HRP20090380T1 - SUPSTITUIRANI 1H-PIROLO[3,2-b, 3,2-c, i 2,3-c]PIRIDIN-2-KARBOKSAMIDI I SRODNI ANALOZI KAO INHIBITORI KAZEIN-KINAZE Iε - Google Patents
SUPSTITUIRANI 1H-PIROLO[3,2-b, 3,2-c, i 2,3-c]PIRIDIN-2-KARBOKSAMIDI I SRODNI ANALOZI KAO INHIBITORI KAZEIN-KINAZE Iε Download PDFInfo
- Publication number
- HRP20090380T1 HRP20090380T1 HR20090380T HRP20090380T HRP20090380T1 HR P20090380 T1 HRP20090380 T1 HR P20090380T1 HR 20090380 T HR20090380 T HR 20090380T HR P20090380 T HRP20090380 T HR P20090380T HR P20090380 T1 HRP20090380 T1 HR P20090380T1
- Authority
- HR
- Croatia
- Prior art keywords
- pyrrolo
- pyridine
- carboxylic acid
- alkyl
- acid amide
- Prior art date
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- 102000008122 Casein Kinase I Human genes 0.000 title 1
- 108010049812 Casein Kinase I Proteins 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 33
- 150000001875 compounds Chemical class 0.000 claims abstract 30
- 125000002252 acyl group Chemical group 0.000 claims abstract 22
- 125000003118 aryl group Chemical group 0.000 claims abstract 21
- -1 methylenedioxy Chemical group 0.000 claims abstract 15
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 13
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract 13
- 150000002367 halogens Chemical group 0.000 claims abstract 13
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 11
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 11
- 125000001424 substituent group Chemical group 0.000 claims abstract 11
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 7
- 125000002619 bicyclic group Chemical group 0.000 claims abstract 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 7
- 125000002950 monocyclic group Chemical group 0.000 claims abstract 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 5
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims abstract 4
- 150000003839 salts Chemical class 0.000 claims abstract 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 125000005842 heteroatom Chemical group 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 125000006413 ring segment Chemical group 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims 16
- 239000002904 solvent Substances 0.000 claims 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 150000001408 amides Chemical class 0.000 claims 7
- 208000019116 sleep disease Diseases 0.000 claims 6
- 208000020685 sleep-wake disease Diseases 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 5
- KBHQUFPZXCNYKN-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=N1 KBHQUFPZXCNYKN-UHFFFAOYSA-N 0.000 claims 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 4
- CCFGTKQIRWHYTB-UHFFFAOYSA-N 2-methyl-3-nitropyridine Chemical class CC1=NC=CC=C1[N+]([O-])=O CCFGTKQIRWHYTB-UHFFFAOYSA-N 0.000 claims 3
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 208000019022 Mood disease Diseases 0.000 claims 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- RSFNGIUFEFLHRD-UHFFFAOYSA-N 1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical class C1=NC=C2NC(C(=O)N)=CC2=C1 RSFNGIUFEFLHRD-UHFFFAOYSA-N 0.000 claims 2
- PWWYFIZEQHFRJH-UHFFFAOYSA-N 1h-pyrrolo[2,3-c]pyridine-2-carboxylic acid Chemical compound C1=NC=C2NC(C(=O)O)=CC2=C1 PWWYFIZEQHFRJH-UHFFFAOYSA-N 0.000 claims 2
- YWHNNPXTZCBOJQ-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical class C1=CC=C2NC(C(=O)N)=CC2=N1 YWHNNPXTZCBOJQ-UHFFFAOYSA-N 0.000 claims 2
- ANFOMGVCGLRXAC-UHFFFAOYSA-N 1h-pyrrolo[3,2-c]pyridine-2-carboxylic acid Chemical compound N1=CC=C2NC(C(=O)O)=CC2=C1 ANFOMGVCGLRXAC-UHFFFAOYSA-N 0.000 claims 2
- YSQIQQHDYNAJFB-UHFFFAOYSA-N 2-hydroxy-3-(3-nitropyridin-2-yl)prop-2-enoic acid Chemical class OC(=O)C(O)=CC1=NC=CC=C1[N+]([O-])=O YSQIQQHDYNAJFB-UHFFFAOYSA-N 0.000 claims 2
- MVYAOVJLDIGFIU-UHFFFAOYSA-N 2-hydroxy-3-(3-nitropyridin-4-yl)prop-2-enoic acid Chemical compound OC(=O)C(O)=CC1=CC=NC=C1[N+]([O-])=O MVYAOVJLDIGFIU-UHFFFAOYSA-N 0.000 claims 2
- FDBNQCLBVNRUPI-UHFFFAOYSA-N 2-hydroxy-3-(4-nitropyridin-3-yl)prop-2-enoic acid Chemical compound OC(=O)C(O)=CC1=CN=CC=C1[N+]([O-])=O FDBNQCLBVNRUPI-UHFFFAOYSA-N 0.000 claims 2
- UXDLGSLCSHLAJR-UHFFFAOYSA-N 3-(3-fluorophenyl)sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=CN=C2C=1SC1=CC=CC(F)=C1 UXDLGSLCSHLAJR-UHFFFAOYSA-N 0.000 claims 2
- UYAWSMUOLFSNGC-UHFFFAOYSA-N 3-methyl-4-nitropyridine Chemical class CC1=CN=CC=C1[N+]([O-])=O UYAWSMUOLFSNGC-UHFFFAOYSA-N 0.000 claims 2
- UCSSSFIDQWXJKQ-UHFFFAOYSA-N 3-phenylsulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=CN=C2C=1SC1=CC=CC=C1 UCSSSFIDQWXJKQ-UHFFFAOYSA-N 0.000 claims 2
- JLNRJMGYBKMDGI-UHFFFAOYSA-N 4-methyl-3-nitropyridine Chemical class CC1=CC=NC=C1[N+]([O-])=O JLNRJMGYBKMDGI-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 102000005403 Casein Kinases Human genes 0.000 claims 2
- 108010031425 Casein Kinases Proteins 0.000 claims 2
- 208000020401 Depressive disease Diseases 0.000 claims 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical group C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 2
- 239000011707 mineral Substances 0.000 claims 2
- 235000006408 oxalic acid Nutrition 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical group [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims 2
- LFVFHTBHAIVNJQ-UHFFFAOYSA-N 1-fluoro-3-[(3-fluorophenyl)disulfanyl]benzene Chemical compound FC1=CC=CC(SSC=2C=C(F)C=CC=2)=C1 LFVFHTBHAIVNJQ-UHFFFAOYSA-N 0.000 claims 1
- ISBDSGVMDHZWPJ-UHFFFAOYSA-N 1-methyl-3-phenylsulfanylpyrrolo[3,2-b]pyridine-2-carboxylic acid Chemical compound C12=NC=CC=C2N(C)C(C(O)=O)=C1SC1=CC=CC=C1 ISBDSGVMDHZWPJ-UHFFFAOYSA-N 0.000 claims 1
- SNKVEHPJTUSJBI-UHFFFAOYSA-N 1h-pyrrolo[3,2-c]pyridine-2-carboxamide Chemical class N1=CC=C2NC(C(=O)N)=CC2=C1 SNKVEHPJTUSJBI-UHFFFAOYSA-N 0.000 claims 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical group CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims 1
- UUOLETYDNTVQDY-UHFFFAOYSA-N 2-chloro-3-nitropyridine Chemical class [O-][N+](=O)C1=CC=CN=C1Cl UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 claims 1
- YWKOQHYDYDDVPN-UHFFFAOYSA-N 3-(2,3-dichlorophenyl)sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=CN=C2C=1SC1=CC=CC(Cl)=C1Cl YWKOQHYDYDDVPN-UHFFFAOYSA-N 0.000 claims 1
- VWYQRAUQJGFDOC-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=CN=C2C=1SC1=CC=C(Cl)C=C1Cl VWYQRAUQJGFDOC-UHFFFAOYSA-N 0.000 claims 1
- CVXFVFFTDIDKMR-UHFFFAOYSA-N 3-(2,5-dichlorophenyl)sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=CN=C2C=1SC1=CC(Cl)=CC=C1Cl CVXFVFFTDIDKMR-UHFFFAOYSA-N 0.000 claims 1
- NDWHOVXLAAVAQD-UHFFFAOYSA-N 3-(2-aminophenyl)sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=CN=C2C=1SC1=CC=CC=C1N NDWHOVXLAAVAQD-UHFFFAOYSA-N 0.000 claims 1
- KPQWHAWIISMSID-UHFFFAOYSA-N 3-(2-chlorophenyl)sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=CN=C2C=1SC1=CC=CC=C1Cl KPQWHAWIISMSID-UHFFFAOYSA-N 0.000 claims 1
- HANDTQUUPKYCNC-UHFFFAOYSA-N 3-(2-fluorophenyl)sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=CN=C2C=1SC1=CC=CC=C1F HANDTQUUPKYCNC-UHFFFAOYSA-N 0.000 claims 1
- DGYNCLAVHQNDFX-UHFFFAOYSA-N 3-(2-methoxyphenyl)sulfanyl-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid Chemical compound COC1=CC=CC=C1SC1=C(C(O)=O)NC2=CN=CC=C12 DGYNCLAVHQNDFX-UHFFFAOYSA-N 0.000 claims 1
- PURKCEFVKSMJCP-UHFFFAOYSA-N 3-(2-methoxyphenyl)sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound COC1=CC=CC=C1SC1=C(C(N)=O)NC2=CC=CN=C12 PURKCEFVKSMJCP-UHFFFAOYSA-N 0.000 claims 1
- HSZLOQTXWHDCKG-UHFFFAOYSA-N 3-(2-methylphenyl)sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound CC1=CC=CC=C1SC1=C(C(N)=O)NC2=CC=CN=C12 HSZLOQTXWHDCKG-UHFFFAOYSA-N 0.000 claims 1
- HIEWUKJLGNWKHS-UHFFFAOYSA-N 3-(3,5-dimethylphenyl)sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound CC1=CC(C)=CC(SC=2C3=NC=CC=C3NC=2C(N)=O)=C1 HIEWUKJLGNWKHS-UHFFFAOYSA-N 0.000 claims 1
- NYQJKQGRRPEHDN-UHFFFAOYSA-N 3-(3-aminophenyl)sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=CN=C2C=1SC1=CC=CC(N)=C1 NYQJKQGRRPEHDN-UHFFFAOYSA-N 0.000 claims 1
- NVGOKIIXJLWHFJ-UHFFFAOYSA-N 3-(3-bromophenyl)sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=CN=C2C=1SC1=CC=CC(Br)=C1 NVGOKIIXJLWHFJ-UHFFFAOYSA-N 0.000 claims 1
- OWNOTORBPJLYRT-UHFFFAOYSA-N 3-(3-chlorophenyl)sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=CN=C2C=1SC1=CC=CC(Cl)=C1 OWNOTORBPJLYRT-UHFFFAOYSA-N 0.000 claims 1
- ZGOWLIXZICGZAW-UHFFFAOYSA-N 3-(3-nitrophenyl)sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=CN=C2C=1SC1=CC=CC([N+]([O-])=O)=C1 ZGOWLIXZICGZAW-UHFFFAOYSA-N 0.000 claims 1
- ZLOLVRGUPOFKNJ-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=CN=C2C=1SC1=CC=C(Cl)C=C1 ZLOLVRGUPOFKNJ-UHFFFAOYSA-N 0.000 claims 1
- KSTCBWVRLUMJOB-UHFFFAOYSA-N 3-(4-methylphenyl)sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound C1=CC(C)=CC=C1SC1=C(C(N)=O)NC2=CC=CN=C12 KSTCBWVRLUMJOB-UHFFFAOYSA-N 0.000 claims 1
- RJBYPIMNVSRIQZ-UHFFFAOYSA-N 3-(4-nitrophenyl)sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=CN=C2C=1SC1=CC=C([N+]([O-])=O)C=C1 RJBYPIMNVSRIQZ-UHFFFAOYSA-N 0.000 claims 1
- MFLJGAOJTLNMIC-UHFFFAOYSA-N 3-[2-(trifluoromethyl)phenyl]sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=CN=C2C=1SC1=CC=CC=C1C(F)(F)F MFLJGAOJTLNMIC-UHFFFAOYSA-N 0.000 claims 1
- TWVFZTPEPBZPBE-UHFFFAOYSA-N 3-[3-(trifluoromethoxy)phenyl]sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=CN=C2C=1SC1=CC=CC(OC(F)(F)F)=C1 TWVFZTPEPBZPBE-UHFFFAOYSA-N 0.000 claims 1
- YULJEFFBOLJWHI-UHFFFAOYSA-N 3-[3-(trifluoromethyl)phenyl]sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=CN=C2C=1SC1=CC=CC(C(F)(F)F)=C1 YULJEFFBOLJWHI-UHFFFAOYSA-N 0.000 claims 1
- CWLVEHGKYCYAIO-UHFFFAOYSA-N 3-chloro-4-nitropyridine Chemical class [O-][N+](=O)C1=CC=NC=C1Cl CWLVEHGKYCYAIO-UHFFFAOYSA-N 0.000 claims 1
- PYLCWRVGQLHZAY-UHFFFAOYSA-N 3-phenylsulfanyl-1-propylpyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound C12=NC=CC=C2N(CCC)C(C(N)=O)=C1SC1=CC=CC=C1 PYLCWRVGQLHZAY-UHFFFAOYSA-N 0.000 claims 1
- BWLRYVQQOVVLMK-UHFFFAOYSA-N 3-phenylsulfanyl-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CN=CC=C2C=1SC1=CC=CC=C1 BWLRYVQQOVVLMK-UHFFFAOYSA-N 0.000 claims 1
- HDOWUEDLJPUHDS-UHFFFAOYSA-N 3-phenylsulfanyl-1h-pyrrolo[3,2-c]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=NC=C2C=1SC1=CC=CC=C1 HDOWUEDLJPUHDS-UHFFFAOYSA-N 0.000 claims 1
- LDVBCWIPAFIDQD-UHFFFAOYSA-N 3-quinolin-8-ylsulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound C1=CN=C2C(SC=3C4=NC=CC=C4NC=3C(=O)N)=CC=CC2=C1 LDVBCWIPAFIDQD-UHFFFAOYSA-N 0.000 claims 1
- WVJUNBPWFWXQBE-UHFFFAOYSA-N 3-thiophen-2-ylsulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=CN=C2C=1SC1=CC=CS1 WVJUNBPWFWXQBE-UHFFFAOYSA-N 0.000 claims 1
- JOTRPRKONYTVBV-UHFFFAOYSA-N 4-chloro-3-nitropyridine Chemical class [O-][N+](=O)C1=CN=CC=C1Cl JOTRPRKONYTVBV-UHFFFAOYSA-N 0.000 claims 1
- HGTMKNVMPHBVIT-UHFFFAOYSA-N 5-methoxy-3-(3-methoxyphenyl)sulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound COC1=CC=CC(SC=2C3=NC(OC)=CC=C3NC=2C(N)=O)=C1 HGTMKNVMPHBVIT-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 208000028683 bipolar I disease Diseases 0.000 claims 1
- 208000022257 bipolar II disease Diseases 0.000 claims 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical group [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims 1
- 229910000024 caesium carbonate Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000006114 decarboxylation reaction Methods 0.000 claims 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical group CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- YAYJXRMXYNVMQQ-UHFFFAOYSA-N ethyl 2-hydroxy-3-(3-nitropyridin-2-yl)prop-2-enoate Chemical compound CCOC(=O)C(O)=CC1=NC=CC=C1[N+]([O-])=O YAYJXRMXYNVMQQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 208000024714 major depressive disease Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- NVTLAZCKNMOJAA-UHFFFAOYSA-N n,1-dimethyl-3-phenylsulfanylpyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound C12=NC=CC=C2N(C)C(C(=O)NC)=C1SC1=CC=CC=C1 NVTLAZCKNMOJAA-UHFFFAOYSA-N 0.000 claims 1
- BFRBDJCJDJIIBD-UHFFFAOYSA-N n-methyl-3-phenylsulfanyl-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound CNC(=O)C=1NC2=CC=CN=C2C=1SC1=CC=CC=C1 BFRBDJCJDJIIBD-UHFFFAOYSA-N 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 230000010363 phase shift Effects 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical group [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52876403P | 2003-12-11 | 2003-12-11 | |
| PCT/US2004/040080 WO2005061498A1 (en) | 2003-12-11 | 2004-12-01 | Substituted 1h-pyrrolo[3,2-b, 3,2-c, and 2,3-c]pyridine-2-carboxamides and related analogs as inhibitors of casein kinase i epsilon |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20090380T1 true HRP20090380T1 (hr) | 2009-08-31 |
Family
ID=34710096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20090380T HRP20090380T1 (hr) | 2003-12-11 | 2009-07-03 | SUPSTITUIRANI 1H-PIROLO[3,2-b, 3,2-c, i 2,3-c]PIRIDIN-2-KARBOKSAMIDI I SRODNI ANALOZI KAO INHIBITORI KAZEIN-KINAZE Iε |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US7402672B2 (sr) |
| EP (1) | EP1747220B1 (sr) |
| JP (1) | JP4691506B2 (sr) |
| KR (1) | KR20060113754A (sr) |
| CN (1) | CN100439367C (sr) |
| AT (1) | ATE428711T1 (sr) |
| AU (1) | AU2004303826A1 (sr) |
| BR (1) | BRPI0417520A (sr) |
| CA (1) | CA2549183A1 (sr) |
| DE (1) | DE602004020685D1 (sr) |
| DK (1) | DK1747220T3 (sr) |
| ES (1) | ES2324871T3 (sr) |
| HK (1) | HK1098742A1 (sr) |
| HR (1) | HRP20090380T1 (sr) |
| IL (1) | IL175875A0 (sr) |
| PL (1) | PL1747220T3 (sr) |
| PT (1) | PT1747220E (sr) |
| RS (1) | RS50823B (sr) |
| SI (1) | SI1747220T1 (sr) |
| TW (1) | TW200530234A (sr) |
| WO (1) | WO2005061498A1 (sr) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JO2629B1 (en) * | 2004-08-19 | 2012-06-24 | افينتيس فارما سوتيكالز انك | Branched carboxylic acid amides containing thienobirol, carboxylic acid amides containing pyrolithiazole, and the like as kinase inhibitors casein epsilon |
| SI1791537T1 (sl) * | 2004-08-19 | 2010-02-26 | Aventis Pharma Inc | 3-ariltioindol-2-karboksamidni derivati in njihovi analogi kot inhibitorji kazein-kinaze I |
| JO2724B1 (en) | 2004-08-19 | 2013-09-15 | افينتس فارماسوتيكالز انك | 3-Alternative-5 -6-Amino Alkyl Indole-2-Carboxyl Acid Amide and Related Isotopes as Casein Kinase Inhibitors |
| CN101305010A (zh) * | 2005-09-01 | 2008-11-12 | 阿雷生物药品公司 | Raf抑制剂化合物及其用法 |
| WO2007048065A2 (en) * | 2005-10-21 | 2007-04-26 | Exelixis, Inc. | Pyrimidinones as casein kinase ii (ck2) modulators |
| FR2918061B1 (fr) | 2007-06-28 | 2010-10-22 | Sanofi Aventis | Derives de 6-cycloamino-3-(pyridin-4-yl)imidazo°1,2-b!- pyridazine,leur preparation et leur application en therapeutique. |
| FR2918986B1 (fr) | 2007-07-19 | 2009-09-04 | Sanofi Aventis Sa | Derives de 6-cycloamino-3-(pyridazin-4-yl)imidazo[1,2-b]- pyridazine, leur preparation et leur application en therapeutique |
| FR2939134A1 (fr) | 2008-12-01 | 2010-06-04 | Sanofi Aventis | 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 |
| FR2940285A1 (fr) | 2008-12-19 | 2010-06-25 | Sanofi Aventis | Derives de 6-cycloamino-2-thienyl-3-(pyridin-4-yl)imidazo °1,2-b!-pyridazine et 6-cycloamino-2-furanyl-3- (pyridin-4-yl)imidazo°1,2-b!-pyridazine, leur preparation et leur application en therapeutique |
| FR2940284B1 (fr) | 2008-12-19 | 2011-02-18 | Sanofi Aventis | Derives de 6-cycloamino-2,3-di-pyridinyl-imidazo°1,2-b!- pyridazine,leur preparation et leur application en therapeutique |
| FR2945289A1 (fr) | 2009-05-11 | 2010-11-12 | Sanofi Aventis | Derives de 2-cycloamino-5-(pyridin-4-yl)imidazo°2,1-b! °1,3,4!thiadiazole, leur preparation et leur application en therapeutique |
| SI2493876T1 (sl) * | 2009-10-28 | 2014-04-30 | Pfizer Inc. | Derivati imidazola kot inhibitorji kazein-kinaze |
| FR2960876B1 (fr) | 2010-06-03 | 2012-07-27 | Sanofi Aventis | Derives de 3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1h)-dicarboxamide leur preparation et leur application en therapeutique. |
| WO2014111871A1 (en) | 2013-01-17 | 2014-07-24 | Aurigene Discovery Technologies Limited | 4,5-dihydroisoxazole derivatives as nampt inhibitors |
| WO2014182033A1 (en) * | 2013-05-08 | 2014-11-13 | Yuhan Corporation | Process for the preparation of pyrrolo[2,3-c]pyridine derivatives or pharmaceutically acceptable salts thereof |
| KR101657599B1 (ko) * | 2013-05-20 | 2016-09-19 | 주식회사유한양행 | 피롤로[2,3-c]피리딘 유도체 또는 이의 약학적으로 허용가능한 염의 제조방법 |
| UY35834A (es) * | 2013-11-14 | 2015-05-29 | Bristol Myers Squibb Company Una Corporación Del Estado De Delaware | Piperazinas de pirazolo sustituido como inhibidores de caseína quinasa 1 delta y epsilon |
| CN104945313A (zh) * | 2015-06-19 | 2015-09-30 | 洪帅金 | 一种2-甲基-3-溴吡啶的制备方法 |
| CN104974082A (zh) * | 2015-07-26 | 2015-10-14 | 陈吉美 | 一种2-甲基-4-溴吡啶的制备方法 |
| CN105198802A (zh) * | 2015-11-03 | 2015-12-30 | 江苏梦得电镀化学品有限公司 | 一种2-甲基-3-溴吡啶的制备方法 |
| US10973820B2 (en) | 2017-12-13 | 2021-04-13 | Facio Intellectual Property B.V. | Compounds for treatment of diseases related to DUX4 expression |
| TW202112368A (zh) | 2019-06-13 | 2021-04-01 | 荷蘭商法西歐知識產權股份有限公司 | 用於治療有關dux4表現之疾病的抑制劑組合 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4675332A (en) * | 1984-12-10 | 1987-06-23 | Warner-Lambert Company | Acidic tetrazolyl substituted indole compounds and their use as antiallergy agents |
| US5527819A (en) | 1991-09-06 | 1996-06-18 | Merck & Co., Inc. | Inhibitors of HIV reverse transcriptase |
| WO1994019321A1 (en) * | 1993-02-24 | 1994-09-01 | Merck & Co., Inc. | Inhibitors of hiv reverse transcriptase |
| EP0763035A4 (en) | 1994-06-09 | 1997-10-01 | Smithkline Beecham Corp | ENDOTHELIN RECEPTOR ANTAGONISTS |
| US5977134A (en) | 1996-12-05 | 1999-11-02 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| US6432989B1 (en) * | 1999-08-27 | 2002-08-13 | Pfizer Inc | Use of CRF antagonists to treat circadian rhythm disorders |
| GEP20063814B (en) | 2001-10-02 | 2006-05-10 | Upjohn Co | Azabicyclic-Substituted Fused-Heteroaryl Compounds for Treatment of DiseaseAzabicyclic-Substituted Fused-Heteroaryl Compounds for Treatment of Disease |
| AU2003220190A1 (en) | 2002-03-13 | 2003-09-29 | Pharmacia & Upjohn Company Llc | Pyrazolo(1,5-a)pyridine derivatives as neurotransmitter modulators |
| AU2003226724A1 (en) * | 2002-03-27 | 2003-10-08 | Glaxo Group Limited | Quinoline and aza-indole derivatives and their use as 5-ht6 ligands |
-
2004
- 2004-12-01 CA CA002549183A patent/CA2549183A1/en not_active Abandoned
- 2004-12-01 EP EP04812567A patent/EP1747220B1/en active Active
- 2004-12-01 WO PCT/US2004/040080 patent/WO2005061498A1/en active Application Filing
- 2004-12-01 DE DE602004020685T patent/DE602004020685D1/de active Active
- 2004-12-01 AT AT04812567T patent/ATE428711T1/de not_active IP Right Cessation
- 2004-12-01 CN CNB200480040577XA patent/CN100439367C/zh not_active Expired - Fee Related
- 2004-12-01 PL PL04812567T patent/PL1747220T3/pl unknown
- 2004-12-01 AU AU2004303826A patent/AU2004303826A1/en not_active Abandoned
- 2004-12-01 RS RSP-2009/0302A patent/RS50823B/sr unknown
- 2004-12-01 DK DK04812567T patent/DK1747220T3/da active
- 2004-12-01 US US11/001,533 patent/US7402672B2/en active Active
- 2004-12-01 ES ES04812567T patent/ES2324871T3/es active Active
- 2004-12-01 JP JP2006543873A patent/JP4691506B2/ja not_active Expired - Fee Related
- 2004-12-01 PT PT04812567T patent/PT1747220E/pt unknown
- 2004-12-01 BR BRPI0417520-4A patent/BRPI0417520A/pt not_active IP Right Cessation
- 2004-12-01 SI SI200431149T patent/SI1747220T1/sl unknown
- 2004-12-01 KR KR1020067013455A patent/KR20060113754A/ko not_active Application Discontinuation
- 2004-12-10 TW TW093138220A patent/TW200530234A/zh unknown
-
2006
- 2006-05-23 IL IL175875A patent/IL175875A0/en unknown
-
2007
- 2007-05-15 HK HK07105112.5A patent/HK1098742A1/xx not_active IP Right Cessation
-
2008
- 2008-04-21 US US12/106,681 patent/US7626027B2/en active Active
-
2009
- 2009-07-03 HR HR20090380T patent/HRP20090380T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US7402672B2 (en) | 2008-07-22 |
| EP1747220B1 (en) | 2009-04-15 |
| ES2324871T3 (es) | 2009-08-18 |
| JP2007513950A (ja) | 2007-05-31 |
| PT1747220E (pt) | 2009-07-08 |
| PL1747220T3 (pl) | 2009-09-30 |
| WO2005061498A1 (en) | 2005-07-07 |
| DE602004020685D1 (de) | 2009-05-28 |
| CN1906194A (zh) | 2007-01-31 |
| HK1098742A1 (en) | 2007-07-27 |
| US20080200496A1 (en) | 2008-08-21 |
| KR20060113754A (ko) | 2006-11-02 |
| RS50823B (sr) | 2010-08-31 |
| DK1747220T3 (da) | 2009-08-10 |
| TW200530234A (en) | 2005-09-16 |
| BRPI0417520A (pt) | 2007-03-06 |
| US20050131012A1 (en) | 2005-06-16 |
| JP4691506B2 (ja) | 2011-06-01 |
| CN100439367C (zh) | 2008-12-03 |
| AU2004303826A1 (en) | 2005-07-07 |
| CA2549183A1 (en) | 2005-07-07 |
| IL175875A0 (en) | 2006-10-05 |
| ATE428711T1 (de) | 2009-05-15 |
| EP1747220A1 (en) | 2007-01-31 |
| SI1747220T1 (sl) | 2009-08-31 |
| US7626027B2 (en) | 2009-12-01 |
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