A (zh) | 2013-02-19 | 2015-12-02 | 辉瑞公司 | 作为pde4亚型抑制剂用于治疗cns和其他病症的氮杂苯并咪唑化合物 |
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| CA2895209C (fr) | 2013-03-14 | 2022-07-19 | Venkataiah Bollu | Composes de pyridine et de pyrazine substitues en tant qu'inhibiteurs de la pde4 |
| CN105246482A (zh) | 2013-03-15 | 2016-01-13 | 因特利凯有限责任公司 | 激酶抑制剂的组合及其用途 |
| GB201305668D0 (en) | 2013-03-28 | 2013-05-15 | Glaxosmithkline Ip Dev Ltd | Avs6 Integrin Antagonists |
| WO2015084804A1 (fr) | 2013-12-03 | 2015-06-11 | Novartis Ag | Combinaison d'un inhibiteur de mdm2 et d'un inhibiteur de braf, et leur utilisation |
| EA033571B1 (ru) | 2014-04-24 | 2019-11-06 | Novartis Ag | Производные пиразина в качестве ингибиторов фосфатидилинозитол 3-киназы |
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| EP3172210B1 (fr) | 2014-07-24 | 2020-01-15 | Pfizer Inc | Composés de pyrazolopyrimidine |
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| GB201417094D0 (en) | 2014-09-26 | 2014-11-12 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| GB201417002D0 (en) | 2014-09-26 | 2014-11-12 | Glaxosmithkline Ip Dev Ltd | Novel compound |
| 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 |
| MX2021007938A (es) | 2018-12-28 | 2022-01-24 | Regeneron Pharma | Tratamiento de trastornos respiratorios con inhibidores de la araquidonato 15-lipooxigenasa (alox15). |
| MX2021015133A (es) | 2019-06-10 | 2022-01-24 | Novartis Ag | Derivado de piridina y pirazina para el tratamiento de la fibrosis quistica, enfermedad pulmonar obstructiva cronica y bronquiectasia. |
| 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 |
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| IE903911A1 (en) * | 1989-11-20 | 1991-05-22 | Ici Plc | Diazine derivatives |
| GB9622386D0 (en) * | 1996-10-28 | 1997-01-08 | Sandoz Ltd | Organic compounds |
| EP1020445B1 (fr) | 1997-10-02 | 2008-08-13 | Eisai R&D Management Co., Ltd. | Derives de pyridine condenses |
| JP2002114684A (ja) | 2000-10-03 | 2002-04-16 | Eisai Co Ltd | 尿路疾患治療剤 |
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- 2002-11-04 RU RU2004117169/04A patent/RU2296764C2/ru not_active IP Right Cessation
- 2002-11-04 TW TW091132476A patent/TWI320784B/zh not_active IP Right Cessation
- 2002-11-04 AT AT02787554T patent/ATE349209T1/de active
- 2002-11-04 PL PL02368286A patent/PL368286A1/xx not_active Application Discontinuation
- 2002-11-04 CN CNB028214897A patent/CN1298324C/zh not_active Expired - Lifetime
- 2002-11-04 DK DK02787554T patent/DK1443925T3/da active
- 2002-11-04 DE DE60217160T patent/DE60217160T2/de not_active Expired - Lifetime
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2004
- 2004-04-01 IL IL161257A patent/IL161257A/en not_active IP Right Cessation
- 2004-05-21 NO NO20042097A patent/NO329093B1/no not_active IP Right Cessation
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2005
- 2005-01-20 HK HK05100545A patent/HK1069970A1/xx not_active IP Right Cessation
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2007
- 2007-03-06 CY CY20071100316T patent/CY1107532T1/el unknown
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