JP2009518340A5 - - Google Patents
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- 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
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- 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
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- -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
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- 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
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- 125000002541 furyl group Chemical group 0.000 claims 1
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- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
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- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
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- 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
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- 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
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- 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
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- 125000002971 oxazolyl group Chemical group 0.000 claims 1
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- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
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- 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
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- 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
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| 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)
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| JP2009518340A JP2009518340A (ja) | 2009-05-07 |
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| RU (1) | RU2008127263A (https=) |
| WO (1) | WO2007065664A2 (https=) |
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| CN101835377B (zh) | 2007-08-27 | 2014-12-10 | 巴斯夫欧洲公司 | 用于防治无脊椎动物害虫的吡唑化合物 |
| JP2011530511A (ja) * | 2008-08-05 | 2011-12-22 | メルク・シャープ・エンド・ドーム・コーポレイション | 治療用化合物 |
| KR101364869B1 (ko) | 2008-09-24 | 2014-02-21 | 바스프 에스이 | 무척추 해충을 방제하기 위한 피라졸 화합물 |
| EP2346335B1 (en) | 2008-09-24 | 2018-11-14 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
| EP2348860B1 (en) | 2008-10-31 | 2015-05-27 | Genentech, Inc. | Pyrazolopyrimidine jak inhibitor compounds and methods |
| UA110324C2 (en) | 2009-07-02 | 2015-12-25 | Genentech Inc | Jak inhibitory compounds based on pyrazolo pyrimidine |
| EP2451804B1 (en) | 2009-07-06 | 2014-04-30 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
| ES2461618T3 (es) | 2009-07-06 | 2014-05-20 | Basf Se | Compuestos de piridacina para el control de plagas de invertebrados |
| JP2013500246A (ja) | 2009-07-24 | 2013-01-07 | ビーエーエスエフ ソシエタス・ヨーロピア | 無脊椎動物系害虫防除用ピリジン誘導体化合物 |
| ME03376B (me) | 2010-05-20 | 2020-01-20 | Array Biopharma Inc | Makrociklička jedinjenja kао inhibiтori trk kinaze |
| US8883819B2 (en) | 2011-09-01 | 2014-11-11 | Irm Llc | Bicyclic heterocycle derivatives for the treatment of pulmonary arterial hypertension |
| AU2012351748B2 (en) | 2011-12-12 | 2016-04-14 | Dr. Reddy's Laboratories Ltd. | Substituted pyrazolo[1,5-a] pyridine as tropomyosin receptor kinase (Trk) inhibitors |
| US8871754B2 (en) | 2012-11-19 | 2014-10-28 | Irm Llc | Compounds and compositions for the treatment of parasitic diseases |
| LT2925757T (lt) | 2012-11-19 | 2017-12-27 | Novartis Ag | Junginiai ir kompozicijos, skirti parazitinių ligų gydymui |
| US9073921B2 (en) | 2013-03-01 | 2015-07-07 | Novartis Ag | Salt forms of bicyclic heterocyclic derivatives |
| JP2017516850A (ja) | 2014-05-23 | 2017-06-22 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | Ｊａｋ阻害剤である５−クロロ−２−ジフルオロメトキシフェニルピラゾロピリミジン化合物 |
| 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 |
| EP4406616A3 (en) | 2014-11-06 | 2024-11-06 | Bial-R&D Investments, S.A. | Substituted pyrazolo(1,5-a)pyrimidines and their use in the treatment of medical disorders |
| US20170333435A1 (en) | 2014-11-06 | 2017-11-23 | Lysosomal Therapeutics Inc. | Substituted imidazo[1,5-a]pyrimidines and their use in the treatment of medical disorders |
| US20180185368A1 (en) | 2014-11-06 | 2018-07-05 | Lysosomal Therapeutics Inc. | Substituted pyrrolo[1,2-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 |
| AU2017246455B2 (en) | 2016-04-06 | 2021-09-30 | Bial - R&D Investments, S.A. | Pyrazolo[1,5-a]pyrimidinyl carboxamide compounds and their use in the treatment of medical disorders |
| 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 |
| 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 |
| KR102530515B1 (ko) | 2016-05-05 | 2023-05-09 | 비알 - 알&디 인베스트먼츠, 에스.에이. | 치환된 이미다조[1,2-b]피리다진, 치환된 이미다조[1,5-b]피리다진, 관련 화합물, 및 의학적 장애의 치료에서의 그의 용도 |
| WO2017192931A1 (en) | 2016-05-05 | 2017-11-09 | Lysosomal Therapeutics Inc. | SUBSTITUTED IMDAZO[1,2-α]PYRIDINES, SUBSTITUTED IMIDAZO[1,2-α]PYRAZINES, 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 |
| WO2018136663A1 (en) | 2017-01-18 | 2018-07-26 | Array Biopharma, Inc. | Ret inhibitors |
| WO2018136661A1 (en) | 2017-01-18 | 2018-07-26 | Andrews Steven W | SUBSTITUTED PYRAZOLO[1,5-a]PYRAZINE COMPOUNDS AS RET KINASE INHIBITORS |
| JOP20190213A1 (ar) | 2017-03-16 | 2019-09-16 | Array Biopharma Inc | مركبات حلقية ضخمة كمثبطات لكيناز ros1 |
| MX387969B (es) | 2017-05-22 | 2025-03-19 | Hoffmann La Roche | Composiciones y compuestos terapéuticos, y métodos para su uso. |
| TWI876442B (zh) | 2017-10-10 | 2025-03-11 | 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 |
| EP3740490A1 (en) | 2018-01-18 | 2020-11-25 | Array Biopharma, Inc. | Substituted pyrazolo[3,4-d]pyrimidine compounds as ret kinase inhibitors |
| JP7060694B2 (ja) | 2018-01-18 | 2022-04-26 | アレイ バイオファーマ インコーポレイテッド | Ｒｅｔキナーゼ阻害剤としての置換ピロロ［２，３－ｄ］ピリミジン化合物 |
| US11472802B2 (en) | 2018-01-18 | 2022-10-18 | Array Biopharma Inc. | Substituted pyrazolyl[4,3-c]pyridine compounds as RET kinase inhibitors |
| CN112996794A (zh) | 2018-09-10 | 2021-06-18 | 阿雷生物药品公司 | 作为ret激酶抑制剂的稠合杂环化合物 |
| EP4028133A1 (en) | 2019-09-13 | 2022-07-20 | 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 |
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| 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 |
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2006
- 2006-12-06 CA CA002629743A patent/CA2629743A1/en not_active Abandoned
- 2006-12-06 RU RU2008127263/04A patent/RU2008127263A/ru not_active Application Discontinuation
- 2006-12-06 JP JP2008543727A patent/JP2009518340A/ja active Pending
- 2006-12-06 WO PCT/EP2006/011722 patent/WO2007065664A2/en not_active Ceased
- 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 US US12/096,260 patent/US7795273B2/en not_active Expired - Fee Related
- 2006-12-06 AU AU2006322187A patent/AU2006322187A1/en not_active Abandoned
- 2006-12-06 KR KR1020087013615A patent/KR20080074161A/ko not_active Withdrawn
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