HRP20110048T1 - Spojevi piperidina i njihova upotreba - Google Patents
Spojevi piperidina i njihova upotreba Download PDFInfo
- Publication number
- HRP20110048T1 HRP20110048T1 HR20110048T HRP20110048T HRP20110048T1 HR P20110048 T1 HRP20110048 T1 HR P20110048T1 HR 20110048 T HR20110048 T HR 20110048T HR P20110048 T HRP20110048 T HR P20110048T HR P20110048 T1 HRP20110048 T1 HR P20110048T1
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- thiazole
- amino
- dichloro
- carbonyl
- Prior art date
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- 150000003053 piperidines Chemical class 0.000 title 1
- -1 methoxy, ethoxy, propoxy Chemical group 0.000 claims abstract 78
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 22
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 22
- 150000001875 compounds Chemical class 0.000 claims abstract 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 19
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 14
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 13
- 229910052799 carbon Inorganic materials 0.000 claims abstract 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 10
- 239000001257 hydrogen Substances 0.000 claims abstract 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 6
- 125000005843 halogen group Chemical group 0.000 claims abstract 6
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims abstract 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims abstract 4
- 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 abstract 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract 4
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 4
- 125000004452 carbocyclyl group Chemical group 0.000 claims abstract 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims abstract 2
- 125000002334 N-hydroxyacetimidoyl group Chemical group [H]C([H])([H])C([*])=NO[H] 0.000 claims abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 2
- 125000005336 allyloxy group Chemical group 0.000 claims abstract 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims abstract 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims abstract 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 125000002883 imidazolyl group Chemical group 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 5
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 claims 3
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 3
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims 3
- 229960003085 meticillin Drugs 0.000 claims 3
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 3
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 3
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 2
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims 2
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 2
- LFLXIHNBOOCJDC-ZJUUUORDSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(5-methyl-1,3,4-oxadiazol-2-yl)-1,3-thiazole-5-carboxylic acid Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(C=2OC(C)=NN=2)N=1)C(O)=O)C(=O)C=1NC(C)=C(Cl)C=1Cl LFLXIHNBOOCJDC-ZJUUUORDSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 206010035664 Pneumonia Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- KZJBDFCNPYQQGQ-NWDGAFQWSA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-(6-methoxypyridin-2-yl)-1,3-thiazole-5-carboxylate Chemical compound COC(=O)C=1SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)=NC=1C1=CC=CC(OC)=N1 KZJBDFCNPYQQGQ-NWDGAFQWSA-N 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 claims 1
- KYCBHBBWZDFNHH-RISCZKNCSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrol-2-yl)methylamino]-3-methoxypiperidin-1-yl]-4-(1-methylimidazol-4-yl)-1,3-thiazole-5-carboxylic acid Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(C=2N=CN(C)C=2)N=1)C(O)=O)CC=1NC(C)=C(Cl)C=1Cl KYCBHBBWZDFNHH-RISCZKNCSA-N 0.000 claims 1
- QWDZASVGBGYUNP-DTWKUNHWSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-(1,3-thiazol-2-yl)-1,3-thiazole-5-carboxylic acid Chemical class ClC1=C(C)NC(C(=O)N[C@H]2[C@H](CN(CC2)C=2SC(=C(C=3SC=CN=3)N=2)C(O)=O)F)=C1Cl QWDZASVGBGYUNP-DTWKUNHWSA-N 0.000 claims 1
- MRBKBGNDBLNSSD-VHSXEESVSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-(1-methylimidazol-2-yl)-1,3-thiazole-5-carboxylic acid Chemical compound ClC1=C(C)NC(C(=O)N[C@H]2[C@H](CN(CC2)C=2SC(=C(N=2)C=2N(C=CN=2)C)C(O)=O)F)=C1Cl MRBKBGNDBLNSSD-VHSXEESVSA-N 0.000 claims 1
- QLOGPUPHRNATNB-DTWKUNHWSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-(1-methyltriazol-4-yl)-1,3-thiazole-5-carboxylic acid Chemical class ClC1=C(C)NC(C(=O)N[C@H]2[C@H](CN(CC2)C=2SC(=C(C=3N=NN(C)C=3)N=2)C(O)=O)F)=C1Cl QLOGPUPHRNATNB-DTWKUNHWSA-N 0.000 claims 1
- XDJVMPRFMFDWPD-DTWKUNHWSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-(1h-imidazol-2-yl)-1,3-thiazole-5-carboxylic acid Chemical compound ClC1=C(C)NC(C(=O)N[C@H]2[C@H](CN(CC2)C=2SC(=C(C=3NC=CN=3)N=2)C(O)=O)F)=C1Cl XDJVMPRFMFDWPD-DTWKUNHWSA-N 0.000 claims 1
- SPKRXNPRBQSJKP-DTWKUNHWSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-(1h-pyrazol-5-yl)-1,3-thiazole-5-carboxylic acid Chemical compound ClC1=C(C)NC(C(=O)N[C@H]2[C@H](CN(CC2)C=2SC(=C(C=3NN=CC=3)N=2)C(O)=O)F)=C1Cl SPKRXNPRBQSJKP-DTWKUNHWSA-N 0.000 claims 1
- KRDCBLVDGPTPJC-DTWKUNHWSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-(2-methyl-1,2,4-triazol-3-yl)-1,3-thiazole-5-carboxylic acid Chemical compound ClC1=C(C)NC(C(=O)N[C@H]2[C@H](CN(CC2)C=2SC(=C(N=2)C=2N(N=CN=2)C)C(O)=O)F)=C1Cl KRDCBLVDGPTPJC-DTWKUNHWSA-N 0.000 claims 1
- ZYWAFJOOQXOXGI-WDEREUQCSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-(3-fluoropyridin-2-yl)-1,3-thiazole-5-carboxylic acid Chemical class ClC1=C(C)NC(C(=O)N[C@H]2[C@H](CN(CC2)C=2SC(=C(N=2)C=2C(=CC=CN=2)F)C(O)=O)F)=C1Cl ZYWAFJOOQXOXGI-WDEREUQCSA-N 0.000 claims 1
- WFIZRJDZBIVUKB-NWDGAFQWSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-[1-(2-methoxyethyl)imidazol-2-yl]-1,3-thiazole-5-carboxylic acid Chemical compound COCCN1C=CN=C1C1=C(C(O)=O)SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)=N1 WFIZRJDZBIVUKB-NWDGAFQWSA-N 0.000 claims 1
- REHMTUIHPPUJQB-WDEREUQCSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-[1-(methoxymethyl)imidazol-2-yl]-1,3-thiazole-5-carboxylic acid Chemical compound COCN1C=CN=C1C1=C(C(O)=O)SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)=N1 REHMTUIHPPUJQB-WDEREUQCSA-N 0.000 claims 1
- PPFMFFJQRSQJAI-VHSXEESVSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-[2-(dimethylamino)-1,3-thiazol-4-yl]-1,3-thiazole-5-carboxylic acid Chemical compound S1C(N(C)C)=NC(C2=C(SC(=N2)N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)C(O)=O)=C1 PPFMFFJQRSQJAI-VHSXEESVSA-N 0.000 claims 1
- WTHGXDXQTAJXGO-DTWKUNHWSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-[2-(methylamino)-1,3-thiazol-4-yl]-1,3-thiazole-5-carboxylic acid Chemical compound S1C(NC)=NC(C2=C(SC(=N2)N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)C(O)=O)=C1 WTHGXDXQTAJXGO-DTWKUNHWSA-N 0.000 claims 1
- ZYKKXNSHGPKKBJ-WDEREUQCSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-pyridin-2-yl-1,3-thiazole-5-carboxylic acid Chemical class ClC1=C(C)NC(C(=O)N[C@H]2[C@H](CN(CC2)C=2SC(=C(N=2)C=2N=CC=CC=2)C(O)=O)F)=C1Cl ZYKKXNSHGPKKBJ-WDEREUQCSA-N 0.000 claims 1
- NISYPSQCTVWPTM-VHSXEESVSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-pyrimidin-2-yl-1,3-thiazole-5-carboxylic acid Chemical class ClC1=C(C)NC(C(=O)N[C@H]2[C@H](CN(CC2)C=2SC(=C(N=2)C=2N=CC=CN=2)C(O)=O)F)=C1Cl NISYPSQCTVWPTM-VHSXEESVSA-N 0.000 claims 1
- HXWSVYPVMFQQCI-VHSXEESVSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-pyrimidin-4-yl-1,3-thiazole-5-carboxylic acid Chemical class ClC1=C(C)NC(C(=O)N[C@H]2[C@H](CN(CC2)C=2SC(=C(N=2)C=2N=CN=CC=2)C(O)=O)F)=C1Cl HXWSVYPVMFQQCI-VHSXEESVSA-N 0.000 claims 1
- YHNFMYSQJCPWFU-LYCTWNKOSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(1,3-dimethylimidazol-1-ium-2-yl)-1,3-thiazole-5-carboxylic acid;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(N=1)C1=[N+](C=CN1C)C)C(O)=O)C(=O)C=1NC(C)=C(Cl)C=1Cl YHNFMYSQJCPWFU-LYCTWNKOSA-N 0.000 claims 1
- WCCQHHYTDZGLAO-ZJUUUORDSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(1,3-thiazol-2-yl)-1,3-thiazole-5-carboxylic acid Chemical class N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(C=2SC=CN=2)N=1)C(O)=O)C(=O)C=1NC(C)=C(Cl)C=1Cl WCCQHHYTDZGLAO-ZJUUUORDSA-N 0.000 claims 1
- KPIOIQAQJYZGQJ-OLZOCXBDSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(1,4,5-trimethylimidazol-2-yl)-1,3-thiazole-5-carboxylic acid Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(C=2N(C(C)=C(C)N=2)C)N=1)C(O)=O)C(=O)C=1NC(C)=C(Cl)C=1Cl KPIOIQAQJYZGQJ-OLZOCXBDSA-N 0.000 claims 1
- WGUQUFAQRYHLPM-MNOVXSKESA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(1-methylimidazol-2-yl)-1,3-thiazole-5-carboxylic acid Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(N=1)C=1N(C=CN=1)C)C(O)=O)C(=O)C=1NC(C)=C(Cl)C=1Cl WGUQUFAQRYHLPM-MNOVXSKESA-N 0.000 claims 1
- DUKDXCRLTKNADX-PWSUYJOCSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(1-methylpyrazol-3-yl)-1,3-thiazole-5-carboxylic acid Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(C2=NN(C)C=C2)N=1)C(O)=O)C(=O)C=1NC(C)=C(Cl)C=1Cl DUKDXCRLTKNADX-PWSUYJOCSA-N 0.000 claims 1
- OZCDQOTXFXOOSW-KOLCDFICSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(1-methyltriazol-4-yl)-1,3-thiazole-5-carboxylic acid Chemical class N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(C=2N=NN(C)C=2)N=1)C(O)=O)C(=O)C=1NC(C)=C(Cl)C=1Cl OZCDQOTXFXOOSW-KOLCDFICSA-N 0.000 claims 1
- WKUCIXRHFLRSRK-ZJUUUORDSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(1h-imidazol-2-yl)-1,3-thiazole-5-carboxylic acid Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(C=2NC=CN=2)N=1)C(O)=O)C(=O)C=1NC(C)=C(Cl)C=1Cl WKUCIXRHFLRSRK-ZJUUUORDSA-N 0.000 claims 1
- QOAINSIYIQDSPH-KOLCDFICSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(1h-pyrazol-5-yl)-1,3-thiazole-5-carboxylic acid Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(C=2NN=CC=2)N=1)C(O)=O)C(=O)C=1NC(C)=C(Cl)C=1Cl QOAINSIYIQDSPH-KOLCDFICSA-N 0.000 claims 1
- GUPZBAWDBCOAOF-OLZOCXBDSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(3,5-dimethylpyrazin-2-yl)-1,3-thiazole-5-carboxylic acid Chemical class N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(N=1)C=1C(=NC(C)=CN=1)C)C(O)=O)C(=O)C=1NC(C)=C(Cl)C=1Cl GUPZBAWDBCOAOF-OLZOCXBDSA-N 0.000 claims 1
- SZSDINAPKOESMU-MNOVXSKESA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(4-methoxypyrimidin-2-yl)-1,3-thiazole-5-carboxylic acid Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(N=1)C=1N=C(OC)C=CN=1)C(O)=O)C(=O)C=1NC(C)=C(Cl)C=1Cl SZSDINAPKOESMU-MNOVXSKESA-N 0.000 claims 1
- DCZNAXNTQABOHC-OLZOCXBDSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-[1-(2-methoxyethyl)imidazol-2-yl]-1,3-thiazole-5-carboxylic acid Chemical compound COCCN1C=CN=C1C1=C(C(O)=O)SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)OC)=N1 DCZNAXNTQABOHC-OLZOCXBDSA-N 0.000 claims 1
- KKEGPKCMBPRZEC-CVEARBPZSA-N 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-[1-(2-trimethylsilylethoxymethyl)imidazol-2-yl]-1,3-thiazole-5-carboxylic acid Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(N=1)C=1N(C=CN=1)COCC[Si](C)(C)C)C(O)=O)C(=O)C=1NC(C)=C(Cl)C=1Cl KKEGPKCMBPRZEC-CVEARBPZSA-N 0.000 claims 1
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- MYPYJXKWCTUITO-KIIOPKALSA-N chembl3301825 Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)C(O)[C@H](C)O1 MYPYJXKWCTUITO-KIIOPKALSA-N 0.000 claims 1
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- RTIBVLHNSDXWBR-NWDGAFQWSA-N ethyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-(1-methylimidazol-4-yl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)=NC=1C1=CN(C)C=N1 RTIBVLHNSDXWBR-NWDGAFQWSA-N 0.000 claims 1
- OLLHAMOOPUVVRY-QWHCGFSZSA-N ethyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-(3-fluoropyridin-2-yl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)=NC=1C1=NC=CC=C1F OLLHAMOOPUVVRY-QWHCGFSZSA-N 0.000 claims 1
- PHQUAEGAKFORLQ-UONOGXRCSA-N ethyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-(4-methoxypyridin-2-yl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)=NC=1C1=CC(OC)=CC=N1 PHQUAEGAKFORLQ-UONOGXRCSA-N 0.000 claims 1
- URKXCDWWUXBBAT-NWDGAFQWSA-N ethyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-pyrazin-2-yl-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)=NC=1C1=CN=CC=N1 URKXCDWWUXBBAT-NWDGAFQWSA-N 0.000 claims 1
- AVNVMGMKBUCXFN-QWHCGFSZSA-N ethyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-pyridin-2-yl-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)=NC=1C1=CC=CC=N1 AVNVMGMKBUCXFN-QWHCGFSZSA-N 0.000 claims 1
- WQXHVIJTSLKKEW-NWDGAFQWSA-N ethyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-pyrimidin-4-yl-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)=NC=1C1=CC=NC=N1 WQXHVIJTSLKKEW-NWDGAFQWSA-N 0.000 claims 1
- UGLRXYMYBRJVNG-MNOVXSKESA-N ethyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(1,3,4-oxadiazol-2-yl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)OC)=NC=1C1=NN=CO1 UGLRXYMYBRJVNG-MNOVXSKESA-N 0.000 claims 1
- KCIBGKUHQZMHJV-OCCSQVGLSA-N ethyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(1-methylimidazol-4-yl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)OC)=NC=1C1=CN(C)C=N1 KCIBGKUHQZMHJV-OCCSQVGLSA-N 0.000 claims 1
- LYRYDEHHZMHEPV-OCCSQVGLSA-N ethyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(1-methylpyrazol-3-yl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)OC)=NC=1C=1C=CN(C)N=1 LYRYDEHHZMHEPV-OCCSQVGLSA-N 0.000 claims 1
- ITVYVIYUUPLWFI-NEPJUHHUSA-N ethyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(3-methyl-1,2,4-oxadiazol-5-yl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)OC)=NC=1C1=NC(C)=NO1 ITVYVIYUUPLWFI-NEPJUHHUSA-N 0.000 claims 1
- XAEZSHCXNGPSEL-OLZOCXBDSA-N ethyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(4,6-dimethoxypyrimidin-2-yl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)OC)=NC=1C1=NC(OC)=CC(OC)=N1 XAEZSHCXNGPSEL-OLZOCXBDSA-N 0.000 claims 1
- GLIHVSOCGJGXQZ-ZBFHGGJFSA-N ethyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(4-methoxypyridin-2-yl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)OC)=NC=1C1=CC(OC)=CC=N1 GLIHVSOCGJGXQZ-ZBFHGGJFSA-N 0.000 claims 1
- WVSLXSBKXPRAFC-NEPJUHHUSA-N ethyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(5-methyl-1,3,4-oxadiazol-2-yl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)OC)=NC=1C1=NN=C(C)O1 WVSLXSBKXPRAFC-NEPJUHHUSA-N 0.000 claims 1
- OEUVAWKZWHYDMN-HIFRSBDPSA-N ethyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(5-methylpyrazin-2-yl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)OC)=NC=1C1=CN=C(C)C=N1 OEUVAWKZWHYDMN-HIFRSBDPSA-N 0.000 claims 1
- NAXUSQLDJRTELE-OCCSQVGLSA-N ethyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-pyrazin-2-yl-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)OC)=NC=1C1=CN=CC=N1 NAXUSQLDJRTELE-OCCSQVGLSA-N 0.000 claims 1
- YNZGJOMFSVLCDX-HIFRSBDPSA-N ethyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-pyridin-2-yl-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)OC)=NC=1C1=CC=CC=N1 YNZGJOMFSVLCDX-HIFRSBDPSA-N 0.000 claims 1
- NISCFGIQVQRSCP-OLZOCXBDSA-N ethyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-pyrimidin-2-yl-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)OC)=NC=1C1=NC=CC=N1 NISCFGIQVQRSCP-OLZOCXBDSA-N 0.000 claims 1
- NDZOMJVDXNGETK-OCCSQVGLSA-N ethyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-pyrimidin-4-yl-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)OC)=NC=1C1=CC=NC=N1 NDZOMJVDXNGETK-OCCSQVGLSA-N 0.000 claims 1
- WMNUKNRLIMKPEM-UONOGXRCSA-N ethyl 2-[(3s,4r)-4-[(4-chloro-3,5-dimethyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-pyrazin-2-yl-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)C)CC2)=NC=1C1=CN=CC=N1 WMNUKNRLIMKPEM-UONOGXRCSA-N 0.000 claims 1
- WIVPZJGIUOFWPN-UONOGXRCSA-N ethyl 2-[(3s,4r)-4-[(4-chloro-3,5-dimethyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-pyrimidin-4-yl-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)C)CC2)=NC=1C1=CC=NC=N1 WIVPZJGIUOFWPN-UONOGXRCSA-N 0.000 claims 1
- UXHNQTLZJZAIQA-UONOGXRCSA-N ethyl 2-[(3s,4r)-4-[(4-chloro-3-cyano-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-pyrazin-2-yl-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)C#N)CC2)=NC=1C1=CN=CC=N1 UXHNQTLZJZAIQA-UONOGXRCSA-N 0.000 claims 1
- KLRUGBSNLKUFGK-ZBFHGGJFSA-N ethyl 2-[(3s,4r)-4-[(4-chloro-3-cyano-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(1-methylimidazol-4-yl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)C#N)CC2)OC)=NC=1C1=CN(C)C=N1 KLRUGBSNLKUFGK-ZBFHGGJFSA-N 0.000 claims 1
- YTDUKIDHXXENEH-ZBFHGGJFSA-N ethyl 2-[(3s,4r)-4-[(4-chloro-3-cyano-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(1-methylpyrazol-3-yl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)C#N)CC2)OC)=NC=1C=1C=CN(C)N=1 YTDUKIDHXXENEH-ZBFHGGJFSA-N 0.000 claims 1
- OCTOETNQKLAIDJ-CVEARBPZSA-N ethyl 2-[(3s,4r)-4-[(4-chloro-3-cyano-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(3-fluoropyridin-2-yl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)C#N)CC2)OC)=NC=1C1=NC=CC=C1F OCTOETNQKLAIDJ-CVEARBPZSA-N 0.000 claims 1
- UFNMWQOFONTEHL-WBVHZDCISA-N ethyl 2-[(3s,4r)-4-[(4-chloro-3-cyano-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(5-methylpyrazin-2-yl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)C#N)CC2)OC)=NC=1C1=CN=C(C)C=N1 UFNMWQOFONTEHL-WBVHZDCISA-N 0.000 claims 1
- VEMRGPFFWPDYJI-CABCVRRESA-N ethyl 2-[(3s,4r)-4-[(4-chloro-3-cyano-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-pyrimidin-2-yl-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)C#N)CC2)OC)=NC=1C1=NC=CC=N1 VEMRGPFFWPDYJI-CABCVRRESA-N 0.000 claims 1
- MODXMFCUJDBDGW-ZBFHGGJFSA-N ethyl 2-[(3s,4r)-4-[(4-chloro-3-cyano-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-pyrimidin-4-yl-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)C#N)CC2)OC)=NC=1C1=CC=NC=N1 MODXMFCUJDBDGW-ZBFHGGJFSA-N 0.000 claims 1
- UTHMZCHXBSMLPL-QWHCGFSZSA-N ethyl 4-(1,3-benzothiazol-2-yl)-2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-1,3-thiazole-5-carboxylate Chemical compound N([C@@H]1CCN(C[C@@H]1F)C=1SC(=C(N=1)C=1SC2=CC=CC=C2N=1)C(=O)OCC)C(=O)C=1NC(C)=C(Cl)C=1Cl UTHMZCHXBSMLPL-QWHCGFSZSA-N 0.000 claims 1
- LUKYYEBQOGOTKH-HIFRSBDPSA-N ethyl 4-(1,3-benzothiazol-2-yl)-2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-1,3-thiazole-5-carboxylate Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(N=1)C=1SC2=CC=CC=C2N=1)C(=O)OCC)C(=O)C=1NC(C)=C(Cl)C=1Cl LUKYYEBQOGOTKH-HIFRSBDPSA-N 0.000 claims 1
- DUHPJSMQTDRFGI-UONOGXRCSA-N ethyl 4-[2,6-bis(dimethylamino)pyrimidin-4-yl]-2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)=NC=1C1=CC(N(C)C)=NC(N(C)C)=N1 DUHPJSMQTDRFGI-UONOGXRCSA-N 0.000 claims 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 208000022760 infectious otitis media Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- UBROMCZFLBOEQP-VHSXEESVSA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-(1,2-oxazol-5-yl)-1,3-thiazole-5-carboxylate Chemical compound COC(=O)C=1SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)=NC=1C1=CC=NO1 UBROMCZFLBOEQP-VHSXEESVSA-N 0.000 claims 1
- VOJPPYWNMOGCBW-VHSXEESVSA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-(1,3-thiazol-2-yl)-1,3-thiazole-5-carboxylate Chemical compound COC(=O)C=1SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)=NC=1C1=NC=CS1 VOJPPYWNMOGCBW-VHSXEESVSA-N 0.000 claims 1
- AQHKGODIWPPFAF-WDEREUQCSA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-(1-methylimidazol-2-yl)-1,3-thiazole-5-carboxylate Chemical compound COC(=O)C=1SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)=NC=1C1=NC=CN1C AQHKGODIWPPFAF-WDEREUQCSA-N 0.000 claims 1
- ZJIYJHLNUYBHFQ-VHSXEESVSA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-(1-methyltriazol-4-yl)-1,3-thiazole-5-carboxylate Chemical compound COC(=O)C=1SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)=NC=1C1=CN(C)N=N1 ZJIYJHLNUYBHFQ-VHSXEESVSA-N 0.000 claims 1
- YQWCQHRCXOOLHV-VHSXEESVSA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-(2-methyl-1,2,4-triazol-3-yl)-1,3-thiazole-5-carboxylate Chemical compound COC(=O)C=1SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)=NC=1C1=NC=NN1C YQWCQHRCXOOLHV-VHSXEESVSA-N 0.000 claims 1
- ADNIDGSRHCBMJI-NWDGAFQWSA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-[1-(methoxymethyl)imidazol-2-yl]-1,3-thiazole-5-carboxylate Chemical compound COCN1C=CN=C1C1=C(C(=O)OC)SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)=N1 ADNIDGSRHCBMJI-NWDGAFQWSA-N 0.000 claims 1
- KICIUIOTUODMDD-WDEREUQCSA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-[2-(dimethylamino)-1,3-thiazol-4-yl]-1,3-thiazole-5-carboxylate Chemical compound COC(=O)C=1SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)=NC=1C1=CSC(N(C)C)=N1 KICIUIOTUODMDD-WDEREUQCSA-N 0.000 claims 1
- OVWUFJVSGIXJPF-VHSXEESVSA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-4-[2-(methylamino)-1,3-thiazol-4-yl]-1,3-thiazole-5-carboxylate Chemical compound S1C(NC)=NC(C2=C(SC(=N2)N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)C(=O)OC)=C1 OVWUFJVSGIXJPF-VHSXEESVSA-N 0.000 claims 1
- STABPZRTPOAECP-PWSUYJOCSA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(1,2-oxazol-5-yl)-1,3-thiazole-5-carboxylate Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(C=2ON=CC=2)N=1)C(=O)OC)C(=O)C=1NC(C)=C(Cl)C=1Cl STABPZRTPOAECP-PWSUYJOCSA-N 0.000 claims 1
- IWKKADUPWVEZER-KZCZEQIWSA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(1,3-dimethylimidazol-1-ium-2-yl)-1,3-thiazole-5-carboxylate;iodide Chemical compound [I-].N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(N=1)C1=[N+](C=CN1C)C)C(=O)OC)C(=O)C=1NC(C)=C(Cl)C=1Cl IWKKADUPWVEZER-KZCZEQIWSA-N 0.000 claims 1
- PNIDKUOSAQRPAR-MNOVXSKESA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(1,3-thiazol-2-yl)-1,3-thiazole-5-carboxylate Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(C=2SC=CN=2)N=1)C(=O)OC)C(=O)C=1NC(C)=C(Cl)C=1Cl PNIDKUOSAQRPAR-MNOVXSKESA-N 0.000 claims 1
- JSBHOVZROYQXAY-KGLIPLIRSA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(1,4,5-trimethylimidazol-2-yl)-1,3-thiazole-5-carboxylate Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(C=2N(C(C)=C(C)N=2)C)N=1)C(=O)OC)C(=O)C=1NC(C)=C(Cl)C=1Cl JSBHOVZROYQXAY-KGLIPLIRSA-N 0.000 claims 1
- XQOGGKORILAOKA-NEPJUHHUSA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(1-methylimidazol-2-yl)-1,3-thiazole-5-carboxylate Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(C=2N(C=CN=2)C)N=1)C(=O)OC)C(=O)C=1NC(C)=C(Cl)C=1Cl XQOGGKORILAOKA-NEPJUHHUSA-N 0.000 claims 1
- DSMJBAJAOAAJQH-PWSUYJOCSA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(1-methyltriazol-4-yl)-1,3-thiazole-5-carboxylate Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(C=2N=NN(C)C=2)N=1)C(=O)OC)C(=O)C=1NC(C)=C(Cl)C=1Cl DSMJBAJAOAAJQH-PWSUYJOCSA-N 0.000 claims 1
- AUXBJBREDOELSY-MNOVXSKESA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(1h-imidazol-2-yl)-1,3-thiazole-5-carboxylate Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(C=2NC=CN=2)N=1)C(=O)OC)C(=O)C=1NC(C)=C(Cl)C=1Cl AUXBJBREDOELSY-MNOVXSKESA-N 0.000 claims 1
- HJGOPSTXCWZNMJ-KGLIPLIRSA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(3,5-dimethylpyrazin-2-yl)-1,3-thiazole-5-carboxylate Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(N=1)C=1C(=NC(C)=CN=1)C)C(=O)OC)C(=O)C=1NC(C)=C(Cl)C=1Cl HJGOPSTXCWZNMJ-KGLIPLIRSA-N 0.000 claims 1
- QJHHAELEZGHPRY-NEPJUHHUSA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(4-methoxypyrimidin-2-yl)-1,3-thiazole-5-carboxylate Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(N=1)C=1N=C(OC)C=CN=1)C(=O)OC)C(=O)C=1NC(C)=C(Cl)C=1Cl QJHHAELEZGHPRY-NEPJUHHUSA-N 0.000 claims 1
- KYRIRWBXYUBVGZ-OCCSQVGLSA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(6-methoxypyridin-2-yl)-1,3-thiazole-5-carboxylate Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(N=1)C=1N=C(OC)C=CC=1)C(=O)OC)C(=O)C=1NC(C)=C(Cl)C=1Cl KYRIRWBXYUBVGZ-OCCSQVGLSA-N 0.000 claims 1
- PDVFHCQHCJLFTN-KGLIPLIRSA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-[1-(2-methoxyethyl)imidazol-2-yl]-1,3-thiazole-5-carboxylate Chemical compound COCCN1C=CN=C1C1=C(C(=O)OC)SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)OC)=N1 PDVFHCQHCJLFTN-KGLIPLIRSA-N 0.000 claims 1
- YWYAIBMPBMLSAQ-OLZOCXBDSA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-[1-(methoxymethyl)imidazol-2-yl]-1,3-thiazole-5-carboxylate Chemical compound COCN1C=CN=C1C1=C(C(=O)OC)SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)OC)=N1 YWYAIBMPBMLSAQ-OLZOCXBDSA-N 0.000 claims 1
- BTCNTADEUXMEEC-YPMHNXCESA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-[2-(dimethylamino)-1,3-thiazol-4-yl]-1,3-thiazole-5-carboxylate Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(C=2N=C(SC=2)N(C)C)N=1)C(=O)OC)C(=O)C=1NC(C)=C(Cl)C=1Cl BTCNTADEUXMEEC-YPMHNXCESA-N 0.000 claims 1
- UDPBIMTXSUQFAQ-PWSUYJOCSA-N methyl 2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-[2-(methylamino)-1,3-thiazol-4-yl]-1,3-thiazole-5-carboxylate Chemical compound S1C(NC)=NC(C2=C(SC(=N2)N2C[C@@H]([C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)OC)C(=O)OC)=C1 UDPBIMTXSUQFAQ-PWSUYJOCSA-N 0.000 claims 1
- RWBVSRMXDPBGRA-CVEARBPZSA-N methyl 2-[(3s,4r)-4-[(3-chloro-4-cyano-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-[1-(2-methoxyethyl)imidazol-2-yl]-1,3-thiazole-5-carboxylate Chemical compound COCCN1C=CN=C1C1=C(C(=O)OC)SC(N2C[C@@H]([C@H](NC(=O)C3=C(C(C#N)=C(C)N3)Cl)CC2)OC)=N1 RWBVSRMXDPBGRA-CVEARBPZSA-N 0.000 claims 1
- JYQJAYGWQHCPKU-OLZOCXBDSA-N methyl 2-[(3s,4r)-4-[(4-chloro-3-cyano-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-4-(2-methyl-1,2,4-triazol-3-yl)-1,3-thiazole-5-carboxylate Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(N=1)C=1N(N=CN=1)C)C(=O)OC)C(=O)C=1NC(C)=C(Cl)C=1C#N JYQJAYGWQHCPKU-OLZOCXBDSA-N 0.000 claims 1
- SNGPLFSOPBFGCU-DTWKUNHWSA-N methyl 4-(2-amino-1,3-thiazol-4-yl)-2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-fluoropiperidin-1-yl]-1,3-thiazole-5-carboxylate Chemical compound COC(=O)C=1SC(N2C[C@H](F)[C@H](NC(=O)C3=C(C(Cl)=C(C)N3)Cl)CC2)=NC=1C1=CSC(N)=N1 SNGPLFSOPBFGCU-DTWKUNHWSA-N 0.000 claims 1
- ZJUZTHAIKFXAKT-KOLCDFICSA-N methyl 4-(2-amino-1,3-thiazol-4-yl)-2-[(3s,4r)-4-[(3,4-dichloro-5-methyl-1h-pyrrole-2-carbonyl)amino]-3-methoxypiperidin-1-yl]-1,3-thiazole-5-carboxylate Chemical compound N([C@@H]1CCN(C[C@@H]1OC)C=1SC(=C(C=2N=C(N)SC=2)N=1)C(=O)OC)C(=O)C=1NC(C)=C(Cl)C=1Cl ZJUZTHAIKFXAKT-KOLCDFICSA-N 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 229940049954 penicillin Drugs 0.000 claims 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 claims 1
- 208000019206 urinary tract infection Diseases 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 4
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94344007P | 2007-06-12 | 2007-06-12 | |
| PCT/GB2008/050431 WO2008152418A1 (en) | 2007-06-12 | 2008-06-11 | Piperidine compounds and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110048T1 true HRP20110048T1 (hr) | 2011-03-31 |
Family
ID=39673349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110048T HRP20110048T1 (hr) | 2007-06-12 | 2011-01-21 | Spojevi piperidina i njihova upotreba |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US20080312255A1 (de) |
| EP (1) | EP2158199B1 (de) |
| JP (1) | JP2010529184A (de) |
| KR (1) | KR20100038095A (de) |
| CN (1) | CN102648199A (de) |
| AR (1) | AR066977A1 (de) |
| AT (1) | ATE488514T1 (de) |
| AU (1) | AU2008263580A1 (de) |
| BR (1) | BRPI0812473A2 (de) |
| CA (1) | CA2689076A1 (de) |
| CL (1) | CL2008001740A1 (de) |
| CO (1) | CO6311102A2 (de) |
| CY (1) | CY1111442T1 (de) |
| DE (1) | DE602008003575D1 (de) |
| DK (1) | DK2158199T3 (de) |
| ES (1) | ES2354647T3 (de) |
| HK (1) | HK1140198A1 (de) |
| HR (1) | HRP20110048T1 (de) |
| IL (1) | IL202367A0 (de) |
| MX (1) | MX2009013501A (de) |
| NZ (1) | NZ582516A (de) |
| PE (1) | PE20090555A1 (de) |
| PL (1) | PL2158199T3 (de) |
| PT (1) | PT2158199E (de) |
| RU (1) | RU2010100352A (de) |
| SA (1) | SA08290357B1 (de) |
| SI (1) | SI2158199T1 (de) |
| TW (1) | TW200906412A (de) |
| UY (1) | UY31141A1 (de) |
| WO (1) | WO2008152418A1 (de) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1853586B1 (de) * | 2005-02-18 | 2013-07-24 | AstraZeneca AB | Antibakterielle piperidinderivate |
| US8071605B2 (en) | 2008-12-12 | 2011-12-06 | Astrazeneca Ab | Piperidine compounds for use in the treatment of bacterial infections |
| TW201026694A (en) * | 2008-12-12 | 2010-07-16 | Astrazeneca Ab | Compound 468 |
| UY32856A (es) | 2009-08-26 | 2011-03-31 | Astrazeneca Ab | Derivados heterocíclicos de urea y métodos de uso de los mismos |
| WO2014164200A1 (en) | 2013-03-13 | 2014-10-09 | Avon Products, Inc | Tyrosinase inhibitors |
| US9364405B2 (en) | 2013-03-13 | 2016-06-14 | Avon Products, Inc. | Tyrosinase inhibitors |
| US10399968B2 (en) | 2015-09-30 | 2019-09-03 | Daiichi Sankyo Company, Limited | Hydroxyalkyl thiadiazole derivatives |
| EP3596071A1 (de) | 2017-03-14 | 2020-01-22 | Daiichi Sankyo Company, Limited | N-phosphonoxymethyl-prodrugs von hydroxyalkylthiadiazolderivaten |
| CA3057431A1 (en) | 2017-03-24 | 2018-09-27 | Taisho Pharmaceutical Co., Ltd. | 2(1h)-quinolinone derivative |
| WO2020048949A1 (en) | 2018-09-03 | 2020-03-12 | Univerza V Ljubljani | New class of dna gyrase and/or topoisomerase iv inhibitors with activity against gram-positive and gram-negative bacteria |
| CN110172435B (zh) * | 2019-06-06 | 2020-12-29 | 江南大学 | 一种催化合成2,5-二甲基吡嗪的重组菌 |
| WO2022129327A1 (en) | 2020-12-17 | 2022-06-23 | Univerza V Ljubljani | New n-phenylpyrrolamide inhibitors of dna gyrase and topoisomerase iv with antibacterial activity |
| CN115466246B (zh) * | 2021-06-11 | 2024-02-06 | 中国医学科学院药物研究所 | 吡咯酰哌啶胺类化合物及其用途 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046775A (en) * | 1973-04-11 | 1977-09-06 | Sterling Drug Inc. | 4,5-Dihalopyrrole-2-carboxamides |
| US3963480A (en) * | 1973-04-11 | 1976-06-15 | Sterling Drug Inc. | Herbicidal pyrrole-2-carboxamides |
| US4912109A (en) * | 1987-02-02 | 1990-03-27 | Boc, Inc. | N-heterocyclic-N-(4-piperidinyl) amides and pharmaceutical compositions and methods employing such compounds |
| US4791112A (en) * | 1987-02-02 | 1988-12-13 | The Boc Group, Inc. | N-heterocyclic-N-(4-piperidyl)amides and pharmaceutical compositions and methods employing such compounds |
| US5739135A (en) * | 1993-09-03 | 1998-04-14 | Bristol-Myers Squibb Company | Inhibitors of microsomal triglyceride transfer protein and method |
| NZ520628A (en) * | 2000-01-18 | 2004-05-28 | Vertex Pharma | thiazole, oxazole, imdazole or pyrazole substituted pyrazole derivatives useful as treating bacterial infections |
| KR101052433B1 (ko) * | 2002-06-13 | 2011-07-29 | 버텍스 파마슈티칼스 인코포레이티드 | 자이라제 및/또는 토포이소머라제 ⅳ 억제제로서의 2-우레이도-6-헤테로아릴-3ｈ-벤조이미다졸-4-카복실산 유도체 및 이를 포함하는 세균 감염 치료용 약제학적 조성물 |
| GB0321509D0 (en) * | 2003-09-13 | 2003-10-15 | Astrazeneca Ab | Chemical compounds |
| TW200526626A (en) * | 2003-09-13 | 2005-08-16 | Astrazeneca Ab | Chemical compounds |
| US20050197336A1 (en) * | 2004-03-08 | 2005-09-08 | Miikana Therapeutics Corporation | Inhibitors of histone deacetylase |
| US7345043B2 (en) * | 2004-04-01 | 2008-03-18 | Miikana Therapeutics | Inhibitors of histone deacetylase |
| EP1853586B1 (de) * | 2005-02-18 | 2013-07-24 | AstraZeneca AB | Antibakterielle piperidinderivate |
| TW200819437A (en) * | 2006-08-17 | 2008-05-01 | Astrazeneca Ab | Chemical compounds |
-
2008
- 2008-06-10 TW TW097121574A patent/TW200906412A/zh unknown
- 2008-06-11 US US12/136,884 patent/US20080312255A1/en not_active Abandoned
- 2008-06-11 WO PCT/GB2008/050431 patent/WO2008152418A1/en active Application Filing
- 2008-06-11 CA CA002689076A patent/CA2689076A1/en not_active Abandoned
- 2008-06-11 MX MX2009013501A patent/MX2009013501A/es active IP Right Grant
- 2008-06-11 PL PL08762541T patent/PL2158199T3/pl unknown
- 2008-06-11 ES ES08762541T patent/ES2354647T3/es active Active
- 2008-06-11 SI SI200830133T patent/SI2158199T1/sl unknown
- 2008-06-11 CN CN200880102731XA patent/CN102648199A/zh active Pending
- 2008-06-11 SA SA08290357A patent/SA08290357B1/ar unknown
- 2008-06-11 AU AU2008263580A patent/AU2008263580A1/en not_active Abandoned
- 2008-06-11 RU RU2010100352/04A patent/RU2010100352A/ru not_active Application Discontinuation
- 2008-06-11 EP EP08762541A patent/EP2158199B1/de active Active
- 2008-06-11 KR KR1020107000577A patent/KR20100038095A/ko not_active Application Discontinuation
- 2008-06-11 JP JP2010511728A patent/JP2010529184A/ja active Pending
- 2008-06-11 BR BRPI0812473-6A2A patent/BRPI0812473A2/pt not_active IP Right Cessation
- 2008-06-11 DK DK08762541.4T patent/DK2158199T3/da active
- 2008-06-11 NZ NZ582516A patent/NZ582516A/en not_active IP Right Cessation
- 2008-06-11 PT PT08762541T patent/PT2158199E/pt unknown
- 2008-06-11 UY UY31141A patent/UY31141A1/es not_active Application Discontinuation
- 2008-06-11 AT AT08762541T patent/ATE488514T1/de active
- 2008-06-11 DE DE602008003575T patent/DE602008003575D1/de active Active
- 2008-06-12 CL CL2008001740A patent/CL2008001740A1/es unknown
- 2008-06-12 AR ARP080102509A patent/AR066977A1/es not_active Application Discontinuation
- 2008-06-12 PE PE2008001008A patent/PE20090555A1/es not_active Application Discontinuation
-
2009
- 2009-11-26 IL IL202367A patent/IL202367A0/en unknown
-
2010
- 2010-01-08 CO CO10001889A patent/CO6311102A2/es not_active Application Discontinuation
- 2010-06-29 HK HK10106340.2A patent/HK1140198A1/xx not_active IP Right Cessation
-
2011
- 2011-01-19 CY CY20111100058T patent/CY1111442T1/el unknown
- 2011-01-21 HR HR20110048T patent/HRP20110048T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2010100352A (ru) | 2011-07-20 |
| SI2158199T1 (sl) | 2011-02-28 |
| AU2008263580A1 (en) | 2008-12-18 |
| AR066977A1 (es) | 2009-09-23 |
| CO6311102A2 (es) | 2011-08-22 |
| KR20100038095A (ko) | 2010-04-12 |
| ES2354647T3 (es) | 2011-03-16 |
| CA2689076A1 (en) | 2008-12-18 |
| US20080312255A1 (en) | 2008-12-18 |
| PT2158199E (pt) | 2011-01-19 |
| CY1111442T1 (el) | 2015-08-05 |
| CN102648199A (zh) | 2012-08-22 |
| EP2158199A1 (de) | 2010-03-03 |
| BRPI0812473A2 (pt) | 2014-12-02 |
| WO2008152418A1 (en) | 2008-12-18 |
| ATE488514T1 (de) | 2010-12-15 |
| DK2158199T3 (da) | 2011-02-07 |
| CL2008001740A1 (es) | 2009-07-17 |
| EP2158199B1 (de) | 2010-11-17 |
| JP2010529184A (ja) | 2010-08-26 |
| PE20090555A1 (es) | 2009-06-04 |
| NZ582516A (en) | 2012-03-30 |
| SA08290357B1 (ar) | 2011-06-22 |
| UY31141A1 (es) | 2009-01-30 |
| TW200906412A (en) | 2009-02-16 |
| HK1140198A1 (en) | 2010-10-08 |
| MX2009013501A (es) | 2010-01-18 |
| IL202367A0 (en) | 2010-06-30 |
| PL2158199T3 (pl) | 2011-04-29 |
| DE602008003575D1 (de) | 2010-12-30 |
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