ES2637588T3 - Nuevos compuestos tricíclicos - Google Patents
Nuevos compuestos tricíclicos Download PDFInfo
- Publication number
- ES2637588T3 ES2637588T3 ES10835061.2T ES10835061T ES2637588T3 ES 2637588 T3 ES2637588 T3 ES 2637588T3 ES 10835061 T ES10835061 T ES 10835061T ES 2637588 T3 ES2637588 T3 ES 2637588T3
- Authority
- ES
- Spain
- Prior art keywords
- pyrrolo
- prepared
- pyrazin
- tosyl
- triazolo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
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- 150000001875 compounds Chemical class 0.000 title abstract description 81
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 546
- 238000000034 method Methods 0.000 description 406
- -1 for example Proteins 0.000 description 281
- 238000002360 preparation method Methods 0.000 description 248
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 207
- 235000011121 sodium hydroxide Nutrition 0.000 description 182
- 238000004128 high performance liquid chromatography Methods 0.000 description 141
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 138
- ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 133
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 122
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 122
- 238000000105 evaporative light scattering detection Methods 0.000 description 114
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 111
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 105
- 238000004587 chromatography analysis Methods 0.000 description 97
- 238000001514 detection method Methods 0.000 description 97
- 239000002245 particle Substances 0.000 description 92
- 239000007821 HATU Substances 0.000 description 85
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 74
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 69
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 66
- 230000003287 optical effect Effects 0.000 description 63
- 239000000047 product Substances 0.000 description 59
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 56
- 238000012360 testing method Methods 0.000 description 54
- 239000011159 matrix material Substances 0.000 description 53
- 229940124530 sulfonamide Drugs 0.000 description 50
- 150000003456 sulfonamides Chemical class 0.000 description 47
- 239000011541 reaction mixture Substances 0.000 description 46
- 239000000243 solution Substances 0.000 description 45
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 43
- GYTDJCTUFWFXBE-UHFFFAOYSA-M (2,2,2-trifluoroacetyl)oxymercury Chemical compound [Hg+].[O-]C(=O)C(F)(F)F GYTDJCTUFWFXBE-UHFFFAOYSA-M 0.000 description 42
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 39
- 230000014759 maintenance of location Effects 0.000 description 37
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 35
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 35
- WMSPXQIQBQAWLL-UHFFFAOYSA-N cyclopropanesulfonamide Chemical compound NS(=O)(=O)C1CC1 WMSPXQIQBQAWLL-UHFFFAOYSA-N 0.000 description 34
- 239000000203 mixture Substances 0.000 description 34
- 235000017550 sodium carbonate Nutrition 0.000 description 33
- 229910000029 sodium carbonate Inorganic materials 0.000 description 33
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 31
- 238000000926 separation method Methods 0.000 description 31
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 30
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
- 235000019439 ethyl acetate Nutrition 0.000 description 28
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- 239000003814 drug Substances 0.000 description 26
- 238000000149 argon plasma sintering Methods 0.000 description 25
- 230000023077 detection of light stimulus Effects 0.000 description 25
- 150000001412 amines Chemical class 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 21
- 239000002253 acid Substances 0.000 description 21
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 21
- 230000002829 reductive effect Effects 0.000 description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- QOXHTCOEKWCSKM-UHFFFAOYSA-N 6-tosyl-6h-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(N=CC=2N3C=NN=2)=C3C=C1 QOXHTCOEKWCSKM-UHFFFAOYSA-N 0.000 description 19
- 239000003643 water by type Substances 0.000 description 19
- OXKHPRFGCFJUSK-UHFFFAOYSA-N 3,3,3-trifluoropropane-1-sulfonyl chloride Chemical compound FC(F)(F)CCS(Cl)(=O)=O OXKHPRFGCFJUSK-UHFFFAOYSA-N 0.000 description 18
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 18
- PMSVVUSIPKHUMT-UHFFFAOYSA-N cyanopyrazine Chemical compound N#CC1=CN=CC=N1 PMSVVUSIPKHUMT-UHFFFAOYSA-N 0.000 description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 18
- 229910052731 fluorine Inorganic materials 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 18
- 229910052700 potassium Inorganic materials 0.000 description 17
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
- GTYRFWMSDBGPTI-UHFFFAOYSA-N 5-chloropyrazine-2-carbonitrile Chemical compound ClC1=CN=C(C#N)C=N1 GTYRFWMSDBGPTI-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 16
- 239000003112 inhibitor Substances 0.000 description 16
- LCDCPQHFCOBUEF-UHFFFAOYSA-N pyrrolidine-1-carboxamide Chemical compound NC(=O)N1CCCC1 LCDCPQHFCOBUEF-UHFFFAOYSA-N 0.000 description 16
- 229920006395 saturated elastomer Polymers 0.000 description 16
- LJWZSXDLNMOUIP-UHFFFAOYSA-N N1C=CN=C2N=CC=C21 Chemical class N1C=CN=C2N=CC=C21 LJWZSXDLNMOUIP-UHFFFAOYSA-N 0.000 description 15
- 239000010410 layer Substances 0.000 description 15
- 239000003960 organic solvent Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 14
- PFWWSGFPICCWGU-UHFFFAOYSA-N cyclopropanesulfonyl chloride Chemical compound ClS(=O)(=O)C1CC1 PFWWSGFPICCWGU-UHFFFAOYSA-N 0.000 description 14
- 235000017557 sodium bicarbonate Nutrition 0.000 description 14
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
- 229940124597 therapeutic agent Drugs 0.000 description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 13
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 13
- 102000004127 Cytokines Human genes 0.000 description 13
- 108090000695 Cytokines Proteins 0.000 description 13
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 12
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 239000005557 antagonist Substances 0.000 description 11
- 229910052796 boron Inorganic materials 0.000 description 11
- 201000010099 disease Diseases 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 10
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 10
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 10
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
- 102000000589 Interleukin-1 Human genes 0.000 description 10
- 108010002352 Interleukin-1 Proteins 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 235000011114 ammonium hydroxide Nutrition 0.000 description 10
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 10
- 229940079593 drug Drugs 0.000 description 10
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- OJEOJUQOECNDND-UHFFFAOYSA-N oxetan-3-amine Chemical compound NC1COC1 OJEOJUQOECNDND-UHFFFAOYSA-N 0.000 description 10
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 10
- JZZKMQFRSCBXPJ-UHFFFAOYSA-N 1,5,7,10,11-pentazatricyclo[7.3.0.02,6]dodeca-2(6),3,7,9,11-pentaene Chemical compound N1=CC2=NN=CN2C2=C1NC=C2 JZZKMQFRSCBXPJ-UHFFFAOYSA-N 0.000 description 9
- KIPSRYDSZQRPEA-UHFFFAOYSA-N 2,2,2-trifluoroethanamine Chemical compound NCC(F)(F)F KIPSRYDSZQRPEA-UHFFFAOYSA-N 0.000 description 9
- DVLFYONBTKHTER-UHFFFAOYSA-N 3-(N-morpholino)propanesulfonic acid Chemical compound OS(=O)(=O)CCCN1CCOCC1 DVLFYONBTKHTER-UHFFFAOYSA-N 0.000 description 9
- 208000019693 Lung disease Diseases 0.000 description 9
- 239000007993 MOPS buffer Substances 0.000 description 9
- 229960002170 azathioprine Drugs 0.000 description 9
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 9
- 239000003246 corticosteroid Substances 0.000 description 9
- 229960001334 corticosteroids Drugs 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 description 9
- LPPOVVJDAVMOET-UHFFFAOYSA-N pyrrolidine-1-sulfonamide Chemical compound NS(=O)(=O)N1CCCC1 LPPOVVJDAVMOET-UHFFFAOYSA-N 0.000 description 9
- OQANPHBRHBJGNZ-FYJGNVAPSA-N (3e)-6-oxo-3-[[4-(pyridin-2-ylsulfamoyl)phenyl]hydrazinylidene]cyclohexa-1,4-diene-1-carboxylic acid Chemical compound C1=CC(=O)C(C(=O)O)=C\C1=N\NC1=CC=C(S(=O)(=O)NC=2N=CC=CC=2)C=C1 OQANPHBRHBJGNZ-FYJGNVAPSA-N 0.000 description 8
- 150000005258 1H-pyrrolo(2,3-b)pyridines Chemical group 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 description 8
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 8
- VAMHAZRPNZORAQ-UHFFFAOYSA-N [5-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyrazin-2-yl]methanamine;hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=C(CN)N=C2C=C1 VAMHAZRPNZORAQ-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 229960000485 methotrexate Drugs 0.000 description 8
- 125000006239 protecting group Chemical group 0.000 description 8
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 8
- 230000004044 response Effects 0.000 description 8
- 230000011664 signaling Effects 0.000 description 8
- 229960001940 sulfasalazine Drugs 0.000 description 8
- NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 7
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 7
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 7
- CDBAEFXTCRKJPZ-UHFFFAOYSA-N 3,3-difluoroazetidine;hydron;chloride Chemical compound Cl.FC1(F)CNC1 CDBAEFXTCRKJPZ-UHFFFAOYSA-N 0.000 description 7
- 102100026878 Interleukin-2 receptor subunit alpha Human genes 0.000 description 7
- 208000029523 Interstitial Lung disease Diseases 0.000 description 7
- FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 description 7
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- NVSPJDGXKBDYIZ-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]pyrazine Chemical class C1=NC=CN2C=NN=C21 NVSPJDGXKBDYIZ-UHFFFAOYSA-N 0.000 description 7
- 239000000872 buffer Substances 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 238000000132 electrospray ionisation Methods 0.000 description 7
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 7
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 description 7
- 229960005205 prednisolone Drugs 0.000 description 7
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- HVLZSUXLPDFOKM-DTLFHODZSA-N (1s,2r,4s)-4-acetamido-2-methylcyclopentane-1-carboxylic acid Chemical compound C[C@@H]1C[C@H](NC(C)=O)C[C@@H]1C(O)=O HVLZSUXLPDFOKM-DTLFHODZSA-N 0.000 description 6
- YFXOUKMYZWGUGV-KUARMEPBSA-N 1-((cis)-4-ethylpyrrolidin-3-yl)-6-tosyl-6h-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine hydrochloride Chemical compound Cl.CC[C@H]1CNC[C@H]1C1=NN=C2N1C(C=CN1S(=O)(=O)C=3C=CC(C)=CC=3)=C1N=C2 YFXOUKMYZWGUGV-KUARMEPBSA-N 0.000 description 6
- YYVPZQADFREIFR-UHFFFAOYSA-N 3,3-difluoropyrrolidine;hydrochloride Chemical compound [Cl-].FC1(F)CC[NH2+]C1 YYVPZQADFREIFR-UHFFFAOYSA-N 0.000 description 6
- ZFTZGXBNLSEDTJ-UHFFFAOYSA-N 5-[3-ethyl-4-(1,5,7,10,11-pentazatricyclo[7.3.0.02,6]dodeca-2(6),3,7,9,11-pentaen-12-yl)cyclopentyl]oxypyrazine-2-carbonitrile Chemical compound C1C(C=2N3C=4C=CNC=4N=CC3=NN=2)C(CC)CC1OC1=CN=C(C#N)C=N1 ZFTZGXBNLSEDTJ-UHFFFAOYSA-N 0.000 description 6
- CCQUUHVUQQFTGV-UHFFFAOYSA-N 6-oxo-1h-pyridine-3-carbonitrile Chemical compound OC1=CC=C(C#N)C=N1 CCQUUHVUQQFTGV-UHFFFAOYSA-N 0.000 description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
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| PCT/US2010/058572 WO2011068881A1 (en) | 2009-12-01 | 2010-12-01 | Novel tricyclic compounds |
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| CN102395589A (zh) * | 2009-04-14 | 2012-03-28 | 安斯泰来制药株式会社 | 稠合吡咯并吡啶衍生物 |
| CN102711470A (zh) * | 2009-12-01 | 2012-10-03 | 雅培制药有限公司 | 新的三环化合物 |
| CN102711476B (zh) * | 2009-12-01 | 2014-12-03 | Abbvie公司 | 新的三环化合物 |
| KR20140015162A (ko) | 2010-01-12 | 2014-02-06 | 에프. 호프만-라 로슈 아게 | 트라이사이클릭 헤테로사이클릭 화합물, 조성물 및 이의 사용 방법 |
| AU2012232658B2 (en) * | 2011-03-22 | 2016-06-09 | Advinus Therapeutics Limited | Substituted fused tricyclic compounds, compositions and medicinal applications thereof |
| EP2699572B1 (en) | 2011-04-21 | 2016-08-10 | Origenis GmbH | Heterocyclic compounds as kinase inhibitors |
| WO2013007765A1 (en) * | 2011-07-13 | 2013-01-17 | F. Hoffmann-La Roche Ag | Fused tricyclic compounds for use as inhibitors of janus kinases |
| CN105001226B (zh) * | 2011-08-12 | 2017-09-08 | 日产化学工业株式会社 | 三环杂环化合物和jak抑制剂 |
| US20130072470A1 (en) * | 2011-09-21 | 2013-03-21 | Abbvie Inc. | Novel tricyclic compounds |
| CN102516146B (zh) * | 2011-11-24 | 2013-10-02 | 爱斯特(成都)生物制药有限公司 | 5位为氮的四元氮杂螺环衍生物及其制备方法和用途 |
| JP2015529242A (ja) * | 2012-09-21 | 2015-10-05 | アドヴィヌス セラピューティクス リミテッドAdvinus Therapeutics Limited | 置換された縮合三環式化合物、組成物およびその医薬用途 |
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| JP6539274B2 (ja) | 2013-08-12 | 2019-07-03 | ファーマシューティカル マニュファクチュアリング リサーチ サービシズ,インコーポレーテッド | 押出成形された即放性乱用抑止性丸剤 |
| WO2015061665A1 (en) | 2013-10-24 | 2015-04-30 | Abbvie Inc. | Jak1 selective inhibitor and uses thereof |
| US10172797B2 (en) | 2013-12-17 | 2019-01-08 | Pharmaceutical Manufacturing Research Services, Inc. | Extruded extended release abuse deterrent pill |
| US9492444B2 (en) | 2013-12-17 | 2016-11-15 | Pharmaceutical Manufacturing Research Services, Inc. | Extruded extended release abuse deterrent pill |
| JP6726658B2 (ja) * | 2014-04-11 | 2020-07-22 | イェン、ユンYEN, Yun | ヒストン脱アセチル化酵素阻害剤 |
| JP6561984B2 (ja) | 2014-05-14 | 2019-08-21 | 日産化学株式会社 | 3環性化合物及びjak阻害剤 |
| EP3169315B1 (en) | 2014-07-17 | 2020-06-24 | Pharmaceutical Manufacturing Research Services, Inc. | Immediate release abuse deterrent liquid fill dosage form |
| EP3180344B1 (en) | 2014-08-12 | 2019-09-18 | Pfizer Inc | Pyrrolo[2,3-d]pyrimidine derivatives useful for inhibiting janus kinase |
| CN106922153B (zh) | 2014-08-25 | 2018-11-02 | 蒂威诺特科技有限公司 | 用于大麻素化合物的同时生产的设备和方法 |
| US20160106737A1 (en) | 2014-10-20 | 2016-04-21 | Pharmaceutical Manufacturing Research Services, Inc. | Extended Release Abuse Deterrent Liquid Fill Dosage Form |
| CN120289468A (zh) | 2015-10-16 | 2025-07-11 | 艾伯维公司 | 制备咪唑并[1,2-a]吡咯并[2,3-e]吡嗪类化合物及其固态形式的方法 |
| US11780848B2 (en) | 2015-10-16 | 2023-10-10 | Abbvie Inc. | Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1- carboxamide and solid state forms thereof |
| US11365198B2 (en) | 2015-10-16 | 2022-06-21 | Abbvie Inc. | Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof |
| US11524964B2 (en) | 2015-10-16 | 2022-12-13 | Abbvie Inc. | Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof |
| US20250250277A1 (en) * | 2015-10-16 | 2025-08-07 | Abbvie Inc. | PROCESSES FOR THE PREPARATION OF (3S,4R)-3-ETHYL-4-(3H-IMIDAZO[1,2-a]PYRROLO[2,3-e]-PYRAZIN-8-YL)-N-(2,2,2-TRIFLUOROETHYL)PYRROLIDINE-1-CARBOXAMIDE AND SOLID STATE FORMS THEREOF |
| US11512092B2 (en) | 2015-10-16 | 2022-11-29 | Abbvie Inc. | Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof |
| US12365689B2 (en) | 2015-10-16 | 2025-07-22 | Abbvie Inc. | Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof |
| US10550126B2 (en) | 2015-10-16 | 2020-02-04 | Abbvie Inc. | Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-A]pyrrolo[2,3-e]-pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof |
| WO2017123058A1 (en) | 2016-01-14 | 2017-07-20 | Handok Inc. | Compounds antagonizing a3 adenosine receptor, method for preparing them, and medical-use thereof |
| US20190086392A1 (en) | 2016-03-21 | 2019-03-21 | Inserm (Institut National De La Sante Et De La Recherch Medicale) | Methods for diagnosis and treatment of solar lentigo |
| JOP20190144A1 (ar) | 2016-12-16 | 2019-06-16 | Janssen Pharmaceutica Nv | إيميدازو بيرولو بيريدين كمثبطات لعائلة jak الخاصة بإنزيمات الكيناز |
| SI3555097T1 (sl) * | 2016-12-16 | 2022-09-30 | Janssen Pharmaceutica Nv | Imidazo(4,5-d)pirolo(2,3-b)piridinske spojine kot zaviralci janus kinaz |
| US11564922B2 (en) | 2017-03-09 | 2023-01-31 | Abbvie Inc. | Methods of treating crohn's disease and ulcerative colitis |
| MX2019010733A (es) | 2017-03-09 | 2019-11-01 | Abbvie Inc | Metodos para tratar la enfermedad de crohn y la colitis ulcerosa. |
| 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 |
| US10364245B2 (en) | 2017-06-07 | 2019-07-30 | Chiesi Farmaceutici S.P.A. | Kinase inhibitors |
| WO2019057103A1 (zh) * | 2017-09-21 | 2019-03-28 | 上海华汇拓医药科技有限公司 | Jak激酶抑制剂及其制备方法和在医药领域的应用 |
| AR117398A1 (es) | 2018-03-12 | 2021-08-04 | Abbvie Inc | Inhibidores de la señalización mediada por tirosina cinasa 2 |
| PE20210919A1 (es) | 2018-05-04 | 2021-05-19 | Incyte Corp | Sales de un inhibidor de fgfr |
| TW202016110A (zh) | 2018-06-15 | 2020-05-01 | 比利時商健生藥品公司 | Jak激酶家族之小分子抑制劑 |
| EP3845521B1 (en) | 2018-08-31 | 2024-11-06 | Suzhou Pengxu Pharmatech Co., Ltd. | Synthesis methods for upadacitinib and intermediate thereof |
| CN110872250B (zh) * | 2018-08-31 | 2023-01-10 | 苏州鹏旭医药科技有限公司 | 两种化合物及其制备方法和在合成乌西替尼中的用途 |
| US12024516B2 (en) * | 2018-11-01 | 2024-07-02 | Lynk Pharmaceuticals Co. Ltd. | Tricyclic janus kinase 1 inhibitors, and compositions and methods thereof |
| WO2020092015A1 (en) | 2018-11-02 | 2020-05-07 | University Of Rochester | Therapeutic mitigation of epithelial infection |
| CN111217819B (zh) * | 2018-11-27 | 2021-05-14 | 杭州科巢生物科技有限公司 | 乌帕替尼的合成方法 |
| EP3891151A1 (en) | 2018-12-05 | 2021-10-13 | LEK Pharmaceuticals d.d. | Crystalline phosphate salt of selective jak1 inhibitor upadacitinib |
| WO2020115213A1 (en) | 2018-12-07 | 2020-06-11 | Lek Pharmaceuticals D.D. | Solvate of a selective jak1 inhibitor |
| CN109761885B (zh) * | 2019-02-21 | 2020-06-26 | 北京悦康科创医药科技股份有限公司 | 一种阿加曲班异构体杂质的拆分方法 |
| WO2020177645A1 (zh) * | 2019-03-01 | 2020-09-10 | 苏州科睿思制药有限公司 | 一种Upadacitinib的晶型及其制备方法和用途 |
| MX2021010545A (es) | 2019-03-05 | 2021-11-17 | Incyte Corp | Inhibidores de la vía de cinasa janus 1 (jak1) para el tratamiento de la disfunción crónica del aloinjerto pulmonar. |
| CN113631557B (zh) | 2019-03-14 | 2024-03-15 | 上海华汇拓医药科技有限公司 | Jak激酶抑制剂及其制备方法和在医药领域的应用 |
| WO2020202183A1 (en) | 2019-03-29 | 2020-10-08 | Mylan Laboratories Limited | The process for the preparation of upadacitinib and its intermediates |
| CN111909160B (zh) * | 2019-05-09 | 2024-05-28 | 苏州鹏旭医药科技有限公司 | 一种乌帕替尼盐类化合物及其制备方法 |
| US20220305009A1 (en) * | 2019-07-26 | 2022-09-29 | Zhuhai Yufan Biotechnologies Co., Ltd | Irak4 kinase inhibitor and preparation method therefor |
| CN110938048B (zh) * | 2019-12-02 | 2023-03-28 | 四川大学 | 路易酸催化的插入反应高效合成二氢呋喃衍生物 |
| PE20221504A1 (es) | 2019-12-04 | 2022-09-30 | Incyte Corp | Derivados de un inhibidor de fgfr |
| KR20220118522A (ko) * | 2019-12-19 | 2022-08-25 | 쿠리아 스페인, 에스.에이.유. | 우파다시티닙의 제조를 위한 방법 및 중간체 |
| CN111007184B (zh) * | 2019-12-30 | 2023-05-16 | 天津天士力圣特制药有限公司 | 一种4-甲基哌嗪-1-甲酰氯盐酸盐含量的检测方法 |
| WO2021176473A1 (en) | 2020-03-05 | 2021-09-10 | Mylan Laboratories Limited | A process for the preparation of upadacitinib and its intermediates |
| US11718622B2 (en) | 2020-03-16 | 2023-08-08 | Exelixis Inc. | Heterocyclic adenosine receptor antagonists |
| CN115867136A (zh) * | 2020-04-24 | 2023-03-28 | 堪萨斯大豆委员会 | 一步合成大豆多元醇 |
| WO2021244323A1 (zh) * | 2020-06-05 | 2021-12-09 | 苏州科睿思制药有限公司 | 一种乌帕替尼的晶型及其制备方法和用途 |
| WO2022007629A1 (zh) | 2020-07-08 | 2022-01-13 | 苏州科睿思制药有限公司 | 乌帕替尼的晶型及其制备方法和用途 |
| WO2022044037A1 (en) | 2020-08-24 | 2022-03-03 | Mylan Laboratories Limited | An improved process for the preparation of upadacitinib intermediate |
| AU2021340000A1 (en) * | 2020-09-14 | 2023-05-25 | Galderma Holding SA | Novel jak inhibitor compounds, method for synthesizing same and use thereof |
| KR20230083270A (ko) * | 2020-10-08 | 2023-06-09 | 유니켐 레버러토리스 리미티드 | 치환된 삼환식 화합물 |
| CN112578034B (zh) * | 2020-11-04 | 2022-02-11 | 广东众生睿创生物科技有限公司 | 一种手性胺小分子及其盐的质量控制方法 |
| CN114790208B (zh) * | 2021-01-26 | 2024-06-07 | 珠海宇繁生物科技有限责任公司 | 一种irak4激酶抑制剂及其制备方法 |
| MX2023010642A (es) | 2021-03-11 | 2023-11-28 | Janssen Pharmaceutica Nv | Lorpucitinib para uso en el tratamiento de trastornos mediados por jak. |
| KR20230167057A (ko) * | 2021-04-07 | 2023-12-07 | 애브비 인코포레이티드 | 유파다시티닙의 공결정 |
| CN113200967B (zh) * | 2021-05-07 | 2022-05-24 | 中国人民解放军陆军军医大学 | 吲哚苯醌类化合物、其制备方法及其应用 |
| US20250206717A1 (en) * | 2021-05-13 | 2025-06-26 | Innovstone Therapeutics Limited | Compound having anti-tumor activity and use thereof |
| CN113603693B (zh) * | 2021-07-13 | 2022-08-26 | 陕西丽彩药业有限公司 | 一种2-溴-5-对甲苯磺酰基-5H-吡咯并[2,3-b]吡嗪的制备方法 |
| CN114380837B (zh) * | 2021-12-27 | 2023-06-30 | 上海邈金医药科技有限公司 | 一种具有Janus激酶抑制活性的化合物、包括该化合物的组合物及其应用 |
| EP4215196A1 (en) | 2022-01-24 | 2023-07-26 | Abivax | Combination of 8-chloro-n-(4-(trifluoromethoxy)phenyl)quinolin-2-amine and its derivatives with a jak inhibitor |
| US12487299B2 (en) | 2022-06-20 | 2025-12-02 | Shanghai United Imaging Healthcare Co., Ltd. | Magnetic resonance imaging devices and radiation therapy systems including the magnetic resonance imaging devices |
| CN116836171B (zh) * | 2023-06-30 | 2024-06-04 | 凌科药业(杭州)有限公司 | 一种磺酰胺类化合物及其应用 |
| WO2025102268A1 (en) * | 2023-11-15 | 2025-05-22 | Lynk Pharmaceuticals Co. Ltd. | Solid state forms, pharmaceutical compositions, preparation methods and use thereof |
| CN117285537B (zh) * | 2023-11-27 | 2024-02-06 | 中节能万润股份有限公司 | 一种乌帕替尼的制备方法 |
Family Cites Families (88)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB716327A (en) | 1951-09-05 | 1954-10-06 | Ici Ltd | New heterocyclic compounds |
| US3663559A (en) | 1969-12-03 | 1972-05-16 | Union Carbide Corp | Preparation of oxo-furo-pyridines from furylvinyl isocyanates |
| ZA737247B (en) | 1972-09-29 | 1975-04-30 | Ayerst Mckenna & Harrison | Rapamycin and process of preparation |
| US4053474A (en) * | 1976-04-21 | 1977-10-11 | E. R. Squibb & Sons, Inc. | Pyrazolo[4,3-e][1,2,4]triazolo[4,3-c]pyrimidine |
| US5605690A (en) | 1989-09-05 | 1997-02-25 | Immunex Corporation | Methods of lowering active TNF-α levels in mammals using tumor necrosis factor receptor |
| CA2028235C (en) | 1989-10-20 | 1997-01-21 | Fumio Suzuki | Condensed purine derivatives |
| CA2073500C (en) | 1990-01-11 | 2008-03-25 | Phillip Dan Cook | Compositions and methods for detecting and modulating rna activity and gene expression |
| US6262241B1 (en) | 1990-08-13 | 2001-07-17 | Isis Pharmaceuticals, Inc. | Compound for detecting and modulating RNA activity and gene expression |
| ES2099245T3 (es) | 1990-11-26 | 1997-05-16 | Robert R Recker | Tratamiento de la osteoporosis usando factor de liberacion de hormona de crecimiento (grf) en combinacion con hormona paratiroidea (pth). |
| DE69233701T2 (de) | 1991-03-18 | 2008-04-10 | New York University | Monoklonale und chimäre Antikörper spezifisch für menschlichen Tumornekrosefaktor |
| WO1992022552A1 (en) | 1991-06-14 | 1992-12-23 | The Upjohn Company | IMIDAZO[1,5-a]QUINOXALINES |
| US5212310A (en) | 1991-12-19 | 1993-05-18 | Neurogen Corporation | Certain aryl fused imidazopyrimidines; a new class of GABA brain receptor ligands |
| US5266698A (en) | 1992-04-30 | 1993-11-30 | Neurogen Corporation | Certain aryl and cycloalkyl fused imidazopyrazinediones; a new class of GABA brain receptor ligands |
| US5306819A (en) | 1992-08-27 | 1994-04-26 | Neurogen Corporation | Certain aryl a cycloalkyl fused imidazopyrazinols; and new class of GABA brain receptor ligands |
| PT752248E (pt) | 1992-11-13 | 2001-01-31 | Idec Pharma Corp | Aplicacao terapeutica de anticorpos quimericos e marcados radioactivamente contra antigenios de diferenciacao restrita de linfocitos b humanos para o tratamento do linfoma de celulas b |
| CA2156918A1 (en) | 1993-02-26 | 1994-09-01 | Deen Tulshian | 2-benzyl-polycyclic guanine derivatives and process for preparing them |
| US5736540A (en) | 1993-07-29 | 1998-04-07 | American Cyanamid Company | Tricyclic diazepine vasopressin antagonists and oxytocin antagonists |
| US5733905A (en) | 1993-07-29 | 1998-03-31 | American Cyanamid Company | Tricyclic diazepine vasopressin antagonists and oxytocin antagonists |
| IL112248A0 (en) * | 1994-01-25 | 1995-03-30 | Warner Lambert Co | Tricyclic heteroaromatic compounds and pharmaceutical compositions containing them |
| US5547975A (en) | 1994-09-20 | 1996-08-20 | Talley; John J. | Benzopyranopyrazolyl derivatives for the treatment of inflammation |
| RU2158127C2 (ru) | 1994-12-23 | 2000-10-27 | Варнер-Ламберт Компани | Способы ингибирования тирозинкиназы рецептора эпидермального фактора роста, азотсодержащие трициклические соединения, фармацевтическая композиция, предназначенная для введения ингибитора тирозинкиназы рецептора эпидермального фактора роста, например, erb-b2, erb-b3 или erb-b4, и противозачаточная композиция |
| US5753648A (en) | 1995-01-17 | 1998-05-19 | American Cyanamid Company | Tricyclic benzazepine vasopressin antagonists |
| US5521173A (en) | 1995-01-17 | 1996-05-28 | American Home Products Corporation | Tricyclic benzazepine vasopressin antagonists |
| US5763137A (en) | 1995-08-04 | 1998-06-09 | Agfa-Gevaert, N.V. | Method for making a lithographic printing plate |
| US6090382A (en) | 1996-02-09 | 2000-07-18 | Basf Aktiengesellschaft | Human antibodies that bind human TNFα |
| CA2322311C (en) | 1998-03-04 | 2009-10-13 | Bristol-Myers Squibb Company | Heterocyclo-substituted imidazopyrazine protein tyrosine kinase inhibitors |
| US6448253B1 (en) | 1998-09-16 | 2002-09-10 | King Pharmaceuticals Research And Development, Inc. | Adenosine A3 receptor modulators |
| CO5271670A1 (es) | 1999-10-29 | 2003-04-30 | Pfizer Prod Inc | Antagonistas del factor de liberacion de corticitropina y composiciones relacionadas |
| JP4100865B2 (ja) * | 1999-12-13 | 2008-06-11 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 三環式縮合異項環化合物、その製造法およびその医薬 |
| TWI271406B (en) | 1999-12-13 | 2007-01-21 | Eisai Co Ltd | Tricyclic condensed heterocyclic compounds, preparation method of the same and pharmaceuticals comprising the same |
| EP1325006A2 (en) | 2000-08-07 | 2003-07-09 | Neurogen Corporation | Heterocyclic compounds as ligands of the gaba a? receptor |
| GB0115393D0 (en) * | 2001-06-23 | 2001-08-15 | Aventis Pharma Ltd | Chemical compounds |
| GB0124299D0 (en) | 2001-10-10 | 2001-11-28 | Astrazeneca Ab | Crystal structure of enzyme and uses thereof |
| JP2005529850A (ja) | 2002-02-19 | 2005-10-06 | ファルマシア・イタリア・エス・ピー・エー | 三環系ピラゾール誘導体、その製造方法および抗腫瘍剤としてのその使用 |
| TW200400034A (en) | 2002-05-20 | 2004-01-01 | Bristol Myers Squibb Co | Pyrazolo-pyrimidine aniline compounds useful as kinase inhibitors |
| CN1688573A (zh) * | 2002-08-23 | 2005-10-26 | 希龙公司 | 糖原合成酶激酶3的吡咯基抑制剂 |
| JP2006516561A (ja) * | 2003-01-17 | 2006-07-06 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | 細胞増殖の阻害剤としての2−アミノピリジン置換ヘテロ環類 |
| US7176214B2 (en) | 2003-05-21 | 2007-02-13 | Bristol-Myers Squibb Company | Imidazo-fused oxazolo[4,5-β]pyridine and imidazo-fused thiazolo[4,5-β]pyridine based tricyclic compounds and pharmaceutical compositions comprising same |
| US7169926B1 (en) | 2003-08-13 | 2007-01-30 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| TW200524864A (en) * | 2003-11-10 | 2005-08-01 | Wyeth Corp | Sulfonyltetrahydro-3H-benzo(E)indole-8-amine compounds as 5-hydroxytryptamine-6 ligands |
| JP2007537296A (ja) * | 2004-05-14 | 2007-12-20 | アボット・ラボラトリーズ | 治療薬としてのキナーゼ阻害薬 |
| AR049300A1 (es) * | 2004-06-15 | 2006-07-12 | Schering Corp | Compuestos triciclicos antagonistas de mglur1 como agentes terapeuticos |
| EP1773840B1 (de) | 2004-07-23 | 2010-01-20 | The Medicines Company (Leipzig) GmbH | Substituierte pyrido[3',2':4,5]thieno[3,2-d]pyrimidine und pyrido[3',2':4,5]furo[3,2-d]-pyrimidine zur verwendung als inhibitoren der pda-4 und/oder tnf-alpha freisetzung |
| CN101098872B (zh) | 2004-11-22 | 2012-09-05 | 沃泰克斯药物股份有限公司 | 可用作蛋白激酶抑制剂的吡咯并吡嗪和吡唑并吡嗪 |
| JP5190270B2 (ja) * | 2005-01-14 | 2013-04-24 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 細胞周期キナーゼ阻害剤としてのピラゾロピリミジン |
| ES2411975T3 (es) | 2005-01-14 | 2013-07-09 | Janssen Pharmaceutica Nv | Pirimidinas heterocíclicas anilladas de 5 miembros como inhibidores de cinasas |
| US20060183758A1 (en) | 2005-02-17 | 2006-08-17 | Cb Research And Development, Inc. | Method for synthesis of AZA-annelated pyrroles, thiophenes, and furans |
| WO2006107771A2 (en) * | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | PYRAZOLO[3,4-c]QUINOLINES, PYRAZOLO[3,4-c]NAPHTHYRIDINES, ANALOGS THEREOF, AND METHODS |
| US7737279B2 (en) * | 2005-05-10 | 2010-06-15 | Bristol-Myers Squibb Company | 1,6-dihydro-1,3,5,6-tetraaza-as-indacene based tricyclic compounds and pharmaceutical compositions comprising same |
| US7593820B2 (en) | 2005-05-12 | 2009-09-22 | Cytopia Research Pty Ltd | Crystal structure of human Janus Kinase 2 (JAK2) and uses thereof |
| CN101223168A (zh) * | 2005-07-14 | 2008-07-16 | 安斯泰来制药株式会社 | Janus激酶3的杂环类抑制剂 |
| US8163767B2 (en) | 2005-07-14 | 2012-04-24 | Astellas Pharma Inc. | Heterocyclic Janus Kinase 3 inhibitors |
| CN102127078A (zh) * | 2005-07-14 | 2011-07-20 | 安斯泰来制药株式会社 | Janus激酶3的杂环类抑制剂 |
| WO2009018238A1 (en) | 2007-07-30 | 2009-02-05 | Ardea Biosciences, Inc. | Combinations of mek inhibitors and raf kinase inhibitors and uses thereof |
| CA2618218C (en) | 2005-07-21 | 2015-06-30 | Ardea Biosciences, Inc. | N-(arylamino)-sulfonamide inhibitors of mek |
| KR20080035698A (ko) * | 2005-08-16 | 2008-04-23 | 아이알엠 엘엘씨 | 단백질 키나제 억제제로서의 화합물 및 조성물 |
| JP4551962B2 (ja) | 2005-09-23 | 2010-09-29 | コーリー ファーマシューティカル グループ,インコーポレイテッド | 1H−イミダゾ[4,5−c]ピリジンおよびその類似体のための方法 |
| PE20070543A1 (es) * | 2005-10-06 | 2007-06-14 | Schering Corp | Pirazolopirimidinas como inhibidores de protein quinasas |
| ES2390135T3 (es) | 2005-11-22 | 2012-11-06 | Merck Sharp & Dohme Corp. | Compuestos tricíclicos útiles como inhibidores de quinasas |
| CA2635231C (en) * | 2005-12-29 | 2014-07-15 | Abbott Laboratories | Protein kinase inhibitors |
| ES2473344T3 (es) * | 2006-02-15 | 2014-07-04 | Abbvie Inc. | Las pirazoloquinolonas son potentes inhibidoras de la PARP |
| JP5386350B2 (ja) | 2006-05-31 | 2014-01-15 | タケダ カリフォルニア インコーポレイテッド | グルコキナーゼ活性剤としての、インダゾールおよびイソインドール誘導体 |
| US7629346B2 (en) | 2006-06-19 | 2009-12-08 | Hoffmann-La Roche Inc. | Pyrazinecarboxamide derivatives as CB1 antagonists |
| US20080090834A1 (en) | 2006-07-06 | 2008-04-17 | Pfizer Inc | Selective azole pde10a inhibitor compounds |
| US8063225B2 (en) | 2006-08-14 | 2011-11-22 | Chembridge Corporation | Tricyclic compound derivatives useful in the treatment of neoplastic diseases, inflammatory disorders and immunomodulatory disorders |
| EP2068869A4 (en) * | 2006-10-06 | 2011-05-25 | Abbott Lab | NEW IMIDAZOTHIAZOLE AND IMIDAZOXAZOLE |
| JP5287253B2 (ja) * | 2007-01-12 | 2013-09-11 | アステラス製薬株式会社 | 縮合ピリジン化合物 |
| JP2010532312A (ja) * | 2007-01-30 | 2010-10-07 | バイオジェン・アイデック・エムエイ・インコーポレイテッド | 1−h−ピラゾロ(3,4b)ピリミジン誘導体および有糸分裂キナーゼの調節剤としてのその使用 |
| WO2008112695A2 (en) | 2007-03-12 | 2008-09-18 | Irm Llc | Pyrazolo [3,4-d] pyrimidines and 1, 2, 5, 6-tetraaza- as- indacenes as protein kinase inhibitors for cancer treatment |
| US7691869B2 (en) * | 2007-03-30 | 2010-04-06 | King Pharmaceuticals Research And Development, Inc. | Pyrrolotriazolopyrimidine derivatives, pharmaceutical compositions containing them and methods of treating conditions and diseases mediated by the adenosine A2A receptor activity |
| CA2682304A1 (en) | 2007-04-04 | 2008-10-16 | F. Hoffmann-La Roche Ag | Microbial reduction of an acetoxyketone |
| US8188083B2 (en) * | 2007-06-28 | 2012-05-29 | Abbott Laboratories | Triazolopyridazines |
| AU2009211338B2 (en) * | 2008-02-06 | 2011-12-15 | Novartis Ag | Pyrrolo[2, 3-D] pyrimidines and use thereof as tyrosine kinase inhibitors |
| ATE517107T1 (de) | 2008-02-25 | 2011-08-15 | Hoffmann La Roche | Pyrrolopyrazinkinaseinhibitoren |
| PL2250172T3 (pl) | 2008-02-25 | 2012-01-31 | Hoffmann La Roche | Pirolopirazynowe inhibitory kinazy |
| MX2010008198A (es) | 2008-02-25 | 2010-08-23 | Hoffmann La Roche | Inhibidores de cinasa de pirrolopirazina. |
| WO2009108827A1 (en) | 2008-02-29 | 2009-09-03 | Wyeth | Fused tricyclic pyrazolo[1, 5-a]pyrimidines, methods for preparation and uses thereof |
| TW201612182A (en) | 2008-06-10 | 2016-04-01 | Abbvie Inc | Novel tricyclic compounds |
| EP2320895A2 (en) * | 2008-07-03 | 2011-05-18 | Exelixis, Inc. | Cdk modulators |
| CN102395589A (zh) | 2009-04-14 | 2012-03-28 | 安斯泰来制药株式会社 | 稠合吡咯并吡啶衍生物 |
| US8361962B2 (en) | 2009-07-27 | 2013-01-29 | Roche Palo Alto Llc | Tricyclic inhibitors of JAK |
| CN102711470A (zh) | 2009-12-01 | 2012-10-03 | 雅培制药有限公司 | 新的三环化合物 |
| CN102711476B (zh) * | 2009-12-01 | 2014-12-03 | Abbvie公司 | 新的三环化合物 |
| WO2011156698A2 (en) | 2010-06-11 | 2011-12-15 | Abbott Laboratories | NOVEL PYRAZOLO[3,4-d]PYRIMIDINE COMPOUNDS |
| WO2012149280A2 (en) | 2011-04-29 | 2012-11-01 | Abbott Laboratories | Novel tricyclic compounds |
| US20130072470A1 (en) | 2011-09-21 | 2013-03-21 | Abbvie Inc. | Novel tricyclic compounds |
| WO2015061665A1 (en) | 2013-10-24 | 2015-04-30 | Abbvie Inc. | Jak1 selective inhibitor and uses thereof |
| CN120289468A (zh) | 2015-10-16 | 2025-07-11 | 艾伯维公司 | 制备咪唑并[1,2-a]吡咯并[2,3-e]吡嗪类化合物及其固态形式的方法 |
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