JP2011514893A5 - - Google Patents
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- Publication number
- JP2011514893A5 JP2011514893A5 JP2010548111A JP2010548111A JP2011514893A5 JP 2011514893 A5 JP2011514893 A5 JP 2011514893A5 JP 2010548111 A JP2010548111 A JP 2010548111A JP 2010548111 A JP2010548111 A JP 2010548111A JP 2011514893 A5 JP2011514893 A5 JP 2011514893A5
- Authority
- JP
- Japan
- Prior art keywords
- naphthalen
- quinolin
- amino
- phosphonic acid
- quinoline
- Prior art date
- 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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- -1 hydroxy, amino, N-substituted amino Chemical group 0.000 claims 28
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000001424 substituent group Chemical group 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- HVYWMOMLDIMFJA-DPAQBDIFSA-N (3β)-Cholest-5-en-3-ol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 7
- 239000011780 sodium chloride Substances 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 229940107161 Cholesterol Drugs 0.000 claims 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 239000003085 diluting agent Substances 0.000 claims 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 claims 2
- ZLRFPQPVXRIBCQ-UHFFFAOYSA-N 2-$l^{1}-oxidanyl-2-methylpropane Chemical group CC(C)(C)[O] ZLRFPQPVXRIBCQ-UHFFFAOYSA-N 0.000 claims 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 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 2
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical group C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 claims 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 2
- 210000004369 Blood Anatomy 0.000 claims 2
- 102000009016 Cholera Toxin Human genes 0.000 claims 2
- 108010049048 Cholera Toxin Proteins 0.000 claims 2
- 101710021343 FDPS Proteins 0.000 claims 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N Isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
- FHVZTSKOTAICPP-UHFFFAOYSA-N N-[8-naphthalen-1-yl-2-(2H-tetrazol-5-yl)quinolin-6-yl]acetamide Chemical compound C1=CC2=CC(NC(=O)C)=CC(C=3C4=CC=CC=C4C=CC=3)=C2N=C1C=1N=NNN=1 FHVZTSKOTAICPP-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000004429 atoms Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 230000037348 biosynthesis Effects 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 239000008280 blood Substances 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 235000012000 cholesterol Nutrition 0.000 claims 2
- 230000001419 dependent Effects 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- XARIYYOCIDWMGK-UHFFFAOYSA-N ethyl N-[8-naphthalen-1-yl-2-(2H-tetrazol-5-yl)quinolin-6-yl]carbamate Chemical compound C1=CC2=CC(NC(=O)OCC)=CC(C=3C4=CC=CC=C4C=CC=3)=C2N=C1C=1N=NNN=1 XARIYYOCIDWMGK-UHFFFAOYSA-N 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims 2
- VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 claims 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 2
- 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 2
- 230000002062 proliferating Effects 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2(1H)-one Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 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 1
- JRIXZKNKIKKGBX-UHFFFAOYSA-N (6-iodo-8-naphthalen-1-ylquinolin-2-yl)phosphonic acid Chemical compound C1=CC=C2C(C3=CC(I)=CC4=CC=C(N=C43)P(O)(=O)O)=CC=CC2=C1 JRIXZKNKIKKGBX-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-Tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 claims 1
- QEFQTSJOGQNNHD-UHFFFAOYSA-N 2-(8-naphthalen-1-ylquinolin-2-yl)ethylphosphonic acid Chemical compound C1=CC=C2C(C3=CC=CC4=CC=C(N=C43)CCP(O)(=O)O)=CC=CC2=C1 QEFQTSJOGQNNHD-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- KCKZIWSINLBROE-UHFFFAOYSA-N 3,4-dihydro-1H-naphthalen-2-one Chemical compound C1=CC=C2CC(=O)CCC2=C1 KCKZIWSINLBROE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- YOISSNNPGKCDHH-UHFFFAOYSA-N 5-ethoxy-6-iodo-8-naphthalen-1-ylquinoline-2-carboxylic acid Chemical compound C12=NC(C(O)=O)=CC=C2C(OCC)=C(I)C=C1C1=CC=CC2=CC=CC=C12 YOISSNNPGKCDHH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- LASMXCXZNGKTJK-UHFFFAOYSA-N 6-chloro-8-naphthalen-1-ylquinoline-2-carboxylic acid Chemical compound C1=CC=C2C(C3=CC(Cl)=CC4=CC=C(N=C43)C(=O)O)=CC=CC2=C1 LASMXCXZNGKTJK-UHFFFAOYSA-N 0.000 claims 1
- UHUACSTYMGXAOH-UHFFFAOYSA-N 6-iodo-8-naphthalen-1-ylquinoline-2-carboxylic acid Chemical compound C1=CC=C2C(C3=CC(I)=CC4=CC=C(N=C43)C(=O)O)=CC=CC2=C1 UHUACSTYMGXAOH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- RSHSGQQZDAKAOC-UHFFFAOYSA-N 8-naphthalen-1-yl-6-(1H-pyrrol-2-yl)quinoline-2-carboxylic acid Chemical compound C1=C(C=2C3=CC=CC=C3C=CC=2)C2=NC(C(=O)O)=CC=C2C=C1C1=CC=CN1 RSHSGQQZDAKAOC-UHFFFAOYSA-N 0.000 claims 1
- BADLWUYTNYGCSG-UHFFFAOYSA-N 8-naphthalen-1-yl-6-thiophen-2-ylquinoline-2-carboxylic acid Chemical compound C1=C(C=2C3=CC=CC=C3C=CC=2)C2=NC(C(=O)O)=CC=C2C=C1C1=CC=CS1 BADLWUYTNYGCSG-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N OBO Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
- 241000233855 Orchidaceae Species 0.000 claims 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N Tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 1
- 241001135917 Vitellaria paradoxa Species 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- YXNCZDLAUQFYPO-VAWYXSNFSA-N [(E)-2-(6-acetamido-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)=CC(C=3C4=CC=CC=C4C=CC=3)=C21 YXNCZDLAUQFYPO-VAWYXSNFSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- SVYATFPZDCUKMZ-VAWYXSNFSA-N [(E)-2-[6-(methoxycarbonylamino)-8-naphthalen-1-ylquinolin-2-yl]ethenyl]phosphonic acid Chemical compound N1=C(\C=C\P(O)(O)=O)C=CC2=CC(NC(=O)OC)=CC(C=3C4=CC=CC=C4C=CC=3)=C21 SVYATFPZDCUKMZ-VAWYXSNFSA-N 0.000 claims 1
- 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 1
- VUOOLCHLRRULRW-OUKQBFOZSA-N [(E)-2-[6-[bis(methylsulfonyl)amino]-8-naphthalen-1-ylquinolin-2-yl]ethenyl]phosphonic acid Chemical compound N1=C(\C=C\P(O)(O)=O)C=CC2=CC(N(S(=O)(=O)C)S(C)(=O)=O)=CC(C=3C4=CC=CC=C4C=CC=3)=C21 VUOOLCHLRRULRW-OUKQBFOZSA-N 0.000 claims 1
- KREFDZZGJVWZPZ-UHFFFAOYSA-N [6-(1H-indol-2-yl)-8-naphthalen-1-ylquinolin-2-yl]phosphonic acid Chemical compound C1=CC=C2NC(C3=CC4=CC=C(N=C4C(C=4C5=CC=CC=C5C=CC=4)=C3)P(O)(=O)O)=CC2=C1 KREFDZZGJVWZPZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- UBMPYQRMKCNIEV-UHFFFAOYSA-N [6-[1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrol-2-yl]-8-naphthalen-1-ylquinolin-2-yl]phosphonic acid Chemical compound CC(C)(C)OC(=O)N1C=CC=C1C1=CC(C=2C3=CC=CC=C3C=CC=2)=C(N=C(C=C2)P(O)(O)=O)C2=C1 UBMPYQRMKCNIEV-UHFFFAOYSA-N 0.000 claims 1
- FLUITQDECLFMSB-UHFFFAOYSA-N [8-naphthalen-1-yl-6-(1H-pyrrol-2-yl)quinolin-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=CN1 FLUITQDECLFMSB-UHFFFAOYSA-N 0.000 claims 1
- TVZSJHZLCGEPMV-UHFFFAOYSA-N [8-naphthalen-1-yl-6-(1H-pyrrol-3-yl)quinolin-2-yl]phosphonic acid Chemical compound C1=C(C=2C3=CC=CC=C3C=CC=2)C2=NC(P(O)(=O)O)=CC=C2C=C1C=1C=CNC=1 TVZSJHZLCGEPMV-UHFFFAOYSA-N 0.000 claims 1
- OPLDWQUCYFHJLJ-UHFFFAOYSA-N [8-naphthalen-1-yl-6-(6-oxo-1H-pyridin-3-yl)quinolin-2-yl]phosphonic acid Chemical compound C1=NC(O)=CC=C1C1=CC(C=2C3=CC=CC=C3C=CC=2)=C(N=C(C=C2)P(O)(O)=O)C2=C1 OPLDWQUCYFHJLJ-UHFFFAOYSA-N 0.000 claims 1
- TWKSFBHDPHIEOI-UHFFFAOYSA-N [[8-naphthalen-1-yl-6-(1H-pyrrol-3-yl)quinolin-2-yl]amino]methylphosphonic acid Chemical compound C1=C(C=2C3=CC=CC=C3C=CC=2)C2=NC(NCP(O)(=O)O)=CC=C2C=C1C=1C=CNC=1 TWKSFBHDPHIEOI-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000012190 activator Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atoms Chemical group C* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- JYYCNKSHXVLNRX-UHFFFAOYSA-N ethoxy-(8-naphthalen-1-yl-6-nitroquinolin-2-yl)phosphinic acid Chemical compound C1=CC=C2C(C3=CC(=CC4=CC=C(N=C43)P(O)(=O)OCC)[N+]([O-])=O)=CC=CC2=C1 JYYCNKSHXVLNRX-UHFFFAOYSA-N 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- YJPWXOXAVVBYLY-UHFFFAOYSA-M lithium;5-ethoxy-6-iodo-8-naphthalen-1-ylquinoline-2-carboxylate Chemical compound [Li+].C12=NC(C([O-])=O)=CC=C2C(OCC)=C(I)C=C1C1=CC=CC2=CC=CC=C12 YJPWXOXAVVBYLY-UHFFFAOYSA-M 0.000 claims 1
- AJHAOELQLZOELB-UHFFFAOYSA-M lithium;6-iodo-8-naphthalen-1-ylquinoline-2-carboxylate Chemical compound [Li+].C1=CC=C2C(C3=CC(I)=CC4=CC=C(N=C43)C(=O)[O-])=CC=CC2=C1 AJHAOELQLZOELB-UHFFFAOYSA-M 0.000 claims 1
- WMUQUXXLQRLUGI-UHFFFAOYSA-M lithium;8-naphthalen-1-yl-6-thiophen-2-ylquinoline-2-carboxylate Chemical compound [Li+].C1=C(C=2C3=CC=CC=C3C=CC=2)C2=NC(C(=O)[O-])=CC=C2C=C1C1=CC=CS1 WMUQUXXLQRLUGI-UHFFFAOYSA-M 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 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 1
- 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 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000007069 methylation reaction Methods 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- KAESVJOAVNADME-UHFFFAOYSA-N pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 1
Claims (11)
- åŒïŒïŒ©ïŒ
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| EP08152046 | 2008-02-28 | ||
| EP08152046.2 | 2008-02-28 | ||
| PCT/EP2009/052314 WO2009106586A1 (en) | 2008-02-28 | 2009-02-26 | Quinolines as inhibitors of farnesyl pyrophosphate synthase |
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| JP2011514893A JP2011514893A (ja) | 2011-05-12 |
| JP2011514893A5 true JP2011514893A5 (ja) | 2012-04-12 |
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| US (1) | US20120094958A1 (ja) |
| EP (1) | EP2250152A1 (ja) |
| JP (1) | JP2011514893A (ja) |
| KR (1) | KR20100124732A (ja) |
| CN (1) | CN101959865A (ja) |
| AU (1) | AU2009218468A1 (ja) |
| BR (1) | BRPI0908396A2 (ja) |
| CA (1) | CA2717011A1 (ja) |
| EA (1) | EA201001362A1 (ja) |
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| JP2012519211A (ja) * | 2009-03-02 | 2012-08-23 | ãµãŒããªã¹ ãã¡ãŒãã·ã¥ãŒãã£ã«ã«ãºïŒ ã€ã³ã³ãŒãã¬ã€ããã | ãµãŒãã¥ã€ã³èª¿ç¯ååç©ãšããŠã®ïŒâ眮æãããªã³ããã³é¢é£é¡äŒŒäœ |
| WO2013090929A1 (en) * | 2011-12-15 | 2013-06-20 | Gilead Sciences, Inc. | Amino quinoline derivatives inhibitors of hcv |
| CN104142378B (zh) * | 2014-07-29 | 2015-12-30 | ååçå·¥å€§åŠ | èå±è²è°±æ³åå®éæµå®æ°šåºç²é žä¹é ¯çæ¹æ³ |
| CN111225672B (zh) | 2017-10-16 | 2023-09-29 | æž åå€§åŠ | ç²çŸæé žéè·¯æå¶ååå ¶è¯ç©ç»åç© |
| CN111440161B (zh) * | 2020-05-15 | 2023-04-14 | äžåœè¯ç§å€§åŠ | äžç§å ·æpar4æ®æ掻æ§çäºç¯æè³åºç±»ååç©åå ¶åºçš |
| CN112980809B (zh) * | 2021-03-17 | 2023-04-11 | äºåäžçå·¥äžæéèŽ£ä»»å ¬åž | äžç§çèæ³å°ŒåºçŠç£·é žåé ¶åºå åå ¶åºçš |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5254544A (en) * | 1992-09-25 | 1993-10-19 | E. R. Squibb & Sons, Inc. | Hydroxyphosphinyl phosphonate squalene synthetase inhibitors and method |
| US20020151459A1 (en) * | 2000-02-25 | 2002-10-17 | Merck & Co., Inc. | Methods for identifying compounds useful for inhibiting farnesyl diphosphate synthase |
-
2009
- 2009-02-26 CA CA2717011A patent/CA2717011A1/en not_active Abandoned
- 2009-02-26 AU AU2009218468A patent/AU2009218468A1/en not_active Abandoned
- 2009-02-26 KR KR1020107019046A patent/KR20100124732A/ko not_active Application Discontinuation
- 2009-02-26 US US12/918,880 patent/US20120094958A1/en not_active Abandoned
- 2009-02-26 CN CN2009801064544A patent/CN101959865A/zh active Pending
- 2009-02-26 JP JP2010548111A patent/JP2011514893A/ja active Pending
- 2009-02-26 EA EA201001362A patent/EA201001362A1/ru unknown
- 2009-02-26 WO PCT/EP2009/052314 patent/WO2009106586A1/en active Application Filing
- 2009-02-26 MX MX2010009518A patent/MX2010009518A/es not_active Application Discontinuation
- 2009-02-26 BR BRPI0908396-0A patent/BRPI0908396A2/pt not_active IP Right Cessation
- 2009-02-26 EP EP09715302A patent/EP2250152A1/en not_active Withdrawn
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