JP2004500326A5 - - Google Patents
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- Publication number
- JP2004500326A5 JP2004500326A5 JP2000620913A JP2000620913A JP2004500326A5 JP 2004500326 A5 JP2004500326 A5 JP 2004500326A5 JP 2000620913 A JP2000620913 A JP 2000620913A JP 2000620913 A JP2000620913 A JP 2000620913A JP 2004500326 A5 JP2004500326 A5 JP 2004500326A5
- Authority
- JP
- Japan
- Prior art keywords
- tetrahydro
- oxo
- naphthyridin
- nonanoic acid
- pyrimidin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 80
- 150000001875 compounds Chemical class 0.000 claims 52
- -1 hydroxy, hydroxy Chemical group 0.000 claims 40
- 229910052739 hydrogen Inorganic materials 0.000 claims 34
- 239000001257 hydrogen Substances 0.000 claims 34
- 125000003118 aryl group Chemical group 0.000 claims 27
- 125000001424 substituent group Chemical group 0.000 claims 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 20
- 125000003545 alkoxy group Chemical group 0.000 claims 20
- 125000004321 azepin-2-yl group Chemical group [H]N1C([H])=C([H])C([H])=C([H])C([H])=C1* 0.000 claims 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 15
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 150000002431 hydrogen Chemical class 0.000 claims 14
- 125000003282 alkyl amino group Chemical group 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 11
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 10
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 10
- 241000124008 Mammalia Species 0.000 claims 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 9
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 9
- 238000004519 manufacturing process Methods 0.000 claims 9
- 125000004076 pyridyl group Chemical group 0.000 claims 9
- 125000004442 acylamino group Chemical group 0.000 claims 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 7
- 125000004414 alkyl thio group Chemical group 0.000 claims 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 6
- 230000003042 antagnostic effect Effects 0.000 claims 6
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 5
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 5
- 150000001721 carbon Chemical group 0.000 claims 5
- 239000003112 inhibitor Substances 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 4
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 4
- 208000006386 Bone Resorption Diseases 0.000 claims 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 4
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 4
- 230000024279 bone resorption Effects 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 102000006495 integrins Human genes 0.000 claims 4
- 108010044426 integrins Proteins 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims 4
- YRKLRKQGAWLYDP-IBGZPJMESA-N (2s)-2-(2-methoxypyrimidin-5-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=NC(OC)=NC=C1[C@@H](C(O)=O)CCC(=O)CCCCC1=CC=C(CCCN2)C2=N1 YRKLRKQGAWLYDP-IBGZPJMESA-N 0.000 claims 3
- KYIUESBVXDONBH-FQEVSTJZSA-N (2s)-2-(2-methylpyrimidin-5-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=NC(C)=NC=C1[C@@H](C(O)=O)CCC(=O)CCCCC1=CC=C(CCCN2)C2=N1 KYIUESBVXDONBH-FQEVSTJZSA-N 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 230000004614 tumor growth Effects 0.000 claims 3
- AYDDTLCITNWPKO-JOCHJYFZSA-N (2R)-2-(2,3-dihydro-1-benzofuran-6-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound OC(=O)[C@H](CCC(=O)CCCCc1ccc2CCCNc2n1)c1ccc2CCOc2c1 AYDDTLCITNWPKO-JOCHJYFZSA-N 0.000 claims 2
- HGMOQTQPWKYBJF-HXUWFJFHSA-N (2R)-2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-7-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound OC(=O)[C@H](CCC(=O)CCCCc1ccc2CCCNc2n1)c1cnc2OCCOc2c1 HGMOQTQPWKYBJF-HXUWFJFHSA-N 0.000 claims 2
- DGUILINMWZCQNV-OAQYLSRUSA-N (2R)-2-(2-cyclopropylpyrimidin-5-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound OC(=O)[C@H](CCC(=O)CCCCc1ccc2CCCNc2n1)c1cnc(nc1)C1CC1 DGUILINMWZCQNV-OAQYLSRUSA-N 0.000 claims 2
- WFGOHYOLAUUXQA-HXUWFJFHSA-N (2R)-2-(2-methylpyrimidin-5-yl)-9-(3-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)-5-oxononanoic acid Chemical compound Cc1ncc(cn1)[C@@H](CCC(=O)CCCCc1nc2NCCCc2cc1C)C(O)=O WFGOHYOLAUUXQA-HXUWFJFHSA-N 0.000 claims 2
- GORJZZGBALVRQI-OAQYLSRUSA-N (2R)-2-(6-ethoxypyridin-3-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound CCOc1ccc(cn1)[C@@H](CCC(=O)CCCCc1ccc2CCCNc2n1)C(O)=O GORJZZGBALVRQI-OAQYLSRUSA-N 0.000 claims 2
- CAVMYLVDMTYJKW-GFOWMXPYSA-N (2R)-5-hydroxy-2-(2-methylpyrimidin-5-yl)-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound CC1=NC=C(C=N1)[C@H](C(=O)O)CCC(CCCCC1=NC=2NCCCC2C=C1)O CAVMYLVDMTYJKW-GFOWMXPYSA-N 0.000 claims 2
- CITGFEDLBWRGEJ-OZAIVSQSSA-N (2R)-5-hydroxy-2-quinolin-3-yl-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound N1=CC(=CC2=CC=CC=C12)[C@H](C(=O)O)CCC(CCCCC1=NC=2NCCCC2C=C1)O CITGFEDLBWRGEJ-OZAIVSQSSA-N 0.000 claims 2
- QVQCBDGBIZVTMM-OAQYLSRUSA-N (2R)-5-oxo-2-(2-propan-2-ylpyrimidin-5-yl)-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound CC(C)c1ncc(cn1)[C@@H](CCC(=O)CCCCc1ccc2CCCNc2n1)C(O)=O QVQCBDGBIZVTMM-OAQYLSRUSA-N 0.000 claims 2
- LZQMLZXBYVIKNA-LJQANCHMSA-N (2R)-5-oxo-2-pyrimidin-5-yl-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound OC(=O)[C@H](CCC(=O)CCCCc1ccc2CCCNc2n1)c1cncnc1 LZQMLZXBYVIKNA-LJQANCHMSA-N 0.000 claims 2
- HNGVWTANWOACNX-OAQYLSRUSA-N (2R)-7,7-dimethyl-2-(2-methylpyrimidin-5-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound Cc1ncc(cn1)[C@@H](CCC(=O)CC(C)(C)CCc1ccc2CCCNc2n1)C(O)=O HNGVWTANWOACNX-OAQYLSRUSA-N 0.000 claims 2
- OEJMPXAXGWKGQE-QFIPXVFZSA-N (2S)-2-(1-benzofuran-6-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound OC(=O)[C@@H](CCC(=O)CCCCc1ccc2CCCNc2n1)c1ccc2ccoc2c1 OEJMPXAXGWKGQE-QFIPXVFZSA-N 0.000 claims 2
- HGMOQTQPWKYBJF-FQEVSTJZSA-N (2S)-2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-7-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound OC(=O)[C@@H](CCC(=O)CCCCc1ccc2CCCNc2n1)c1cnc2OCCOc2c1 HGMOQTQPWKYBJF-FQEVSTJZSA-N 0.000 claims 2
- DGUILINMWZCQNV-NRFANRHFSA-N (2S)-2-(2-cyclopropylpyrimidin-5-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound OC(=O)[C@@H](CCC(=O)CCCCc1ccc2CCCNc2n1)c1cnc(nc1)C1CC1 DGUILINMWZCQNV-NRFANRHFSA-N 0.000 claims 2
- CBEYPRXKRIRFIJ-FQEVSTJZSA-N (2S)-2-(2-methylpyrimidin-5-yl)-7-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound Cc1ncc(cn1)[C@H](CCCCC(=O)CCc1ccc2CCCNc2n1)C(O)=O CBEYPRXKRIRFIJ-FQEVSTJZSA-N 0.000 claims 2
- FDHJJPVHTYVRIJ-NRFANRHFSA-N (2S)-2-(5-methoxypyridin-3-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound COc1cncc(c1)[C@H](CCC(=O)CCCCc1ccc2CCCNc2n1)C(O)=O FDHJJPVHTYVRIJ-NRFANRHFSA-N 0.000 claims 2
- LUCRVWWAYGIHAB-IBGZPJMESA-N (2S)-2-(5-methylpyrazin-2-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound Cc1cnc(cn1)[C@H](CCC(=O)CCCCc1ccc2CCCNc2n1)C(O)=O LUCRVWWAYGIHAB-IBGZPJMESA-N 0.000 claims 2
- GORJZZGBALVRQI-NRFANRHFSA-N (2S)-2-(6-ethoxypyridin-3-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound CCOc1ccc(cn1)[C@H](CCC(=O)CCCCc1ccc2CCCNc2n1)C(O)=O GORJZZGBALVRQI-NRFANRHFSA-N 0.000 claims 2
- CAVMYLVDMTYJKW-ANYOKISRSA-N (2S)-5-hydroxy-2-(2-methylpyrimidin-5-yl)-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound CC1=NC=C(C=N1)[C@@H](C(=O)O)CCC(CCCCC1=NC=2NCCCC2C=C1)O CAVMYLVDMTYJKW-ANYOKISRSA-N 0.000 claims 2
- CITGFEDLBWRGEJ-WCSIJFPASA-N (2S)-5-hydroxy-2-quinolin-3-yl-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound N1=CC(=CC2=CC=CC=C12)[C@@H](C(=O)O)CCC(CCCCC1=NC=2NCCCC2C=C1)O CITGFEDLBWRGEJ-WCSIJFPASA-N 0.000 claims 2
- QVQCBDGBIZVTMM-NRFANRHFSA-N (2S)-5-oxo-2-(2-propan-2-ylpyrimidin-5-yl)-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound CC(C)c1ncc(cn1)[C@H](CCC(=O)CCCCc1ccc2CCCNc2n1)C(O)=O QVQCBDGBIZVTMM-NRFANRHFSA-N 0.000 claims 2
- LZQMLZXBYVIKNA-IBGZPJMESA-N (2S)-5-oxo-2-pyrimidin-5-yl-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound OC(=O)[C@@H](CCC(=O)CCCCc1ccc2CCCNc2n1)c1cncnc1 LZQMLZXBYVIKNA-IBGZPJMESA-N 0.000 claims 2
- HNGVWTANWOACNX-NRFANRHFSA-N (2S)-7,7-dimethyl-2-(2-methylpyrimidin-5-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound Cc1ncc(cn1)[C@H](CCC(=O)CC(C)(C)CCc1ccc2CCCNc2n1)C(O)=O HNGVWTANWOACNX-NRFANRHFSA-N 0.000 claims 2
- OEJMPXAXGWKGQE-JOCHJYFZSA-N (2r)-2-(1-benzofuran-6-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=C2C=COC2=CC([C@@H](CCC(=O)CCCCC=2N=C3NCCCC3=CC=2)C(=O)O)=C1 OEJMPXAXGWKGQE-JOCHJYFZSA-N 0.000 claims 2
- VNNKGLKYUJUPHO-HXUWFJFHSA-N (2r)-2-(2-ethoxypyrimidin-5-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=NC(OCC)=NC=C1[C@H](C(O)=O)CCC(=O)CCCCC1=CC=C(CCCN2)C2=N1 VNNKGLKYUJUPHO-HXUWFJFHSA-N 0.000 claims 2
- YRKLRKQGAWLYDP-LJQANCHMSA-N (2r)-2-(2-methoxypyrimidin-5-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=NC(OC)=NC=C1[C@H](C(O)=O)CCC(=O)CCCCC1=CC=C(CCCN2)C2=N1 YRKLRKQGAWLYDP-LJQANCHMSA-N 0.000 claims 2
- MWPVEEPFXLFXMA-LJQANCHMSA-N (2r)-2-(2-methoxypyrimidin-5-yl)-9-(3-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)-5-oxononanoic acid Chemical compound C1=NC(OC)=NC=C1[C@H](C(O)=O)CCC(=O)CCCCC(C(=C1)C)=NC2=C1CCCN2 MWPVEEPFXLFXMA-LJQANCHMSA-N 0.000 claims 2
- KYIUESBVXDONBH-HXUWFJFHSA-N (2r)-2-(2-methylpyrimidin-5-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=NC(C)=NC=C1[C@H](C(O)=O)CCC(=O)CCCCC1=CC=C(CCCN2)C2=N1 KYIUESBVXDONBH-HXUWFJFHSA-N 0.000 claims 2
- CBEYPRXKRIRFIJ-HXUWFJFHSA-N (2r)-2-(2-methylpyrimidin-5-yl)-7-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=NC(C)=NC=C1[C@H](C(O)=O)CCCCC(=O)CCC1=CC=C(CCCN2)C2=N1 CBEYPRXKRIRFIJ-HXUWFJFHSA-N 0.000 claims 2
- CKSPSTLZBJXIKM-MZVUKIKXSA-N (2r)-2-(2-methylpyrimidin-5-yl)-9-(6-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)-5-oxononanoic acid Chemical compound C1([C@H](C(O)=O)CCC(=O)CCCCC=2N=C3NCC(CC3=CC=2)C)=CN=C(C)N=C1 CKSPSTLZBJXIKM-MZVUKIKXSA-N 0.000 claims 2
- RGRLZRNIQDXERL-OAQYLSRUSA-N (2r)-2-(2-tert-butylpyrimidin-5-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=NC(C(C)(C)C)=NC=C1[C@H](C(O)=O)CCC(=O)CCCCC1=CC=C(CCCN2)C2=N1 RGRLZRNIQDXERL-OAQYLSRUSA-N 0.000 claims 2
- FDHJJPVHTYVRIJ-OAQYLSRUSA-N (2r)-2-(5-methoxypyridin-3-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound COC1=CN=CC([C@@H](CCC(=O)CCCCC=2N=C3NCCCC3=CC=2)C(O)=O)=C1 FDHJJPVHTYVRIJ-OAQYLSRUSA-N 0.000 claims 2
- LUCRVWWAYGIHAB-LJQANCHMSA-N (2r)-2-(5-methylpyrazin-2-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=NC(C)=CN=C1[C@H](C(O)=O)CCC(=O)CCCCC1=CC=C(CCCN2)C2=N1 LUCRVWWAYGIHAB-LJQANCHMSA-N 0.000 claims 2
- IGYRCQAUOKNOCX-GOSISDBHSA-N (2r)-2-(6-methoxypyridazin-3-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound N1=NC(OC)=CC=C1[C@H](C(O)=O)CCC(=O)CCCCC1=CC=C(CCCN2)C2=N1 IGYRCQAUOKNOCX-GOSISDBHSA-N 0.000 claims 2
- XAYSGSCETLFAQC-HXUWFJFHSA-N (2r)-2-(6-methoxypyridin-3-yl)-9-(3-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)-5-oxononanoic acid Chemical compound C1=NC(OC)=CC=C1[C@H](C(O)=O)CCC(=O)CCCCC(C(=C1)C)=NC2=C1CCCN2 XAYSGSCETLFAQC-HXUWFJFHSA-N 0.000 claims 2
- ACNBIPIEGANMHS-HXUWFJFHSA-N (2r)-2-[2-(dimethylamino)pyrimidin-5-yl]-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=NC(N(C)C)=NC=C1[C@H](C(O)=O)CCC(=O)CCCCC1=CC=C(CCCN2)C2=N1 ACNBIPIEGANMHS-HXUWFJFHSA-N 0.000 claims 2
- QHDQGGPLXWADGC-LJQANCHMSA-N (2r)-2-[2-(methylamino)pyrimidin-5-yl]-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=NC(NC)=NC=C1[C@H](C(O)=O)CCC(=O)CCCCC1=CC=C(CCCN2)C2=N1 QHDQGGPLXWADGC-LJQANCHMSA-N 0.000 claims 2
- UPNUQZLHTJMHSH-GOSISDBHSA-N (2r)-5-oxo-2-pyrazin-2-yl-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1([C@@H](CCC(=O)CCCCC=2N=C3NCCCC3=CC=2)C(=O)O)=CN=CC=N1 UPNUQZLHTJMHSH-GOSISDBHSA-N 0.000 claims 2
- KCXMGCPGJGKFNN-HSZRJFAPSA-N (2r)-5-oxo-2-quinolin-3-yl-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=CC=CC2=CC([C@@H](CCC(=O)CCCCC=3N=C4NCCCC4=CC=3)C(=O)O)=CN=C21 KCXMGCPGJGKFNN-HSZRJFAPSA-N 0.000 claims 2
- PXKRBNCCUNMPMJ-HXUWFJFHSA-N (2r)-5-oxo-2-quinoxalin-2-yl-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=CC=CC2=NC([C@@H](CCC(=O)CCCCC=3N=C4NCCCC4=CC=3)C(=O)O)=CN=C21 PXKRBNCCUNMPMJ-HXUWFJFHSA-N 0.000 claims 2
- IRXDEOIVUJASDE-GOSISDBHSA-N (2r)-9-(3-bromo-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)-2-(2-methylpyrimidin-5-yl)-5-oxononanoic acid Chemical compound C1=NC(C)=NC=C1[C@H](C(O)=O)CCC(=O)CCCCC(C(=C1)Br)=NC2=C1CCCN2 IRXDEOIVUJASDE-GOSISDBHSA-N 0.000 claims 2
- LNBYIIKGGCJLKI-OAQYLSRUSA-N (2r)-9-(3-cyclopropyl-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)-2-(2-ethoxypyrimidin-5-yl)-5-oxononanoic acid Chemical compound C1=NC(OCC)=NC=C1[C@H](C(O)=O)CCC(=O)CCCCC(C(=C1)C2CC2)=NC2=C1CCCN2 LNBYIIKGGCJLKI-OAQYLSRUSA-N 0.000 claims 2
- WBNWAXSZYLDMNX-HXUWFJFHSA-N (2r)-9-(3-cyclopropyl-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)-2-(2-methoxypyrimidin-5-yl)-5-oxononanoic acid Chemical compound C1=NC(OC)=NC=C1[C@H](C(O)=O)CCC(=O)CCCCC(C(=C1)C2CC2)=NC2=C1CCCN2 WBNWAXSZYLDMNX-HXUWFJFHSA-N 0.000 claims 2
- FGXZHWSARJMWBB-OAQYLSRUSA-N (2r)-9-(3-cyclopropyl-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)-2-(2-methylpyrimidin-5-yl)-5-oxononanoic acid Chemical compound C1=NC(C)=NC=C1[C@H](C(O)=O)CCC(=O)CCCCC(C(=C1)C2CC2)=NC2=C1CCCN2 FGXZHWSARJMWBB-OAQYLSRUSA-N 0.000 claims 2
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| US11192889B2 (en) * | 2016-07-05 | 2021-12-07 | The Rockefeller University | Tetrahydronaphthyridinepentanamide integrin antagonists |
| EP3509590A4 (en) | 2016-09-07 | 2020-12-02 | Pliant Therapeutics, Inc. | N-ACYL AMINO ACID COMPOUNDS AND METHODS OF USE |
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| WO1998018460A1 (en) * | 1996-10-30 | 1998-05-07 | Merck & Co., Inc. | Integrin antagonists |
| EP0946164A4 (en) | 1996-10-30 | 2000-08-23 | Merck & Co Inc | INTEGRIN ANTAGONISTS |
| JP2001509176A (ja) | 1997-01-17 | 2001-07-10 | メルク エンド カンパニー インコーポレーテッド | インテグリンアンタゴニスト |
| US6048861A (en) * | 1997-12-17 | 2000-04-11 | Merck & Co., Inc. | Integrin receptor antagonists |
| KR20010033248A (ko) * | 1997-12-17 | 2001-04-25 | 폴락 돈나 엘. | 인테그린 수용체 길항제 |
| CA2315370A1 (en) | 1997-12-17 | 1999-06-24 | Merck & Co., Inc. | Integrin receptor antagonists |
| EA003095B1 (ru) | 1997-12-17 | 2002-12-26 | Мерк Энд Ко., Инк. | Антагонисты рецепторов интегринов |
| US6017926A (en) | 1997-12-17 | 2000-01-25 | Merck & Co., Inc. | Integrin receptor antagonists |
| CA2315232A1 (en) | 1997-12-17 | 1999-06-24 | Merck & Co., Inc. | Integrin receptor antagonists |
-
2000
- 2000-05-30 CN CNA00811157XA patent/CN1589145A/zh active Pending
- 2000-05-30 ES ES00942652T patent/ES2288861T3/es not_active Expired - Lifetime
- 2000-05-30 PT PT00942652T patent/PT1187592E/pt unknown
- 2000-05-30 JP JP2000620913A patent/JP3808707B2/ja not_active Expired - Fee Related
- 2000-05-30 DK DK00942652T patent/DK1187592T3/da active
- 2000-05-30 EP EP00942652A patent/EP1187592B1/en not_active Expired - Lifetime
- 2000-05-30 CA CA002373937A patent/CA2373937A1/en not_active Abandoned
- 2000-05-30 DZ DZ003263A patent/DZ3263A1/fr active
- 2000-05-30 HU HU0302468A patent/HUP0302468A2/hu unknown
- 2000-05-30 CZ CZ20014308A patent/CZ20014308A3/cs unknown
- 2000-05-30 KR KR1020017015498A patent/KR20020021380A/ko not_active Ceased
- 2000-05-30 PL PL00353364A patent/PL353364A1/xx not_active Application Discontinuation
- 2000-05-30 EE EEP200100642A patent/EE200100642A/xx unknown
- 2000-05-30 EA EA200101272A patent/EA200101272A1/ru unknown
- 2000-05-30 AT AT00942652T patent/ATE368462T1/de not_active IP Right Cessation
- 2000-05-30 DE DE60035779T patent/DE60035779T2/de not_active Expired - Fee Related
- 2000-05-30 WO PCT/US2000/014901 patent/WO2000072801A2/en not_active Ceased
- 2000-05-30 HR HR20010895A patent/HRP20010895A2/xx not_active Application Discontinuation
- 2000-05-30 IL IL14637800A patent/IL146378A0/xx unknown
- 2000-05-30 SK SK1744-2001A patent/SK17442001A3/sk unknown
- 2000-05-30 TR TR2001/03431T patent/TR200103431T2/xx unknown
- 2000-05-30 AU AU57246/00A patent/AU749351B2/en not_active Ceased
- 2000-05-30 BR BR0011108-2A patent/BR0011108A/pt not_active IP Right Cessation
- 2000-05-31 US US09/583,522 patent/US6410526B1/en not_active Expired - Fee Related
-
2001
- 2001-11-13 IS IS6157A patent/IS6157A/is unknown
- 2001-11-30 NO NO20015858A patent/NO323906B1/no not_active IP Right Cessation
- 2001-12-18 BG BG106232A patent/BG106232A/xx unknown
-
2006
- 2006-03-29 JP JP2006091925A patent/JP2006206604A/ja not_active Withdrawn
- 2006-03-29 JP JP2006091926A patent/JP2006232844A/ja not_active Withdrawn
-
2007
- 2007-09-27 CY CY20071101242T patent/CY1107746T1/el unknown
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