ES2552643T3 - Pirrolopiridinas como inhibidores de cinasa - Google Patents
Pirrolopiridinas como inhibidores de cinasa Download PDFInfo
- Publication number
- ES2552643T3 ES2552643T3 ES09747404.3T ES09747404T ES2552643T3 ES 2552643 T3 ES2552643 T3 ES 2552643T3 ES 09747404 T ES09747404 T ES 09747404T ES 2552643 T3 ES2552643 T3 ES 2552643T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- phenyl
- hydrogen
- optionally substituted
- heterocyclic
- 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.)
- Active
Links
- 229940043355 kinase inhibitor Drugs 0.000 title 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
- 150000005255 pyrrolopyridines Chemical class 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 132
- -1 -SO2Ri Chemical group 0.000 abstract description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 51
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 43
- 229910052736 halogen Inorganic materials 0.000 abstract description 41
- 150000002367 halogens Chemical group 0.000 abstract description 41
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract description 40
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 29
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 29
- 239000001257 hydrogen Substances 0.000 abstract description 29
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract description 25
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract description 22
- 125000000217 alkyl group Chemical group 0.000 abstract description 22
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 19
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 16
- 125000004429 atom Chemical group 0.000 abstract description 14
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 abstract description 13
- 125000003118 aryl group Chemical group 0.000 abstract description 13
- 229920006395 saturated elastomer Polymers 0.000 abstract description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 8
- 125000002618 bicyclic heterocycle group Chemical group 0.000 abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 2
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 abstract description 2
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 49
- 238000005160 1H NMR spectroscopy Methods 0.000 description 41
- 125000004043 oxo group Chemical group O=* 0.000 description 40
- 230000014759 maintenance of location Effects 0.000 description 21
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 14
- MMWRGWQTAMNAFC-UHFFFAOYSA-N 1,2-dihydropyridine Chemical compound C1NC=CC=C1 MMWRGWQTAMNAFC-UHFFFAOYSA-N 0.000 description 12
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 12
- 150000002431 hydrogen Chemical class 0.000 description 10
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 8
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ZEFGUWRQFNTGGX-UHFFFAOYSA-N 1,6-dihydropyridazine Chemical compound C1NN=CC=C1 ZEFGUWRQFNTGGX-UHFFFAOYSA-N 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Chemical group 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
- 125000002757 morpholinyl group Chemical group 0.000 description 3
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- JBSLANHIBKBQGE-UHFFFAOYSA-N 2-cyclopropylacetamide Chemical compound NC(=O)CC1CC1 JBSLANHIBKBQGE-UHFFFAOYSA-N 0.000 description 1
- OAAKFAXUEYTMHF-UHFFFAOYSA-N 2-ethoxyacetamide Chemical compound CCOCC(N)=O OAAKFAXUEYTMHF-UHFFFAOYSA-N 0.000 description 1
- DRYMMXUBDRJPDS-UHFFFAOYSA-N 2-hydroxy-2-methylpropanamide Chemical compound CC(C)(O)C(N)=O DRYMMXUBDRJPDS-UHFFFAOYSA-N 0.000 description 1
- TZGPACAKMCUCKX-UHFFFAOYSA-N 2-hydroxyacetamide Chemical compound NC(=O)CO TZGPACAKMCUCKX-UHFFFAOYSA-N 0.000 description 1
- WOMBHFDZBLZRLM-UHFFFAOYSA-N 2-propan-2-yloxyacetamide Chemical compound CC(C)OCC(N)=O WOMBHFDZBLZRLM-UHFFFAOYSA-N 0.000 description 1
- OYBQCUZBVHFPBU-UHFFFAOYSA-N 5-methylpyrazine-2-carboxamide Chemical compound CC1=CN=C(C(N)=O)C=N1 OYBQCUZBVHFPBU-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 229940047889 isobutyramide Drugs 0.000 description 1
- QMZJNIBYRKNKLS-UHFFFAOYSA-N n-[4-(2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl)-5-bromo-1h-pyrrolo[2,3-b]pyridin-3-yl]pyridine-3-carboxamide Chemical compound C12=C(N3CC4NCCC4C3)C(Br)=CN=C2NC=C1NC(=O)C1=CC=CN=C1 QMZJNIBYRKNKLS-UHFFFAOYSA-N 0.000 description 1
- PKEACBQJQHBPIJ-LLVKDONJSA-N n-[4-[(3r)-3-aminopiperidin-1-yl]-5-bromo-1h-pyrrolo[2,3-b]pyridin-3-yl]-1-methylpyrazole-4-carboxamide Chemical compound C1=NN(C)C=C1C(=O)NC1=CNC2=NC=C(Br)C(N3C[C@H](N)CCC3)=C12 PKEACBQJQHBPIJ-LLVKDONJSA-N 0.000 description 1
- WCLCXCDIPAFMMJ-GFCCVEGCSA-N n-[4-[(3r)-3-aminopiperidin-1-yl]-5-ethylsulfanyl-1h-pyrrolo[2,3-b]pyridin-3-yl]cyclopropanecarboxamide Chemical compound C12=C(N3C[C@H](N)CCC3)C(SCC)=CN=C2NC=C1NC(=O)C1CC1 WCLCXCDIPAFMMJ-GFCCVEGCSA-N 0.000 description 1
- CTMQPNJRLWACHG-SNVBAGLBSA-N n-[4-[(3r)-3-aminopiperidin-1-yl]-5-fluoro-1h-pyrrolo[2,3-b]pyridin-3-yl]-2-methylpropanamide Chemical compound C=12C(NC(=O)C(C)C)=CNC2=NC=C(F)C=1N1CCC[C@@H](N)C1 CTMQPNJRLWACHG-SNVBAGLBSA-N 0.000 description 1
- MLSFOTDQXORALM-SNVBAGLBSA-N n-[4-[(3r)-3-aminopiperidin-1-yl]-5-fluoro-1h-pyrrolo[2,3-b]pyridin-3-yl]cyclopropanecarboxamide Chemical compound C1[C@H](N)CCCN1C1=C(F)C=NC2=C1C(NC(=O)C1CC1)=CN2 MLSFOTDQXORALM-SNVBAGLBSA-N 0.000 description 1
- RRYDBRRFZNMWLI-SECBINFHSA-N n-[4-[(3r)-3-aminopiperidin-1-yl]-5-fluoro-1h-pyrrolo[2,3-b]pyridin-3-yl]propanamide Chemical compound C=12C(NC(=O)CC)=CNC2=NC=C(F)C=1N1CCC[C@@H](N)C1 RRYDBRRFZNMWLI-SECBINFHSA-N 0.000 description 1
- ONQBAALYRROEEE-LLVKDONJSA-N n-[4-[(3r)-3-aminopiperidin-1-yl]-5-methylsulfanyl-1h-pyrrolo[2,3-b]pyridin-3-yl]-2-methylpropanamide Chemical compound CSC1=CN=C2NC=C(NC(=O)C(C)C)C2=C1N1CCC[C@@H](N)C1 ONQBAALYRROEEE-LLVKDONJSA-N 0.000 description 1
- XQRRDAPJHUPNLH-GFCCVEGCSA-N n-[4-[(3r)-3-aminopiperidin-1-yl]-5-propan-2-yl-1h-pyrrolo[2,3-b]pyridin-3-yl]propanamide Chemical compound C=12C(NC(=O)CC)=CNC2=NC=C(C(C)C)C=1N1CCC[C@@H](N)C1 XQRRDAPJHUPNLH-GFCCVEGCSA-N 0.000 description 1
- HHWOWSUWFHAWMC-SECBINFHSA-N n-[4-[(3r)-3-aminopyrrolidin-1-yl]-5-bromo-1h-pyrrolo[2,3-b]pyridin-3-yl]-2-methylpropanamide Chemical compound C=12C(NC(=O)C(C)C)=CNC2=NC=C(Br)C=1N1CC[C@@H](N)C1 HHWOWSUWFHAWMC-SECBINFHSA-N 0.000 description 1
- HHWOWSUWFHAWMC-VIFPVBQESA-N n-[4-[(3s)-3-aminopyrrolidin-1-yl]-5-bromo-1h-pyrrolo[2,3-b]pyridin-3-yl]-2-methylpropanamide Chemical compound C=12C(NC(=O)C(C)C)=CNC2=NC=C(Br)C=1N1CC[C@H](N)C1 HHWOWSUWFHAWMC-VIFPVBQESA-N 0.000 description 1
- HPBKTOHKWVMDLZ-GFCCVEGCSA-N n-[5-bromo-4-[(3r)-3-(ethylamino)piperidin-1-yl]-1h-pyrrolo[2,3-b]pyridin-3-yl]-2-methylpropanamide Chemical compound C1[C@H](NCC)CCCN1C1=C(Br)C=NC2=C1C(NC(=O)C(C)C)=CN2 HPBKTOHKWVMDLZ-GFCCVEGCSA-N 0.000 description 1
- OIONZBAXXSNKIQ-GFCCVEGCSA-N n-[5-bromo-4-[(3r)-3-(ethylamino)piperidin-1-yl]-1h-pyrrolo[2,3-b]pyridin-3-yl]cyclopropanecarboxamide Chemical compound C1[C@H](NCC)CCCN1C1=C(Br)C=NC2=C1C(NC(=O)C1CC1)=CN2 OIONZBAXXSNKIQ-GFCCVEGCSA-N 0.000 description 1
- RTHXWEICSABYQR-LLVKDONJSA-N n-[5-bromo-4-[(3r)-3-(methylamino)piperidin-1-yl]-1h-pyrrolo[2,3-b]pyridin-3-yl]-1-methyl-6-oxopyridazine-3-carboxamide Chemical compound C1[C@H](NC)CCCN1C1=C(Br)C=NC2=C1C(NC(=O)C1=NN(C)C(=O)C=C1)=CN2 RTHXWEICSABYQR-LLVKDONJSA-N 0.000 description 1
- ZHUHFIKLEHDPGW-LLVKDONJSA-N n-[5-bromo-4-[(3r)-3-(methylamino)piperidin-1-yl]-1h-pyrrolo[2,3-b]pyridin-3-yl]-2-ethoxyacetamide Chemical compound C=12C(NC(=O)COCC)=CNC2=NC=C(Br)C=1N1CCC[C@@H](NC)C1 ZHUHFIKLEHDPGW-LLVKDONJSA-N 0.000 description 1
- AYGXAXKQGVXYEP-GFCCVEGCSA-N n-[5-bromo-4-[(3r)-3-(methylamino)piperidin-1-yl]-1h-pyrrolo[2,3-b]pyridin-3-yl]-2-propan-2-yloxyacetamide Chemical compound C1[C@H](NC)CCCN1C1=C(Br)C=NC2=C1C(NC(=O)COC(C)C)=CN2 AYGXAXKQGVXYEP-GFCCVEGCSA-N 0.000 description 1
- FXKUNOKYNGPUSU-ZGTCLIOFSA-N n-[5-bromo-4-[(3r)-3-(methylamino)piperidin-1-yl]-1h-pyrrolo[2,3-b]pyridin-3-yl]-2-propan-2-yloxypropanamide Chemical compound C1[C@H](NC)CCCN1C1=C(Br)C=NC2=C1C(NC(=O)C(C)OC(C)C)=CN2 FXKUNOKYNGPUSU-ZGTCLIOFSA-N 0.000 description 1
- AENLUVVZDMVGIY-LLVKDONJSA-N n-[5-bromo-4-[(3r)-3-(methylamino)piperidin-1-yl]-1h-pyrrolo[2,3-b]pyridin-3-yl]-3-methoxypropanamide Chemical compound C1[C@H](NC)CCCN1C1=C(Br)C=NC2=C1C(NC(=O)CCOC)=CN2 AENLUVVZDMVGIY-LLVKDONJSA-N 0.000 description 1
- WBYHZIFOGFDQFB-LLVKDONJSA-N n-[5-bromo-4-[(3r)-3-(methylamino)piperidin-1-yl]-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidine-2-carboxamide Chemical compound C1[C@H](NC)CCCN1C1=C(Br)C=NC2=C1C(NC(=O)C=1N=CC=CN=1)=CN2 WBYHZIFOGFDQFB-LLVKDONJSA-N 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
- C07D401/02—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 two hetero rings
- C07D401/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Oncology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5292608P | 2008-05-13 | 2008-05-13 | |
| US52926P | 2008-05-13 | ||
| PCT/US2009/043691 WO2009140320A1 (en) | 2008-05-13 | 2009-05-13 | Pyrrolopyridines as kinase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2552643T3 true ES2552643T3 (es) | 2015-12-01 |
Family
ID=40810786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09747404.3T Active ES2552643T3 (es) | 2008-05-13 | 2009-05-13 | Pirrolopiridinas como inhibidores de cinasa |
Country Status (30)
| Country | Link |
|---|---|
| US (6) | US8178131B2 (enExample) |
| EP (2) | EP2307409B1 (enExample) |
| JP (2) | JP5703212B2 (enExample) |
| KR (2) | KR101643426B1 (enExample) |
| CN (3) | CN102089307B (enExample) |
| AR (1) | AR071717A1 (enExample) |
| AU (1) | AU2009246402B2 (enExample) |
| BR (1) | BRPI0913580B8 (enExample) |
| CA (1) | CA2724262C (enExample) |
| CL (1) | CL2009001152A1 (enExample) |
| CO (1) | CO6321244A2 (enExample) |
| CR (1) | CR11803A (enExample) |
| CY (1) | CY1116692T1 (enExample) |
| DK (1) | DK2307409T3 (enExample) |
| ES (1) | ES2552643T3 (enExample) |
| HK (1) | HK1219950A1 (enExample) |
| HR (1) | HRP20151018T1 (enExample) |
| HU (1) | HUE026160T2 (enExample) |
| IL (1) | IL209258A (enExample) |
| MX (1) | MX2010012449A (enExample) |
| NZ (1) | NZ589318A (enExample) |
| PH (1) | PH12013501779B1 (enExample) |
| PL (1) | PL2307409T3 (enExample) |
| PT (1) | PT2307409E (enExample) |
| RS (1) | RS54358B1 (enExample) |
| RU (1) | RU2517194C2 (enExample) |
| SI (1) | SI2307409T1 (enExample) |
| TW (2) | TWI554512B (enExample) |
| UA (1) | UA111933C2 (enExample) |
| WO (1) | WO2009140320A1 (enExample) |
Families Citing this family (40)
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