BR112020026278A2 - Compostos de aminoácidos com ligantes não ramificados e métodos de uso - Google Patents

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Publication number

BR112020026278A2

BR112020026278A2 BR112020026278-1A BR112020026278A BR112020026278A2 BR 112020026278 A2 BR112020026278 A2 BR 112020026278A2 BR 112020026278 A BR112020026278 A BR 112020026278A BR 112020026278 A2 BR112020026278 A2 BR 112020026278A2

Authority

BR

Brazil

Prior art keywords

tetrahydro

naphthyridin

fact

salt

nonanoic

Prior art date

2018-06-27

Links

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• -1 AMINO ACIDS COMPOUNDS Chemical class 0.000 title claims description 671
• 238000000034 method Methods 0.000 title claims description 310
• 239000011230 binding agent Substances 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 578
• 150000003839 salts Chemical class 0.000 claims abstract description 228
• 102000006495 integrins Human genes 0.000 claims abstract description 113
• 108010044426 integrins Proteins 0.000 claims abstract description 113
• 206010016654 Fibrosis Diseases 0.000 claims abstract description 29
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 27
• 230000004761 fibrosis Effects 0.000 claims abstract description 26
• 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims abstract description 16
• 208000036971 interstitial lung disease 2 Diseases 0.000 claims abstract description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 207
• 229910052805 deuterium Inorganic materials 0.000 claims description 169
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 166
• 239000002253 acid Substances 0.000 claims description 135
• 229910052736 halogen Inorganic materials 0.000 claims description 126
• 150000002367 halogens Chemical class 0.000 claims description 126
• 125000000623 heterocyclic group Chemical group 0.000 claims description 100
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 84
• 229910052739 hydrogen Inorganic materials 0.000 claims description 81
• 125000003118 aryl group Chemical group 0.000 claims description 80
• 239000001257 hydrogen Substances 0.000 claims description 78
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 74
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 73
• 201000010099 disease Diseases 0.000 claims description 71
• 125000004043 oxo group Chemical group O=* 0.000 claims description 64
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 59
• 230000003176 fibrotic effect Effects 0.000 claims description 55
• FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 50
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 49
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 48
• 125000001072 heteroaryl group Chemical group 0.000 claims description 44
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
• 150000002431 hydrogen Chemical class 0.000 claims description 39
• 229910052760 oxygen Inorganic materials 0.000 claims description 39
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
• 125000000304 alkynyl group Chemical group 0.000 claims description 38
• 239000000126 substance Substances 0.000 claims description 36
• 125000003342 alkenyl group Chemical group 0.000 claims description 34
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 31
• 229910052799 carbon Inorganic materials 0.000 claims description 30
• 229910052757 nitrogen Inorganic materials 0.000 claims description 28
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 27
• 125000004429 atom Chemical group 0.000 claims description 24
• 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 20
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 19
• 210000001519 tissue Anatomy 0.000 claims description 18
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
• ZCZVGQCBSJLDDS-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,8-naphthyridine Chemical compound C1=CC=C2CCCNC2=N1 ZCZVGQCBSJLDDS-UHFFFAOYSA-N 0.000 claims description 14
• 229940079593 drug Drugs 0.000 claims description 14
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 13
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 13
• 230000002401 inhibitory effect Effects 0.000 claims description 13
• 210000004072 lung Anatomy 0.000 claims description 12
• 208000010157 sclerosing cholangitis Diseases 0.000 claims description 12
• 210000004027 cell Anatomy 0.000 claims description 11
• 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
• 206010008609 Cholangitis sclerosing Diseases 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 238000004770 highest occupied molecular orbital Methods 0.000 claims description 10
• 201000000742 primary sclerosing cholangitis Diseases 0.000 claims description 10
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
• 206010039710 Scleroderma Diseases 0.000 claims description 9
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
• 239000003937 drug carrier Substances 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 9
• 230000004913 activation Effects 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 8
• 208000005069 pulmonary fibrosis Diseases 0.000 claims description 8
• 101000635938 Homo sapiens Transforming growth factor beta-1 proprotein Proteins 0.000 claims description 7
• 102100030742 Transforming growth factor beta-1 proprotein Human genes 0.000 claims description 7
• 125000002393 azetidinyl group Chemical group 0.000 claims description 7
• 208000020832 chronic kidney disease Diseases 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 230000002496 gastric effect Effects 0.000 claims description 7
• 230000005764 inhibitory process Effects 0.000 claims description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• 201000002793 renal fibrosis Diseases 0.000 claims description 7
• 208000011231 Crohn disease Diseases 0.000 claims description 6
• 230000009787 cardiac fibrosis Effects 0.000 claims description 6
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 6
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 claims description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 210000000013 bile duct Anatomy 0.000 claims description 5
• 230000000694 effects Effects 0.000 claims description 5
• 239000011737 fluorine Substances 0.000 claims description 5
• 125000002757 morpholinyl group Chemical group 0.000 claims description 5
• 206010004664 Biliary fibrosis Diseases 0.000 claims description 4
• 208000029523 Interstitial Lung disease Diseases 0.000 claims description 4
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
• 206010050207 Skin fibrosis Diseases 0.000 claims description 4
• 150000001413 amino acids Chemical class 0.000 claims description 4
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
• UQFQONCQIQEYPJ-UHFFFAOYSA-N N-methylpyrazole Chemical compound CN1C=CC=N1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 claims description 3
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 3
• 201000005206 focal segmental glomerulosclerosis Diseases 0.000 claims description 3
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
• UOFVEPKQZXHQSB-UHFFFAOYSA-N 2,2,6,6-tetramethyloxane-4-carboxylic acid Chemical compound CC1(C)CC(C(O)=O)CC(C)(C)O1 UOFVEPKQZXHQSB-UHFFFAOYSA-N 0.000 claims description 2
• JICIAMVTQMKDJR-UHFFFAOYSA-N 2-(1-phenylethylamino)-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1(=CC=CC=C1)C(C)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 JICIAMVTQMKDJR-UHFFFAOYSA-N 0.000 claims description 2
• OBDVYLFPUNJSTA-UHFFFAOYSA-N 2-(3,4-dihydro-2H-chromene-4-carbonylamino)-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound O1CCC(C2=CC=CC=C12)C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 OBDVYLFPUNJSTA-UHFFFAOYSA-N 0.000 claims description 2
• GKKYLQBGYKTTIE-UHFFFAOYSA-N 2-(3-sulfamoylpropanoylamino)-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound S(N)(=O)(=O)CCC(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 GKKYLQBGYKTTIE-UHFFFAOYSA-N 0.000 claims description 2
• YFLNAHYGMRZVMD-UHFFFAOYSA-N 2-(4-methoxybutanoylamino)-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound COCCCC(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 YFLNAHYGMRZVMD-UHFFFAOYSA-N 0.000 claims description 2
• BIROPQXKMPFDJJ-UHFFFAOYSA-N 2-(4-methylsulfonylbutanoylamino)-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound CS(=O)(=O)CCCC(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 BIROPQXKMPFDJJ-UHFFFAOYSA-N 0.000 claims description 2
• WMKWZJXOOFIEDW-UHFFFAOYSA-N 2-(bicyclo[1.1.1]pentane-1-carbonylamino)-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C12(CC(C1)C2)C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 WMKWZJXOOFIEDW-UHFFFAOYSA-N 0.000 claims description 2
• LHLIPBQGKAYXRJ-UHFFFAOYSA-N 2-(oxolane-3-carbonylamino)-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound N1=C(C=CC=2CCCNC1=2)CCCCCCCC(C(=O)O)NC(=O)C1COCC1 LHLIPBQGKAYXRJ-UHFFFAOYSA-N 0.000 claims description 2
• PWPUVAKXIIRABO-UHFFFAOYSA-N 2-(piperidine-4-carbonylamino)-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound N1CCC(CC1)C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 PWPUVAKXIIRABO-UHFFFAOYSA-N 0.000 claims description 2
• YQCGDOVKSSDLIW-UHFFFAOYSA-N 2-(pyrimidin-4-ylamino)-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound N1=CN=C(C=C1)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 YQCGDOVKSSDLIW-UHFFFAOYSA-N 0.000 claims description 2
• KCWCIOBTIIKPIE-UHFFFAOYSA-N 2-(quinazolin-4-ylamino)-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound N1=CN=C(C2=CC=CC=C12)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 KCWCIOBTIIKPIE-UHFFFAOYSA-N 0.000 claims description 2
• KVAZBXJFRMLHFH-UHFFFAOYSA-N 2-[(1-methylcyclohexanecarbonyl)amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound CC1(CCCCC1)C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 KVAZBXJFRMLHFH-UHFFFAOYSA-N 0.000 claims description 2
• CWZXCJPGXXAJEK-UHFFFAOYSA-N 2-[(1-methylsulfonylpiperidine-3-carbonyl)amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound CS(=O)(=O)N1CC(CCC1)C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 CWZXCJPGXXAJEK-UHFFFAOYSA-N 0.000 claims description 2
• ROWIFPJTKWXFSM-UHFFFAOYSA-N 2-[(1-methylsulfonylpiperidine-4-carbonyl)amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound CS(=O)(=O)N1CCC(CC1)C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 ROWIFPJTKWXFSM-UHFFFAOYSA-N 0.000 claims description 2
• VHKGGHPBNADPGL-UHFFFAOYSA-N 2-[(3,5-dimethylmorpholine-4-carbonyl)amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound CC1N(C(COC1)C)C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 VHKGGHPBNADPGL-UHFFFAOYSA-N 0.000 claims description 2
• BKZLIIAXSCVOMU-UHFFFAOYSA-N 2-[(4-acetamido-1-methylcyclohexanecarbonyl)amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C(C)(=O)NC1CCC(CC1)(C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1)C BKZLIIAXSCVOMU-UHFFFAOYSA-N 0.000 claims description 2
• ZEUUNQVLNYMPPO-UHFFFAOYSA-N 2-[(4-aminobicyclo[2.2.2]octane-1-carbonyl)amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound NC12CCC(CC1)(CC2)C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 ZEUUNQVLNYMPPO-UHFFFAOYSA-N 0.000 claims description 2
• VZXXZYFBYQKVEL-UHFFFAOYSA-N 2-[(4-fluorooxane-4-carbonyl)amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound FC1(CCOCC1)C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 VZXXZYFBYQKVEL-UHFFFAOYSA-N 0.000 claims description 2
• NXBNMZICIDXCEF-UHFFFAOYSA-N 2-[(4-methylpiperidine-4-carbonyl)amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound CC1(CCNCC1)C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 NXBNMZICIDXCEF-UHFFFAOYSA-N 0.000 claims description 2
• JZEGLQYAMHDSGK-UHFFFAOYSA-N 2-[(4-phenyloxane-4-carbonyl)amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C1(=CC=CC=C1)C1(CCOCC1)C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 JZEGLQYAMHDSGK-UHFFFAOYSA-N 0.000 claims description 2
• BAZOJJIFIMYMKJ-UHFFFAOYSA-N 2-[(5-pyridin-3-ylpyrimidin-2-yl)amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound N1=CC(=CC=C1)C=1C=NC(=NC=1)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 BAZOJJIFIMYMKJ-UHFFFAOYSA-N 0.000 claims description 2
• OHSNQOPSQVEFJD-UHFFFAOYSA-N 2-[(6-morpholin-4-ylpyrimidin-4-yl)amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound O1CCN(CC1)C1=CC(=NC=N1)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 OHSNQOPSQVEFJD-UHFFFAOYSA-N 0.000 claims description 2
• DPENEHPLPXRPCL-UHFFFAOYSA-N 2-[(6-propylsulfonylpyrimidin-4-yl)amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C(CC)S(=O)(=O)C1=CC(=NC=N1)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 DPENEHPLPXRPCL-UHFFFAOYSA-N 0.000 claims description 2
• HATSKYWSXLAZAG-UHFFFAOYSA-N 2-[(6-pyrrolidin-1-ylpyrimidin-4-yl)amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound N1(CCCC1)C1=CC(=NC=N1)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 HATSKYWSXLAZAG-UHFFFAOYSA-N 0.000 claims description 2
• VNGGDIGYGJIBPR-UHFFFAOYSA-N 2-[3-(methanesulfonamido)propanoylamino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound CS(=O)(=O)NCCC(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 VNGGDIGYGJIBPR-UHFFFAOYSA-N 0.000 claims description 2
• YFSCWAATGZJYQD-UHFFFAOYSA-N 2-[[1-(2,2-dimethylpropanoyl)-4-methylpiperidine-4-carbonyl]amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound CC1(CCN(CC1)C(C(C)(C)C)=O)C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 YFSCWAATGZJYQD-UHFFFAOYSA-N 0.000 claims description 2
• RIXQVQIKEVOQDZ-UHFFFAOYSA-N 2-[[1-(3-fluoropropyl)-4-methylpiperidine-4-carbonyl]amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound FCCCN1CCC(CC1)(C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1)C RIXQVQIKEVOQDZ-UHFFFAOYSA-N 0.000 claims description 2
• QJVYDNANYCGHDE-UHFFFAOYSA-N 2-[[1-(3-methoxypropanoyl)-3-methylpyrrolidine-2-carbonyl]amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound COCCC(=O)N1C(C(CC1)C)C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 QJVYDNANYCGHDE-UHFFFAOYSA-N 0.000 claims description 2
• LGKQDOJKWLHMFB-UHFFFAOYSA-N 2-[[1-(3-methoxypropanoyl)piperidine-3-carbonyl]amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound COCCC(=O)N1CC(CCC1)C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 LGKQDOJKWLHMFB-UHFFFAOYSA-N 0.000 claims description 2
• BSBLJZRWNSXYFU-UHFFFAOYSA-N 2-[[1-(pyridin-3-ylmethyl)pyrrolidine-2-carbonyl]amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound N1=CC(=CC=C1)CN1C(CCC1)C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 BSBLJZRWNSXYFU-UHFFFAOYSA-N 0.000 claims description 2
• ZPRJIPUXQMNOLL-UHFFFAOYSA-N 2-[[1-(pyrimidin-4-ylmethyl)pyrrolidine-2-carbonyl]amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound N1=CN=C(C=C1)CN1C(CCC1)C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 ZPRJIPUXQMNOLL-UHFFFAOYSA-N 0.000 claims description 2
• SAPOFSHGUQYZTD-UHFFFAOYSA-N 2-[[1-[(2-methylpropan-2-yl)oxycarbonyl]azetidin-3-yl]oxycarbonylamino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C(C)(C)(C)OC(=O)N1CC(C1)OC(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 SAPOFSHGUQYZTD-UHFFFAOYSA-N 0.000 claims description 2
• DVXFNFLXNPFQNK-UHFFFAOYSA-N 2-[[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidine-2-carbonyl]amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C(C)(C)(C)OC(=O)N1C(CCCC1)C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 DVXFNFLXNPFQNK-UHFFFAOYSA-N 0.000 claims description 2
• BEGQIYIHMYFSMA-UHFFFAOYSA-N 2-[[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidine-4-carbonyl]amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound C(C)(C)(C)OC(=O)N1CCC(CC1)C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 BEGQIYIHMYFSMA-UHFFFAOYSA-N 0.000 claims description 2
• BJHIOXCNDUOXSU-UHFFFAOYSA-N 2-[[2-(2-chlorophenyl)acetyl]amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound ClC1=C(C=CC=C1)CC(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1 BJHIOXCNDUOXSU-UHFFFAOYSA-N 0.000 claims description 2
• XFOMVDMKGOQGDK-UHFFFAOYSA-N 2-[[3-(benzenesulfonyl)-5,5-dimethyl-1,3-thiazolidine-4-carbonyl]amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound CC1(C(N(CS1)S(=O)(=O)C1=CC=CC=C1)C(=O)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1)C XFOMVDMKGOQGDK-UHFFFAOYSA-N 0.000 claims description 2
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• OBRDCXMEECNQCE-UHFFFAOYSA-N 2-[[6-(dimethylamino)pyrimidin-4-yl]amino]-9-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)nonanoic acid Chemical compound CN(C1=CC(=NC=N1)NC(C(=O)O)CCCCCCCC1=NC=2NCCCC=2C=C1)C OBRDCXMEECNQCE-UHFFFAOYSA-N 0.000 claims description 2
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