CA2540765A1 - Pyrimidin-2-amine derivatives and their use as a2b adenosine receptor antagonists - Google Patents
Pyrimidin-2-amine derivatives and their use as a2b adenosine receptor antagonists Download PDFInfo
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- CA2540765A1 CA2540765A1 CA002540765A CA2540765A CA2540765A1 CA 2540765 A1 CA2540765 A1 CA 2540765A1 CA 002540765 A CA002540765 A CA 002540765A CA 2540765 A CA2540765 A CA 2540765A CA 2540765 A1 CA2540765 A1 CA 2540765A1
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- 101150078577 Adora2b gene Proteins 0.000 title claims abstract description 8
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical class NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 title description 10
- 229940121359 adenosine receptor antagonist Drugs 0.000 title 1
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 50
- 230000008569 process Effects 0.000 claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 90
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 125000005843 halogen group Chemical group 0.000 claims description 35
- 125000004414 alkyl thio group Chemical group 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 125000004429 atom Chemical group 0.000 claims description 24
- 125000004122 cyclic group Chemical group 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000002950 monocyclic group Chemical group 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 15
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 14
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 14
- 125000004043 oxo group Chemical group O=* 0.000 claims description 11
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 10
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003367 polycyclic group Chemical group 0.000 claims description 9
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
- 230000001575 pathological effect Effects 0.000 claims description 7
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 7
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 6
- 150000001204 N-oxides Chemical class 0.000 claims description 6
- 230000008485 antagonism Effects 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 230000004054 inflammatory process Effects 0.000 claims description 6
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
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- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 5
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- YRPIMMMBNUUYLG-UHFFFAOYSA-N 4-(furan-2-yl)-n-pyridin-3-yl-5-pyrimidin-4-ylpyrimidin-2-amine Chemical compound N=1C=C(C=2N=CN=CC=2)C(C=2OC=CC=2)=NC=1NC1=CC=CN=C1 YRPIMMMBNUUYLG-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 206010006482 Bronchospasm Diseases 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 208000017442 Retinal disease Diseases 0.000 claims description 4
- 206010038923 Retinopathy Diseases 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
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- 239000003085 diluting agent Substances 0.000 claims description 4
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- MIWVUJKIMLESNF-UHFFFAOYSA-N 4-(furan-2-yl)-5-pyrimidin-4-yl-n-pyrimidin-5-ylpyrimidin-2-amine Chemical compound N=1C=C(C=2N=CN=CC=2)C(C=2OC=CC=2)=NC=1NC1=CN=CN=C1 MIWVUJKIMLESNF-UHFFFAOYSA-N 0.000 claims description 3
- LUMGKALEICFJJW-UHFFFAOYSA-N 4-(furan-2-yl)-n-(6-phenylmethoxypyridin-3-yl)-5-pyrimidin-4-ylpyrimidin-2-amine Chemical compound C=1C=CC=CC=1COC(N=C1)=CC=C1NC(N=C1C=2OC=CC=2)=NC=C1C1=CC=NC=N1 LUMGKALEICFJJW-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 206010063837 Reperfusion injury Diseases 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 208000035269 cancer or benign tumor Diseases 0.000 claims description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- WFZOKRYHKYUTCM-UHFFFAOYSA-N 4-(3-fluorophenyl)-5-(2-methylsulfanylpyrimidin-4-yl)-n-pyridin-3-ylpyrimidin-2-amine Chemical compound CSC1=NC=CC(C=2C(=NC(NC=3C=NC=CC=3)=NC=2)C=2C=C(F)C=CC=2)=N1 WFZOKRYHKYUTCM-UHFFFAOYSA-N 0.000 claims description 2
- GUSWWEXUJYDJDJ-UHFFFAOYSA-N 4-(3-fluorophenyl)-n-(6-methoxypyridin-3-yl)-5-pyrimidin-4-ylpyrimidin-2-amine Chemical compound C1=NC(OC)=CC=C1NC(N=C1C=2C=C(F)C=CC=2)=NC=C1C1=CC=NC=N1 GUSWWEXUJYDJDJ-UHFFFAOYSA-N 0.000 claims description 2
- IJJCFHWRLSIXBR-UHFFFAOYSA-N 4-(3-fluorophenyl)-n-pyridin-3-yl-5-pyrimidin-4-ylpyrimidin-2-amine Chemical compound FC1=CC=CC(C=2C(=CN=C(NC=3C=NC=CC=3)N=2)C=2N=CN=CC=2)=C1 IJJCFHWRLSIXBR-UHFFFAOYSA-N 0.000 claims description 2
- KYCNNTQTKVUZHE-UHFFFAOYSA-N 4-(furan-2-yl)-5-pyridazin-4-yl-n-pyridin-3-ylpyrimidin-2-amine Chemical compound N=1C=C(C=2C=NN=CC=2)C(C=2OC=CC=2)=NC=1NC1=CC=CN=C1 KYCNNTQTKVUZHE-UHFFFAOYSA-N 0.000 claims description 2
- HBOXINDAEXMPRC-UHFFFAOYSA-N 4-(furan-2-yl)-5-pyridazin-4-yl-n-pyrimidin-5-ylpyrimidin-2-amine Chemical compound N=1C=C(C=2C=NN=CC=2)C(C=2OC=CC=2)=NC=1NC1=CN=CN=C1 HBOXINDAEXMPRC-UHFFFAOYSA-N 0.000 claims description 2
- UOPAUGXJSSLKIS-UHFFFAOYSA-N 4-(furan-2-yl)-n-(1-oxidopyridin-1-ium-3-yl)-5-pyrimidin-4-ylpyrimidin-2-amine Chemical compound [O-][N+]1=CC=CC(NC=2N=C(C(C=3N=CN=CC=3)=CN=2)C=2OC=CC=2)=C1 UOPAUGXJSSLKIS-UHFFFAOYSA-N 0.000 claims description 2
- MTMQVOHUFMFSBV-UHFFFAOYSA-N 4-(furan-2-yl)-n-(1-oxidopyrimidin-1-ium-5-yl)-5-pyrimidin-4-ylpyrimidin-2-amine Chemical compound [O-][N+]1=CN=CC(NC=2N=C(C(C=3N=CN=CC=3)=CN=2)C=2OC=CC=2)=C1 MTMQVOHUFMFSBV-UHFFFAOYSA-N 0.000 claims description 2
- HCAGYEVTCRCKRK-UHFFFAOYSA-N 4-(furan-2-yl)-n-(2-methylsulfanylpyrimidin-4-yl)-5-pyrimidin-4-ylpyrimidin-2-amine Chemical compound CSC1=NC=CC(NC=2N=C(C(C=3N=CN=CC=3)=CN=2)C=2OC=CC=2)=N1 HCAGYEVTCRCKRK-UHFFFAOYSA-N 0.000 claims description 2
- RLKMGFNMHKPECM-UHFFFAOYSA-N 4-(furan-2-yl)-n-(4-methylpyridin-3-yl)-5-pyrimidin-4-ylpyrimidin-2-amine Chemical compound CC1=CC=NC=C1NC(N=C1C=2OC=CC=2)=NC=C1C1=CC=NC=N1 RLKMGFNMHKPECM-UHFFFAOYSA-N 0.000 claims description 2
- GOVNBNCQPRIZDI-UHFFFAOYSA-N 4-(furan-2-yl)-n-(5-methoxypyridin-3-yl)-5-pyrimidin-4-ylpyrimidin-2-amine Chemical compound COC1=CN=CC(NC=2N=C(C(C=3N=CN=CC=3)=CN=2)C=2OC=CC=2)=C1 GOVNBNCQPRIZDI-UHFFFAOYSA-N 0.000 claims description 2
- WKWSVUIWTBIOMU-UHFFFAOYSA-N 4-(furan-2-yl)-n-(6-methoxypyridin-3-yl)-5-(2-methylsulfanylpyrimidin-4-yl)pyrimidin-2-amine Chemical compound C1=NC(OC)=CC=C1NC(N=C1C=2OC=CC=2)=NC=C1C1=CC=NC(SC)=N1 WKWSVUIWTBIOMU-UHFFFAOYSA-N 0.000 claims description 2
- KFVNLZHVGOLGOY-UHFFFAOYSA-N 4-(furan-2-yl)-n-(6-methoxypyridin-3-yl)-5-pyrimidin-4-ylpyrimidin-2-amine Chemical compound C1=NC(OC)=CC=C1NC(N=C1C=2OC=CC=2)=NC=C1C1=CC=NC=N1 KFVNLZHVGOLGOY-UHFFFAOYSA-N 0.000 claims description 2
- UHVSXBIAKULVME-UHFFFAOYSA-N 4-(furan-2-yl)-n-(6-methylpyridin-3-yl)-5-pyrimidin-4-ylpyrimidin-2-amine Chemical compound C1=NC(C)=CC=C1NC(N=C1C=2OC=CC=2)=NC=C1C1=CC=NC=N1 UHVSXBIAKULVME-UHFFFAOYSA-N 0.000 claims description 2
- DLVGZMIEBGCZOC-UHFFFAOYSA-N 4-(furan-2-yl)-n-pyrazin-2-yl-5-pyrimidin-4-ylpyrimidin-2-amine Chemical compound N=1C=C(C=2N=CN=CC=2)C(C=2OC=CC=2)=NC=1NC1=CN=CC=N1 DLVGZMIEBGCZOC-UHFFFAOYSA-N 0.000 claims description 2
- SLTMSVGHUPIKFT-UHFFFAOYSA-N 4-(furan-2-yl)-n-pyridin-2-yl-5-pyrimidin-4-ylpyrimidin-2-amine Chemical compound N=1C=C(C=2N=CN=CC=2)C(C=2OC=CC=2)=NC=1NC1=CC=CC=N1 SLTMSVGHUPIKFT-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ESP200302275 | 2003-10-02 | ||
| ES200302275A ES2229928B1 (es) | 2003-10-02 | 2003-10-02 | Nuevos derivados de pirimidin-2-amina. |
| PCT/EP2004/010644 WO2005040155A1 (en) | 2003-10-02 | 2004-09-22 | Pyrimidin-2-amine derivates and their use as a2b adenosine receptor antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2540765A1 true CA2540765A1 (en) | 2005-05-06 |
Family
ID=34507890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002540765A Abandoned CA2540765A1 (en) | 2003-10-02 | 2004-09-22 | Pyrimidin-2-amine derivatives and their use as a2b adenosine receptor antagonists |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US20070265273A1 (enExample) |
| EP (1) | EP1668000A1 (enExample) |
| JP (1) | JP2007507443A (enExample) |
| KR (1) | KR20060097010A (enExample) |
| CN (1) | CN1886402A (enExample) |
| AR (1) | AR046170A1 (enExample) |
| AU (1) | AU2004283800B8 (enExample) |
| BR (1) | BRPI0415324A (enExample) |
| CA (1) | CA2540765A1 (enExample) |
| CO (1) | CO5690593A2 (enExample) |
| EC (1) | ECSP066426A (enExample) |
| ES (1) | ES2229928B1 (enExample) |
| IL (1) | IL174771A0 (enExample) |
| MX (1) | MXPA06003525A (enExample) |
| NO (1) | NO20061952L (enExample) |
| NZ (1) | NZ546266A (enExample) |
| PE (1) | PE20050473A1 (enExample) |
| RU (1) | RU2006114746A (enExample) |
| SG (1) | SG149077A1 (enExample) |
| TW (1) | TW200526645A (enExample) |
| UA (1) | UA82563C2 (enExample) |
| UY (1) | UY28529A1 (enExample) |
| WO (1) | WO2005040155A1 (enExample) |
| ZA (1) | ZA200602139B (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2391103C2 (ru) | 2004-10-15 | 2010-06-10 | Си Ви Терапьютикс, Инк. | Способ предупреждения и лечения ремоделирования дыхательных путей и воспаления легких с применением антагонистов аденозиновых рецепторов a2b |
| ES2270715B1 (es) * | 2005-07-29 | 2008-04-01 | Laboratorios Almirall S.A. | Nuevos derivados de pirazina. |
| ES2274712B1 (es) | 2005-10-06 | 2008-03-01 | Laboratorios Almirall S.A. | Nuevos derivados imidazopiridina. |
| DE102006046410A1 (de) * | 2006-09-20 | 2008-03-27 | Eberhard-Karls-Universität Tübingen Universitätsklinikum | Arzneimittel zur Prophylaxe oder Behandlung oder Diagnostik von ischämischen Krankheiten |
| 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. |
| RU2471793C2 (ru) * | 2007-06-08 | 2013-01-10 | Байер Кропсайенс Аг | Фунгицид на основе гетероциклил-пиримидинил-аминопроизводных |
| BRPI0813629A2 (pt) * | 2007-07-26 | 2018-07-10 | Novartis Ag | derivados de pirimidina úteis no tratamento de condições inflamatórias ou alérgicas |
| WO2009026276A1 (en) | 2007-08-22 | 2009-02-26 | Irm Llc | 5- (4- (haloalkoxy) phenyl) pyrimidine-2-amine compounds and compositions as kinase inhibitors |
| WO2009026204A1 (en) * | 2007-08-22 | 2009-02-26 | Irm Llc | 2-heteroarylamino-pyrimidine derivatives as kinase inhibitors |
| 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 |
| 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 |
| EP2308866A1 (de) | 2009-10-09 | 2011-04-13 | Bayer CropScience AG | Phenylpyri(mi)dinylpyrazole und ihre Verwendung als Fungizide |
| 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 |
| AR079545A1 (es) | 2009-12-21 | 2012-02-01 | Bayer Cropscience Ag | Tienilpiri(mi)dinilazol |
| SG183146A1 (en) * | 2010-02-05 | 2012-09-27 | Heptares Therapeutics Ltd | 1,2,4-triazine-4-amine derivatives |
| WO2012085815A1 (en) | 2010-12-21 | 2012-06-28 | Novartis Ag | Bi-heteroaryl compounds as vps34 inhibitors |
| JOP20210164A1 (ar) | 2019-01-11 | 2023-01-30 | Omeros Corp | طرق وتركيبات علاج السرطان |
| CN112625050B (zh) | 2019-07-30 | 2021-10-01 | 杭州阿诺生物医药科技有限公司 | 一种a2a和/或a2b受体抑制剂的制备方法 |
| CN112608316B (zh) | 2019-07-30 | 2022-10-21 | 厦门宝太生物科技股份有限公司 | 一种吡唑并三嗪类腺苷受体拮抗剂 |
| CN115477653B (zh) * | 2022-10-11 | 2024-04-09 | 安徽省庆云医药股份有限公司 | 一种曲拉西利关键中间体及曲拉西利的制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US176399A (en) * | 1876-04-18 | Improvement in boxes for packing crackers | ||
| US23763A (en) * | 1859-04-26 | Method of adjusting the knives of rotary cutter-heads for planing wood | ||
| US42891A (en) * | 1864-05-24 | Improvement in water-engines | ||
| US275038A (en) * | 1883-04-03 | Ors to themselves | ||
| US22106A (en) * | 1858-11-23 | Truss-bridge | ||
| GB9309573D0 (en) * | 1993-05-10 | 1993-06-23 | Merck Sharp & Dohme | Therapeutic agents |
| US5686470A (en) * | 1995-02-10 | 1997-11-11 | Weier; Richard M. | 2, 3-substituted pyridines for the treatment of inflammation |
| NZ521633A (en) * | 2000-04-26 | 2005-01-28 | Eisai Co Ltd | Use of an adenosine A2 or A2b recpetor antagonist for promoting bowel movement |
| US6641549B2 (en) * | 2001-02-05 | 2003-11-04 | Bsn Medical, Inc. | Custom-moldable support for patellar tendinitis |
| TWI330183B (enExample) * | 2001-10-22 | 2010-09-11 | Eisai R&D Man Co Ltd | |
| US20050043315A1 (en) * | 2002-01-02 | 2005-02-24 | Hideo Tsutsumi | Aminopyrimidine compounds, processes for their preparation and pharmaceutical compositions containing them |
-
2003
- 2003-10-02 ES ES200302275A patent/ES2229928B1/es not_active Expired - Fee Related
-
2004
- 2004-09-21 UY UY28529A patent/UY28529A1/es not_active Application Discontinuation
- 2004-09-22 SG SG200809684-4A patent/SG149077A1/en unknown
- 2004-09-22 RU RU2006114746/04A patent/RU2006114746A/ru not_active Application Discontinuation
- 2004-09-22 NZ NZ546266A patent/NZ546266A/en unknown
- 2004-09-22 US US10/574,101 patent/US20070265273A1/en not_active Abandoned
- 2004-09-22 ZA ZA200602139A patent/ZA200602139B/en unknown
- 2004-09-22 JP JP2006530007A patent/JP2007507443A/ja active Pending
- 2004-09-22 BR BRPI0415324-3A patent/BRPI0415324A/pt not_active IP Right Cessation
- 2004-09-22 WO PCT/EP2004/010644 patent/WO2005040155A1/en not_active Ceased
- 2004-09-22 CN CNA2004800346926A patent/CN1886402A/zh active Pending
- 2004-09-22 EP EP04765506A patent/EP1668000A1/en not_active Withdrawn
- 2004-09-22 CA CA002540765A patent/CA2540765A1/en not_active Abandoned
- 2004-09-22 KR KR1020067006384A patent/KR20060097010A/ko not_active Ceased
- 2004-09-22 UA UAA200604615A patent/UA82563C2/uk unknown
- 2004-09-22 MX MXPA06003525A patent/MXPA06003525A/es unknown
- 2004-09-22 AU AU2004283800A patent/AU2004283800B8/en not_active Ceased
- 2004-09-28 PE PE2004000948A patent/PE20050473A1/es not_active Application Discontinuation
- 2004-09-30 AR ARP040103547A patent/AR046170A1/es unknown
- 2004-09-30 TW TW093129574A patent/TW200526645A/zh unknown
-
2006
- 2006-03-16 EC EC2006006426A patent/ECSP066426A/es unknown
- 2006-03-31 CO CO06032147A patent/CO5690593A2/es not_active Application Discontinuation
- 2006-04-03 IL IL174771A patent/IL174771A0/en unknown
- 2006-05-02 NO NO20061952A patent/NO20061952L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2229928A1 (es) | 2005-04-16 |
| EP1668000A1 (en) | 2006-06-14 |
| IL174771A0 (en) | 2006-08-20 |
| NO20061952L (no) | 2006-06-26 |
| TW200526645A (en) | 2005-08-16 |
| US20070265273A1 (en) | 2007-11-15 |
| WO2005040155A1 (en) | 2005-05-06 |
| ZA200602139B (en) | 2007-06-27 |
| CO5690593A2 (es) | 2006-10-31 |
| AU2004283800B2 (en) | 2009-05-07 |
| SG149077A1 (en) | 2009-01-29 |
| NZ546266A (en) | 2008-10-31 |
| MXPA06003525A (es) | 2006-06-08 |
| ECSP066426A (es) | 2006-10-17 |
| JP2007507443A (ja) | 2007-03-29 |
| AU2004283800A1 (en) | 2005-05-06 |
| ES2229928B1 (es) | 2006-07-01 |
| AU2004283800B8 (en) | 2009-06-18 |
| PE20050473A1 (es) | 2005-08-24 |
| CN1886402A (zh) | 2006-12-27 |
| AR046170A1 (es) | 2005-11-30 |
| BRPI0415324A (pt) | 2006-12-05 |
| WO2005040155A8 (en) | 2006-04-20 |
| RU2006114746A (ru) | 2007-11-20 |
| UA82563C2 (uk) | 2008-04-25 |
| UY28529A1 (es) | 2005-04-29 |
| KR20060097010A (ko) | 2006-09-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |