JP2013516415A5 - - Google Patents
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- Publication number
- JP2013516415A5 JP2013516415A5 JP2012547159A JP2012547159A JP2013516415A5 JP 2013516415 A5 JP2013516415 A5 JP 2013516415A5 JP 2012547159 A JP2012547159 A JP 2012547159A JP 2012547159 A JP2012547159 A JP 2012547159A JP 2013516415 A5 JP2013516415 A5 JP 2013516415A5
- Authority
- JP
- Japan
- Prior art keywords
- bis
- phenylene
- diyldi
- pyrrolidinecarboxamide
- oxazole
- 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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- 229910052757 nitrogen Inorganic materials 0.000 claims 312
- 125000000217 alkyl group Chemical group 0.000 claims 111
- -1 —NHR p Chemical group 0.000 claims 62
- 239000001257 hydrogen Substances 0.000 claims 58
- 229910052739 hydrogen Inorganic materials 0.000 claims 58
- 125000003118 aryl group Chemical group 0.000 claims 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 31
- 125000001072 heteroaryl group Chemical group 0.000 claims 30
- 125000001424 substituent group Chemical group 0.000 claims 30
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 25
- 229910052736 halogen Inorganic materials 0.000 claims 23
- 150000002367 halogens Chemical class 0.000 claims 23
- 125000000623 heterocyclic group Chemical group 0.000 claims 22
- 150000003839 salts Chemical class 0.000 claims 20
- 239000012453 solvate Substances 0.000 claims 20
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
- 150000002431 hydrogen Chemical class 0.000 claims 15
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 12
- OWZZLWKRUOYHAU-JEGXQRANSA-N (2s)-1-[(2r)-2-(dimethylamino)-2-phenylacetyl]-n-[4-[5-[4-[[(2s)-1-[(2r)-2-hydroxy-2-phenylacetyl]pyrrolidine-2-carbonyl]amino]phenyl]furan-2-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound C1([C@@H](O)C(=O)N2CCC[C@H]2C(=O)NC2=CC=C(C=C2)C2=CC=C(O2)C2=CC=C(C=C2)NC(=O)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)=CC=CC=C1 OWZZLWKRUOYHAU-JEGXQRANSA-N 0.000 claims 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 8
- 125000002947 alkylene group Chemical group 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 7
- 229910052717 sulfur Chemical group 0.000 claims 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 239000001294 propane Substances 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- IBTDJGOEYUJEHP-UHFFFAOYSA-N C=1C=C(F)C=C(F)C=1C(N(C)C)C(=O)N1CCCC1C(=O)NC(C=C1)=CC=C1C(O1)=CN=C1C(C=C1)=CC=C1NC(=O)C1CCCN1C(=O)C(N(C)C)C1=CC=C(F)C=C1F Chemical compound C=1C=C(F)C=C(F)C=1C(N(C)C)C(=O)N1CCCC1C(=O)NC(C=C1)=CC=C1C(O1)=CN=C1C(C=C1)=CC=C1NC(=O)C1CCCN1C(=O)C(N(C)C)C1=CC=C(F)C=C1F IBTDJGOEYUJEHP-UHFFFAOYSA-N 0.000 claims 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims 2
- GBDVKSQVQHLOGA-PAIGMYNKSA-N 1-[(2S)-oxolane-2-carbonyl]-N-[4-[5-[4-[[1-[(2S)-oxolane-2-carbonyl]pyrrolidine-2-carbonyl]amino]phenyl]-1,3,4-oxadiazol-2-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound C1CCN(C(=O)[C@H]2OCCC2)C1C(=O)NC(C=C1)=CC=C1C(O1)=NN=C1C(C=C1)=CC=C1NC(=O)C1CCCN1C(=O)[C@@H]1CCCO1 GBDVKSQVQHLOGA-PAIGMYNKSA-N 0.000 claims 2
- JFCDUMKOXHHMTP-UHFFFAOYSA-N 2-benzylpyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1CC1=CC=CC=C1 JFCDUMKOXHHMTP-UHFFFAOYSA-N 0.000 claims 2
- GULMJNUJAVNDBJ-UHFFFAOYSA-N 2-methylpyrrolidine-1-carboxylic acid Chemical compound CC1CCCN1C(O)=O GULMJNUJAVNDBJ-UHFFFAOYSA-N 0.000 claims 2
- NQXSJMZRLAAINC-UHFFFAOYSA-N C1C(O)CC(C(=O)NC=2C=CC(=CC=2)C2=C(NC=N2)C=2C=CC(NC(=O)C3N(CC(O)C3)C(=O)CC=3C=CC=CC=3)=CC=2)N1C(=O)CC1=CC=CC=C1 Chemical compound C1C(O)CC(C(=O)NC=2C=CC(=CC=2)C2=C(NC=N2)C=2C=CC(NC(=O)C3N(CC(O)C3)C(=O)CC=3C=CC=CC=3)=CC=2)N1C(=O)CC1=CC=CC=C1 NQXSJMZRLAAINC-UHFFFAOYSA-N 0.000 claims 2
- HLHWILUOGDVJOK-UHFFFAOYSA-N C1CCC(C(=O)NC=2C=CC(=CC=2)C=2OC(=NC=2)C=2C=CC(NC(=O)C3N(CCC3)C(=O)CC3CC3)=CC=2)N1C(=O)CC1CC1 Chemical compound C1CCC(C(=O)NC=2C=CC(=CC=2)C=2OC(=NC=2)C=2C=CC(NC(=O)C3N(CCC3)C(=O)CC3CC3)=CC=2)N1C(=O)CC1CC1 HLHWILUOGDVJOK-UHFFFAOYSA-N 0.000 claims 2
- HNOFUQBYRPYCLA-NLBWKBLJSA-N CO[C@@H](C(N(CCC1)C1C(NC(C=C1)=CC=C1C1=CN=C(C(C=C2)=CC=C2NC(C(CCC2)N2C([C@@H](C2=CC=CC=C2)OC)=O)=O)O1)=O)=O)C1=CC=CC=C1 Chemical compound CO[C@@H](C(N(CCC1)C1C(NC(C=C1)=CC=C1C1=CN=C(C(C=C2)=CC=C2NC(C(CCC2)N2C([C@@H](C2=CC=CC=C2)OC)=O)=O)O1)=O)=O)C1=CC=CC=C1 HNOFUQBYRPYCLA-NLBWKBLJSA-N 0.000 claims 2
- XGYVNSHZVNLRLN-FPMWXBJSSA-N C[C@H](NC(=O)C(C)(O)c1ccccc1)C(=O)Nc1ccc(cc1)-c1cc([nH]n1)-c1ccc(NC(=O)[C@H](C)NC(=O)C(C)(O)c2ccccc2)cc1 Chemical compound C[C@H](NC(=O)C(C)(O)c1ccccc1)C(=O)Nc1ccc(cc1)-c1cc([nH]n1)-c1ccc(NC(=O)[C@H](C)NC(=O)C(C)(O)c2ccccc2)cc1 XGYVNSHZVNLRLN-FPMWXBJSSA-N 0.000 claims 2
- GISXMZMFIWNHRK-FPMWXBJSSA-N C[C@H](NC(=O)C(C)(O)c1ccccc1)C(=O)Nc1ccc(cc1)-c1cnc(o1)-c1ccc(NC(=O)[C@H](C)NC(=O)C(C)(O)c2ccccc2)cc1 Chemical compound C[C@H](NC(=O)C(C)(O)c1ccccc1)C(=O)Nc1ccc(cc1)-c1cnc(o1)-c1ccc(NC(=O)[C@H](C)NC(=O)C(C)(O)c2ccccc2)cc1 GISXMZMFIWNHRK-FPMWXBJSSA-N 0.000 claims 2
- QUFVLNKWNMVQPD-KLTKIEITSA-N O[C@@H](C(N1C(CC(NC2=CC=C(C(C=C3)=CC=C3NC(CC(CCC3)N3C([C@@H](C3=CC=CC=C3)O)=O)=O)O2)=O)CCC1)=O)C1=CC=CC=C1 Chemical compound O[C@@H](C(N1C(CC(NC2=CC=C(C(C=C3)=CC=C3NC(CC(CCC3)N3C([C@@H](C3=CC=CC=C3)O)=O)=O)O2)=O)CCC1)=O)C1=CC=CC=C1 QUFVLNKWNMVQPD-KLTKIEITSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- FWTXWYXPXGKVJG-UHFFFAOYSA-N atrolactamide Chemical compound NC(=O)C(O)(C)C1=CC=CC=C1 FWTXWYXPXGKVJG-UHFFFAOYSA-N 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 239000004202 carbamide Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 239000001301 oxygen Chemical group 0.000 claims 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 2
- VLJNHYLEOZPXFW-UHFFFAOYSA-N pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1 VLJNHYLEOZPXFW-UHFFFAOYSA-N 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- GLGUEUISIUMNBP-VMPREFPWSA-N (2s)-1-[2-(1h-imidazol-5-yl)acetyl]-n-[4-[2-[4-[[(2s)-1-[2-(1h-imidazol-5-yl)acetyl]pyrrolidine-2-carbonyl]amino]phenyl]-1,3-oxazol-5-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CCC1)C(=O)NC=1C=CC(=CC=1)C=1OC(=NC=1)C=1C=CC(NC(=O)[C@H]2N(CCC2)C(=O)CC=2NC=NC=2)=CC=1)C(=O)CC1=CNC=N1 GLGUEUISIUMNBP-VMPREFPWSA-N 0.000 claims 1
- KYONFLKOAJDZFM-KYJUHHDHSA-N (2s)-1-acetyl-n-[4-[2-[4-[[(2s)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]phenyl]-1,3-oxazol-5-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound CC(=O)N1CCC[C@H]1C(=O)NC1=CC=C(C=2OC(=NC=2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)CC=3C=CC=CC=3)=CC=2)C=C1 KYONFLKOAJDZFM-KYJUHHDHSA-N 0.000 claims 1
- OQCPDQSVKMVDFC-CONSDPRKSA-N (2s)-1-acetyl-n-[4-[2-methyl-4-[4-[[(2s)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]phenyl]-1,3-thiazol-5-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound CC(=O)N1CCC[C@H]1C(=O)NC1=CC=C(C2=C(N=C(C)S2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)CC=3C=CC=CC=3)=CC=2)C=C1 OQCPDQSVKMVDFC-CONSDPRKSA-N 0.000 claims 1
- JYHUMLLYOIIBQM-CONSDPRKSA-N (2s)-1-acetyl-n-[4-[4-[4-[[(2s)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]phenyl]-1,3-thiazol-2-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound CC(=O)N1CCC[C@H]1C(=O)NC1=CC=C(C=2SC=C(N=2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)CC=3C=CC=CC=3)=CC=2)C=C1 JYHUMLLYOIIBQM-CONSDPRKSA-N 0.000 claims 1
- JOQXAQFWUZZRTF-VMPREFPWSA-N (2s)-1-acetyl-n-[4-[5-[4-[[(2s)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]phenyl]-1,3,4-oxadiazol-2-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound CC(=O)N1CCC[C@H]1C(=O)NC1=CC=C(C=2OC(=NN=2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)CC=3C=CC=CC=3)=CC=2)C=C1 JOQXAQFWUZZRTF-VMPREFPWSA-N 0.000 claims 1
- WYIQQXYQFCCJFF-KYJUHHDHSA-N (2s)-1-acetyl-n-[4-[5-[4-[[(2s)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]phenyl]-1,3-oxazol-2-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound CC(=O)N1CCC[C@H]1C(=O)NC1=CC=C(C=2OC(=CN=2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)CC=3C=CC=CC=3)=CC=2)C=C1 WYIQQXYQFCCJFF-KYJUHHDHSA-N 0.000 claims 1
- DZJDTIHPHLMWPC-ACHIHNKUSA-N (2s)-1-acetyl-n-[4-[5-[4-[[(2s)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]phenyl]-1h-pyrazol-3-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound CC(=O)N1CCC[C@H]1C(=O)NC1=CC=C(C=2NN=C(C=2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)CC=3C=CC=CC=3)=CC=2)C=C1 DZJDTIHPHLMWPC-ACHIHNKUSA-N 0.000 claims 1
- VBBWYFTXAXGAQS-NSOVKSMOSA-N (2s)-1-acetyl-n-[4-[5-[4-[[(2s)-1-(2-pyridin-3-ylacetyl)pyrrolidine-2-carbonyl]amino]phenyl]-1,3,4-oxadiazol-2-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound CC(=O)N1CCC[C@H]1C(=O)NC1=CC=C(C=2OC(=NN=2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)CC=3C=NC=CC=3)=CC=2)C=C1 VBBWYFTXAXGAQS-NSOVKSMOSA-N 0.000 claims 1
- PQKWPXVRMYHUKR-UHFFFAOYSA-N 1-(1,3-benzodioxole-5-carbonyl)pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1C(=O)C1=CC=C(OCO2)C2=C1 PQKWPXVRMYHUKR-UHFFFAOYSA-N 0.000 claims 1
- ZMMZGEKGAVBUAI-UHFFFAOYSA-N 1-(1-benzofuran-2-carbonyl)-N-[4-[4-[4-[[1-(1-benzofuran-2-carbonyl)pyrrolidine-2-carbonyl]amino]phenyl]-1H-imidazol-5-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound C1=CC=C2OC(C(=O)N3CCCC3C(NC=3C=CC(=CC=3)C3=C(NC=N3)C=3C=CC(NC(=O)C4N(CCC4)C(=O)C=4OC5=CC=CC=C5C=4)=CC=3)=O)=CC2=C1 ZMMZGEKGAVBUAI-UHFFFAOYSA-N 0.000 claims 1
- VUOYCZMKODGCKP-UHFFFAOYSA-N 1-(2-methoxy-2-phenylacetyl)-4-[(2-methylpropan-2-yl)oxy]pyrrolidine-2-carboxamide Chemical compound C(C)(C)(C)OC1CC(N(C1)C(C(C1=CC=CC=C1)OC)=O)C(=O)N VUOYCZMKODGCKP-UHFFFAOYSA-N 0.000 claims 1
- NTDOGZXJIQGMJA-UHFFFAOYSA-N 1-(2-methylpropanoyl)-N-[4-[3-[4-[[1-(2-methylpropanoyl)pyrrolidine-2-carbonyl]amino]phenyl]-1H-pyrazol-5-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound CC(C)C(=O)N1CCCC1C(=O)Nc1ccc(cc1)-c1cc([nH]n1)-c1ccc(NC(=O)C2CCCN2C(=O)C(C)C)cc1 NTDOGZXJIQGMJA-UHFFFAOYSA-N 0.000 claims 1
- SOGBGOPTHHABCU-UHFFFAOYSA-N 1-(2-oxo-2-phenylacetyl)-N-[4-[2-[4-[[1-(2-oxo-2-phenylacetyl)pyrrolidine-2-carbonyl]amino]phenyl]-1,3-oxazol-5-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound C1CCN(C(=O)C(=O)C=2C=CC=CC=2)C1C(=O)NC(C=C1)=CC=C1C(O1)=CN=C1C(C=C1)=CC=C1NC(=O)C1CCCN1C(=O)C(=O)C1=CC=CC=C1 SOGBGOPTHHABCU-UHFFFAOYSA-N 0.000 claims 1
- UQQPRDWCCUYMSE-UHFFFAOYSA-N 1-(2-oxo-2-phenylacetyl)-N-[4-[3-[4-[[1-(2-oxo-2-phenylacetyl)pyrrolidine-2-carbonyl]amino]phenyl]-1H-pyrazol-5-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound O=C(Nc1ccc(cc1)-c1cc([nH]n1)-c1ccc(NC(=O)C2CCCN2C(=O)C(=O)c2ccccc2)cc1)C1CCCN1C(=O)C(=O)c1ccccc1 UQQPRDWCCUYMSE-UHFFFAOYSA-N 0.000 claims 1
- LTSVJTNWOOAGTJ-UHFFFAOYSA-N 1-(2-phenylacetyl)-N-[4-[5-[4-[[1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]phenyl]-2H-triazol-4-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound O=C(Cc1ccccc1)N1CCCC1C(=O)Nc1ccc(cc1)-c1n[nH]nc1-c1ccc(NC(=O)C2CCCN2C(=O)Cc2ccccc2)cc1 LTSVJTNWOOAGTJ-UHFFFAOYSA-N 0.000 claims 1
- SLVUWFRBVVAAEI-UHFFFAOYSA-N 1-(2-phenylacetyl)-n-[4-[5-[4-[[1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]phenyl]-1,3,4-oxadiazol-2-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound C1CCC(C(=O)NC=2C=CC(=CC=2)C=2OC(=NN=2)C=2C=CC(NC(=O)C3N(CCC3)C(=O)CC=3C=CC=CC=3)=CC=2)N1C(=O)CC1=CC=CC=C1 SLVUWFRBVVAAEI-UHFFFAOYSA-N 0.000 claims 1
- OLFPUHDHQIBXNH-UHFFFAOYSA-N 1-(2-phenylacetyl)pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1C(=O)CC1=CC=CC=C1 OLFPUHDHQIBXNH-UHFFFAOYSA-N 0.000 claims 1
- SAANOXOPPLPZQX-UHFFFAOYSA-N 1-(2-pyridin-3-ylacetyl)-N-[4-[5-[4-[[1-(2-pyridin-3-ylacetyl)pyrrolidine-2-carbonyl]amino]phenyl]-1,3,4-oxadiazol-2-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound C1CCC(C(=O)NC=2C=CC(=CC=2)C=2OC(=NN=2)C=2C=CC(NC(=O)C3N(CCC3)C(=O)CC=3C=NC=CC=3)=CC=2)N1C(=O)CC1=CC=CN=C1 SAANOXOPPLPZQX-UHFFFAOYSA-N 0.000 claims 1
- FFVZTQZKFFHVBX-UHFFFAOYSA-N 1-(2-thiophen-2-ylacetyl)-N-[4-[5-[4-[[1-(2-thiophen-2-ylacetyl)pyrrolidine-2-carbonyl]amino]phenyl]-1,3,4-oxadiazol-2-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound C1CCC(C(=O)NC=2C=CC(=CC=2)C=2OC(=NN=2)C=2C=CC(NC(=O)C3N(CCC3)C(=O)CC=3SC=CC=3)=CC=2)N1C(=O)CC1=CC=CS1 FFVZTQZKFFHVBX-UHFFFAOYSA-N 0.000 claims 1
- SUVGLYYTUGLOCF-UHFFFAOYSA-N 1-(cyclohexanecarbonyl)-4-[(2-methylpropan-2-yl)oxy]pyrrolidine-2-carboxamide Chemical compound C(C)(C)(C)OC1CC(N(C1)C(=O)C1CCCCC1)C(=O)N SUVGLYYTUGLOCF-UHFFFAOYSA-N 0.000 claims 1
- BXGJRZXDMFPRTF-UHFFFAOYSA-N 1-(cyclopropanecarbonyl)-N-[4-[2-[4-[[1-(cyclopropanecarbonyl)pyrrolidine-2-carbonyl]amino]phenyl]-1,3-oxazol-5-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound C1CCN(C(=O)C2CC2)C1C(=O)NC(C=C1)=CC=C1C(O1)=CN=C1C(C=C1)=CC=C1NC(=O)C1CCCN1C(=O)C1CC1 BXGJRZXDMFPRTF-UHFFFAOYSA-N 0.000 claims 1
- OSBDOZGOISPFEH-UHFFFAOYSA-N 1-(cyclopropanecarbonyl)-N-[4-[3-[4-[[1-(cyclopropanecarbonyl)pyrrolidine-2-carbonyl]amino]phenyl]-1H-pyrazol-5-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound O=C(Nc1ccc(cc1)-c1cc([nH]n1)-c1ccc(NC(=O)C2CCCN2C(=O)C2CC2)cc1)C1CCCN1C(=O)C1CC1 OSBDOZGOISPFEH-UHFFFAOYSA-N 0.000 claims 1
- QXIWAHGGSVLVLW-UHFFFAOYSA-N 1-(cyclopropanecarbonyl)-N-[4-[5-[4-[[1-(cyclopropanecarbonyl)pyrrolidine-2-carbonyl]amino]phenyl]-2-methylpyrazol-3-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound CN1N=C(C=2C=CC(NC(=O)C3N(CCC3)C(=O)C3CC3)=CC=2)C=C1C(C=C1)=CC=C1NC(=O)C1CCCN1C(=O)C1CC1 QXIWAHGGSVLVLW-UHFFFAOYSA-N 0.000 claims 1
- OXZWPMAWPYPRGB-UHFFFAOYSA-N 1-(pyridine-4-carbonyl)-N-[4-[2-[4-[[1-(pyridine-4-carbonyl)pyrrolidine-2-carbonyl]amino]phenyl]-1,3-oxazol-5-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound C1CCN(C(=O)C=2C=CN=CC=2)C1C(=O)NC(C=C1)=CC=C1C(O1)=CN=C1C(C=C1)=CC=C1NC(=O)C1CCCN1C(=O)C1=CC=NC=C1 OXZWPMAWPYPRGB-UHFFFAOYSA-N 0.000 claims 1
- QMQQDHXAUDMKNK-UHFFFAOYSA-N 1-[(2-phenylacetyl)amino]-n-[4-[2-[4-[[1-[(2-phenylacetyl)amino]cyclopropanecarbonyl]amino]phenyl]-1,3-oxazol-5-yl]phenyl]cyclopropane-1-carboxamide Chemical compound C1CC1(C(=O)NC=1C=CC(=CC=1)C=1OC(=NC=1)C=1C=CC(NC(=O)C2(CC2)NC(=O)CC=2C=CC=CC=2)=CC=1)NC(=O)CC1=CC=CC=C1 QMQQDHXAUDMKNK-UHFFFAOYSA-N 0.000 claims 1
- PJXPFVOTOJLFOK-KFTPUPIBSA-N 1-[(2S,3R)-2-(dimethylamino)-3-hydroxy-3-phenylpropanoyl]pyrrolidine-2-carboxamide Chemical compound C1([C@@H](O)[C@H](N(C)C)C(=O)N2C(CCC2)C(N)=O)=CC=CC=C1 PJXPFVOTOJLFOK-KFTPUPIBSA-N 0.000 claims 1
- PJXPFVOTOJLFOK-TTZKSVMKSA-N 1-[(2S,3S)-2-(dimethylamino)-3-hydroxy-3-phenylpropanoyl]pyrrolidine-2-carboxamide Chemical compound C1([C@H](O)[C@H](N(C)C)C(=O)N2C(CCC2)C(N)=O)=CC=CC=C1 PJXPFVOTOJLFOK-TTZKSVMKSA-N 0.000 claims 1
- VZVLWKNNQFGQMR-IMDLXVGASA-N 1-[(2r)-2-acetamido-2-phenylacetyl]-n-[4-[2-[4-[[1-[(2r)-2-acetamido-2-phenylacetyl]pyrrolidine-2-carbonyl]amino]phenyl]-1,3-oxazol-5-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound C1([C@@H](NC(C)=O)C(=O)N2CCCC2C(=O)NC2=CC=C(C=C2)C2=NC=C(O2)C2=CC=C(C=C2)NC(=O)C2CCCN2C(=O)[C@H](NC(=O)C)C=2C=CC=CC=2)=CC=CC=C1 VZVLWKNNQFGQMR-IMDLXVGASA-N 0.000 claims 1
- WMWYPNRNWAOJNM-RJLUKDKGSA-N 1-[(2r)-2-acetamido-2-phenylacetyl]-n-[4-[3-[4-[[1-[(2r)-2-acetamido-2-phenylacetyl]pyrrolidine-2-carbonyl]amino]phenyl]-1h-pyrazol-5-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound C1([C@@H](NC(C)=O)C(=O)N2CCCC2C(=O)NC2=CC=C(C=C2)C2=CC(=NN2)C2=CC=C(C=C2)NC(=O)C2CCCN2C(=O)[C@H](NC(=O)C)C=2C=CC=CC=2)=CC=CC=C1 WMWYPNRNWAOJNM-RJLUKDKGSA-N 0.000 claims 1
- SCYLYSQNUMZGCM-ZBUALCFQSA-N 1-[(3r)-1-(2-hydroxy-2-phenylpropanoyl)pyrrolidin-3-yl]-3-[4-[2-[4-[[(3r)-1-(2-hydroxy-2-phenylpropanoyl)pyrrolidin-3-yl]carbamoylamino]phenyl]-1,3-oxazol-5-yl]phenyl]urea Chemical compound C([C@H](C1)NC(=O)NC2=CC=C(C=C2)C2=NC=C(O2)C2=CC=C(C=C2)NC(=O)N[C@@H]2CCN(C2)C(=O)C(O)(C)C=2C=CC=CC=2)CN1C(=O)C(C)(O)C1=CC=CC=C1 SCYLYSQNUMZGCM-ZBUALCFQSA-N 0.000 claims 1
- OCGPRSMFEBCNRN-IVLNXHDYSA-N 1-[(3r)-1-[(2r)-2-(dimethylamino)-2-phenylacetyl]pyrrolidin-3-yl]-3-[4-[2-[4-[[(3r)-1-[(2r)-2-(dimethylamino)-2-phenylacetyl]pyrrolidin-3-yl]carbamoylamino]phenyl]-1,3-oxazol-5-yl]phenyl]urea Chemical compound C1([C@@H](N(C)C)C(=O)N2CC[C@H](C2)NC(=O)NC2=CC=C(C=C2)C2=NC=C(O2)C2=CC=C(C=C2)NC(=O)N[C@@H]2CCN(C2)C(=O)[C@H](N(C)C)C=2C=CC=CC=2)=CC=CC=C1 OCGPRSMFEBCNRN-IVLNXHDYSA-N 0.000 claims 1
- DGKUEWOSFLOVCC-UHFFFAOYSA-N 1-[3-(4-bromophenyl)-2-(dimethylamino)propanoyl]pyrrolidine-2-carboxamide Chemical compound C1CCC(C(N)=O)N1C(=O)C(N(C)C)CC1=CC=C(Br)C=C1 DGKUEWOSFLOVCC-UHFFFAOYSA-N 0.000 claims 1
- QIWVRLDULGDBNJ-UHFFFAOYSA-N 1-acetyl-N-[4-[5-[4-[(1-acetylpyrrolidine-2-carbonyl)amino]phenyl]-2-methylpyrazol-3-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound CC(=O)N1CCCC1C(=O)NC1=CC=C(C2=NN(C)C(C=3C=CC(NC(=O)C4N(CCC4)C(C)=O)=CC=3)=C2)C=C1 QIWVRLDULGDBNJ-UHFFFAOYSA-N 0.000 claims 1
- ZSOIIGYMKMWVEZ-UHFFFAOYSA-N 1-acetyl-N-[4-[5-[4-[(1-acetylpyrrolidine-2-carbonyl)amino]phenyl]thiophen-2-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound CC(=O)N1CCCC1C(=O)NC1=CC=C(C=2SC(=CC=2)C=2C=CC(NC(=O)C3N(CCC3)C(C)=O)=CC=2)C=C1 ZSOIIGYMKMWVEZ-UHFFFAOYSA-N 0.000 claims 1
- PREOKNWRVNMFDF-UHFFFAOYSA-N 1-propanoyl-N-[4-[2-[4-[(1-propanoylpyrrolidine-2-carbonyl)amino]phenyl]-1,3-oxazol-5-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound CCC(=O)N1CCCC1C(=O)NC1=CC=C(C=2OC(=NC=2)C=2C=CC(NC(=O)C3N(CCC3)C(=O)CC)=CC=2)C=C1 PREOKNWRVNMFDF-UHFFFAOYSA-N 0.000 claims 1
- LRVYAVBKCCEBFZ-UHFFFAOYSA-N 1-propanoyl-N-[4-[3-[4-[(1-propanoylpyrrolidine-2-carbonyl)amino]phenyl]-1H-pyrazol-5-yl]phenyl]pyrrolidine-2-carboxamide Chemical compound CCC(=O)N1CCCC1C(=O)Nc1ccc(cc1)-c1cc([nH]n1)-c1ccc(NC(=O)C2CCCN2C(=O)CC)cc1 LRVYAVBKCCEBFZ-UHFFFAOYSA-N 0.000 claims 1
- RHNHJPBRIBWGTL-PXLJZGITSA-N 2-[4,5-bis[4-[[(2s)-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]amino]phenyl]-1,3-oxazol-2-yl]acetic acid Chemical compound C([C@H]1C(=O)NC2=CC=C(C=C2)C2=C(N=C(O2)CC(=O)O)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)OCC=3C=CC=CC=3)=CC=2)CCN1C(=O)OCC1=CC=CC=C1 RHNHJPBRIBWGTL-PXLJZGITSA-N 0.000 claims 1
- YOYDHOKKIWWDOB-DQEYMECFSA-N 2-[4,5-bis[4-[[(2s)-2-(phenylmethoxycarbonylamino)propanoyl]amino]phenyl]-1,3-oxazol-2-yl]acetic acid Chemical compound N([C@@H](C)C(=O)NC=1C=CC(=CC=1)C1=C(OC(CC(O)=O)=N1)C=1C=CC(NC(=O)[C@H](C)NC(=O)OCC=2C=CC=CC=2)=CC=1)C(=O)OCC1=CC=CC=C1 YOYDHOKKIWWDOB-DQEYMECFSA-N 0.000 claims 1
- IIKAAJGUSWSGMS-UHFFFAOYSA-N 2-azabicyclo[3.1.0]hexane-2-carboxylic acid Chemical compound OC(=O)N1CCC2CC12 IIKAAJGUSWSGMS-UHFFFAOYSA-N 0.000 claims 1
- XLCCKHJJXQQTRX-ROUUACIJSA-N 2-chloro-n-[(2s)-1-[4-[5-[4-[[(2s)-2-[(2-chloro-6-methoxypyridine-4-carbonyl)amino]propanoyl]amino]phenyl]-1,3,4-oxadiazol-2-yl]anilino]-1-oxopropan-2-yl]-6-methoxypyridine-4-carboxamide Chemical compound ClC1=NC(OC)=CC(C(=O)N[C@@H](C)C(=O)NC=2C=CC(=CC=2)C=2OC(=NN=2)C=2C=CC(NC(=O)[C@H](C)NC(=O)C=3C=C(OC)N=C(Cl)C=3)=CC=2)=C1 XLCCKHJJXQQTRX-ROUUACIJSA-N 0.000 claims 1
- OABFPFBEKPDCES-UHFFFAOYSA-N 3-[(2-methylpropan-2-yl)oxy]pyrrolidine-1-carboxylic acid Chemical compound CC(C)(C)OC1CCN(C(O)=O)C1 OABFPFBEKPDCES-UHFFFAOYSA-N 0.000 claims 1
- QUSGVERULOBSEK-DQEYMECFSA-N 3-chloro-n-[(2s)-1-[4-[3-[4-[[(2s)-2-[(3-chloronaphthalene-1-carbonyl)amino]propanoyl]amino]phenyl]-1h-pyrazol-5-yl]anilino]-1-oxopropan-2-yl]naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N[C@@H](C)C(=O)NC3=CC=C(C=C3)C3=CC(=NN3)C3=CC=C(C=C3)NC(=O)[C@@H](NC(=O)C=3C4=CC=CC=C4C=C(Cl)C=3)C)=CC(Cl)=CC2=C1 QUSGVERULOBSEK-DQEYMECFSA-N 0.000 claims 1
- TYGXVBSCARFDGS-VXKWHMMOSA-N 3-chloro-n-[(2s)-1-[4-[5-[4-[[(2s)-2-[(3-chloro-5-methoxyisoquinoline-1-carbonyl)amino]propanoyl]amino]phenyl]-1,3,4-oxadiazol-2-yl]anilino]-1-oxopropan-2-yl]-5-methoxyisoquinoline-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N[C@@H](C)C(=O)NC3=CC=C(C=C3)C3=NN=C(O3)C3=CC=C(C=C3)NC(=O)[C@H](C)NC(=O)C3=C4C=CC=C(C4=CC(Cl)=N3)OC)=NC(Cl)=CC2=C1OC TYGXVBSCARFDGS-VXKWHMMOSA-N 0.000 claims 1
- DZHIDLKQOOQXJE-VXKWHMMOSA-N 3-chloro-n-[(2s)-1-[4-[5-[4-[[(2s)-2-[(3-chloroisoquinoline-1-carbonyl)amino]propanoyl]amino]phenyl]-1,3,4-oxadiazol-2-yl]anilino]-1-oxopropan-2-yl]isoquinoline-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N[C@@H](C)C(=O)NC3=CC=C(C=C3)C3=NN=C(O3)C3=CC=C(C=C3)NC(=O)[C@@H](NC(=O)C=3C4=CC=CC=C4C=C(Cl)N=3)C)=NC(Cl)=CC2=C1 DZHIDLKQOOQXJE-VXKWHMMOSA-N 0.000 claims 1
- VNHVAXJTZLISBP-UHFFFAOYSA-N 3-methyl-N-[4-[2-[4-[[3-methyl-2-[(2-phenylacetyl)amino]butanoyl]amino]phenyl]-1,3-oxazol-5-yl]phenyl]-2-[(2-phenylacetyl)amino]butanamide Chemical compound C=1C=C(C=2OC(=NC=2)C=2C=CC(NC(=O)C(NC(=O)CC=3C=CC=CC=3)C(C)C)=CC=2)C=CC=1NC(=O)C(C(C)C)NC(=O)CC1=CC=CC=C1 VNHVAXJTZLISBP-UHFFFAOYSA-N 0.000 claims 1
- OUSIJVYAFIKPIQ-UHFFFAOYSA-N 3-methylsulfanyl-N-[4-[2-[4-[[3-methylsulfanyl-2-[(2-phenylacetyl)amino]propanoyl]amino]phenyl]-1,3-oxazol-5-yl]phenyl]-2-[(2-phenylacetyl)amino]propanamide Chemical compound C=1C=C(C=2OC(=NC=2)C=2C=CC(NC(=O)C(CSC)NC(=O)CC=3C=CC=CC=3)=CC=2)C=CC=1NC(=O)C(CSC)NC(=O)CC1=CC=CC=C1 OUSIJVYAFIKPIQ-UHFFFAOYSA-N 0.000 claims 1
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- AHPVWJNUGFEMLK-ROUUACIJSA-N 4-chloro-n-[(2s)-1-[4-[5-[4-[[(2s)-2-[(4-chloropyridine-2-carbonyl)amino]propanoyl]amino]phenyl]-1,3,4-oxadiazol-2-yl]anilino]-1-oxopropan-2-yl]pyridine-2-carboxamide Chemical compound N([C@@H](C)C(=O)NC=1C=CC(=CC=1)C=1OC(=NN=1)C=1C=CC(NC(=O)[C@H](C)NC(=O)C=2N=CC=C(Cl)C=2)=CC=1)C(=O)C1=CC(Cl)=CC=N1 AHPVWJNUGFEMLK-ROUUACIJSA-N 0.000 claims 1
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- ZGCZVUIFKKCHHE-UHFFFAOYSA-N 4-methoxy-N-[4-[2-[4-[[4-methoxy-2-[(2-phenylacetyl)amino]butanoyl]amino]phenyl]-1,3-oxazol-5-yl]phenyl]-2-[(2-phenylacetyl)amino]butanamide Chemical compound C=1C=C(C=2OC(=NC=2)C=2C=CC(NC(=O)C(CCOC)NC(=O)CC=3C=CC=CC=3)=CC=2)C=CC=1NC(=O)C(CCOC)NC(=O)CC1=CC=CC=C1 ZGCZVUIFKKCHHE-UHFFFAOYSA-N 0.000 claims 1
- LMUPYCURTUTFEZ-ZEQRLZLVSA-N 4-methoxy-n-[(2s)-1-[4-[5-[4-[[(2s)-2-[(4-methoxyquinoline-2-carbonyl)amino]propanoyl]amino]phenyl]-1,3,4-oxadiazol-2-yl]anilino]-1-oxopropan-2-yl]quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N[C@@H](C)C(=O)NC3=CC=C(C=C3)C3=NN=C(O3)C3=CC=C(C=C3)NC(=O)[C@H](C)NC(=O)C=3C=C(C4=CC=CC=C4N=3)OC)=CC(OC)=C21 LMUPYCURTUTFEZ-ZEQRLZLVSA-N 0.000 claims 1
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-
2010
- 2010-12-21 US US12/974,069 patent/US8362020B2/en active Active
- 2010-12-22 EP EP10801065A patent/EP2519506A1/en not_active Withdrawn
- 2010-12-22 CN CN201080064935.6A patent/CN102791693B/zh not_active Expired - Fee Related
- 2010-12-22 JP JP2012547159A patent/JP5787900B2/ja not_active Expired - Fee Related
- 2010-12-22 WO PCT/US2010/061855 patent/WO2011082077A1/en not_active Ceased
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2012
- 2012-11-07 US US13/670,691 patent/US8735398B2/en active Active
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