KR20160045797A - 리소포스파티드산 수용체 길항제로서의 아미드 유도체 - Google Patents
리소포스파티드산 수용체 길항제로서의 아미드 유도체 Download PDFInfo
- Publication number
- KR20160045797A KR20160045797A KR1020167007214A KR20167007214A KR20160045797A KR 20160045797 A KR20160045797 A KR 20160045797A KR 1020167007214 A KR1020167007214 A KR 1020167007214A KR 20167007214 A KR20167007214 A KR 20167007214A KR 20160045797 A KR20160045797 A KR 20160045797A
- Authority
- KR
- South Korea
- 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.)
- Withdrawn
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- 150000001408 amides Chemical class 0.000 title description 5
- 229940123977 Lysophosphatidic acid receptor antagonist Drugs 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 155
- 150000001875 compounds Chemical class 0.000 claims abstract description 141
- 150000003839 salts Chemical class 0.000 claims abstract description 40
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
- 238000002360 preparation method Methods 0.000 claims abstract description 16
- 230000008569 process Effects 0.000 claims abstract description 11
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 223
- -1 nitro, carboxyl Chemical group 0.000 claims description 159
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 130
- 239000000203 mixture Substances 0.000 claims description 107
- 239000005711 Benzoic acid Substances 0.000 claims description 104
- 235000010233 benzoic acid Nutrition 0.000 claims description 104
- 125000001424 substituent group Chemical group 0.000 claims description 67
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 229910052757 nitrogen Inorganic materials 0.000 claims description 55
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 125000005842 heteroatom Chemical group 0.000 claims description 32
- 229920006395 saturated elastomer Polymers 0.000 claims description 31
- 101001038037 Homo sapiens Lysophosphatidic acid receptor 5 Proteins 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 30
- 102100040404 Lysophosphatidic acid receptor 5 Human genes 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 28
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 27
- 239000011737 fluorine Substances 0.000 claims description 27
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 125000004122 cyclic group Chemical group 0.000 claims description 26
- WRWYGOVGIGCDLE-UHFFFAOYSA-N [O]c1ccccc1F Chemical group [O]c1ccccc1F WRWYGOVGIGCDLE-UHFFFAOYSA-N 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
- 239000000460 chlorine Substances 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 239000001301 oxygen Chemical group 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- 229910052717 sulfur Chemical group 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
- 239000011593 sulfur Chemical group 0.000 claims description 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 101000966782 Homo sapiens Lysophosphatidic acid receptor 1 Proteins 0.000 claims description 12
- 102100040607 Lysophosphatidic acid receptor 1 Human genes 0.000 claims description 12
- 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 12
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 11
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 125000002757 morpholinyl group Chemical group 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000003386 piperidinyl group Chemical group 0.000 claims description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 206010016654 Fibrosis Diseases 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 6
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 230000004761 fibrosis Effects 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 208000024891 symptom Diseases 0.000 claims description 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl 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
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 3
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 208000027753 pain disease Diseases 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 229940124597 therapeutic agent Drugs 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000004890 (C1-C6) alkylamino 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
- 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
- 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
- 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
- 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
- BETITZCZDCWBIT-UHFFFAOYSA-N COc1cccc(CN(Cc2ccc(cc2)C(O)=O)C(=O)c2ccc(Oc3ccccc3F)cc2)c1 Chemical compound COc1cccc(CN(Cc2ccc(cc2)C(O)=O)C(=O)c2ccc(Oc3ccccc3F)cc2)c1 BETITZCZDCWBIT-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
- 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
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- 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
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Classifications
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
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- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
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- C07C235/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/52—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
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- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Peptides Or Proteins (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
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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 |
Publications (1)
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| KR20160045797A true KR20160045797A (ko) | 2016-04-27 |
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| EP (1) | EP3036215A1 (OSRAM) |
| JP (1) | JP6422974B2 (OSRAM) |
| KR (1) | KR20160045797A (OSRAM) |
| CN (1) | CN105473548B (OSRAM) |
| AR (1) | AR097403A1 (OSRAM) |
| AU (1) | AU2014310404B2 (OSRAM) |
| CA (1) | CA2921742A1 (OSRAM) |
| CL (1) | CL2016000387A1 (OSRAM) |
| CR (1) | CR20160084A (OSRAM) |
| EA (1) | EA028818B1 (OSRAM) |
| GB (1) | GB201314926D0 (OSRAM) |
| HK (1) | HK1225712A1 (OSRAM) |
| IL (1) | IL243780A0 (OSRAM) |
| MA (1) | MA38854B1 (OSRAM) |
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| PE (1) | PE20160284A1 (OSRAM) |
| PH (1) | PH12016500322A1 (OSRAM) |
| SG (1) | SG11201601250TA (OSRAM) |
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| UY (1) | UY35708A (OSRAM) |
| WO (1) | WO2015025164A1 (OSRAM) |
| ZA (1) | ZA201600753B (OSRAM) |
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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 |
| MX2022001264A (es) | 2019-07-30 | 2022-02-22 | Taisho Pharmaceutical Co Ltd | Compuesto de urea para antagonizar el receptor del acido lisofosfatidico tipo 1. |
| JP7431961B2 (ja) | 2019-11-15 | 2024-02-15 | ギリアード サイエンシーズ, インコーポレイテッド | Lpa受容体アンタゴニストとしてのトリアゾールカルバメートピリジルスルホンアミド及びその使用 |
| 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 |
| CA3185689A1 (en) | 2020-06-03 | 2021-12-09 | Gilead Sciences, Inc. | Lpa receptor antagonists and uses thereof |
| CN117295717A (zh) | 2021-05-11 | 2023-12-26 | 吉利德科学公司 | Lpa受体拮抗剂及其用途 |
| JP7709612B2 (ja) | 2021-12-08 | 2025-07-16 | ギリアード サイエンシーズ, インコーポレイテッド | Lpa受容体アンタゴニスト及びそれらの使用 |
| 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. |
| ATE293109T1 (de) | 2001-01-31 | 2005-04-15 | Pfizer Prod Inc | Nikotinsäureamid-derivate und ihre mimetika als inhibitoren von pde4-isozyms |
| DE10110749A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Substituierte Aminodicarbonsäurederivate |
| EP1550461A1 (en) * | 2002-06-26 | 2005-07-06 | Ono Pharmaceutical Co., Ltd. | Remedy for chronic disease |
| TW200408393A (en) * | 2002-10-03 | 2004-06-01 | Ono Pharmaceutical Co | Antagonist of lysophosphatidine acid receptor |
| JP2013501064A (ja) * | 2009-08-04 | 2013-01-10 | アミラ ファーマシューティカルス,インコーポレーテッド | リゾホスファチジン酸受容体アンタゴニストとしての化合物 |
| PL2481725T3 (pl) | 2009-09-25 | 2015-08-31 | Astellas Pharma Inc | Podstawiony związek amidowy |
| 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 |
| US8785442B2 (en) * | 2011-01-30 | 2014-07-22 | Curegenix, Inc. | Compound as antagonist of lysophosphatidic acid receptor, composition, and use thereof |
| 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
- 2014-08-18 TW TW103128316A patent/TW201536722A/zh unknown
- 2014-08-19 UY UY0001035708A patent/UY35708A/es not_active Application Discontinuation
- 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 TN TN2016000061A patent/TN2016000061A1/en unknown
- 2014-08-20 EP EP14756117.9A patent/EP3036215A1/en not_active Withdrawn
- 2014-08-20 MX MX2016001896A patent/MX2016001896A/es unknown
- 2014-08-20 KR KR1020167007214A patent/KR20160045797A/ko not_active Withdrawn
- 2014-08-20 PE PE2016000269A patent/PE20160284A1/es not_active Application Discontinuation
- 2014-08-20 MA MA38854A patent/MA38854B1/fr unknown
- 2014-08-20 AU AU2014310404A patent/AU2014310404B2/en not_active Expired - Fee Related
- 2014-08-20 AR ARP140103129A patent/AR097403A1/es unknown
- 2014-08-20 CN CN201480046178.8A patent/CN105473548B/zh not_active Expired - Fee Related
- 2014-08-20 WO PCT/GB2014/052558 patent/WO2015025164A1/en not_active Ceased
- 2014-08-20 EA EA201690390A patent/EA028818B1/ru not_active IP Right Cessation
- 2014-08-20 CA CA2921742A patent/CA2921742A1/en not_active Abandoned
- 2014-08-20 SG SG11201601250TA patent/SG11201601250TA/en unknown
- 2014-08-20 US US14/913,135 patent/US10100018B2/en not_active Expired - Fee Related
- 2014-08-20 JP JP2016535530A patent/JP6422974B2/ja not_active Expired - Fee Related
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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
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2018
- 2018-08-20 US US15/999,570 patent/US20190010129A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| MA38854B1 (fr) | 2018-05-31 |
| EA028818B1 (ru) | 2018-01-31 |
| SG11201601250TA (en) | 2016-03-30 |
| AR097403A1 (es) | 2016-03-09 |
| CL2016000387A1 (es) | 2016-12-16 |
| TW201536722A (zh) | 2015-10-01 |
| CA2921742A1 (en) | 2015-02-26 |
| US20160207880A1 (en) | 2016-07-21 |
| WO2015025164A1 (en) | 2015-02-26 |
| US10100018B2 (en) | 2018-10-16 |
| JP2016528274A (ja) | 2016-09-15 |
| EP3036215A1 (en) | 2016-06-29 |
| CN105473548B (zh) | 2018-03-23 |
| US20190010129A1 (en) | 2019-01-10 |
| AU2014310404B2 (en) | 2018-07-12 |
| CR20160084A (es) | 2016-05-27 |
| EA201690390A1 (ru) | 2016-08-31 |
| MA38854A1 (fr) | 2017-07-31 |
| US9464060B2 (en) | 2016-10-11 |
| IL243780A0 (en) | 2016-04-21 |
| ZA201600753B (en) | 2019-07-31 |
| UY35708A (es) | 2014-12-31 |
| PH12016500322A1 (en) | 2016-05-02 |
| CN105473548A (zh) | 2016-04-06 |
| TN2016000061A1 (en) | 2017-07-05 |
| GB201314926D0 (en) | 2013-10-02 |
| JP6422974B2 (ja) | 2018-11-14 |
| US20150057298A1 (en) | 2015-02-26 |
| MX2016001896A (es) | 2016-05-26 |
| HK1225712A1 (zh) | 2017-09-15 |
| AU2014310404A1 (en) | 2016-03-10 |
| PE20160284A1 (es) | 2016-04-27 |
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