JP2014500323A5 - - Google Patents
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- JP2014500323A5 JP2014500323A5 JP2013546270A JP2013546270A JP2014500323A5 JP 2014500323 A5 JP2014500323 A5 JP 2014500323A5 JP 2013546270 A JP2013546270 A JP 2013546270A JP 2013546270 A JP2013546270 A JP 2013546270A JP 2014500323 A5 JP2014500323 A5 JP 2014500323A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- carbonyl
- acid
- substituted
- chlorophenyl
- 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.)
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 47
- 229910052799 carbon Inorganic materials 0.000 claims 25
- 150000001721 carbon Chemical group 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000000623 heterocyclic group Chemical group 0.000 claims 21
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 21
- 125000005843 halogen group Chemical group 0.000 claims 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims 18
- 229910052757 nitrogen Inorganic materials 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 16
- -1 C 1 -C 3 alkyl Chemical group 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 12
- 239000002253 acid Substances 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 11
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 10
- 125000001153 fluoro group Chemical group F* 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 229910052717 sulfur Inorganic materials 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 4
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims 2
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- AHULTIIBEPSESW-XMMPIXPASA-N 5-[7-[[(1r)-6-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl]carbamoyl]-3-phenylquinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)N[C@H]3C4=CC=C(F)C=C4CCC3)=CC=C2N=C1C1=CC=CC=C1 AHULTIIBEPSESW-XMMPIXPASA-N 0.000 claims 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- PLEHSLVXSJBCKV-UHFFFAOYSA-N 1-methylspiro[2h-indole-3,4'-piperidine] Chemical compound C12=CC=CC=C2N(C)CC21CCNCC2 PLEHSLVXSJBCKV-UHFFFAOYSA-N 0.000 claims 1
- CKUIIYFYSJOMEB-UHFFFAOYSA-N 2-[2-[3-phenyl-7-(4-phenylpiperidine-1-carbonyl)quinoxalin-2-yl]ethyl]cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1CCC1=NC2=CC(C(=O)N3CCC(CC3)C=3C=CC=CC=3)=CC=C2N=C1C1=CC=CC=C1 CKUIIYFYSJOMEB-UHFFFAOYSA-N 0.000 claims 1
- ATCZSYWQJLLZQT-HXUWFJFHSA-N 2-[3-[2-[3-(4-chlorophenyl)-7-[[(1r)-1-(4-fluorophenyl)ethyl]carbamoyl]quinoxalin-2-yl]ethyl]phenyl]acetic acid Chemical compound N([C@H](C)C=1C=CC(F)=CC=1)C(=O)C(C=C1N=2)=CC=C1N=C(C=1C=CC(Cl)=CC=1)C=2CCC1=CC=CC(CC(O)=O)=C1 ATCZSYWQJLLZQT-HXUWFJFHSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- HBOHHMXJFJZJFP-UHFFFAOYSA-N 2-methyl-5-[7-(4-phenylpiperidine-1-carbonyl)-3-[4-(trifluoromethyl)phenyl]quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)C(C)CCCC1=NC2=CC(C(=O)N3CCC(CC3)C=3C=CC=CC=3)=CC=C2N=C1C1=CC=C(C(F)(F)F)C=C1 HBOHHMXJFJZJFP-UHFFFAOYSA-N 0.000 claims 1
- FCMHMWSISMADQK-HSZRJFAPSA-N 4-[[3-phenyl-7-[[(1r)-1,2,3,4-tetrahydronaphthalen-1-yl]carbamoyl]quinoxalin-2-yl]amino]butanoic acid Chemical compound OC(=O)CCCNC1=NC2=CC(C(=O)N[C@H]3C4=CC=CC=C4CCC3)=CC=C2N=C1C1=CC=CC=C1 FCMHMWSISMADQK-HSZRJFAPSA-N 0.000 claims 1
- YLGGKIXDLNCBDG-UHFFFAOYSA-N 4-[[7-[4-(4-fluorophenyl)piperazine-1-carbonyl]-3-phenylquinoxalin-2-yl]amino]butanoic acid Chemical compound OC(=O)CCCNC1=NC2=CC(C(=O)N3CCN(CC3)C=3C=CC(F)=CC=3)=CC=C2N=C1C1=CC=CC=C1 YLGGKIXDLNCBDG-UHFFFAOYSA-N 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- UXVXQIXXRFWEHY-UHFFFAOYSA-N 5-[3-(2,4-dichlorophenyl)-7-(4-phenylpiperidine-1-carbonyl)quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)N3CCC(CC3)C=3C=CC=CC=3)=CC=C2N=C1C1=CC=C(Cl)C=C1Cl UXVXQIXXRFWEHY-UHFFFAOYSA-N 0.000 claims 1
- GTYULXMAFRIULP-UHFFFAOYSA-N 5-[3-(2-chlorophenyl)-7-(4-phenylpiperidine-1-carbonyl)quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)N3CCC(CC3)C=3C=CC=CC=3)=CC=C2N=C1C1=CC=CC=C1Cl GTYULXMAFRIULP-UHFFFAOYSA-N 0.000 claims 1
- LYSLGIYLHAJKNV-UHFFFAOYSA-N 5-[3-(3-chlorophenyl)-7-(4-phenylpiperidine-1-carbonyl)quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)N3CCC(CC3)C=3C=CC=CC=3)=CC=C2N=C1C1=CC=CC(Cl)=C1 LYSLGIYLHAJKNV-UHFFFAOYSA-N 0.000 claims 1
- NJVVDPIZJKMBBV-UHFFFAOYSA-N 5-[3-(3-fluorophenyl)-7-(3-phenylpyrrolidine-1-carbonyl)quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)N3CC(CC3)C=3C=CC=CC=3)=CC=C2N=C1C1=CC=CC(F)=C1 NJVVDPIZJKMBBV-UHFFFAOYSA-N 0.000 claims 1
- ZCHFLTJXTZIDBK-UHFFFAOYSA-N 5-[3-(4-chlorophenyl)-7-(3-oxospiro[2,4-dihydroisoquinoline-1,4'-piperidine]-1'-carbonyl)quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)N3CCC4(CC3)C3=CC=CC=C3CC(=O)N4)=CC=C2N=C1C1=CC=C(Cl)C=C1 ZCHFLTJXTZIDBK-UHFFFAOYSA-N 0.000 claims 1
- WVYXGMXYFUDADF-UHFFFAOYSA-N 5-[3-(4-chlorophenyl)-7-(4-phenylpiperazine-1-carbonyl)quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)N3CCN(CC3)C=3C=CC=CC=3)=CC=C2N=C1C1=CC=C(Cl)C=C1 WVYXGMXYFUDADF-UHFFFAOYSA-N 0.000 claims 1
- NITJHYGVFOXRNS-UHFFFAOYSA-N 5-[3-(4-chlorophenyl)-7-(4-phenylpiperidine-1-carbonyl)quinoxalin-2-yl]-2-methylpentanoic acid Chemical compound OC(=O)C(C)CCCC1=NC2=CC(C(=O)N3CCC(CC3)C=3C=CC=CC=3)=CC=C2N=C1C1=CC=C(Cl)C=C1 NITJHYGVFOXRNS-UHFFFAOYSA-N 0.000 claims 1
- UGXDYFAJDDBFQB-UHFFFAOYSA-N 5-[3-(4-chlorophenyl)-7-(4-phenylpiperidine-1-carbonyl)quinoxalin-2-yl]-3-methylpentanoic acid Chemical compound OC(=O)CC(C)CCC1=NC2=CC(C(=O)N3CCC(CC3)C=3C=CC=CC=3)=CC=C2N=C1C1=CC=C(Cl)C=C1 UGXDYFAJDDBFQB-UHFFFAOYSA-N 0.000 claims 1
- SRUXDYWXCHAAGK-UHFFFAOYSA-N 5-[3-(4-chlorophenyl)-7-(4-phenylpiperidine-1-carbonyl)quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)N3CCC(CC3)C=3C=CC=CC=3)=CC=C2N=C1C1=CC=C(Cl)C=C1 SRUXDYWXCHAAGK-UHFFFAOYSA-N 0.000 claims 1
- ABUWKLSZDNQAPT-UHFFFAOYSA-N 5-[3-(4-chlorophenyl)-7-[(3-chlorophenyl)methylcarbamoyl]quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)NCC=3C=C(Cl)C=CC=3)=CC=C2N=C1C1=CC=C(Cl)C=C1 ABUWKLSZDNQAPT-UHFFFAOYSA-N 0.000 claims 1
- DKHCNCMNAWJEAR-DEOSSOPVSA-N 5-[3-(4-chlorophenyl)-7-[(3r)-3-phenylpiperidine-1-carbonyl]quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)N3C[C@H](CCC3)C=3C=CC=CC=3)=CC=C2N=C1C1=CC=C(Cl)C=C1 DKHCNCMNAWJEAR-DEOSSOPVSA-N 0.000 claims 1
- NGLZCDGNGNQGTC-UHFFFAOYSA-N 5-[3-(4-chlorophenyl)-7-[(4-chlorophenyl)methylcarbamoyl]quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)NCC=3C=CC(Cl)=CC=3)=CC=C2N=C1C1=CC=C(Cl)C=C1 NGLZCDGNGNQGTC-UHFFFAOYSA-N 0.000 claims 1
- JLBOYXNHRJDIOI-UHFFFAOYSA-N 5-[3-(4-chlorophenyl)-7-[(4-cyanophenyl)methylcarbamoyl]quinoxalin-2-yl]-2-methylpentanoic acid Chemical compound OC(=O)C(C)CCCC1=NC2=CC(C(=O)NCC=3C=CC(=CC=3)C#N)=CC=C2N=C1C1=CC=C(Cl)C=C1 JLBOYXNHRJDIOI-UHFFFAOYSA-N 0.000 claims 1
- NJMWDGMQZOCRLR-UHFFFAOYSA-N 5-[3-(4-chlorophenyl)-7-[(4-cyanophenyl)methylcarbamoyl]quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)NCC=3C=CC(=CC=3)C#N)=CC=C2N=C1C1=CC=C(Cl)C=C1 NJMWDGMQZOCRLR-UHFFFAOYSA-N 0.000 claims 1
- VPUHVGZKBQZBCQ-UHFFFAOYSA-N 5-[3-(4-chlorophenyl)-7-[(4-fluorophenyl)methylcarbamoyl]quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)NCC=3C=CC(F)=CC=3)=CC=C2N=C1C1=CC=C(Cl)C=C1 VPUHVGZKBQZBCQ-UHFFFAOYSA-N 0.000 claims 1
- OTGJKOCMFDWBSY-UHFFFAOYSA-N 5-[3-(4-chlorophenyl)-7-[(4-methylphenyl)methylcarbamoyl]quinoxalin-2-yl]pentanoic acid Chemical compound C1=CC(C)=CC=C1CNC(=O)C1=CC=C(N=C(C(CCCCC(O)=O)=N2)C=3C=CC(Cl)=CC=3)C2=C1 OTGJKOCMFDWBSY-UHFFFAOYSA-N 0.000 claims 1
- FJZRMJPPNHAQHW-UHFFFAOYSA-N 5-[3-(4-chlorophenyl)-7-[3-(4-chlorophenyl)azetidine-1-carbonyl]quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)N3CC(C3)C=3C=CC(Cl)=CC=3)=CC=C2N=C1C1=CC=C(Cl)C=C1 FJZRMJPPNHAQHW-UHFFFAOYSA-N 0.000 claims 1
- WTSCOWYNIMHQMR-UHFFFAOYSA-N 5-[3-(4-chlorophenyl)-7-[4-(2,6-dimethylphenyl)piperazine-1-carbonyl]quinoxalin-2-yl]pentanoic acid Chemical compound CC1=CC=CC(C)=C1N1CCN(C(=O)C=2C=C3N=C(CCCCC(O)=O)C(=NC3=CC=2)C=2C=CC(Cl)=CC=2)CC1 WTSCOWYNIMHQMR-UHFFFAOYSA-N 0.000 claims 1
- WSGSQWFAXNIQAN-MRXNPFEDSA-N 5-[3-(4-chlorophenyl)-7-[[(1r)-1-(3,5-difluorophenyl)ethyl]carbamoyl]quinoxalin-2-yl]pentanoic acid Chemical compound N([C@H](C)C=1C=C(F)C=C(F)C=1)C(=O)C(C=C1N=C2CCCCC(O)=O)=CC=C1N=C2C1=CC=C(Cl)C=C1 WSGSQWFAXNIQAN-MRXNPFEDSA-N 0.000 claims 1
- LUHSVHVYLKBSFI-QGZVFWFLSA-N 5-[3-(4-chlorophenyl)-7-[[(1r)-1-(4-fluorophenyl)ethyl]carbamoyl]quinoxalin-2-yl]pentanoic acid Chemical compound N([C@H](C)C=1C=CC(F)=CC=1)C(=O)C(C=C1N=C2CCCCC(O)=O)=CC=C1N=C2C1=CC=C(Cl)C=C1 LUHSVHVYLKBSFI-QGZVFWFLSA-N 0.000 claims 1
- OAZRQIRRMIRDQK-INIZCTEOSA-N 5-[3-(4-chlorophenyl)-7-[[(1s)-1-(3,4-difluorophenyl)ethyl]carbamoyl]quinoxalin-2-yl]pentanoic acid Chemical compound N([C@@H](C)C=1C=C(F)C(F)=CC=1)C(=O)C(C=C1N=C2CCCCC(O)=O)=CC=C1N=C2C1=CC=C(Cl)C=C1 OAZRQIRRMIRDQK-INIZCTEOSA-N 0.000 claims 1
- ZFJBYRNIBUAPIZ-ZVAWYAOSSA-N 5-[3-(4-chlorophenyl)-7-[[(1s)-1-(4-chlorophenyl)ethyl]carbamoyl]quinoxalin-2-yl]-3-methylpentanoic acid Chemical compound OC(=O)CC(C)CCC1=NC2=CC(C(=O)N[C@@H](C)C=3C=CC(Cl)=CC=3)=CC=C2N=C1C1=CC=C(Cl)C=C1 ZFJBYRNIBUAPIZ-ZVAWYAOSSA-N 0.000 claims 1
- OFQDLPFZBWUVFT-KRWDZBQOSA-N 5-[3-(4-chlorophenyl)-7-[[(1s)-1-(4-chlorophenyl)ethyl]carbamoyl]quinoxalin-2-yl]pentanoic acid Chemical compound N([C@@H](C)C=1C=CC(Cl)=CC=1)C(=O)C(C=C1N=C2CCCCC(O)=O)=CC=C1N=C2C1=CC=C(Cl)C=C1 OFQDLPFZBWUVFT-KRWDZBQOSA-N 0.000 claims 1
- YGLXTOGDGBRMCU-ZVAWYAOSSA-N 5-[3-(4-chlorophenyl)-7-[[(1s)-1-(4-fluorophenyl)ethyl]carbamoyl]quinoxalin-2-yl]-2-methylpentanoic acid Chemical compound OC(=O)C(C)CCCC1=NC2=CC(C(=O)N[C@@H](C)C=3C=CC(F)=CC=3)=CC=C2N=C1C1=CC=C(Cl)C=C1 YGLXTOGDGBRMCU-ZVAWYAOSSA-N 0.000 claims 1
- LUHSVHVYLKBSFI-KRWDZBQOSA-N 5-[3-(4-chlorophenyl)-7-[[(1s)-1-(4-fluorophenyl)ethyl]carbamoyl]quinoxalin-2-yl]pentanoic acid Chemical compound N([C@@H](C)C=1C=CC(F)=CC=1)C(=O)C(C=C1N=C2CCCCC(O)=O)=CC=C1N=C2C1=CC=C(Cl)C=C1 LUHSVHVYLKBSFI-KRWDZBQOSA-N 0.000 claims 1
- FSHWGGMDSFJDMP-SANMLTNESA-N 5-[3-(4-chlorophenyl)-7-[[(1s)-2,2,2-trifluoro-1-(4-fluorophenyl)ethyl]carbamoyl]quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)N[C@@H](C=3C=CC(F)=CC=3)C(F)(F)F)=CC=C2N=C1C1=CC=C(Cl)C=C1 FSHWGGMDSFJDMP-SANMLTNESA-N 0.000 claims 1
- VHDSRXYQUVZRQE-KKFPZRRJSA-N 5-[3-(4-chlorophenyl)-7-[[(1s)-2,2,2-trifluoro-1-phenylethyl]carbamoyl]quinoxalin-2-yl]-2-methylpentanoic acid Chemical compound OC(=O)C(C)CCCC1=NC2=CC(C(=O)N[C@@H](C=3C=CC=CC=3)C(F)(F)F)=CC=C2N=C1C1=CC=C(Cl)C=C1 VHDSRXYQUVZRQE-KKFPZRRJSA-N 0.000 claims 1
- UICRIQGBCJEJOV-LYTHVRBOSA-N 5-[3-(4-chlorophenyl)-7-[[(1s)-2,2,2-trifluoro-1-phenylethyl]carbamoyl]quinoxalin-2-yl]-3-methylpentanoic acid Chemical compound OC(=O)CC(C)CCC1=NC2=CC(C(=O)N[C@@H](C=3C=CC=CC=3)C(F)(F)F)=CC=C2N=C1C1=CC=C(Cl)C=C1 UICRIQGBCJEJOV-LYTHVRBOSA-N 0.000 claims 1
- PMRMAQMOQKTSPA-SANMLTNESA-N 5-[3-(4-chlorophenyl)-7-[[(1s)-2,2,2-trifluoro-1-phenylethyl]carbamoyl]quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)N[C@@H](C=3C=CC=CC=3)C(F)(F)F)=CC=C2N=C1C1=CC=C(Cl)C=C1 PMRMAQMOQKTSPA-SANMLTNESA-N 0.000 claims 1
- QHPMRURREYGFPL-QFIPXVFZSA-N 5-[3-(4-chlorophenyl)-7-[[(4s)-3,4-dihydro-2h-chromen-4-yl]carbamoyl]quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)N[C@@H]3C4=CC=CC=C4OCC3)=CC=C2N=C1C1=CC=C(Cl)C=C1 QHPMRURREYGFPL-QFIPXVFZSA-N 0.000 claims 1
- YFEDJXVZDTWTNQ-UHFFFAOYSA-N 5-[3-(4-cyanophenyl)-7-(4-phenylpiperidine-1-carbonyl)quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)N3CCC(CC3)C=3C=CC=CC=3)=CC=C2N=C1C1=CC=C(C#N)C=C1 YFEDJXVZDTWTNQ-UHFFFAOYSA-N 0.000 claims 1
- YXXSTFZHHVEZRL-UHFFFAOYSA-N 5-[3-(4-fluorophenyl)-7-(3-phenylpyrrolidine-1-carbonyl)quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)N3CC(CC3)C=3C=CC=CC=3)=CC=C2N=C1C1=CC=C(F)C=C1 YXXSTFZHHVEZRL-UHFFFAOYSA-N 0.000 claims 1
- XVMNNQVVFSVODZ-UHFFFAOYSA-N 5-[3-(4-fluorophenyl)-7-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carbonyl)quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)N3CCC4(CC3)C(NCN4C=3C=CC=CC=3)=O)=CC=C2N=C1C1=CC=C(F)C=C1 XVMNNQVVFSVODZ-UHFFFAOYSA-N 0.000 claims 1
- BIROENSSMJMMMJ-UHFFFAOYSA-N 5-[3-(4-fluorophenyl)-7-(4-phenyl-3,6-dihydro-2h-pyridine-1-carbonyl)quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)N3CC=C(CC3)C=3C=CC=CC=3)=CC=C2N=C1C1=CC=C(F)C=C1 BIROENSSMJMMMJ-UHFFFAOYSA-N 0.000 claims 1
- JQNFVAHCXSPKMC-UHFFFAOYSA-N 5-[3-(4-fluorophenyl)-7-(4-phenylpiperazine-1-carbonyl)quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)N3CCN(CC3)C=3C=CC=CC=3)=CC=C2N=C1C1=CC=C(F)C=C1 JQNFVAHCXSPKMC-UHFFFAOYSA-N 0.000 claims 1
- MALHGOATKFJPPJ-UHFFFAOYSA-N 5-[3-(4-fluorophenyl)-7-(4-phenylpiperidine-1-carbonyl)quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)N3CCC(CC3)C=3C=CC=CC=3)=CC=C2N=C1C1=CC=C(F)C=C1 MALHGOATKFJPPJ-UHFFFAOYSA-N 0.000 claims 1
- UUXJVLABONBKOF-UHFFFAOYSA-N 5-[3-(4-fluorophenyl)-7-[(4-fluorophenyl)methylcarbamoyl]quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)NCC=3C=CC(F)=CC=3)=CC=C2N=C1C1=CC=C(F)C=C1 UUXJVLABONBKOF-UHFFFAOYSA-N 0.000 claims 1
- NGVRTHJIKOSOBD-XMMPIXPASA-N 5-[3-(4-fluorophenyl)-7-[[(1r)-1,2,3,4-tetrahydronaphthalen-1-yl]carbamoyl]quinoxalin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCC1=NC2=CC(C(=O)N[C@H]3C4=CC=CC=C4CCC3)=CC=C2N=C1C1=CC=C(F)C=C1 NGVRTHJIKOSOBD-XMMPIXPASA-N 0.000 claims 1
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| EP2590944B1 (en) | 2010-07-05 | 2015-09-30 | Actelion Pharmaceuticals Ltd. | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin d2 receptor modulators |
| US8927559B2 (en) | 2010-10-11 | 2015-01-06 | Merck Sharp & Dohme Corp. | Quinazolinone-type compounds as CRTH2 antagonists |
| WO2012087872A1 (en) | 2010-12-23 | 2012-06-28 | Merck Sharp & Dohme Corp. | Quinolines and aza-quinolines as crth2 receptor modulators |
| CN103459382B (zh) * | 2011-03-02 | 2016-06-29 | 拜奥埃内杰尼克斯公司 | 用于抑制pask的杂环化合物 |
| EA025100B1 (ru) | 2011-06-17 | 2016-11-30 | Мерк Шарп И Доум Корп. | Циклоалкил-конденсированные тетрагидрохинолины в качестве модуляторов рецепторов crth |
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| MX361539B (es) | 2012-04-25 | 2018-12-10 | Takeda Pharmaceuticals Co | Compuesto heterociclico nitrogenado. |
| US9169270B2 (en) | 2012-07-05 | 2015-10-27 | Actelion Pharmaceuticals Ltd. | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin D2 receptor modulators |
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| WO2014121885A1 (en) | 2013-02-07 | 2014-08-14 | Merck Patent Gmbh | Substituted quinoxaline derivatives and their use as positive allosteric modulators of mglur4 |
| JP6280912B2 (ja) | 2013-03-14 | 2018-02-14 | 武田薬品工業株式会社 | 複素環化合物 |
| WO2015002231A1 (ja) | 2013-07-03 | 2015-01-08 | 武田薬品工業株式会社 | 複素環化合物 |
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| EP3026051A4 (en) | 2013-07-24 | 2017-03-08 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| EP3126005A4 (en) | 2014-03-31 | 2017-11-29 | The Trustees Of The University Of Pennsylvania | Novel antiviral compounds and methods using same |
| TW201625578A (zh) | 2014-04-18 | 2016-07-16 | 千禧製藥公司 | 喹啉化合物及其用途 |
| US10323018B2 (en) | 2015-01-20 | 2019-06-18 | Millennium Pharmaceuticals, Inc. | Quinazoline and quinoline compounds and uses thereof |
| KR20200022027A (ko) * | 2017-06-30 | 2020-03-02 | 리부 세라퓨틱스 에스.에이. | 아데노신 A2A 수용체의 이미다조[1,2,a]피라진 조절물질 |
| EP3644998B1 (en) | 2017-06-30 | 2024-04-10 | Quixgen, Inc. | Novel spirolactone compounds |
| EP3643711A1 (en) * | 2018-10-24 | 2020-04-29 | Bayer Animal Health GmbH | New anthelmintic compounds |
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Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| WO1995015973A1 (en) | 1993-12-06 | 1995-06-15 | Cytel Corporation | Cs-1 peptidomimetics, compositions and methods of using the same |
| US5510332A (en) | 1994-07-07 | 1996-04-23 | Texas Biotechnology Corporation | Process to inhibit binding of the integrin α4 62 1 to VCAM-1 or fibronectin and linear peptides therefor |
| CA2193508A1 (en) | 1994-07-11 | 1996-01-25 | Eugene D. Thorsett | Inhibitors of leukocyte adhesion |
| US5811391A (en) | 1994-08-25 | 1998-09-22 | Cytel Corporation | Cyclic CS-1 peptidomimetics, compositions and methods of using same |
| GB9524630D0 (en) | 1994-12-24 | 1996-01-31 | Zeneca Ltd | Chemical compounds |
| US6306840B1 (en) | 1995-01-23 | 2001-10-23 | Biogen, Inc. | Cell adhesion inhibitors |
| WO1996031206A2 (en) | 1995-04-07 | 1996-10-10 | Warner-Lambert Company | Flavones and coumarins as agents for the treatment of atherosclerosis |
| WO1996040781A1 (en) | 1995-06-07 | 1996-12-19 | Tanabe Seiyaku Co., Ltd. | CYCLIC PEPTIDE INHIBITORS OF β1 AND β2 INTEGRIN-MEDIATED ADHESION |
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| US6248713B1 (en) | 1995-07-11 | 2001-06-19 | Biogen, Inc. | Cell adhesion inhibitors |
| DE10013318A1 (de) * | 2000-03-17 | 2001-09-20 | Merck Patent Gmbh | Formulierung enthaltend Chinoxalinderivate |
| GB0023918D0 (en) | 2000-09-29 | 2000-11-15 | King S College London | Antiparasitic compounds |
| IL155089A0 (en) | 2000-10-12 | 2003-10-31 | Merck & Co Inc | Aza and polyaza-naphthalenyl carboxamides useful as hiv integrase inhibitors |
| BR0312802A (pt) | 2002-07-19 | 2005-04-19 | Michael E Garst | Pró-drogas de inibidores de bombas de próton |
| MXPA05003660A (es) * | 2002-10-21 | 2005-06-08 | Warner Lambert Co | Derivados de quinolina como antagonistas de crth2. |
| NZ544173A (en) | 2003-07-15 | 2009-04-30 | Alevium Pharmaceuticals Inc | Process for preparing isomerically pure prodrugs of benzimidazole derivative proton pump inhibitors |
| GB0324763D0 (en) * | 2003-10-23 | 2003-11-26 | Oxagen Ltd | Use of compounds in therapy |
| MY144903A (en) * | 2004-06-17 | 2011-11-30 | Novartis Ag | Pyrrolopyridine derivatives and their use as crth2 antagonists |
| US7977354B2 (en) | 2005-04-01 | 2011-07-12 | Insa Rouen | Heterocyclic compounds, their preparation and their use as medicaments, in particular as anti-alzheimer agents |
| EP1915372B1 (en) | 2005-08-12 | 2013-11-20 | Merck Canada Inc. | Indole derivatives as crth2 receptor antagonists |
| JP2009520700A (ja) | 2005-12-21 | 2009-05-28 | ペインセプター ファーマ コーポレーション | 依存性イオンチャネルを調節するための組成物および方法 |
| TW200808793A (en) | 2006-03-07 | 2008-02-16 | Smithkline Beecham Corp | Prolyl hydroxylase inhibitors |
| WO2007138112A2 (en) | 2006-06-01 | 2007-12-06 | Devgen N.V. | Compounds that interact with ion channels, in particular with ion channels from the kv family |
| MX2009010376A (es) * | 2007-03-29 | 2010-01-20 | Argenta Oral Therapeutics Ltd | Derivados de quinolina como ligandos del receptor crth2. |
| GB0722203D0 (en) * | 2007-11-13 | 2007-12-19 | Oxagen Ltd | Use of CRTH2 antagonist compounds |
| WO2010031182A1 (en) | 2008-09-22 | 2010-03-25 | Merck Frosst Canada Ltd. | Indole derivatives as crth2 receptor antagonists |
| JP2012502927A (ja) | 2008-09-22 | 2012-02-02 | メルク カナダ インコーポレイテッド | Ｃｒｔｈ２受容体拮抗薬としてのインドール誘導体 |
| CA2736571A1 (en) | 2008-09-22 | 2010-03-25 | Merck Frosst Canada Ltd. | Azaindole derivatives as crth2 receptor antagonists |
| JPWO2010074244A1 (ja) * | 2008-12-25 | 2012-06-21 | 大正製薬株式会社 | イソキノリン誘導体 |
| KR101276530B1 (ko) | 2009-02-24 | 2013-06-18 | 머크 캐나다 인크. | Ｃｒｔｈ２ 수용체 길항제로서의 인돌 유도체 |
| CA2772714C (en) | 2009-09-03 | 2017-09-26 | Bioenergenix | Heterocyclic compounds for the inhibition of pask |
| US8927559B2 (en) | 2010-10-11 | 2015-01-06 | Merck Sharp & Dohme Corp. | Quinazolinone-type compounds as CRTH2 antagonists |
| WO2012087872A1 (en) | 2010-12-23 | 2012-06-28 | Merck Sharp & Dohme Corp. | Quinolines and aza-quinolines as crth2 receptor modulators |
| EA025100B1 (ru) | 2011-06-17 | 2016-11-30 | Мерк Шарп И Доум Корп. | Циклоалкил-конденсированные тетрагидрохинолины в качестве модуляторов рецепторов crth |
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- 2011-12-19 JP JP2013546270A patent/JP5952829B2/ja not_active Expired - Fee Related
- 2011-12-19 MX MX2013007295A patent/MX2013007295A/es not_active Application Discontinuation
- 2011-12-19 ES ES11851281.3T patent/ES2635030T3/es active Active
- 2011-12-19 WO PCT/US2011/065716 patent/WO2012087861A1/en not_active Ceased
- 2011-12-19 RU RU2013134334/04A patent/RU2589709C2/ru not_active IP Right Cessation
- 2011-12-19 CN CN201180062255.5A patent/CN103702985B/zh not_active Expired - Fee Related
- 2011-12-19 US US13/996,361 patent/US9469615B2/en active Active
- 2011-12-19 BR BR112013015397A patent/BR112013015397A2/pt not_active Application Discontinuation
- 2011-12-21 TW TW100147844A patent/TW201307302A/zh unknown
- 2011-12-22 AR ARP110104895A patent/AR084573A1/es unknown
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