OA12922A - Dérivés de la quinolyl propyl pipéridine et leur utilisation en tant qu'agents antimicrobiens. - Google Patents
Dérivés de la quinolyl propyl pipéridine et leur utilisation en tant qu'agents antimicrobiens. Download PDFInfo
- Publication number
- OA12922A OA12922A OA1200500070A OA1200500070A OA12922A OA 12922 A OA12922 A OA 12922A OA 1200500070 A OA1200500070 A OA 1200500070A OA 1200500070 A OA1200500070 A OA 1200500070A OA 12922 A OA12922 A OA 12922A
- Authority
- OA
- OAPI
- Prior art keywords
- piperidine
- propyl
- chloro
- derivative
- radical
- Prior art date
Links
- -1 of quinolyl propylpiperidine Chemical compound 0.000 title claims description 337
- 239000004599 antimicrobial Substances 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 62
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 17
- 150000002367 halogens Chemical class 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 11
- 150000003053 piperidines Chemical class 0.000 claims abstract description 11
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 150000003254 radicals Chemical class 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 10
- 230000003647 oxidation Effects 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Chemical group 0.000 claims description 8
- 150000003248 quinolines Chemical class 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 229910052717 sulfur Chemical group 0.000 claims description 7
- 239000011593 sulfur Chemical group 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 238000005658 halogenation reaction Methods 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- ITAOQJWRWYAILY-UHFFFAOYSA-N 4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-hydroxypropyl]-1-(2-thiophen-2-ylsulfanylethyl)piperidine-3-carboxylic acid Chemical compound C12=CC(OC)=CC=C2N=CC(Cl)=C1C(O)CCC(C(C1)C(O)=O)CCN1CCSC1=CC=CS1 ITAOQJWRWYAILY-UHFFFAOYSA-N 0.000 claims description 4
- 230000029936 alkylation Effects 0.000 claims description 4
- 238000005804 alkylation reaction Methods 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 238000006392 deoxygenation reaction Methods 0.000 claims description 4
- 230000026030 halogenation Effects 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 125000000391 vinyl group Chemical class [H]C([*])=C([H])[H] 0.000 claims description 4
- BNJMRELGMDUDDB-UHFFFAOYSA-N $l^{1}-sulfanylbenzene Chemical compound [S]C1=CC=CC=C1 BNJMRELGMDUDDB-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 238000005937 allylation reaction Methods 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 238000003379 elimination reaction Methods 0.000 claims description 3
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 238000010511 deprotection reaction Methods 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 125000005592 polycycloalkyl group Polymers 0.000 claims description 2
- DITHIFQMPPCBCU-UHFFFAOYSA-N propa-1,2-diene Chemical group [CH]=C=C DITHIFQMPPCBCU-UHFFFAOYSA-N 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- 230000009466 transformation Effects 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- WKXRHAACRPUBIC-UHFFFAOYSA-N 2-piperidin-1-ium-3-ylacetate Chemical compound OC(=O)CC1CCCNC1 WKXRHAACRPUBIC-UHFFFAOYSA-N 0.000 abstract description 31
- 125000005843 halogen group Chemical group 0.000 abstract description 12
- 239000000543 intermediate Substances 0.000 abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract description 3
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 abstract description 3
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 abstract description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 abstract 1
- 125000000033 alkoxyamino group Chemical group 0.000 abstract 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 abstract 1
- VUNPWIPIOOMCPT-UHFFFAOYSA-N piperidin-3-ylmethanol Chemical class OCC1CCCNC1 VUNPWIPIOOMCPT-UHFFFAOYSA-N 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 208
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 38
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 33
- 239000002904 solvent Substances 0.000 description 29
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
- 238000001228 spectrum Methods 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- XJLSEXAGTJCILF-RXMQYKEDSA-N (R)-nipecotic acid zwitterion Chemical compound OC(=O)[C@@H]1CCCNC1 XJLSEXAGTJCILF-RXMQYKEDSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000012153 distilled water Substances 0.000 description 20
- 239000012074 organic phase Substances 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 19
- 235000019341 magnesium sulphate Nutrition 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 238000004128 high performance liquid chromatography Methods 0.000 description 18
- 239000012429 reaction media Substances 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 17
- 239000002585 base Substances 0.000 description 17
- 239000011521 glass Substances 0.000 description 16
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 238000010828 elution Methods 0.000 description 12
- 230000014759 maintenance of location Effects 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- XLIDUPWUYJWYGP-UHFFFAOYSA-N 3-chloro-6-methoxyquinoline Chemical compound N1=CC(Cl)=CC2=CC(OC)=CC=C21 XLIDUPWUYJWYGP-UHFFFAOYSA-N 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 239000008346 aqueous phase Substances 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- 230000005526 G1 to G0 transition Effects 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 238000001035 drying Methods 0.000 description 8
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Inorganic materials [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 7
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- XQXSGGXHUFAZKW-UHFFFAOYSA-N CCO.CC(C)O.CCCCCCC.CCN(CC)CC Chemical compound CCO.CC(C)O.CCCCCCC.CCN(CC)CC XQXSGGXHUFAZKW-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 150000004678 hydrides Chemical class 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 238000006467 substitution reaction Methods 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
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000001033 granulometry Methods 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- ARIRXGXQFLUMAM-UHFFFAOYSA-N methyl 4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-hydroxypropyl]-1-(2-thiophen-2-ylsulfanylethyl)piperidine-3-carboxylate Chemical compound C1CC(CCC(O)C=2C3=CC(OC)=CC=C3N=CC=2Cl)C(C(=O)OC)CN1CCSC1=CC=CS1 ARIRXGXQFLUMAM-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- MTTMAUBUJAWJQE-UHFFFAOYSA-N 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidine-3-carboxylic acid Chemical compound C12=CC(OC)=CC=C2N=CC(Cl)=C1CCCC1CCN(C(=O)OC(C)(C)C)CC1C(O)=O MTTMAUBUJAWJQE-UHFFFAOYSA-N 0.000 description 3
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- CYRNTCXVLGMSQS-UHFFFAOYSA-N OC.CC(C)O.CCCCCCC.CCN(CC)CC Chemical compound OC.CC(C)O.CCCCCCC.CCN(CC)CC CYRNTCXVLGMSQS-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 3
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
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- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0211213A FR2844268B1 (fr) | 2002-09-11 | 2002-09-11 | Derives de la quinolyl propyl piperidine, leurs procedes et intermediaires de preparation et les compositions qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA12922A true OA12922A (fr) | 2006-10-13 |
Family
ID=31725984
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200500070A OA12922A (fr) | 2002-09-11 | 2003-09-10 | Dérivés de la quinolyl propyl pipéridine et leur utilisation en tant qu'agents antimicrobiens. |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6841562B2 (de) |
| EP (1) | EP1539734B1 (de) |
| JP (1) | JP2006500403A (de) |
| KR (1) | KR20050042196A (de) |
| CN (1) | CN100415736C (de) |
| AT (1) | ATE319705T1 (de) |
| AU (1) | AU2003278297A1 (de) |
| BR (1) | BR0314185A (de) |
| CA (1) | CA2498628A1 (de) |
| DE (1) | DE60303954T2 (de) |
| DK (1) | DK1539734T3 (de) |
| EA (1) | EA009769B1 (de) |
| ES (1) | ES2256783T3 (de) |
| FR (1) | FR2844268B1 (de) |
| MA (1) | MA27433A1 (de) |
| MX (1) | MXPA05002655A (de) |
| NO (1) | NO20051754D0 (de) |
| OA (1) | OA12922A (de) |
| PT (1) | PT1539734E (de) |
| RS (1) | RS20050212A (de) |
| TN (1) | TNSN05069A1 (de) |
| WO (1) | WO2004024713A1 (de) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0112834D0 (en) | 2001-05-25 | 2001-07-18 | Smithkline Beecham Plc | Medicaments |
| WO2003064431A2 (en) * | 2002-01-29 | 2003-08-07 | Glaxo Group Limited | Aminopiperidine compounds, process for their preparation, and pharmaceutical compositions containing them |
| US7312212B2 (en) * | 2002-01-29 | 2007-12-25 | Glaxo Group Limited | Aminopiperidine derivatives |
| TW200406413A (en) * | 2002-06-26 | 2004-05-01 | Glaxo Group Ltd | Compounds |
| TW200409637A (en) * | 2002-06-26 | 2004-06-16 | Glaxo Group Ltd | Compounds |
| ES2340484T3 (es) | 2002-11-05 | 2010-06-04 | Glaxo Group Limited | Agentes antibacterianos. |
| AU2003291227A1 (en) | 2002-11-05 | 2004-06-07 | Smithkline Beecham Corporation | Antibacterial agents |
| AR042486A1 (es) * | 2002-12-18 | 2005-06-22 | Glaxo Group Ltd | Compuesto de quinolina y naftiridina halosustituido en la posicion 3, procedimiento para preparar el compuesto, composicion farmaceutica que lo comprende y su uso para preparar dicha composicion . |
| GB2413863A (en) * | 2004-05-08 | 2005-11-09 | Ibm | Method and system for distribution of information |
| EP1773831A1 (de) * | 2004-07-08 | 2007-04-18 | Glaxo Group Limited | Antibakterielle mittel |
| DE602005021133D1 (de) * | 2004-10-05 | 2010-06-17 | Actelion Pharmaceuticals Ltd | Neue piperidin-antibiotika |
| EP1845995A4 (de) | 2005-01-25 | 2010-03-03 | Glaxo Group Ltd | Antibakterielle wirkstoffe |
| WO2006081264A1 (en) | 2005-01-25 | 2006-08-03 | Glaxo Group Limited | Antibacterial agents |
| EP1846416A4 (de) | 2005-01-25 | 2009-07-01 | Glaxo Group Ltd | Antibakterielle wirkstoffe |
| JP2008528588A (ja) * | 2005-01-25 | 2008-07-31 | グラクソ グループ リミテッド | 抗菌剤 |
| EP1846411A4 (de) * | 2005-01-25 | 2010-08-04 | Glaxo Group Ltd | Antibakterielle wirkstoffe |
| MY150958A (en) * | 2005-06-16 | 2014-03-31 | Astrazeneca Ab | Compounds for the treatment of multi-drug resistant bacterial infections |
| DE602007009205D1 (de) | 2006-04-06 | 2010-10-28 | Glaxo Group Ltd | Pyrrolochinoxalinonderivate als antibakterielle mittel |
| EP1992628A1 (de) | 2007-05-18 | 2008-11-19 | Glaxo Group Limited | Derivate und Analoge von N-Ethylquinolonen und N-Ethylazaquinolonen |
| US20100144717A1 (en) * | 2006-12-15 | 2010-06-10 | Janelle Comita-Prevoir | 2-quinolinone and 2-quinoxalinone-derivatives and their use as antibacterial agents |
| NZ579877A (en) * | 2007-04-20 | 2011-09-30 | Glaxo Group Ltd | Tricyclic nitrogen containing compounds as antibacterial agents |
| EP2080761A1 (de) | 2008-01-18 | 2009-07-22 | Glaxo Group Limited | Verbindungen |
| FR2936798B1 (fr) * | 2008-10-03 | 2012-09-28 | Novexel | Nouveaux composes heterocycliques azotes, leur preparation et leur utilisation comme medicaments antibacteriens. |
| FR2936951B1 (fr) * | 2008-10-10 | 2010-12-03 | Novexel | Nouvelles combinaisons de composes heterocycliques azotes antibacteriens avec d'autres composes antibacteriens et leur utilisation comme medicaments |
| FR2937034B1 (fr) * | 2008-10-10 | 2012-11-23 | Novexel | Nouveaux composes heterocycliques azotes, leur preparation et leur utilisation comme medicaments antibacteriens |
| EP2352734A1 (de) | 2008-10-17 | 2011-08-10 | Glaxo Group Limited | Als antibakterielle mittel verwendete tricyclische stickstoffverbindungen |
| WO2010081874A1 (en) | 2009-01-15 | 2010-07-22 | Glaxo Group Limited | Naphthyridin-2 (1 h)-one compounds useful as antibacterials |
| CA2958800C (en) | 2014-08-22 | 2020-10-27 | Glaxosmithkline Intellectual Property Development Limited | Tricyclic nitrogen containing compounds for treating neisseria gonorrhoea infection |
| UY36851A (es) | 2015-08-16 | 2017-03-31 | Glaxosmithkline Ip Dev Ltd | Compuestos para uso en aplicaciones antibacterianas |
| KR102231872B1 (ko) * | 2019-10-04 | 2021-03-26 | 성균관대학교산학협력단 | 포스포늄일리드를 이용한 디아진-n-옥사이드의 위치선택적 알킬화 방법 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GT198900008A (es) * | 1988-01-29 | 1990-07-17 | Derivados de quinolina, quinazolina y cinolina. | |
| US6117884A (en) * | 1997-07-31 | 2000-09-12 | Daeuble; John | 4-substituted quinoline derivatives having fungicidal activity |
| JP2002535323A (ja) * | 1999-01-20 | 2002-10-22 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | プロテインキナーゼ阻害剤としてのピペリジニルキノリン |
| FR2798656B1 (fr) * | 1999-09-17 | 2004-12-17 | Aventis Pharma Sa | Derives de la quinolyl propyl piperidine, leur preparation et les compositions qui les contiennent |
| US6603005B2 (en) * | 2000-11-15 | 2003-08-05 | Aventis Pharma S.A. | Heterocyclylalkylpiperidine derivatives, their preparation and compositions containing them |
| FR2816618B1 (fr) * | 2000-11-15 | 2002-12-27 | Aventis Pharma Sa | Derives heterocyclylalcoyl piperidine, leur preparation et les compositions qui les contiennent |
| FR2822154B1 (fr) * | 2001-03-13 | 2005-10-21 | Aventis Pharma Sa | Derives de la quinolyl propyl piperidine, leur preparation et les compositions qui les contiennent |
-
2002
- 2002-09-11 FR FR0211213A patent/FR2844268B1/fr not_active Expired - Fee Related
-
2003
- 2003-09-10 CA CA002498628A patent/CA2498628A1/fr not_active Abandoned
- 2003-09-10 DK DK03769606T patent/DK1539734T3/da active
- 2003-09-10 KR KR1020057004150A patent/KR20050042196A/ko not_active Ceased
- 2003-09-10 AU AU2003278297A patent/AU2003278297A1/en not_active Abandoned
- 2003-09-10 DE DE60303954T patent/DE60303954T2/de not_active Expired - Lifetime
- 2003-09-10 CN CNB038214911A patent/CN100415736C/zh not_active Expired - Fee Related
- 2003-09-10 EA EA200500474A patent/EA009769B1/ru not_active IP Right Cessation
- 2003-09-10 WO PCT/FR2003/002687 patent/WO2004024713A1/fr not_active Ceased
- 2003-09-10 OA OA1200500070A patent/OA12922A/fr unknown
- 2003-09-10 RS YUP-2005/0212A patent/RS20050212A/sr unknown
- 2003-09-10 US US10/659,095 patent/US6841562B2/en not_active Expired - Fee Related
- 2003-09-10 PT PT03769606T patent/PT1539734E/pt unknown
- 2003-09-10 ES ES03769606T patent/ES2256783T3/es not_active Expired - Lifetime
- 2003-09-10 MX MXPA05002655A patent/MXPA05002655A/es unknown
- 2003-09-10 AT AT03769606T patent/ATE319705T1/de not_active IP Right Cessation
- 2003-09-10 BR BR0314185-3A patent/BR0314185A/pt not_active Application Discontinuation
- 2003-09-10 JP JP2004535595A patent/JP2006500403A/ja active Pending
- 2003-09-10 EP EP03769606A patent/EP1539734B1/de not_active Expired - Lifetime
-
2005
- 2005-03-10 TN TNP2005000069A patent/TNSN05069A1/fr unknown
- 2005-03-11 MA MA28142A patent/MA27433A1/fr unknown
- 2005-04-08 NO NO20051754A patent/NO20051754D0/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1681801A (zh) | 2005-10-12 |
| MXPA05002655A (es) | 2005-09-08 |
| CA2498628A1 (fr) | 2004-03-25 |
| ES2256783T3 (es) | 2006-07-16 |
| PT1539734E (pt) | 2006-05-31 |
| AU2003278297A1 (en) | 2004-04-30 |
| DE60303954T2 (de) | 2006-12-07 |
| WO2004024713A1 (fr) | 2004-03-25 |
| FR2844268A1 (fr) | 2004-03-12 |
| EA200500474A1 (ru) | 2005-08-25 |
| FR2844268B1 (fr) | 2004-10-22 |
| TNSN05069A1 (fr) | 2007-05-14 |
| JP2006500403A (ja) | 2006-01-05 |
| US20040082610A1 (en) | 2004-04-29 |
| DK1539734T3 (da) | 2006-06-06 |
| NO20051754L (no) | 2005-04-08 |
| RS20050212A (sr) | 2007-09-21 |
| MA27433A1 (fr) | 2005-07-01 |
| EP1539734A1 (de) | 2005-06-15 |
| KR20050042196A (ko) | 2005-05-04 |
| DE60303954D1 (de) | 2006-05-04 |
| EP1539734B1 (de) | 2006-03-08 |
| US6841562B2 (en) | 2005-01-11 |
| ATE319705T1 (de) | 2006-03-15 |
| CN100415736C (zh) | 2008-09-03 |
| NO20051754D0 (no) | 2005-04-08 |
| BR0314185A (pt) | 2005-08-09 |
| EA009769B1 (ru) | 2008-04-28 |
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