JP2009518340A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2009518340A5 JP2009518340A5 JP2008543727A JP2008543727A JP2009518340A5 JP 2009518340 A5 JP2009518340 A5 JP 2009518340A5 JP 2008543727 A JP2008543727 A JP 2008543727A JP 2008543727 A JP2008543727 A JP 2008543727A JP 2009518340 A5 JP2009518340 A5 JP 2009518340A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- phenyl
- unsubstituted
- naphthyl
- 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.)
- Pending
Links
- -1 phenoxy, naphthyloxy, phenyl Chemical group 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000003107 substituted aryl group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 2
- DKQXZNPFKWRKGG-UHFFFAOYSA-N n-[2-methyl-5-[[3-(trifluoromethyl)phenyl]carbamoyl]phenyl]pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C2=C3C=CC=CN3N=C2)C(C)=CC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 DKQXZNPFKWRKGG-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 19
- 125000005843 halogen group Chemical group 0.000 claims 18
- 125000001624 naphthyl group Chemical group 0.000 claims 18
- 201000010099 disease Diseases 0.000 claims 15
- 150000003839 salts Chemical group 0.000 claims 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- 102000001253 Protein Kinase Human genes 0.000 claims 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 7
- 108060006633 protein kinase Proteins 0.000 claims 7
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims 3
- 230000004770 neurodegeneration Effects 0.000 claims 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 3
- 230000008929 regeneration Effects 0.000 claims 3
- 238000011069 regeneration method Methods 0.000 claims 3
- 208000037803 restenosis Diseases 0.000 claims 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 2
- 102000050554 Eph Family Receptors Human genes 0.000 claims 2
- 108091008815 Eph receptors Proteins 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 2
- 108091000080 Phosphotransferase Proteins 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 2
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 208000025747 Rheumatic disease Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 206010020718 hyperplasia Diseases 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 claims 2
- 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 102000020233 phosphotransferase Human genes 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- 210000002307 prostate Anatomy 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 2
- 230000000552 rheumatic effect Effects 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- 150000003456 sulfonamides Chemical class 0.000 claims 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 claims 1
- NTDHZKMLYLHSHG-UHFFFAOYSA-N 6-(3-methoxyphenyl)-n-(2-methylphenyl)pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound COC1=CC=CC(C2=CN3N=CC(=C3C=C2)C(=O)NC=2C(=CC=CC=2)C)=C1 NTDHZKMLYLHSHG-UHFFFAOYSA-N 0.000 claims 1
- VOZRGVOHRTXRBW-UHFFFAOYSA-N 6-(4-methoxyphenyl)-n-(2-methylphenyl)pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CN2N=CC(C(=O)NC=3C(=CC=CC=3)C)=C2C=C1 VOZRGVOHRTXRBW-UHFFFAOYSA-N 0.000 claims 1
- FNLOOMKOQOZFEH-UHFFFAOYSA-N 6-(dimethylsulfamoyl)-n-[2-methyl-5-[[3-(trifluoromethyl)phenyl]carbamoyl]phenyl]pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C1=NN2C=C(S(=O)(=O)N(C)C)C=CC2=C1C(=O)NC(C(=CC=1)C)=CC=1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FNLOOMKOQOZFEH-UHFFFAOYSA-N 0.000 claims 1
- CUFXCXRHYOZGHC-UHFFFAOYSA-N 6-(dimethylsulfamoyl)-n-[5-[[4-methoxy-3-(trifluoromethyl)phenyl]carbamoyl]-2-methylphenyl]pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1NC(=O)C1=CC=C(C)C(NC(=O)C2=C3C=CC(=CN3N=C2)S(=O)(=O)N(C)C)=C1 CUFXCXRHYOZGHC-UHFFFAOYSA-N 0.000 claims 1
- WRIUDPIXTLSRHB-UHFFFAOYSA-N 6-[4-(dimethylamino)phenyl]-n-(2-methylphenyl)pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1C1=CN2N=CC(C(=O)NC=3C(=CC=CC=3)C)=C2C=C1 WRIUDPIXTLSRHB-UHFFFAOYSA-N 0.000 claims 1
- 102000029330 CSK Tyrosine-Protein Kinase Human genes 0.000 claims 1
- 108010069682 CSK Tyrosine-Protein Kinase Proteins 0.000 claims 1
- 101100381481 Caenorhabditis elegans baz-2 gene Proteins 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 201000009273 Endometriosis Diseases 0.000 claims 1
- 102100031968 Ephrin type-B receptor 2 Human genes 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 208000017604 Hodgkin disease Diseases 0.000 claims 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 1
- 206010021143 Hypoxia Diseases 0.000 claims 1
- 206010061216 Infarction Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000007766 Kaposi sarcoma Diseases 0.000 claims 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 206010056677 Nerve degeneration Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000031481 Pathologic Constriction Diseases 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- 108091008551 RET receptors Proteins 0.000 claims 1
- 101100372762 Rattus norvegicus Flt1 gene Proteins 0.000 claims 1
- 208000017442 Retinal disease Diseases 0.000 claims 1
- 206010038923 Retinopathy Diseases 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 206010039710 Scleroderma Diseases 0.000 claims 1
- 208000000102 Squamous Cell Carcinoma of Head and Neck Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 208000034841 Thrombotic Microangiopathies Diseases 0.000 claims 1
- 208000033781 Thyroid carcinoma Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 1
- 108091008605 VEGF receptors Proteins 0.000 claims 1
- 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 claims 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 210000004100 adrenal gland Anatomy 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 150000001408 amides Chemical group 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 238000002399 angioplasty Methods 0.000 claims 1
- 210000001367 artery Anatomy 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 210000003050 axon Anatomy 0.000 claims 1
- 125000004069 aziridinyl group Chemical group 0.000 claims 1
- 125000004045 azirinyl group Chemical group 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 1
- 230000033228 biological regulation Effects 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 210000004204 blood vessel Anatomy 0.000 claims 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 208000023819 chronic asthma Diseases 0.000 claims 1
- 208000037976 chronic inflammation Diseases 0.000 claims 1
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 208000019425 cirrhosis of liver Diseases 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 201000002758 colorectal adenoma Diseases 0.000 claims 1
- 208000033679 diabetic kidney disease Diseases 0.000 claims 1
- 238000003745 diagnosis Methods 0.000 claims 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims 1
- 125000005303 dithiazolyl group Chemical group S1SNC(=C1)* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 210000004696 endometrium Anatomy 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 201000000459 head and neck squamous cell carcinoma Diseases 0.000 claims 1
- 201000011066 hemangioma Diseases 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 230000007954 hypoxia Effects 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims 1
- 230000007574 infarction Effects 0.000 claims 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims 1
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
- 125000005956 isoquinolyl group Chemical group 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 230000003211 malignant effect Effects 0.000 claims 1
- 208000006178 malignant mesothelioma Diseases 0.000 claims 1
- 201000005282 malignant pleural mesothelioma Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 210000003584 mesangial cell Anatomy 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 210000002464 muscle smooth vascular Anatomy 0.000 claims 1
- GKKBOYULKXSRJE-UHFFFAOYSA-N n-(2-methylphenyl)-6-(4-morpholin-4-ylphenyl)pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound CC1=CC=CC=C1NC(=O)C1=C2C=CC(C=3C=CC(=CC=3)N3CCOCC3)=CN2N=C1 GKKBOYULKXSRJE-UHFFFAOYSA-N 0.000 claims 1
- GVSAVGKQNHLKIZ-UHFFFAOYSA-N n-[2-methyl-5-[[3-(trifluoromethyl)benzoyl]amino]phenyl]-6-phenylpyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C2=C3C=CC(=CN3N=C2)C=2C=CC=CC=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 GVSAVGKQNHLKIZ-UHFFFAOYSA-N 0.000 claims 1
- CANPPBQWQZNJME-UHFFFAOYSA-N n-[2-methyl-5-[[3-(trifluoromethyl)benzoyl]amino]phenyl]pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C2=C3C=CC=CN3N=C2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 CANPPBQWQZNJME-UHFFFAOYSA-N 0.000 claims 1
- LMNVSDJSGIAEQA-UHFFFAOYSA-N n-[2-methyl-5-[[3-(trifluoromethyl)phenyl]carbamoyl]phenyl]-6-phenylpyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound CC1=CC=C(C(=O)NC=2C=C(C=CC=2)C(F)(F)F)C=C1NC(=O)C(=C1C=C2)C=NN1C=C2C1=CC=CC=C1 LMNVSDJSGIAEQA-UHFFFAOYSA-N 0.000 claims 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 1
- 210000003739 neck Anatomy 0.000 claims 1
- 201000003142 neovascular glaucoma Diseases 0.000 claims 1
- 201000009925 nephrosclerosis Diseases 0.000 claims 1
- 210000005036 nerve Anatomy 0.000 claims 1
- 210000000944 nerve tissue Anatomy 0.000 claims 1
- 230000000626 neurodegenerative effect Effects 0.000 claims 1
- 210000002569 neuron Anatomy 0.000 claims 1
- 230000035771 neuroregeneration Effects 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 210000004798 organs belonging to the digestive system Anatomy 0.000 claims 1
- 210000001672 ovary Anatomy 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000000466 oxiranyl group Chemical group 0.000 claims 1
- 239000001301 oxygen Chemical group 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 125000005327 perimidinyl group Chemical group N1C(=NC2=CC=CC3=CC=CC1=C23)* 0.000 claims 1
- 210000001428 peripheral nervous system Anatomy 0.000 claims 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical class 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- 230000035755 proliferation Effects 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 210000000664 rectum Anatomy 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 230000011664 signaling Effects 0.000 claims 1
- 230000000392 somatic effect Effects 0.000 claims 1
- 208000020431 spinal cord injury Diseases 0.000 claims 1
- 230000036262 stenosis Effects 0.000 claims 1
- 208000037804 stenosis Diseases 0.000 claims 1
- 230000000638 stimulation Effects 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- PZWOKXJAEGKWLM-UHFFFAOYSA-N tert-butyl 4-[4-[3-[(2-methylphenyl)carbamoyl]pyrazolo[1,5-a]pyridin-6-yl]phenyl]piperazine-1-carboxylate Chemical compound CC1=CC=CC=C1NC(=O)C1=C2C=CC(C=3C=CC(=CC=3)N3CCN(CC3)C(=O)OC(C)(C)C)=CN2N=C1 PZWOKXJAEGKWLM-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000005505 thiomorpholino group Chemical group 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 208000013077 thyroid gland carcinoma Diseases 0.000 claims 1
- 208000037816 tissue injury Diseases 0.000 claims 1
- 230000009529 traumatic brain injury Effects 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 1
- 210000003932 urinary bladder Anatomy 0.000 claims 1
- 210000004291 uterus Anatomy 0.000 claims 1
- 210000001215 vagina Anatomy 0.000 claims 1
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- GRJIABFMPQBAKK-UHFFFAOYSA-N 3-amino-4-methyl-n-[3-(trifluoromethyl)phenyl]benzamide Chemical compound C1=C(N)C(C)=CC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 GRJIABFMPQBAKK-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- UFOJNUSJWKEEEQ-UHFFFAOYSA-N n-(3-amino-4-methylphenyl)-3-(trifluoromethyl)benzamide Chemical compound C1=C(N)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 UFOJNUSJWKEEEQ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0525065A GB0525065D0 (en) | 2005-12-08 | 2005-12-08 | Organic compounds |
| GB0600931A GB0600931D0 (en) | 2006-01-17 | 2006-01-17 | Organic compounds |
| PCT/EP2006/011722 WO2007065664A2 (en) | 2005-12-08 | 2006-12-06 | Pyrazolo[1,5-a]pyridine-3-carboxylic acids as ephb and vegfr2 kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009518340A JP2009518340A (ja) | 2009-05-07 |
| JP2009518340A5 true JP2009518340A5 (https=) | 2010-01-28 |
Family
ID=38007965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008543727A Pending JP2009518340A (ja) | 2005-12-08 | 2006-12-06 | ＥｐｈＢおよびＶＥＧＦＲ２キナーゼ阻害剤としてのピラゾロ［１，５−ａ］ピリジン−３−カルボン酸 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7795273B2 (https=) |
| EP (1) | EP1963316A2 (https=) |
| JP (1) | JP2009518340A (https=) |
| KR (1) | KR20080074161A (https=) |
| AU (1) | AU2006322187A1 (https=) |
| BR (1) | BRPI0619517A2 (https=) |
| CA (1) | CA2629743A1 (https=) |
| RU (1) | RU2008127263A (https=) |
| WO (1) | WO2007065664A2 (https=) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8642597B2 (en) | 2007-08-27 | 2014-02-04 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
| AU2009279936A1 (en) * | 2008-08-05 | 2010-02-11 | Banyu Pharmaceutical Co., Ltd. | Therapeutic compounds |
| PL2342196T3 (pl) | 2008-09-24 | 2015-12-31 | Basf Se | Związki pirazolowe do zwalczania szkodników będących bezkręgowcami |
| CN102223798A (zh) | 2008-09-24 | 2011-10-19 | 巴斯夫欧洲公司 | 用于防治无脊椎动物害虫的吡唑化合物 |
| CN102271515B (zh) | 2008-10-31 | 2014-07-02 | 健泰科生物技术公司 | 吡唑并嘧啶jak抑制剂化合物和方法 |
| UA110324C2 (en) | 2009-07-02 | 2015-12-25 | Genentech Inc | Jak inhibitory compounds based on pyrazolo pyrimidine |
| WO2011003796A1 (en) | 2009-07-06 | 2011-01-13 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
| WO2011003793A1 (en) | 2009-07-06 | 2011-01-13 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
| WO2011009804A2 (en) | 2009-07-24 | 2011-01-27 | Basf Se | Pyridine derivatives compounds for controlling invertebrate pests |
| NZ604708A (en) | 2010-05-20 | 2015-05-29 | Array Biopharma Inc | Macrocyclic compounds as trk kinase inhibitors |
| US8883819B2 (en) | 2011-09-01 | 2014-11-11 | Irm Llc | Bicyclic heterocycle derivatives for the treatment of pulmonary arterial hypertension |
| KR20140105508A (ko) | 2011-12-12 | 2014-09-01 | 닥터 레디스 레보러터리즈 리미티드 | 트로포미오신 수용체 키나제(Trk) 억제제인 치환된 피라졸로[1,5-a]피리딘 |
| CN105164124B (zh) | 2012-11-19 | 2017-03-15 | 诺华股份有限公司 | 用于治疗寄生虫疾病的化合物和组合物 |
| US8871754B2 (en) | 2012-11-19 | 2014-10-28 | Irm Llc | Compounds and compositions for the treatment of parasitic diseases |
| US9073921B2 (en) | 2013-03-01 | 2015-07-07 | Novartis Ag | Salt forms of bicyclic heterocyclic derivatives |
| PE20211782A1 (es) | 2014-05-23 | 2021-09-08 | Hoffmann La Roche | Compuestos de 5-cloro-2-difluorometoxifenil pirazolopirimidina, composiciones y metodos de uso de los mismos |
| NO2719005T3 (https=) | 2014-07-28 | 2018-01-20 | ||
| CN105524058B (zh) * | 2014-10-21 | 2018-03-27 | 广州艾格生物科技有限公司 | 吡唑并[1,5‑a]吡啶类化合物及其应用 |
| HRP20240644T1 (hr) | 2014-11-06 | 2024-08-02 | Bial-R&D Investments, S.A. | Supstituirani pirazolo(1,5-a)pirimidini i njihova uporaba u liječenju medicinskih poremećaja |
| AU2015342883B2 (en) | 2014-11-06 | 2020-07-02 | Bial - R&D Investments, S.A. | Substituted pyrrolo(1,2-a)pyrimidines and their use in the treatment of medical disorders |
| WO2016073889A1 (en) | 2014-11-06 | 2016-05-12 | Lysosomal Therapeutics Inc. | Substituted imidazo[1,5-a]pyrimidines and their use in the treatment of medical disorders |
| BR112018000808A2 (pt) | 2015-07-16 | 2018-09-04 | Array Biopharma Inc | compostos de pirazolo[1,5-a]piridina substituída como inibidores de ret cinase |
| EP3440081A4 (en) | 2016-04-06 | 2019-09-18 | Lysosomal Therapeutics Inc. | PYRROLO [1,2-A] PYRIMIDINYL-CARBOXAMIDE COMPOUNDS AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDER |
| US11192892B2 (en) | 2016-04-06 | 2021-12-07 | Bial—R&D Investments, S.A. | Substituted pyrazolo[1,5-a]pyrimidines for the treatment of medical disorders |
| CA3020305A1 (en) | 2016-04-06 | 2017-10-12 | Lysosomal Therapeutics Inc. | Imidazo [1,5-a]pyrimidinyl carboxamide compounds and their use in the treatment of medical disorders |
| EP3452455A4 (en) | 2016-05-05 | 2019-11-13 | Lysosomal Therapeutics Inc. | SUBSTITUTED IMDAZO [1,2-] PYRIDINES, SUBSTITUTED IMIDAZO [1,2-] PYRAZINES, RELATED COMPOUNDS AND THEIR USE IN THE TREATMENT OF ILLNESSES |
| SG11201809693SA (en) | 2016-05-05 | 2018-11-29 | Lysosomal Therapeutics Inc | SUBSTITUTED IMIDAZO[1,2-b]PYRIDAZINES, SUBSTITUTED IMIDAZO[1,5-b]PYRIDAZINES, RELATED COMPOUNDS, AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS |
| TWI752098B (zh) | 2016-10-10 | 2022-01-11 | 美商亞雷生物製藥股份有限公司 | 作為ret激酶抑制劑之經取代吡唑并[1,5-a]吡啶化合物 |
| TWI704148B (zh) | 2016-10-10 | 2020-09-11 | 美商亞雷生物製藥股份有限公司 | 作為ｒｅｔ激酶抑制劑之經取代吡唑并[1,5-a]吡啶化合物 |
| US11168090B2 (en) | 2017-01-18 | 2021-11-09 | Array Biopharma Inc. | Substituted pyrazolo[1,5-a]pyrazines as RET kinase inhibitors |
| WO2018136663A1 (en) | 2017-01-18 | 2018-07-26 | Array Biopharma, Inc. | Ret inhibitors |
| JOP20190213A1 (ar) | 2017-03-16 | 2019-09-16 | Array Biopharma Inc | مركبات حلقية ضخمة كمثبطات لكيناز ros1 |
| WO2018215389A1 (en) | 2017-05-22 | 2018-11-29 | F. Hoffmann-La Roche Ag | Therapeutic compounds and compositions, and methods of use thereof |
| TWI812649B (zh) | 2017-10-10 | 2023-08-21 | 美商絡速藥業公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之調配物 |
| TWI791053B (zh) | 2017-10-10 | 2023-02-01 | 美商亞雷生物製藥股份有限公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之結晶形式及其醫藥組合物 |
| EP3740491A1 (en) | 2018-01-18 | 2020-11-25 | Array Biopharma, Inc. | Substituted pyrrolo[2,3-d]pyrimidines compounds as ret kinase inhibitors |
| CN111615514B (zh) | 2018-01-18 | 2022-10-11 | 奥瑞生物药品公司 | 作为ret激酶抑制剂的取代的吡唑并[4,3-c]吡啶化合物 |
| WO2019143991A1 (en) | 2018-01-18 | 2019-07-25 | Array Biopharma Inc. | SUBSTITUTED PYRAZOLO[3,4-d]PYRIMIDINE COMPOUNDS AS RET KINASE INHIBITORS |
| EP3849986B1 (en) | 2018-09-10 | 2022-06-08 | Array Biopharma, Inc. | Fused heterocyclic compounds as ret kinase inhibitors |
| WO2021050900A1 (en) | 2019-09-13 | 2021-03-18 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Receptor tyrosine kinase inhibitors for treatment of protein kinase modulation-responsive disease or disorder |
| WO2024123966A1 (en) * | 2022-12-07 | 2024-06-13 | Third Harmonic Bio, Inc. | Compounds and compositions as c-kit kinase inhibitors |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI372050B (en) * | 2003-07-03 | 2012-09-11 | Astex Therapeutics Ltd | (morpholin-4-ylmethyl-1h-benzimidazol-2-yl)-1h-pyrazoles |
| US20050222171A1 (en) | 2004-01-22 | 2005-10-06 | Guido Bold | Organic compounds |
-
2006
- 2006-12-06 AU AU2006322187A patent/AU2006322187A1/en not_active Abandoned
- 2006-12-06 CA CA002629743A patent/CA2629743A1/en not_active Abandoned
- 2006-12-06 EP EP06829351A patent/EP1963316A2/en not_active Withdrawn
- 2006-12-06 BR BRPI0619517-2A patent/BRPI0619517A2/pt not_active Application Discontinuation
- 2006-12-06 WO PCT/EP2006/011722 patent/WO2007065664A2/en not_active Ceased
- 2006-12-06 KR KR1020087013615A patent/KR20080074161A/ko not_active Withdrawn
- 2006-12-06 US US12/096,260 patent/US7795273B2/en not_active Expired - Fee Related
- 2006-12-06 RU RU2008127263/04A patent/RU2008127263A/ru not_active Application Discontinuation
- 2006-12-06 JP JP2008543727A patent/JP2009518340A/ja active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2009518340A5 (https=) | ||
| RU2008127263A (ru) | ПИРАЗОЛ [1,5-a] ПИРИДИН-3-КАРБОНОВЫЕ КИСЛОТЫ В КАЧЕСТВЕ ИНГИБИТОРОВ EphB-И VEGFR2-КИНАЗЫ | |
| JP6909323B2 (ja) | Ｍｄｍ２阻害剤及びそれを使用する治療方法 | |
| CN104870446B (zh) | 取代的嘧啶基和吡啶基吡咯并吡啶酮类、其制备方法及其作为激酶抑制剂的用途 | |
| CN103328447B (zh) | 作为c-Met激酶抑制剂的化合物 | |
| JP6982748B2 (ja) | ２−（１Ｈ−インダゾール−３−イル）−３Ｈ−イミダゾ［４，５−ｃ］ピリジンおよびそれらの抗炎症的使用 | |
| TWI296927B (en) | Substituted 3-amino-thieno[2,3-b]pyridine-2-carboxylic acid amide compounds and processes for preparing and their uses | |
| RU2375363C2 (ru) | Пирролотриазиновые производные анилина, полезные в качестве ингибиторов киназы | |
| CA3077499C (en) | P38 kinase inhibitors reduce dux4 and downstream gene expression for the treatment of fshd | |
| CN101820950B (zh) | 作为刺猬蛋白信号通路调节剂的联苯基甲酰胺类化合物 | |
| CN101679406B (zh) | 用作激酶抑制剂的噻唑基化合物 | |
| RU2008126395A (ru) | 3-(ЗАМЕЩЕННЫЕ АМИНО)ПИРАЗОЛО[3,4-d]ПИРИМИДИНЫ В КАЧЕСТВЕ ИНГИБИТОРОВ ЭФРИН В (EphB) КИНАЗЫ И ВАСКУЛЯРНОГО ЭПИТЕЛИАЛЬНОГО ФАКТОРА РОСТА 2 (VEGFR2) КИНАЗЫ | |
| CN105906631A (zh) | 用于激酶调节的化合物和方法及其适应症 | |
| EP2373664B1 (en) | Bicyclic pyrazoles as protein kinase inhibitors | |
| RU2005122484A (ru) | Композиции, используемые в качестве ингибиторов протеинкиназ | |
| EP1628981A2 (en) | Bicyclicpyrimidones and their use to treat diseases | |
| JP2017533932A (ja) | タンパク質キナーゼ阻害剤としての６−アミノ−７−ビシクロ−７−デアザ−プリン誘導体 | |
| PT2363393E (pt) | Compostos e composições como moduladores da via hedgehog | |
| RU2008106056A (ru) | ПРОИЗВОДНЫЕ ПИРАЗОЛО[1,5-а]ПИРИМИДИН-7-ИЛАМИНА В КАЧЕСТВЕ ИНГИБИТОРОВ ПРОТЕИНКИНАЗЫ | |
| RU2007141767A (ru) | Фенилацетамиды, пригодные в качестве ингибиторов протеинкиназ | |
| AU2015402778B2 (en) | Aminonapthoquinone compounds and pharmaceutical composition for blocking ubiquitination-proteasome system in diseases | |
| CN104837844B (zh) | 作为酪蛋白激酶1 d/e抑制剂的吡唑取代的咪唑并哌嗪 | |
| TW202104212A (zh) | 以雜環化合物作為激酶抑制劑的治療用途 | |
| BR112015030399B1 (pt) | Derivados heterocíclicos, uso dos referidos derivados e composição farmacêutica para a prevenção ou tratamento de doenças associadas com a ativação da proteína stat3 | |
| WO2011161216A1 (en) | Heteroaryl compounds and compositions as protein kinase inhibitors |