JP2003520271A5 - - Google Patents
Download PDFInfo
- Publication number
- 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- Withdrawn
Links
- 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
- XLQVCNQOYAVZTQ-UHFFFAOYSA-N 2-[5-(3-amino-5,6,7,8-tetrahydroisoquinolin-1-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=NC(N)=CC2=C1CCCC2 XLQVCNQOYAVZTQ-UHFFFAOYSA-N 0.000 description 1
- UEAARPQIXXQIAV-UHFFFAOYSA-N 3-(2-ethoxypyrimidin-5-yl)-9-[2-(ethylamino)pyrimidin-4-yl]nonanoic acid Chemical compound CCNC1=NC=CC(CCCCCCC(CC(O)=O)C=2C=NC(OCC)=NC=2)=N1 UEAARPQIXXQIAV-UHFFFAOYSA-N 0.000 description 1
- UIPWNMDREFCECM-UHFFFAOYSA-N 3-(2-ethoxypyrimidin-5-yl)-9-[6-(ethylamino)pyridin-2-yl]nonanoic acid Chemical compound CCNC1=CC=CC(CCCCCCC(CC(O)=O)C=2C=NC(OCC)=NC=2)=N1 UIPWNMDREFCECM-UHFFFAOYSA-N 0.000 description 1
- GJVHCRVNERTQGJ-UHFFFAOYSA-N 3-(2-ethoxypyrimidin-5-yl)-9-[6-(methylamino)pyridin-2-yl]nonanoic acid Chemical compound C1=NC(OCC)=NC=C1C(CC(O)=O)CCCCCCC1=CC=CC(NC)=N1 GJVHCRVNERTQGJ-UHFFFAOYSA-N 0.000 description 1
- LHLSZKTUKMWFQV-UHFFFAOYSA-N 3-(2-methoxypyrimidin-5-yl)-9-[6-(methylamino)pyridin-2-yl]nonanoic acid Chemical compound CNC1=CC=CC(CCCCCCC(CC(O)=O)C=2C=NC(OC)=NC=2)=N1 LHLSZKTUKMWFQV-UHFFFAOYSA-N 0.000 description 1
- AFRWBHKDHBGCJZ-UHFFFAOYSA-N 3-(2-methylpyrimidin-5-yl)-10-(1,4,5,6-tetrahydropyrimidin-2-ylamino)decanoic acid Chemical compound C1=NC(C)=NC=C1C(CC(O)=O)CCCCCCCNC1=NCCCN1 AFRWBHKDHBGCJZ-UHFFFAOYSA-N 0.000 description 1
- GIWIXAZUOFJHSH-UHFFFAOYSA-N 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(NC(=O)CCCCC=3N=C4NCCOC4=CC=3)CC(=O)O)=CN=C21 GIWIXAZUOFJHSH-UHFFFAOYSA-N 0.000 description 1
- LUTBCWPINXUOLG-UHFFFAOYSA-N 3-pyrimidin-5-yl-9-(6,7,8,9-tetrahydro-5h-pyrido[2,3-b]azepin-2-yl)nonanoic acid Chemical compound C=1C=C2CCCCNC2=NC=1CCCCCCC(CC(=O)O)C1=CN=CN=C1 LUTBCWPINXUOLG-UHFFFAOYSA-N 0.000 description 1
- RYBXVUBVKWLRLI-UHFFFAOYSA-N 3-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(NC(=O)CCCCC=3N=C4NCCNC4=CC=3)CC(=O)O)=CN=C21 RYBXVUBVKWLRLI-UHFFFAOYSA-N 0.000 description 1
- NDKSDRWJWLNIIF-UHFFFAOYSA-N 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=C1C(CC(O)=O)CCCCCCC1=CC=C(CCN2)C2=N1 NDKSDRWJWLNIIF-UHFFFAOYSA-N 0.000 description 1
- GYQWSGPGWQIRDK-UHFFFAOYSA-N 9-(2,6-diaminopyrimidin-4-yl)-3-(2-methylpyrimidin-5-yl)nonanoic acid Chemical compound C1=NC(C)=NC=C1C(CC(O)=O)CCCCCCC1=CC(N)=NC(N)=N1 GYQWSGPGWQIRDK-UHFFFAOYSA-N 0.000 description 1
- VEJIHHNAPVFTIX-UHFFFAOYSA-N 9-(2,6-diaminopyrimidin-4-yl)-3-quinolin-3-ylnonanoic acid Chemical compound NC1=NC(N)=CC(CCCCCCC(CC(O)=O)C=2C=C3C=CC=CC3=NC=2)=N1 VEJIHHNAPVFTIX-UHFFFAOYSA-N 0.000 description 1
- FPLIORKDZLLQPL-UHFFFAOYSA-N 9-[2-amino-6-(ethylamino)pyrimidin-4-yl]-3-(2-ethoxypyrimidin-5-yl)nonanoic acid Chemical compound NC1=NC(NCC)=CC(CCCCCCC(CC(O)=O)C=2C=NC(OCC)=NC=2)=N1 FPLIORKDZLLQPL-UHFFFAOYSA-N 0.000 description 1
- SKQDZNOTIPXFTR-UHFFFAOYSA-N 9-[6-(ethylamino)pyridin-2-yl]-3-(2-methoxypyrimidin-5-yl)nonanoic acid Chemical compound CCNC1=CC=CC(CCCCCCC(CC(O)=O)C=2C=NC(OC)=NC=2)=N1 SKQDZNOTIPXFTR-UHFFFAOYSA-N 0.000 description 1
- AJRXGUGHNUPKPA-UHFFFAOYSA-N 9-[6-(methylamino)pyridin-2-yl]-3-(2-methylpyrimidin-5-yl)nonanoic acid Chemical compound CNC1=CC=CC(CCCCCCC(CC(O)=O)C=2C=NC(C)=NC=2)=N1 AJRXGUGHNUPKPA-UHFFFAOYSA-N 0.000 description 1
- XAUMHHQRAGTYON-UHFFFAOYSA-N 9-[6-(methylamino)pyridin-2-yl]-3-pyrimidin-5-ylnonanoic acid Chemical compound CNC1=CC=CC(CCCCCCC(CC(O)=O)C=2C=NC=NC=2)=N1 XAUMHHQRAGTYON-UHFFFAOYSA-N 0.000 description 1
- PWXAAPNZAANJNH-UHFFFAOYSA-N 9-[6-(methylamino)pyridin-2-yl]-3-quinoxalin-2-ylnonanoic acid Chemical compound CNC1=CC=CC(CCCCCCC(CC(O)=O)C=2N=C3C=CC=CC3=NC=2)=N1 PWXAAPNZAANJNH-UHFFFAOYSA-N 0.000 description 1
- IYVLNCGDRIBSON-UHFFFAOYSA-N 9-[6-amino-2-(ethylamino)pyrimidin-4-yl]-3-(2,3-dihydro-1-benzofuran-6-yl)nonanoic acid Chemical compound CCNC1=NC(N)=CC(CCCCCCC(CC(O)=O)C=2C=C3OCCC3=CC=2)=N1 IYVLNCGDRIBSON-UHFFFAOYSA-N 0.000 description 1
- GMBMWLGJYVBWPA-UHFFFAOYSA-N 9-[6-amino-2-(ethylamino)pyrimidin-4-yl]-3-(2-ethoxypyrimidin-5-yl)nonanoic acid Chemical compound CCNC1=NC(N)=CC(CCCCCCC(CC(O)=O)C=2C=NC(OCC)=NC=2)=N1 GMBMWLGJYVBWPA-UHFFFAOYSA-N 0.000 description 1
- PUAXFUCQWQYYSP-UHFFFAOYSA-N 9-[6-amino-2-(ethylamino)pyrimidin-4-yl]-3-(2-methoxypyrimidin-5-yl)nonanoic acid Chemical compound CCNC1=NC(N)=CC(CCCCCCC(CC(O)=O)C=2C=NC(OC)=NC=2)=N1 PUAXFUCQWQYYSP-UHFFFAOYSA-N 0.000 description 1
- JHVZPGUNRYRABX-UHFFFAOYSA-N 9-[6-amino-2-(ethylamino)pyrimidin-4-yl]-3-(2-methylpyrimidin-5-yl)nonanoic acid Chemical compound CCNC1=NC(N)=CC(CCCCCCC(CC(O)=O)C=2C=NC(C)=NC=2)=N1 JHVZPGUNRYRABX-UHFFFAOYSA-N 0.000 description 1
- APUMQXXPOIAIJC-UHFFFAOYSA-N 9-[6-amino-2-(ethylamino)pyrimidin-4-yl]-3-(6-methoxypyridin-3-yl)nonanoic acid Chemical compound CCNC1=NC(N)=CC(CCCCCCC(CC(O)=O)C=2C=NC(OC)=CC=2)=N1 APUMQXXPOIAIJC-UHFFFAOYSA-N 0.000 description 1
- HDXFHKBRTKWMDO-UHFFFAOYSA-N 9-[6-amino-2-(ethylamino)pyrimidin-4-yl]-3-quinoxalin-2-ylnonanoic acid Chemical compound CCNC1=NC(N)=CC(CCCCCCC(CC(O)=O)C=2N=C3C=CC=CC3=NC=2)=N1 HDXFHKBRTKWMDO-UHFFFAOYSA-N 0.000 description 1
- 102100033367 Appetite-regulating hormone Human genes 0.000 description 1
- 101710111255 Appetite-regulating hormone Proteins 0.000 description 1
- MMALNTHAZKZONC-ZDUSSCGKSA-N CCCCCCC[C@@H](C1=CN=C(N=C1)OCC)C(=O)O Chemical compound CCCCCCC[C@@H](C1=CN=C(N=C1)OCC)C(=O)O MMALNTHAZKZONC-ZDUSSCGKSA-N 0.000 description 1
- 101100381481 Caenorhabditis elegans baz-2 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 101100481404 Danio rerio tie1 gene Proteins 0.000 description 1
- 101100481408 Danio rerio tie2 gene Proteins 0.000 description 1
- 108010009202 Growth Factor Receptors Proteins 0.000 description 1
- 102000009465 Growth Factor Receptors Human genes 0.000 description 1
- 101710170181 Metalloproteinase inhibitor Proteins 0.000 description 1
- 101100481410 Mus musculus Tek gene Proteins 0.000 description 1
- 101100481406 Mus musculus Tie1 gene Proteins 0.000 description 1
- STTGAPXAISJGRL-UJONTBEJSA-N NC1(NC(=CC=N1)CCCCCC[C@H](CC(=O)O)C=1C=NC(=NC1)OCC)NCC Chemical compound NC1(NC(=CC=N1)CCCCCC[C@H](CC(=O)O)C=1C=NC(=NC1)OCC)NCC STTGAPXAISJGRL-UJONTBEJSA-N 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 101100372762 Rattus norvegicus Flt1 gene Proteins 0.000 description 1
- 102000003990 Urokinase-type plasminogen activator Human genes 0.000 description 1
- 108090000435 Urokinase-type plasminogen activator Proteins 0.000 description 1
- 102000016549 Vascular Endothelial Growth Factor Receptor-2 Human genes 0.000 description 1
- 101100445392 Xenopus laevis ephb3 gene Proteins 0.000 description 1
- DCSBSVSZJRSITC-UHFFFAOYSA-M alendronate sodium trihydrate Chemical compound O.O.O.[Na+].NCCCC(O)(P(O)(O)=O)P(O)([O-])=O DCSBSVSZJRSITC-UHFFFAOYSA-M 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 239000002254 cytotoxic agent Substances 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000004030 farnesyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 108020001507 fusion proteins Proteins 0.000 description 1
- 102000037865 fusion proteins Human genes 0.000 description 1
- 239000003324 growth hormone secretagogue Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229940126170 metalloproteinase inhibitor Drugs 0.000 description 1
- 239000003475 metalloproteinase inhibitor Substances 0.000 description 1
- 230000030991 negative regulation of bone resorption Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000003528 protein farnesyltransferase inhibitor Substances 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 239000002525 vasculotropin inhibitor Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17779200P | 2000-01-24 | 2000-01-24 | |
| US60/177,792 | 2000-01-24 | ||
| US23046900P | 2000-09-06 | 2000-09-06 | |
| US60/230,469 | 2000-09-06 | ||
| PCT/US2001/001953 WO2001053262A1 (en) | 2000-01-24 | 2001-01-19 | Alpha v integrin receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003520271A JP2003520271A (ja) | 2003-07-02 |
| JP2003520271A5 true JP2003520271A5 (enExample) | 2008-03-21 |
Family
ID=26873652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001553266A Withdrawn JP2003520271A (ja) | 2000-01-24 | 2001-01-19 | αｖインテグリン受容体拮抗薬 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US6693101B2 (enExample) |
| EP (1) | EP1254116A4 (enExample) |
| JP (1) | JP2003520271A (enExample) |
| AU (1) | AU780988B2 (enExample) |
| CA (1) | CA2397665A1 (enExample) |
| WO (1) | WO2001053262A1 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| AU2002349621A1 (en) * | 2001-11-30 | 2003-06-10 | Santen Pharmaceutical Co., Ltd. | Angiogenesis inhibitor |
| CA2478239A1 (en) * | 2002-03-04 | 2003-09-18 | Medimmune, Inc. | The prevention or treatment of cancer using integrin alphavbeta3 antagonists in combination with other agents |
| 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 |
| 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 |
| BRPI0509177A (pt) | 2004-03-24 | 2007-09-18 | Pdl Biopharma Inc | uso de anticorpos anti-alfa5beta1 para inibir a proliferação de células cancerìgenas |
| HRP20130782T1 (en) * | 2004-04-02 | 2013-09-30 | The Regents Of The University Of California, Office Of Technology Transfer | Methods and compositions for treating and preventing disease associated with alpha v beta 5 integrin |
| ES2413504T3 (es) | 2007-12-21 | 2013-07-16 | Ligand Pharmaceuticals Inc. | Moduladores selectivos del receptor de andrógeno (SARM) y usos de los mismos |
| WO2010027002A1 (ja) | 2008-09-05 | 2010-03-11 | 塩野義製薬株式会社 | Ｐｉ３ｋ阻害活性を有する縮環モルホリン誘導体 |
| EP2456460A4 (en) | 2009-07-24 | 2013-02-20 | Univ California | METHOD AND COMPOSITIONS FOR TREATING AND PREVENTING DISEASES ASSOCIATED WITH AVB5 INTEGRIN |
| MX2015008010A (es) * | 2012-12-20 | 2016-04-26 | qing-bin Lu | Compuestos radiosensabilizadores para usarse en combinacion con radiacion. |
| PT2953948T (pt) | 2013-02-07 | 2017-12-12 | Scifluor Life Sciences Inc | Antagonistas de integrina fluorada |
| 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 |
| FI3929196T3 (fi) * | 2013-09-24 | 2023-10-02 | Fujifilm Corp | Typpeä sisältävän yhdisteen tai sen suolan tai niiden metallikompleksin farmaseuttinen koostumus |
| EP3169449B1 (en) * | 2014-07-16 | 2018-03-21 | 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 |
| CA2976634C (en) | 2015-02-19 | 2023-10-17 | Scifluor Life Sciences, Inc | Fluorinated tetrahydronaphthyridinyl nonanoic acid derivatives and uses thereof |
| KR102029746B1 (ko) | 2015-03-25 | 2019-10-08 | 후지필름 가부시키가이샤 | 신규인 함질소 화합물 또는 그 염의 제조 방법 및 이들의 제조 중간체 |
| 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 |
| KR102419244B1 (ko) | 2016-08-15 | 2022-07-08 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 해충 방제제로서의 축합 바이시클릭 헤테로사이클 유도체 |
| CN116283977A (zh) | 2017-02-28 | 2023-06-23 | 莫菲克医疗股份有限公司 | αvβ6整合蛋白的抑制剂 |
| EP3589285A4 (en) | 2017-02-28 | 2020-08-12 | Morphic Therapeutic, Inc. | INHIBITORS OF INTEGRIN (ALPHA-V) (BETA-6) |
| SG11202101913PA (en) | 2018-08-29 | 2021-03-30 | Morphic Therapeutic Inc | INHIBITING aV ß6 INTEGRIN |
| BR112021020864A2 (pt) | 2019-04-19 | 2021-12-14 | Ligand Pharm Inc | Formas cristalinas e métodos de produção de formas cristalinas de um composto |
| EP4637731A1 (en) | 2022-12-21 | 2025-10-29 | 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 |
| HUP0100397A3 (en) * | 1997-12-17 | 2002-10-28 | Merck & Co Inc | Tetrahydro- or octahydrobenzonaphtyridin and quinolin derivatives, pharmaceutical compositions thereof and process for their preparation |
| US6048861A (en) * | 1997-12-17 | 2000-04-11 | Merck & Co., Inc. | Integrin receptor antagonists |
| AU749351B2 (en) | 1999-06-02 | 2002-06-27 | Merck & Co., Inc. | Alpha V integrin receptor antagonists |
| 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 WO PCT/US2001/001953 patent/WO2001053262A1/en not_active Ceased
- 2001-01-19 EP EP01908643A patent/EP1254116A4/en not_active Withdrawn
- 2001-01-19 AU AU36488/01A patent/AU780988B2/en not_active Ceased
- 2001-01-19 JP JP2001553266A patent/JP2003520271A/ja not_active Withdrawn
- 2001-01-23 US US09/767,471 patent/US6693101B2/en not_active Expired - Fee Related
-
2003
- 2003-07-10 US US10/618,414 patent/US7153862B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2003520271A5 (enExample) | ||
| JP2004500326A5 (enExample) | ||
| CA2397194A1 (en) | Alpha v integrin receptor antagonists | |
| ES2694513T3 (es) | Derivado de quinolina | |
| JP7380507B2 (ja) | Ｓｔｉｎｇ作動化合物 | |
| TWI848901B (zh) | Shp2磷酸酶抑制劑及其使用方法 | |
| JP2020504739A (ja) | Ｐｄ−ｌ１内在化誘導物質としてのテトラヒドロイミダゾ［４，５−ｃ］ピリジン誘導体 | |
| RU2013127577A (ru) | Замещенные 4-селенофен-2(или 3)-иламино)пиримидиновые соединения и способы их применения | |
| TW201822764A (zh) | Syk抑制劑 | |
| ES2710190T3 (es) | Derivados de 4-azaindol | |
| US20210128723A1 (en) | Combination of atr kinase inhibitors and pd-1/pd-l1 inhibitors | |
| JP2020524717A (ja) | ヒトｓｔｉｎｇの小分子調節因子 | |
| WO2022265993A1 (en) | Urea derivatives which can be used to treat cancer | |
| RU2018134981A (ru) | Конъюгаты, содержащие ингибиторы RIPK2 | |
| JP2018515570A (ja) | Ｂｒａｆ−ｖ６００関連疾患の治療に使用するためのｐｌｘ−８３９４またはｐｌｘ−７９０４ | |
| JP2002508326A5 (enExample) | ||
| CA2859604A1 (en) | Compounds | |
| JP2021130702A (ja) | 治療用複素環式化合物 | |
| JP2017520607A5 (enExample) | ||
| JP2010512338A5 (enExample) | ||
| KR20150118102A (ko) | Pi3 키나제 모듈레이터로서의 헤테로방향족 화합물 | |
| KR20150083833A (ko) | Pi3 키나제 모듈레이터로서의 헤테로방향족 화합물 및 이의 이용 방법 | |
| AR065531A1 (es) | Derivados de pirimidina, procesos de obtencion y composiciones farmaceuticas. | |
| MY194730A (en) | Liposomal Formulation for use in the Treatment of Cancer | |
| JP2017530154A5 (enExample) |