RU2009101911A - Производные пиридина и пиразина в качестве ингибиторов mnk-киназы - Google Patents
Производные пиридина и пиразина в качестве ингибиторов mnk-киназы Download PDFInfo
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- RU2009101911A RU2009101911A RU2009101911/04A RU2009101911A RU2009101911A RU 2009101911 A RU2009101911 A RU 2009101911A RU 2009101911/04 A RU2009101911/04 A RU 2009101911/04A RU 2009101911 A RU2009101911 A RU 2009101911A RU 2009101911 A RU2009101911 A RU 2009101911A
- Authority
- RU
- Russia
- Prior art keywords
- pyrazin
- alkyl
- indol
- amino
- amine
- Prior art date
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title 2
- 229940043355 kinase inhibitor Drugs 0.000 title 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
- 150000003216 pyrazines Chemical class 0.000 title 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 28
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 24
- -1 aminocarbonylphenyl Chemical group 0.000 claims abstract 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 12
- 239000000651 prodrug Substances 0.000 claims abstract 12
- 229940002612 prodrug Drugs 0.000 claims abstract 12
- 150000003839 salts Chemical class 0.000 claims abstract 12
- 125000001424 substituent group Chemical group 0.000 claims abstract 12
- 150000001204 N-oxides Chemical class 0.000 claims abstract 11
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims abstract 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 8
- 125000005843 halogen group Chemical group 0.000 claims abstract 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 6
- 150000004677 hydrates Chemical class 0.000 claims abstract 5
- 230000003287 optical effect Effects 0.000 claims abstract 5
- 125000002252 acyl group Chemical group 0.000 claims abstract 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 4
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims abstract 4
- 125000001041 indolyl group Chemical group 0.000 claims abstract 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract 3
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims abstract 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract 3
- 125000001544 thienyl group Chemical group 0.000 claims abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 76
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 208000008589 Obesity Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 230000004968 inflammatory condition Effects 0.000 claims 4
- 235000020824 obesity Nutrition 0.000 claims 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 4
- 206010006895 Cachexia Diseases 0.000 claims 3
- 208000032928 Dyslipidaemia Diseases 0.000 claims 3
- 208000030814 Eating disease Diseases 0.000 claims 3
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 3
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 3
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 3
- 206010020772 Hypertension Diseases 0.000 claims 3
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 3
- 102100026299 MAP kinase-interacting serine/threonine-protein kinase 1 Human genes 0.000 claims 3
- 101710139011 MAP kinase-interacting serine/threonine-protein kinase 1 Proteins 0.000 claims 3
- 102100033610 MAP kinase-interacting serine/threonine-protein kinase 2 Human genes 0.000 claims 3
- 101710138999 MAP kinase-interacting serine/threonine-protein kinase 2 Proteins 0.000 claims 3
- 208000029078 coronary artery disease Diseases 0.000 claims 3
- 206010012601 diabetes mellitus Diseases 0.000 claims 3
- 235000014632 disordered eating Nutrition 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 201000001421 hyperglycemia Diseases 0.000 claims 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims 3
- 201000008482 osteoarthritis Diseases 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 3
- 201000002859 sleep apnea Diseases 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 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 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 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 2
- VEFWZQFPBUSMBL-UHFFFAOYSA-N [4-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxyphenyl]-morpholin-4-ylmethanone Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2NC3=CC=CC=C3C=2)C(OC)=CC=1C(=O)N1CCOCC1 VEFWZQFPBUSMBL-UHFFFAOYSA-N 0.000 claims 2
- 201000001883 cholelithiasis Diseases 0.000 claims 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- IPBNVTMTIKJPSK-UHFFFAOYSA-N (3-aminoazetidin-1-yl)-[4-[[6-(5-fluoro-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=C(F)C=C3C=2)C(OC)=CC=1C(=O)N1CC(N)C1 IPBNVTMTIKJPSK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- XITUAKFNJMJXQZ-UHFFFAOYSA-N (4-methyl-1,4-diazepan-1-yl)-[6-[[6-(1h-pyrrolo[3,2-c]pyridin-2-yl)pyrazin-2-yl]amino]pyridin-3-yl]methanone Chemical compound C1CN(C)CCCN1C(=O)C(C=N1)=CC=C1NC1=CN=CC(C=2NC3=CC=NC=C3C=2)=N1 XITUAKFNJMJXQZ-UHFFFAOYSA-N 0.000 claims 1
- SCCCDOPYCXBGPY-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-[[6-(1h-pyrrolo[2,3-c]pyridin-2-yl)pyrazin-2-yl]amino]phenyl]methanone Chemical compound C1CN(C)CCN1C(=O)C(C=C1)=CC=C1NC1=CN=CC(C=2NC3=CN=CC=C3C=2)=N1 SCCCDOPYCXBGPY-UHFFFAOYSA-N 0.000 claims 1
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 1
- XCUZPVBDBASDCD-UHFFFAOYSA-N 2,9-diazaspiro[4.5]decan-2-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)N(C1)CCC21CCCNC2 XCUZPVBDBASDCD-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- RZLKZEGKUUMPDQ-UHFFFAOYSA-N 3-methoxy-4-[[6-(4-methoxy-1h-indol-2-yl)pyrazin-2-yl]amino]-n-methyl-n-(1-methylpyrrolidin-3-yl)benzamide Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2NC3=CC=CC(OC)=C3C=2)C(OC)=CC=1C(=O)N(C)C1CCN(C)C1 RZLKZEGKUUMPDQ-UHFFFAOYSA-N 0.000 claims 1
- OVSTYTDVQDWUBE-UHFFFAOYSA-N 3-methoxy-4-[[6-(5-methoxy-1h-indol-2-yl)pyrazin-2-yl]amino]-n-methyl-n-(1-methylpyrrolidin-3-yl)benzamide Chemical compound C=1C2=CC(OC)=CC=C2NC=1C(N=1)=CN=CC=1NC(C(=C1)OC)=CC=C1C(=O)N(C)C1CCN(C)C1 OVSTYTDVQDWUBE-UHFFFAOYSA-N 0.000 claims 1
- UNUXUUBNCRXUMH-UHFFFAOYSA-N 3-methoxy-n-methyl-4-[[6-(5-methyl-1h-indol-2-yl)pyrazin-2-yl]amino]-n-(1-methylpyrrolidin-3-yl)benzamide Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2NC3=CC=C(C)C=C3C=2)C(OC)=CC=1C(=O)N(C)C1CCN(C)C1 UNUXUUBNCRXUMH-UHFFFAOYSA-N 0.000 claims 1
- XMTXOOYCGUDHQX-UHFFFAOYSA-N 3-methoxy-n-methyl-4-[[6-(6-methyl-1h-indol-2-yl)pyrazin-2-yl]amino]-n-(1-methylpyrrolidin-3-yl)benzamide Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2NC3=CC(C)=CC=C3C=2)C(OC)=CC=1C(=O)N(C)C1CCN(C)C1 XMTXOOYCGUDHQX-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- YDYGKLHXQAFPOD-QGZVFWFLSA-N 4-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxy-n-[(3r)-pyrrolidin-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@@H]1CCNC1 YDYGKLHXQAFPOD-QGZVFWFLSA-N 0.000 claims 1
- YDYGKLHXQAFPOD-KRWDZBQOSA-N 4-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxy-n-[(3s)-pyrrolidin-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@H]1CCNC1 YDYGKLHXQAFPOD-KRWDZBQOSA-N 0.000 claims 1
- ZRZOSUIBWQOEGM-UHFFFAOYSA-N 4-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxy-n-piperidin-3-ylbenzamide Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2NC3=CC=CC=C3C=2)C(OC)=CC=1C(=O)NC1CCCNC1 ZRZOSUIBWQOEGM-UHFFFAOYSA-N 0.000 claims 1
- JEUURUVLROAREY-UHFFFAOYSA-N 4-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1NC1=CN=CC(C=2NC3=CC=CC=C3C=2)=N1 JEUURUVLROAREY-UHFFFAOYSA-N 0.000 claims 1
- CGPRHVRLWRCWJA-UHFFFAOYSA-N 4-[[6-(4-fluoro-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(F)=C3C=2)C(OC)=CC=1C(=O)N(C)C1CCN(C)C1 CGPRHVRLWRCWJA-UHFFFAOYSA-N 0.000 claims 1
- ZJPPAUXADIFCJC-UHFFFAOYSA-N 4-[[6-(5-chloro-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=C(Cl)C=C3C=2)C(OC)=CC=1C(=O)N(C)C1CCN(C)C1 ZJPPAUXADIFCJC-UHFFFAOYSA-N 0.000 claims 1
- NWLPGLSOMDEYCD-UHFFFAOYSA-N 4-[[6-(5-fluoro-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=C(F)C=C3C=2)C(OC)=CC=1C(=O)N(C)C1CCN(C)C1 NWLPGLSOMDEYCD-UHFFFAOYSA-N 0.000 claims 1
- GBTXJILKTQBTQO-UHFFFAOYSA-N 4-[[6-(6-chloro-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(Cl)=CC=C3C=2)C(OC)=CC=1C(=O)N(C)C1CCN(C)C1 GBTXJILKTQBTQO-UHFFFAOYSA-N 0.000 claims 1
- KFNNXOYZKPSREJ-UHFFFAOYSA-N 4-[[6-(6-fluoro-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(F)=CC=C3C=2)C(OC)=CC=1C(=O)N(C)C1CCN(C)C1 KFNNXOYZKPSREJ-UHFFFAOYSA-N 0.000 claims 1
- QDBWBNDBUKEGSC-UHFFFAOYSA-N 4-[[6-(7-fluoro-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=C(F)C=CC=C3C=2)C(OC)=CC=1C(=O)N(C)C1CCN(C)C1 QDBWBNDBUKEGSC-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 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 1
- VMGFCBXBANWBPC-LJQANCHMSA-N [(3r)-3-(dimethylamino)pyrrolidin-1-yl]-[3-methoxy-4-[[6-(6-methoxy-1h-indol-2-yl)pyrazin-2-yl]amino]phenyl]methanone Chemical compound N1C2=CC(OC)=CC=C2C=C1C(N=1)=CN=CC=1NC(C(=C1)OC)=CC=C1C(=O)N1CC[C@@H](N(C)C)C1 VMGFCBXBANWBPC-LJQANCHMSA-N 0.000 claims 1
- AHAWPPZIBXCDSQ-HXUWFJFHSA-N [(3r)-3-(dimethylamino)pyrrolidin-1-yl]-[4-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]phenyl]methanone Chemical compound C1[C@H](N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC1=CN=CC(C=2NC3=CC=CC=C3C=2)=N1 AHAWPPZIBXCDSQ-HXUWFJFHSA-N 0.000 claims 1
- YSJOQWCLLYPLTQ-QGZVFWFLSA-N [(3r)-3-aminopyrrolidin-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)N1CC[C@@H](N)C1 YSJOQWCLLYPLTQ-QGZVFWFLSA-N 0.000 claims 1
- ONYIMVNCXQKHJT-QGZVFWFLSA-N [(3r)-3-aminopyrrolidin-1-yl]-[4-[[6-(5-fluoro-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=C(F)C=C3C=2)C(OC)=CC=1C(=O)N1CC[C@@H](N)C1 ONYIMVNCXQKHJT-QGZVFWFLSA-N 0.000 claims 1
- 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 1
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- UGOJBVXTCWYKAB-UHFFFAOYSA-N n-(2-hydroxyethyl)-4-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCO)=CC=C1NC1=CN=CC(C=2NC3=CC=CC=C3C=2)=N1 UGOJBVXTCWYKAB-UHFFFAOYSA-N 0.000 claims 1
- PSFHIIUZBHXNOR-UHFFFAOYSA-N n-(azetidin-3-yl)-4-[[6-(5-fluoro-1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxybenzamide Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2NC3=CC=C(F)C=C3C=2)C(OC)=CC=1C(=O)NC1CNC1 PSFHIIUZBHXNOR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- GLWMBNCIIMAGKE-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-4-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCN(CC)CC)=CC=C1NC1=CN=CC(C=2NC3=CC=CC=C3C=2)=N1 GLWMBNCIIMAGKE-UHFFFAOYSA-N 0.000 claims 1
- TUNJGJAVESBYRU-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-4-[[6-(5-fluoro-1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCN(CC)CC)=CC=C1NC1=CN=CC(C=2NC3=CC=C(F)C=C3C=2)=N1 TUNJGJAVESBYRU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- JWJMWQRKAQBITG-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-4-[6-(1h-indol-2-yl)pyrazin-2-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)N(C)CCCN(C)C)=CC=C1C1=CN=CC(C=2NC3=CC=CC=C3C=2)=N1 JWJMWQRKAQBITG-UHFFFAOYSA-N 0.000 claims 1
- VTNHHYGXQQBHGX-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-4-[[6-(1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NCCCN(C)C)=CC=C1NC1=CN=CC(C=2NC3=CC=CC=C3C=2)=N1 VTNHHYGXQQBHGX-UHFFFAOYSA-N 0.000 claims 1
- KRAFXUXYGUZYOZ-UHFFFAOYSA-N n-ethyl-n-(2-hydroxyethyl)-4-[6-(1h-indol-2-yl)pyrazin-2-yl]benzamide Chemical compound C1=CC(C(=O)N(CCO)CC)=CC=C1C1=CN=CC(C=2NC3=CC=CC=C3C=2)=N1 KRAFXUXYGUZYOZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 claims 1
- BPRBMHIBHVTUIE-UHFFFAOYSA-N tert-butyl 3-[[4-[[6-(5-fluoro-1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxybenzoyl]amino]azetidine-1-carboxylate Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2NC3=CC=C(F)C=C3C=2)C(OC)=CC=1C(=O)NC1CN(C(=O)OC(C)(C)C)C1 BPRBMHIBHVTUIE-UHFFFAOYSA-N 0.000 claims 1
- IHYDKONBGFJEEL-UHFFFAOYSA-N tert-butyl 3-[[[4-[6-(1h-indol-2-yl)pyrazin-2-yl]benzoyl]amino]methyl]piperidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC1CNC(=O)C1=CC=C(C=2N=C(C=NC=2)C=2NC3=CC=CC=C3C=2)C=C1 IHYDKONBGFJEEL-UHFFFAOYSA-N 0.000 claims 1
- YDUPFVYOLHJSGF-UHFFFAOYSA-N tert-butyl n-[1-[4-[[6-(5-fluoro-1h-indol-2-yl)pyrazin-2-yl]amino]-3-methoxybenzoyl]azetidin-3-yl]carbamate Chemical compound C=1C=C(NC=2N=C(C=NC=2)C=2NC3=CC=C(F)C=C3C=2)C(OC)=CC=1C(=O)N1CC(NC(=O)OC(C)(C)C)C1 YDUPFVYOLHJSGF-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Child & Adolescent Psychology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0601379.1 | 2006-06-22 | ||
| SE0601379 | 2006-06-22 | ||
| US85006706P | 2006-10-06 | 2006-10-06 | |
| US60/850,067 | 2006-10-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2009101911A true RU2009101911A (ru) | 2010-07-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2009101911/04A RU2009101911A (ru) | 2006-06-22 | 2007-06-21 | Производные пиридина и пиразина в качестве ингибиторов mnk-киназы |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20080039450A1 (https=) |
| EP (1) | EP2044051B1 (https=) |
| JP (1) | JP2009541268A (https=) |
| CN (1) | CN101472912A (https=) |
| AT (1) | ATE456565T1 (https=) |
| AU (1) | AU2007263017A1 (https=) |
| BR (1) | BRPI0713328A2 (https=) |
| CA (1) | CA2654358A1 (https=) |
| DE (1) | DE602007004618D1 (https=) |
| ES (1) | ES2340093T3 (https=) |
| RU (1) | RU2009101911A (https=) |
| WO (1) | WO2007147874A1 (https=) |
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| EP1889847A1 (en) | 2006-07-10 | 2008-02-20 | DeveloGen Aktiengesellschaft | Pyrrolopyrimidines for pharmaceutical compositions |
| GB0625659D0 (en) | 2006-12-21 | 2007-01-31 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| JP5603770B2 (ja) | 2007-05-31 | 2014-10-08 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｃｒ２受容体拮抗薬およびその使用 |
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| WO2009065596A2 (en) * | 2007-11-22 | 2009-05-28 | Develogen Aktiengesellschaft | Use of mnk inhibitors for the treatment of alzheimer's disease |
| EP2265270A1 (en) * | 2008-02-04 | 2010-12-29 | OSI Pharmaceuticals, Inc. | 2-aminopyridine kinase inhibitors |
| EA014100B1 (ru) * | 2008-02-21 | 2010-08-30 | Общество С Ограниченной Ответственностью "Валексфарм" | Производные 2,4-диаминопиридина, фармацевтическая композиция, лекарственное средство на их основе для лечения или предупреждения заболеваний и нарушений, вызванных гиперактивацией nmda-рецепторов и/или в качестве стимуляторов когнитивных функций и способ лечения |
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| JP5575274B2 (ja) | 2010-02-26 | 2014-08-20 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 医薬組成物のためのｍｎｋｌ／ｍｎｋ２阻害活性を有する４−［シクロアルキルオキシ（ヘテロ）アリールアミノ］チエノ「２，３−ｄ］ピリミジン |
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| US5459266A (en) * | 1994-02-04 | 1995-10-17 | Hoechst Celanese Corporation | Substituted pyrazines |
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| CN101472912A (zh) | 2009-07-01 |
| ES2340093T3 (es) | 2010-05-28 |
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| WO2007147874A1 (en) | 2007-12-27 |
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