OA12022A - Dérivés de la quinolyl propyl piperidine et leur utilisation en tant que antibactériens. - Google Patents

Info

Publication number

OA12022A

OA12022A OA1200200074A OA1200200074A OA12022A OA 12022 A OA12022 A OA 12022A OA 1200200074 A OA1200200074 A OA 1200200074A OA 1200200074 A OA1200200074 A OA 1200200074A OA 12022 A OA12022 A OA 12022A

Authority

OA

OAPI

Prior art keywords

propyl

acid

piperidine

methoxyquinolin

hydroxy

Prior art date

1999-09-17

Links

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• -1 Quinolyl propyl piperidine derivatives Chemical class 0.000 title claims abstract description 2183
• 230000000844 anti-bacterial effect Effects 0.000 title abstract 2
• 229940088710 antibiotic agent Drugs 0.000 title 1
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 35
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 28
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 27
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 26
• 125000005843 halogen group Chemical group 0.000 claims abstract description 26
• 150000003839 salts Chemical class 0.000 claims abstract description 25
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 22
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 19
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 18
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 18
• 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 15
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 12
• 239000000203 mixture Substances 0.000 claims abstract description 12
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims abstract description 8
• 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
• 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims abstract description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2231
• 239000002253 acid Substances 0.000 claims description 1426
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 153
• 229910052736 halogen Inorganic materials 0.000 claims description 31
• 150000002367 halogens Chemical class 0.000 claims description 26
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
• 125000004432 carbon atom Chemical group C* 0.000 claims description 21
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 239000011593 sulfur Chemical group 0.000 claims description 19
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
• 238000000034 method Methods 0.000 claims description 18
• 239000001301 oxygen Chemical group 0.000 claims description 18
• 150000003254 radicals Chemical class 0.000 claims description 18
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• 125000001424 substituent group Chemical group 0.000 claims description 13
• 238000006243 chemical reaction Methods 0.000 claims description 12
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
• DITHIFQMPPCBCU-UHFFFAOYSA-N propa-1,2-diene Chemical group [CH]=C=C DITHIFQMPPCBCU-UHFFFAOYSA-N 0.000 claims description 8
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 230000026030 halogenation Effects 0.000 claims description 6
• 238000005658 halogenation reaction Methods 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• 239000001257 hydrogen Substances 0.000 claims description 5
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
• BNJMRELGMDUDDB-UHFFFAOYSA-N $l^{1}-sulfanylbenzene Chemical compound [S]C1=CC=CC=C1 BNJMRELGMDUDDB-UHFFFAOYSA-N 0.000 claims description 4
• 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 4
• 238000009833 condensation Methods 0.000 claims description 4
• 230000005494 condensation Effects 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 238000006467 substitution reaction Methods 0.000 claims description 4
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 3
• 238000006704 dehydrohalogenation reaction Methods 0.000 claims description 3
• 125000006239 protecting group Chemical group 0.000 claims description 3
• 125000004122 cyclic group Chemical group 0.000 claims description 2
• 125000000623 heterocyclic group Chemical group 0.000 claims description 2
• 150000003053 piperidines Chemical class 0.000 claims description 2
• SFOWBJMUOXCSJZ-UHFFFAOYSA-N 6-methoxypyridine-2,3-dicarboxylic acid Chemical compound COC1=CC=C(C(O)=O)C(C(O)=O)=N1 SFOWBJMUOXCSJZ-UHFFFAOYSA-N 0.000 claims 3
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
• CCXGQGOVILILGZ-NYOMEMIMSA-N 2-[(3r,4r)-1-[2-(3-fluorophenyl)sulfanylethyl]-4-[3-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]piperidin-3-yl]acetic acid Chemical group C([C@H]([C@H](C1)CC(O)=O)CCC(O)C2=CC=NC3=CC=C(C=C32)OC)CN1CCSC1=CC=CC(F)=C1 CCXGQGOVILILGZ-NYOMEMIMSA-N 0.000 claims 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
• 239000002671 adjuvant Substances 0.000 claims 1
• 229910052799 carbon Inorganic materials 0.000 claims 1
• 239000003085 diluting agent Substances 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 239000008194 pharmaceutical composition Substances 0.000 claims 1
• 238000002360 preparation method Methods 0.000 abstract description 3
• RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 abstract description 2
• 241000699670 Mus sp. Species 0.000 abstract description 2
• 150000001875 compounds Chemical class 0.000 abstract description 2
• 238000000338 in vitro Methods 0.000 abstract description 2
• 238000001727 in vivo Methods 0.000 abstract description 2
• 229960003085 meticillin Drugs 0.000 abstract description 2
• 241000191940 Staphylococcus Species 0.000 abstract 2
• 125000005366 cycloalkylthio group Chemical group 0.000 abstract 2
• DPPJBWQYOFQJCU-UHFFFAOYSA-N 2-(3-piperidin-1-ylpropyl)quinoline Chemical class C=1C=C2C=CC=CC2=NC=1CCCN1CCCCC1 DPPJBWQYOFQJCU-UHFFFAOYSA-N 0.000 abstract 1
• 241000194033 Enterococcus Species 0.000 abstract 1
• 241000194017 Streptococcus Species 0.000 abstract 1
• 230000000694 effects Effects 0.000 abstract 1
• 230000010534 mechanism of action Effects 0.000 abstract 1
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 406
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 263
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 221
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 158
• WKXRHAACRPUBIC-UHFFFAOYSA-N 2-piperidin-1-ium-3-ylacetate Chemical compound OC(=O)CC1CCCNC1 WKXRHAACRPUBIC-UHFFFAOYSA-N 0.000 description 132
• XJLSEXAGTJCILF-RXMQYKEDSA-N (R)-nipecotic acid zwitterion Chemical compound OC(=O)[C@@H]1CCCNC1 XJLSEXAGTJCILF-RXMQYKEDSA-N 0.000 description 128
• 125000004035 thiopropyl group Chemical group [H]SC([H])([H])C([H])([H])C([H])([H])* 0.000 description 121
• 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 102
• BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 49
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 36
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 32
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 28
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 28
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 28
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 24
• 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 22
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 22
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 22
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 22
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 21
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 20
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 19
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 18
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 18
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 18
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 17
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 17
• BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 17
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 17
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 15
• 239000000047 product Substances 0.000 description 15
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 14
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 14
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 14
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 14
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 13
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
• 239000002904 solvent Substances 0.000 description 12
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 11
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 11
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 10
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 9
• 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 9
• 125000000446 sulfanediyl group Chemical group *S* 0.000 description 9
• 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 8
• XJLSEXAGTJCILF-UHFFFAOYSA-N nipecotic acid Chemical compound OC(=O)C1CCCNC1 XJLSEXAGTJCILF-UHFFFAOYSA-N 0.000 description 8
• 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 description 8
• 238000010992 reflux Methods 0.000 description 8
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 7
• 239000002609 medium Substances 0.000 description 7
• 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 description 7
• MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 5
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 5
• HFDLDPJYCIEXJP-UHFFFAOYSA-N 6-methoxyquinoline Chemical compound N1=CC=CC2=CC(OC)=CC=C21 HFDLDPJYCIEXJP-UHFFFAOYSA-N 0.000 description 5
• 239000002585 base Substances 0.000 description 5
• 150000002148 esters Chemical class 0.000 description 5
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 5
• APOYTRAZFJURPB-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)-n-(trifluoro-$l^{4}-sulfanyl)ethanamine Chemical compound COCCN(S(F)(F)F)CCOC APOYTRAZFJURPB-UHFFFAOYSA-N 0.000 description 4
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
• 230000007062 hydrolysis Effects 0.000 description 4
• 238000006460 hydrolysis reaction Methods 0.000 description 4
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 4
• 239000000543 intermediate Substances 0.000 description 4
• 150000002825 nitriles Chemical class 0.000 description 4
• 239000003960 organic solvent Substances 0.000 description 4
• 239000011541 reaction mixture Substances 0.000 description 4
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
• OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 3
• ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 3
• XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 3
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 150000001408 amides Chemical class 0.000 description 3
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
• 125000003386 piperidinyl group Chemical group 0.000 description 3
• 239000011591 potassium Substances 0.000 description 3
• 229910052700 potassium Inorganic materials 0.000 description 3
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
• 150000003248 quinolines Chemical class 0.000 description 3
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
• 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 3
• XZFULJSMISJEHW-BWKNWUBXSA-N (3r,4r)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-(3-pyridin-3-ylsulfanylpropyl)piperidine-3-carboxylic acid Chemical compound C([C@H]([C@H](C1)C(O)=O)CCCC2=CC=NC3=CC=C(C=C32)OC)CN1CCCSC1=CC=CN=C1 XZFULJSMISJEHW-BWKNWUBXSA-N 0.000 description 2
• OYFKFZBXVYKVCD-DUXPYHPUSA-N (e)-3-(3-chloro-4-fluorophenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=C(F)C(Cl)=C1 OYFKFZBXVYKVCD-DUXPYHPUSA-N 0.000 description 2
• LDKSCZJUIURGMW-UHFFFAOYSA-N 1-isothiocyanato-3-methylsulfanylpropane Chemical group CSCCCN=C=S LDKSCZJUIURGMW-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• ZEXWTDGPQUVSME-VWNXMTODSA-N 2-[(3r,4r)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(4-methylphenyl)sulfanylethyl]piperidin-3-yl]acetic acid Chemical compound C([C@H]([C@H](C1)CC(O)=O)CCCC2=CC=NC3=CC=C(C=C32)OC)CN1CCSC1=CC=C(C)C=C1 ZEXWTDGPQUVSME-VWNXMTODSA-N 0.000 description 2
• 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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