EA019554B1 - Аминопиразольное соединение - Google Patents
Аминопиразольное соединение Download PDFInfo
- Publication number
- EA019554B1 EA019554B1 EA201170831A EA201170831A EA019554B1 EA 019554 B1 EA019554 B1 EA 019554B1 EA 201170831 A EA201170831 A EA 201170831A EA 201170831 A EA201170831 A EA 201170831A EA 019554 B1 EA019554 B1 EA 019554B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- methyl
- chloro
- cells
- pyridazin
- morpholinomethyl
- Prior art date
Links
- -1 Amino pyrazole compound Chemical class 0.000 title claims description 48
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims abstract description 8
- 208000032839 leukemia Diseases 0.000 claims abstract description 6
- 206010006187 Breast cancer Diseases 0.000 claims abstract description 5
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 5
- 208000034578 Multiple myelomas Diseases 0.000 claims abstract description 5
- 206010035226 Plasma cell myeloma Diseases 0.000 claims abstract description 5
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 5
- 208000005017 glioblastoma Diseases 0.000 claims abstract description 5
- 206010060862 Prostate cancer Diseases 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 66
- 150000003839 salts Chemical class 0.000 claims description 15
- VRHSUUSKSRWSLL-UHFFFAOYSA-N 2-(5-methyl-1H-pyrazol-3-yl)-8-(morpholin-4-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound CC1=CC(=NN1)C=1N=C2N(N=C(C=C2CN2CCOCC2)N)C=1 VRHSUUSKSRWSLL-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 208000008601 Polycythemia Diseases 0.000 claims description 6
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 6
- 208000032027 Essential Thrombocythemia Diseases 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 208000003476 primary myelofibrosis Diseases 0.000 claims description 5
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 4
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 4
- 208000014767 Myeloproliferative disease Diseases 0.000 claims description 4
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 208000037398 BCR-ABL1 negative atypical chronic myeloid leukemia Diseases 0.000 claims description 3
- 208000037379 Myeloid Chronic Atypical BCR-ABL Negative Leukemia Diseases 0.000 claims description 3
- 201000004892 atypical chronic myeloid leukemia Diseases 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 208000016595 therapy related acute myeloid leukemia and myelodysplastic syndrome Diseases 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 2
- DCLWNTIANRACSB-UHFFFAOYSA-N imidazo[1,2-b]pyridazin-6-amine Chemical compound N1=C(N)C=CC2=NC=CN21 DCLWNTIANRACSB-UHFFFAOYSA-N 0.000 claims description 2
- LETVJWLLIMJADE-UHFFFAOYSA-N pyridazin-3-amine Chemical compound NC1=CC=CN=N1 LETVJWLLIMJADE-UHFFFAOYSA-N 0.000 claims description 2
- 230000008520 organization Effects 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 201000001514 prostate carcinoma Diseases 0.000 claims 1
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 abstract description 2
- 206010028980 Neoplasm Diseases 0.000 abstract description 2
- 210000004027 cell Anatomy 0.000 description 101
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 81
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 27
- 239000002953 phosphate buffered saline Substances 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- 239000002609 medium Substances 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 238000004611 spectroscopical analysis Methods 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 102000003951 Erythropoietin Human genes 0.000 description 6
- 108090000394 Erythropoietin Proteins 0.000 description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 229940105423 erythropoietin Drugs 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000011534 incubation Methods 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- 239000012224 working solution Substances 0.000 description 5
- GIMRDGMAHSBGHG-UHFFFAOYSA-N (4-chloro-2-fluorophenyl)-(6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)methanone Chemical compound CC=1N=C2C=CC(Cl)=NN2C=1C(=O)C1=CC=C(Cl)C=C1F GIMRDGMAHSBGHG-UHFFFAOYSA-N 0.000 description 4
- 230000003115 biocidal effect Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000000855 fungicidal effect Effects 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000012679 serum free medium Substances 0.000 description 4
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 4
- WXZUHCAKLKTCGB-UHFFFAOYSA-N (4-chloro-2-fluorophenyl)-[6-chloro-2-methyl-8-(morpholin-4-ylmethyl)imidazo[1,2-b]pyridazin-3-yl]methanone Chemical compound C=1C(Cl)=NN2C(C(=O)C=3C(=CC(Cl)=CC=3)F)=C(C)N=C2C=1CN1CCOCC1 WXZUHCAKLKTCGB-UHFFFAOYSA-N 0.000 description 3
- XXKYRXQRSRDCAR-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-5-methylpyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1CN1C(C)=CC(N)=N1 XXKYRXQRSRDCAR-UHFFFAOYSA-N 0.000 description 3
- FYZHQRGIHWWQLB-UHFFFAOYSA-N 2-chloro-1-(4-chloro-2-fluorophenyl)ethanone Chemical compound FC1=CC(Cl)=CC=C1C(=O)CCl FYZHQRGIHWWQLB-UHFFFAOYSA-N 0.000 description 3
- NDAJNMAAXXIADY-UHFFFAOYSA-N 2-methylpropanimidamide Chemical compound CC(C)C(N)=N NDAJNMAAXXIADY-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000008098 formaldehyde solution Substances 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000035772 mutation Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 230000019491 signal transduction Effects 0.000 description 3
- 229940054269 sodium pyruvate Drugs 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 3
- VNTZQYCUWPBWSH-UHFFFAOYSA-N (4-chloro-2-fluorophenyl)-[6-chloro-2-methyl-8-(morpholin-4-ylmethyl)imidazo[1,2-b]pyridazin-3-yl]methanol Chemical compound C=1C(Cl)=NN2C(C(O)C=3C(=CC(Cl)=CC=3)F)=C(C)N=C2C=1CN1CCOCC1 VNTZQYCUWPBWSH-UHFFFAOYSA-N 0.000 description 2
- XMPHUNHAMDBTBE-UHFFFAOYSA-N (4-methoxyphenyl)methylhydrazine;dihydrochloride Chemical compound Cl.Cl.COC1=CC=C(CNN)C=C1 XMPHUNHAMDBTBE-UHFFFAOYSA-N 0.000 description 2
- OIGMDNONQJGUCF-UHFFFAOYSA-N 1-(4-chloro-2-fluorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1F OIGMDNONQJGUCF-UHFFFAOYSA-N 0.000 description 2
- HXOQAJBRGYFLFH-UHFFFAOYSA-N 2-[[6-chloro-3-(4-chloro-2-fluorobenzoyl)-2-methylimidazo[1,2-b]pyridazin-8-yl]methyl]isoindole-1,3-dione Chemical compound CC=1N=C2C(CN3C(C4=CC=CC=C4C3=O)=O)=CC(Cl)=NN2C=1C(=O)C1=CC=C(Cl)C=C1F HXOQAJBRGYFLFH-UHFFFAOYSA-N 0.000 description 2
- DTXVKPOKPFWSFF-UHFFFAOYSA-N 3(S)-hydroxy-13-cis-eicosenoyl-CoA Chemical compound NC1=CC=C(Cl)N=N1 DTXVKPOKPFWSFF-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- HINYAGKLTKBNMH-UHFFFAOYSA-N 4-[[6-chloro-3-[(4-chloro-2-fluorophenyl)methyl]-2-methylimidazo[1,2-b]pyridazin-8-yl]methyl]morpholine Chemical compound C=1C(Cl)=NN2C(CC=3C(=CC(Cl)=CC=3)F)=C(C)N=C2C=1CN1CCOCC1 HINYAGKLTKBNMH-UHFFFAOYSA-N 0.000 description 2
- FYTLHYRDGXRYEY-UHFFFAOYSA-N 5-Methyl-3-pyrazolamine Chemical compound CC=1C=C(N)NN=1 FYTLHYRDGXRYEY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 101100058598 Arabidopsis thaliana BPM1 gene Proteins 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229920000881 Modified starch Polymers 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 2
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- BVMQMWQPSXROEQ-UHFFFAOYSA-N [8-(aminomethyl)-6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl]-(4-chloro-2-fluorophenyl)methanone Chemical compound CC=1N=C2C(CN)=CC(Cl)=NN2C=1C(=O)C1=CC=C(Cl)C=C1F BVMQMWQPSXROEQ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 239000013058 crude material Substances 0.000 description 2
- 229940008099 dimethicone Drugs 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 210000003743 erythrocyte Anatomy 0.000 description 2
- 239000012091 fetal bovine serum Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000003102 growth factor Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 239000005416 organic matter Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- LAAOJPYAGIBKBK-UHFFFAOYSA-N tert-butyl n-[(4-methoxyphenyl)methylamino]carbamate Chemical compound COC1=CC=C(CNNC(=O)OC(C)(C)C)C=C1 LAAOJPYAGIBKBK-UHFFFAOYSA-N 0.000 description 2
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 1
- FOZVXADQAHVUSV-UHFFFAOYSA-N 1-bromo-2-(2-bromoethoxy)ethane Chemical compound BrCCOCCBr FOZVXADQAHVUSV-UHFFFAOYSA-N 0.000 description 1
- NSEQDDGTNOMRHQ-UHFFFAOYSA-N 2-[(4-methoxyphenyl)methyl]-5-methylpyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1CN1C(N)=CC(C)=N1 NSEQDDGTNOMRHQ-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- 102000007644 Colony-Stimulating Factors Human genes 0.000 description 1
- 108010071942 Colony-Stimulating Factors Proteins 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 241000402754 Erythranthe moschata Species 0.000 description 1
- 102000004889 Interleukin-6 Human genes 0.000 description 1
- 108090001005 Interleukin-6 Proteins 0.000 description 1
- 102000006503 Janus Kinase 2 Human genes 0.000 description 1
- 108010019437 Janus Kinase 2 Proteins 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 101800004937 Protein C Proteins 0.000 description 1
- 102000017975 Protein C Human genes 0.000 description 1
- 101800001700 Saposin-D Proteins 0.000 description 1
- 229940124639 Selective inhibitor Drugs 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- 206010047249 Venous thrombosis Diseases 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000003305 autocrine Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000006552 constitutive activation Effects 0.000 description 1
- 230000037011 constitutive activity Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000008482 dysregulation Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 210000003013 erythroid precursor cell Anatomy 0.000 description 1
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000005429 filling process Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 201000005787 hematologic cancer Diseases 0.000 description 1
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940100601 interleukin-6 Drugs 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 1
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011812 mixed powder Substances 0.000 description 1
- 210000000822 natural killer cell Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- MHHDXUNFNAZUGB-UHFFFAOYSA-N oxidovanadium(2+) Chemical compound [V+2]=O MHHDXUNFNAZUGB-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N phenylalanine group Chemical group N[C@@H](CC1=CC=CC=C1)C(=O)O COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000012716 precipitator Substances 0.000 description 1
- 210000001948 pro-b lymphocyte Anatomy 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 229960000856 protein c Drugs 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- IWKLCYXLUROGIV-NTEUORMPSA-N tert-butyl n-[(e)-(4-methoxyphenyl)methylideneamino]carbamate Chemical compound COC1=CC=C(\C=N\NC(=O)OC(C)(C)C)C=C1 IWKLCYXLUROGIV-NTEUORMPSA-N 0.000 description 1
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000001262 western blot Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring 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
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12285408P | 2008-12-16 | 2008-12-16 | |
| PCT/US2009/067056 WO2010074947A1 (en) | 2008-12-16 | 2009-12-08 | Amino pyrazole compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201170831A1 EA201170831A1 (ru) | 2011-12-30 |
| EA019554B1 true EA019554B1 (ru) | 2014-04-30 |
Family
ID=41630090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201170831A EA019554B1 (ru) | 2008-12-16 | 2009-12-08 | Аминопиразольное соединение |
Country Status (38)
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2435646A (en) * | 2006-03-01 | 2007-09-05 | Spin Tec Engineering Gmbh | Apparatus and method of extraction of an arthropod gland |
| US8105633B2 (en) * | 2006-03-01 | 2012-01-31 | Spintec Engineering Gmbh | Method and apparatus for extraction of arthropod gland |
| US20110121485A1 (en) * | 2006-10-30 | 2011-05-26 | Spintec Engineering Gmbh | Method and apparatus for the manufacture of a fiber |
| KR20130131461A (ko) * | 2011-03-07 | 2013-12-03 | 폰다지오네 텔레톤 | Tfeb 변종 및 그의 용도 |
| PH12013502530A1 (en) * | 2011-06-15 | 2014-01-27 | Life And Brain Gmbh | Glioblastoma inhibiting compounds and their use |
| US20150182490A1 (en) | 2012-06-26 | 2015-07-02 | Del Mar Pharmaceuticals | Methods for treating tyrosine-kinase-inhibitor-resistant malignancies in patients with genetic polymorphisms or ahi1 dysregulations or mutations employing dianhydrogalactitol, diacetyldianhydrogalactitol, dibromodulcitol, or analogs or derivatives thereof |
| PL400213A1 (pl) | 2012-08-01 | 2014-02-03 | Celon Pharma Spólka Z Ograniczona Odpowiedzialnoscia | Pochodne imidazo[1,2-b]pirydazyno-6-aminy jako inhibitory kinazy JAK-2 |
| RS63364B1 (sr) | 2014-08-11 | 2022-07-29 | Acerta Pharma Bv | Terapeutske kombinacije btk inhibitora, pd-1 inhibitora i/ili pd-l1 inhibitora |
| WO2016024232A1 (en) | 2014-08-11 | 2016-02-18 | Acerta Pharma B.V. | Therapeutic combinations of a btk inhibitor, a pi3k inhibitor, a jak-2 inhibitor and/or a cdk 4/6 inhibitor |
| SMT202100674T1 (it) | 2014-08-11 | 2022-01-10 | Acerta Pharma Bv | Combinazioni terapeutiche di un inibitore di btk e un inibitore di bcl-2 |
| US11299494B2 (en) * | 2016-11-17 | 2022-04-12 | Bristol-Myers Squibb Company | Substituted imidazo[1,2-b]pyridazines as interleukin-23 and interferon-α modulators |
| WO2018167283A1 (en) | 2017-03-17 | 2018-09-20 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for the diagnosis and treatment of pancreatic ductal adenocarcinoma associated neural remodeling |
| US20200088732A1 (en) | 2017-04-13 | 2020-03-19 | INSERM (Institut National de la Santé et de la Recherche Mèdicale) | Methods for the diagnosis and treatment of pancreatic ductal adenocarcinoma |
| KR102328682B1 (ko) | 2018-08-27 | 2021-11-18 | 주식회사 대웅제약 | 신규한 헤테로사이클릭아민 유도체 및 이를 포함하는 약학 조성물 |
| WO2020092015A1 (en) | 2018-11-02 | 2020-05-07 | University Of Rochester | Therapeutic mitigation of epithelial infection |
| CN110305140B (zh) | 2019-07-30 | 2020-08-04 | 上海勋和医药科技有限公司 | 二氢吡咯并嘧啶类选择性jak2抑制剂 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007009773A1 (en) * | 2005-07-21 | 2007-01-25 | Novartis Ag | Pyrazolo[1.5-a]pyrimidin-7-yl amine derivatives as protein kinase inhibitors |
| US20070083044A1 (en) * | 2005-10-06 | 2007-04-12 | Schering Corporation | Pyrazolopyrimidines as protein kinase inhibitors |
| WO2007044426A2 (en) * | 2005-10-06 | 2007-04-19 | Schering Corporation | Pyrazolopyrimidines as protein kinase inhibitors |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0116493A (pt) | 2000-12-21 | 2003-09-30 | Vertex Pharma | Compostos de pirazol úteis como inibidores de proteìna cinase |
| JP2003137785A (ja) * | 2001-08-23 | 2003-05-14 | Takeda Chem Ind Ltd | Ｊｎｋ活性化阻害剤 |
| CA2467718C (en) | 2001-12-21 | 2011-04-26 | Anormed Inc. | Chemokine receptor binding heterocyclic compounds with enhanced efficacy |
| KR20070104936A (ko) | 2005-02-16 | 2007-10-29 | 아스트라제네카 아베 | 화합물 |
| KR101362621B1 (ko) | 2005-02-16 | 2014-02-13 | 아스트라제네카 아베 | 화합물 |
| BRPI0613501A2 (pt) * | 2005-07-01 | 2011-01-11 | Irm Llc | composto, composição farmacêutica e uso do mesmo |
| US7728017B2 (en) | 2005-11-30 | 2010-06-01 | Vertex Pharmaceuticals Incorporated | Inhibitors of c-Met and uses thereof |
| US7989459B2 (en) | 2006-02-17 | 2011-08-02 | Pharmacopeia, Llc | Purinones and 1H-imidazopyridinones as PKC-theta inhibitors |
| CN101594909A (zh) | 2006-09-07 | 2009-12-02 | 比奥根艾迪克Ma公司 | 用于治疗炎性病症、细胞增殖性失调、免疫失调的irak调节剂 |
| BRPI0718266A2 (pt) * | 2006-10-30 | 2014-01-07 | Novartis Ag | Compostos heterocíclicos como agentes anti-inflamatórios. |
| CN101679429A (zh) * | 2007-04-18 | 2010-03-24 | 阿斯利康(瑞典)有限公司 | 5-氨基吡唑-3-基-3h-咪唑并[4,5-b]吡啶衍生物及其治疗癌的用途 |
| MX2009012612A (es) | 2007-05-23 | 2009-12-07 | Pharmacopeia Llc | Purinonas e inhibidores 1h-imidazopiridinonas como pkc-theta. |
| WO2009062059A2 (en) | 2007-11-08 | 2009-05-14 | Pharmacopeia, Inc. | Isomeric purinones and 1h-imidazopyridinones as pkc-theta inhibitors |
-
2009
- 2009-11-30 PA PA20098851101A patent/PA8851101A1/es unknown
- 2009-12-01 AR ARP090104627A patent/AR074240A1/es unknown
- 2009-12-01 JO JO2009459A patent/JO2833B1/en active
- 2009-12-04 TW TW098141606A patent/TWI440640B/zh not_active IP Right Cessation
- 2009-12-08 WO PCT/US2009/067056 patent/WO2010074947A1/en not_active Ceased
- 2009-12-08 PT PT97958425T patent/PT2379557E/pt unknown
- 2009-12-08 CN CN2009801481167A patent/CN102232075B/zh not_active Expired - Fee Related
- 2009-12-08 PE PE2011001082A patent/PE20110549A1/es not_active Application Discontinuation
- 2009-12-08 BR BRPI0923048A patent/BRPI0923048A2/pt not_active IP Right Cessation
- 2009-12-08 MY MYPI2011002704A patent/MY158691A/en unknown
- 2009-12-08 PL PL09795842T patent/PL2379557T3/pl unknown
- 2009-12-08 HR HRP20120918AT patent/HRP20120918T1/hr unknown
- 2009-12-08 SI SI200930448T patent/SI2379557T1/sl unknown
- 2009-12-08 EP EP09795842A patent/EP2379557B1/en not_active Not-in-force
- 2009-12-08 UA UAA201107565A patent/UA104743C2/ru unknown
- 2009-12-08 CA CA2744714A patent/CA2744714C/en not_active Expired - Fee Related
- 2009-12-08 SG SG2011044161A patent/SG172202A1/en unknown
- 2009-12-08 DK DK09795842.5T patent/DK2379557T3/da active
- 2009-12-08 JP JP2011540809A patent/JP5509217B2/ja not_active Expired - Fee Related
- 2009-12-08 EA EA201170831A patent/EA019554B1/ru not_active IP Right Cessation
- 2009-12-08 NZ NZ592641A patent/NZ592641A/xx not_active IP Right Cessation
- 2009-12-08 MX MX2011006441A patent/MX2011006441A/es active IP Right Grant
- 2009-12-08 AU AU2009330503A patent/AU2009330503B2/en not_active Ceased
- 2009-12-08 KR KR1020117013705A patent/KR101300458B1/ko not_active Expired - Fee Related
- 2009-12-08 ES ES09795842T patent/ES2396617T3/es active Active
- 2009-12-08 US US12/742,302 patent/US20100286139A1/en not_active Abandoned
- 2009-12-08 US US12/632,879 patent/US7897600B2/en not_active Expired - Fee Related
-
2011
- 2011-05-23 IL IL213065A patent/IL213065A0/en unknown
- 2011-05-27 ZA ZA2011/03942A patent/ZA201103942B/en unknown
- 2011-06-09 TN TN2011000292A patent/TN2011000292A1/fr unknown
- 2011-06-14 MA MA33943A patent/MA32900B1/fr unknown
- 2011-06-15 CO CO11074831A patent/CO6331442A2/es active IP Right Grant
- 2011-06-15 CL CL2011001445A patent/CL2011001445A1/es unknown
- 2011-06-15 DO DO2011000190A patent/DOP2011000190A/es unknown
- 2011-06-15 EC EC2011011132A patent/ECSP11011132A/es unknown
- 2011-06-16 SV SV2011003949A patent/SV2011003949A/es not_active Application Discontinuation
- 2011-06-16 HN HN2011001697A patent/HN2011001697A/es unknown
- 2011-06-17 CR CR20110341A patent/CR20110341A/es not_active Application Discontinuation
-
2012
- 2012-11-27 CY CY20121101146T patent/CY1113637T1/el unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007009773A1 (en) * | 2005-07-21 | 2007-01-25 | Novartis Ag | Pyrazolo[1.5-a]pyrimidin-7-yl amine derivatives as protein kinase inhibitors |
| US20070083044A1 (en) * | 2005-10-06 | 2007-04-12 | Schering Corporation | Pyrazolopyrimidines as protein kinase inhibitors |
| WO2007044426A2 (en) * | 2005-10-06 | 2007-04-19 | Schering Corporation | Pyrazolopyrimidines as protein kinase inhibitors |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2009330503B2 (en) | Amino pyrazole compound | |
| JP7337951B2 (ja) | 癌を治療するための窒素含有芳香族ヘテロ環アミド誘導体 | |
| JP5926727B2 (ja) | 置換イミダゾ［１，２−ｂ］ピリダジン | |
| KR20100016431A (ko) | 약학적 화합물 | |
| US10435403B2 (en) | Positive allosteric modulators of muscarinic M2 receptor | |
| US11472803B2 (en) | 7-substituted 1-aryl-naphthyridine-3-carboxylic acid amides and use thereof | |
| WO2020224626A9 (zh) | 用作激酶抑制剂的化合物及其应用 | |
| EP4434986A1 (en) | 15-pgdh inhibitor and use thereof | |
| US9290503B2 (en) | Tricyclic compound derivatives useful in the treatment of neoplastic diseases, inflammatory disorders and immunomodulatory disorders | |
| EP2370446A1 (fr) | DERIVES DE 6-CYCLOAMINO-3-(1H-PYRROLO[2,3-b]PYRIDIN-4-YL)IMIDAZO[1,2-b]-PYRIDAZINE, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE | |
| EA005065B1 (ru) | Энантиомер 1,2-аннелированного хиназолина, ингибирующий фарнезилтрансферазу | |
| TW202221007A (zh) | 巨環化合物 | |
| HK40110628A (en) | 15-pgdh inhibitor and use thereof | |
| HK40119224A (en) | Combination of anticancer agents comprising a bifunctional compound with g12d mutant kras inhibitory activity | |
| WO2026064705A1 (en) | 5/5-5/6-bisaryl compounds as transforming growth factor-β activated kinase inhibitors | |
| CN120118074A (zh) | PI3Kα抑制剂化合物、药物组合物及其应用 | |
| HK1160109B (en) | Amino pyrazole compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AZ BY KG MD TJ TM |
|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM KZ RU |