JP2013518845A5 - - Google Patents
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- Publication number
- JP2013518845A5 JP2013518845A5 JP2012551586A JP2012551586A JP2013518845A5 JP 2013518845 A5 JP2013518845 A5 JP 2013518845A5 JP 2012551586 A JP2012551586 A JP 2012551586A JP 2012551586 A JP2012551586 A JP 2012551586A JP 2013518845 A5 JP2013518845 A5 JP 2013518845A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- methyl
- trans
- cyclohexyl
- ylmethyl
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 239000001257 hydrogen Substances 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 14
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 150000003839 salts Chemical group 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 102000012289 Corticotropin-Releasing Hormone Human genes 0.000 claims 5
- 108010022152 Corticotropin-Releasing Hormone Proteins 0.000 claims 5
- 239000000055 Corticotropin-Releasing Hormone Substances 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- -1 4-((4- (4-chlorophenyl) -5-methyl-1H-pyrazol-3-ylamino) methyl) cyclohexyl Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- GSQGCFTWOSTTHY-UHFFFAOYSA-N 5-chloro-2-methyl-n-[4-[(3,4,5-trimethylpyrazol-1-yl)methyl]cyclohexyl]pyridine-3-carboxamide Chemical compound CC1=C(C)C(C)=NN1CC1CCC(NC(=O)C=2C(=NC=C(Cl)C=2)C)CC1 GSQGCFTWOSTTHY-UHFFFAOYSA-N 0.000 claims 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 125000005605 benzo group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 229910052805 deuterium Inorganic materials 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000002464 receptor antagonist Substances 0.000 claims 2
- 229940044551 receptor antagonist Drugs 0.000 claims 2
- CWCYNBYBTACELK-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)-n-[4-[(3,4,5-trimethylpyrazol-1-yl)methyl]cyclohexyl]benzamide Chemical compound CC1=C(C)C(C)=NN1CC1CCC(NC(=O)C=2C(=CC=C(C=2)C(F)(F)F)Cl)CC1 CWCYNBYBTACELK-UHFFFAOYSA-N 0.000 claims 1
- AIAQEHWTQAOGLA-UHFFFAOYSA-N 2-chloro-n-[4-[(3-phenylpyrazol-1-yl)methyl]cyclohexyl]-5-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=C(Cl)C(C(=O)NC2CCC(CN3N=C(C=C3)C=3C=CC=CC=3)CC2)=C1 AIAQEHWTQAOGLA-UHFFFAOYSA-N 0.000 claims 1
- QJLODLOESBNNPM-UHFFFAOYSA-N 2-chloro-n-[4-[(4-chloro-3,5-dimethylpyrazol-1-yl)methyl]cyclohexyl]-5-(trifluoromethyl)benzamide Chemical compound CC1=C(Cl)C(C)=NN1CC1CCC(NC(=O)C=2C(=CC=C(C=2)C(F)(F)F)Cl)CC1 QJLODLOESBNNPM-UHFFFAOYSA-N 0.000 claims 1
- SUUSNFSQMHCMDE-UHFFFAOYSA-N 2-chloro-n-[4-[[3-(4-methoxyphenyl)-5-methylpyrazol-1-yl]methyl]cyclohexyl]-5-(trifluoromethyl)benzamide Chemical compound C1=CC(OC)=CC=C1C1=NN(CC2CCC(CC2)NC(=O)C=2C(=CC=C(C=2)C(F)(F)F)Cl)C(C)=C1 SUUSNFSQMHCMDE-UHFFFAOYSA-N 0.000 claims 1
- MRZCTSJNLTVOQB-UHFFFAOYSA-N 2-chloro-n-[4-[[4-chloro-3-(hydroxymethyl)pyrazol-1-yl]methyl]cyclohexyl]-5-(trifluoromethyl)benzamide Chemical compound C1=C(Cl)C(CO)=NN1CC1CCC(NC(=O)C=2C(=CC=C(C=2)C(F)(F)F)Cl)CC1 MRZCTSJNLTVOQB-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- YFGJKTCILASHFF-UHFFFAOYSA-N 5-chloro-n-[4-[(3,5-diethylpyrazol-1-yl)methyl]cyclohexyl]-2-methylpyridine-3-carboxamide Chemical compound N1=C(CC)C=C(CC)N1CC1CCC(NC(=O)C=2C(=NC=C(Cl)C=2)C)CC1 YFGJKTCILASHFF-UHFFFAOYSA-N 0.000 claims 1
- FZPRQRQELHONGW-UHFFFAOYSA-N 5-chloro-n-[4-[(3,5-dimethylpyrazol-1-yl)methyl]cyclohexyl]-2-methylpyridine-3-carboxamide Chemical compound N1=C(C)C=C(C)N1CC1CCC(NC(=O)C=2C(=NC=C(Cl)C=2)C)CC1 FZPRQRQELHONGW-UHFFFAOYSA-N 0.000 claims 1
- JRBVOUREXIRPPY-UHFFFAOYSA-N 5-chloro-n-[4-[(4-chloro-3,5-dimethylpyrazol-1-yl)methyl]cyclohexyl]-2-methylpyridine-3-carboxamide Chemical compound CC1=C(Cl)C(C)=NN1CC1CCC(NC(=O)C=2C(=NC=C(Cl)C=2)C)CC1 JRBVOUREXIRPPY-UHFFFAOYSA-N 0.000 claims 1
- KQQMWFWXNSJHJA-UHFFFAOYSA-N 5-chloro-n-[4-[[(5-ethyl-4-methyl-1h-pyrazol-3-yl)amino]methyl]cyclohexyl]-2-methylpyridine-3-carboxamide Chemical compound CC1=C(CC)NN=C1NCC1CCC(NC(=O)C=2C(=NC=C(Cl)C=2)C)CC1 KQQMWFWXNSJHJA-UHFFFAOYSA-N 0.000 claims 1
- 239000000275 Adrenocorticotropic Hormone Substances 0.000 claims 1
- CVWWTNXFLUGTDI-ZHTAKFGLSA-N CC(C(O)=O)c1ccc(NC[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)cc1 Chemical compound CC(C(O)=O)c1ccc(NC[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)cc1 CVWWTNXFLUGTDI-ZHTAKFGLSA-N 0.000 claims 1
- DLODGACIEXJIID-KOMQPUFPSA-N CC(C)(C)c1ccn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)n1 Chemical compound CC(C)(C)c1ccn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)n1 DLODGACIEXJIID-KOMQPUFPSA-N 0.000 claims 1
- WQYAOEVXNPHQHJ-JCNLHEQBSA-N CC(C)c1c(C)cnn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F Chemical compound CC(C)c1c(C)cnn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F WQYAOEVXNPHQHJ-JCNLHEQBSA-N 0.000 claims 1
- CSYALHPPMSVBIL-SAABIXHNSA-N CC(C)c1cc(C(C)C)n(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)n1 Chemical compound CC(C)c1cc(C(C)C)n(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)n1 CSYALHPPMSVBIL-SAABIXHNSA-N 0.000 claims 1
- XIRJFRYFIXCOCZ-SAABIXHNSA-N CC(C)c1cc(C)n(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(Cl)cnc2C)n1 Chemical compound CC(C)c1cc(C)n(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(Cl)cnc2C)n1 XIRJFRYFIXCOCZ-SAABIXHNSA-N 0.000 claims 1
- VFTPTHOIZIMBGU-SAABIXHNSA-N CC(C)c1cc(C)nn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(Cl)cnc1C Chemical compound CC(C)c1cc(C)nn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(Cl)cnc1C VFTPTHOIZIMBGU-SAABIXHNSA-N 0.000 claims 1
- FKFUKPZBLDIDCA-KOMQPUFPSA-N CC(C)c1cc(CO)nn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F Chemical compound CC(C)c1cc(CO)nn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F FKFUKPZBLDIDCA-KOMQPUFPSA-N 0.000 claims 1
- KTYIVOVFFAQTSQ-SAABIXHNSA-N CC(C)c1nn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(Cl)cnc2C)cc1C Chemical compound CC(C)c1nn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(Cl)cnc2C)cc1C KTYIVOVFFAQTSQ-SAABIXHNSA-N 0.000 claims 1
- VDHCHJQTFOXAKF-JCNLHEQBSA-N CC(C)c1nn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)cc1C Chemical compound CC(C)c1nn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)cc1C VDHCHJQTFOXAKF-JCNLHEQBSA-N 0.000 claims 1
- SIVDZRMKCXLRPY-CZIWCDLHSA-N CC1=NC=C(Cl)C=C1C(=O)N[C@@H]1CC[C@@H](CN2C=3CCCC=3C=N2)CC1 Chemical compound CC1=NC=C(Cl)C=C1C(=O)N[C@@H]1CC[C@@H](CN2C=3CCCC=3C=N2)CC1 SIVDZRMKCXLRPY-CZIWCDLHSA-N 0.000 claims 1
- UVKGWNIRLPNREG-CZIWCDLHSA-N CC1=NC=C(Cl)C=C1C(=O)N[C@@H]1CC[C@@H](CN2N=C3CCCC3=C2)CC1 Chemical compound CC1=NC=C(Cl)C=C1C(=O)N[C@@H]1CC[C@@H](CN2N=C3CCCC3=C2)CC1 UVKGWNIRLPNREG-CZIWCDLHSA-N 0.000 claims 1
- VCERYFYYVGYTNI-KOMQPUFPSA-N CCOC(=O)c1c(C)cnn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F Chemical compound CCOC(=O)c1c(C)cnn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F VCERYFYYVGYTNI-KOMQPUFPSA-N 0.000 claims 1
- PZRFQJADLUWQGZ-MQMHXKEQSA-N CCOC(=O)c1c(Cl)cnn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F Chemical compound CCOC(=O)c1c(Cl)cnn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F PZRFQJADLUWQGZ-MQMHXKEQSA-N 0.000 claims 1
- WLLGCGVEZFNTLJ-CTYIDZIISA-N CCOC(=O)c1ccn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)n1 Chemical compound CCOC(=O)c1ccn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)n1 WLLGCGVEZFNTLJ-CTYIDZIISA-N 0.000 claims 1
- BRXWMNWQXMTVID-CTYIDZIISA-N CCOC(=O)c1ccnn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F Chemical compound CCOC(=O)c1ccnn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F BRXWMNWQXMTVID-CTYIDZIISA-N 0.000 claims 1
- XZMXFOVTHOXSOH-KOMQPUFPSA-N CCOC(=O)c1nn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)cc1C Chemical compound CCOC(=O)c1nn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)cc1C XZMXFOVTHOXSOH-KOMQPUFPSA-N 0.000 claims 1
- VBHAOZNATJEEMB-JCNLHEQBSA-N CCc1c(C)cnn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(Cl)cnc1C Chemical compound CCc1c(C)cnn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(Cl)cnc1C VBHAOZNATJEEMB-JCNLHEQBSA-N 0.000 claims 1
- LMFKNZJLPGRGKR-KOMQPUFPSA-N CCc1c(C)cnn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F Chemical compound CCc1c(C)cnn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F LMFKNZJLPGRGKR-KOMQPUFPSA-N 0.000 claims 1
- FSQVOSCRZKKFOF-CTYIDZIISA-N CCc1c(Cl)c(C)nn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F Chemical compound CCc1c(Cl)c(C)nn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F FSQVOSCRZKKFOF-CTYIDZIISA-N 0.000 claims 1
- KUKANTJOKSAEMK-CZIWCDLHSA-N CCc1cc(C)n(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)n1 Chemical compound CCc1cc(C)n(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)n1 KUKANTJOKSAEMK-CZIWCDLHSA-N 0.000 claims 1
- CQDAKWJVFKETDG-KOMQPUFPSA-N CCc1cc(C)nn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F Chemical compound CCc1cc(C)nn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F CQDAKWJVFKETDG-KOMQPUFPSA-N 0.000 claims 1
- YRZWOGUFXLWUKM-CZIWCDLHSA-N CCc1cc(CC)n(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)n1 Chemical compound CCc1cc(CC)n(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)n1 YRZWOGUFXLWUKM-CZIWCDLHSA-N 0.000 claims 1
- VNUJFEHKOZBNKG-JCNLHEQBSA-N CCc1nn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(Cl)cnc2C)cc1C Chemical compound CCc1nn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(Cl)cnc2C)cc1C VNUJFEHKOZBNKG-JCNLHEQBSA-N 0.000 claims 1
- WYPKJBZTZFZUPF-CTYIDZIISA-N CCc1nn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)c(C)c1Cl Chemical compound CCc1nn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)c(C)c1Cl WYPKJBZTZFZUPF-CTYIDZIISA-N 0.000 claims 1
- KUHXDWVHYWXSOZ-CTYIDZIISA-N CCc1nn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)c(CC)c1Cl Chemical compound CCc1nn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)c(CC)c1Cl KUHXDWVHYWXSOZ-CTYIDZIISA-N 0.000 claims 1
- UXTJTLDUDAQOMQ-KOMQPUFPSA-N CCc1nn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)cc1C Chemical compound CCc1nn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)cc1C UXTJTLDUDAQOMQ-KOMQPUFPSA-N 0.000 claims 1
- UFNOQJNGEZPSNX-MQMHXKEQSA-N COc1c(Cl)c(C)nn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F Chemical compound COc1c(Cl)c(C)nn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F UFNOQJNGEZPSNX-MQMHXKEQSA-N 0.000 claims 1
- LUOQQPVHUYVFNA-KOMQPUFPSA-N COc1cc(C)n(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(Cl)cnc2C)n1 Chemical compound COc1cc(C)n(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(Cl)cnc2C)n1 LUOQQPVHUYVFNA-KOMQPUFPSA-N 0.000 claims 1
- ASLHIRDCUBBIEL-CTYIDZIISA-N COc1cc(C)n(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)n1 Chemical compound COc1cc(C)n(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)n1 ASLHIRDCUBBIEL-CTYIDZIISA-N 0.000 claims 1
- JOSMVOMZCLJNAS-KOMQPUFPSA-N COc1cc(C)nn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(Cl)cnc1C Chemical compound COc1cc(C)nn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(Cl)cnc1C JOSMVOMZCLJNAS-KOMQPUFPSA-N 0.000 claims 1
- KJEKFLMCRQCNRL-CTYIDZIISA-N COc1cc(C)nn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F Chemical compound COc1cc(C)nn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F KJEKFLMCRQCNRL-CTYIDZIISA-N 0.000 claims 1
- WYTQVDBYGFCFCU-CTYIDZIISA-N COc1ccc(Cl)c(NC[C@H]2CC[C@@H](CC2)NC(=O)c2cc(Cl)cnc2C)n1 Chemical compound COc1ccc(Cl)c(NC[C@H]2CC[C@@H](CC2)NC(=O)c2cc(Cl)cnc2C)n1 WYTQVDBYGFCFCU-CTYIDZIISA-N 0.000 claims 1
- MURHVXZELMNENA-RUCARUNLSA-N COc1ccc(cc1)-c1ccn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)n1 Chemical compound COc1ccc(cc1)-c1ccn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)n1 MURHVXZELMNENA-RUCARUNLSA-N 0.000 claims 1
- SCPATYFCJLYFTI-CTYIDZIISA-N COc1nn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(Cl)cnc2C)c(C)c1Cl Chemical compound COc1nn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(Cl)cnc2C)c(C)c1Cl SCPATYFCJLYFTI-CTYIDZIISA-N 0.000 claims 1
- LQOCDLGXBNNPRZ-MQMHXKEQSA-N COc1nn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)c(C)c1Cl Chemical compound COc1nn(C[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)c(C)c1Cl LQOCDLGXBNNPRZ-MQMHXKEQSA-N 0.000 claims 1
- KEVHTHIFWWAZOE-RHDGDCLCSA-N Cc1[nH]nc(NC[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)c1-c1ccc(F)cc1 Chemical compound Cc1[nH]nc(NC[C@H]2CC[C@@H](CC2)NC(=O)c2cc(ccc2Cl)C(F)(F)F)c1-c1ccc(F)cc1 KEVHTHIFWWAZOE-RHDGDCLCSA-N 0.000 claims 1
- NICNGJBCHOEQET-MQMHXKEQSA-N Cc1c(Cl)c(nn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(Cl)cnc1C)C(F)(F)F Chemical compound Cc1c(Cl)c(nn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(Cl)cnc1C)C(F)(F)F NICNGJBCHOEQET-MQMHXKEQSA-N 0.000 claims 1
- XDRNJBXWFMSCQY-KOMQPUFPSA-N Cc1c2COCCc2nn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F Chemical compound Cc1c2COCCc2nn1C[C@H]1CC[C@@H](CC1)NC(=O)c1cc(ccc1Cl)C(F)(F)F XDRNJBXWFMSCQY-KOMQPUFPSA-N 0.000 claims 1
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- 2011-01-31 ES ES11701824.2T patent/ES2527849T3/es active Active
- 2011-01-31 WO PCT/EP2011/051293 patent/WO2011095450A1/en not_active Ceased
- 2011-01-31 US US13/576,040 patent/US8835444B2/en not_active Expired - Fee Related
- 2011-01-31 EP EP11701824.2A patent/EP2531490B1/en not_active Not-in-force
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