JP2006518333A - インテグリン受容体アンタゴニストとしてのヘテロアリールアルカン酸 - Google Patents

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Publication number

JP2006518333A

JP2006518333A JP2004563931A JP2004563931A JP2006518333A JP 2006518333 A JP2006518333 A JP 2006518333A JP 2004563931 A JP2004563931 A JP 2004563931A JP 2004563931 A JP2004563931 A JP 2004563931A JP 2006518333 A JP2006518333 A JP 2006518333A

Authority

JP

Japan

Prior art keywords

tetrahydro

propyl

naphthyridin

oxadiazol

butanoic acid

Prior art date

2002-12-20

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Withdrawn

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• 239000002253 acid Substances 0.000 title claims description 18
• 150000007513 acids Chemical class 0.000 title description 4
• 229940127449 Integrin Receptor Antagonists Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 166
• 238000000034 method Methods 0.000 claims abstract description 117
• 108010044426 integrins Proteins 0.000 claims abstract description 21
• 102000006495 integrins Human genes 0.000 claims abstract description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
• -1 TFA salt Chemical class 0.000 claims description 520
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 244
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 218
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 162
• 239000000203 mixture Substances 0.000 claims description 152
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 105
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 47
• 238000011282 treatment Methods 0.000 claims description 40
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 31
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 206010028980 Neoplasm Diseases 0.000 claims description 17
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 15
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 14
• 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 14
• 201000010099 disease Diseases 0.000 claims description 13
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 12
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 12
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 11
• 230000002265 prevention Effects 0.000 claims description 9
• CDXJNCAVPFGVNL-UHFFFAOYSA-N propyl 2,2,2-trifluoroacetate Chemical compound CCCOC(=O)C(F)(F)F CDXJNCAVPFGVNL-UHFFFAOYSA-N 0.000 claims description 9
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
• 206010027476 Metastases Diseases 0.000 claims description 8
• 230000033115 angiogenesis Effects 0.000 claims description 8
• 208000002780 macular degeneration Diseases 0.000 claims description 8
• 230000009401 metastasis Effects 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 208000001132 Osteoporosis Diseases 0.000 claims description 7
• 206010003246 arthritis Diseases 0.000 claims description 7
• 230000004614 tumor growth Effects 0.000 claims description 7
• XEHFCPCPAVJSSC-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,8-naphthyridine hydrochloride Chemical compound Cl.N1=CC=CC=2CCCNC12 XEHFCPCPAVJSSC-UHFFFAOYSA-N 0.000 claims description 6
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• CTHYLBXDQVAGEJ-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]-1h-pyrazol-5-yl]butanoic acid Chemical compound C1=C2OCOC2=CC(C(CC=2NN=C(OCCC=3N=C4NCCCC4=CC=3)C=2)CC(=O)O)=C1 CTHYLBXDQVAGEJ-UHFFFAOYSA-N 0.000 claims description 6
• RHLXEMRZXLKWFL-UHFFFAOYSA-N 3-[2-(4-chlorophenyl)-1,3-thiazol-5-yl]-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;hydrochloride Chemical compound Cl.N=1C(CCCC=2N=C3NCCCC3=CC=2)=NOC=1CC(CC(=O)O)C(S1)=CN=C1C1=CC=C(Cl)C=C1 RHLXEMRZXLKWFL-UHFFFAOYSA-N 0.000 claims description 6
• FASNCBYHMZWIQR-UHFFFAOYSA-N 3-[2-(4-fluorophenyl)-1,3-thiazol-5-yl]-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;hydrochloride Chemical compound Cl.N=1C(CCCC=2N=C3NCCCC3=CC=2)=NOC=1CC(CC(=O)O)C(S1)=CN=C1C1=CC=C(F)C=C1 FASNCBYHMZWIQR-UHFFFAOYSA-N 0.000 claims description 6
• 208000037803 restenosis Diseases 0.000 claims description 6
• YZUMUFXGTYAJSH-UHFFFAOYSA-N 3-(3-fluoro-5-methoxyphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;hydrochloride Chemical compound Cl.COC1=CC(F)=CC(C(CC(O)=O)CC=2ON=C(CCCC=3N=C4NCCCC4=CC=3)N=2)=C1 YZUMUFXGTYAJSH-UHFFFAOYSA-N 0.000 claims description 5
• 201000001320 Atherosclerosis Diseases 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 208000024891 symptom Diseases 0.000 claims description 5
• YGOKSIVHHLSPET-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]-1,2-oxazol-5-yl]butanoic acid Chemical compound C1=C2OCOC2=CC(C(CC=2ON=C(OCCC=3N=C4NCCCC4=CC=3)C=2)CC(=O)O)=C1 YGOKSIVHHLSPET-UHFFFAOYSA-N 0.000 claims description 4
• YRIJMZJTWNXHBY-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-[3-(1-methyl-3,4-dihydro-2h-pyrido[2,3-b]pyrazin-6-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound C1=C2OCOC2=CC(C(CC(O)=O)CC=2ON=C(N=2)CCCC=2N=C3NCCN(C3=CC=2)C)=C1 YRIJMZJTWNXHBY-UHFFFAOYSA-N 0.000 claims description 4
• GDIRJNSKARXDOU-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-[3-(5,5-dimethyl-7,8-dihydro-6h-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound C1=C2OCOC2=CC(C(CC(O)=O)CC=2ON=C(N=2)CCCC=2N=C3NCCC(C3=CC=2)(C)C)=C1 GDIRJNSKARXDOU-UHFFFAOYSA-N 0.000 claims description 4
• SUULYRBWJVOKAN-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-[3-[6-(methylamino)pyridin-2-yl]propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;hydrochloride Chemical compound Cl.CNC1=CC=CC(CCCC=2N=C(CC(CC(O)=O)C=3C=C4OCOC4=CC=3)ON=2)=N1 SUULYRBWJVOKAN-UHFFFAOYSA-N 0.000 claims description 4
• YLEXAKYOIPPMHL-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-[4-[(4-methylpyridin-2-yl)amino]butyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound CC1=CC=NC(NCCCCC=2N=C(CC(CC(O)=O)C=3C=C4OCOC4=CC=3)ON=2)=C1 YLEXAKYOIPPMHL-UHFFFAOYSA-N 0.000 claims description 4
• FZRXRMSHOXFYOR-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]tetrazol-2-yl]butanoic acid Chemical compound C1=C2OCOC2=CC(C(CN2N=C(CCCC=3N=C4NCCCC4=CC=3)N=N2)CC(=O)O)=C1 FZRXRMSHOXFYOR-UHFFFAOYSA-N 0.000 claims description 4
• QQGAEPAXDPVEAM-UHFFFAOYSA-N 3-(4-cyanophenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound N=1C(CCCC=2N=C3NCCCC3=CC=2)=NOC=1CC(CC(=O)O)C1=CC=C(C#N)C=C1 QQGAEPAXDPVEAM-UHFFFAOYSA-N 0.000 claims description 4
• HDXDSKJYKQCQEJ-UHFFFAOYSA-N 3-methyl-4-[6-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]pyridin-3-yl]butanoic acid Chemical compound N1=CC(CC(CC(O)=O)C)=CC=C1OCCC1=CC=C(CCCN2)C2=N1 HDXDSKJYKQCQEJ-UHFFFAOYSA-N 0.000 claims description 4
• 241000124008 Mammalia Species 0.000 claims description 4
• 230000003211 malignant effect Effects 0.000 claims description 4
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
• NNKYHRYBPQBUBA-UHFFFAOYSA-N 2-[1-[(2-methylpropan-2-yl)oxycarbonyl]-4-[[3-[4-(pyridin-2-ylamino)butyl]-1,2,4-oxadiazol-5-yl]methyl]piperidin-4-yl]acetic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CN(C(=O)OC(C)(C)C)CCC1(CC(O)=O)CC1=NC(CCCCNC=2N=CC=CC=2)=NO1 NNKYHRYBPQBUBA-UHFFFAOYSA-N 0.000 claims description 3
• LFGOVVXHZSOXIM-UHFFFAOYSA-N 2-[1-benzoyl-4-[[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]methyl]piperidin-4-yl]acetic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CC(CC(=O)O)(CC=2ON=C(CCCC=3N=C4NCCCC4=CC=3)N=2)CCN1C(=O)C1=CC=CC=C1 LFGOVVXHZSOXIM-UHFFFAOYSA-N 0.000 claims description 3
• JEODEZCDRAYGLQ-UHFFFAOYSA-N 2-[1-benzoyl-4-[[3-[4-(pyridin-2-ylamino)butyl]-1,2,4-oxadiazol-5-yl]methyl]piperidin-4-yl]acetic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CN(C(=O)C=2C=CC=CC=2)CCC1(CC(=O)O)CC(ON=1)=NC=1CCCCNC1=CC=CC=N1 JEODEZCDRAYGLQ-UHFFFAOYSA-N 0.000 claims description 3
• OKDFDEMTBGQHLA-UHFFFAOYSA-N 2-[2-[6-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]pyridin-3-yl]cyclopropyl]acetic acid Chemical compound OC(=O)CC1CC1C(C=N1)=CC=C1OCCC1=CC=C(CCCN2)C2=N1 OKDFDEMTBGQHLA-UHFFFAOYSA-N 0.000 claims description 3
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 3
• FDXPOIAKVYSLTR-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[2-[2-(3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-6-yl)ethyl]-3-oxo-1,2-oxazol-5-yl]butanoic acid Chemical compound C1=C2OCOC2=CC(C(CC=2ON(CCC=3N=C4NCCOC4=CC=3)C(=O)C=2)CC(=O)O)=C1 FDXPOIAKVYSLTR-UHFFFAOYSA-N 0.000 claims description 3
• POSBPWYIGMKFBR-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-[2-(1,2,3,5-tetrahydropyrido[2,3-e][1,4]oxazepin-8-yl)ethoxy]-1,2-oxazol-5-yl]butanoic acid Chemical compound C1OCCNC2=NC(CCOC=3C=C(ON=3)CC(CC(=O)O)C=3C=C4OCOC4=CC=3)=CC=C21 POSBPWYIGMKFBR-UHFFFAOYSA-N 0.000 claims description 3
• ZQAQMOMRTYIDJU-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-[2-(1-methyl-3,4-dihydro-2h-pyrido[2,3-b]pyrazin-6-yl)ethoxy]-1,2-oxazol-5-yl]butanoic acid Chemical compound C1=C2OCOC2=CC(C(CC(O)=O)CC2=CC(=NO2)OCCC=2N=C3NCCN(C3=CC=2)C)=C1 ZQAQMOMRTYIDJU-UHFFFAOYSA-N 0.000 claims description 3
• RSOBTNQLFLVQCQ-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-[2-(2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazepin-7-yl)ethoxy]-1,2-oxazol-5-yl]butanoic acid Chemical compound O1CCCNC2=NC(CCOC=3C=C(ON=3)CC(CC(=O)O)C=3C=C4OCOC4=CC=3)=CC=C21 RSOBTNQLFLVQCQ-UHFFFAOYSA-N 0.000 claims description 3
• YLXZAFDVGBKZRB-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethylsulfanyl]-1h-1,2,4-triazol-5-yl]butanoic acid Chemical compound C1=C2OCOC2=CC(C(CC=2NN=C(SCCC=3N=C4NCCCC4=CC=3)N=2)CC(=O)O)=C1 YLXZAFDVGBKZRB-UHFFFAOYSA-N 0.000 claims description 3
• ROXPYTIIMUHDCP-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-[2-[5-(methoxymethyl)-6-(methylamino)pyridin-2-yl]ethoxy]-1,2-oxazol-5-yl]butanoic acid Chemical compound C1=C(COC)C(NC)=NC(CCOC2=NOC(CC(CC(O)=O)C=3C=C4OCOC4=CC=3)=C2)=C1 ROXPYTIIMUHDCP-UHFFFAOYSA-N 0.000 claims description 3
• CDCSRAJFPQZHPJ-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-[3-(1,2,3,5-tetrahydropyrido[2,3-e][1,4]oxazepin-8-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound C1OCCNC2=NC(CCCC=3N=C(ON=3)CC(CC(=O)O)C=3C=C4OCOC4=CC=3)=CC=C21 CDCSRAJFPQZHPJ-UHFFFAOYSA-N 0.000 claims description 3
• NYFLVLDAXWLMHN-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-[3-(3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-6-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound C1=C2OCOC2=CC(C(CC=2ON=C(CCCC=3N=C4NCCOC4=CC=3)N=2)CC(=O)O)=C1 NYFLVLDAXWLMHN-UHFFFAOYSA-N 0.000 claims description 3
• HSACVEKFGJAKFH-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-[3-(4,5-dihydro-1h-imidazol-2-ylamino)propoxy]-1,2-oxazol-5-yl]butanoic acid Chemical compound C=1C=C2OCOC2=CC=1C(CC(=O)O)CC(ON=1)=CC=1OCCCNC1=NCCN1 HSACVEKFGJAKFH-UHFFFAOYSA-N 0.000 claims description 3
• LWGLUXRLLXLUNN-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-[4-[(6-methylpyridin-2-yl)amino]butyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound CC1=CC=CC(NCCCCC=2N=C(CC(CC(O)=O)C=3C=C4OCOC4=CC=3)ON=2)=N1 LWGLUXRLLXLUNN-UHFFFAOYSA-N 0.000 claims description 3
• JSODNUZFZZHGBQ-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-oxo-2-[2-(1,2,3,5-tetrahydropyrido[2,3-e][1,4]oxazepin-8-yl)ethyl]-1,2-oxazol-5-yl]butanoic acid Chemical compound C1OCCNC2=NC(CCN3C(=O)C=C(O3)CC(CC(=O)O)C=3C=C4OCOC4=CC=3)=CC=C21 JSODNUZFZZHGBQ-UHFFFAOYSA-N 0.000 claims description 3
• PBLZHMWMAPLNDP-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]tetrazol-1-yl]butanoic acid Chemical compound C1=C2OCOC2=CC(C(CN2C(=NN=N2)CCCC=2N=C3NCCCC3=CC=2)CC(=O)O)=C1 PBLZHMWMAPLNDP-UHFFFAOYSA-N 0.000 claims description 3
• IXOHEAGNRGVXGI-UHFFFAOYSA-N 3-(2,2-difluoro-1,3-benzodioxol-5-yl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;hydrochloride Chemical compound Cl.C1=C2OC(F)(F)OC2=CC(C(CC=2ON=C(CCCC=3N=C4NCCCC4=CC=3)N=2)CC(=O)O)=C1 IXOHEAGNRGVXGI-UHFFFAOYSA-N 0.000 claims description 3
• JWVHAAQROBLRGU-UHFFFAOYSA-N 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;hydrochloride Chemical compound Cl.O1CCOC2=CC(C(CC=3ON=C(CCCC=4N=C5NCCCC5=CC=4)N=3)CC(=O)O)=CC=C21 JWVHAAQROBLRGU-UHFFFAOYSA-N 0.000 claims description 3
• RYKUUFLXRURPPD-UHFFFAOYSA-N 3-(2-methyl-1,3-benzothiazol-5-yl)-4-[3-[3-(1-methyl-3,4-dihydro-2h-pyrido[2,3-b]pyrazin-6-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound C1=C2SC(C)=NC2=CC(C(CC(O)=O)CC=2ON=C(N=2)CCCC=2N=C3NCCN(C3=CC=2)C)=C1 RYKUUFLXRURPPD-UHFFFAOYSA-N 0.000 claims description 3
• JBVSLDQHOOIYNL-UHFFFAOYSA-N 3-(3,5-dimethoxyphenyl)-4-[3-[3-(1,2,3,5-tetrahydropyrido[2,3-e][1,4]oxazepin-8-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound COC1=CC(OC)=CC(C(CC(O)=O)CC=2ON=C(CCCC=3N=C4NCCOCC4=CC=3)N=2)=C1 JBVSLDQHOOIYNL-UHFFFAOYSA-N 0.000 claims description 3
• CBAPPZOMJBVAKP-UHFFFAOYSA-N 3-(3-cyanophenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound N=1C(CCCC=2N=C3NCCCC3=CC=2)=NOC=1CC(CC(=O)O)C1=CC=CC(C#N)=C1 CBAPPZOMJBVAKP-UHFFFAOYSA-N 0.000 claims description 3
• NGHDDAICORKIND-UHFFFAOYSA-N 3-(3-fluoro-4-methoxyphenyl)-4-[3-[3-(1-methyl-3,4-dihydro-2h-pyrido[2,3-b]pyrazin-6-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound C1=C(F)C(OC)=CC=C1C(CC(O)=O)CC1=NC(CCCC=2N=C3NCCN(C)C3=CC=2)=NO1 NGHDDAICORKIND-UHFFFAOYSA-N 0.000 claims description 3
• FHQUUTACMCLFHR-UHFFFAOYSA-N 3-(3-fluoro-4-methylphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;hydrochloride Chemical compound Cl.C1=C(F)C(C)=CC=C1C(CC(O)=O)CC1=NC(CCCC=2N=C3NCCCC3=CC=2)=NO1 FHQUUTACMCLFHR-UHFFFAOYSA-N 0.000 claims description 3
• VQYCFLUSNXCEGT-UHFFFAOYSA-N 3-(3-phenylmethoxyphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;hydrochloride Chemical compound Cl.N=1C(CCCC=2N=C3NCCCC3=CC=2)=NOC=1CC(CC(=O)O)C(C=1)=CC=CC=1OCC1=CC=CC=C1 VQYCFLUSNXCEGT-UHFFFAOYSA-N 0.000 claims description 3
• UQOYEVHSWGMZQL-UHFFFAOYSA-N 3-(4-methoxy-3-methylphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;hydrochloride Chemical compound Cl.C1=C(C)C(OC)=CC=C1C(CC(O)=O)CC1=NC(CCCC=2N=C3NCCCC3=CC=2)=NO1 UQOYEVHSWGMZQL-UHFFFAOYSA-N 0.000 claims description 3
• WLYBACCZPCAVFW-UHFFFAOYSA-N 3-(4-phenylphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound N=1C(CCCC=2N=C3NCCCC3=CC=2)=NOC=1CC(CC(=O)O)C(C=C1)=CC=C1C1=CC=CC=C1 WLYBACCZPCAVFW-UHFFFAOYSA-N 0.000 claims description 3
• YEEBBNWKQGDACU-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound C1=NC(OC)=CC=C1C(CC(O)=O)CC1=NC(CCCC=2N=C3NCCCC3=CC=2)=NO1 YEEBBNWKQGDACU-UHFFFAOYSA-N 0.000 claims description 3
• WGRJGOPGMDAEFR-UHFFFAOYSA-N 3-[2-(furan-2-yl)-1,3-thiazol-5-yl]-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;hydrochloride Chemical compound Cl.N=1C(CCCC=2N=C3NCCCC3=CC=2)=NOC=1CC(CC(=O)O)C(S1)=CN=C1C1=CC=CO1 WGRJGOPGMDAEFR-UHFFFAOYSA-N 0.000 claims description 3
• DPNUYYWNFKCMSU-UHFFFAOYSA-N 3-[3-fluoro-5-(trifluoromethyl)phenyl]-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;hydrochloride Chemical compound Cl.N=1C(CCCC=2N=C3NCCCC3=CC=2)=NOC=1CC(CC(=O)O)C1=CC(F)=CC(C(F)(F)F)=C1 DPNUYYWNFKCMSU-UHFFFAOYSA-N 0.000 claims description 3
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• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
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• ZSQKPWDRKRFCKK-UHFFFAOYSA-N 4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]-3-(3,4,5-trimethoxyphenyl)butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=C(OC)C(OC)=CC(C(CC(O)=O)CC=2ON=C(CCCC=3N=C4NCCCC4=CC=3)N=2)=C1 ZSQKPWDRKRFCKK-UHFFFAOYSA-N 0.000 claims description 3
• RUDCKTXRNNMRJC-UHFFFAOYSA-N 4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]-3-[3-(trifluoromethoxy)phenyl]butanoic acid;hydrochloride Chemical compound Cl.N=1C(CCCC=2N=C3NCCCC3=CC=2)=NOC=1CC(CC(=O)O)C1=CC=CC(OC(F)(F)F)=C1 RUDCKTXRNNMRJC-UHFFFAOYSA-N 0.000 claims description 3
• ZSJYCTSCBRBVMI-UHFFFAOYSA-N 4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]-3-[4-(trifluoromethoxy)phenyl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N=1C(CCCC=2N=C3NCCCC3=CC=2)=NOC=1CC(CC(=O)O)C1=CC=C(OC(F)(F)F)C=C1 ZSJYCTSCBRBVMI-UHFFFAOYSA-N 0.000 claims description 3
• WUAGFBHBLUTPMZ-UHFFFAOYSA-N 4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]-3-[4-(trifluoromethyl)phenyl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N=1C(CCCC=2N=C3NCCCC3=CC=2)=NOC=1CC(CC(=O)O)C1=CC=C(C(F)(F)F)C=C1 WUAGFBHBLUTPMZ-UHFFFAOYSA-N 0.000 claims description 3
• PWAJNONNDOMAQX-UHFFFAOYSA-N 4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]-3-thiophen-3-ylbutanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N=1C(CCCC=2N=C3NCCCC3=CC=2)=NOC=1CC(CC(=O)O)C=1C=CSC=1 PWAJNONNDOMAQX-UHFFFAOYSA-N 0.000 claims description 3
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
• 230000015590 smooth muscle cell migration Effects 0.000 claims description 3
• 230000001225 therapeutic effect Effects 0.000 claims description 3
• WNYLILSLCAMOBL-UHFFFAOYSA-N 2-[1-[(2-methylpropan-2-yl)oxycarbonyl]-4-[[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]methyl]piperidin-4-yl]acetic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CN(C(=O)OC(C)(C)C)CCC1(CC(O)=O)CC1=NC(CCCC=2N=C3NCCCC3=CC=2)=NO1 WNYLILSLCAMOBL-UHFFFAOYSA-N 0.000 claims description 2
• ZDOVARHPJQDDJF-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-[2-(3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-6-yl)ethoxy]-1,2-oxazol-5-yl]butanoic acid Chemical compound C1=C2OCOC2=CC(C(CC=2ON=C(OCCC=3N=C4NCCOC4=CC=3)C=2)CC(=O)O)=C1 ZDOVARHPJQDDJF-UHFFFAOYSA-N 0.000 claims description 2
• JRVUMBDCNCWNEP-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-[2-[6-(methylamino)pyridin-2-yl]ethoxy]-1,2-oxazol-5-yl]butanoic acid Chemical compound CNC1=CC=CC(CCOC2=NOC(CC(CC(O)=O)C=3C=C4OCOC4=CC=3)=C2)=N1 JRVUMBDCNCWNEP-UHFFFAOYSA-N 0.000 claims description 2
• ZKRVINPRXJBKAM-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-methoxyphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound C1=C(C(C)(C)C)C(OC)=C(C(C)(C)C)C=C1C(CC(O)=O)CC1=NC(CCCC=2N=C3NCCCC3=CC=2)=NO1 ZKRVINPRXJBKAM-UHFFFAOYSA-N 0.000 claims description 2
• BRYHSBWPRALNAP-UHFFFAOYSA-N 3-(3,5-ditert-butylphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(C(CC(O)=O)CC=2ON=C(CCCC=3N=C4NCCCC4=CC=3)N=2)=C1 BRYHSBWPRALNAP-UHFFFAOYSA-N 0.000 claims description 2
• QFUVKTPRORHXRA-UHFFFAOYSA-N 3-(3-bromo-5-tert-butylphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound CC(C)(C)C1=CC(Br)=CC(C(CC(O)=O)CC=2ON=C(CCCC=3N=C4NCCCC4=CC=3)N=2)=C1 QFUVKTPRORHXRA-UHFFFAOYSA-N 0.000 claims description 2
• GSMIJCTVPDHZAQ-UHFFFAOYSA-N 3-(3-tert-butyl-5-iodophenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound CC(C)(C)C1=CC(I)=CC(C(CC(O)=O)CC=2ON=C(CCCC=3N=C4NCCCC4=CC=3)N=2)=C1 GSMIJCTVPDHZAQ-UHFFFAOYSA-N 0.000 claims description 2
• BZPNGHCFSIDBOB-UHFFFAOYSA-N 3-(5-tert-butyl-2-hydroxyphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound CC(C)(C)C1=CC=C(O)C(C(CC(O)=O)CC=2ON=C(CCCC=3N=C4NCCCC4=CC=3)N=2)=C1 BZPNGHCFSIDBOB-UHFFFAOYSA-N 0.000 claims description 2
• CIVJKPVHCHDURV-UHFFFAOYSA-N 3-(5-tert-butyl-2-methoxyphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound COC1=CC=C(C(C)(C)C)C=C1C(CC(O)=O)CC1=NC(CCCC=2N=C3NCCCC3=CC=2)=NO1 CIVJKPVHCHDURV-UHFFFAOYSA-N 0.000 claims description 2
• RCXGZFUQPOFOJD-UHFFFAOYSA-N 3-[3,5-ditert-butyl-2-(carboxymethoxy)phenyl]-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(C(CC(O)=O)CC=2ON=C(CCCC=3N=C4NCCCC4=CC=3)N=2)=C1OCC(O)=O RCXGZFUQPOFOJD-UHFFFAOYSA-N 0.000 claims description 2
• UKTOUMNCJBZSHR-UHFFFAOYSA-N 3-[3-tert-butyl-5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound FC(F)(F)C(O)(C(F)(F)F)C1=CC(C(C)(C)C)=CC(C(CC(O)=O)CC=2ON=C(CCCC=3N=C4NCCCC4=CC=3)N=2)=C1 UKTOUMNCJBZSHR-UHFFFAOYSA-N 0.000 claims description 2
• 238000011321 prophylaxis Methods 0.000 claims 2
• 210000001525 retina Anatomy 0.000 claims 2
• 150000003839 salts Chemical class 0.000 abstract description 17
• 230000002401 inhibitory effect Effects 0.000 abstract description 4
• 230000003042 antagnostic effect Effects 0.000 abstract description 2
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• 238000005481 NMR spectroscopy Methods 0.000 description 218
• 239000000243 solution Substances 0.000 description 182
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• 239000000047 product Substances 0.000 description 170
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• 150000003254 radicals Chemical class 0.000 description 43
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• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 14
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• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 12
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• 238000004587 chromatography analysis Methods 0.000 description 10
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