ES2274712B1 - Nuevos derivados imidazopiridina. - Google Patents
Nuevos derivados imidazopiridina. Download PDFInfo
- Publication number
- ES2274712B1 ES2274712B1 ES200502433A ES200502433A ES2274712B1 ES 2274712 B1 ES2274712 B1 ES 2274712B1 ES 200502433 A ES200502433 A ES 200502433A ES 200502433 A ES200502433 A ES 200502433A ES 2274712 B1 ES2274712 B1 ES 2274712B1
- Authority
- ES
- Spain
- Prior art keywords
- pyridin
- imidazo
- fluoropyridin
- pyridine
- alkyl
- 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.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 110
- 238000011282 treatment Methods 0.000 claims abstract description 22
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims abstract description 12
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims abstract description 6
- 229960005305 adenosine Drugs 0.000 claims abstract description 6
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- 210000001035 gastrointestinal tract Anatomy 0.000 claims abstract description 4
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- 239000002464 receptor antagonist Substances 0.000 claims abstract description 4
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- -1 piperidinylmethyl Chemical group 0.000 claims description 54
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
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- YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 claims description 8
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
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- 230000001575 pathological effect Effects 0.000 claims description 6
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
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- MMAZBBTVGGVGIM-UHFFFAOYSA-N 6-(3-fluoropyridin-4-yl)-2-(4-methoxyphenyl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 MMAZBBTVGGVGIM-UHFFFAOYSA-N 0.000 claims description 4
- QCAGPDXBMNNMBH-UHFFFAOYSA-N 6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-2-pyridin-4-yl-1h-imidazo[4,5-b]pyridine Chemical compound FC1=CN=CC=C1C(C(=N1)C=2C=NC=CC=2)=CC2=C1NC(C=1C=CN=CC=1)=N2 QCAGPDXBMNNMBH-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- CMGXDPCRFRFEQJ-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-6-yl)-6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound FC1=CN=CC=C1C(C(=N1)C=2C=NC=CC=2)=CC2=C1NC(C=1C=C3OCCOC3=CC=1)=N2 CMGXDPCRFRFEQJ-UHFFFAOYSA-N 0.000 claims description 3
- LOUMZSUMBGYUSB-UHFFFAOYSA-N 2-(2,4-dichloro-5-fluorophenyl)-6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound C1=C(Cl)C(F)=CC(C=2NC3=NC(=C(C=4C(=CN=CC=4)F)C=C3N=2)C=2C=NC=CC=2)=C1Cl LOUMZSUMBGYUSB-UHFFFAOYSA-N 0.000 claims description 3
- KAZUSWOHYPVEKM-UHFFFAOYSA-N 2-(4-fluorophenyl)-6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(F)=CC=C1C1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 KAZUSWOHYPVEKM-UHFFFAOYSA-N 0.000 claims description 3
- WELTYXZXXJRVNV-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 WELTYXZXXJRVNV-UHFFFAOYSA-N 0.000 claims description 3
- JMNOPWJKGOGKSU-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)propan-2-yl]-6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound C=1C=C(Cl)C=CC=1C(C)(C)C(NC1=NC=2C=3C=NC=CC=3)=NC1=CC=2C1=CC=NC=C1F JMNOPWJKGOGKSU-UHFFFAOYSA-N 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- CUEWSJXBADPEGT-UHFFFAOYSA-N 4-[6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridin-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 CUEWSJXBADPEGT-UHFFFAOYSA-N 0.000 claims description 3
- MUUGCFKLOVKSDN-UHFFFAOYSA-N 5-(3-chloropyridin-4-yl)-2-(4-fluorophenyl)-6-(3-fluoropyridin-4-yl)-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(F)=CC=C1C1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C(=CN=CC=3)Cl)N=C2N1 MUUGCFKLOVKSDN-UHFFFAOYSA-N 0.000 claims description 3
- SLTIUZBNBDSTRB-UHFFFAOYSA-N 5-(3-chloropyridin-4-yl)-2-(4-fluorophenyl)-6-pyridin-4-yl-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(F)=CC=C1C1=NC2=CC(C=3C=CN=CC=3)=C(C=3C(=CN=CC=3)Cl)N=C2N1 SLTIUZBNBDSTRB-UHFFFAOYSA-N 0.000 claims description 3
- NVIMJSZNQGYNMM-UHFFFAOYSA-N 5-(3-chloropyridin-4-yl)-6-pyridin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound ClC1=CN=CC=C1C(C(=C1)C=2C=CN=CC=2)=NC2=C1NC(=O)N2 NVIMJSZNQGYNMM-UHFFFAOYSA-N 0.000 claims description 3
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- HEQZBTGQAYDCKB-UHFFFAOYSA-N 6-(3-chloropyridin-4-yl)-5-pyridin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound ClC1=CN=CC=C1C(C(=N1)C=2C=CN=CC=2)=CC2=C1NC(=O)N2 HEQZBTGQAYDCKB-UHFFFAOYSA-N 0.000 claims description 3
- CSPSBRHWRRLXMI-UHFFFAOYSA-N 6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-2-[4-(trifluoromethyl)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound FC1=CN=CC=C1C(C(=N1)C=2C=NC=CC=2)=CC2=C1NC(C=1C=CC(=CC=1)C(F)(F)F)=N2 CSPSBRHWRRLXMI-UHFFFAOYSA-N 0.000 claims description 3
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- ZQYYXKXTXVOABI-UHFFFAOYSA-N methyl 4-[6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 ZQYYXKXTXVOABI-UHFFFAOYSA-N 0.000 claims description 3
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
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- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- TWSMTGCRUGWDPG-UHFFFAOYSA-N tri(propan-2-yl)-(5-tributylstannyl-1,3-oxazol-2-yl)silane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CN=C([Si](C(C)C)(C(C)C)C(C)C)O1 TWSMTGCRUGWDPG-UHFFFAOYSA-N 0.000 description 1
- LHJCZOXMCGQVDQ-UHFFFAOYSA-N tri(propan-2-yl)silyl trifluoromethanesulfonate Chemical compound CC(C)[Si](C(C)C)(C(C)C)OS(=O)(=O)C(F)(F)F LHJCZOXMCGQVDQ-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
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- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- Obesity (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200502433A ES2274712B1 (es) | 2005-10-06 | 2005-10-06 | Nuevos derivados imidazopiridina. |
| UY29836A UY29836A1 (es) | 2005-10-06 | 2006-10-03 | Nuevos derivados imidazopiridina |
| PE2006001205A PE20070706A1 (es) | 2005-10-06 | 2006-10-04 | Nuevos derivados imidazopiridina como antagonistas de adenosina a2b |
| KR1020087008297A KR20080050475A (ko) | 2005-10-06 | 2006-10-05 | Ａ2ｂ 아데노신 수용체 안타고니스트로서의 이미다조피리딘유도체 |
| PCT/EP2006/009620 WO2007039297A1 (en) | 2005-10-06 | 2006-10-05 | Imidazopyridine derivatives as a2b adenosine receptor antagonists |
| US12/089,050 US7855202B2 (en) | 2005-10-06 | 2006-10-05 | Imidazopyridine derivatives as A2B adenosine receptor antagonists |
| CNA2006800371946A CN101326181A (zh) | 2005-10-06 | 2006-10-05 | 作为a2b腺苷受体的拮抗体的咪唑吡啶衍生物 |
| TW095137259A TW200800985A (en) | 2005-10-06 | 2006-10-05 | New imidazopyridine derivatives |
| RU2008117329/04A RU2008117329A (ru) | 2005-10-06 | 2006-10-05 | Производные имидазопиридина как антагонисты аденозинового рецептора а2в |
| AU2006299028A AU2006299028A1 (en) | 2005-10-06 | 2006-10-05 | Imidazopyridine derivatives as A2B adenosine receptor antagonists |
| CA002624879A CA2624879A1 (en) | 2005-10-06 | 2006-10-05 | Imidazopyridine derivatives as a2b adenosine receptor antagonists |
| JP2008533934A JP2009510152A (ja) | 2005-10-06 | 2006-10-05 | Ａ２ｂアデノシン受容体アンタゴニストとしての、イミダゾピリジン誘導体 |
| ARP060104379A AR055676A1 (es) | 2005-10-06 | 2006-10-05 | Derivados imidazopiridina |
| EP06806042A EP1931666A1 (en) | 2005-10-06 | 2006-10-05 | Imidazopyridine derivatives as a2b adenosine receptor antagonists |
| ZA200802588A ZA200802588B (en) | 2005-10-06 | 2008-03-20 | Imidazopyridine derivatives as A2B adenosine receptor antagonists |
| IL190336A IL190336A0 (en) | 2005-10-06 | 2008-03-20 | Imidazopyridine derivatives as a2b adenosine receptor antagonists |
| EC2008008343A ECSP088343A (es) | 2005-10-06 | 2008-04-03 | Nuevos derivados imidazopiridina |
| NO20082121A NO20082121L (no) | 2005-10-06 | 2008-05-06 | Imidazopyridinderivater som A2B-adenosinreseptorantagonister |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200502433A ES2274712B1 (es) | 2005-10-06 | 2005-10-06 | Nuevos derivados imidazopiridina. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2274712A1 ES2274712A1 (es) | 2007-05-16 |
| ES2274712B1 true ES2274712B1 (es) | 2008-03-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES200502433A Expired - Fee Related ES2274712B1 (es) | 2005-10-06 | 2005-10-06 | Nuevos derivados imidazopiridina. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7855202B2 (https=) |
| EP (1) | EP1931666A1 (https=) |
| JP (1) | JP2009510152A (https=) |
| KR (1) | KR20080050475A (https=) |
| CN (1) | CN101326181A (https=) |
| AR (1) | AR055676A1 (https=) |
| AU (1) | AU2006299028A1 (https=) |
| CA (1) | CA2624879A1 (https=) |
| EC (1) | ECSP088343A (https=) |
| ES (1) | ES2274712B1 (https=) |
| IL (1) | IL190336A0 (https=) |
| NO (1) | NO20082121L (https=) |
| PE (1) | PE20070706A1 (https=) |
| RU (1) | RU2008117329A (https=) |
| TW (1) | TW200800985A (https=) |
| UY (1) | UY29836A1 (https=) |
| WO (1) | WO2007039297A1 (https=) |
| ZA (1) | ZA200802588B (https=) |
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| ES2270715B1 (es) * | 2005-07-29 | 2008-04-01 | Laboratorios Almirall S.A. | Nuevos derivados de pirazina. |
| MX337906B (es) | 2006-10-19 | 2016-03-28 | Signal Pharm Llc | Compuestos de heteroarilo, composiciones de los mismos, y su uso como inhibidores de proteina cinasas. |
| ES2303776B1 (es) * | 2006-12-29 | 2009-08-07 | Laboratorios Almirall S.A. | Derivados de 5-fenil-6-piridin-4-il-1,3-dihidro-2h-imidazo(4,5-b)piridin-2-ona utiles como antagonistas del receptor de adenosina a2b. |
| ES2320955B1 (es) | 2007-03-02 | 2010-03-16 | Laboratorios Almirall S.A. | Nuevos derivados de 3-((1,2,4)triazolo(4,3-a)piridin-7-il)benzamida. |
| CA2684105C (en) | 2007-05-03 | 2011-09-06 | Pfizer Limited | Pyridine derivatives |
| AU2008343813B2 (en) * | 2007-12-19 | 2012-04-12 | Amgen Inc. | Inhibitors of PI3 kinase |
| EP2108641A1 (en) | 2008-04-11 | 2009-10-14 | Laboratorios Almirall, S.A. | New substituted spiro[cycloalkyl-1,3'-indo]-2'(1'H)-one derivatives and their use as p38 mitogen-activated kinase inhibitors |
| PT2294066E (pt) * | 2008-04-28 | 2014-11-21 | Janssen Pharmaceutica Nv | Benzoimidazoles como inibidores da prolil-hidroxilase |
| EP2113503A1 (en) | 2008-04-28 | 2009-11-04 | Laboratorios Almirall, S.A. | New substituted indolin-2-one derivatives and their use as p39 mitogen-activated kinase inhibitors |
| WO2010133534A1 (en) * | 2009-05-19 | 2010-11-25 | Cellzome Limited | Bicyclic amino substituted compounds as pi3k inhibitors |
| EP2322176A1 (en) | 2009-11-11 | 2011-05-18 | Almirall, S.A. | New 7-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one derivatives |
| US20120003329A1 (en) | 2010-06-30 | 2012-01-05 | Gilead Sciences, Inc. | Use of A2B Adenosine Receptor Antagonists for Treating Pulmonary Hypertension |
| WO2012033149A1 (ja) * | 2010-09-10 | 2012-03-15 | 塩野義製薬株式会社 | Ａｍｐｋ活性化作用を有するヘテロ環縮合イミダゾール誘導体 |
| AR085942A1 (es) | 2011-04-07 | 2013-11-06 | Gilead Sciences Inc | Uso de receptor de aadenosina para tratar la insuficiencia cardiaca y la arritmia en pacientes posinfarto de miocardio |
| CA2836487A1 (en) * | 2011-06-09 | 2012-12-13 | Rhizen Pharmaceuticals Sa | Novel compounds as modulators of gpr-119 |
| WO2013063221A1 (en) | 2011-10-25 | 2013-05-02 | Janssen Pharmaceutica Nv | Meglumine salt formulations of 1-(5,6-dichloro-1h-benzo[d]imidazol-2-yl)-1h-pyrazole-4-carboxylic acid |
| EA201400990A1 (ru) | 2012-04-06 | 2015-01-30 | Пфайзер Инк. | Ингибиторы диацилглицеринацилтрансферазы 2 |
| EP2861596B1 (en) * | 2012-06-19 | 2019-03-20 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
| WO2014145852A2 (en) * | 2013-03-15 | 2014-09-18 | Knopp Biosciences Llc | Imidazo(4,5-b) pyridin-2-yl amides as kv7 channel activators |
| US11175268B2 (en) | 2014-06-09 | 2021-11-16 | Biometry Inc. | Mini point of care gas chromatographic test strip and method to measure analytes |
| CN106537128B (zh) | 2014-06-09 | 2021-06-18 | 生物统计股份有限公司 | 用于测量分析物的低成本测试条和方法 |
| SMT202300362T1 (it) | 2014-09-12 | 2023-11-13 | Biohaven Therapeutics Ltd | Benzoimidazol-1,2-il-ammidi come attivatori di canale kv7 |
| ES2580702B1 (es) * | 2015-02-25 | 2017-06-08 | Palobiofarma, S.L. | Derivados de 2-aminopiridina como antagonistas del receptor A2b de adenosina y ligandos del receptor MT3 de melatonina |
| CN114859028A (zh) | 2016-07-19 | 2022-08-05 | 生物统计股份有限公司 | 使用批量可校准测试条测量分析物的方法和系统 |
| EP3562306B1 (en) | 2016-12-29 | 2025-02-26 | Ji Xing Pharmaceuticals Hong Kong Limited | Metalloenzyme inhibitor compounds |
| JP7227157B2 (ja) | 2016-12-29 | 2023-02-21 | フェーズバイオ ファーマシューティカルズ，インコーポレイテッド | 金属酵素阻害剤化合物 |
| JP6836693B2 (ja) | 2017-09-28 | 2021-03-03 | シーストーン・ファーマスーティカルズ・（スージョウ）・カンパニー・リミテッドＣｓｔｏｎｅ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ （Ｓｕｚｈｏｕ） Ｃｏ．， Ｌｔｄ． | Ａ２ａ受容体アンタゴニストとしての縮合環誘導体 |
| PT3792260T (pt) * | 2018-05-08 | 2024-10-02 | Nippon Shinyaku Co Ltd | Compostos de azabenzimidazol e produtos farmacêuticos |
| JP2022516969A (ja) | 2019-01-08 | 2022-03-03 | フェーズバイオ ファーマシューティカルズ，インコーポレイテッド | 金属酵素阻害剤化合物 |
| MX2021008094A (es) | 2019-01-11 | 2021-09-21 | Omeros Corp | Metodos y composiciones para el tratamiento del cancer. |
| CA3161582A1 (en) | 2019-11-13 | 2021-05-20 | Nippon Shinyaku Co., Ltd. | Azabenzimidazole compound and medicine |
| BR112022008457A2 (pt) * | 2019-11-13 | 2022-07-26 | Nippon Shinyaku Co Ltd | Agente terapêutico e agente profilático para distúrbios gastrointestinais funcionais e xerostomia |
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| GB9309573D0 (en) * | 1993-05-10 | 1993-06-23 | Merck Sharp & Dohme | Therapeutic agents |
| KR0151816B1 (ko) * | 1994-02-08 | 1998-10-15 | 강박광 | 신규의 치환된 피리딜 이미다졸 유도체 및 그의 제조방법 |
| US5686470A (en) * | 1995-02-10 | 1997-11-11 | Weier; Richard M. | 2, 3-substituted pyridines for the treatment of inflammation |
| US6096748A (en) | 1996-03-13 | 2000-08-01 | Smithkline Beecham Corporation | Pyrimidine compounds useful in treating cytokine mediated diseases |
| TW520362B (en) | 1996-12-05 | 2003-02-11 | Amgen Inc | Substituted pyrimidine compounds and pharmaceutical composition comprising same |
| IL136711A0 (en) | 1997-12-19 | 2001-06-14 | Amgen Inc | Substituted pyridine and pyridazine compounds and their pharmaceutical use |
| WO1999065897A1 (en) | 1998-06-19 | 1999-12-23 | Chiron Corporation | Inhibitors of glycogen synthase kinase 3 |
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- 2006-10-05 AR ARP060104379A patent/AR055676A1/es unknown
- 2006-10-05 RU RU2008117329/04A patent/RU2008117329A/ru not_active Application Discontinuation
- 2006-10-05 JP JP2008533934A patent/JP2009510152A/ja active Pending
- 2006-10-05 US US12/089,050 patent/US7855202B2/en not_active Expired - Fee Related
- 2006-10-05 EP EP06806042A patent/EP1931666A1/en not_active Withdrawn
- 2006-10-05 CN CNA2006800371946A patent/CN101326181A/zh active Pending
- 2006-10-05 TW TW095137259A patent/TW200800985A/zh unknown
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2008
- 2008-03-20 IL IL190336A patent/IL190336A0/en unknown
- 2008-03-20 ZA ZA200802588A patent/ZA200802588B/xx unknown
- 2008-04-03 EC EC2008008343A patent/ECSP088343A/es unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| TW200800985A (en) | 2008-01-01 |
| JP2009510152A (ja) | 2009-03-12 |
| AR055676A1 (es) | 2007-08-29 |
| NO20082121L (no) | 2008-07-07 |
| KR20080050475A (ko) | 2008-06-05 |
| ECSP088343A (es) | 2008-05-30 |
| ZA200802588B (en) | 2009-09-30 |
| US7855202B2 (en) | 2010-12-21 |
| CN101326181A (zh) | 2008-12-17 |
| UY29836A1 (es) | 2007-04-30 |
| EP1931666A1 (en) | 2008-06-18 |
| IL190336A0 (en) | 2009-09-22 |
| WO2007039297A1 (en) | 2007-04-12 |
| US20080275038A1 (en) | 2008-11-06 |
| PE20070706A1 (es) | 2007-09-24 |
| ES2274712A1 (es) | 2007-05-16 |
| RU2008117329A (ru) | 2009-11-20 |
| AU2006299028A1 (en) | 2007-04-12 |
| CA2624879A1 (en) | 2007-04-12 |
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