SK17442001A3 - Deriváty kyseliny nonánovej, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents

Info

Publication number

SK17442001A3

SK17442001A3 SK1744-2001A SK17442001A SK17442001A3 SK 17442001 A3 SK17442001 A3 SK 17442001A3 SK 17442001 A SK17442001 A SK 17442001A SK 17442001 A3 SK17442001 A3 SK 17442001A3

Authority

SK

Slovakia

Prior art keywords

tetrahydro

oxo

naphthyridin

nonanoic acid

pyrimidin

Prior art date

1999-06-02

Links

• Espacenet
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• 239000002253 acid Substances 0.000 title claims description 43
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 30
• 150000001875 compounds Chemical class 0.000 claims abstract description 73
• 208000006386 Bone Resorption Diseases 0.000 claims abstract description 37
• 230000024279 bone resorption Effects 0.000 claims abstract description 37
• 150000002842 nonanoic acids Chemical class 0.000 claims abstract description 36
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 29
• 108010044426 integrins Proteins 0.000 claims abstract description 29
• 102000006495 integrins Human genes 0.000 claims abstract description 29
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 25
• 201000010099 disease Diseases 0.000 claims abstract description 24
• 208000001132 Osteoporosis Diseases 0.000 claims abstract description 23
• 230000004614 tumor growth Effects 0.000 claims abstract description 22
• 230000033115 angiogenesis Effects 0.000 claims abstract description 19
• 201000011510 cancer Diseases 0.000 claims abstract description 19
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 18
• 206010061218 Inflammation Diseases 0.000 claims abstract description 17
• 230000004054 inflammatory process Effects 0.000 claims abstract description 17
• 206010012689 Diabetic retinopathy Diseases 0.000 claims abstract description 16
• 208000002780 macular degeneration Diseases 0.000 claims abstract description 16
• 208000037803 restenosis Diseases 0.000 claims abstract description 16
• 230000003612 virological effect Effects 0.000 claims abstract description 14
• 206010003246 arthritis Diseases 0.000 claims abstract description 12
• 206010061289 metastatic neoplasm Diseases 0.000 claims abstract description 11
• 230000002757 inflammatory effect Effects 0.000 claims abstract description 10
• -1 (2) naphthyl Chemical group 0.000 claims description 422
• 125000000217 alkyl group Chemical group 0.000 claims description 191
• 229910052739 hydrogen Inorganic materials 0.000 claims description 81
• 239000001257 hydrogen Substances 0.000 claims description 80
• FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 78
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 70
• 125000001424 substituent group Chemical group 0.000 claims description 65
• 239000000203 mixture Substances 0.000 claims description 64
• 125000003118 aryl group Chemical group 0.000 claims description 58
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 50
• 238000000034 method Methods 0.000 claims description 49
• 150000003839 salts Chemical class 0.000 claims description 38
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
• 239000000126 substance Substances 0.000 claims description 36
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 35
• 241000124008 Mammalia Species 0.000 claims description 34
• 125000004321 azepin-2-yl group Chemical group [H]N1C([H])=C([H])C([H])=C([H])C([H])=C1* 0.000 claims description 34
• 125000003545 alkoxy group Chemical group 0.000 claims description 32
• 150000002431 hydrogen Chemical class 0.000 claims description 31
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
• 229910052736 halogen Inorganic materials 0.000 claims description 28
• 150000002367 halogens Chemical class 0.000 claims description 28
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 28
• 210000002997 osteoclast Anatomy 0.000 claims description 28
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 25
• 239000003795 chemical substances by application Substances 0.000 claims description 24
• 125000004432 carbon atom Chemical group C* 0.000 claims description 23
• 125000003282 alkyl amino group Chemical group 0.000 claims description 22
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 22
• 125000005493 quinolyl group Chemical group 0.000 claims description 21
• 230000003042 antagnostic effect Effects 0.000 claims description 19
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 19
• 125000004076 pyridyl group Chemical group 0.000 claims description 19
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
• 229920006395 saturated elastomer Polymers 0.000 claims description 17
• 150000002148 esters Chemical class 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 13
• 108010041341 Integrin alpha1 Proteins 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 12
• 230000000694 effects Effects 0.000 claims description 12
• 229940122361 Bisphosphonate Drugs 0.000 claims description 11
• 125000004442 acylamino group Chemical group 0.000 claims description 11
• 150000004663 bisphosphonates Chemical class 0.000 claims description 11
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 11
• 229910052757 nitrogen Inorganic materials 0.000 claims description 10
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 9
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 9
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
• 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 9
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
• 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 9
• 239000003937 drug carrier Substances 0.000 claims description 9
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 9
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 8
• 239000004480 active ingredient Substances 0.000 claims description 8
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
• 230000009977 dual effect Effects 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 239000003112 inhibitor Substances 0.000 claims description 8
• 230000001404 mediated effect Effects 0.000 claims description 8
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 7
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
• 239000002834 estrogen receptor modulator Substances 0.000 claims description 6
• 125000002541 furyl group Chemical group 0.000 claims description 6
• 239000000849 selective androgen receptor modulator Substances 0.000 claims description 6
• OEJMPXAXGWKGQE-QFIPXVFZSA-N (2S)-2-(1-benzofuran-6-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound OC(=O)[C@@H](CCC(=O)CCCCc1ccc2CCCNc2n1)c1ccc2ccoc2c1 OEJMPXAXGWKGQE-QFIPXVFZSA-N 0.000 claims description 5
• PXKRBNCCUNMPMJ-FQEVSTJZSA-N (2s)-5-oxo-2-quinoxalin-2-yl-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=CC=CC2=NC([C@H](CCC(=O)CCCCC=3N=C4NCCCC4=CC=3)C(=O)O)=CN=C21 PXKRBNCCUNMPMJ-FQEVSTJZSA-N 0.000 claims description 5
• OVPGZOBAJSOERO-AWEZNQCLSA-N (3s)-9-[6-(methylamino)pyridin-2-yl]-5-oxo-3-pyrimidin-5-ylnonanoic acid Chemical compound CNC1=CC=CC(CCCCC(=O)C[C@@H](CC(O)=O)C=2C=NC=NC=2)=N1 OVPGZOBAJSOERO-AWEZNQCLSA-N 0.000 claims description 5
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
• 102100033367 Appetite-regulating hormone Human genes 0.000 claims description 5
• 101710111255 Appetite-regulating hormone Proteins 0.000 claims description 5
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 5
• 229940122156 Cathepsin K inhibitor Drugs 0.000 claims description 5
• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims description 5
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
• 125000004414 alkyl thio group Chemical group 0.000 claims description 5
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
• 239000003324 growth hormone secretagogue Substances 0.000 claims description 5
• 230000030991 negative regulation of bone resorption Effects 0.000 claims description 5
• 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 5
• 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 5
• FDHJJPVHTYVRIJ-NRFANRHFSA-N (2S)-2-(5-methoxypyridin-3-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound COc1cncc(c1)[C@H](CCC(=O)CCCCc1ccc2CCCNc2n1)C(O)=O FDHJJPVHTYVRIJ-NRFANRHFSA-N 0.000 claims description 4
• CITGFEDLBWRGEJ-WCSIJFPASA-N (2S)-5-hydroxy-2-quinolin-3-yl-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound N1=CC(=CC2=CC=CC=C12)[C@@H](C(=O)O)CCC(CCCCC1=NC=2NCCCC2C=C1)O CITGFEDLBWRGEJ-WCSIJFPASA-N 0.000 claims description 4
• UPNUQZLHTJMHSH-GOSISDBHSA-N (2r)-5-oxo-2-pyrazin-2-yl-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1([C@@H](CCC(=O)CCCCC=2N=C3NCCCC3=CC=2)C(=O)O)=CN=CC=N1 UPNUQZLHTJMHSH-GOSISDBHSA-N 0.000 claims description 4
• PXKRBNCCUNMPMJ-HXUWFJFHSA-N (2r)-5-oxo-2-quinoxalin-2-yl-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=CC=CC2=NC([C@@H](CCC(=O)CCCCC=3N=C4NCCCC4=CC=3)C(=O)O)=CN=C21 PXKRBNCCUNMPMJ-HXUWFJFHSA-N 0.000 claims description 4
• IGYRCQAUOKNOCX-SFHVURJKSA-N (2s)-2-(6-methoxypyridazin-3-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound N1=NC(OC)=CC=C1[C@@H](C(O)=O)CCC(=O)CCCCC1=CC=C(CCCN2)C2=N1 IGYRCQAUOKNOCX-SFHVURJKSA-N 0.000 claims description 4
• OVPGZOBAJSOERO-CQSZACIVSA-N (3r)-9-[6-(methylamino)pyridin-2-yl]-5-oxo-3-pyrimidin-5-ylnonanoic acid Chemical compound CNC1=CC=CC(CCCCC(=O)C[C@H](CC(O)=O)C=2C=NC=NC=2)=N1 OVPGZOBAJSOERO-CQSZACIVSA-N 0.000 claims description 4
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 4
• AXWCRKTXRMIKPF-UHFFFAOYSA-N 3-(2-methylpyrimidin-5-yl)-7-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=NC(C)=NC=C1C(CC(O)=O)CCCC(=O)CCC1=CC=C(CCCN2)C2=N1 AXWCRKTXRMIKPF-UHFFFAOYSA-N 0.000 claims description 4
• 229940124226 Farnesyltransferase inhibitor Drugs 0.000 claims description 4
• 229940122091 Geranylgeranyltransferase inhibitor Drugs 0.000 claims description 4
• 230000001028 anti-proliverative effect Effects 0.000 claims description 4
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 231100000433 cytotoxic Toxicity 0.000 claims description 4
• 230000001472 cytotoxic effect Effects 0.000 claims description 4
• 239000003102 growth factor Substances 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• 230000001939 inductive effect Effects 0.000 claims description 4
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• CITGFEDLBWRGEJ-OZAIVSQSSA-N (2R)-5-hydroxy-2-quinolin-3-yl-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound N1=CC(=CC2=CC=CC=C12)[C@H](C(=O)O)CCC(CCCCC1=NC=2NCCCC2C=C1)O CITGFEDLBWRGEJ-OZAIVSQSSA-N 0.000 claims description 3
• LZQMLZXBYVIKNA-LJQANCHMSA-N (2R)-5-oxo-2-pyrimidin-5-yl-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound OC(=O)[C@H](CCC(=O)CCCCc1ccc2CCCNc2n1)c1cncnc1 LZQMLZXBYVIKNA-LJQANCHMSA-N 0.000 claims description 3
• LUCRVWWAYGIHAB-IBGZPJMESA-N (2S)-2-(5-methylpyrazin-2-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound Cc1cnc(cn1)[C@H](CCC(=O)CCCCc1ccc2CCCNc2n1)C(O)=O LUCRVWWAYGIHAB-IBGZPJMESA-N 0.000 claims description 3
• GORJZZGBALVRQI-NRFANRHFSA-N (2S)-2-(6-ethoxypyridin-3-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound CCOc1ccc(cn1)[C@H](CCC(=O)CCCCc1ccc2CCCNc2n1)C(O)=O GORJZZGBALVRQI-NRFANRHFSA-N 0.000 claims description 3
• OEJMPXAXGWKGQE-JOCHJYFZSA-N (2r)-2-(1-benzofuran-6-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=C2C=COC2=CC([C@@H](CCC(=O)CCCCC=2N=C3NCCCC3=CC=2)C(=O)O)=C1 OEJMPXAXGWKGQE-JOCHJYFZSA-N 0.000 claims description 3
• KYIUESBVXDONBH-HXUWFJFHSA-N (2r)-2-(2-methylpyrimidin-5-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=NC(C)=NC=C1[C@H](C(O)=O)CCC(=O)CCCCC1=CC=C(CCCN2)C2=N1 KYIUESBVXDONBH-HXUWFJFHSA-N 0.000 claims description 3
• FDHJJPVHTYVRIJ-OAQYLSRUSA-N (2r)-2-(5-methoxypyridin-3-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound COC1=CN=CC([C@@H](CCC(=O)CCCCC=2N=C3NCCCC3=CC=2)C(O)=O)=C1 FDHJJPVHTYVRIJ-OAQYLSRUSA-N 0.000 claims description 3
• IGYRCQAUOKNOCX-GOSISDBHSA-N (2r)-2-(6-methoxypyridazin-3-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound N1=NC(OC)=CC=C1[C@H](C(O)=O)CCC(=O)CCCCC1=CC=C(CCCN2)C2=N1 IGYRCQAUOKNOCX-GOSISDBHSA-N 0.000 claims description 3
• QHDQGGPLXWADGC-LJQANCHMSA-N (2r)-2-[2-(methylamino)pyrimidin-5-yl]-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=NC(NC)=NC=C1[C@H](C(O)=O)CCC(=O)CCCCC1=CC=C(CCCN2)C2=N1 QHDQGGPLXWADGC-LJQANCHMSA-N 0.000 claims description 3
• KCXMGCPGJGKFNN-HSZRJFAPSA-N (2r)-5-oxo-2-quinolin-3-yl-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=CC=CC2=CC([C@@H](CCC(=O)CCCCC=3N=C4NCCCC4=CC=3)C(=O)O)=CN=C21 KCXMGCPGJGKFNN-HSZRJFAPSA-N 0.000 claims description 3
• AYDDTLCITNWPKO-QFIPXVFZSA-N (2s)-2-(2,3-dihydro-1-benzofuran-6-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=C2CCOC2=CC([C@H](CCC(=O)CCCCC=2N=C3NCCCC3=CC=2)C(=O)O)=C1 AYDDTLCITNWPKO-QFIPXVFZSA-N 0.000 claims description 3
• VNNKGLKYUJUPHO-FQEVSTJZSA-N (2s)-2-(2-ethoxypyrimidin-5-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=NC(OCC)=NC=C1[C@@H](C(O)=O)CCC(=O)CCCCC1=CC=C(CCCN2)C2=N1 VNNKGLKYUJUPHO-FQEVSTJZSA-N 0.000 claims description 3
• UPNUQZLHTJMHSH-SFHVURJKSA-N (2s)-5-oxo-2-pyrazin-2-yl-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1([C@H](CCC(=O)CCCCC=2N=C3NCCCC3=CC=2)C(=O)O)=CN=CC=N1 UPNUQZLHTJMHSH-SFHVURJKSA-N 0.000 claims description 3
• FGXZHWSARJMWBB-NRFANRHFSA-N (2s)-9-(3-cyclopropyl-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)-2-(2-methylpyrimidin-5-yl)-5-oxononanoic acid Chemical compound C1=NC(C)=NC=C1[C@@H](C(O)=O)CCC(=O)CCCCC(C(=C1)C2CC2)=NC2=C1CCCN2 FGXZHWSARJMWBB-NRFANRHFSA-N 0.000 claims description 3
• DMHGRCAGNKKTJL-QHCPKHFHSA-N (2s)-9-(3-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)-5-oxo-2-quinolin-3-ylnonanoic acid Chemical compound C1=CC=CC2=CC([C@@H](C(O)=O)CCC(=O)CCCCC3=NC=4NCCCC=4C=C3C)=CN=C21 DMHGRCAGNKKTJL-QHCPKHFHSA-N 0.000 claims description 3
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 3
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 3
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• 229960005356 urokinase Drugs 0.000 claims description 3
• DGUILINMWZCQNV-NRFANRHFSA-N (2S)-2-(2-cyclopropylpyrimidin-5-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound OC(=O)[C@@H](CCC(=O)CCCCc1ccc2CCCNc2n1)c1cnc(nc1)C1CC1 DGUILINMWZCQNV-NRFANRHFSA-N 0.000 claims description 2
• LZQMLZXBYVIKNA-IBGZPJMESA-N (2S)-5-oxo-2-pyrimidin-5-yl-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound OC(=O)[C@@H](CCC(=O)CCCCc1ccc2CCCNc2n1)c1cncnc1 LZQMLZXBYVIKNA-IBGZPJMESA-N 0.000 claims description 2
• CBEYPRXKRIRFIJ-HXUWFJFHSA-N (2r)-2-(2-methylpyrimidin-5-yl)-7-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=NC(C)=NC=C1[C@H](C(O)=O)CCCCC(=O)CCC1=CC=C(CCCN2)C2=N1 CBEYPRXKRIRFIJ-HXUWFJFHSA-N 0.000 claims description 2
• LUCRVWWAYGIHAB-LJQANCHMSA-N (2r)-2-(5-methylpyrazin-2-yl)-5-oxo-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1=NC(C)=CN=C1[C@H](C(O)=O)CCC(=O)CCCCC1=CC=C(CCCN2)C2=N1 LUCRVWWAYGIHAB-LJQANCHMSA-N 0.000 claims description 2
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