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

Dérivés de la quinolyl propyl piperidine et leur utilisation en tant que antibactériens. Download PDF

Info

Publication number: OA12022A
Authority: OA; OAPI
Prior art keywords: propyl; acid; piperidine; methoxyquinolin; hydroxy
Prior art date: 1999-09-17

Application number

OA1200200074A

Other languages

English (en)

French (fr)

Inventor

Jean-Luc Malleron

Michel Tabart

Jean-Christophe Carry

Michel Evers

Youssef Elahmad

Serge Mignani

Fabrice Vivani

Michel Cheve

Original Assignee

Aventis Pharma Sa

Priority date (The priority date 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 date listed.)

1999-09-17

Filing date

2000-09-14

Publication date

2006-04-19

2000-09-14 Application filed by Aventis Pharma Sa filed Critical Aventis Pharma Sa

2006-04-19 Publication of OA12022A publication Critical patent/OA12022A/fr

Links

-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
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
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CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012025 fluorinating agent Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
229960003692 gamma aminobutyric acid Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000004969 haloethyl group Chemical group 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
239000011630 iodine Substances 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
229960003136 leucine Drugs 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229960003646 lysine Drugs 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
GVWISOJSERXQBM-UHFFFAOYSA-O methyl(propyl)azanium Chemical compound CCC[NH2+]C GVWISOJSERXQBM-UHFFFAOYSA-O 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
BNTFCVMJHBNJAR-UHFFFAOYSA-N n,n-diethyl-1,1,2,3,3,3-hexafluoropropan-1-amine Chemical compound CCN(CC)C(F)(F)C(F)C(F)(F)F BNTFCVMJHBNJAR-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000001979 organolithium group Chemical group 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
150000002940 palladium Chemical class 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
238000000053 physical method Methods 0.000 description 1
MXXWOMGUGJBKIW-YPCIICBESA-N piperine Chemical compound C=1C=C2OCOC2=CC=1/C=C/C=C/C(=O)N1CCCCC1 MXXWOMGUGJBKIW-YPCIICBESA-N 0.000 description 1
WVWHRXVVAYXKDE-UHFFFAOYSA-N piperine Natural products O=C(C=CC=Cc1ccc2OCOc2c1)C3CCCCN3 WVWHRXVVAYXKDE-UHFFFAOYSA-N 0.000 description 1
235000019100 piperine Nutrition 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000243 solution Substances 0.000 description 1
229940031000 streptococcus pneumoniae Drugs 0.000 description 1
150000003900 succinic acid esters Chemical class 0.000 description 1
SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 description 1
229960000909 sulfur hexafluoride Drugs 0.000 description 1
QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003899 tartaric acid esters Chemical class 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
GJSGYPDDPQRWPK-UHFFFAOYSA-N tetrapentylammonium Chemical compound CCCCC[N+](CCCCC)(CCCCC)CCCCC GJSGYPDDPQRWPK-UHFFFAOYSA-N 0.000 description 1
OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- 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
- 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
- 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
- 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
- C07D401/14—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 three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (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)

OA1200200074A 1999-09-17 2000-09-14 Dérivés de la quinolyl propyl piperidine et leur utilisation en tant que antibactériens. OA12022A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9911679A FR2798656B1 (fr)	1999-09-17	1999-09-17	Derives de la quinolyl propyl piperidine, leur preparation et les compositions qui les contiennent

Publications (1)

Publication Number	Publication Date
OA12022A true OA12022A (fr)	2006-04-19

Family

ID=9549990

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200200074A OA12022A (fr)	1999-09-17	2000-09-14	Dérivés de la quinolyl propyl piperidine et leur utilisation en tant que antibactériens.

Country Status (30)

Country	Link
EP (2)	EP1218370B1 (de)
JP (1)	JP2004527448A (de)
KR (1)	KR20020038757A (de)
CN (1)	CN1374959A (de)
AP (1)	AP2002002459A0 (de)
AT (1)	ATE284399T1 (de)
AU (1)	AU7429500A (de)
BG (1)	BG106524A (de)
BR (1)	BR0014060A (de)
CA (1)	CA2383836A1 (de)
CZ (1)	CZ2002940A3 (de)
DE (2)	DE60016611T2 (de)
DZ (1)	DZ3195A1 (de)
EA (1)	EA005183B1 (de)
EE (1)	EE200200138A (de)
FR (1)	FR2798656B1 (de)
GE (1)	GEP20043223B (de)
HR (1)	HRP20020214A2 (de)
HU (1)	HUP0204283A3 (de)
IL (1)	IL148720A0 (de)
MA (1)	MA26820A1 (de)
MX (1)	MXPA02001979A (de)
NO (1)	NO20021253L (de)
OA (1)	OA12022A (de)
PL (1)	PL354809A1 (de)
SK (1)	SK3632002A3 (de)
TN (1)	TNSN00184A1 (de)
WO (1)	WO2001025227A2 (de)
YU (1)	YU19002A (de)
ZA (1)	ZA200202073B (de)

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GB9822440D0 (en)	1998-10-14	1998-12-09	Smithkline Beecham Plc	Medicaments
GB9917408D0 (en)	1999-07-23	1999-09-22	Smithkline Beecham Plc	Compounds
GB9917406D0 (en)	1999-07-23	1999-09-22	Smithkline Beecham Plc	Compounds
IL154107A0 (en)	2000-07-26	2003-07-31	Smithkline Beecham Plc	Aminopiperidine quinolines and their azaisosteric analogues with antibacterial activity
GB0031086D0 (en) *	2000-12-20	2001-01-31	Smithkline Beecham Plc	Medicaments
GB0101577D0 (en)	2001-01-22	2001-03-07	Smithkline Beecham Plc	Compounds
GB0112836D0 (en)	2001-05-25	2001-07-18	Smithkline Beecham Plc	Medicaments
GB0112834D0 (en)	2001-05-25	2001-07-18	Smithkline Beecham Plc	Medicaments
AU2003239302A1 (en)	2002-01-29	2003-09-02	Glaxo Group Limited	Aminopiperidine compounds, process for their preparation, and pharmaceutical compositions containing them
WO2003064421A1 (en)	2002-01-29	2003-08-07	Glaxo Group Limited	Aminopiperidine derivatives
TW200409637A (en)	2002-06-26	2004-06-16	Glaxo Group Ltd	Compounds
TW200406413A (en)	2002-06-26	2004-05-01	Glaxo Group Ltd	Compounds
FR2842807A1 (fr) *	2002-07-23	2004-01-30	Aventis Pharma Sa	Derives de la quinolyl propyl piperidine, procede et intermediaires de preparation et compositions les renfermant
FR2844268B1 (fr) *	2002-09-11	2004-10-22	Aventis Pharma Sa	Derives de la quinolyl propyl piperidine, leurs procedes et intermediaires de preparation et les compositions qui les contiennent
FR2844270B1 (fr) *	2002-09-11	2006-05-19	Aventis Pharma Sa	Derives de la quinolyl propyl piperidine, leur procede et intermediaires de preparation et les compositions qui les contiennent
BR0315221A (pt) *	2002-10-10	2005-08-23	Morphochem Ag Komb Chemie	Compostos com atividade antibacteriana
AU2003303956A1 (en)	2002-11-05	2004-11-23	Smithkline Beecham Corporation	Antibacterial agents
AU2003291227A1 (en)	2002-11-05	2004-06-07	Smithkline Beecham Corporation	Antibacterial agents
WO2004050036A2 (en)	2002-12-04	2004-06-17	Glaxo Group Limited	Quinolines and nitrogenated derivatives thereof and their use as antibacterial agents
EP1799674B1 (de) *	2004-10-05	2010-05-05	Actelion Pharmaceuticals Ltd.	Neue piperidin-antibiotika
CA2581057A1 (en) *	2004-10-05	2006-04-13	Actelion Pharmaceuticals Ltd	New piperidine antibiotics
JP2008528586A (ja)	2005-01-25	2008-07-31	グラクソグループリミテッド	抗菌剤
US7709472B2 (en)	2005-01-25	2010-05-04	Glaxo Group Limited	Antibacterial agents
JP2008528588A (ja)	2005-01-25	2008-07-31	グラクソグループリミテッド	抗菌剤
WO2006081264A1 (en)	2005-01-25	2006-08-03	Glaxo Group Limited	Antibacterial agents
WO2007086016A1 (en)	2006-01-26	2007-08-02	Actelion Pharmaceuticals Ltd	Tetrahydropyrane antibiotics
ATE481406T1 (de)	2006-04-06	2010-10-15	Glaxo Group Ltd	Pyrrolochinoxalinonderivate als antibakterielle mittel
GB0613208D0 (en)	2006-07-03	2006-08-09	Glaxo Group Ltd	Compounds
EP1992628A1 (de)	2007-05-18	2008-11-19	Glaxo Group Limited	Derivate und Analoge von N-Ethylquinolonen und N-Ethylazaquinolonen
AU2008249745B2 (en) *	2007-05-09	2012-01-12	Pfizer Inc.	Substituted heterocyclic derivatives and compositions and their pharmaceutical use as antibacterials
EP2080761A1 (de)	2008-01-18	2009-07-22	Glaxo Group Limited	Verbindungen
EP2352734A1 (de)	2008-10-17	2011-08-10	Glaxo Group Limited	Als antibakterielle mittel verwendete tricyclische stickstoffverbindungen
JP5653935B2 (ja)	2009-01-15	2015-01-14	グラクソグループリミテッドＧｌａｘｏＧｒｏｕｐＬｉｍｉｔｅｄ	抗菌薬として有用なナフチリジン―２（１ｈ）−オン化合物
EP3057948B1 (de) *	2013-10-14	2018-03-14	Eisai R&D Management Co., Ltd.	Selektiv substituierte chinolinderivate
EP3639824A1 (de)	2014-08-22	2020-04-22	GlaxoSmithKline Intellectual Property Development Limited	Tricyclische stickstoffhaltige verbindungen zur behandlung einer infektion mit neisseria gonorrhoea
UY36851A (es)	2015-08-16	2017-03-31	Glaxosmithkline Ip Dev Ltd	Compuestos para uso en aplicaciones antibacterianas
SG11201804170RA (en)	2015-12-17	2018-06-28	Merck Patent Gmbh	Polycyclic tlr7/8 antagonists and use thereof in the treatment of immune disorders
EP3497094B1 (de)	2016-08-08	2023-02-15	Merck Patent GmbH	Tlr7/8-antagonisten und verwendungen davon

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EP1051413B1 (de) *	1998-01-26	2003-06-04	SmithKline Beecham plc	Chinolinderivate als antibakterielles arzneimittel
EP1144404A1 (de) *	1999-01-20	2001-10-17	Smithkline Beecham Plc	Piperidinylchinoline als proteintyrosinkinasehemmer

1999
- 1999-09-17 FR FR9911679A patent/FR2798656B1/fr not_active Expired - Fee Related
2000
- 2000-09-14 EA EA200200374A patent/EA005183B1/ru not_active IP Right Cessation
- 2000-09-14 EE EEP200200138A patent/EE200200138A/xx unknown
- 2000-09-14 HU HU0204283A patent/HUP0204283A3/hu unknown
- 2000-09-14 EP EP00962637A patent/EP1218370B1/de not_active Expired - Lifetime
- 2000-09-14 CZ CZ2002940A patent/CZ2002940A3/cs unknown
- 2000-09-14 MX MXPA02001979A patent/MXPA02001979A/es unknown
- 2000-09-14 PL PL00354809A patent/PL354809A1/xx not_active Application Discontinuation
- 2000-09-14 DE DE60016611T patent/DE60016611T2/de not_active Expired - Fee Related
- 2000-09-14 SK SK363-2002A patent/SK3632002A3/sk unknown
- 2000-09-14 HR HR20020214A patent/HRP20020214A2/hr not_active Application Discontinuation
- 2000-09-14 BR BR0014060-0A patent/BR0014060A/pt not_active IP Right Cessation
- 2000-09-14 KR KR1020027003547A patent/KR20020038757A/ko not_active Ceased
- 2000-09-14 WO PCT/FR2000/002541 patent/WO2001025227A2/fr not_active Ceased
- 2000-09-14 DZ DZ003195A patent/DZ3195A1/xx active
- 2000-09-14 CA CA002383836A patent/CA2383836A1/fr not_active Abandoned
- 2000-09-14 AP APAP/P/2002/002459A patent/AP2002002459A0/en unknown
- 2000-09-14 AU AU74295/00A patent/AU7429500A/en not_active Abandoned
- 2000-09-14 CN CN00813020A patent/CN1374959A/zh active Pending
- 2000-09-14 IL IL14872000A patent/IL148720A0/xx unknown
- 2000-09-14 GE GEAP20006413A patent/GEP20043223B/en unknown
- 2000-09-14 AT AT00962637T patent/ATE284399T1/de not_active IP Right Cessation
- 2000-09-14 YU YU19002A patent/YU19002A/sh unknown
- 2000-09-14 JP JP2001528171A patent/JP2004527448A/ja active Pending
- 2000-09-14 OA OA1200200074A patent/OA12022A/fr unknown
- 2000-09-14 DE DE60034713T patent/DE60034713T2/de not_active Expired - Fee Related
- 2000-09-14 EP EP04019136A patent/EP1484328B1/de not_active Expired - Lifetime
- 2000-09-15 TN TNTNSN00184A patent/TNSN00184A1/fr unknown
2002
- 2002-03-13 ZA ZA200202073A patent/ZA200202073B/en unknown
- 2002-03-13 NO NO20021253A patent/NO20021253L/no not_active Application Discontinuation
- 2002-03-14 MA MA26554A patent/MA26820A1/fr unknown
- 2002-03-15 BG BG106524A patent/BG106524A/xx unknown

Also Published As

Publication number	Publication date
CN1374959A (zh)	2002-10-16
MXPA02001979A (es)	2002-08-20
TNSN00184A1 (fr)	2005-11-10
HUP0204283A3 (en)	2004-07-28
GEP20043223B (en)	2004-04-26
EA200200374A1 (ru)	2002-10-31
JP2004527448A (ja)	2004-09-09
EP1218370A2 (de)	2002-07-03
BG106524A (en)	2003-01-31
BR0014060A (pt)	2002-05-21
PL354809A1 (en)	2004-02-23
NO20021253L (no)	2002-04-24
HUP0204283A2 (hu)	2003-04-28
ZA200202073B (en)	2003-08-27
DE60034713T2 (de)	2008-01-17
SK3632002A3 (en)	2003-04-01
DE60034713D1 (de)	2007-06-14
DZ3195A1 (fr)	2001-04-12
NO20021253D0 (no)	2002-03-13
EP1484328A1 (de)	2004-12-08
FR2798656A1 (fr)	2001-03-23
HRP20020214A2 (en)	2005-04-30
KR20020038757A (ko)	2002-05-23
DE60016611D1 (de)	2005-01-13
EE200200138A (et)	2003-06-16
EP1218370B1 (de)	2004-12-08
MA26820A1 (fr)	2004-12-20
CA2383836A1 (fr)	2001-04-12
CZ2002940A3 (cs)	2002-07-17
AU7429500A (en)	2001-05-10
IL148720A0 (en)	2002-09-12
EA005183B1 (ru)	2004-12-30
WO2001025227A2 (fr)	2001-04-12
DE60016611T2 (de)	2005-12-22
ATE284399T1 (de)	2004-12-15
WO2001025227A3 (fr)	2001-11-22
YU19002A (sh)	2005-06-10
EP1484328B1 (de)	2007-05-02
AP2002002459A0 (en)	2002-06-30
FR2798656B1 (fr)	2004-12-17

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US6602884B2 (en)	2003-08-05	Quinolylpropylpiperidine derivatives, their preparation, and compositions containing them
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