ES2300985T3 - Derivados de tiazol como antagonistas de a2b. - Google Patents
Derivados de tiazol como antagonistas de a2b. Download PDFInfo
- Publication number
- ES2300985T3 ES2300985T3 ES05706936T ES05706936T ES2300985T3 ES 2300985 T3 ES2300985 T3 ES 2300985T3 ES 05706936 T ES05706936 T ES 05706936T ES 05706936 T ES05706936 T ES 05706936T ES 2300985 T3 ES2300985 T3 ES 2300985T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- formula
- alkoxy
- hydrogen
- cyano
- 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 - Lifetime
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- 239000005557 antagonist Substances 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
- 239000001257 hydrogen Substances 0.000 claims abstract description 32
- 150000003839 salts Chemical group 0.000 claims abstract description 32
- -1 cyano, hydroxy Chemical group 0.000 claims abstract description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 30
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 21
- 150000002367 halogens Chemical class 0.000 claims abstract description 21
- 239000003814 drug Substances 0.000 claims abstract description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 8
- 125000002252 acyl group Chemical group 0.000 claims abstract description 7
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- 125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 7
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 25
- 150000002431 hydrogen Chemical group 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 229940079593 drug Drugs 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 230000000414 obstructive effect Effects 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
- 208000027866 inflammatory disease Diseases 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
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- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 6
- 230000000172 allergic effect Effects 0.000 claims description 5
- 208000010668 atopic eczema Diseases 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 239000000739 antihistaminic agent Substances 0.000 claims description 4
- 239000003434 antitussive agent Substances 0.000 claims description 4
- 229940124584 antitussives Drugs 0.000 claims description 4
- 230000004968 inflammatory condition Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- IDVMCNQJBJSULJ-UHFFFAOYSA-N 4-[[4-(3-cyanophenyl)-5-pyridazin-4-yl-1,3-thiazol-2-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC(C=2C=C(C=CC=2)C#N)=C(C=2C=NN=CC=2)S1 IDVMCNQJBJSULJ-UHFFFAOYSA-N 0.000 claims description 3
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
- 230000001387 anti-histamine Effects 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- LLASSJDALNWVNB-UHFFFAOYSA-N n-[4-(3-cyanophenyl)-5-pyrimidin-4-yl-1,3-thiazol-2-yl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2SC(=C(N=2)C=2C=C(C=CC=2)C#N)C=2N=CN=CC=2)=C1 LLASSJDALNWVNB-UHFFFAOYSA-N 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 2
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- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical group FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 230000002757 inflammatory effect Effects 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 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 description 8
- 238000004458 analytical method Methods 0.000 description 8
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- 238000010992 reflux Methods 0.000 description 7
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- 230000004913 activation Effects 0.000 description 6
- 229940124599 anti-inflammatory drug Drugs 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 210000003979 eosinophil Anatomy 0.000 description 6
- 210000002345 respiratory system Anatomy 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Chemical group 0.000 description 5
- 102000007470 Adenosine A2B Receptor Human genes 0.000 description 4
- 108010085273 Adenosine A2B receptor Proteins 0.000 description 4
- 101150078577 Adora2b gene Proteins 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 108060001084 Luciferase Proteins 0.000 description 4
- 239000005089 Luciferase Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 229960005305 adenosine Drugs 0.000 description 4
- 230000001363 autoimmune Effects 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 230000001404 mediated effect Effects 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
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- 229910052717 sulfur Chemical group 0.000 description 4
- 239000011593 sulfur Chemical group 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- BXFMDCDTWXMAAG-UHFFFAOYSA-N 3-(2-pyrimidin-4-ylacetyl)benzonitrile Chemical compound C=1C=CC(C#N)=CC=1C(=O)CC1=CC=NC=N1 BXFMDCDTWXMAAG-UHFFFAOYSA-N 0.000 description 3
- AIQPBPOXFJEVFR-UHFFFAOYSA-N 3-cyano-n-methoxy-n-methylbenzamide Chemical compound CON(C)C(=O)C1=CC=CC(C#N)=C1 AIQPBPOXFJEVFR-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 description 3
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- JADDQZYHOWSFJD-FLNNQWSLSA-N N-ethyl-5'-carboxamidoadenosine Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 JADDQZYHOWSFJD-FLNNQWSLSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- 229910052783 alkali metal Inorganic materials 0.000 description 3
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- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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|---|---|---|---|
| GB0401336 | 2004-01-21 | ||
| GBGB0401336.3A GB0401336D0 (en) | 2004-01-21 | 2004-01-21 | Organic compounds |
Publications (1)
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|---|---|
| ES2300985T3 true ES2300985T3 (es) | 2008-06-16 |
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| ES05706936T Expired - Lifetime ES2300985T3 (es) | 2004-01-21 | 2005-01-20 | Derivados de tiazol como antagonistas de a2b. |
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| EP (1) | EP1709036B1 (enExample) |
| JP (1) | JP2007518767A (enExample) |
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| AU (1) | AU2005206290B2 (enExample) |
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| ES (1) | ES2300985T3 (enExample) |
| GB (1) | GB0401336D0 (enExample) |
| PL (1) | PL1709036T3 (enExample) |
| PT (1) | PT1709036E (enExample) |
| RU (1) | RU2374242C2 (enExample) |
| WO (1) | WO2005070926A1 (enExample) |
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| ES2270715B1 (es) | 2005-07-29 | 2008-04-01 | Laboratorios Almirall S.A. | Nuevos derivados de pirazina. |
| NZ566036A (en) * | 2005-09-13 | 2010-06-25 | Janssen Pharmaceutica Nv | 2-Aniline-4-aryl substituted thiazole derivatives that modulate the alpha7 nicotinic receptor |
| ES2274712B1 (es) | 2005-10-06 | 2008-03-01 | Laboratorios Almirall S.A. | Nuevos derivados imidazopiridina. |
| WO2007109547A2 (en) | 2006-03-17 | 2007-09-27 | Cv Therapeutics, Inc. | Method of preventing and treating hepatic disease using a2b adenosine receptor antagonists |
| JP5026511B2 (ja) | 2006-05-18 | 2012-09-12 | エフ．ホフマン−ラ ロシュ アーゲー | アデノシンａ２ｂレセプターアンタゴニストとしてのチアゾロ−ピラミジン／ピリジン尿素誘導体 |
| JO2784B1 (en) | 2007-10-18 | 2014-03-15 | شركة جانسين فارماسوتيكا ان. في | 5,3,1 - Triazole substitute derivative |
| ES2424023T3 (es) | 2007-10-18 | 2013-09-26 | Janssen Pharmaceutica N.V. | 1,2,4-triazoles trisustituidos |
| MY152486A (en) | 2008-03-19 | 2014-10-15 | Janssen Pharmaceutica Nv | Trisubstituted 1,2,4 - triazoles as nicotinic acetylcholine receptor modulators |
| US8779158B2 (en) | 2008-05-09 | 2014-07-15 | Janssen Pharmaceutica Nv | Trisubstituted pyrazoles as acetylcholine receptor modulators |
| US9453002B2 (en) | 2013-08-16 | 2016-09-27 | Janssen Pharmaceutica Nv | Substituted imidazoles as N-type calcium channel blockers |
| 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 |
| CN109293652B (zh) * | 2017-07-24 | 2021-10-22 | 四川科伦博泰生物医药股份有限公司 | 一种取代的噻唑衍生物及其用途 |
| WO2019072143A1 (zh) * | 2017-10-11 | 2019-04-18 | 上海迪诺医药科技有限公司 | 4-氨基吡啶衍生物、其药物组合物、制备方法及应用 |
| WO2020083957A1 (en) | 2018-10-24 | 2020-04-30 | Leadxpro Ag | Functionalized aminotriazines |
| WO2020146795A1 (en) | 2019-01-11 | 2020-07-16 | Omeros Corporation | Methods and compositions for treating cancer |
| US20250101013A1 (en) * | 2022-01-19 | 2025-03-27 | Leadxpro Ag | Functionalized aminothiazoles |
| GB2615307A (en) * | 2022-01-28 | 2023-08-09 | Adorx Therapeutics Ltd | Antagonist compounds |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2677356B1 (fr) * | 1991-06-05 | 1995-03-17 | Sanofi Sa | Derives heterocycliques d'acylamino-2 thiazoles-5 substitues, leur preparation et compositions pharmaceutiques en contenant. |
| WO1999064418A1 (en) * | 1998-06-05 | 1999-12-16 | Novartis Ag | Aryl pyridinyl thiazoles |
| JP2000281685A (ja) * | 1999-01-28 | 2000-10-10 | Takeda Chem Ind Ltd | チアゾロピリミジン化合物、その製造法および用途 |
| WO2001030778A1 (en) * | 1999-10-27 | 2001-05-03 | Novartis Ag | Thiazole and imidazo [4,5-b] pyridine compounds and their pharmaceutical use |
| GB0028383D0 (en) * | 2000-11-21 | 2001-01-03 | Novartis Ag | Organic compounds |
| JP2002302445A (ja) * | 2001-02-02 | 2002-10-18 | Takeda Chem Ind Ltd | Ｊｎｋ阻害剤 |
| GB0123589D0 (en) * | 2001-10-01 | 2001-11-21 | Syngenta Participations Ag | Organic compounds |
| JP2005510508A (ja) * | 2001-11-08 | 2005-04-21 | 藤沢薬品工業株式会社 | アデノシンアンタゴニストとしてのチアゾールピリダジノン類 |
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2004
- 2004-01-21 GB GBGB0401336.3A patent/GB0401336D0/en not_active Ceased
-
2005
- 2005-01-20 ES ES05706936T patent/ES2300985T3/es not_active Expired - Lifetime
- 2005-01-20 BR BRPI0506927-0A patent/BRPI0506927A/pt not_active IP Right Cessation
- 2005-01-20 CA CA002553010A patent/CA2553010A1/en not_active Abandoned
- 2005-01-20 CN CN2005800026886A patent/CN1910178B/zh not_active Expired - Fee Related
- 2005-01-20 AT AT05706936T patent/ATE388147T1/de not_active IP Right Cessation
- 2005-01-20 RU RU2006130002/04A patent/RU2374242C2/ru not_active IP Right Cessation
- 2005-01-20 US US10/585,614 patent/US20090233938A1/en not_active Abandoned
- 2005-01-20 PT PT05706936T patent/PT1709036E/pt unknown
- 2005-01-20 DE DE602005005161T patent/DE602005005161T2/de not_active Expired - Lifetime
- 2005-01-20 AU AU2005206290A patent/AU2005206290B2/en not_active Ceased
- 2005-01-20 WO PCT/EP2005/000542 patent/WO2005070926A1/en not_active Ceased
- 2005-01-20 KR KR1020067014629A patent/KR20060129276A/ko not_active Ceased
- 2005-01-20 PL PL05706936T patent/PL1709036T3/pl unknown
- 2005-01-20 EP EP05706936A patent/EP1709036B1/en not_active Expired - Lifetime
- 2005-01-20 JP JP2006550041A patent/JP2007518767A/ja active Pending
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|---|---|
| US20090233938A1 (en) | 2009-09-17 |
| WO2005070926A1 (en) | 2005-08-04 |
| JP2007518767A (ja) | 2007-07-12 |
| CN1910178B (zh) | 2010-06-02 |
| RU2374242C2 (ru) | 2009-11-27 |
| PL1709036T3 (pl) | 2008-08-29 |
| EP1709036B1 (en) | 2008-03-05 |
| KR20060129276A (ko) | 2006-12-15 |
| PT1709036E (pt) | 2008-05-28 |
| ATE388147T1 (de) | 2008-03-15 |
| AU2005206290A1 (en) | 2005-08-04 |
| CA2553010A1 (en) | 2005-08-04 |
| GB0401336D0 (en) | 2004-02-25 |
| CN1910178A (zh) | 2007-02-07 |
| DE602005005161T2 (de) | 2009-03-19 |
| DE602005005161D1 (de) | 2008-04-17 |
| AU2005206290B2 (en) | 2008-12-04 |
| EP1709036A1 (en) | 2006-10-11 |
| BRPI0506927A (pt) | 2007-06-05 |
| RU2006130002A (ru) | 2008-02-27 |
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