JP2011519845A5 - - Google Patents
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- Publication number
- JP2011519845A5 JP2011519845A5 JP2011506764A JP2011506764A JP2011519845A5 JP 2011519845 A5 JP2011519845 A5 JP 2011519845A5 JP 2011506764 A JP2011506764 A JP 2011506764A JP 2011506764 A JP2011506764 A JP 2011506764A JP 2011519845 A5 JP2011519845 A5 JP 2011519845A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- ethyl
- alkyl
- ylmethyl
- pyridin
- 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.)
- Pending
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- 125000003118 aryl group Chemical group 0.000 claims 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 19
- 125000005843 halogen group Chemical group 0.000 claims 15
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 14
- -1 and R 7 is H Chemical group 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 11
- 239000012453 solvate Substances 0.000 claims 11
- 125000001424 substituent group Chemical group 0.000 claims 11
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 9
- 150000001408 amides Chemical class 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 9
- 208000010668 atopic eczema Diseases 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 230000000172 allergic effect Effects 0.000 claims 6
- 208000006673 asthma Diseases 0.000 claims 6
- 125000004429 atom Chemical group 0.000 claims 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 125000002619 bicyclic group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 4
- 101000605522 Homo sapiens Kallikrein-1 Proteins 0.000 claims 4
- 102100038297 Kallikrein-1 Human genes 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 230000000694 effects Effects 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- CWLQUGTUXBXTLF-RXMQYKEDSA-N (2r)-1-methylpyrrolidine-2-carboxylic acid Chemical compound CN1CCC[C@@H]1C(O)=O CWLQUGTUXBXTLF-RXMQYKEDSA-N 0.000 claims 3
- 206010011224 Cough Diseases 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- XQGVQRPSTODODM-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrrole-2-carboxylic acid Chemical compound CC1=CC(C)=C(C(O)=O)N1 XQGVQRPSTODODM-UHFFFAOYSA-N 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- YIVHOQIKHMTVRG-UHFFFAOYSA-N 3-methyl-1h-pyrrole-2-carboxylic acid Chemical compound CC=1C=CNC=1C(O)=O YIVHOQIKHMTVRG-UHFFFAOYSA-N 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 claims 2
- 206010010741 Conjunctivitis Diseases 0.000 claims 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 2
- 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 2
- 230000005713 exacerbation Effects 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 2
- YNXFKYXSWNIWGO-ZCFIWIBFSA-N (2r)-1-ethylpyrrolidin-1-ium-2-carboxylate Chemical compound CCN1CCC[C@@H]1C(O)=O YNXFKYXSWNIWGO-ZCFIWIBFSA-N 0.000 claims 1
- BPSLZWSRHTULGU-ZCFIWIBFSA-N (2r)-1-methylpiperidin-1-ium-2-carboxylate Chemical compound CN1CCCC[C@@H]1C(O)=O BPSLZWSRHTULGU-ZCFIWIBFSA-N 0.000 claims 1
- CKPAOPWAVKSUPQ-SSDOTTSWSA-N (2r)-1-propan-2-ylpyrrolidine-2-carboxylic acid Chemical compound CC(C)N1CCC[C@@H]1C(O)=O CKPAOPWAVKSUPQ-SSDOTTSWSA-N 0.000 claims 1
- GNAPFRRSVAADBO-RBUKOAKNSA-N (2r)-n-[(2s)-1-[(6-amino-2-methylpyridin-3-yl)methylamino]-3-(3,4-difluorophenyl)-1-oxopropan-2-yl]-1-methylpyrrolidine-2-carboxamide Chemical compound CN1CCC[C@@H]1C(=O)N[C@H](C(=O)NCC=1C(=NC(N)=CC=1)C)CC1=CC=C(F)C(F)=C1 GNAPFRRSVAADBO-RBUKOAKNSA-N 0.000 claims 1
- FYNSTMSUSFYEPG-RBUKOAKNSA-N (2r)-n-[(2s)-1-[(6-amino-2-methylpyridin-3-yl)methylamino]-3-(4-fluorophenyl)-1-oxopropan-2-yl]-1-methylpyrrolidine-2-carboxamide Chemical compound CN1CCC[C@@H]1C(=O)N[C@H](C(=O)NCC=1C(=NC(N)=CC=1)C)CC1=CC=C(F)C=C1 FYNSTMSUSFYEPG-RBUKOAKNSA-N 0.000 claims 1
- UMFBAWNSXKASMF-AZUAARDMSA-N (2r)-n-[(2s)-1-[(6-aminopyridin-3-yl)methylamino]-3-(3,4-dichlorophenyl)-1-oxopropan-2-yl]-2-(dimethylamino)-3-methylbutanamide Chemical compound C([C@H](NC(=O)[C@H](N(C)C)C(C)C)C(=O)NCC=1C=NC(N)=CC=1)C1=CC=C(Cl)C(Cl)=C1 UMFBAWNSXKASMF-AZUAARDMSA-N 0.000 claims 1
- LEHQVVNYCNGHJT-BVLLHJTKSA-N (2r)-n-[(2s)-1-[(6-aminopyridin-3-yl)methylamino]-3-(3,4-dichlorophenyl)-1-oxopropan-2-yl]-2-(dimethylamino)-3-methylpentanamide Chemical compound C([C@H](NC(=O)[C@H](N(C)C)C(C)CC)C(=O)NCC=1C=NC(N)=CC=1)C1=CC=C(Cl)C(Cl)=C1 LEHQVVNYCNGHJT-BVLLHJTKSA-N 0.000 claims 1
- SHHYWMRZINUSMU-PKOBYXMFSA-N (2r)-n-[(2s)-1-[(6-aminopyridin-3-yl)methylamino]-3-(3,4-dichlorophenyl)-1-oxopropan-2-yl]-3-methyl-2-(methylamino)butanamide Chemical compound C([C@H](NC(=O)[C@@H](C(C)C)NC)C(=O)NCC=1C=NC(N)=CC=1)C1=CC=C(Cl)C(Cl)=C1 SHHYWMRZINUSMU-PKOBYXMFSA-N 0.000 claims 1
- NURZVDIBMNTJJY-LEWJYISDSA-N (2r)-n-[(2s)-1-[(6-aminopyridin-3-yl)methylamino]-3-(3,4-difluorophenyl)-1-oxopropan-2-yl]-1-(2-methylpropyl)pyrrolidine-2-carboxamide Chemical compound CC(C)CN1CCC[C@@H]1C(=O)N[C@H](C(=O)NCC=1C=NC(N)=CC=1)CC1=CC=C(F)C(F)=C1 NURZVDIBMNTJJY-LEWJYISDSA-N 0.000 claims 1
- ALLYUHIQZKTLFG-RBUKOAKNSA-N (2r)-n-[(2s)-1-[(6-aminopyridin-3-yl)methylamino]-3-(3,4-difluorophenyl)-1-oxopropan-2-yl]-1-ethylpyrrolidine-2-carboxamide Chemical compound CCN1CCC[C@@H]1C(=O)N[C@H](C(=O)NCC=1C=NC(N)=CC=1)CC1=CC=C(F)C(F)=C1 ALLYUHIQZKTLFG-RBUKOAKNSA-N 0.000 claims 1
- HHPHMTXQJOTJOH-RBUKOAKNSA-N (2r)-n-[(2s)-1-[(6-aminopyridin-3-yl)methylamino]-3-(3,4-difluorophenyl)-1-oxopropan-2-yl]-1-methylpiperidine-2-carboxamide Chemical compound CN1CCCC[C@@H]1C(=O)N[C@H](C(=O)NCC=1C=NC(N)=CC=1)CC1=CC=C(F)C(F)=C1 HHPHMTXQJOTJOH-RBUKOAKNSA-N 0.000 claims 1
- KTPJLXCBGUHRNE-ZWKOTPCHSA-N (2r)-n-[(2s)-1-[(6-aminopyridin-3-yl)methylamino]-3-(3,4-difluorophenyl)-1-oxopropan-2-yl]-1-methylpyrrolidine-2-carboxamide Chemical compound CN1CCC[C@@H]1C(=O)N[C@H](C(=O)NCC=1C=NC(N)=CC=1)CC1=CC=C(F)C(F)=C1 KTPJLXCBGUHRNE-ZWKOTPCHSA-N 0.000 claims 1
- CXIOCVHMSFGZQO-VQTJNVASSA-N (2r)-n-[(2s)-1-[(6-aminopyridin-3-yl)methylamino]-3-(3,4-difluorophenyl)-1-oxopropan-2-yl]-1-propan-2-ylpyrrolidine-2-carboxamide Chemical compound CC(C)N1CCC[C@@H]1C(=O)N[C@H](C(=O)NCC=1C=NC(N)=CC=1)CC1=CC=C(F)C(F)=C1 CXIOCVHMSFGZQO-VQTJNVASSA-N 0.000 claims 1
- AMRUBRJGEVHSAQ-VQTJNVASSA-N (2r)-n-[(2s)-1-[(6-aminopyridin-3-yl)methylamino]-3-(3,4-difluorophenyl)-1-oxopropan-2-yl]-1-propylpyrrolidine-2-carboxamide Chemical compound CCCN1CCC[C@@H]1C(=O)N[C@H](C(=O)NCC=1C=NC(N)=CC=1)CC1=CC=C(F)C(F)=C1 AMRUBRJGEVHSAQ-VQTJNVASSA-N 0.000 claims 1
- LTFSFTYAXJRGHD-ICSRJNTNSA-N (2r)-n-[(2s)-1-[(6-aminopyridin-3-yl)methylamino]-3-(3,4-difluorophenyl)-1-oxopropan-2-yl]-2-(dimethylamino)-3,3-dimethylbutanamide Chemical compound C([C@H](NC(=O)[C@H](N(C)C)C(C)(C)C)C(=O)NCC=1C=NC(N)=CC=1)C1=CC=C(F)C(F)=C1 LTFSFTYAXJRGHD-ICSRJNTNSA-N 0.000 claims 1
- OWNPADWBDISBEU-BVLLHJTKSA-N (2r)-n-[(2s)-1-[(6-aminopyridin-3-yl)methylamino]-3-(3,4-difluorophenyl)-1-oxopropan-2-yl]-2-(dimethylamino)-3-methylpentanamide Chemical compound C([C@H](NC(=O)[C@H](N(C)C)C(C)CC)C(=O)NCC=1C=NC(N)=CC=1)C1=CC=C(F)C(F)=C1 OWNPADWBDISBEU-BVLLHJTKSA-N 0.000 claims 1
- FXXBRLOCXFWOAH-UNGYYTSISA-N (2r)-n-[(2s)-1-[(6-aminopyridin-3-yl)methylamino]-3-(3,4-difluorophenyl)-1-oxopropan-2-yl]-3-methyl-2-(methylamino)pentanamide Chemical compound C([C@H](NC(=O)[C@H](NC)C(C)CC)C(=O)NCC=1C=NC(N)=CC=1)C1=CC=C(F)C(F)=C1 FXXBRLOCXFWOAH-UNGYYTSISA-N 0.000 claims 1
- HASSJHSXNCNWET-ZWKOTPCHSA-N (2r)-n-[(2s)-1-[(6-aminopyridin-3-yl)methylamino]-3-(3,5-difluorophenyl)-1-oxopropan-2-yl]-1-methylpyrrolidine-2-carboxamide Chemical compound CN1CCC[C@@H]1C(=O)N[C@H](C(=O)NCC=1C=NC(N)=CC=1)CC1=CC(F)=CC(F)=C1 HASSJHSXNCNWET-ZWKOTPCHSA-N 0.000 claims 1
- QCDLPKNDJUXHPZ-FCHUYYIVSA-N (2r)-n-[(2s)-1-[(6-aminopyridin-3-yl)methylamino]-3-naphthalen-1-yl-1-oxopropan-2-yl]-1-methylpyrrolidine-2-carboxamide Chemical compound CN1CCC[C@@H]1C(=O)N[C@H](C(=O)NCC=1C=NC(N)=CC=1)CC1=CC=CC2=CC=CC=C12 QCDLPKNDJUXHPZ-FCHUYYIVSA-N 0.000 claims 1
- HZKPRLIQYPXMMR-NIIYEGGUSA-N (2s)-3-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-1-yl)-n-[(6-aminopyridin-3-yl)methyl]-2-[[(2s)-2-[methyl(propan-2-yl)amino]propanoyl]amino]propanamide Chemical compound O=C([C@H](CC1C2CCCCC2CCC1)NC(=O)[C@H](C)N(C)C(C)C)NCC1=CC=C(N)N=C1 HZKPRLIQYPXMMR-NIIYEGGUSA-N 0.000 claims 1
- RJBGNRSZHMJIFZ-WIOPSUGQSA-N (2s)-n-[(2r)-1-[(6-aminopyridin-3-yl)methylamino]-3,3-dicyclohexyl-1-oxopropan-2-yl]-1-methylpyrrolidine-2-carboxamide Chemical compound CN1CCC[C@H]1C(=O)N[C@@H](C(=O)NCC=1C=NC(N)=CC=1)C(C1CCCCC1)C1CCCCC1 RJBGNRSZHMJIFZ-WIOPSUGQSA-N 0.000 claims 1
- ZBJBLJBCRBJSOH-LIRRHRJNSA-N (2s)-n-[(6-aminopyridin-3-yl)methyl]-2-[[(2s)-2-(diethylamino)propanoyl]amino]-3-(3,4-difluorophenyl)propanamide Chemical compound C([C@H](NC(=O)[C@H](C)N(CC)CC)C(=O)NCC=1C=NC(N)=CC=1)C1=CC=C(F)C(F)=C1 ZBJBLJBCRBJSOH-LIRRHRJNSA-N 0.000 claims 1
- MVIYPYSWIRIPPB-KXBFYZLASA-N (2s)-n-[(6-aminopyridin-3-yl)methyl]-2-[[(2s)-2-[methyl(propan-2-yl)amino]propanoyl]amino]-3-[3-(trifluoromethyl)phenyl]propanamide Chemical class C([C@H](NC(=O)[C@H](C)N(C)C(C)C)C(=O)NCC=1C=NC(N)=CC=1)C1=CC=CC(C(F)(F)F)=C1 MVIYPYSWIRIPPB-KXBFYZLASA-N 0.000 claims 1
- ZPWQSCXEEDHALT-UGSOOPFHSA-N (2s)-n-[(6-aminopyridin-3-yl)methyl]-3-(3,4-difluorophenyl)-2-[[(2s)-2-[ethyl(methyl)amino]propanoyl]amino]propanamide Chemical compound C([C@H](NC(=O)[C@H](C)N(C)CC)C(=O)NCC=1C=NC(N)=CC=1)C1=CC=C(F)C(F)=C1 ZPWQSCXEEDHALT-UGSOOPFHSA-N 0.000 claims 1
- JOUDXLWHCRZMIA-LIRRHRJNSA-N (2s)-n-[(6-aminopyridin-3-yl)methyl]-3-(3,4-difluorophenyl)-2-[[(2s)-2-[methyl(propan-2-yl)amino]propanoyl]amino]propanamide Chemical compound C([C@H](NC(=O)[C@H](C)N(C)C(C)C)C(=O)NCC=1C=NC(N)=CC=1)C1=CC=C(F)C(F)=C1 JOUDXLWHCRZMIA-LIRRHRJNSA-N 0.000 claims 1
- FNBWXEBZXBEKQV-FQEVSTJZSA-N (2s)-n-[(6-aminopyridin-3-yl)methyl]-3-(3,4-difluorophenyl)-2-[[2-[di(propan-2-yl)amino]acetyl]amino]propanamide Chemical compound C([C@H](NC(=O)CN(C(C)C)C(C)C)C(=O)NCC=1C=NC(N)=CC=1)C1=CC=C(F)C(F)=C1 FNBWXEBZXBEKQV-FQEVSTJZSA-N 0.000 claims 1
- ITCSRFRLSFJJOK-KXBFYZLASA-N (2s)-n-[(6-aminopyridin-3-yl)methyl]-3-(3-chlorophenyl)-2-[[(2s)-2-[methyl(propan-2-yl)amino]propanoyl]amino]propanamide Chemical compound C([C@H](NC(=O)[C@H](C)N(C)C(C)C)C(=O)NCC=1C=NC(N)=CC=1)C1=CC=CC(Cl)=C1 ITCSRFRLSFJJOK-KXBFYZLASA-N 0.000 claims 1
- WESLSKIOXPGDNK-PXNSSMCTSA-N (2s)-n-[(6-aminopyridin-3-yl)methyl]-3-(3-methylphenyl)-2-[[(2s)-2-[methyl(propan-2-yl)amino]propanoyl]amino]propanamide Chemical compound C([C@H](NC(=O)[C@H](C)N(C)C(C)C)C(=O)NCC=1C=NC(N)=CC=1)C1=CC=CC(C)=C1 WESLSKIOXPGDNK-PXNSSMCTSA-N 0.000 claims 1
- SGYFOTNBVHRQND-LPHOPBHVSA-N (2s)-n-[(6-aminopyridin-3-yl)methyl]-3-cyclohexyl-2-[[(2s)-2-(diethylamino)propanoyl]amino]propanamide Chemical compound C([C@H](NC(=O)[C@H](C)N(CC)CC)C(=O)NCC=1C=NC(N)=CC=1)C1CCCCC1 SGYFOTNBVHRQND-LPHOPBHVSA-N 0.000 claims 1
- WBXASMQRJWLSHU-LPHOPBHVSA-N (2s)-n-[(6-aminopyridin-3-yl)methyl]-3-cyclohexyl-2-[[(2s)-2-[methyl(propan-2-yl)amino]propanoyl]amino]propanamide Chemical compound C([C@H](NC(=O)[C@H](C)N(C)C(C)C)C(=O)NCC=1C=NC(N)=CC=1)C1CCCCC1 WBXASMQRJWLSHU-LPHOPBHVSA-N 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000007101 Muscle Cramp Diseases 0.000 claims 1
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- 206010033647 Pancreatitis acute Diseases 0.000 claims 1
- 206010034038 Parotitis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 208000036071 Rhinorrhea Diseases 0.000 claims 1
- 206010039101 Rhinorrhoea Diseases 0.000 claims 1
- 208000005392 Spasm Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 208000024780 Urticaria Diseases 0.000 claims 1
- 201000003229 acute pancreatitis Diseases 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
- 201000003146 cystitis Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- NYQLBDQLKMVFQL-IBGZPJMESA-N n-[(2s)-1-[(6-amino-2-methylpyridin-3-yl)methylamino]-1-oxo-3-[3-(trifluoromethyl)phenyl]propan-2-yl]-3,5-dimethyl-1h-pyrrole-2-carboxamide Chemical compound N1C(C)=CC(C)=C1C(=O)N[C@H](C(=O)NCC=1C(=NC(N)=CC=1)C)CC1=CC=CC(C(F)(F)F)=C1 NYQLBDQLKMVFQL-IBGZPJMESA-N 0.000 claims 1
- JXGILBLBTVTXCP-SFHVURJKSA-N n-[(2s)-1-[(6-aminopyridin-3-yl)methylamino]-3-(3,4-difluorophenyl)-1-oxopropan-2-yl]-3,5-dimethyl-1h-pyrrole-2-carboxamide Chemical compound N1C(C)=CC(C)=C1C(=O)N[C@H](C(=O)NCC=1C=NC(N)=CC=1)CC1=CC=C(F)C(F)=C1 JXGILBLBTVTXCP-SFHVURJKSA-N 0.000 claims 1
- XHGLPPSTJBHYSJ-KRWDZBQOSA-N n-[(2s)-1-[(6-aminopyridin-3-yl)methylamino]-3-(4-fluorophenyl)-1-oxopropan-2-yl]-3-methyl-1h-pyrrole-2-carboxamide Chemical compound C1=CNC(C(=O)N[C@@H](CC=2C=CC(F)=CC=2)C(=O)NCC=2C=NC(N)=CC=2)=C1C XHGLPPSTJBHYSJ-KRWDZBQOSA-N 0.000 claims 1
- 230000001613 neoplastic effect Effects 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 208000028169 periodontal disease Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 229940080818 propionamide Drugs 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 230000000306 recurrent effect Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 201000009890 sinusitis Diseases 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 210000002460 smooth muscle Anatomy 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7143108P | 2008-04-29 | 2008-04-29 | |
| US61/071,431 | 2008-04-29 | ||
| GB0807828.9 | 2008-04-29 | ||
| GBGB0807828.9A GB0807828D0 (en) | 2008-04-29 | 2008-04-29 | Aminopyridine derivatives |
| PCT/GB2009/001062 WO2009133348A1 (en) | 2008-04-29 | 2009-04-28 | Aminopyridine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011519845A JP2011519845A (ja) | 2011-07-14 |
| JP2011519845A5 true JP2011519845A5 (enExample) | 2012-06-21 |
Family
ID=39522782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011506764A Pending JP2011519845A (ja) | 2008-04-29 | 2009-04-28 | アミノピリジン誘導体 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US20100076015A1 (enExample) |
| EP (1) | EP2300428A1 (enExample) |
| JP (1) | JP2011519845A (enExample) |
| KR (1) | KR20110014161A (enExample) |
| CN (1) | CN102076666A (enExample) |
| AR (1) | AR071514A1 (enExample) |
| AU (1) | AU2009241906A1 (enExample) |
| BR (1) | BRPI0911443A2 (enExample) |
| CA (1) | CA2722648A1 (enExample) |
| CO (1) | CO6321287A2 (enExample) |
| EC (1) | ECSP10010648A (enExample) |
| GB (1) | GB0807828D0 (enExample) |
| IL (1) | IL208812A0 (enExample) |
| MX (1) | MX2010011896A (enExample) |
| NZ (1) | NZ588635A (enExample) |
| RU (1) | RU2010148420A (enExample) |
| WO (1) | WO2009133348A1 (enExample) |
| ZA (1) | ZA201007615B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8211933B2 (en) * | 2008-12-12 | 2012-07-03 | Vanderbilt University | 3.3.0 bicyclic GlyT1 inhibitors and methods of making and using same |
| GB0918922D0 (en) * | 2009-10-28 | 2009-12-16 | Vantia Ltd | Aminopyridine derivatives |
| US9290485B2 (en) | 2010-08-04 | 2016-03-22 | Novartis Ag | N-((6-amino-pyridin-3-yl)methyl)-heteroaryl-carboxamides |
| KR20190068537A (ko) * | 2016-09-18 | 2019-06-18 | 에이치 리 모피트 캔서 센터 앤드 리서어치 인스티튜트 아이엔씨 | Yap1과 oct4의 상호작용을 표적으로 하는 yap1 저해제 |
| EP3765015A4 (en) | 2018-03-14 | 2021-12-15 | H. Lee Moffitt Cancer Center & Research Institute, Inc. | YAP1 INHIBITORS AGAINST INTERACTION OF YAP1 WITH OCT4 |
| BR112022001054A2 (pt) * | 2019-08-21 | 2022-03-15 | Kalvista Pharmaceuticals Ltd | Inibidores enzimáticos |
| EP4066896A4 (en) * | 2019-11-27 | 2024-03-27 | Riken | G9A INHIBITOR |
| WO2022255399A1 (ja) * | 2021-06-01 | 2022-12-08 | 国立研究開発法人理化学研究所 | Ｇ９ａ阻害剤 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5187157A (en) * | 1987-06-05 | 1993-02-16 | Du Pont Merck Pharmaceutical Company | Peptide boronic acid inhibitors of trypsin-like proteases |
| SE9301916D0 (sv) * | 1993-06-03 | 1993-06-03 | Ab Astra | New peptides derivatives |
| US5464820A (en) * | 1993-06-22 | 1995-11-07 | The University Hospital | Specific inhibitors of tissue kallikrein |
| CA2387002A1 (en) * | 2000-08-11 | 2002-02-21 | Wilex Ag | Non-covalent inhibitors of urokinase and blood vessel formation |
| FR2819254B1 (fr) * | 2001-01-08 | 2003-04-18 | Fournier Lab Sa | Nouveaux composes de la n-(phenylsulfonyl) glycine, leur procede de preparation et leur utilisation pour obtenir des compostions pharmaceutiques |
| FR2836143B1 (fr) * | 2002-02-21 | 2004-04-16 | Servier Lab | Nouveaux derives d'acides amines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| ATE423114T1 (de) * | 2004-03-02 | 2009-03-15 | Merck & Co Inc | Aminocyclopropancarbonsäureamidderivate als bradykininantagonisten |
| WO2005095327A1 (ja) * | 2004-03-31 | 2005-10-13 | Ajinomoto Co., Inc. | アニリン誘導体 |
-
2008
- 2008-04-29 GB GBGB0807828.9A patent/GB0807828D0/en not_active Ceased
-
2009
- 2009-04-28 AR ARP090101507A patent/AR071514A1/es unknown
- 2009-04-28 BR BRPI0911443A patent/BRPI0911443A2/pt not_active IP Right Cessation
- 2009-04-28 MX MX2010011896A patent/MX2010011896A/es not_active Application Discontinuation
- 2009-04-28 US US12/431,114 patent/US20100076015A1/en not_active Abandoned
- 2009-04-28 EP EP09738378A patent/EP2300428A1/en not_active Withdrawn
- 2009-04-28 WO PCT/GB2009/001062 patent/WO2009133348A1/en not_active Ceased
- 2009-04-28 RU RU2010148420/04A patent/RU2010148420A/ru unknown
- 2009-04-28 CA CA2722648A patent/CA2722648A1/en not_active Abandoned
- 2009-04-28 CN CN2009801248942A patent/CN102076666A/zh active Pending
- 2009-04-28 AU AU2009241906A patent/AU2009241906A1/en not_active Abandoned
- 2009-04-28 NZ NZ588635A patent/NZ588635A/en not_active IP Right Cessation
- 2009-04-28 JP JP2011506764A patent/JP2011519845A/ja active Pending
- 2009-04-28 KR KR1020107026578A patent/KR20110014161A/ko not_active Withdrawn
-
2010
- 2010-10-19 IL IL208812A patent/IL208812A0/en unknown
- 2010-10-25 CO CO10132210A patent/CO6321287A2/es not_active Application Discontinuation
- 2010-10-25 ZA ZA2010/07615A patent/ZA201007615B/en unknown
- 2010-11-29 EC EC2010010648A patent/ECSP10010648A/es unknown
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