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- Withdrawn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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| US6048861A (en) * | 1997-12-17 | 2000-04-11 | Merck & Co., Inc. | Integrin receptor antagonists |
| AU2001296950A1 (en) * | 2000-10-05 | 2002-04-15 | Merck & Co., Inc. | Process for preparation of integrin receptor antagonist intermediates |
| 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 |
| JP2005533001A (ja) * | 2002-03-04 | 2005-11-04 | メディミューン，インコーポレーテッド | インテグリンαｖβ３アンタゴニストを他の物質と併用投与する癌の予防または治療方法 |
| US7276589B2 (en) | 2002-11-26 | 2007-10-02 | Pdl Biopharma, Inc. | Chimeric and humanized antibodies to α5β1 integrin that modulate angiogenesis |
| US7285268B2 (en) | 2002-11-26 | 2007-10-23 | Pdl Biopharma, Inc. | Chimeric and humanized antibodies to α5β1 integrin that modulate angiogenesis |
| EP1596884A2 (en) * | 2003-01-30 | 2005-11-23 | Medimmune, Inc. | Uses of integrin alphavbeta3 antagonists |
| ATE531388T1 (de) | 2004-03-24 | 2011-11-15 | Abbott Biotherapeutics Corp | Verwendung von anti-alpha5beta1-antikörpern zur hemmung der krebszellproliferation |
| EP1734996B1 (en) | 2004-04-02 | 2013-05-22 | The Regents of The University of California | Methods and compositions for treating and preventing disease associated with alpha v beta 5 integrin |
| CN101945853B (zh) | 2007-12-21 | 2014-08-20 | 配体药物公司 | 选择性雄激素受体调节剂(sarm)及其应用 |
| EP2341052A4 (en) | 2008-09-05 | 2011-10-12 | Shionogi & Co | RING-CONDENSED MORPHOLINE DERIVATIVITY WITH PI3K-INHIBITING EFFECT |
| JP5755647B2 (ja) | 2009-07-24 | 2015-07-29 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | αｖβ５インテグリンに関連する疾患の処置および予防のための方法および組成物 |
| MX2015008010A (es) * | 2012-12-20 | 2016-04-26 | qing-bin Lu | Compuestos radiosensabilizadores para usarse en combinacion con radiacion. |
| 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 |
| EP3266782B1 (en) | 2013-02-07 | 2019-10-30 | SciFluor Life Sciences, Inc. | Fluorinated integrin antagonists |
| DK3929196T3 (da) * | 2013-09-24 | 2023-09-25 | Fujifilm Corp | Farmaceutisk sammensætning af en nitrogenholdig forbindelse eller salt deraf, eller metalkompleks deraf |
| JP6357275B2 (ja) * | 2014-07-16 | 2018-07-11 | コーニンクレッカ フィリップス エヌ ヴェＫｏｎｉｎｋｌｉｊｋｅ Ｐｈｉｌｉｐｓ Ｎ．Ｖ． | ピッチ均一性を有したタイル状ｃｍｕｔダイ |
| US10913736B2 (en) | 2014-08-22 | 2021-02-09 | University Of Washington | Specific inhibitors of methionyl-tRNA synthetase |
| EP3925959A1 (en) | 2015-02-19 | 2021-12-22 | OcuTerra Therapeutics, Inc. | Fluorinated derivatives of 3-(2-oxo-3-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl)imidazolidin-1-yl)propanoic acid and uses thereof |
| LT3275883T (lt) * | 2015-03-25 | 2021-08-25 | Fujifilm Corporation | Naujo azotą turinčio junginio arba jo druskos gamybos būdas ir jo tarpinio junginio gamyba |
| 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 |
| AU2017314083B2 (en) | 2016-08-15 | 2020-12-10 | Bayer Aktiengesellschaft | Condensed bicyclic heterocycle derivatives as pest control agents |
| EP4159727B1 (en) | 2017-02-28 | 2026-04-08 | Morphic Therapeutic, Inc. | Inhibitors of (alpha-v)(beta-6) integrin |
| US11046685B2 (en) | 2017-02-28 | 2021-06-29 | Morphic Therapeutic, Inc. | Inhibitors of (α-v)(β-6) integrin |
| PT3844162T (pt) | 2018-08-29 | 2025-03-28 | Morphic Therapeutic Inc | Inibidores da integrina alfa v beta6 |
| AU2019327475B2 (en) | 2018-08-29 | 2025-06-05 | Morphic Therapeutic, Inc. | INHIBITING αV β6 INTEGRIN |
| WO2020047208A1 (en) | 2018-08-29 | 2020-03-05 | Morphic Therapeutic, Inc. | Inhibitors of (alpha-v)(beta-6) integrin |
| AU2020257397B2 (en) | 2019-04-19 | 2026-02-26 | 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)
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| 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 |
| SK9192000A3 (en) * | 1997-12-17 | 2001-03-12 | Merck & Co Inc | Integrin receptor antagonists |
| DE60035779T2 (de) | 1999-06-02 | 2008-04-30 | Merck & Co., Inc. | Alpha v integrin-rezeptor antagonisten |
| US7015216B2 (en) * | 2000-07-21 | 2006-03-21 | Elan Pharmaceuticals, Inc. | Heteroaryl-β-alanine derivatives as alpha 4 integrin inhibitors |
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2001
- 2001-01-19 JP JP2001553266A patent/JP2003520271A/ja not_active Withdrawn
- 2001-01-19 EP EP01908643A patent/EP1254116A4/en not_active Withdrawn
- 2001-01-19 WO PCT/US2001/001953 patent/WO2001053262A1/en not_active Ceased
- 2001-01-19 CA CA002397665A patent/CA2397665A1/en not_active Abandoned
- 2001-01-19 AU AU36488/01A patent/AU780988B2/en not_active Ceased
- 2001-01-23 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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