CA2507699A1 - Heteroarylalkanoic acids as integrin receptor antagonists - Google Patents

Info

Publication number

CA2507699A1

CA2507699A1 CA002507699A CA2507699A CA2507699A1 CA 2507699 A1 CA2507699 A1 CA 2507699A1 CA 002507699 A CA002507699 A CA 002507699A CA 2507699 A CA2507699 A CA 2507699A CA 2507699 A1 CA2507699 A1 CA 2507699A1

Authority

CA

Canada

Prior art keywords

tetrahydro

oxadiazol

propyl

naphthyridin

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 239000002253 acid Substances 0.000 title description 8
• 150000007513 acids Chemical class 0.000 title description 3
• 229940127449 Integrin Receptor Antagonists Drugs 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 143
• 238000000034 method Methods 0.000 claims abstract description 121
• 108010044426 integrins Proteins 0.000 claims abstract description 22
• 102000006495 integrins Human genes 0.000 claims abstract description 22
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
• 239000000203 mixture Substances 0.000 claims description 155
• -1 TFA salt Chemical class 0.000 claims description 84
• 206010028980 Neoplasm Diseases 0.000 claims description 17
• 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
• 230000002265 prevention Effects 0.000 claims description 8
• 208000001132 Osteoporosis Diseases 0.000 claims description 7
• 208000008750 humoral hypercalcemia of malignancy Diseases 0.000 claims description 7
• 208000037803 restenosis Diseases 0.000 claims description 7
• 230000015590 smooth muscle cell migration Effects 0.000 claims description 7
• 230000004614 tumor growth Effects 0.000 claims description 7
• 208000017442 Retinal disease Diseases 0.000 claims description 6
• 206010038923 Retinopathy Diseases 0.000 claims description 6
• 206010003246 arthritis Diseases 0.000 claims description 6
• 230000001404 mediated effect Effects 0.000 claims description 6
• LYNHFSQIXZQNND-UHFFFAOYSA-N 3-(2-methyl-1,3-benzothiazol-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.C1CCNC2=NC(CCCC=3N=C(ON=3)CC(CC(O)=O)C=3C=C4N=C(SC4=CC=3)C)=CC=C21 LYNHFSQIXZQNND-UHFFFAOYSA-N 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 241000124008 Mammalia Species 0.000 claims description 4
• HBEHSLGNWGNJDZ-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[1-methyl-5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethylsulfanyl]-1,2,4-triazol-3-yl]butanoic acid Chemical compound C1CCNC2=NC(CCSC3=NC(CC(CC(O)=O)C=4C=C5OCOC5=CC=4)=NN3C)=CC=C21 HBEHSLGNWGNJDZ-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
• 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 3
• PPJRJZHMZNSKGR-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-[3-[(pyridin-2-ylamino)methyl]phenyl]-1,2,4-oxadiazol-5-yl]butanoic acid;hydrochloride Chemical compound Cl.C=1C=C2OCOC2=CC=1C(CC(=O)O)CC(ON=1)=NC=1C(C=1)=CC=CC=1CNC1=CC=CC=N1 PPJRJZHMZNSKGR-UHFFFAOYSA-N 0.000 claims description 3
• FTJMPSGEXWPQCM-UHFFFAOYSA-N 3-(3-ethyl-1,2,4-oxadiazol-5-yl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCC1=NOC(C(CC(O)=O)CC=2ON=C(CCCC=3N=C4NCCCC4=CC=3)N=2)=N1 FTJMPSGEXWPQCM-UHFFFAOYSA-N 0.000 claims description 3
• VQKWZBIOHCKOOG-UHFFFAOYSA-N 3-(3-fluoro-4-methoxyphenyl)-4-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3,4-oxadiazol-2-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(F)C(OC)=CC=C1C(CC(O)=O)CC(O1)=NN=C1CCCC1=CC=C(CCCN2)C2=N1 VQKWZBIOHCKOOG-UHFFFAOYSA-N 0.000 claims description 3
• QVCBXGPBYLGCOE-UHFFFAOYSA-N 3-(3-methyl-1,2,4-oxadiazol-5-yl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=NOC(C(CC(O)=O)CC=2ON=C(CCCC=3N=C4NCCCC4=CC=3)N=2)=N1 QVCBXGPBYLGCOE-UHFFFAOYSA-N 0.000 claims description 3
• CFBMLFACPQFNGD-UHFFFAOYSA-N 3-(4-bromophenyl)-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=C(Br)C=C1 CFBMLFACPQFNGD-UHFFFAOYSA-N 0.000 claims description 3
• KZIZQRFVSSFXCX-UHFFFAOYSA-N 3-(4-methylphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(C)=CC=C1C(CC(O)=O)CC1=NC(CCCC=2N=C3NCCCC3=CC=2)=NO1 KZIZQRFVSSFXCX-UHFFFAOYSA-N 0.000 claims description 3
• ORZMIQPOSMDWNC-UHFFFAOYSA-N 3-(6-methoxypyridin-3-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=NC(OC)=CC=C1C(CC(O)=O)CC1=NC(CCCC=2N=C3NCCN(C)C3=CC=2)=NO1 ORZMIQPOSMDWNC-UHFFFAOYSA-N 0.000 claims description 3
• ZHCBRPZCBRLKOR-UHFFFAOYSA-N 3-[2-(3,4-difluorophenyl)-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(F)=C1 ZHCBRPZCBRLKOR-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• BUNGGTYANBJQAU-UHFFFAOYSA-N 3-[2-(4-methoxyphenyl)-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.C1=CC(OC)=CC=C1C1=NC=C(C(CC(O)=O)CC=2ON=C(CCCC=3N=C4NCCCC4=CC=3)N=2)S1 BUNGGTYANBJQAU-UHFFFAOYSA-N 0.000 claims description 3
• FYYCTBWJMQADDA-UHFFFAOYSA-N 3-benzyl-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]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)CC1=CC=CC=C1 FYYCTBWJMQADDA-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 2
• 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 2
• 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 2
• 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 2
• 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 2
• PKJUEZWOKCRAPB-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-[3-(2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazepin-7-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound O1CCCNC2=NC(CCCC=3N=C(ON=3)CC(CC(=O)O)C=3C=C4OCOC4=CC=3)=CC=C21 PKJUEZWOKCRAPB-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• FYRYDPMDUZRHCR-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3,4-thiadiazol-2-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C2OCOC2=CC(C(CC=2SC(CCCC=3N=C4NCCCC4=CC=3)=NN=2)CC(=O)O)=C1 FYRYDPMDUZRHCR-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• OSJYAQRUCTZSCP-UHFFFAOYSA-N 3-(1-benzofuran-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.C1=C2C=COC2=CC(C(CC=2ON=C(CCCC=3N=C4NCCCC4=CC=3)N=2)CC(=O)O)=C1 OSJYAQRUCTZSCP-UHFFFAOYSA-N 0.000 claims description 2
• BJSXXAYGZSDZLM-UHFFFAOYSA-N 3-(1-methylindol-3-yl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2N(C)C=C1C(CC(O)=O)CC1=NC(CCCC=2N=C3NCCCC3=CC=2)=NO1 BJSXXAYGZSDZLM-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• CPZYGKFRYYALMR-UHFFFAOYSA-N 3-(2-methyl-1,3-benzothiazol-5-yl)-4-[3-[3-(2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazepin-7-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound O1CCCNC2=NC(CCCC=3N=C(ON=3)CC(CC(O)=O)C=3C=C4N=C(SC4=CC=3)C)=CC=C21 CPZYGKFRYYALMR-UHFFFAOYSA-N 0.000 claims description 2
• SDXMKDWSMLINTG-UHFFFAOYSA-N 3-(2-methyl-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;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.S1C(C)=NC=C1C(CC(O)=O)CC1=NC(CCCC=2N=C3NCCCC3=CC=2)=NO1 SDXMKDWSMLINTG-UHFFFAOYSA-N 0.000 claims description 2
• CVYQWENAOPWQAJ-UHFFFAOYSA-N 3-(2-methyl-1,3-thiazol-5-yl)-4-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3,4-thiadiazol-2-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.S1C(C)=NC=C1C(CC(O)=O)CC(S1)=NN=C1CCCC1=CC=C(CCCN2)C2=N1 CVYQWENAOPWQAJ-UHFFFAOYSA-N 0.000 claims description 2
• QKJMGSWFHUEQBI-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]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(Cl)C(Cl)=C1 QKJMGSWFHUEQBI-UHFFFAOYSA-N 0.000 claims description 2
• XMWGBPYPERBFKE-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-4-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3,4-oxadiazol-2-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N=1N=C(CCCC=2N=C3NCCCC3=CC=2)OC=1CC(CC(=O)O)C1=CC(F)=CC(F)=C1 XMWGBPYPERBFKE-UHFFFAOYSA-N 0.000 claims description 2
• NMRSALQREBNJGU-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-4-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3,4-thiadiazol-2-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N=1N=C(CCCC=2N=C3NCCCC3=CC=2)SC=1CC(CC(=O)O)C1=CC(F)=CC(F)=C1 NMRSALQREBNJGU-UHFFFAOYSA-N 0.000 claims description 2
• IOUFXDVKKOZALB-UHFFFAOYSA-N 3-(3,5-dimethoxyphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC(OC)=CC(C(CC(O)=O)CC=2ON=C(CCCC=3N=C4NCCCC4=CC=3)N=2)=C1 IOUFXDVKKOZALB-UHFFFAOYSA-N 0.000 claims description 2
• OTRUEEBVLYQWQA-UHFFFAOYSA-N 3-(3,5-dimethoxyphenyl)-4-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3,4-oxadiazol-2-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC(OC)=CC(C(CC(O)=O)CC=2OC(CCCC=3N=C4NCCCC4=CC=3)=NN=2)=C1 OTRUEEBVLYQWQA-UHFFFAOYSA-N 0.000 claims description 2
• ZCKWLKNBCDBJKE-UHFFFAOYSA-N 3-(3-chlorophenyl)-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=CC(Cl)=C1 ZCKWLKNBCDBJKE-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• 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 2
• DNCICVGKRLFGIK-UHFFFAOYSA-N 3-(3-fluorophenyl)-4-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3,4-oxadiazol-2-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N=1N=C(CCCC=2N=C3NCCCC3=CC=2)OC=1CC(CC(=O)O)C1=CC=CC(F)=C1 DNCICVGKRLFGIK-UHFFFAOYSA-N 0.000 claims description 2
• OMDJGQFYKPVTFA-UHFFFAOYSA-N 3-(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.CC1=CC=CC(C(CC(O)=O)CC=2ON=C(CCCC=3N=C4NCCCC4=CC=3)N=2)=C1 OMDJGQFYKPVTFA-UHFFFAOYSA-N 0.000 claims description 2
• RRCYQIPQVLKABX-UHFFFAOYSA-N 3-(3-phenoxyphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]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)C(C=1)=CC=CC=1OC1=CC=CC=C1 RRCYQIPQVLKABX-UHFFFAOYSA-N 0.000 claims description 2
• RAYPRQYUDRHPHD-UHFFFAOYSA-N 3-(4-fluorophenyl)-4-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3,4-oxadiazol-2-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N=1N=C(CCCC=2N=C3NCCCC3=CC=2)OC=1CC(CC(=O)O)C1=CC=C(F)C=C1 RAYPRQYUDRHPHD-UHFFFAOYSA-N 0.000 claims description 2
• ROQBCZBWPYSART-UHFFFAOYSA-N 3-(4-fluorophenyl)-4-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3,4-thiadiazol-2-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N=1N=C(CCCC=2N=C3NCCCC3=CC=2)SC=1CC(CC(=O)O)C1=CC=C(F)C=C1 ROQBCZBWPYSART-UHFFFAOYSA-N 0.000 claims description 2
• GUBVAUTVSFLISE-UHFFFAOYSA-N 3-(4-methylsulfonylphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(S(=O)(=O)C)=CC=C1C(CC(O)=O)CC1=NC(CCCC=2N=C3NCCCC3=CC=2)=NO1 GUBVAUTVSFLISE-UHFFFAOYSA-N 0.000 claims description 2
• RFLKJLJPBLOBDU-UHFFFAOYSA-N 3-(4-phenoxyphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]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)C(C=C1)=CC=C1OC1=CC=CC=C1 RFLKJLJPBLOBDU-UHFFFAOYSA-N 0.000 claims description 2
• WAEVSGMZUFUTGB-UHFFFAOYSA-N 3-(furan-2-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)C1=CC=CO1 WAEVSGMZUFUTGB-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• CHYGEEZJWFPWAA-UHFFFAOYSA-N 4-[3-[3-(3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-6-yl)propyl]-1,2,4-oxadiazol-5-yl]-3-(3,5-dimethoxyphenyl)butanoic acid Chemical compound COC1=CC(OC)=CC(C(CC(O)=O)CC=2ON=C(CCCC=3N=C4NCCOC4=CC=3)N=2)=C1 CHYGEEZJWFPWAA-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• 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 2
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• SZLCWBQHDHYCNX-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[3-[3-[6-(ethylamino)pyridin-2-yl]propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCNC1=CC=CC(CCCC=2N=C(CC(CC(O)=O)C=3C=C4OCOC4=CC=3)ON=2)=N1 SZLCWBQHDHYCNX-UHFFFAOYSA-N 0.000 claims 1
• QGNLXBUGTQILQD-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[4-methyl-5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethylsulfanyl]-1,2,4-triazol-3-yl]butanoic acid Chemical compound C1CCNC2=NC(CCSC3=NN=C(CC(CC(O)=O)C=4C=C5OCOC5=CC=4)N3C)=CC=C21 QGNLXBUGTQILQD-UHFFFAOYSA-N 0.000 claims 1
• KKFGQALWUVFAGJ-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-4-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3,4-oxadiazol-2-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C2OCOC2=CC(C(CC=2OC(CCCC=3N=C4NCCCC4=CC=3)=NN=2)CC(=O)O)=C1 KKFGQALWUVFAGJ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• AQLQHFTZUNTUKQ-UHFFFAOYSA-N 3-(1,3-benzoxazol-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.C1=C2N=COC2=CC(C(CC=2ON=C(CCCC=3N=C4NCCCC4=CC=3)N=2)CC(=O)O)=C1 AQLQHFTZUNTUKQ-UHFFFAOYSA-N 0.000 claims 1
• XGRALTFTJQMEJX-UHFFFAOYSA-N 3-(1-benzofuran-2-yl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=C2OC(C(CC=3ON=C(CCCC=4N=C5NCCCC5=CC=4)N=3)CC(=O)O)=CC2=C1 XGRALTFTJQMEJX-UHFFFAOYSA-N 0.000 claims 1
• MAHCQYGZWMRXII-UHFFFAOYSA-N 3-(1-phenylpyrazol-4-yl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]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)C(=C1)C=NN1C1=CC=CC=C1 MAHCQYGZWMRXII-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• WOMDEZRCDFCXJF-UHFFFAOYSA-N 3-(2,3-dihydro-1-benzofuran-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.C1=C2CCOC2=CC(C(CC=2ON=C(CCCC=3N=C4NCCCC4=CC=3)N=2)CC(=O)O)=C1 WOMDEZRCDFCXJF-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• RIAGAZGVRHSWPM-UHFFFAOYSA-N 3-(2-methyl-1,3-thiazol-5-yl)-4-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3,4-oxadiazol-2-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.S1C(C)=NC=C1C(CC(O)=O)CC(O1)=NN=C1CCCC1=CC=C(CCCN2)C2=N1 RIAGAZGVRHSWPM-UHFFFAOYSA-N 0.000 claims 1
• KYVQBEKIBXQJJG-UHFFFAOYSA-N 3-(2-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.CC1=CC=CC=C1C(CC(O)=O)CC1=NC(CCCC=2N=C3NCCCC3=CC=2)=NO1 KYVQBEKIBXQJJG-UHFFFAOYSA-N 0.000 claims 1
• VONJVUMPAHBQQQ-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(OC)C(OC)=CC=C1C(CC(O)=O)CC1=NC(CCCC=2N=C3NCCCC3=CC=2)=NO1 VONJVUMPAHBQQQ-UHFFFAOYSA-N 0.000 claims 1
• KUBHNKTUXNOMHE-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]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(Cl)=CC(Cl)=C1 KUBHNKTUXNOMHE-UHFFFAOYSA-N 0.000 claims 1
• VNABBIMAAHCJJY-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-4-[3-[3-(2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazepin-7-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound N=1C(CCCC=2N=C3NCCCOC3=CC=2)=NOC=1CC(CC(=O)O)C1=CC(F)=CC(F)=C1 VNABBIMAAHCJJY-UHFFFAOYSA-N 0.000 claims 1
• HPCHSHSREUTFDX-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]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(F)=CC(F)=C1 HPCHSHSREUTFDX-UHFFFAOYSA-N 0.000 claims 1
• WQTNQQMBOWZEMG-UHFFFAOYSA-N 3-(3,5-dimethoxyphenyl)-4-[3-[3-(2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazepin-7-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=C4NCCCOC4=CC=3)N=2)=C1 WQTNQQMBOWZEMG-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• JIMSGZMNTWQCNU-UHFFFAOYSA-N 3-(3-bromo-4-methoxyphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(Br)C(OC)=CC=C1C(CC(O)=O)CC1=NC(CCCC=2N=C3NCCCC3=CC=2)=NO1 JIMSGZMNTWQCNU-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• VLXYVWRJDWOKFB-UHFFFAOYSA-N 3-(3-bromophenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]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=CC(Br)=C1 VLXYVWRJDWOKFB-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• OOSXWQOTFPNALX-UHFFFAOYSA-N 3-(3-fluoro-4-methoxyphenyl)-4-[3-[3-(2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazepin-7-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=C3NCCCOC3=CC=2)=NO1 OOSXWQOTFPNALX-UHFFFAOYSA-N 0.000 claims 1
• XLHLUTQYFIHJFX-UHFFFAOYSA-N 3-(3-fluoro-4-methoxyphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(F)C(OC)=CC=C1C(CC(O)=O)CC1=NC(CCCC=2N=C3NCCCC3=CC=2)=NO1 XLHLUTQYFIHJFX-UHFFFAOYSA-N 0.000 claims 1
• MALDRJVVERJPFH-UHFFFAOYSA-N 3-(3-fluorophenyl)-4-[3-[3-[6-(methylamino)pyridin-2-yl]propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CNC1=CC=CC(CCCC=2N=C(CC(CC(O)=O)C=3C=C(F)C=CC=3)ON=2)=N1 MALDRJVVERJPFH-UHFFFAOYSA-N 0.000 claims 1
• UXUOHNQEPDEHRL-UHFFFAOYSA-N 3-(3-nitrophenyl)-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=CC([N+]([O-])=O)=C1 UXUOHNQEPDEHRL-UHFFFAOYSA-N 0.000 claims 1
• AOVWTNBWJSEXEO-UHFFFAOYSA-N 3-(3-phenyl-1,2,4-oxadiazol-5-yl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]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)C(ON=1)=NC=1C1=CC=CC=C1 AOVWTNBWJSEXEO-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• FLECRSNSBCPTDH-UHFFFAOYSA-N 3-(4-fluoro-3-methoxyphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(F)C(OC)=CC(C(CC(O)=O)CC=2ON=C(CCCC=3N=C4NCCCC4=CC=3)N=2)=C1 FLECRSNSBCPTDH-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• JZRNZSACMDLWQL-UHFFFAOYSA-N 3-(4-methylsulfanylphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]butanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(SC)=CC=C1C(CC(O)=O)CC1=NC(CCCC=2N=C3NCCCC3=CC=2)=NO1 JZRNZSACMDLWQL-UHFFFAOYSA-N 0.000 claims 1
• VBIOCKOLYGVPFA-UHFFFAOYSA-N 3-(4-phenylmethoxyphenyl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]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)C(C=C1)=CC=C1OCC1=CC=CC=C1 VBIOCKOLYGVPFA-UHFFFAOYSA-N 0.000 claims 1
• NZNSAPLWGTYAHG-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;hydrochloride Chemical compound Cl.N=1C(CCCC=2N=C3NCCCC3=CC=2)=NOC=1CC(CC(=O)O)C(C=C1)=CC=C1C1=CC=CC=C1 NZNSAPLWGTYAHG-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• AYRYCWSYOJAHSG-UHFFFAOYSA-N 3-(6-methoxynaphthalen-2-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.C1CCNC2=NC(CCCC=3N=C(ON=3)CC(CC(O)=O)C3=CC4=CC=C(C=C4C=C3)OC)=CC=C21 AYRYCWSYOJAHSG-UHFFFAOYSA-N 0.000 claims 1
• QHSKOAKVMQHGPS-UHFFFAOYSA-N 3-(6-methoxypyridin-3-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=NC(OC)=CC=C1C(CC(O)=O)CC1=CC(OCCC=2N=C3NCCCC3=CC=2)=NO1 QHSKOAKVMQHGPS-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• YJWYZAFELKYCHB-UHFFFAOYSA-N 3-(7-fluoro-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;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(C=C1F)=CC2=C1OCO2 YJWYZAFELKYCHB-UHFFFAOYSA-N 0.000 claims 1
• YDVSIYHPPQFPMR-UHFFFAOYSA-N 3-(furan-3-yl)-4-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,2,4-oxadiazol-5-yl]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)C=1C=COC=1 YDVSIYHPPQFPMR-UHFFFAOYSA-N 0.000 claims 1
• RCJKNRQMQPJQGQ-UHFFFAOYSA-N 3-[2-(3,5-difluorophenyl)-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(F)=CC(F)=C1 RCJKNRQMQPJQGQ-UHFFFAOYSA-N 0.000 claims 1
• WPRZWONATNXRPZ-UHFFFAOYSA-N 3-[2-(4-chlorophenyl)-1,3-thiazol-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 C=1C(OCCC=2N=C3NCCCC3=CC=2)=NOC=1CC(CC(=O)O)C(S1)=CN=C1C1=CC=C(Cl)C=C1 WPRZWONATNXRPZ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• NNFGZFOBVUXHGG-UHFFFAOYSA-N 3-naphthalen-2-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=CC=CC2=CC(C(CC=3ON=C(CCCC=4N=C5NCCCC5=CC=4)N=3)CC(=O)O)=CC=C21 NNFGZFOBVUXHGG-UHFFFAOYSA-N 0.000 claims 1
• HVRAWESQGQTPLL-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-trifluorophenyl)butanoic acid;hydrochloride Chemical compound Cl.N=1C(CCCC=2N=C3NCCCC3=CC=2)=NOC=1CC(CC(=O)O)C1=CC(F)=C(F)C(F)=C1 HVRAWESQGQTPLL-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 150000003839 salts Chemical class 0.000 abstract description 15
• 230000002401 inhibitory effect Effects 0.000 abstract description 12
• 230000003042 antagnostic effect Effects 0.000 abstract description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 362
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 350
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 234
• 238000005481 NMR spectroscopy Methods 0.000 description 217
• 239000000243 solution Substances 0.000 description 194
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 192
• 239000000047 product Substances 0.000 description 169
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 152
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 150
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 146
• 235000019439 ethyl acetate Nutrition 0.000 description 139
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• 239000011541 reaction mixture Substances 0.000 description 113
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 102
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 95
• 238000006243 chemical reaction Methods 0.000 description 95
• 230000015572 biosynthetic process Effects 0.000 description 93
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 93
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 93
• 238000003786 synthesis reaction Methods 0.000 description 91
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 87
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• 239000012267 brine Substances 0.000 description 76
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 76
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
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• 239000007787 solid Substances 0.000 description 65
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• 125000000217 alkyl group Chemical group 0.000 description 59
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• 125000003118 aryl group Chemical group 0.000 description 50
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 50
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 49
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 49
• 239000012044 organic layer Substances 0.000 description 48
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 46
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• 238000003818 flash chromatography Methods 0.000 description 38
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 38
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• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 35
• 238000001819 mass spectrum Methods 0.000 description 35
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• 229960000583 acetic acid Drugs 0.000 description 33
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• 238000002360 preparation method Methods 0.000 description 33
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• 239000003480 eluent Substances 0.000 description 29
• 239000000706 filtrate Substances 0.000 description 29
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• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 28
• 125000003545 alkoxy group Chemical group 0.000 description 28
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 28
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 28
• 238000004007 reversed phase HPLC Methods 0.000 description 28
• 238000003756 stirring Methods 0.000 description 28
• 238000005160 1H NMR spectroscopy Methods 0.000 description 27
• 125000001188 haloalkyl group Chemical group 0.000 description 27
• 125000001072 heteroaryl group Chemical group 0.000 description 27
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 27
• 229910052757 nitrogen Inorganic materials 0.000 description 25
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 24
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 24
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• 239000012043 crude product Substances 0.000 description 22
• 150000008064 anhydrides Chemical class 0.000 description 21
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• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
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• BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 1
• FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
• COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
• 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
• 230000002792 vascular Effects 0.000 description 1
• 210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 230000009385 viral infection Effects 0.000 description 1
• 230000003612 virological effect Effects 0.000 description 1
• 239000003039 volatile agent Substances 0.000 description 1
• 238000005303 weighing Methods 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 229940102001 zinc bromide Drugs 0.000 description 1
• GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1