JP2011514893A - ファルネシルピロホスフェートシンターゼの阻害剤としてのキノリン - Google Patents

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Publication number

JP2011514893A

JP2011514893A JP2010548111A JP2010548111A JP2011514893A JP 2011514893 A JP2011514893 A JP 2011514893A JP 2010548111 A JP2010548111 A JP 2010548111A JP 2010548111 A JP2010548111 A JP 2010548111A JP 2011514893 A JP2011514893 A JP 2011514893A

Authority

JP

Japan

Prior art keywords

naphthalen

quinolin

amino

formula

phosphonic acid

Prior art date

2008-02-28

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.)

Pending

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• 102100035111 Farnesyl pyrophosphate synthase Human genes 0.000 title abstract description 49
• 101710125754 Farnesyl pyrophosphate synthase Proteins 0.000 title abstract description 49
• 239000003112 inhibitor Substances 0.000 title description 22
• 150000003248 quinolines Chemical class 0.000 title description 3
• 229940111121 antirheumatic drug quinolines Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 418
• 238000011282 treatment Methods 0.000 claims abstract description 76
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 63
• 238000000034 method Methods 0.000 claims abstract description 61
• 201000010099 disease Diseases 0.000 claims abstract description 51
• 230000008569 process Effects 0.000 claims abstract description 9
• -1 hydroxy, amino, N-substituted amino Chemical group 0.000 claims description 183
• 229910052739 hydrogen Inorganic materials 0.000 claims description 90
• 150000003839 salts Chemical class 0.000 claims description 81
• 125000001424 substituent group Chemical group 0.000 claims description 77
• 125000000217 alkyl group Chemical group 0.000 claims description 65
• 239000001257 hydrogen Substances 0.000 claims description 52
• 238000006243 chemical reaction Methods 0.000 claims description 41
• 229910052799 carbon Inorganic materials 0.000 claims description 38
• 229910052757 nitrogen Inorganic materials 0.000 claims description 36
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 35
• 125000000623 heterocyclic group Chemical group 0.000 claims description 34
• 150000002431 hydrogen Chemical class 0.000 claims description 29
• 239000008194 pharmaceutical composition Substances 0.000 claims description 26
• 230000001419 dependent effect Effects 0.000 claims description 25
• 150000002148 esters Chemical class 0.000 claims description 25
• 125000003545 alkoxy group Chemical group 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
• 125000003118 aryl group Chemical group 0.000 claims description 22
• 239000002253 acid Substances 0.000 claims description 21
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 239000003054 catalyst Substances 0.000 claims description 20
• 150000002367 halogens Chemical class 0.000 claims description 20
• 238000004519 manufacturing process Methods 0.000 claims description 19
• 125000004043 oxo group Chemical group O=* 0.000 claims description 19
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 17
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 14
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 12
• 125000005843 halogen group Chemical group 0.000 claims description 12
• 238000002360 preparation method Methods 0.000 claims description 12
• 125000003107 substituted aryl group Chemical group 0.000 claims description 12
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 11
• 239000003085 diluting agent Substances 0.000 claims description 11
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
• 239000003937 drug carrier Substances 0.000 claims description 10
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 10
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
• 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 claims description 9
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
• 125000001589 carboacyl group Chemical group 0.000 claims description 9
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 9
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 8
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000001246 bromo group Chemical group Br* 0.000 claims description 7
• 150000001721 carbon Chemical group 0.000 claims description 7
• XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 claims description 6
• 125000002252 acyl group Chemical group 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 6
• 238000002156 mixing Methods 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 125000006413 ring segment Chemical group 0.000 claims description 6
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
• 239000012190 activator Substances 0.000 claims description 5
• 239000004480 active ingredient Substances 0.000 claims description 5
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 5
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 5
• 125000002346 iodo group Chemical group I* 0.000 claims description 5
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
• 239000000126 substance Substances 0.000 claims description 5
• 238000006467 substitution reaction Methods 0.000 claims description 5
• 229930192474 thiophene Natural products 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 4
• KCKZIWSINLBROE-UHFFFAOYSA-N 3,4-dihydro-1h-naphthalen-2-one Chemical compound C1=CC=C2CC(=O)CCC2=C1 KCKZIWSINLBROE-UHFFFAOYSA-N 0.000 claims description 4
• QMAYJELNBDAEMC-UHFFFAOYSA-N 8-naphthalen-1-ylquinoline-2-carboxylic acid Chemical compound C1=CC=C2C(C3=CC=CC4=CC=C(N=C43)C(=O)O)=CC=CC2=C1 QMAYJELNBDAEMC-UHFFFAOYSA-N 0.000 claims description 4
• 125000004423 acyloxy group Chemical group 0.000 claims description 4
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
• 125000001188 haloalkyl group Chemical group 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 4
• VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 claims description 4
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 4
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• PJZKWPSCTNBEFJ-UHFFFAOYSA-N 6-amino-5-ethoxy-8-naphthalen-1-ylquinoline-2-carboxylic acid Chemical compound C12=NC(C(O)=O)=CC=C2C(OCC)=C(N)C=C1C1=CC=CC2=CC=CC=C12 PJZKWPSCTNBEFJ-UHFFFAOYSA-N 0.000 claims description 3
• JVXSIISWWVEGMB-UHFFFAOYSA-N 8-naphthalen-1-yl-2-(2h-tetrazol-5-yl)-6-thiophen-2-ylquinoline Chemical compound C1=CSC(C=2C=C3C=CC(=NC3=C(C=3C4=CC=CC=C4C=CC=3)C=2)C2=NNN=N2)=C1 JVXSIISWWVEGMB-UHFFFAOYSA-N 0.000 claims description 3
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
• XJJOJKMIJSBTHY-ZHACJKMWSA-N [(e)-2-(8-naphthalen-1-yl-6-nitroquinolin-2-yl)ethenyl]phosphonic acid Chemical compound C1=CC=C2C(C3=CC(=CC4=CC=C(N=C43)/C=C/P(O)(=O)O)[N+]([O-])=O)=CC=CC2=C1 XJJOJKMIJSBTHY-ZHACJKMWSA-N 0.000 claims description 3
• 125000001072 heteroaryl group Chemical group 0.000 claims description 3
• VJDRWHINXZXKMT-UHFFFAOYSA-N methyl 2-[(2-methylpropan-2-yl)oxycarbonylsulfamoylamino]-3-[(8-naphthalen-1-ylquinoline-2-carbonyl)amino]propanoate Chemical compound C1=CC=C2C(C3=CC=CC4=CC=C(N=C43)C(=O)NCC(C(=O)OC)NS(=O)(=O)NC(=O)OC(C)(C)C)=CC=CC2=C1 VJDRWHINXZXKMT-UHFFFAOYSA-N 0.000 claims description 3
• YKFGNNONPWRXJA-UHFFFAOYSA-N methyl 3-[(8-naphthalen-1-ylquinoline-2-carbonyl)amino]-2-(sulfamoylamino)propanoate Chemical compound C1=CC=C2C(C3=CC=CC4=CC=C(N=C43)C(=O)NCC(C(=O)OC)NS(N)(=O)=O)=CC=CC2=C1 YKFGNNONPWRXJA-UHFFFAOYSA-N 0.000 claims description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
• 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 239000011593 sulfur Substances 0.000 claims description 3
• AEEMWRLWXPTKQF-UHFFFAOYSA-N (6-amino-8-naphthalen-1-ylquinolin-2-yl)phosphonic acid Chemical compound N1=C(P(O)(O)=O)C=CC2=CC(N)=CC(C=3C4=CC=CC=C4C=CC=3)=C21 AEEMWRLWXPTKQF-UHFFFAOYSA-N 0.000 claims description 2
• BFHMEXQKIZPMEU-UHFFFAOYSA-N (8-naphthalen-1-yl-6-nitroquinolin-2-yl)phosphonic acid Chemical compound C1=CC=C2C(C3=CC(=CC4=CC=C(N=C43)P(O)(=O)O)[N+]([O-])=O)=CC=CC2=C1 BFHMEXQKIZPMEU-UHFFFAOYSA-N 0.000 claims description 2
• DVGROFMXSDCKET-UHFFFAOYSA-N (8-naphthalen-1-yl-6-thiophen-2-ylquinolin-2-yl)phosphonic acid Chemical compound C1=C(C=2C3=CC=CC=C3C=CC=2)C2=NC(P(O)(=O)O)=CC=C2C=C1C1=CC=CS1 DVGROFMXSDCKET-UHFFFAOYSA-N 0.000 claims description 2
• CIZJXTCJOYALTD-UHFFFAOYSA-N (8-naphthalen-1-ylquinolin-2-yl)methylphosphonic acid Chemical compound C1=CC=C2C(C3=CC=CC4=CC=C(N=C43)CP(O)(=O)O)=CC=CC2=C1 CIZJXTCJOYALTD-UHFFFAOYSA-N 0.000 claims description 2
• PIHNCPKKZDMBQU-UHFFFAOYSA-N (8-naphthalen-1-ylquinolin-2-yl)phosphonic acid Chemical compound C1=CC=C2C(C3=CC=CC4=CC=C(N=C43)P(O)(=O)O)=CC=CC2=C1 PIHNCPKKZDMBQU-UHFFFAOYSA-N 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 2
• AJOJYBPWVCYZEO-UHFFFAOYSA-N 2-(1-methyltetrazol-5-yl)-8-naphthalen-1-yl-6-thiophen-2-ylquinoline Chemical compound CN1N=NN=C1C1=CC=C(C=C(C=C2C=3C4=CC=CC=C4C=CC=3)C=3SC=CC=3)C2=N1 AJOJYBPWVCYZEO-UHFFFAOYSA-N 0.000 claims description 2
• DJFCUWXVSXDRNS-UHFFFAOYSA-N 2-(2-methyltetrazol-5-yl)-8-naphthalen-1-yl-6-thiophen-2-ylquinoline Chemical compound CN1N=NC(C=2N=C3C(C=4C5=CC=CC=C5C=CC=4)=CC(=CC3=CC=2)C=2SC=CC=2)=N1 DJFCUWXVSXDRNS-UHFFFAOYSA-N 0.000 claims description 2
• GUUBOAPWDBPHPL-UHFFFAOYSA-N 3-[(8-naphthalen-1-ylquinoline-2-carbonyl)amino]-2-(sulfamoylamino)propanoic acid Chemical compound C1=CC=C2C(C3=CC=CC4=CC=C(N=C43)C(=O)NCC(NS(=O)(=O)N)C(O)=O)=CC=CC2=C1 GUUBOAPWDBPHPL-UHFFFAOYSA-N 0.000 claims description 2
• PJVKVUKOHHEMBQ-UHFFFAOYSA-N 6-(ethoxycarbonylamino)-8-naphthalen-1-ylquinoline-2-carboxylic acid Chemical compound N1=C(C(O)=O)C=CC2=CC(NC(=O)OCC)=CC(C=3C4=CC=CC=C4C=CC=3)=C21 PJVKVUKOHHEMBQ-UHFFFAOYSA-N 0.000 claims description 2
• XQSFNIQCLKPWQI-UHFFFAOYSA-N 6-amino-8-naphthalen-1-ylquinoline-2-carboxylic acid Chemical compound N1=C(C(O)=O)C=CC2=CC(N)=CC(C=3C4=CC=CC=C4C=CC=3)=C21 XQSFNIQCLKPWQI-UHFFFAOYSA-N 0.000 claims description 2
• KFQVXNCMDUAGPT-UHFFFAOYSA-N 8-(5-aminonaphthalen-1-yl)quinoline-2-carboxylic acid Chemical compound C1=C(C(O)=O)N=C2C(C3=C4C=CC=C(C4=CC=C3)N)=CC=CC2=C1 KFQVXNCMDUAGPT-UHFFFAOYSA-N 0.000 claims description 2
• IPDDLBRKILFKMY-UHFFFAOYSA-N 8-(5-methylnaphthalen-1-yl)quinoline-2-carboxylic acid Chemical compound C1=C(C(O)=O)N=C2C(C3=C4C=CC=C(C4=CC=C3)C)=CC=CC2=C1 IPDDLBRKILFKMY-UHFFFAOYSA-N 0.000 claims description 2
• MTUAVLUIGJMCMQ-UHFFFAOYSA-N 8-[5-(hydroxymethyl)naphthalen-1-yl]quinoline-2-carboxylic acid Chemical compound C1=C(C(O)=O)N=C2C(C3=C4C=CC=C(C4=CC=C3)CO)=CC=CC2=C1 MTUAVLUIGJMCMQ-UHFFFAOYSA-N 0.000 claims description 2
• ZYDRSSKOQAPSNX-UHFFFAOYSA-N 8-naphthalen-1-yl-6-thiophen-3-ylquinoline-2-carboxylic acid Chemical compound C1=C(C=2C3=CC=CC=C3C=CC=2)C2=NC(C(=O)O)=CC=C2C=C1C=1C=CSC=1 ZYDRSSKOQAPSNX-UHFFFAOYSA-N 0.000 claims description 2
• IGZVTROBKAZILD-UHFFFAOYSA-N [(6-amino-8-naphthalen-1-ylquinolin-2-yl)amino]methylphosphonic acid Chemical compound N1=C(NCP(O)(O)=O)C=CC2=CC(N)=CC(C=3C4=CC=CC=C4C=CC=3)=C21 IGZVTROBKAZILD-UHFFFAOYSA-N 0.000 claims description 2
• LXCZHIFHGACDOB-UHFFFAOYSA-N [(6-iodo-8-naphthalen-1-ylquinolin-2-yl)amino]methylphosphonic acid Chemical compound C1=CC=C2C(C3=CC(I)=CC4=CC=C(N=C43)NCP(O)(=O)O)=CC=CC2=C1 LXCZHIFHGACDOB-UHFFFAOYSA-N 0.000 claims description 2
• FMILHYNQBMROQY-UHFFFAOYSA-N [(8-naphthalen-1-yl-6-nitroquinolin-2-yl)amino]methylphosphonic acid Chemical compound C1=CC=C2C(C3=CC(=CC4=CC=C(N=C43)NCP(O)(=O)O)[N+]([O-])=O)=CC=CC2=C1 FMILHYNQBMROQY-UHFFFAOYSA-N 0.000 claims description 2
• HTYUXNZMWIOOSS-UHFFFAOYSA-N [(8-naphthalen-1-yl-6-pyridin-3-ylquinolin-2-yl)amino]methylphosphonic acid Chemical compound C1=C(C=2C3=CC=CC=C3C=CC=2)C2=NC(NCP(O)(=O)O)=CC=C2C=C1C1=CC=CN=C1 HTYUXNZMWIOOSS-UHFFFAOYSA-N 0.000 claims description 2
• VJGUWLBDNRYANG-UHFFFAOYSA-N [(8-naphthalen-1-ylquinolin-2-yl)amino]methylphosphonic acid Chemical compound C1=CC=C2C(C3=CC=CC4=CC=C(N=C43)NCP(O)(=O)O)=CC=CC2=C1 VJGUWLBDNRYANG-UHFFFAOYSA-N 0.000 claims description 2
• DFJHEAAUBDRUFT-UHFFFAOYSA-N [(8-naphthalen-1-ylquinolin-2-yl)methylamino]methylphosphonic acid Chemical compound C1=CC=C2C(C3=CC=CC4=CC=C(N=C43)CNCP(O)(=O)O)=CC=CC2=C1 DFJHEAAUBDRUFT-UHFFFAOYSA-N 0.000 claims description 2
• LJNGARCVBHPRBS-UHFFFAOYSA-N [(8-naphthalen-1-ylquinoline-2-carbonyl)amino]methylphosphonic acid Chemical compound C1=CC=C2C(C3=CC=CC4=CC=C(N=C43)C(=O)NCP(O)(=O)O)=CC=CC2=C1 LJNGARCVBHPRBS-UHFFFAOYSA-N 0.000 claims description 2
• RRMXUIAJWTVWRD-ZHACJKMWSA-N [(e)-2-(6-amino-8-naphthalen-1-ylquinolin-2-yl)ethenyl]phosphonic acid Chemical compound N1=C(\C=C\P(O)(O)=O)C=CC2=CC(N)=CC(C=3C4=CC=CC=C4C=CC=3)=C21 RRMXUIAJWTVWRD-ZHACJKMWSA-N 0.000 claims description 2
• RWXMAPWKGJNKFO-BUHFOSPRSA-N [(e)-2-(8-naphthalen-1-ylquinolin-2-yl)ethenyl]phosphonic acid Chemical compound C1=CC=C2C(C3=CC=CC4=CC=C(N=C43)/C=C/P(O)(=O)O)=CC=CC2=C1 RWXMAPWKGJNKFO-BUHFOSPRSA-N 0.000 claims description 2
• SVHHSVJARFWPGW-VAWYXSNFSA-N [(e)-2-[6-(methanesulfonamido)-8-naphthalen-1-ylquinolin-2-yl]ethenyl]phosphonic acid Chemical compound N1=C(\C=C\P(O)(O)=O)C=CC2=CC(NS(=O)(=O)C)=CC(C=3C4=CC=CC=C4C=CC=3)=C21 SVHHSVJARFWPGW-VAWYXSNFSA-N 0.000 claims description 2
• FJMLVSZMIVBODW-BUHFOSPRSA-N [(e)-2-[6-[(2-amino-3,3-dimethylbutanoyl)amino]-8-naphthalen-1-ylquinolin-2-yl]ethenyl]phosphonic acid Chemical compound N1=C(\C=C\P(O)(O)=O)C=CC2=CC(NC(=O)C(N)C(C)(C)C)=CC(C=3C4=CC=CC=C4C=CC=3)=C21 FJMLVSZMIVBODW-BUHFOSPRSA-N 0.000 claims description 2
• QPJKPQZMYOIBTG-UHFFFAOYSA-N [6-(3-hydroxyphenyl)-8-naphthalen-1-ylquinolin-2-yl]phosphonic acid Chemical compound OC1=CC=CC(C=2C=C3C=CC(=NC3=C(C=3C4=CC=CC=C4C=CC=3)C=2)P(O)(O)=O)=C1 QPJKPQZMYOIBTG-UHFFFAOYSA-N 0.000 claims description 2
• KOPQIYWIJIZHKP-UHFFFAOYSA-N [6-(3-methoxyphenyl)-8-naphthalen-1-ylquinolin-2-yl]phosphonic acid Chemical compound COC1=CC=CC(C=2C=C3C=CC(=NC3=C(C=3C4=CC=CC=C4C=CC=3)C=2)P(O)(O)=O)=C1 KOPQIYWIJIZHKP-UHFFFAOYSA-N 0.000 claims description 2
• NJFSLUZECGNZIW-UHFFFAOYSA-N [6-(6-methoxypyridin-3-yl)-8-naphthalen-1-ylquinolin-2-yl]phosphonic acid Chemical compound C1=NC(OC)=CC=C1C1=CC(C=2C3=CC=CC=C3C=CC=2)=C(N=C(C=C2)P(O)(O)=O)C2=C1 NJFSLUZECGNZIW-UHFFFAOYSA-N 0.000 claims description 2
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