JP2012528137A5 - - Google Patents
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- Publication number
- JP2012528137A5 JP2012528137A5 JP2012512460A JP2012512460A JP2012528137A5 JP 2012528137 A5 JP2012528137 A5 JP 2012528137A5 JP 2012512460 A JP2012512460 A JP 2012512460A JP 2012512460 A JP2012512460 A JP 2012512460A JP 2012528137 A5 JP2012528137 A5 JP 2012528137A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- trifluoromethyl
- naphthyridine
- dihydro
- thiazol
- 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.)
- Withdrawn
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- -1 ethoxy, 2-hydroxyethoxy, 3-hydroxypropoxy, 2- (phosphonooxy) ethoxy, 3- (phosphonooxy) propoxy Chemical group 0.000 claims 62
- 125000000217 alkyl group Chemical group 0.000 claims 29
- 229910052757 nitrogen Inorganic materials 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 15
- 125000000623 heterocyclic group Chemical group 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 239000003937 drug carrier Substances 0.000 claims 5
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 125000001589 carboacyl group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 2
- 125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 claims 2
- BAJLKMACPVPZNQ-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1N=C2N(CCN(C)C)C=C(C(O)=O)C(=O)C2=CC=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 BAJLKMACPVPZNQ-UHFFFAOYSA-N 0.000 claims 2
- URAMULVRCIAJRC-UHFFFAOYSA-N 1-[2-bis(phenylmethoxy)phosphoryloxyethyl]-6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1N=C2N(CCOP(=O)(OCC=3C=CC=CC=3)OCC=3C=CC=CC=3)C=C(C(O)=O)C(=O)C2=CC=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 URAMULVRCIAJRC-UHFFFAOYSA-N 0.000 claims 2
- NLCXMONEGIXREO-UHFFFAOYSA-N 1-cyclopropyl-6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1N=C2N(C3CC3)C=C(C(O)=O)C(=O)C2=CC=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 NLCXMONEGIXREO-UHFFFAOYSA-N 0.000 claims 2
- CECKJGPQMZHHIK-UHFFFAOYSA-N 6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-1-(2-hydroxyethyl)-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1N=C2N(CCO)C=C(C(O)=O)C(=O)C2=CC=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 CECKJGPQMZHHIK-UHFFFAOYSA-N 0.000 claims 2
- HCPJGEUZSXSUHH-LJQANCHMSA-N 6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-1-[(2s)-1-hydroxy-3,3-dimethylbutan-2-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1N=C2N([C@H](CO)C(C)(C)C)C=C(C(O)=O)C(=O)C2=CC=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 HCPJGEUZSXSUHH-LJQANCHMSA-N 0.000 claims 2
- QHLZWIWFSMJXMM-HNNXBMFYSA-N 6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-1-[(2s)-1-hydroxy-4-methylpentan-2-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1N=C2N([C@H](CO)CC(C)C)C=C(C(O)=O)C(=O)C2=CC=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 QHLZWIWFSMJXMM-HNNXBMFYSA-N 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 2
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- YNYRDWYDHXJRAC-UHFFFAOYSA-N 1-(1,3-dimethoxypropan-2-yl)-6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1N=C2N(C(COC)COC)C=C(C(O)=O)C(=O)C2=CC=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 YNYRDWYDHXJRAC-UHFFFAOYSA-N 0.000 claims 1
- RTNSHAKISNYKQM-HXUWFJFHSA-N 1-[(3r)-1-[2-(diethylamino)ethyl]piperidin-3-yl]-6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1N=C2N([C@H]3CN(CCN(CC)CC)CCC3)C=C(C(O)=O)C(=O)C2=CC=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 RTNSHAKISNYKQM-HXUWFJFHSA-N 0.000 claims 1
- CGRBQXWGSFRQGM-SANMLTNESA-N 1-[(3s)-1-[2-(diethylamino)ethyl]piperidin-3-yl]-6-[6-(ethylcarbamoylamino)-4-(4-phenyl-1,3-thiazol-2-yl)pyridin-3-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1N=C2N([C@@H]3CN(CCN(CC)CC)CCC3)C=C(C(O)=O)C(=O)C2=CC=1C=1C=NC(NC(=O)NCC)=CC=1C(SC=1)=NC=1C1=CC=CC=C1 CGRBQXWGSFRQGM-SANMLTNESA-N 0.000 claims 1
- FQFBADRCHPFUCT-VWLOTQADSA-N 1-[(3s)-1-[2-(diethylamino)ethyl]piperidin-3-yl]-6-[6-(ethylcarbamoylamino)-4-[4-(2-methylpropyl)-1,3-thiazol-2-yl]pyridin-3-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1N=C2N([C@@H]3CN(CCN(CC)CC)CCC3)C=C(C(O)=O)C(=O)C2=CC=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(CC(C)C)=CS1 FQFBADRCHPFUCT-VWLOTQADSA-N 0.000 claims 1
- HCQLUTGBFHXDRD-UHFFFAOYSA-N 1-ethyl-6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1N=C2N(CC)C=C(C(O)=O)C(=O)C2=CC=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 HCQLUTGBFHXDRD-UHFFFAOYSA-N 0.000 claims 1
- SRKZSOACNVAPFX-UHFFFAOYSA-N 1-ethyl-6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-7-(4-methylpiperazin-1-yl)-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1C(C(C(C(O)=O)=CN2CC)=O)=C2N=C(N2CCN(C)CC2)C=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 SRKZSOACNVAPFX-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- HQHIZVBASMKPNG-UHFFFAOYSA-N 6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-1-(2-morpholin-4-ylethyl)-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1N=C2N(CCN3CCOCC3)C=C(C(O)=O)C(=O)C2=CC=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 HQHIZVBASMKPNG-UHFFFAOYSA-N 0.000 claims 1
- MSCUOSCXSHWYIS-QFIPXVFZSA-N 6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-1-[(2s)-1-[hydroxy(phenylmethoxy)phosphoryl]oxy-4-methylpentan-2-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1N=C2N([C@H](COP(O)(=O)OCC=3C=CC=CC=3)CC(C)C)C=C(C(O)=O)C(=O)C2=CC=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 MSCUOSCXSHWYIS-QFIPXVFZSA-N 0.000 claims 1
- LILMGFVNUNQSLC-HSZRJFAPSA-N 6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-1-[(2s)-1-hydroxy-3,3-dimethylbutan-2-yl]-7-(4-methylpiperazin-1-yl)-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1C(C(C(C(O)=O)=CN2[C@H](CO)C(C)(C)C)=O)=C2N=C(N2CCN(C)CC2)C=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 LILMGFVNUNQSLC-HSZRJFAPSA-N 0.000 claims 1
- AYGKYWJVNXRHHP-HNNXBMFYSA-N 6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-1-[(2s)-4-methyl-1-phosphonooxypentan-2-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1N=C2N([C@H](COP(O)(O)=O)CC(C)C)C=C(C(O)=O)C(=O)C2=CC=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 AYGKYWJVNXRHHP-HNNXBMFYSA-N 0.000 claims 1
- WGYLWURIVLVXNR-FQEVSTJZSA-N 6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-1-[(3s)-1-(2-morpholin-4-ylethyl)piperidin-3-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1N=C2N([C@@H]3CN(CCN4CCOCC4)CCC3)C=C(C(O)=O)C(=O)C2=CC=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 WGYLWURIVLVXNR-FQEVSTJZSA-N 0.000 claims 1
- XVELCQLIFQVOMG-MRXNPFEDSA-N 6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-1-[[(2r)-1-ethylpyrrolidin-2-yl]methyl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1N=C2N(C[C@@H]3N(CCC3)CC)C=C(C(O)=O)C(=O)C2=CC=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 XVELCQLIFQVOMG-MRXNPFEDSA-N 0.000 claims 1
- XVELCQLIFQVOMG-INIZCTEOSA-N 6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-1-[[(2s)-1-ethylpyrrolidin-2-yl]methyl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1N=C2N(C[C@H]3N(CCC3)CC)C=C(C(O)=O)C(=O)C2=CC=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 XVELCQLIFQVOMG-INIZCTEOSA-N 0.000 claims 1
- OMWQGXHZJXUWPF-IBGZPJMESA-N 6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-1-[[(2s)-1-ethylpyrrolidin-2-yl]methyl]-7-(4-methylpiperazin-1-yl)-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1C(C(C(C(O)=O)=CN2C[C@H]3N(CCC3)CC)=O)=C2N=C(N2CCN(C)CC2)C=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 OMWQGXHZJXUWPF-IBGZPJMESA-N 0.000 claims 1
- IEWOQDDHVCQCMJ-UHFFFAOYSA-N 6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-4-oxo-1-(2-phosphonooxyethyl)-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1N=C2N(CCOP(O)(O)=O)C=C(C(O)=O)C(=O)C2=CC=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 IEWOQDDHVCQCMJ-UHFFFAOYSA-N 0.000 claims 1
- KQUUCRZRKGQNFH-UHFFFAOYSA-N 7-(3-aminopyrrolidin-1-yl)-1-ethyl-6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1C(C(C(C(O)=O)=CN2CC)=O)=C2N=C(N2CC(N)CC2)C=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 KQUUCRZRKGQNFH-UHFFFAOYSA-N 0.000 claims 1
- WYLDRSBAVPXMHB-ZZAPORBBSA-N 7-(3-aminopyrrolidin-1-yl)-6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-1-[(2s)-1-hydroxy-3,3-dimethylbutan-2-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1C(C(C(C(O)=O)=CN2[C@H](CO)C(C)(C)C)=O)=C2N=C(N2CC(N)CC2)C=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 WYLDRSBAVPXMHB-ZZAPORBBSA-N 0.000 claims 1
- PAEITODLSKNYCM-UHFFFAOYSA-N 7-[2-(dimethylamino)ethylamino]-1-ethyl-6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C=1C(C(C(C(O)=O)=CN2CC)=O)=C2N=C(NCCN(C)C)C=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 PAEITODLSKNYCM-UHFFFAOYSA-N 0.000 claims 1
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- 108010054814 DNA Gyrase Proteins 0.000 claims 1
- 108010041052 DNA Topoisomerase IV Proteins 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- SLNBDNLMLVSKNX-LJQANCHMSA-N ethyl 6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-1-[(3r)-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-3-yl]-4-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C=1N=C2N([C@H]3CN(CCC3)C(=O)OC(C)(C)C)C=C(C(=O)OCC)C(=O)C2=CC=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 SLNBDNLMLVSKNX-LJQANCHMSA-N 0.000 claims 1
- LMYYCRAONQHSQK-MRXNPFEDSA-N ethyl 6-[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl]-4-oxo-1-[(3r)-piperidin-3-yl]-1,8-naphthyridine-3-carboxylate Chemical compound C=1N=C2N([C@H]3CNCCC3)C=C(C(=O)OCC)C(=O)C2=CC=1C=1C=NC(NC(=O)NCC)=CC=1C1=NC(C(F)(F)F)=CS1 LMYYCRAONQHSQK-MRXNPFEDSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- RQCNHUCCQJMSRG-UHFFFAOYSA-N tert-butyl piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1 RQCNHUCCQJMSRG-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18237309P | 2009-05-29 | 2009-05-29 | |
| US61/182,373 | 2009-05-29 | ||
| US28501709P | 2009-12-09 | 2009-12-09 | |
| US61/285,017 | 2009-12-09 | ||
| PCT/GB2010/050908 WO2010136817A1 (en) | 2009-05-29 | 2010-05-28 | Heterocyclic urea derivatives and methods of use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012528137A JP2012528137A (ja) | 2012-11-12 |
| JP2012528137A5 true JP2012528137A5 (enExample) | 2013-06-20 |
Family
ID=42635508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012512460A Withdrawn JP2012528137A (ja) | 2009-05-29 | 2010-05-28 | 複素環式尿素誘導体およびそれらの使用方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8569484B2 (enExample) |
| EP (1) | EP2435434A1 (enExample) |
| JP (1) | JP2012528137A (enExample) |
| CN (1) | CN102448962A (enExample) |
| AR (1) | AR076899A1 (enExample) |
| TW (1) | TW201102065A (enExample) |
| UY (1) | UY32674A (enExample) |
| WO (1) | WO2010136817A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2012010666A (es) | 2010-03-31 | 2012-10-05 | Actelion Pharmaceuticals Ltd | Derivados de isoquinolin-3-ilurea antibacterianos. |
| AR088729A1 (es) | 2011-03-29 | 2014-07-02 | Actelion Pharmaceuticals Ltd | Derivados de 3-ureidoisoquinolin-8-ilo y una composicion farmaceutica |
| EP3604281A4 (en) | 2017-03-24 | 2020-08-19 | Taisho Pharmaceutical Co., Ltd. | 2(1h)-quinolinone derivative |
| JP7344125B2 (ja) * | 2017-03-30 | 2023-09-13 | エフ． ホフマン－ラ ロシュ アーゲー | 細菌感染の治療及び予防のための新規ピリド［２，３－ｂ］インドール化合物 |
| AU2018302178A1 (en) * | 2017-07-18 | 2020-02-13 | Nuvation Bio Inc. | 1,8-naphthyridinone compounds and uses thereof |
| CN107445981B (zh) * | 2017-08-25 | 2018-06-22 | 牡丹江医学院 | 一种用于防治宫颈炎的活性化合物 |
| CN112752762A (zh) * | 2018-09-26 | 2021-05-04 | 豪夫迈·罗氏有限公司 | 用于治疗和预防细菌感染的取代的吡啶并吲哚 |
| KR20210116550A (ko) | 2019-01-18 | 2021-09-27 | 누베이션 바이오 인크. | 아데노신 길항제로서의 헤테로시클릭 화합물 |
| US11254670B2 (en) | 2019-01-18 | 2022-02-22 | Nuvation Bio Inc. | 1,8-naphthyridinone compounds and uses thereof |
| US20230002359A1 (en) | 2019-11-01 | 2023-01-05 | Syngenta Crop Protection Ag | Pesticidally active fused bicyclic heteroaromatic compounds |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0589985A1 (en) * | 1991-06-21 | 1994-04-06 | Boehringer Mannheim Italia S.P.A. | 2-amino-4-aryl-thiazoles with antiasthmatic and anti-inflammatory activities on the respiratory tract |
| TW538046B (en) | 1998-01-08 | 2003-06-21 | Hoechst Marion Roussel Inc | Aromatic amides having antiobiotic activities and the preparation processes, intermediates and pharmaceutical composition thereof |
| NZ520628A (en) | 2000-01-18 | 2004-05-28 | Vertex Pharma | thiazole, oxazole, imdazole or pyrazole substituted pyrazole derivatives useful as treating bacterial infections |
| DE60139964D1 (de) * | 2000-12-15 | 2009-10-29 | Vertex Pharma | Bakterielle Gyrase-Hemmer sowie deren Verwendung |
| TW200526626A (en) | 2003-09-13 | 2005-08-16 | Astrazeneca Ab | Chemical compounds |
| EP1856103A2 (en) | 2005-02-18 | 2007-11-21 | AstraZeneca AB | Pyrrole derivatives as dna gyrase and topoisomerase inhibitors |
| WO2006087543A1 (en) | 2005-02-18 | 2006-08-24 | Astrazeneca Ab | Antibacterial piperidine derivatives |
| US20080161306A1 (en) | 2005-02-18 | 2008-07-03 | Brian Sherer | Pyrrole Derivatives as Dna Gyrase and Topoisomerase Inhibitors |
| US20090253671A1 (en) | 2005-03-04 | 2009-10-08 | Astrazeneca Ab | Tricyclic derivatives of azetidine and pyrrole with antibacterial activity |
| JP2008531671A (ja) | 2005-03-04 | 2008-08-14 | アストラゼネカ アクチボラグ | 化合物 |
| JP2009520785A (ja) | 2005-12-23 | 2009-05-28 | アストラゼネカ アクチボラグ | 抗菌性のピロロピリジン、ピロロピリミジン、及びピロロアゼピン |
| DE602007014256D1 (de) | 2006-12-04 | 2011-06-09 | Astrazeneca Ab | Antibakterielle polycyclische harnstoffverbindungen |
| WO2009089263A2 (en) | 2008-01-07 | 2009-07-16 | Ardea Biosciences Inc. | Novel compositions and methods of use |
| TW200940537A (en) | 2008-02-26 | 2009-10-01 | Astrazeneca Ab | Heterocyclic urea derivatives and methods of use thereof |
| KR20110014710A (ko) * | 2008-06-04 | 2011-02-11 | 아스트라제네카 아베 | 박테리아 감염의 치료를 위한 헤테로시클릭 우레아 유도체 |
-
2010
- 2010-05-27 TW TW099117083A patent/TW201102065A/zh unknown
- 2010-05-28 US US13/322,717 patent/US8569484B2/en not_active Expired - Fee Related
- 2010-05-28 CN CN2010800246088A patent/CN102448962A/zh active Pending
- 2010-05-28 JP JP2012512460A patent/JP2012528137A/ja not_active Withdrawn
- 2010-05-28 UY UY0001032674A patent/UY32674A/es not_active Application Discontinuation
- 2010-05-28 AR ARP100101876A patent/AR076899A1/es unknown
- 2010-05-28 EP EP10724561A patent/EP2435434A1/en not_active Withdrawn
- 2010-05-28 WO PCT/GB2010/050908 patent/WO2010136817A1/en not_active Ceased
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