JP2016528274A5 - - Google Patents
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- Publication number
- JP2016528274A5 JP2016528274A5 JP2016535530A JP2016535530A JP2016528274A5 JP 2016528274 A5 JP2016528274 A5 JP 2016528274A5 JP 2016535530 A JP2016535530 A JP 2016535530A JP 2016535530 A JP2016535530 A JP 2016535530A JP 2016528274 A5 JP2016528274 A5 JP 2016528274A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- benzoic acid
- benzamido
- fluorophenoxy
- methoxyphenoxy
- 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
Links
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- -1 nitro, carboxyl Chemical group 0.000 claims description 30
- 239000005711 Benzoic acid Substances 0.000 claims description 28
- 235000010233 benzoic acid Nutrition 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 150000003456 sulfonamides Chemical class 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- FUQGEWZJMJSFMF-ALOJWSFFSA-N COc1ccccc1O[C@H]1CC[C@@H](CC1)C(=O)N(Cc1ccccc1)Cc1ccc(cc1)C(O)=O Chemical compound COc1ccccc1O[C@H]1CC[C@@H](CC1)C(=O)N(Cc1ccccc1)Cc1ccc(cc1)C(O)=O FUQGEWZJMJSFMF-ALOJWSFFSA-N 0.000 claims description 3
- WPZAXTRVIVQZCI-UHFFFAOYSA-N COc1ccccc1Oc1ccc(cc1)C(=O)N(CCCc1cccc(F)c1)Cc1ccc(cc1)C(O)=O Chemical compound COc1ccccc1Oc1ccc(cc1)C(=O)N(CCCc1cccc(F)c1)Cc1ccc(cc1)C(O)=O WPZAXTRVIVQZCI-UHFFFAOYSA-N 0.000 claims description 3
- XTKOCFGCADABCN-UHFFFAOYSA-N Cc1cccc(C)c1Oc1ccc(cc1)C(=O)N(CCc1ccccc1)Cc1ccc(cc1)C(O)=O Chemical compound Cc1cccc(C)c1Oc1ccc(cc1)C(=O)N(CCc1ccccc1)Cc1ccc(cc1)C(O)=O XTKOCFGCADABCN-UHFFFAOYSA-N 0.000 claims description 3
- ZZDYCPYBHLLDPA-UHFFFAOYSA-N Cc1ccccc1Oc1ccc(cc1)C(=O)N(Cc1ccc(cc1)C(O)=O)CC(F)(F)F Chemical compound Cc1ccccc1Oc1ccc(cc1)C(=O)N(Cc1ccc(cc1)C(O)=O)CC(F)(F)F ZZDYCPYBHLLDPA-UHFFFAOYSA-N 0.000 claims description 3
- SQFNSQHVILJRSM-UHFFFAOYSA-N OC(=O)c1ccc(CN(CC2CCC2)C(=O)c2ccc(OCc3ccccc3F)cc2)cc1 Chemical compound OC(=O)c1ccc(CN(CC2CCC2)C(=O)c2ccc(OCc3ccccc3F)cc2)cc1 SQFNSQHVILJRSM-UHFFFAOYSA-N 0.000 claims description 3
- GUCWMYPGSTXNQO-UHFFFAOYSA-N OC(=O)c1ccc(CN(CCC2CC2)C(=O)c2ccc(Oc3c(F)cccc3F)cc2)cc1 Chemical compound OC(=O)c1ccc(CN(CCC2CC2)C(=O)c2ccc(Oc3c(F)cccc3F)cc2)cc1 GUCWMYPGSTXNQO-UHFFFAOYSA-N 0.000 claims description 3
- WRWYGOVGIGCDLE-UHFFFAOYSA-N [O]c1ccccc1F Chemical group [O]c1ccccc1F WRWYGOVGIGCDLE-UHFFFAOYSA-N 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 2
- LEZVXIZCJXKBJY-UHFFFAOYSA-N 4-[[cyclopropylmethyl-[4-(2-fluorophenoxy)benzoyl]amino]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN(C(=O)C=1C=CC(OC=2C(=CC=CC=2)F)=CC=1)CC1CC1 LEZVXIZCJXKBJY-UHFFFAOYSA-N 0.000 claims description 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
- 125000000172 C5-C10 aryl group Chemical group 0.000 claims description 2
- XWQJXYFTQBSZFA-UHFFFAOYSA-N CC(C)CCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2c(C)cccc2C)cc1 Chemical compound CC(C)CCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2c(C)cccc2C)cc1 XWQJXYFTQBSZFA-UHFFFAOYSA-N 0.000 claims description 2
- XGFDCDKWZWQHSI-UHFFFAOYSA-N CC(C)CCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2F)cc1 Chemical compound CC(C)CCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2F)cc1 XGFDCDKWZWQHSI-UHFFFAOYSA-N 0.000 claims description 2
- CMQWTHVXHRXUNC-UHFFFAOYSA-N CC(C)CN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2F)cc1 Chemical compound CC(C)CN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2F)cc1 CMQWTHVXHRXUNC-UHFFFAOYSA-N 0.000 claims description 2
- ADACZCWUHYGVAD-UHFFFAOYSA-N CC(F)(F)CN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2F)cc1 Chemical compound CC(F)(F)CN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2F)cc1 ADACZCWUHYGVAD-UHFFFAOYSA-N 0.000 claims description 2
- SVNWCVFZMPJBLW-UHFFFAOYSA-N CCCCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2F)cc1 Chemical compound CCCCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2F)cc1 SVNWCVFZMPJBLW-UHFFFAOYSA-N 0.000 claims description 2
- KFQFCPMNEIOGPI-UHFFFAOYSA-N CCCCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2OC)cc1 Chemical compound CCCCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2OC)cc1 KFQFCPMNEIOGPI-UHFFFAOYSA-N 0.000 claims description 2
- JYKXYQKUPXZXOC-UHFFFAOYSA-N CCCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2cc(F)ccc2OC)cc1 Chemical compound CCCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2cc(F)ccc2OC)cc1 JYKXYQKUPXZXOC-UHFFFAOYSA-N 0.000 claims description 2
- LJTQGSYFZPTOOH-UHFFFAOYSA-N CCCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccc(F)cc2OC)cc1 Chemical compound CCCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccc(F)cc2OC)cc1 LJTQGSYFZPTOOH-UHFFFAOYSA-N 0.000 claims description 2
- SOSAKGSLKXKLFU-UHFFFAOYSA-N CCCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2F)cc1 Chemical compound CCCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2F)cc1 SOSAKGSLKXKLFU-UHFFFAOYSA-N 0.000 claims description 2
- HDFMOQYPAALHKY-UHFFFAOYSA-N CCCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2OC)cc1 Chemical compound CCCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2OC)cc1 HDFMOQYPAALHKY-UHFFFAOYSA-N 0.000 claims description 2
- WBAUSFZQQFMBCS-UHFFFAOYSA-N CCCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ncc(Oc2ccccc2OC)cn1 Chemical compound CCCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ncc(Oc2ccccc2OC)cn1 WBAUSFZQQFMBCS-UHFFFAOYSA-N 0.000 claims description 2
- FPBSEOINXWDZPK-UHFFFAOYSA-N CCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2C)cc1 Chemical compound CCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2C)cc1 FPBSEOINXWDZPK-UHFFFAOYSA-N 0.000 claims description 2
- BIVGLZVHXLZIGP-UHFFFAOYSA-N CCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2Cl)cc1 Chemical compound CCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2Cl)cc1 BIVGLZVHXLZIGP-UHFFFAOYSA-N 0.000 claims description 2
- SFLFAQAYQIAVDW-UHFFFAOYSA-N CCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2F)cc1 Chemical compound CCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2F)cc1 SFLFAQAYQIAVDW-UHFFFAOYSA-N 0.000 claims description 2
- LJVDDAKSLFFVPC-UHFFFAOYSA-N CCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2OC)cc1 Chemical compound CCN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2OC)cc1 LJVDDAKSLFFVPC-UHFFFAOYSA-N 0.000 claims description 2
- ONGMIZHEZHGEOT-UHFFFAOYSA-N CCOc1ccccc1Oc1ccc(cc1)C(=O)N(CC1CC1)Cc1ccc(cc1)C(O)=O Chemical compound CCOc1ccccc1Oc1ccc(cc1)C(=O)N(CC1CC1)Cc1ccc(cc1)C(O)=O ONGMIZHEZHGEOT-UHFFFAOYSA-N 0.000 claims description 2
- MEBSTCAWUQVIOV-UHFFFAOYSA-N COC1CC(CN(Cc2ccc(cc2)C(O)=O)C(=O)c2ccc(Oc3ccccc3F)cc2)C1 Chemical compound COC1CC(CN(Cc2ccc(cc2)C(O)=O)C(=O)c2ccc(Oc3ccccc3F)cc2)C1 MEBSTCAWUQVIOV-UHFFFAOYSA-N 0.000 claims description 2
- DPUNUQALECIJDK-UHFFFAOYSA-N COc1c(F)cccc1Oc1ccc(cc1)C(=O)N(CC1CC1)Cc1ccc(cc1)C(O)=O Chemical compound COc1c(F)cccc1Oc1ccc(cc1)C(=O)N(CC1CC1)Cc1ccc(cc1)C(O)=O DPUNUQALECIJDK-UHFFFAOYSA-N 0.000 claims description 2
- RZBDSWRRWUATTL-UHFFFAOYSA-N COc1cc(F)ccc1Oc1ccc(cc1)C(=O)N(CC1CC1)Cc1ccc(cc1)C(O)=O Chemical compound COc1cc(F)ccc1Oc1ccc(cc1)C(=O)N(CC1CC1)Cc1ccc(cc1)C(O)=O RZBDSWRRWUATTL-UHFFFAOYSA-N 0.000 claims description 2
- JAYQKBXYZDGMIP-UHFFFAOYSA-N COc1ccc(CN(Cc2ccc(cc2)C(O)=O)C(=O)c2ccc(Oc3ccccc3F)cc2)cc1 Chemical compound COc1ccc(CN(Cc2ccc(cc2)C(O)=O)C(=O)c2ccc(Oc3ccccc3F)cc2)cc1 JAYQKBXYZDGMIP-UHFFFAOYSA-N 0.000 claims description 2
- GGHASMDNUJBHLO-UHFFFAOYSA-N COc1ccc(F)cc1Oc1ccc(cc1)C(=O)N(CC1CC1)Cc1ccc(cc1)C(O)=O Chemical compound COc1ccc(F)cc1Oc1ccc(cc1)C(=O)N(CC1CC1)Cc1ccc(cc1)C(O)=O GGHASMDNUJBHLO-UHFFFAOYSA-N 0.000 claims description 2
- OUZLELZJXQVDPH-UHFFFAOYSA-N COc1ccc(Oc2ccc(cc2)C(=O)N(CCc2ccccc2)Cc2ccc(cc2)C(O)=O)cc1 Chemical compound COc1ccc(Oc2ccc(cc2)C(=O)N(CCc2ccccc2)Cc2ccc(cc2)C(O)=O)cc1 OUZLELZJXQVDPH-UHFFFAOYSA-N 0.000 claims description 2
- UIJGNVZGTKKTFL-UHFFFAOYSA-N COc1cccc(CN(Cc2ccc(C(O)=O)c(F)c2)C(=O)c2ccc(Oc3ccccc3F)cc2)c1 Chemical compound COc1cccc(CN(Cc2ccc(C(O)=O)c(F)c2)C(=O)c2ccc(Oc3ccccc3F)cc2)c1 UIJGNVZGTKKTFL-UHFFFAOYSA-N 0.000 claims description 2
- YWQLQJKICKYUSN-UHFFFAOYSA-N COc1cccc(F)c1Oc1ccc(cc1)C(=O)N(CC1CC1)Cc1ccc(cc1)C(O)=O Chemical compound COc1cccc(F)c1Oc1ccc(cc1)C(=O)N(CC1CC1)Cc1ccc(cc1)C(O)=O YWQLQJKICKYUSN-UHFFFAOYSA-N 0.000 claims description 2
- MIVMJXVFYIKSJK-UHFFFAOYSA-N COc1cccc(Oc2ccc(cc2)C(=O)N(CCc2ccccc2)Cc2ccc(cc2)C(O)=O)c1 Chemical compound COc1cccc(Oc2ccc(cc2)C(=O)N(CCc2ccccc2)Cc2ccc(cc2)C(O)=O)c1 MIVMJXVFYIKSJK-UHFFFAOYSA-N 0.000 claims description 2
- UBQWZKKHKXFYKG-HNKWHGCMSA-N COc1ccccc1O[C@H]1CC[C@@H](CC1)C(=O)N(CCCc1cccc(F)c1)Cc1ccc(cc1)C(O)=O Chemical compound COc1ccccc1O[C@H]1CC[C@@H](CC1)C(=O)N(CCCc1cccc(F)c1)Cc1ccc(cc1)C(O)=O UBQWZKKHKXFYKG-HNKWHGCMSA-N 0.000 claims description 2
- KBJKDHCJCODDDD-UHFFFAOYSA-N COc1ccccc1Oc1ccc(C(=O)N(CC2CC2)Cc2ccc(cc2)C(O)=O)c(F)c1 Chemical compound COc1ccccc1Oc1ccc(C(=O)N(CC2CC2)Cc2ccc(cc2)C(O)=O)c(F)c1 KBJKDHCJCODDDD-UHFFFAOYSA-N 0.000 claims description 2
- OSXBWRMTMQOKLS-UHFFFAOYSA-N COc1ccccc1Oc1ccc(cc1)C(=O)N(CC(C)C)Cc1ccc(cc1)C(O)=O Chemical compound COc1ccccc1Oc1ccc(cc1)C(=O)N(CC(C)C)Cc1ccc(cc1)C(O)=O OSXBWRMTMQOKLS-UHFFFAOYSA-N 0.000 claims description 2
- YOVTYVMJDJNYKX-UHFFFAOYSA-N COc1ccccc1Oc1ccc(cc1)C(=O)N(CC(F)F)Cc1ccc(cc1)C(O)=O Chemical compound COc1ccccc1Oc1ccc(cc1)C(=O)N(CC(F)F)Cc1ccc(cc1)C(O)=O YOVTYVMJDJNYKX-UHFFFAOYSA-N 0.000 claims description 2
- UCZBTVNWIVAWQV-UHFFFAOYSA-N COc1ccccc1Oc1ccc(cc1)C(=O)N(CC1CC1)Cc1ccc(cc1)C(O)=O Chemical compound COc1ccccc1Oc1ccc(cc1)C(=O)N(CC1CC1)Cc1ccc(cc1)C(O)=O UCZBTVNWIVAWQV-UHFFFAOYSA-N 0.000 claims description 2
- NJJLCPDOBBYPTD-UHFFFAOYSA-N COc1ccccc1Oc1ccc(cc1)C(=O)N(CCC(F)(F)F)Cc1ccc(cc1)C(O)=O Chemical compound COc1ccccc1Oc1ccc(cc1)C(=O)N(CCC(F)(F)F)Cc1ccc(cc1)C(O)=O NJJLCPDOBBYPTD-UHFFFAOYSA-N 0.000 claims description 2
- SVXWWGNELSAEBU-UHFFFAOYSA-N COc1ccccc1Oc1ccc(cc1)C(=O)N(CCCc1ccccc1)Cc1ccc(cc1)C(O)=O Chemical compound COc1ccccc1Oc1ccc(cc1)C(=O)N(CCCc1ccccc1)Cc1ccc(cc1)C(O)=O SVXWWGNELSAEBU-UHFFFAOYSA-N 0.000 claims description 2
- DCOUVLUIDXWAHJ-UHFFFAOYSA-N COc1ccccc1Oc1ccc(cc1)C(=O)N(Cc1ccc(cc1)C(O)=O)CC(F)(F)F Chemical compound COc1ccccc1Oc1ccc(cc1)C(=O)N(Cc1ccc(cc1)C(O)=O)CC(F)(F)F DCOUVLUIDXWAHJ-UHFFFAOYSA-N 0.000 claims description 2
- AXNASFMPKJGIGO-UHFFFAOYSA-N COc1ccccc1Oc1ccc(nc1)C(=O)N(CC1CC1)Cc1ccc(cc1)C(O)=O Chemical compound COc1ccccc1Oc1ccc(nc1)C(=O)N(CC1CC1)Cc1ccc(cc1)C(O)=O AXNASFMPKJGIGO-UHFFFAOYSA-N 0.000 claims description 2
- SGNXTFIPFVFVIJ-UHFFFAOYSA-N COc1ccccc1Oc1cnc(nc1)C(=O)N(CC1CC1)Cc1ccc(cc1)C(O)=O Chemical compound COc1ccccc1Oc1cnc(nc1)C(=O)N(CC1CC1)Cc1ccc(cc1)C(O)=O SGNXTFIPFVFVIJ-UHFFFAOYSA-N 0.000 claims description 2
- AFZOCQFROPJVCM-UHFFFAOYSA-N Cc1cccc(C)c1Oc1ccc(cc1)C(=O)N(Cc1ccccc1)Cc1ccc(cc1)C(O)=O Chemical compound Cc1cccc(C)c1Oc1ccc(cc1)C(=O)N(Cc1ccccc1)Cc1ccc(cc1)C(O)=O AFZOCQFROPJVCM-UHFFFAOYSA-N 0.000 claims description 2
- ONHLWLKFAFELOK-UHFFFAOYSA-N Cc1cccc(F)c1Oc1ccc(cc1)C(=O)N(CC1CC1)Cc1ccc(cc1)C(O)=O Chemical compound Cc1cccc(F)c1Oc1ccc(cc1)C(=O)N(CC1CC1)Cc1ccc(cc1)C(O)=O ONHLWLKFAFELOK-UHFFFAOYSA-N 0.000 claims description 2
- ZLXAJSGLSQMZJQ-UHFFFAOYSA-N Cc1cccc(F)c1Oc1ccc(cc1)C(=O)N(CC1CCC1)Cc1ccc(cc1)C(O)=O Chemical compound Cc1cccc(F)c1Oc1ccc(cc1)C(=O)N(CC1CCC1)Cc1ccc(cc1)C(O)=O ZLXAJSGLSQMZJQ-UHFFFAOYSA-N 0.000 claims description 2
- 241000255925 Diptera Species 0.000 claims description 2
- NUMUOXFQLCJLCA-UHFFFAOYSA-N OC(=O)c1ccc(CN(CC(F)(F)F)C(=O)c2ccc(Oc3ccccc3Cl)cc2)cc1 Chemical compound OC(=O)c1ccc(CN(CC(F)(F)F)C(=O)c2ccc(Oc3ccccc3Cl)cc2)cc1 NUMUOXFQLCJLCA-UHFFFAOYSA-N 0.000 claims description 2
- IEJGGFJTLXGJPD-UHFFFAOYSA-N OC(=O)c1ccc(CN(CC(F)(F)F)C(=O)c2ccc(Oc3ccccc3F)cc2)cc1 Chemical compound OC(=O)c1ccc(CN(CC(F)(F)F)C(=O)c2ccc(Oc3ccccc3F)cc2)cc1 IEJGGFJTLXGJPD-UHFFFAOYSA-N 0.000 claims description 2
- NSVGYWDUGKCWRF-UHFFFAOYSA-N OC(=O)c1ccc(CN(CC(F)F)C(=O)c2ccc(Oc3ccccc3Cl)cc2)cc1 Chemical compound OC(=O)c1ccc(CN(CC(F)F)C(=O)c2ccc(Oc3ccccc3Cl)cc2)cc1 NSVGYWDUGKCWRF-UHFFFAOYSA-N 0.000 claims description 2
- KARVIVULTZYCNP-UHFFFAOYSA-N OC(=O)c1ccc(CN(CC(F)F)C(=O)c2ccc(Oc3ccccc3F)cc2)cc1 Chemical compound OC(=O)c1ccc(CN(CC(F)F)C(=O)c2ccc(Oc3ccccc3F)cc2)cc1 KARVIVULTZYCNP-UHFFFAOYSA-N 0.000 claims description 2
- HNCSBMWLHBTZMT-UHFFFAOYSA-N OC(=O)c1ccc(CN(CC2CC2)C(=O)c2ccc(Oc3c(F)cccc3Cl)cc2)cc1 Chemical compound OC(=O)c1ccc(CN(CC2CC2)C(=O)c2ccc(Oc3c(F)cccc3Cl)cc2)cc1 HNCSBMWLHBTZMT-UHFFFAOYSA-N 0.000 claims description 2
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- IGYITFLQCJEIPG-UHFFFAOYSA-N OC(=O)c1ccc(CN(CC2CC2)C(=O)c2ccc(Oc3ccccc3F)cn2)cc1 Chemical compound OC(=O)c1ccc(CN(CC2CC2)C(=O)c2ccc(Oc3ccccc3F)cn2)cc1 IGYITFLQCJEIPG-UHFFFAOYSA-N 0.000 claims description 2
- TXROCRKOYMGIGD-UHFFFAOYSA-N OC(=O)c1ccc(CN(CC2CC2)C(=O)c2ncc(Oc3ccccc3F)cn2)cc1 Chemical compound OC(=O)c1ccc(CN(CC2CC2)C(=O)c2ncc(Oc3ccccc3F)cn2)cc1 TXROCRKOYMGIGD-UHFFFAOYSA-N 0.000 claims description 2
- JVVMHUKOPHTRQV-UHFFFAOYSA-N OC(=O)c1ccc(CN(CC2CCC2)C(=O)c2ccc(Oc3ccccc3F)cc2)cc1 Chemical compound OC(=O)c1ccc(CN(CC2CCC2)C(=O)c2ccc(Oc3ccccc3F)cc2)cc1 JVVMHUKOPHTRQV-UHFFFAOYSA-N 0.000 claims description 2
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- QUAWJVQPHQSFAD-UHFFFAOYSA-N OC(=O)c1ccc(CN(Cc2ccccc2)C(=O)c2ccc(Oc3c(F)cccc3Cl)cc2)cc1 Chemical compound OC(=O)c1ccc(CN(Cc2ccccc2)C(=O)c2ccc(Oc3c(F)cccc3Cl)cc2)cc1 QUAWJVQPHQSFAD-UHFFFAOYSA-N 0.000 claims description 2
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- WSECLOSWBXLDEI-UHFFFAOYSA-N OC(=O)c1ccc(CN(Cc2ccccc2)C(=O)c2ccc(Oc3ccccc3C#N)cc2)cc1 Chemical compound OC(=O)c1ccc(CN(Cc2ccccc2)C(=O)c2ccc(Oc3ccccc3C#N)cc2)cc1 WSECLOSWBXLDEI-UHFFFAOYSA-N 0.000 claims description 2
- PWSIYWWRGAIYIF-UHFFFAOYSA-N OC(=O)c1ccc(CN(Cc2ccccc2F)C(=O)c2ccc(Oc3ccccc3F)cc2)cc1 Chemical compound OC(=O)c1ccc(CN(Cc2ccccc2F)C(=O)c2ccc(Oc3ccccc3F)cc2)cc1 PWSIYWWRGAIYIF-UHFFFAOYSA-N 0.000 claims description 2
- HWJQFBVAJFHIFS-RUZDIDTESA-N O[C@@H](CN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2F)cc1)Cc1ccccc1 Chemical compound O[C@@H](CN(Cc1ccc(cc1)C(O)=O)C(=O)c1ccc(Oc2ccccc2F)cc1)Cc1ccccc1 HWJQFBVAJFHIFS-RUZDIDTESA-N 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
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- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- 102000016397 Methyltransferase Human genes 0.000 claims 1
- 108060004795 Methyltransferase Proteins 0.000 claims 1
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- ZKTDXQOVMQAYEG-UHFFFAOYSA-N Cc1ccccc1Oc1ccc(cc1)C(=O)N(CC1CC1)Cc1ccc(cc1)C(O)=O Chemical compound Cc1ccccc1Oc1ccc(cc1)C(=O)N(CC1CC1)Cc1ccc(cc1)C(O)=O ZKTDXQOVMQAYEG-UHFFFAOYSA-N 0.000 description 1
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
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| GBGB1314926.5A GB201314926D0 (en) | 2013-08-20 | 2013-08-20 | Novel Compounds |
| GB1314926.5 | 2013-08-20 | ||
| PCT/GB2014/052558 WO2015025164A1 (en) | 2013-08-20 | 2014-08-20 | Amide derivatives as lysophosphatidic acid receptor antagonists |
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| JP2016528274A JP2016528274A (ja) | 2016-09-15 |
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| JP6422974B2 JP6422974B2 (ja) | 2018-11-14 |
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| GB201314926D0 (en) * | 2013-08-20 | 2013-10-02 | Takeda Pharmaceutical | Novel Compounds |
| EP3870292A4 (en) | 2018-10-26 | 2022-11-09 | The Research Foundation for The State University of New York | COMBINATION OF SEROTONIN-SPECIFIC RESUPPUT INHIBITOR AND SEROTONIN 1A RECEPTOR PARTIAL AGONIST TO REDUCE L-DOPA-INDUCED DYSKINESIA |
| AU2020323429B2 (en) | 2019-07-30 | 2025-06-26 | Taisho Pharmaceutical Co., Ltd. | Urea compound for antagonizing LPA1 receptor |
| EP4058144A1 (en) | 2019-11-15 | 2022-09-21 | Gilead Sciences, Inc. | Triazole carbamate pyridyl sulfonamides as lpa receptor antagonists and uses thereof |
| CA3185689A1 (en) | 2020-06-03 | 2021-12-09 | Gilead Sciences, Inc. | Lpa receptor antagonists and uses thereof |
| TWI838626B (zh) | 2020-06-03 | 2024-04-11 | 美商基利科學股份有限公司 | Lpa受體拮抗劑及其用途 |
| EP4337641A1 (en) | 2021-05-11 | 2024-03-20 | Gilead Sciences, Inc. | Lpa receptor antagonists and uses thereof |
| EP4337654A1 (en) | 2021-05-13 | 2024-03-20 | Gilead Sciences, Inc. | Lpa receptor antagonists and uses thereof |
| EP4444707A1 (en) | 2021-12-08 | 2024-10-16 | Gilead Sciences, Inc. | Lpa receptor antagonists and uses thereof |
| WO2024252334A1 (en) * | 2023-06-06 | 2024-12-12 | Gpcr Therapeutics, Inc. | Gpcr inhibitors and uses thereof |
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| FR2707641B1 (fr) * | 1993-07-16 | 1995-08-25 | Fournier Ind & Sante | Composés de l'imidazol-5-carboxamide, leur procédé de préparation leurs intermédiaires et leur utilisation en thérapeutique. |
| EP1229034B1 (en) | 2001-01-31 | 2005-04-13 | Pfizer Products Inc. | Nicotinamide derivatives and their mimetics as inhibitors of PDE4 isozymes |
| DE10110749A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Substituierte Aminodicarbonsäurederivate |
| AU2003241834A1 (en) | 2002-06-26 | 2004-01-19 | Ono Pharmaceutical Co., Ltd. | Remedy for chronic disease |
| WO2004031118A1 (ja) * | 2002-10-03 | 2004-04-15 | Ono Pharmaceutical Co., Ltd. | Ｌｐａ受容体拮抗剤 |
| WO2011017350A2 (en) | 2009-08-04 | 2011-02-10 | Amira Pharmaceuticals, Inc. | Compounds as lysophosphatidic acid receptor antagonists |
| RU2563639C2 (ru) | 2009-09-25 | 2015-09-20 | Астеллас Фарма Инк. | Замещенные соединения амида |
| GB2474748B (en) | 2009-10-01 | 2011-10-12 | Amira Pharmaceuticals Inc | Polycyclic compounds as lysophosphatidic acid receptor antagonists |
| PH12012500542A1 (en) | 2010-09-24 | 2012-11-12 | Astellas Pharma Inc | Substituted amide compound |
| CN103443098B (zh) * | 2011-01-30 | 2016-03-16 | 广州源生医药科技有限公司 | 作为溶血磷脂酸受体的拮抗剂的化合物、组合物及其应用 |
| EP2765128A1 (en) * | 2013-02-07 | 2014-08-13 | Almirall, S.A. | Substituted benzamides with activity towards EP4 receptors |
| GB201314926D0 (en) | 2013-08-20 | 2013-10-02 | Takeda Pharmaceutical | Novel Compounds |
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2013
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-
2014
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- 2014-08-19 UY UY0001035708A patent/UY35708A/es not_active Application Discontinuation
- 2014-08-20 MA MA38854A patent/MA38854B1/fr unknown
- 2014-08-20 KR KR1020167007214A patent/KR20160045797A/ko not_active Withdrawn
- 2014-08-20 EA EA201690390A patent/EA028818B1/ru not_active IP Right Cessation
- 2014-08-20 PE PE2016000269A patent/PE20160284A1/es not_active Application Discontinuation
- 2014-08-20 US US14/913,135 patent/US10100018B2/en not_active Expired - Fee Related
- 2014-08-20 AU AU2014310404A patent/AU2014310404B2/en not_active Expired - Fee Related
- 2014-08-20 MX MX2016001896A patent/MX2016001896A/es unknown
- 2014-08-20 EP EP14756117.9A patent/EP3036215A1/en not_active Withdrawn
- 2014-08-20 CN CN201480046178.8A patent/CN105473548B/zh not_active Expired - Fee Related
- 2014-08-20 JP JP2016535530A patent/JP6422974B2/ja not_active Expired - Fee Related
- 2014-08-20 HK HK16113982.5A patent/HK1225712A1/zh unknown
- 2014-08-20 US US14/463,780 patent/US9464060B2/en not_active Expired - Fee Related
- 2014-08-20 SG SG11201601250TA patent/SG11201601250TA/en unknown
- 2014-08-20 WO PCT/GB2014/052558 patent/WO2015025164A1/en not_active Ceased
- 2014-08-20 CA CA2921742A patent/CA2921742A1/en not_active Abandoned
- 2014-08-20 TN TN2016000061A patent/TN2016000061A1/en unknown
- 2014-08-20 AR ARP140103129A patent/AR097403A1/es unknown
-
2016
- 2016-01-26 IL IL243780A patent/IL243780A0/en unknown
- 2016-02-03 ZA ZA2016/00753A patent/ZA201600753B/en unknown
- 2016-02-18 PH PH12016500322A patent/PH12016500322A1/en unknown
- 2016-02-19 CR CR20160084A patent/CR20160084A/es unknown
- 2016-02-19 CL CL2016000387A patent/CL2016000387A1/es unknown
-
2018
- 2018-08-20 US US15/999,570 patent/US20190010129A1/en not_active Abandoned
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