JP2009541268A - Mnkキナーゼ阻害剤としてのピリジンおよびピラジン誘導体 - Google Patents
Mnkキナーゼ阻害剤としてのピリジンおよびピラジン誘導体 Download PDFInfo
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- JP2009541268A JP2009541268A JP2009515885A JP2009515885A JP2009541268A JP 2009541268 A JP2009541268 A JP 2009541268A JP 2009515885 A JP2009515885 A JP 2009515885A JP 2009515885 A JP2009515885 A JP 2009515885A JP 2009541268 A JP2009541268 A JP 2009541268A
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- Prior art keywords
- pyrazin
- alkyl
- indol
- amino
- mmol
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 6
- 150000003216 pyrazines Chemical class 0.000 title description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title description 2
- 229940043355 kinase inhibitor Drugs 0.000 title 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 262
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 49
- 208000035475 disorder Diseases 0.000 claims abstract description 43
- 101710139011 MAP kinase-interacting serine/threonine-protein kinase 1 Proteins 0.000 claims abstract description 42
- 102100026299 MAP kinase-interacting serine/threonine-protein kinase 1 Human genes 0.000 claims abstract description 42
- 238000011282 treatment Methods 0.000 claims abstract description 42
- 230000000694 effects Effects 0.000 claims abstract description 31
- 101710138999 MAP kinase-interacting serine/threonine-protein kinase 2 Proteins 0.000 claims abstract description 30
- 102100033610 MAP kinase-interacting serine/threonine-protein kinase 2 Human genes 0.000 claims abstract description 30
- 230000002265 prevention Effects 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 9
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 3
- -1 aminocarbonylphenyl Chemical group 0.000 claims description 283
- 238000000034 method Methods 0.000 claims description 229
- 125000000217 alkyl group Chemical group 0.000 claims description 189
- 125000000623 heterocyclic group Chemical group 0.000 claims description 71
- 150000003839 salts Chemical class 0.000 claims description 55
- 229910052757 nitrogen Inorganic materials 0.000 claims description 50
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 33
- 206010028980 Neoplasm Diseases 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 25
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000000651 prodrug Chemical group 0.000 claims description 22
- 229940002612 prodrug Drugs 0.000 claims description 22
- 125000001041 indolyl group Chemical group 0.000 claims description 19
- 201000011510 cancer Diseases 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 16
- 150000001204 N-oxides Chemical group 0.000 claims description 15
- 208000008589 Obesity Diseases 0.000 claims description 15
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 206010012601 diabetes mellitus Diseases 0.000 claims description 15
- 230000004968 inflammatory condition Effects 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- 235000020824 obesity Nutrition 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 230000003287 optical effect Effects 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims description 9
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 201000008482 osteoarthritis Diseases 0.000 claims description 9
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 8
- 201000001421 hyperglycemia Diseases 0.000 claims description 8
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 206010006895 Cachexia Diseases 0.000 claims description 7
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 7
- 208000030814 Eating disease Diseases 0.000 claims description 7
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 7
- 206010020772 Hypertension Diseases 0.000 claims description 7
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 7
- 201000001883 cholelithiasis Diseases 0.000 claims description 7
- 208000029078 coronary artery disease Diseases 0.000 claims description 7
- 235000014632 disordered eating Nutrition 0.000 claims description 7
- 208000001130 gallstones Diseases 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 201000002859 sleep apnea Diseases 0.000 claims description 7
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 6
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 5
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 230000037396 body weight Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 3
- PNZKKQWBSPXAPD-UHFFFAOYSA-N 4-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxy-n-methyl-n-(1-methylpyrrolidin-3-yl)benzamide Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2NC3=CC=CC=C3C=2)C(OC)=CC=1C(=O)N(C)C1CCN(C)C1 PNZKKQWBSPXAPD-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- NCJJBSPRMXVTIW-UHFFFAOYSA-N (4-ethylpiperazin-1-yl)-[4-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxyphenyl]methanone Chemical compound C1CN(CC)CCN1C(=O)C(C=C1OC)=CC=C1NC1=CN=CC(C=2NC3=CC=CC=C3C=2)=N1 NCJJBSPRMXVTIW-UHFFFAOYSA-N 0.000 claims description 2
- JNQRUUBGEMDSNI-UHFFFAOYSA-N (4-ethylpiperazin-1-yl)-[6-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]pyridin-3-yl]methanone Chemical compound C1CN(CC)CCN1C(=O)C(C=N1)=CC=C1NC1=CN=CC(C=2NC3=CC=CC=C3C=2)=N1 JNQRUUBGEMDSNI-UHFFFAOYSA-N 0.000 claims description 2
- PHLZSOMVNDLFQN-UHFFFAOYSA-N 2-[2-[[6-(5-fluoro-1h-indol-2-yl)pyrazin-2-yl]amino]-5-(4-methylpiperazine-1-carbonyl)phenoxy]-n,n-dimethylacetamide Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2NC3=CC=C(F)C=C3C=2)C(OCC(=O)N(C)C)=CC=1C(=O)N1CCN(C)CC1 PHLZSOMVNDLFQN-UHFFFAOYSA-N 0.000 claims description 2
- GMDXKZWRGGYIIL-UHFFFAOYSA-N 2-[6-[4-(4-methylpiperazine-1-carbonyl)anilino]pyrazin-2-yl]-1h-indole-5-carboxamide Chemical compound C1CN(C)CCN1C(=O)C(C=C1)=CC=C1NC1=CN=CC(C=2NC3=CC=C(C=C3C=2)C(N)=O)=N1 GMDXKZWRGGYIIL-UHFFFAOYSA-N 0.000 claims description 2
- DPHUNMBXCBPBOC-UHFFFAOYSA-N 3-[[6-(1-benzofuran-2-yl)pyrazin-2-yl]amino]-4-methoxy-n-methyl-n-(1-methylpyrrolidin-3-yl)benzamide Chemical compound C1=C(NC=2N=C(C=NC=2)C=2OC3=CC=CC=C3C=2)C(OC)=CC=C1C(=O)N(C)C1CCN(C)C1 DPHUNMBXCBPBOC-UHFFFAOYSA-N 0.000 claims description 2
- ZHRBUSCAJPHBJY-UHFFFAOYSA-N 3-chloro-n-[2-(diethylamino)ethyl]-4-[[6-(5-fluoro-1h-indol-2-yl)pyrazin-2-yl]amino]benzamide Chemical compound ClC1=CC(C(=O)NCCN(CC)CC)=CC=C1NC1=CN=CC(C=2NC3=CC=C(F)C=C3C=2)=N1 ZHRBUSCAJPHBJY-UHFFFAOYSA-N 0.000 claims description 2
- ANESEZVJTLJYQN-UHFFFAOYSA-N 3-fluoro-4-[6-(6-fluoro-1h-indol-2-yl)pyrazin-2-yl]-n-methyl-n-(1-methylpyrrolidin-3-yl)benzamide Chemical compound C=1C=C(C=2N=C(C=NC=2)C=2NC3=CC(F)=CC=C3C=2)C(F)=CC=1C(=O)N(C)C1CCN(C)C1 ANESEZVJTLJYQN-UHFFFAOYSA-N 0.000 claims description 2
- PKUBWSRLUOHNPZ-UHFFFAOYSA-N 3-fluoro-5-[6-(6-fluoro-1h-indol-2-yl)pyrazin-2-yl]-n-methyl-n-(1-methylpyrrolidin-3-yl)benzamide Chemical compound C=1C(F)=CC(C=2N=C(C=NC=2)C=2NC3=CC(F)=CC=C3C=2)=CC=1C(=O)N(C)C1CCN(C)C1 PKUBWSRLUOHNPZ-UHFFFAOYSA-N 0.000 claims description 2
- OGSUUHVBRCGZAU-UHFFFAOYSA-N 4-[5-amino-6-(1-benzofuran-2-yl)pyrazin-2-yl]-n-(2,3-dihydroxypropyl)benzamide Chemical compound N1=C(C=2OC3=CC=CC=C3C=2)C(N)=NC=C1C1=CC=C(C(=O)NCC(O)CO)C=C1 OGSUUHVBRCGZAU-UHFFFAOYSA-N 0.000 claims description 2
- OGSUUHVBRCGZAU-INIZCTEOSA-N 4-[5-amino-6-(1-benzofuran-2-yl)pyrazin-2-yl]-n-[(2s)-2,3-dihydroxypropyl]benzamide Chemical compound N1=C(C=2OC3=CC=CC=C3C=2)C(N)=NC=C1C1=CC=C(C(=O)NC[C@H](O)CO)C=C1 OGSUUHVBRCGZAU-INIZCTEOSA-N 0.000 claims description 2
- HJANIWAXHMBUSG-UHFFFAOYSA-N 4-[5-amino-6-(1-benzofuran-2-yl)pyrazin-2-yl]-n-[3-[bis(2-hydroxyethyl)amino]propyl]benzamide Chemical compound N1=C(C=2OC3=CC=CC=C3C=2)C(N)=NC=C1C1=CC=C(C(=O)NCCCN(CCO)CCO)C=C1 HJANIWAXHMBUSG-UHFFFAOYSA-N 0.000 claims description 2
- LANXWFYAJDTUQO-UHFFFAOYSA-N 4-[5-amino-6-(1-benzofuran-2-yl)pyrazin-2-yl]-n-ethyl-n-(2-hydroxyethyl)benzamide Chemical compound C1=CC(C(=O)N(CCO)CC)=CC=C1C1=CN=C(N)C(C=2OC3=CC=CC=C3C=2)=N1 LANXWFYAJDTUQO-UHFFFAOYSA-N 0.000 claims description 2
- FANHFMGLTLDNKK-UHFFFAOYSA-N 4-[[6-(1-benzofuran-2-yl)pyrazin-2-yl]amino]-3-methoxy-n-methyl-n-(1-methylpyrrolidin-3-yl)benzamide Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2OC3=CC=CC=C3C=2)C(OC)=CC=1C(=O)N(C)C1CCN(C)C1 FANHFMGLTLDNKK-UHFFFAOYSA-N 0.000 claims description 2
- RCOTZFFXLPZDMS-GOSISDBHSA-N [(3r)-3-(dimethylamino)pyrrolidin-1-yl]-[3-methoxy-4-[[6-(1h-pyrrolo[3,2-c]pyridin-2-yl)pyrazin-2-yl]amino]phenyl]methanone Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2NC3=CC=NC=C3C=2)C(OC)=CC=1C(=O)N1CC[C@@H](N(C)C)C1 RCOTZFFXLPZDMS-GOSISDBHSA-N 0.000 claims description 2
- XLWQOGPOLMFUFI-CALCHBBNSA-N [(3r,5s)-3,5-dimethylpiperazin-1-yl]-[4-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxyphenyl]methanone Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2NC3=CC=CC=C3C=2)C(OC)=CC=1C(=O)N1C[C@H](C)N[C@H](C)C1 XLWQOGPOLMFUFI-CALCHBBNSA-N 0.000 claims description 2
- UOUOLDXTLRBHQM-UHFFFAOYSA-N [3-(2-ethoxyethoxy)-4-[[6-(5-fluoro-1h-indol-2-yl)pyrazin-2-yl]amino]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2NC3=CC=C(F)C=C3C=2)C(OCCOCC)=CC=1C(=O)N1CCN(C)CC1 UOUOLDXTLRBHQM-UHFFFAOYSA-N 0.000 claims description 2
- LHFZSYIZPPCJQA-UHFFFAOYSA-N [3-(dimethylamino)pyrrolidin-1-yl]-[4-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxyphenyl]methanone Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2NC3=CC=CC=C3C=2)C(OC)=CC=1C(=O)N1CCC(N(C)C)C1 LHFZSYIZPPCJQA-UHFFFAOYSA-N 0.000 claims description 2
- YVCKXRKFCLDWNJ-UHFFFAOYSA-N [3-[2-(dimethylamino)ethoxy]-4-[[6-(5-fluoro-1h-indol-2-yl)pyrazin-2-yl]amino]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2NC3=CC=C(F)C=C3C=2)C(OCCN(C)C)=CC=1C(=O)N1CCN(C)CC1 YVCKXRKFCLDWNJ-UHFFFAOYSA-N 0.000 claims description 2
- KUIRMWHHKSNSTJ-UHFFFAOYSA-N [3-methoxy-4-[[6-(6-methoxy-1h-indol-2-yl)pyrazin-2-yl]amino]phenyl]-piperazin-1-ylmethanone Chemical compound N1C2=CC(OC)=CC=C2C=C1C(N=1)=CN=CC=1NC(C(=C1)OC)=CC=C1C(=O)N1CCNCC1 KUIRMWHHKSNSTJ-UHFFFAOYSA-N 0.000 claims description 2
- NQSJRTIBZZCLEA-UHFFFAOYSA-N [4-[2-(dimethylamino)ethyl]piperazin-1-yl]-[3-fluoro-5-[6-(6-fluoro-1h-indol-2-yl)pyrazin-2-yl]phenyl]methanone Chemical compound C1CN(CCN(C)C)CCN1C(=O)C1=CC(F)=CC(C=2N=C(C=NC=2)C=2NC3=CC(F)=CC=C3C=2)=C1 NQSJRTIBZZCLEA-UHFFFAOYSA-N 0.000 claims description 2
- DIGCBNOQNHBISN-UHFFFAOYSA-N [4-[5-amino-6-(1-benzofuran-2-yl)pyrazin-2-yl]-3-fluorophenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2N=C(C(N)=NC=2)C=2OC3=CC=CC=C3C=2)C(F)=C1 DIGCBNOQNHBISN-UHFFFAOYSA-N 0.000 claims description 2
- IBEJZHNMZAVULE-UHFFFAOYSA-N [4-[6-(5-fluoro-1h-indol-2-yl)pyrazin-2-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2N=C(C=NC=2)C=2NC3=CC=C(F)C=C3C=2)C=C1 IBEJZHNMZAVULE-UHFFFAOYSA-N 0.000 claims description 2
- VYTBTGLIMYZDAJ-UHFFFAOYSA-N [4-[[5-(5-fluoro-1h-indol-2-yl)pyridin-3-yl]amino]phenyl]-piperazin-1-ylmethanone Chemical compound C=1C2=CC(F)=CC=C2NC=1C(C=1)=CN=CC=1NC(C=C1)=CC=C1C(=O)N1CCNCC1 VYTBTGLIMYZDAJ-UHFFFAOYSA-N 0.000 claims description 2
- JHLYSHJWXMJURV-UHFFFAOYSA-N [4-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxyphenyl]-(4-methyl-1,4-diazepan-1-yl)methanone Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2NC3=CC=CC=C3C=2)C(OC)=CC=1C(=O)N1CCCN(C)CC1 JHLYSHJWXMJURV-UHFFFAOYSA-N 0.000 claims description 2
- ICDZULFHPSAEPS-UHFFFAOYSA-N [4-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxyphenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2NC3=CC=CC=C3C=2)C(OC)=CC=1C(=O)N1CCN(C(C)C)CC1 ICDZULFHPSAEPS-UHFFFAOYSA-N 0.000 claims description 2
- HYNJDSXEWIFBRF-UHFFFAOYSA-N [4-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxyphenyl]-[4-(2-methoxyethyl)piperazin-1-yl]methanone Chemical compound C1CN(CCOC)CCN1C(=O)C(C=C1OC)=CC=C1NC1=CN=CC(C=2NC3=CC=CC=C3C=2)=N1 HYNJDSXEWIFBRF-UHFFFAOYSA-N 0.000 claims description 2
- CMTPWEJEADPAFJ-OAHLLOKOSA-N [4-[[6-(5-fluoro-1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxyphenyl]-[(3r)-3-methylpiperazin-1-yl]methanone Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2NC3=CC=C(F)C=C3C=2)C(OC)=CC=1C(=O)N1CCN[C@H](C)C1 CMTPWEJEADPAFJ-OAHLLOKOSA-N 0.000 claims description 2
- CMTPWEJEADPAFJ-HNNXBMFYSA-N [4-[[6-(5-fluoro-1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxyphenyl]-[(3s)-3-methylpiperazin-1-yl]methanone Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2NC3=CC=C(F)C=C3C=2)C(OC)=CC=1C(=O)N1CCN[C@@H](C)C1 CMTPWEJEADPAFJ-HNNXBMFYSA-N 0.000 claims description 2
- BDAFYQPNCMBBGU-UHFFFAOYSA-N [5-[[5-(5-fluoro-1h-indol-2-yl)pyridin-3-yl]amino]pyridin-2-yl]-piperazin-1-ylmethanone Chemical compound C=1C2=CC(F)=CC=C2NC=1C(C=1)=CN=CC=1NC(C=N1)=CC=C1C(=O)N1CCNCC1 BDAFYQPNCMBBGU-UHFFFAOYSA-N 0.000 claims description 2
- VNHSDZLHPCFUJV-UHFFFAOYSA-N [6-[[5-(5-fluoro-1h-indol-2-yl)pyridin-3-yl]amino]pyridin-3-yl]-piperazin-1-ylmethanone Chemical compound C=1C2=CC(F)=CC=C2NC=1C(C=1)=CN=CC=1NC(N=C1)=CC=C1C(=O)N1CCNCC1 VNHSDZLHPCFUJV-UHFFFAOYSA-N 0.000 claims description 2
- UONRFQNJFBKWEB-UHFFFAOYSA-N [6-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]pyridin-3-yl]-(4-methyl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C)CCCN1C(=O)C(C=N1)=CC=C1NC1=CN=CC(C=2NC3=CC=CC=C3C=2)=N1 UONRFQNJFBKWEB-UHFFFAOYSA-N 0.000 claims description 2
- FLHZZIIHBLTSNH-UHFFFAOYSA-N [6-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]pyridin-3-yl]-morpholin-4-ylmethanone Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2NC3=CC=CC=C3C=2)N=CC=1C(=O)N1CCOCC1 FLHZZIIHBLTSNH-UHFFFAOYSA-N 0.000 claims description 2
- FVKBASVXAYEXPY-UHFFFAOYSA-N acetic acid;4-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]benzamide Chemical compound CC(O)=O.C1=CC(C(=O)N)=CC=C1NC1=CN=CC(C=2NC3=CC=CC=C3C=2)=N1 FVKBASVXAYEXPY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- FQNVEWSIRAAFDY-UHFFFAOYSA-N n-(2,3-dihydroxypropyl)-4-[6-(1h-indol-2-yl)pyrazin-2-yl]benzamide Chemical compound C1=CC(C(=O)NCC(O)CO)=CC=C1C1=CN=CC(C=2NC3=CC=CC=C3C=2)=N1 FQNVEWSIRAAFDY-UHFFFAOYSA-N 0.000 claims description 2
- FQNVEWSIRAAFDY-KRWDZBQOSA-N n-[(2s)-2,3-dihydroxypropyl]-4-[6-(1h-indol-2-yl)pyrazin-2-yl]benzamide Chemical compound C1=CC(C(=O)NC[C@H](O)CO)=CC=C1C1=CN=CC(C=2NC3=CC=CC=C3C=2)=N1 FQNVEWSIRAAFDY-KRWDZBQOSA-N 0.000 claims description 2
- ULIMCJSUTRFRIF-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-2-fluoro-4-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]benzamide Chemical compound C1=C(F)C(C(=O)NCCN(CC)CC)=CC=C1NC1=CN=CC(C=2NC3=CC=CC=C3C=2)=N1 ULIMCJSUTRFRIF-UHFFFAOYSA-N 0.000 claims description 2
- QFDRBXUQNMKNAH-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-4-[5-(1h-indol-2-yl)pyridin-3-yl]benzamide Chemical compound C1=CC(C(=O)NCCN(CC)CC)=CC=C1C1=CN=CC(C=2NC3=CC=CC=C3C=2)=C1 QFDRBXUQNMKNAH-UHFFFAOYSA-N 0.000 claims description 2
- QEHZTXHMFSBBQW-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxy-n-methylbenzamide Chemical compound COC1=CC(C(=O)N(C)CCN(C)C)=CC=C1NC1=CN=CC(C=2NC3=CC=CC=C3C=2)=N1 QEHZTXHMFSBBQW-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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| PCT/EP2007/056213 WO2007147874A1 (en) | 2006-06-22 | 2007-06-21 | Pyridine and pyrazine derivatives as mnk kinase inhibitors |
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- 2007-06-21 AT AT07786791T patent/ATE456565T1/de not_active IP Right Cessation
- 2007-06-21 ES ES07786791T patent/ES2340093T3/es active Active
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- 2007-06-21 WO PCT/EP2007/056213 patent/WO2007147874A1/en not_active Ceased
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- 2007-06-21 RU RU2009101911/04A patent/RU2009101911A/ru not_active Application Discontinuation
- 2007-06-21 EP EP07786791A patent/EP2044051B1/en active Active
- 2007-06-21 US US11/821,565 patent/US20080039450A1/en not_active Abandoned
- 2007-06-21 CN CNA200780022963XA patent/CN101472912A/zh active Pending
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2007147874A1 (en) | 2007-12-27 |
| BRPI0713328A2 (pt) | 2012-10-30 |
| RU2009101911A (ru) | 2010-07-27 |
| CN101472912A (zh) | 2009-07-01 |
| ES2340093T3 (es) | 2010-05-28 |
| EP2044051B1 (en) | 2010-01-27 |
| ATE456565T1 (de) | 2010-02-15 |
| US20080039450A1 (en) | 2008-02-14 |
| DE602007004618D1 (de) | 2010-03-18 |
| CA2654358A1 (en) | 2007-12-27 |
| EP2044051A1 (en) | 2009-04-08 |
| AU2007263017A1 (en) | 2007-12-27 |
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