JP2003520271A5 - - Google Patents
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- JP2003520271A5 JP2003520271A5 JP2001553266A JP2001553266A JP2003520271A5 JP 2003520271 A5 JP2003520271 A5 JP 2003520271A5 JP 2001553266 A JP2001553266 A JP 2001553266A JP 2001553266 A JP2001553266 A JP 2001553266A JP 2003520271 A5 JP2003520271 A5 JP 2003520271A5
- Authority
- JP
- Japan
- Prior art keywords
- nonanoic acid
- amino
- pyrimidin
- alkyl
- pyridin
- 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- Withdrawn
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- 125000000217 alkyl group Chemical group 0.000 description 41
- -1 trifluoromethoxy, trifluoroethoxy Chemical group 0.000 description 32
- 239000000203 mixture Substances 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 17
- 125000003118 aryl group Chemical group 0.000 description 11
- 230000003042 antagnostic effect Effects 0.000 description 10
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 125000004321 azepin-2-yl group Chemical group [H]N1C([H])=C([H])C([H])=C([H])C([H])=C1* 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 102000006495 integrins Human genes 0.000 description 5
- 108010044426 integrins Proteins 0.000 description 5
- WDUCCRCCNFQPND-LURJTMIESA-N (2S)-2-(6-methoxypyridin-3-yl)propanoic acid Chemical compound COC1=CC=C(C=N1)[C@@H](C(=O)O)C WDUCCRCCNFQPND-LURJTMIESA-N 0.000 description 4
- WDUCCRCCNFQPND-ZCFIWIBFSA-N (2r)-2-(6-methoxypyridin-3-yl)propanoic acid Chemical compound COC1=CC=C([C@@H](C)C(O)=O)C=N1 WDUCCRCCNFQPND-ZCFIWIBFSA-N 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000004442 acylamino group Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 206010061289 metastatic neoplasm Diseases 0.000 description 4
- 230000004614 tumor growth Effects 0.000 description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 3
- 206010012689 Diabetic retinopathy Diseases 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 description 3
- 230000033115 angiogenesis Effects 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 3
- 230000009977 dual effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- 208000002780 macular degeneration Diseases 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000005493 quinolyl group Chemical group 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 208000037803 restenosis Diseases 0.000 description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 3
- QSXLNPJVCMDNMJ-LJQANCHMSA-N (2R)-2-(2-ethoxypyrimidin-5-yl)-9-[6-(ethylamino)pyridin-2-yl]nonanoic acid Chemical compound CCNc1cccc(CCCCCCC[C@@H](C(O)=O)c2cnc(OCC)nc2)n1 QSXLNPJVCMDNMJ-LJQANCHMSA-N 0.000 description 2
- KYFKMRYPDPIWTB-GOSISDBHSA-N (2R)-2-(2-ethoxypyrimidin-5-yl)-9-[6-(methylamino)pyridin-2-yl]nonanoic acid Chemical compound CCOc1ncc(cn1)[C@@H](CCCCCCCc1cccc(NC)n1)C(O)=O KYFKMRYPDPIWTB-GOSISDBHSA-N 0.000 description 2
- PEDHXPMFOQNWDK-QGZVFWFLSA-N (2R)-2-(2-methoxypyrimidin-5-yl)-9-[6-(methylamino)pyridin-2-yl]nonanoic acid Chemical compound CNc1cccc(CCCCCCC[C@@H](C(O)=O)c2cnc(OC)nc2)n1 PEDHXPMFOQNWDK-QGZVFWFLSA-N 0.000 description 2
- AWYWMTHHAQWPBM-MRXNPFEDSA-N (2R)-2-(2-methylpyrimidin-5-yl)-10-oxo-10-(1,4,5,6-tetrahydropyrimidin-2-ylamino)decanoic acid Chemical compound Cc1ncc(cn1)[C@@H](CCCCCCCC(=O)NC1=NCCCN1)C(O)=O AWYWMTHHAQWPBM-MRXNPFEDSA-N 0.000 description 2
- OPYCHDDDPARINO-IBGZPJMESA-N (2R)-2-quinolin-3-yl-3-[5-(1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-6-yl)pentanoylamino]propanoic acid Chemical compound OC(=O)[C@@H](CNC(=O)CCCCc1ccc2NCCNc2n1)c1cnc2ccccc2c1 OPYCHDDDPARINO-IBGZPJMESA-N 0.000 description 2
- KDHUGBWGQNYIQB-GOSISDBHSA-N (2R)-9-[6-(ethylamino)pyridin-2-yl]-2-(2-methoxypyrimidin-5-yl)nonanoic acid Chemical compound CCNc1cccc(CCCCCCC[C@@H](C(O)=O)c2cnc(OC)nc2)n1 KDHUGBWGQNYIQB-GOSISDBHSA-N 0.000 description 2
- QSXLNPJVCMDNMJ-IBGZPJMESA-N (2S)-2-(2-ethoxypyrimidin-5-yl)-9-[6-(ethylamino)pyridin-2-yl]nonanoic acid Chemical compound CCNc1cccc(CCCCCCC[C@H](C(O)=O)c2cnc(OCC)nc2)n1 QSXLNPJVCMDNMJ-IBGZPJMESA-N 0.000 description 2
- KYFKMRYPDPIWTB-SFHVURJKSA-N (2S)-2-(2-ethoxypyrimidin-5-yl)-9-[6-(methylamino)pyridin-2-yl]nonanoic acid Chemical compound CCOc1ncc(cn1)[C@H](CCCCCCCc1cccc(NC)n1)C(O)=O KYFKMRYPDPIWTB-SFHVURJKSA-N 0.000 description 2
- PEDHXPMFOQNWDK-KRWDZBQOSA-N (2S)-2-(2-methoxypyrimidin-5-yl)-9-[6-(methylamino)pyridin-2-yl]nonanoic acid Chemical compound CNc1cccc(CCCCCCC[C@H](C(O)=O)c2cnc(OC)nc2)n1 PEDHXPMFOQNWDK-KRWDZBQOSA-N 0.000 description 2
- AWYWMTHHAQWPBM-INIZCTEOSA-N (2S)-2-(2-methylpyrimidin-5-yl)-10-oxo-10-(1,4,5,6-tetrahydropyrimidin-2-ylamino)decanoic acid Chemical compound Cc1ncc(cn1)[C@H](CCCCCCCC(=O)NC1=NCCCN1)C(O)=O AWYWMTHHAQWPBM-INIZCTEOSA-N 0.000 description 2
- KDHUGBWGQNYIQB-SFHVURJKSA-N (2S)-9-[6-(ethylamino)pyridin-2-yl]-2-(2-methoxypyrimidin-5-yl)nonanoic acid Chemical compound CCNc1cccc(CCCCCCC[C@H](C(O)=O)c2cnc(OC)nc2)n1 KDHUGBWGQNYIQB-SFHVURJKSA-N 0.000 description 2
- OPYCHDDDPARINO-LJQANCHMSA-N (2s)-2-quinolin-3-yl-3-[5-(1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-6-yl)pentanoylamino]propanoic acid Chemical compound C1=CC=CC2=CC([C@@H](CNC(=O)CCCCC=3N=C4NCCNC4=CC=3)C(=O)O)=CN=C21 OPYCHDDDPARINO-LJQANCHMSA-N 0.000 description 2
- UEAARPQIXXQIAV-MRXNPFEDSA-N (3r)-3-(2-ethoxypyrimidin-5-yl)-9-[2-(ethylamino)pyrimidin-4-yl]nonanoic acid Chemical compound CCNC1=NC=CC(CCCCCC[C@H](CC(O)=O)C=2C=NC(OCC)=NC=2)=N1 UEAARPQIXXQIAV-MRXNPFEDSA-N 0.000 description 2
- GIWIXAZUOFJHSH-HXUWFJFHSA-N (3r)-3-[5-(3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-6-yl)pentanoylamino]-3-quinolin-3-ylpropanoic acid Chemical compound C1=CC=CC2=CC([C@H](NC(=O)CCCCC=3N=C4NCCOC4=CC=3)CC(=O)O)=CN=C21 GIWIXAZUOFJHSH-HXUWFJFHSA-N 0.000 description 2
- NDKSDRWJWLNIIF-QGZVFWFLSA-N (3r)-9-(2,3-dihydro-1h-pyrrolo[2,3-b]pyridin-6-yl)-3-(2-methylpyrimidin-5-yl)nonanoic acid Chemical compound C1=NC(C)=NC=C1[C@@H](CC(O)=O)CCCCCCC1=CC=C(CCN2)C2=N1 NDKSDRWJWLNIIF-QGZVFWFLSA-N 0.000 description 2
- GYQWSGPGWQIRDK-CYBMUJFWSA-N (3r)-9-(2,6-diaminopyrimidin-4-yl)-3-(2-methylpyrimidin-5-yl)nonanoic acid Chemical compound C1=NC(C)=NC=C1[C@@H](CC(O)=O)CCCCCCC1=CC(N)=NC(N)=N1 GYQWSGPGWQIRDK-CYBMUJFWSA-N 0.000 description 2
- VEJIHHNAPVFTIX-OAHLLOKOSA-N (3r)-9-(2,6-diaminopyrimidin-4-yl)-3-quinolin-3-ylnonanoic acid Chemical compound NC1=NC(N)=CC(CCCCCC[C@H](CC(O)=O)C=2C=C3C=CC=CC3=NC=2)=N1 VEJIHHNAPVFTIX-OAHLLOKOSA-N 0.000 description 2
- WLGGRYVUWIAQNO-QGZVFWFLSA-N (3r)-9-[6-(ethylamino)pyridin-2-yl]-3-(2-methylpyrimidin-5-yl)nonanoic acid Chemical compound CCNC1=CC=CC(CCCCCC[C@H](CC(O)=O)C=2C=NC(C)=NC=2)=N1 WLGGRYVUWIAQNO-QGZVFWFLSA-N 0.000 description 2
- AJRXGUGHNUPKPA-MRXNPFEDSA-N (3r)-9-[6-(methylamino)pyridin-2-yl]-3-(2-methylpyrimidin-5-yl)nonanoic acid Chemical compound CNC1=CC=CC(CCCCCC[C@H](CC(O)=O)C=2C=NC(C)=NC=2)=N1 AJRXGUGHNUPKPA-MRXNPFEDSA-N 0.000 description 2
- XAUMHHQRAGTYON-OAHLLOKOSA-N (3r)-9-[6-(methylamino)pyridin-2-yl]-3-pyrimidin-5-ylnonanoic acid Chemical compound CNC1=CC=CC(CCCCCC[C@H](CC(O)=O)C=2C=NC=NC=2)=N1 XAUMHHQRAGTYON-OAHLLOKOSA-N 0.000 description 2
- PWXAAPNZAANJNH-QGZVFWFLSA-N (3r)-9-[6-(methylamino)pyridin-2-yl]-3-quinoxalin-2-ylnonanoic acid Chemical compound CNC1=CC=CC(CCCCCC[C@H](CC(O)=O)C=2N=C3C=CC=CC3=NC=2)=N1 PWXAAPNZAANJNH-QGZVFWFLSA-N 0.000 description 2
- IYVLNCGDRIBSON-QGZVFWFLSA-N (3r)-9-[6-amino-2-(ethylamino)pyrimidin-4-yl]-3-(2,3-dihydro-1-benzofuran-6-yl)nonanoic acid Chemical compound CCNC1=NC(N)=CC(CCCCCC[C@H](CC(O)=O)C=2C=C3OCCC3=CC=2)=N1 IYVLNCGDRIBSON-QGZVFWFLSA-N 0.000 description 2
- GMBMWLGJYVBWPA-OAHLLOKOSA-N (3r)-9-[6-amino-2-(ethylamino)pyrimidin-4-yl]-3-(2-ethoxypyrimidin-5-yl)nonanoic acid Chemical compound CCNC1=NC(N)=CC(CCCCCC[C@H](CC(O)=O)C=2C=NC(OCC)=NC=2)=N1 GMBMWLGJYVBWPA-OAHLLOKOSA-N 0.000 description 2
- PUAXFUCQWQYYSP-CQSZACIVSA-N (3r)-9-[6-amino-2-(ethylamino)pyrimidin-4-yl]-3-(2-methoxypyrimidin-5-yl)nonanoic acid Chemical compound CCNC1=NC(N)=CC(CCCCCC[C@H](CC(O)=O)C=2C=NC(OC)=NC=2)=N1 PUAXFUCQWQYYSP-CQSZACIVSA-N 0.000 description 2
- JHVZPGUNRYRABX-OAHLLOKOSA-N (3r)-9-[6-amino-2-(ethylamino)pyrimidin-4-yl]-3-(2-methylpyrimidin-5-yl)nonanoic acid Chemical compound CCNC1=NC(N)=CC(CCCCCC[C@H](CC(O)=O)C=2C=NC(C)=NC=2)=N1 JHVZPGUNRYRABX-OAHLLOKOSA-N 0.000 description 2
- APUMQXXPOIAIJC-OAHLLOKOSA-N (3r)-9-[6-amino-2-(ethylamino)pyrimidin-4-yl]-3-(6-methoxypyridin-3-yl)nonanoic acid Chemical compound CCNC1=NC(N)=CC(CCCCCC[C@H](CC(O)=O)C=2C=NC(OC)=CC=2)=N1 APUMQXXPOIAIJC-OAHLLOKOSA-N 0.000 description 2
- UEAARPQIXXQIAV-INIZCTEOSA-N (3s)-3-(2-ethoxypyrimidin-5-yl)-9-[2-(ethylamino)pyrimidin-4-yl]nonanoic acid Chemical compound CCNC1=NC=CC(CCCCCC[C@@H](CC(O)=O)C=2C=NC(OCC)=NC=2)=N1 UEAARPQIXXQIAV-INIZCTEOSA-N 0.000 description 2
- GYCOITXBHQCENR-IBGZPJMESA-N (3s)-3-(2-methylpyrimidin-5-yl)-9-(6,7,8,9-tetrahydro-5h-pyrido[2,3-b]azepin-2-yl)nonanoic acid Chemical compound C1=NC(C)=NC=C1[C@H](CC(O)=O)CCCCCCC1=CC=C(CCCCN2)C2=N1 GYCOITXBHQCENR-IBGZPJMESA-N 0.000 description 2
- GYQWSGPGWQIRDK-ZDUSSCGKSA-N (3s)-9-(2,6-diaminopyrimidin-4-yl)-3-(2-methylpyrimidin-5-yl)nonanoic acid Chemical compound C1=NC(C)=NC=C1[C@H](CC(O)=O)CCCCCCC1=CC(N)=NC(N)=N1 GYQWSGPGWQIRDK-ZDUSSCGKSA-N 0.000 description 2
- VEJIHHNAPVFTIX-HNNXBMFYSA-N (3s)-9-(2,6-diaminopyrimidin-4-yl)-3-quinolin-3-ylnonanoic acid Chemical compound NC1=NC(N)=CC(CCCCCC[C@@H](CC(O)=O)C=2C=C3C=CC=CC3=NC=2)=N1 VEJIHHNAPVFTIX-HNNXBMFYSA-N 0.000 description 2
- FPLIORKDZLLQPL-HNNXBMFYSA-N (3s)-9-[2-amino-6-(ethylamino)pyrimidin-4-yl]-3-(2-ethoxypyrimidin-5-yl)nonanoic acid Chemical compound NC1=NC(NCC)=CC(CCCCCC[C@@H](CC(O)=O)C=2C=NC(OCC)=NC=2)=N1 FPLIORKDZLLQPL-HNNXBMFYSA-N 0.000 description 2
- WLGGRYVUWIAQNO-KRWDZBQOSA-N (3s)-9-[6-(ethylamino)pyridin-2-yl]-3-(2-methylpyrimidin-5-yl)nonanoic acid Chemical compound CCNC1=CC=CC(CCCCCC[C@@H](CC(O)=O)C=2C=NC(C)=NC=2)=N1 WLGGRYVUWIAQNO-KRWDZBQOSA-N 0.000 description 2
- AJRXGUGHNUPKPA-INIZCTEOSA-N (3s)-9-[6-(methylamino)pyridin-2-yl]-3-(2-methylpyrimidin-5-yl)nonanoic acid Chemical compound CNC1=CC=CC(CCCCCC[C@@H](CC(O)=O)C=2C=NC(C)=NC=2)=N1 AJRXGUGHNUPKPA-INIZCTEOSA-N 0.000 description 2
- XAUMHHQRAGTYON-HNNXBMFYSA-N (3s)-9-[6-(methylamino)pyridin-2-yl]-3-pyrimidin-5-ylnonanoic acid Chemical compound CNC1=CC=CC(CCCCCC[C@@H](CC(O)=O)C=2C=NC=NC=2)=N1 XAUMHHQRAGTYON-HNNXBMFYSA-N 0.000 description 2
- PWXAAPNZAANJNH-KRWDZBQOSA-N (3s)-9-[6-(methylamino)pyridin-2-yl]-3-quinoxalin-2-ylnonanoic acid Chemical compound CNC1=CC=CC(CCCCCC[C@@H](CC(O)=O)C=2N=C3C=CC=CC3=NC=2)=N1 PWXAAPNZAANJNH-KRWDZBQOSA-N 0.000 description 2
- IYVLNCGDRIBSON-KRWDZBQOSA-N (3s)-9-[6-amino-2-(ethylamino)pyrimidin-4-yl]-3-(2,3-dihydro-1-benzofuran-6-yl)nonanoic acid Chemical compound CCNC1=NC(N)=CC(CCCCCC[C@@H](CC(O)=O)C=2C=C3OCCC3=CC=2)=N1 IYVLNCGDRIBSON-KRWDZBQOSA-N 0.000 description 2
- PUAXFUCQWQYYSP-AWEZNQCLSA-N (3s)-9-[6-amino-2-(ethylamino)pyrimidin-4-yl]-3-(2-methoxypyrimidin-5-yl)nonanoic acid Chemical compound CCNC1=NC(N)=CC(CCCCCC[C@@H](CC(O)=O)C=2C=NC(OC)=NC=2)=N1 PUAXFUCQWQYYSP-AWEZNQCLSA-N 0.000 description 2
- JHVZPGUNRYRABX-HNNXBMFYSA-N (3s)-9-[6-amino-2-(ethylamino)pyrimidin-4-yl]-3-(2-methylpyrimidin-5-yl)nonanoic acid Chemical compound CCNC1=NC(N)=CC(CCCCCC[C@@H](CC(O)=O)C=2C=NC(C)=NC=2)=N1 JHVZPGUNRYRABX-HNNXBMFYSA-N 0.000 description 2
- APUMQXXPOIAIJC-HNNXBMFYSA-N (3s)-9-[6-amino-2-(ethylamino)pyrimidin-4-yl]-3-(6-methoxypyridin-3-yl)nonanoic acid Chemical compound CCNC1=NC(N)=CC(CCCCCC[C@@H](CC(O)=O)C=2C=NC(OC)=CC=2)=N1 APUMQXXPOIAIJC-HNNXBMFYSA-N 0.000 description 2
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 description 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 2
- 229940121819 ATPase inhibitor Drugs 0.000 description 2
- 208000006386 Bone Resorption Diseases 0.000 description 2
- 102000004171 Cathepsin K Human genes 0.000 description 2
- 108090000625 Cathepsin K Proteins 0.000 description 2
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 2
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000362 adenosine triphosphatase inhibitor Substances 0.000 description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 230000024279 bone resorption Effects 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 239000002834 estrogen receptor modulator Substances 0.000 description 2
- 239000003102 growth factor Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 210000002997 osteoclast Anatomy 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000849 selective androgen receptor modulator Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- FPLIORKDZLLQPL-OAHLLOKOSA-N (3r)-9-[2-amino-6-(ethylamino)pyrimidin-4-yl]-3-(2-ethoxypyrimidin-5-yl)nonanoic acid Chemical compound NC1=NC(NCC)=CC(CCCCCC[C@H](CC(O)=O)C=2C=NC(OCC)=NC=2)=N1 FPLIORKDZLLQPL-OAHLLOKOSA-N 0.000 description 1
- GIWIXAZUOFJHSH-FQEVSTJZSA-N (3s)-3-[5-(3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-6-yl)pentanoylamino]-3-quinolin-3-ylpropanoic acid Chemical compound C1=CC=CC2=CC([C@@H](NC(=O)CCCCC=3N=C4NCCOC4=CC=3)CC(=O)O)=CN=C21 GIWIXAZUOFJHSH-FQEVSTJZSA-N 0.000 description 1
- NDKSDRWJWLNIIF-KRWDZBQOSA-N (3s)-9-(2,3-dihydro-1h-pyrrolo[2,3-b]pyridin-6-yl)-3-(2-methylpyrimidin-5-yl)nonanoic acid Chemical compound C1=NC(C)=NC=C1[C@H](CC(O)=O)CCCCCCC1=CC=C(CCN2)C2=N1 NDKSDRWJWLNIIF-KRWDZBQOSA-N 0.000 description 1
- GMBMWLGJYVBWPA-HNNXBMFYSA-N (3s)-9-[6-amino-2-(ethylamino)pyrimidin-4-yl]-3-(2-ethoxypyrimidin-5-yl)nonanoic acid Chemical compound CCNC1=NC(N)=CC(CCCCCC[C@@H](CC(O)=O)C=2C=NC(OCC)=NC=2)=N1 GMBMWLGJYVBWPA-HNNXBMFYSA-N 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 description 1
- AWYWMTHHAQWPBM-UHFFFAOYSA-N 2-(2-methylpyrimidin-5-yl)-10-oxo-10-(1,4,5,6-tetrahydropyrimidin-2-ylamino)decanoic acid Chemical compound C1=NC(C)=NC=C1C(C(O)=O)CCCCCCCC(=O)NC1=NCCCN1 AWYWMTHHAQWPBM-UHFFFAOYSA-N 0.000 description 1
- IWFKOKATFORZPN-UHFFFAOYSA-N 2-[5-(2,6-diaminopyrimidin-4-yl)pentanoyl-methylamino]-3-(6-methoxypyridin-3-yl)propanoic acid Chemical compound C1=NC(OC)=CC=C1CC(C(O)=O)N(C)C(=O)CCCCC1=CC(N)=NC(N)=N1 IWFKOKATFORZPN-UHFFFAOYSA-N 0.000 description 1
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| PCT/US2001/001953 WO2001053262A1 (en) | 2000-01-24 | 2001-01-19 | Alpha v integrin receptor antagonists |
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| CA (1) | CA2397665A1 (https=) |
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| US6048861A (en) * | 1997-12-17 | 2000-04-11 | Merck & Co., Inc. | Integrin receptor antagonists |
| JP2004510766A (ja) * | 2000-10-05 | 2004-04-08 | メルク エンド カムパニー インコーポレーテッド | インテグリン受容体アンタゴニスト中間体を調製するための方法 |
| US20040030134A1 (en) * | 2001-10-01 | 2004-02-12 | Mcwilliams James Christopher | Process for preparation of integrin receptor antagonist intermediates |
| EP1457205A4 (en) | 2001-11-30 | 2006-07-05 | Santen Pharmaceutical Co Ltd | INHIBITOR OF ANGIOGENESIS |
| CA2478317A1 (en) * | 2002-03-04 | 2003-09-18 | Medimmune, Inc. | Methods of preventing or treating disorders by administering an integrin .alpha.v.beta.3 antagonist in combination with an hmg-coa reductase inhibitor or a bisphosphonate |
| WO2003075957A1 (en) * | 2002-03-04 | 2003-09-18 | Medimmune, Inc. | The prevention or treatment of cancer using integrin alphavbeta3 antagonists in combination with other agents |
| US7285268B2 (en) | 2002-11-26 | 2007-10-23 | Pdl Biopharma, Inc. | Chimeric and humanized antibodies to α5β1 integrin that modulate angiogenesis |
| US7276589B2 (en) | 2002-11-26 | 2007-10-02 | Pdl Biopharma, Inc. | Chimeric and humanized antibodies to α5β1 integrin that modulate angiogenesis |
| WO2004066956A2 (en) * | 2003-01-30 | 2004-08-12 | Medimmune, Inc. | Uses of integrin alphavbeta3 antagonists |
| DK1755659T3 (da) | 2004-03-24 | 2012-02-27 | Abbott Biotherapeutics Corp | Anvendelse af anti-alfa5beta1-antistoffer til inhibering af kræftcelleproliferation |
| AU2005229015C1 (en) * | 2004-04-02 | 2013-01-17 | The Regents Of The University Of California | Methods and compositions for treating and preventing disease associated with alphaVbeta5 integrin |
| EP2222636B1 (en) | 2007-12-21 | 2013-04-10 | Ligand Pharmaceuticals Inc. | Selective androgen receptor modulators (sarms) and uses thereof |
| US20110172217A1 (en) | 2008-09-05 | 2011-07-14 | Shionogi & Co., Ltd. | Ring-fused morpholine derivative having pi3k-inhibiting activity |
| EP2456460A4 (en) | 2009-07-24 | 2013-02-20 | Univ California | METHOD AND COMPOSITIONS FOR TREATING AND PREVENTING DISEASES ASSOCIATED WITH AVB5 INTEGRIN |
| CN105164107B (zh) * | 2012-12-20 | 2017-12-05 | 卢庆彬 | 用于与放射结合使用的放射增敏剂化合物 |
| US8901144B2 (en) * | 2013-02-07 | 2014-12-02 | Scifluor Life Sciences, Llc | Fluorinated 3-(2-oxo-3-(3-arylpropyl)imidazolidin-1-yl)-3-arylpropanoic acid derivatives |
| PT2953948T (pt) | 2013-02-07 | 2017-12-12 | Scifluor Life Sciences Inc | Antagonistas de integrina fluorada |
| SI3050878T1 (sl) | 2013-09-24 | 2022-01-31 | Fujifilm Corporation | Nova dušik-vsebujoča spojina ali njena sol ali kovinski kompleks le-te |
| US10898924B2 (en) * | 2014-07-16 | 2021-01-26 | Koninklijke Philips N.V. | Tiled CMUT dies with pitch uniformity |
| US10913736B2 (en) | 2014-08-22 | 2021-02-09 | University Of Washington | Specific inhibitors of methionyl-tRNA synthetase |
| US9790222B2 (en) | 2015-02-19 | 2017-10-17 | Scifluor Life Sciences, Inc. | Fluorinated tetrahydronaphthyridinyl nonanoic acid derivatives and uses thereof |
| BR112017020484B1 (pt) | 2015-03-25 | 2023-03-28 | Fujifilm Corporation | Métodos para fabricar um composto contendo nitrogênio ou sal do mesmo e um complexo metálico, compostos contendo nitrogênio, complexos dos ditos compostos e composições farmacêuticas compreendendo os ditos complexos |
| US10287259B2 (en) | 2016-03-14 | 2019-05-14 | The Penn State Research Foundation | Selenazolidine and thiazolidine compounds for treating cancer and other diseases |
| US10118929B2 (en) * | 2016-04-27 | 2018-11-06 | Scifluor Life Sciences, Inc. | Nonanoic and decanoic acid derivatives and uses thereof |
| MX2019001918A (es) | 2016-08-15 | 2019-09-06 | Bayer Cropscience Ag | Derivados del heterociclo biciclico condensado como agentes de control de plagas. |
| MA52117A (fr) | 2017-02-28 | 2022-04-06 | Morphic Therapeutic Inc | Inhibiteurs de l'intégrine (alpha-v) (bêta-6) |
| MX394210B (es) | 2017-02-28 | 2025-03-04 | Morphic Therapeutic Inc | INHIBIDORES DE INTEGRINA AVß6. |
| WO2020047208A1 (en) | 2018-08-29 | 2020-03-05 | Morphic Therapeutic, Inc. | Inhibitors of (alpha-v)(beta-6) integrin |
| WO2020047239A1 (en) | 2018-08-29 | 2020-03-05 | Morphic Therapeutic, Inc. | INHIBITING αV β6 INTEGRIN |
| SI3844162T1 (sl) | 2018-08-29 | 2025-06-30 | Morphic Therapeutic, Inc. | Zaviralci integrina alfa v beta6 |
| WO2020214834A1 (en) | 2019-04-19 | 2020-10-22 | Ligand Pharmaceuticals Inc. | Crystalline forms and methods of producing crystalline forms of a compound |
| WO2024137442A1 (en) | 2022-12-21 | 2024-06-27 | Gilead Sciences, Inc. | Combination therapy for treating cancer |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5652363A (en) * | 1995-10-05 | 1997-07-29 | C.D. Searle & Co. | Pyrido-1,4-oxazinylalkyl-benzamide derivatives |
| US5952341A (en) | 1996-10-30 | 1999-09-14 | Merck & Co., Inc. | Integrin antagonists |
| US5872122A (en) * | 1997-10-16 | 1999-02-16 | Monsanto Company | Pyrimidinylamidino β-amino acid derivatives useful as inhibitors of platelet aggregation |
| 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 |
| CN1589145A (zh) | 1999-06-02 | 2005-03-02 | 麦克公司 | αv整联蛋白受体拮抗剂 |
| US7015216B2 (en) * | 2000-07-21 | 2006-03-21 | Elan Pharmaceuticals, Inc. | Heteroaryl-β-alanine derivatives as alpha 4 integrin inhibitors |
-
2001
- 2001-01-19 CA CA002397665A patent/CA2397665A1/en not_active Abandoned
- 2001-01-19 AU AU36488/01A patent/AU780988B2/en not_active Ceased
- 2001-01-19 EP EP01908643A patent/EP1254116A4/en not_active Withdrawn
- 2001-01-19 JP JP2001553266A patent/JP2003520271A/ja not_active Withdrawn
- 2001-01-19 WO PCT/US2001/001953 patent/WO2001053262A1/en not_active Ceased
- 2001-01-23 US US09/767,471 patent/US6693101B2/en not_active Expired - Fee Related
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2003
- 2003-07-10 US US10/618,414 patent/US7153862B2/en not_active Expired - Fee Related
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