HRP20030379A2 - Heterocyclylalkylpiperidine derivatives, their preparation and compositions containing same - Google Patents
Heterocyclylalkylpiperidine derivatives, their preparation and compositions containing sameInfo
- Publication number
- HRP20030379A2 HRP20030379A2 HR20030379A HRP20030379A HRP20030379A2 HR P20030379 A2 HRP20030379 A2 HR P20030379A2 HR 20030379 A HR20030379 A HR 20030379A HR P20030379 A HRP20030379 A HR P20030379A HR P20030379 A2 HRP20030379 A2 HR P20030379A2
- Authority
- HR
- Croatia
- Prior art keywords
- propyl
- piperidine
- methoxyquinolin
- carboxylic acid
- chloro
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 62
- 238000002360 preparation method Methods 0.000 title description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 1022
- 239000002253 acid Substances 0.000 claims description 786
- -1 cyano, carboxyl Chemical group 0.000 claims description 285
- 238000000034 method Methods 0.000 claims description 71
- 238000006243 chemical reaction Methods 0.000 claims description 58
- 230000009471 action Effects 0.000 claims description 50
- 229910052757 nitrogen Inorganic materials 0.000 claims description 46
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 125000002950 monocyclic group Chemical group 0.000 claims description 33
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 26
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 25
- 229910052705 radium Inorganic materials 0.000 claims description 23
- 229910052701 rubidium Inorganic materials 0.000 claims description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 18
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 229910003827 NRaRb Inorganic materials 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical group 0.000 claims description 10
- 125000004468 heterocyclylthio group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- AFUHYRRQNQUTQH-UHFFFAOYSA-N 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(3,5-difluorophenoxy)ethyl]piperidine-4-carboxylic acid Chemical group C12=CC(OC)=CC=C2N=CC(Cl)=C1CCCC(CC1)(C(O)=O)CCN1CCOC1=CC(F)=CC(F)=C1 AFUHYRRQNQUTQH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 4
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical group [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- KXLQEEVGEUPIQR-UHFFFAOYSA-N 1-(2-cyclopentylsulfanylethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylic acid Chemical group C12=CC(OC)=CC=C2N=CC(F)=C1CCCC(CC1)(C(O)=O)CCN1CCSC1CCCC1 KXLQEEVGEUPIQR-UHFFFAOYSA-N 0.000 claims description 2
- RAWWZDRAVRVSQD-UHFFFAOYSA-N 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(2-thiophen-2-ylsulfanylethyl)piperidine-4-carboxylic acid Chemical group C12=CC(OC)=CC=C2N=CC(Cl)=C1CCCC(CC1)(C(O)=O)CCN1CCSC1=CC=CS1 RAWWZDRAVRVSQD-UHFFFAOYSA-N 0.000 claims description 2
- 229910020587 CmF2m+1 Inorganic materials 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- LTVOKYUPTHZZQH-UHFFFAOYSA-N difluoromethane Chemical group F[C]F LTVOKYUPTHZZQH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000004660 phenylalkylthio group Chemical group 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 483
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 444
- JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 description 349
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 201
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 172
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 100
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- 150000003254 radicals Chemical class 0.000 description 52
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- 239000011541 reaction mixture Substances 0.000 description 43
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 41
- 239000002904 solvent Substances 0.000 description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
- 239000002585 base Substances 0.000 description 29
- 238000003756 stirring Methods 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 26
- YFNOTMRKVGZZNF-UHFFFAOYSA-N 2-piperidin-1-ium-4-ylacetate Chemical compound OC(=O)CC1CCNCC1 YFNOTMRKVGZZNF-UHFFFAOYSA-N 0.000 description 24
- 238000010992 reflux Methods 0.000 description 22
- 150000001408 amides Chemical class 0.000 description 21
- 150000003053 piperidines Chemical class 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 239000012442 inert solvent Substances 0.000 description 19
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000012298 atmosphere Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 17
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 238000004587 chromatography analysis Methods 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- 229960001866 silicon dioxide Drugs 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 13
- 229910052794 bromium Inorganic materials 0.000 description 13
- 239000002609 medium Substances 0.000 description 13
- 239000002245 particle Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 230000007062 hydrolysis Effects 0.000 description 12
- 238000006460 hydrolysis reaction Methods 0.000 description 12
- 238000002329 infrared spectrum Methods 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 239000012312 sodium hydride Substances 0.000 description 11
- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 229910052740 iodine Chemical group 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 235000011181 potassium carbonates Nutrition 0.000 description 10
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 9
- 150000008046 alkali metal hydrides Chemical class 0.000 description 9
- QYXBHUXYBFINKI-UHFFFAOYSA-N benzyl 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate Chemical compound C12=CC(OC)=CC=C2N=CC(Cl)=C1CCCC1(C(=O)OCC=2C=CC=CC=2)CCNCC1 QYXBHUXYBFINKI-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- 150000002825 nitriles Chemical class 0.000 description 8
- 125000005270 trialkylamine group Chemical group 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 6
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 241001484259 Lacuna Species 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000011630 iodine Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 description 6
- SRJOCJYGOFTFLH-UHFFFAOYSA-M piperidine-4-carboxylate Chemical compound [O-]C(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-M 0.000 description 6
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 6
- 239000000052 vinegar Substances 0.000 description 6
- 235000021419 vinegar Nutrition 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000002198 insoluble material Substances 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- FOOVEGXEARQUBR-UHFFFAOYSA-N 1-o-tert-butyl 4-o-ethyl 4-prop-2-enylpiperidine-1,4-dicarboxylate Chemical compound CCOC(=O)C1(CC=C)CCN(C(=O)OC(C)(C)C)CC1 FOOVEGXEARQUBR-UHFFFAOYSA-N 0.000 description 4
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 4
- UXSHMFZAQNCVGK-UHFFFAOYSA-N 4-bromo-3-chloro-6-methoxyquinoline Chemical compound N1=CC(Cl)=C(Br)C2=CC(OC)=CC=C21 UXSHMFZAQNCVGK-UHFFFAOYSA-N 0.000 description 4
- PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 description 4
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo(3.3.1)nonane Chemical compound C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
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- JSRWIUFTLZUBGQ-UHFFFAOYSA-N n-hydroxy-4-[3-[6-methoxy-3-(morpholin-4-ylmethyl)quinolin-4-yl]propyl]-1-[3-(2,4,6-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxamide Chemical compound C1CN(CC#CC=2C(=CC(F)=CC=2F)F)CCC1(C(=O)NO)CCCC=1C2=CC(OC)=CC=C2N=CC=1CN1CCOCC1 JSRWIUFTLZUBGQ-UHFFFAOYSA-N 0.000 description 1
- QUGYRDJGZGZKFE-UHFFFAOYSA-N n-hydroxy-4-[3-[6-methoxy-3-(morpholin-4-ylmethyl)quinolin-4-yl]propyl]-1-[3-(2,4,6-trifluorophenyl)propyl]piperidine-4-carboxamide Chemical compound C1CN(CCCC=2C(=CC(F)=CC=2F)F)CCC1(C(=O)NO)CCCC=1C2=CC(OC)=CC=C2N=CC=1CN1CCOCC1 QUGYRDJGZGZKFE-UHFFFAOYSA-N 0.000 description 1
- NJSJTXHTSLBQAJ-UHFFFAOYSA-N n-hydroxy-4-[3-[6-methoxy-3-(morpholin-4-ylmethyl)quinolin-4-yl]propyl]-1-[3-(3,4,5-trifluorophenyl)prop-2-ynyl]piperidine-4-carboxamide Chemical compound C1CN(CC#CC=2C=C(F)C(F)=C(F)C=2)CCC1(C(=O)NO)CCCC=1C2=CC(OC)=CC=C2N=CC=1CN1CCOCC1 NJSJTXHTSLBQAJ-UHFFFAOYSA-N 0.000 description 1
- LCRYXDSGIGQOJC-UHFFFAOYSA-N n-hydroxy-4-[3-[6-methoxy-3-(morpholin-4-ylmethyl)quinolin-4-yl]propyl]-1-[3-(3,4,5-trifluorophenyl)propyl]piperidine-4-carboxamide Chemical compound C1CN(CCCC=2C=C(F)C(F)=C(F)C=2)CCC1(C(=O)NO)CCCC=1C2=CC(OC)=CC=C2N=CC=1CN1CCOCC1 LCRYXDSGIGQOJC-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical group CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- OKBFGTWWLUZIOE-UHFFFAOYSA-M sodium 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-heptylpiperidine-4-carboxylate Chemical compound [Na+].ClC=1C=NC2=CC=C(C=C2C=1CCCC1(CCN(CC1)CCCCCCC)C(=O)[O-])OC OKBFGTWWLUZIOE-UHFFFAOYSA-M 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- FNXKBSAUKFCXIK-UHFFFAOYSA-M sodium;hydrogen carbonate;8-hydroxy-7-iodoquinoline-5-sulfonic acid Chemical class [Na+].OC([O-])=O.C1=CN=C2C(O)=C(I)C=C(S(O)(=O)=O)C2=C1 FNXKBSAUKFCXIK-UHFFFAOYSA-M 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 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
- 150000003892 tartrate salts Chemical class 0.000 description 1
- IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 description 1
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 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
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- PBIMIGNDTBRRPI-UHFFFAOYSA-N trifluoro borate Chemical compound FOB(OF)OF PBIMIGNDTBRRPI-UHFFFAOYSA-N 0.000 description 1
- UFXIRMVZNARBDL-UHFFFAOYSA-N trifluoro(morpholin-4-yl)-$l^{4}-sulfane Chemical compound FS(F)(F)N1CCOCC1 UFXIRMVZNARBDL-UHFFFAOYSA-N 0.000 description 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
- RIFYBBXGYKFBFC-UHFFFAOYSA-K trisodium;thiophosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=S RIFYBBXGYKFBFC-UHFFFAOYSA-K 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Chemical group 0.000 description 1
- 239000008096 xylene Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (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)
Description
Prikazani izum se odnosi na heterociklilalkilpiperidinske derivate opće formule:
[image]
koji djeluju kao antimikrobna sredstva. Izum se isto tako odnosi na postupak njihova pripravljanja i pripravke koji iz sadržavaju.
Patentna prijava W0 99/37635 i W0 00/43383 prikazuju antimikrobne derivate kinolinilpropilpiperidina opće formule:
[image]
u kojoj radikal ri osobito predstavlja (Cl-6) alkoksi, R2 je vodik, R3 je na položajima -2 i -3 i predstavlja (Cl-6) alkil koji može po izboru biti supstituiran jednim do tri supstituenata odabranih između tiola, halogena, alkiltio, trifluorometila, karboksila, alkiloksikarbonila, alkilkarbonila, alkeniloksikarbonila, alkenilkarbonila, hidroksil po izboru supstituiran alkilom, itd., R4 predstavlja skupinu –CH2R5 u kojoj je rs odabran između alkila, hidroksialkila, alkenila, alkinila, tetrahidrofurila, po izboru supstituiranog fenilalkila, po izboru supstituiranog fenilalkenila, po izboru supstituiranog heteroarilalkila, po izboru supstituiranog heteroarila, itd., n predstavlja 0 do 2, m je 1 ili 2 i A i B posebno predstavljaju kisik, sumpor, sulfinil, sulfonil, NR11, CR6R7 u kojima R6 i R7 predstavljaju H, tiol, alkiltio, halo, trifluorometil, alkenil, alkenilkarbonil, hidroksi, amino, a Z1 i Z2 su N ili CR1a, itd. Navedeni produkti pokazuju antimikrobnu aktivnost. Unatoč tome, niti jedan disupsituirani derivat na položaju -4 piperidina nije bio sintetiziran, stoga i posljedično tome nije niti otkrivena biološka aktivnost navedenih produkata.
Budući da blage modifikacije poznate strukture mogu rezultirati velikim brojem varijacija aktivnosti, nije bilo očito da derivati disupstituirani na položaju -4 piperidina bi isto tako mogli imati antibakterijsko djelovanje.
Europska patentna prijava EP 30044 prikazuje derivate kinolina koji se koriste kao kardiovaskularni agensi, a odgovaraju općoj formuli:
[image]
u kojoj R1 predstavlja posebno alkiloksi, A-B je -CH2-CH2-, -CHOH-CH2-, -CH2-CHOH-, -CH2-CO- ili -CO-CH2-, R1 predstavlja H, OH ili alkiloksi, R2 je etil ili vinil, R3 je posebno alkil, hidroksialkil, cikloalkil, hidroksil, alkenil, alkinil, tetrahidrofuril, fenilalkil, po izboru supstituirani difenilalkil, po izboru supstituirani fenilalkenil, po izboru susptituirani benzoil ili benzoilalkil, po izboru supstituirani heteroaril ili heteroarilalkil, a Z predstavlja H ili alkil ili oblike s R3 cikloalkilnim radikalom.
Zabilježeno je, a to je i tema prikazanog izuma, da produkti opće formule (I) u kojima:
X1, X2, X3, X4 i X5 predstavljaju od >C-R'1 do >C-R'5, ili na drugi način, najviše jedan među njima predstavlja atom dušika,
R1, R'1, R'2, R'3, R'4 i R'5 su identični ili različiti i predstavljaju vodik ili halogeni atom ili alkil, cikloalkil, fenil, feniltio, mono- ili biciklički aromatski heterociklil ili heterocikliltio, hidroksi. alkiloksi, trifluorometoksi, alkiltio, trifluorometiltio, cikloalkiloksi, cikloalkiltio, cijano, karboksil, alkiloksikarbonil, cikloalkiloksikarbonil, -NraRb ili -CONRaRb radikal (u kojem Ra i Rb mogu predstavljati vodik, alkil, cikloalkil, fenil, mono- ili biciklički aromatski heterociklil ili Ra i Rb tvore, zajedno sa atomom dušika na koji su vezani, 5- ili 6-člani heterociklički prsten koji može po izboru sadržavati drugi heteroatom odabran između O, S i N, te, kada je prikladno, nose alkil, fenil ili mono- ili biciklički aromatski heterociklil supstituiran na dušikovom atomu, ili gdje je prikladno, atom sumpora koji je oksidiran u obliku sulfinila ili sulfonila), ili predstavlja metilenski radikal supstituiran s fluoro, hidroksil, alkiloksi, alkiltio, cikloalkiloksi, cikloalkiltio, fenil, mono- ili biciklički aromatski heterociklil, karboksil, alkiloksikarbonil, cikloalkiloksikarbonil, -NRaRb ili -CONRaRb u kojima Ra i Rb su u skladu s prethodn onavedenom definicijom, ili predstavljaju fenoksi, heterocikliloksi, benziloksi, heterociklilmetiloksi, ili na drugi način ri može isto tako predstavljati difluorometoksi, ili radikal strukture -CmF2m+1, SCmF2m+1, ili -OCmF2m+1 u kojima je m cijeli broj između 1 i 6, ili na drugi način R's može isto tako predstavljati trifluoroacetil.
R2 predstavlja karboksil, alkiloksikarbonil, cikloalkiloksikarbonil, cijano, -CONRaRb (u kojem Ra i Rb predstavljaju, odnosno su, vodik, alkil, cikloalkil, fenil, mono- ili biciklički aromatski heterociklil, ili Ra ili Rb predstavljaju hidroksil, alkiloksi, cikloalkiloksi, ili Ra i Rb tvore, zajedno s atomom dušika na koji su vezani, 5- ili 6-člani heterociklički prsten koji može po izboru sadržavati drugi heteroatom odabran između O, S i N, te kada je prikladno, nosi alkil, fenil, ili mono- ili biciklički aromatski heterociklil supstituiran na atomu dušika ili, kada je prikladno, atom sumpora koji je oksidiran u obliku sulfinila ili sulfonila), ili R2 predstavlja hidroksimetil, alkil koji sadrže 1 ili 2 atoma ugljika supstituiranih karboksilom, alkiloksikarbonilom, cikloalkiloksikarbonilom, cijano ili -CONRaRb u kojem su Ra i Rb kao što su prethodno definirani, ili R2 predstavlja radikal strukture -CF2-Rc, -C(CH3)2-Rc u kojem je Rc karboksil, alkilokisarbonil, cikloalkiloksikarbonil, ili -CONRaRb u kojem Ra i Rb su definirani kao što je prethodno navedeno.
R3 predstavlja fenil, mono- ili biciklički aromatski heterociklil ili alk-R°3 radikal u kojem alk označava alkilni radikal i R°3 r predstavlja vodik, halogen, hidroksil, alkiloksi, alkiltio, alkilsulfinil, akilsulfonil, alkilamino, dialkilamino, cikloalkil, cikloalkiloksi, cikloalkiltio, cikloalkilsufinil, cikloalkilsulfonil, cikloalkilamino, N-cikloalkil-N-alkilamino, -N-(cikloalkil)2, acil, cikloalkilkarbonil, fenil, fenoksi, feniltio, fenilsulfinil, fneilsulfonil, fenilamio, N-alkil-N-fenilamino, N-cikloalkil-N-fenilamino, -N-(fenil)2, fenilalkiloksi, fenilalkiltio, fenilalkilsulfinil, fenilalkilsulfonil, fenilalkilamino, N-alkil-N-fenilaminoalkil, N-cikloalkil-N-fenilalkilamino, benzoil, mono- ili biciklični aromatski heterociklil, heterocikliloksi,heterocikliltio, heterociklilsulfinil, heterociklilsulfonil, heterociklilamino, N-alkil-N-heterociklilamino, N-cikloalkil-N-heterocikloilamino, heterociklilkarbonil, heterociklilalkiloksi, heterociklilalkiltio, heterociklilalkilsulfinil, heterociklilamlkilsulfonil, heterociklilalkilamino, N-alkil-N-heterociklilaminoalkil, N-cikloalkil-N-heterociklilaminoalkil, (prethodno navedeni heterociklički dijelovi se odnose na mono-ili bicikličke aromatske spojeve), karboksil, alkiloksikarbonil, -NraRb ili -CO-NraRb u kojima Ra i Rb su u skladu s prethodno navedenom definicijom za R2, ili na drugi način R°3 predstavlja -CR'b=CR'c-R'a u kojem je R'a fenil, fenilalkil, heterociklil ili heterociklilalkil u kojem heterociklički dio predstavlja mono- ili biciklički aromatski spoj,fenoksialkil, feniltioalkil, fenilsulfinilalkil, fenilsulfonilalkil, fenilaminoalkil, N-alkil-N-fenilaminoalkil, heterocikliloksialkil, heterocikliltioalkil, heterociklilsulfinilalkil, heterociklilsulfonilalkil, heterociklilaminoalkil, N-alkil-N-heterociklilaminoalkil, heterocikliltio, heterociklilsulfinil, heterociklilsulfonil, (prethodno navedeni heterociklički dijelovi predstavljaju mono- ili biciklički aromatski spoj), feniltio, fenilsulfinil, fenilsulfonil, te u kojima R'b i R1c predstavljaju vodik, alkil ili cikloalkil, ili na drugi način R°3 predstavlja radikal -C≡C-Rd u kojem Rd predstavlja alkil, fenil, fenilalkil, fenoksialkil, feniltioalkil, N-alkil-N-fenilaminoalkil, mono- ili biciklički aromatski heterociklil, heterociklilalkil, heterocikliloksialkil, heterocikliltioalkil, heterociklilaminoalkil, N-alkil-N-heterociklilaminoalkil, (prethodno navedeni heterociklički dijelovi predstavljaju mono- ili biciklički aromatski spoj), ili na drugi način R°3 predstavlja -CF2-fenil ili mono- ili biciklički aromatski –CF2-heterociklilni radikal,
Y predstavlja radikal >CH-Re u kojem Re predstavlja vodik, fluoro, hidroksil, alkiloksi, cikloalkiloksi, karbonil, alkiloksikarbonil, cikloalkiloksikarbonil, -NRaRb ili -CO-NraRb u kojem Ra i Rb su u skladu s prethodno navedenom definicijom za R2, ili jedan predstavlja atom vodika, a drugi je alkiloksikarbonil, akril, cikloalkilkarbonil, benzoil ili heterociklilkarbonilni radikal u kojem je heterociklički dio mono- ili biciklički aromatski spoj, ili na drugi način Y predstavlja difluorometilen, karbonil, hidroksiiminometilen, alkiloksiiminometilen ili cikloalkiloksiiminometilenski radikal ili 1,1-ciklo-alkilenski radikal koji sadrži 3 do 6 atoma ugljika, a n je cijeli broj od 0 do 4 i podrazumijeva se da fenil, benzil, benzoil ili heterociklilni radikali ili prethodno navedeni dijelovi mogu po izboru biti supstituirani na prstenu s 1 do 4 supstituenata odabrana između halogena, hidroksi, alkila, alkiloksi, alkiloksialkila, haloalkila, trifluorometila, trifluorometoksi, trifluorometiltio, karbonila, alkiloksikarbonila, cijano, alkilamino, -NRaRb u kojem Ra i Rb su u skladu s prethodno navedenom definicijom, fenil, hidroksialkil, alkiltioalkil, alkilsulfinilalkil i alkilsulfonilalkil, u njihovim enantiomerskim ili dijastereoizomeričnim oblicima ili smjese navedenih oblika, i/ili, gdje je prikladno, u njihovom sin ili anti obliku ili njegovoj smjesi, kao i njihove soli, smatraju se snažnim antibakterijskim sredstvima.
Smatra se da alkilni ili acilni radikali i dijelovi sadrže (osim gdje je izričito navedeno) l do 10 atoma ugljika u ravnom ili razgranatom lancu, te da cikloalkilni radikali sadrže od 3 do 6 atoma ugljika.
Isto tako se smatra da radikali koji predstavljaju ili nose halogeni atom prikazuju halogen odabran između fluora, klora, broma i joda, prikladno fluora.
U gore navedenoj općoj formuli, kada radikali predstavljaju mono- ili biciklički aromatski heterociklički supstituent, navedeni supstituent sadrži 5 do 10 članova lanca i može biti odabran (na neograničavajući način) između tienila,furila, pirolila, imidazolila, tiazolila, oksazolila, tiadiazolila, oksadiazolila, tetrazolila, piridila, piridazinila, pirazinila, pirimidinila, indolila, benzotienila, benzofuril indazolila, benzotiazolila, naftiridinila, kinolila, izokinolila, cinolila, kvinazolila, kvinoksalila, benzoksazolila i benzimidazolila koji mogu po izboru biti supstituirani prethodno navedenim supstituentima.
U skladu s izumom, produkti opće formule (I) mogu se dobiti vezanjem lanca R3 s heterociklilalkilpiperidinskim derivatom opće formule:
[image]
u kojoj X1, X2, X3, X4, X5, R1, R2, Y i n su definirani kao što je prethodno navedeno, a Ra je zaštićen kada nosi karboksilni ili amino radikal, po izboru uz uklanjanje kisele-zaštitne skupine ili amino-zaštitnog radikala, po izboru odvajanjem enanatiomerskih ili dijastereoizomeričnih oblika i/ili, gdje je prikladno, sin i anti oblika i po izboru pretvorbom dobivenog produkta u sol.
Vezanje lanca R3 s piperidinom se povoljno izvodi djelovanjem derivata opće formule:
R3-X (IIa)
u kojoj je R3 definiran kao što je prethodno navedeno, a X predstavlja halogeni atom, metilsulfonilni radikal, trifluorometilsulfonilni radikal ili p-toluensulfonilni radikal, radeći u anhidroznom mediju, koji je po izboru inertan (na primjer dušik ili argon) u organskom solventu kao što je amid (na primjer dimetilformamid), keton (na primjer aceton) ili nitril (na primjer acetonitril) u prisustvu baze kao što je organodušična baza (na primjer trietilamin) ili mineralna baza (alkalni karbonat, na primjer kalijev karbonat) na temperaturi između 20°C i refluksne temperature solventa. Smatra se da dušikov atom iz piperidina u derivatu opće formule (II) je po izboru zaštićen u skladu s uobičajenim postupcima koji ne utječu na ostatak molekule ili reakciju; na primjer, zaštita se sprovodi zaštitom odabranog radikala između t-butoksikarbonila i benziloksikarbonila.
Prikladno, derivat opće formule (IIa) u kojem X predstavlja atom broma ili joda je reagirao.
Kada R3 predstavlja fenilni radikal, moguće je djelovanje na jodo ili bromo derivatu R3 -X u prisustvu paladijeva katalizatora u skladu s postupkom opisanim u J.Org.Chem., 6066 (1997) ili Tet. Lett., 6359 (1997). Paladijev katalizator se može odabrati između tris(dibenzilidenaceton)dipaladija i paladij diacetata s ligandom kao što je 2,2'-bis(difenil-fosfino)-1,1’-binaftil ili 2-(di-t-butilfosfinol)-bifenil, na primjer, baze kao što je natrijev terc-butoksid ili cezijev karbonat u solventu kao što je tetrahidrofuran, tetraglim ili toluen, po izboru u prisustvu etera kao što je 18-C-6 (1, 4, 7, 10, 13, 16-heksaoksaciklooktaden). Reakcija se sprovodi na temepraturi između 20°C i 110°C.
Kada Ra predstavlja radikal -alk-R°3 u kojem alk predstavlja alkilni radikal, a R°3 je -C≡C-Rd u kojem Rd predstavlja fenil, fenilalkil, heterociklil ili mono- ili biciklički aromatski heterociklilalkil, često je prikladno vezati alkilni halid: HC≡C-alk-X u kojem alk je u skladu s gore navedenom definicijom, a X predstavlja halogeni atom, a zatim supstituirati lanac fenilnim, fenilalkilnim, heterociklilnim ili heterociklilalkilnim radikalom.
U navedenoj alternativi dodatak alkilnog lanca je izvršen primjenom alkinilnog halida HC≡C-alk-X u kojem je X u povoljnom slučaju atom broma, u uvjetima koji su prethodno navedeni za vezanje lanca Ra, u prisustvu ili odsustvu alkalijskog metala jodida kao što je, na primjer, kalijev jodid ili natrijev jodid.
Supstitucija fenilnim ili heterociklilnim radikalom se sprovodi djelovanjem halida porijeklom iz cikličkog radikala koji će biti supstituiran, u prisustvu trietilamina, u anhidroznom mediju, u solventu kao što je amid (na primjer dimetilformamid) ili nitril (na primjer acetonitril) i u prisustvu paladijeve soli kao što je na primjer, tetrakis(trifenilfosfin)paladij i bakreni jodid, na temperaturi između 20°C i refluksne temperature solventa.
Supstitucija fenilnim alkilnim ili heterociklilalkilnim radikalom sprovedena je djelovanjem odgovarajućeg halida, u bazičnom mediju, na primjer u prisustvu kalijeva hidrida ili natrijeva hidrida ili n-butillitija, u solventu kao što je eter (tetrahidrofuran) ili amid (dimetilformamid) na temperaturi između -60°C i temperature vrenja reakcijskog medija.
Potrebno je shvatiti da ako alkilni radikali prikazani s R3 nose karboksilne ili amino supstituente, navedeni supstituenti su prvo zaštićeni, a zatim oslobođeni nakon reakcije. Postupak se izvodi u skladu s uobičajenim postupcima koji ne utječu na ostatak molekule, osobito u skladu s postupcima opisanim u T.W. Greene i P.G.M. Wuts, Zaštitne skupine u organskoj sintezi (2nd edition), A. Wiley -Interscience Publication (1991), od McOmie, Zaštitne skupine u organskoj kemiji, Plenum Press (1973).
Zaštićeni karboksilni radikal nastao iz R2 može se odabrati iz estera podložnih hidrolizi. Primjeri koji su navedeni obuhvaćaju metil, benzil i terc-butil estere, ili fenil propil ili alil estere. Zaštita karboksilnog radikala je po izboru sprovodi istovremeno s reakcijom.
Kada je prikladno, amino radikal je zaštićen uobičajenim postupcima, prethono navedenim za R3.
Kada R3 predstavlja radikal -alk-R°3 u kojem alk predstavlja alkilni radikal, a R°3 predstavlja fenoksi, feniltio, fenilamino, heterocikliloksi, heterocikliltio ili heterociklilamino radikal u kojem je heterociklični dio aromatski, poželjno je konstruirati lanac korak po korak, prvo kondenzacijom lanca HO-alk-X, u kojem je X halogeni atom, prikladno jod, pod prethodno opisanim uvjetima za reakciju produkta opće formule (IIa), a zatim pretvorbom hidroksialkilnog lanca u haloalkil, metansulfonilalkil ili p-toluensulfonilalkilni lanac, te na kraju reakcijom, u bazičnom mediju, aromatskog derivata strukture Ar-ZH u kojem AR predstavlja aromatski fenil ili heterociklilni radikal, a Z je sumpor, kisik ili atom dušika.
Pretvorba hidroksiliranog lanca u haloalkil ili p-toluensulfonilni lanac se sprovodi u skladu s uobičajenim postupcima halogenacije ili sulfonilacije, ososbito reakcijom halogeniranog agensa, na primjer, tionilnog klorida, halofosfornih derivata: na primjer fosfornog triklorida ili tribromida ili sulfonilirajućeg agensa kao što je, na primjer, metansulfonilni klorid, p-toluensulfonilni klorid ili trifluorometansulfonski anhidrid. Reakcija se izvodi u organskom solventu, na primjer kloriranom solventu (na primjer diklorometanu ili kloroformu), na temperaturi između 0°C i 60°C. U određenim slučajevima, prednost je da se reakcija odvija u prisustvu baze, na primjer piridina ili trietilamina.
Reakcija aromatskih derivata Ar-ZH se u povoljnom slučaju izvodi kao što je gore opisano za djelovanje derivata opće formule (Ha), u prisustvu baze, na primjer kao što je dušikova baza, u organskom solventu kao što je amid (na primjer dimetilformamid), keton (na primjer aceton) ili nitril (na primjer acetonitril), u prisustvu baze kao što je dušikova organska baza (na primjer trietilamin) ili mineralna baza (karbonat alkalijskog metala: na primjer kalijev karbonat) na temperaturi između 20°C i temperature refluksa reakcijske smjese. Prednost je da se reakcija odvija u prisustvu kalijeva jodida.
U skladu s izumom, heterociklilakilpiperidinski derivati opće formule (II) mogu se pripraviti u skladu s posutpkom vezanja koji je opisan u tekstu koji slijedi, a zatim prikladno su konvertirani u skladu s jednim od opisanih postupaka (1) do (9), putem reakcija u slijedu koje počinju s jedim od prethodno dobivenih derivata opće formule (II), kako bi se pripravili derivati koji odgovaraju različitim alternativama Y i/ili R1, R'1, R'2, R'3, R'4 ili R'5.
Podrazumijeva se da u slučaju kada radikali karboksilne kiseline su prisutni na molekuli, navedeni radikali su prethodno zaštićeni, a zatim oslobođeni nakon reakcije u skladu s uobičajenim postupcima koji ne utječu na ostatak molekule, osobito u skladu s postupcima navedenim u gore navedenim referencama. Isto tako se podrazumijeva da u reakcijama koje mogu interferirati s aminom piperidina u derivatu opće formule (II), navedeni amin je zaštićen, a zatim oslobođen nakon reakcije. Zaštita se izvodi u skladu s uobičajenim postupcima, kao što je prethodno specificirano, osobito putem t-butoksikarbonil ili benziloksikarbonilnog radikala.
U skladu s izumom, pripravljanje produkata opće formule (II) u kojoj Re u Y predstavlja atom vodika, izvodi se vezanjem heterocikličnog derivata opće formule:
[image]
u kojoj R1, X1, X2, X3, X4 i X5 su kao što je prethodno definirano, a Ha1 predstavlja halogeni atom, s piperidinskim derivatom opće formule:
[image]
u kojoj Rz predstavlja zaštitni radikal, a R''2 je definiran kao što je gore navedeno ili predstavlja zaštićeni radikal ako R2 predstavlja ili nosi funkciju karboksilne kiseline, a zatim slijedi uklanjanje zaštitnih radikala i/ili slijedi pretvorba, putem slijedeće operacije, supstituenata bicikličnog ili heterociklilalkilpiperidinskog derivata opće formule (II) na taj način dobivene, do nastanka očekivanog derivata koji nosi radikal R1, R'1, R'2, R'3, R'4 ili R'5, te kada je prikladno, uklanjanje zaštitnih radikala koji su još uvijek prisutni na molekuli.
Radikal Rz može predstavljati bilo koju zaštitnu skupinu za atom dušika koji je kompatibilan s reakcijom (na primjer t-butiloksikarbonil ili benziloksikarbonil). Zaštitne skupine za funkcije kiseline odabrane su iz uobičajenih skupina čiji unos i uklanjanje ne utječu na ostatak molekule, osobito navedenih u prethodno citiranim referencama.
Reakcija se izvodi djelovanjem u slijedu prvo organobora (na primjer 9-borabiciklo-[3.3.1]nonana) u solventu kao što je eter (na primjer tetrahidrofuran ili dioksan) na temperaturi između -20°C i 20°C, a zatim bicikličkog derivata opće formule (III) u kojem Ha1 u prikladnom slučaju predstavlja atom broma ili joda ili atom klora, u skladu s postupcima opisanim u Suzuki i sur., Čista i primijenjena kemija, 57, 1749 (1985). Reakcija se općenito izvodi u prisustvu paladijeve soli (na primjer difenilfosfinoferocenpaladijeva klorida) i baze kao što je kalijev fosfat, na temperaturi između 20°C i temperature refluksa solventa.
1) Heterociklilalkilpiperidini opće formule (II) u kojoj Re u Y predstavlja hidroksilni radikal mogu se pripraviti oksidacijom u bazičnom mediju odgovarajućegheterociklilalkilpiperidinskog derivata opće formule (II) u kojoj Re u Y predstavlja atom vodika. Oksidacija se izvodi djelovanjem kisika, prikladno u inertnom solventu kaošto je dimetil sulfoksid u prisustvu terc-butanola i baze kao što je kalijev terc-butoksid ili natrijev terc-butoksid na temperaturi između 0°C i 100°C.
Heterociklilalkilpiperidinski derivat u kojem Re u Y predstavlja atom fluora pripravlja se fluorinacijom počevši s derivatom u kojem Re predstavlja hidroksilnu skupinu. Reakcija se izvodi u prisustvu sumpornog fluorida [na primjer u prisustvu aminosumpornog trifluorida (dietilaminosumpornog fluorida (Tetrahedron, £4, 2875 (1988), bis(2-metoksietil)amino-sumporni trifluorid (Deoxofluor®), ili morfolinosumpornog trifluorida, na primjer) ili na drugi način u prisustvu sumpornog tetrafluorida (J. Org. Chem., 40, 3808 (1975)]; na drugi način, reakcija fluorinacije se isto tako može izvesti primjenom fluorinirajućeg agensa kao što je heksafluoropropildietilamin (JP 2 039 546) ili N-(2-kloro-1,l,2-trifluoroetil)dietilamina.
Postupak se izvodi u organskom solventu kao što je klorirani solvent (na primjer diklorometan, dikloroetan ili kloroform) ili u eteru (na primjer tetrahidrofuran ili dioksan) na temperaturi između -78°C i 40°C (prikladno između 0°C i 30°C). Prednost ima izvođenje reakcije u inertnom solventu (osobito argon ili dušik).
Heterociklilalkilpiperidinski derivat opće formule (II) u kojem Re u Y predstavlja alkiloksi ili cikloalkiloksi radikal pripravlja se djelovanjem alkilnog ili cikloalkilnog halida na odgovarajući derivat opće formule (II) u kojem Re predstavlja hidroksilnu skupinu. Reakcija se općenito izvodi primjenom broma ili klora, u inertnom solventu kao što je N,N-dimetilformamid ili dimetil sulfoksid, u prisustvu kiselinskog receptora kao što je trialkilamin (na primjer trietilamin) ili hidrida alkalijskog metala (na primjer natrijeva hidrida), na temperaturi između 20°C i 100°C.
Heterociklilalkilpiperidinski derivat opće formule (II) u kojem Y predstavlja karbonilni radikal može se pripraviti oksidacijom odgovarajućeg derivata opće formule (II) u kojem Re u Y predstavlja hidroksilni radikal. Navedena oksidacija je izvodi, na primjer, primjenom kalijeva permanganata po izboru u otopini natrijeva hidroksida (na primjer 3N natrijev hidroksid), na temperaturi između -20°C i 20°C, ili na drugi način djelovanjem oksalilnog klorida u prisustvu dimetil sulfoksida, te potom dodavanjem amina kao što je trietilamin ili dimetil sulfoksid, na temperaturi između -60°C i 20°C, analogno postupku opisanom u D. Swern i sur., J. Org. Chem., 44, 4148 (1979).
Heterociklilalkilpiperidinski derivat opće formule (II) u kojem Y predstavlja difluorometilenski radikal mogu se pripraviti dihalogenacijom produkta opće formule (II) u kojoj Y predstavlja karbonil, u uvjetima analognim onima za prethodno opisanu fluorinaciju.
Heterociklilalkilpiperidinski derivat opće formule (II) u kojoj Y predstavlja hidroksiimino-metilenski radikal može se pripraviti djelovanjem hidroksilamina na derivat opće formule (II) u kojoj Y predstavlja karbonilni radikal. Reakcija se općenito izvodi u inertnom solventu kao što je alkohol (metanol ili etanol) i po izboru u prisustvu natrijeva hidroksida (na primjer 1N natrijeva hidroksida), na temperaturi između 0°C i točke vrenja reakcijske smjese.
Heterociklilalkilpiperidinski derivat opće formule (II) u kojem Y predstavlja alkiloksiiminometilen ili cikloalkiloksiiminometilenski radikal može se pripraviti djelovanjem alkilnog ili cikloalkilnog halida na odgovarajući derivat opće formule (II) u kojoj Y predstavlja hidroksiiminometilen. Reakcija se općenito izvodi u inertnom solventu kao što je N,N-dimetilformamid ili dimetil sulfoksid, u prisustvu kiselog akceptora kao što je trialkilamin (na primjer trietilamin) ili hidrida alkalijskog metala (na primjer natrijeva hidrida), na temperaturi između 20°C i 100°C. Prikladno se koristi bromid.
Heterociklilalkilpiperidinski derivat opće formule (II) u kojem Re u Y predstavlja radikal -NRaRb može se pripraviti iz odgovarajućeg toziloksi derivata djelovanjem amina HNRaRb (ili, gdje je prikladno, amonijaka kada Re predstavlja -NH2) u inertnom solventu kao što je N,N-dimetilformamid ili dimetil sulfoksid, na temperaturi između 20°C i točke vrenja reakcijske smjese. Kada je amonijak odreagirao, postupak se prikladno izvodi pod tlakom (2 do 20 atmosfera) na temperaturi između 20°C i 100°C. Kada se postupak izvodi primjenom amina HNRaRb, reakcija se po izboru odvija u prisustvu baze kao što je trialkilamin (na primjer trietilamin), piridin ili hidrida alkalijskog metala (na primjer natrijeva hidrida). Derivat u kojem Re u Y predstavlja toziloksi dobiven je iz produkta opće formule (II) u kojem Re u Y predstavlja hidroksil, djelovanjem tozilnog klorida u piridinu, na temperaturi između -10°C i 20°C.
Heterociklilalkilpiperidinski derivat opće formule (II) u kojoj Re u Y predstavlja karboksilni radikal može se pripraviti djelovanjem alkalijskog cijanida na odgovarajući toziloksi derivat, u organskom solventu kao što je dimetilformamid ili dimetil sulfoksid ili u vodeno-organskom mediju, na primjer smjesi voda-alkohol, na temperaturi između 0°C i točke vrenja reakcijske smjese, a zatim hidrolizom dobivenog nitrila djelovanjem snažne kiseline kao što je klorovodična kiselina, te po izboru nižeg alifatskog alkohola, na temperaturi između 0°C i točke vrenja reakcijske smjese. Natrijev cijanid ili kalijev cijanid se prikladno koriste.
Heterociklilalkilpiperidinski derivat opće formule (II) u kojem Re u Y predstavlja alkiloksikarbonil ili cikloalkiloksikarbonil ili -CO-NRaRb radikal mogu se pripraviti djelovanjem, osobito, alkohola ili odgovarajućeg amina na derivat opće formule (II) u kojem Re u Y predstavlja karboksilni radikal. Reakcija se izvodi u prisustvu veznog sredstva kao što je karbodiimid (na primjer N,N'-dicikloheksilkarbodiimid) ili N,N'-karbonildiimidazol, u inertnom solventu kao što je eter (na primjer tetrahidrofuran ili dioksan), amid (N,N-dimetilformamid), klorirani solvent (na primjer metilenski klorid, l,2-dikloroetan ili kloroform) ili dimetil sulfoksid, na temperaturi između 0°C u temperature refluksa reakcijske smjese.
2) Heterociklilalkilpiperidinski derivat opće formule (II) u kojem Y predstavlja l,1-cikloalkenski radikal mogu se pripraviti djelovanjem, u bazičnom mediju, produkta strukture Hal-Alk-Ha1 u kojem Alk predstavlja alkilenski radikal koji odgovara očekivanom cikloalkilenu, na
heterociklilalkilpiperidinskom derivatu u kojem Re u Y predstavlja atom vodika. Reakcija se općenito izvodi u inertnom solventu kao što je N,N-dimetilformamid ili dimetil sulfoksid, u prisustvu kiselinskog akceptora kao što je hidrid alkalijskog metala (na primjer natrijev hidrid), na temperaturi između 20°C i 100°C.
3) Heterociklilalkilpiperidinski derivat opće formule (II) u kojem jedan između R1, R'1, R'2, R'3, R'4 ili R'5 predstavlja alkil, cikloalkil, fenil, heterociklil, benzil ili heterociklilmetilni radikal, a može se pripraviti djelovanjem derivata bora strukture R'iB(OH)2 (R'i označava jedan od supstituenata R1, R'1, R'2, R'3, R'4 ili R'5) ili 9-alkil- (ili 9-cikloalkil)-9-borbiciklo[3.3.l]nonansku strukturu na derivatu opće formule (II) u kojem supstituent R'1 predstavlja brom, jod ili atom klora, analogno s postupcima opisanim u F. Diederich i P. J. Stang, Reakcije križnog vezanja katalizirane metalom, Wiley-VCH, (1997) u prisustvu paladijeve soli (na primjer tetrakis(trifenil-fosfina) [lakuna] ili difenilfosfinoferocen-paladij klorida) i baze kao što je kalijev fosfat, u inertnom solventu kao što je amid (na primjer, N,N-dimetilformamid), etera (na primjer tetrahidrofuran) ili nitrila (na primjer acetonitril), na temperaturi između 20°C i temperature refluksa reakcijske smjese.
4) Heterociklilalkilpiperidinski derivati opće formule (II) u kojima jedan od R1, R'1, R'2, R'3, R'4 ili R'5 predstavlja radikal -NRaRb mogu se pripraviti djelovanjem amina HNRaRb na derivat opće formule (II) u kojem supstituent R'i (R'i značava jedan od supstituenata R1, R'1, R'2, R'3, R'4 ili R'5) predstavlja brom, jod ili atom klora, analogno s postupcima opisanim u J. Org. Chem., 6066 (1997) i Tetrahedron Lett., 6359 (1997) u prisustvu paladijeva katalizatora, pod sličnim uvjetima kao što su opisani za reakciju halo derivata formule (III) s derivatom opće formule (II).
Kada Ra i Rb predstavljaju atome vodika, dobiveni amino derivat se može pretvoriti u fluoro derivat djelovanjem alkalnog nitrita (na primjer natrijeva nitrita) u kiselom mediju (tetrafluoroborna kiselina ili heksafluorofosforna kiselina) u vodi na temperaturi između -10°C i 20°C, kako bi se pripravio diazonijev tetrafluoroborat ili heksafluorofosfat, te potom slijedi piroliza dobivenog produkta u skladu s Baz-Schiemanovom reakcijom, Org.Synth., Coll 5, 133 (1973).
5) Heterociklilalkilpiperidinski derivati opće formule (II) u kojima R1, R'1, R'2, R'3, R'4 ili R'5 predstavljaju alkiloksi, alkiltio, cikloalkiloksi, ciloalkiltio, benziloksi ili heterociklilmetiloksi radikal, mogu se pripraviti djelovanjem alkohola ili odgovarajućeg tiola na heterociklilalkilpiperidinski derivat u kojem jedan od radikala R'i predstavlja brom, jod ili atom klora. Reakcija se općenito izvodi u inertnom solventu kao što je eter (na primjer tetrahidrofuran ili dioksan), amid (na primjer N,N-dimetilformamid) ili dimetil sulfoksid, u prisustvu kiselinskog akceptora kao što je trialkilamin (na primjer trietilamin), hidrida alkalijskog metala (na primjer natrijeva hidrida), metillitija ili n-butillitija, na temperaturi između 0°C i temperature refluksa reakcijske smjese.
Heterociklilalkilpiperidinski derivati opće formule (II) u kojima R1, R'1, R'2, R'3, R'4 ili R'5 predstavljaju hidrokdilni radikal mogu se pripraviti iz odgovarajućih derivata u kojima jedan od radikala R'i predstavlja metoksi djelovanjem snažne kiseline kao što je bromovodična kiselina, na temperaturi između 20°C i temperature refluksa reakcijske smjese.
Heterociklilalkilpiperidinski derivati opće formule (II) u kojima R1, R'1, R'2, R'3, R'4 ili R'5 predstavljaju trifluorometoksi radikal mogu se pripraviti analogno s postupkom opisanim u Sun W.Y. Synlett., 11, 1279 (1997) kako bi se dobio derivat u kojem R'i predstavlja -O-CS-SCH3 radikal, počevši s odgovarajućim hidroksilnim derivatom; navedeni radikal je pretvoren u trifluorometilni radikal primjenom postupaka opisanih u Kuroboshi M. i sur., Tetrahedron Lett., 33(29), 4173 (1992) u prisustvu l,3-dibromo-5,5-dimetilhidantoina u HF-piridinskom kompleksu na temperaturi između 0°C i 20°C.
Heterociklilalkilpiperidinski derivati opće formule (II) u kojima R1, R'1, R'2, R'3, R'4 ili R'5 predstavljaju alkiloksi, cikloalkiloksi, fenoksi, benziloksi, heterocikliloksi ili heterociklilmetiloksi radikal, a mogu se pripraviti djelovanjem odgovarajućeg halo derivata na derivat opće formule (II) u kojoj je R'i modificiran u hidroksil. Postupak se prikladno izvodi primjenom bromo derivata, u inertnom solventu kao što je eter (na primjer tetrahidrofuran ili dioksan), amid (na primjer N,N-dimetilformamid) ili dimetil sulfoksid, u prisustvu kiselinskog akceptora kao što je trialkilamin (na primjer trietilamin), hidrida alkalijskog metala (na primjer natrijeva hidrida), metillitija ili N-butillitija, po izboru u prisustvu paladijeve soli [analogno postupcima opisanim u J. Am. Chem. Soc., 4369 (1999);
Tetrahedron Lett., 8005 (1997); Angew. Chem. Int. Ed. Engl., 2047 (1998)], na temperaturi između 0°C i temperature refluksa reakcijske smjese.
6) Heterociklilalkilpiperidinski derivati opće formule (II) u kojima R1 predstavlja trifluorometilni radikal mogu se pripraviti djelovanjem trifluorometilirajućeg agensa (osobito bromo derivata Br-CF3 ili jodo derivata I-CF3) na heterociklilalkilpiperidinski derivat u kojem je jedan od radikala R1 brom, jod ili atom klora, u prisustvu bakra u obliku bakar(I) soli kao što je Cul, u solventu kao što je dimetilformamid, između 20°C i 150°C, analogno s J.C.S. Chem. Commun., l, 53 (1992) ili Chem. Commun., 18, 1389 (1993).
7) Heterociklilalkilpiperidinski derivati opće formule (II) u kojima R1, R'1, R'2, R'3, R'4 ili R'5 predstavljaju alkiltio, cikloalkiltio, trifluorometiltio, feniltio ili heterocikliltio radikal mogu se dobiti djelovanjem odgovarajućeg halo derivata na heterociklilalkilpiperidinski derivat koji nosi merkapto supstituent. Posutap se prikladno izvodi primjenom bromo derivata, pod prethodno opisanim uvjetima za djelovanje halo derivata na alkohol, na temperaturi između 20°C i temperature refluksa reakcijske smjese. U slučaju trifluorometiltio radikala, postupak se izvodi analogno s postupkom opisanim u Tet. Lett., 33 (44), 6677 (1992).
Merkapto derivat heterociklilalkilpiperidina opće formule (II) može se dobiti iz heterociklilalkilpiperidinskog derivata u kojem jedan od radikala R'i predstavlja brom, jod ili atom klora (prikladno atom broma) analogno s postupcima opisanim u Q.L. Zhou i sur., Tetrahedron, 15, 4467 (1994); C. Bieniauz i sur., Tetrahedron Letters, 34, 6, 939 (1993) i E.D. Amstuts, J. Am. Chem. Soc., 68, 498 (1946). Reakcija se izvodi, na primjer, u prisustvu Na3PO3S ili Na2S u inertnom solventu kao što je alkohol (na primjer metanol ili etanol), po izboru u prisustvu vode, na temperaturi između 20°C i temperature refluksa reakcijske smjese.
8) Heterociklilalkilpiperidinski derivati opće formule (II)u kojima R1, R'1, R'2, R'3, R'4 ili R'5 predstavljaju cijano radikal mogu se pripraviti iz odgovarajućeg derivata u kojem jedan od derivata R'i predstavlja halogeni atom, prikladno atom broma ili joda, primjenom postupaka opisanih u Halley F. i sur., Synth. Comm., 27, 7, 1199 (1997) i Tschaen D. M. i sur., J. Org. Chem., 60, 14, 4324 (1995), u prisustvu CuCN, ili KCN i po izboru u prisustvu katalizatora.
Heterociklilalkilpiperidinski derivati opće formule (II) u kojima R1, R'1, R'2, R'3, R'4 ili R'5 predstavljaju karboksil, alkiloksikarbonil, cikloalkiloksikarbonil ili -CO-NraRb mogu se pripraviti iz cijano derivata, u skladu sa uobičajenim postupcima za pretvorbu u kiselinu, ester i amid, a koji ne utječu na ostatak molekule, te neke od postupaka primjene koji su prethodno navedeni. Osobito, u prisustvu karbodiimida (N,N'-dicikloheksilkarbodiimid) ili N,N'-karbonildiimidazola, u eteru (tetrahidrofuran ili dioksan), amidu (N,N-dimetilformamidu) ili kloriranom solventu (metilenski klorid, l,2-dikloroetan ili kloroform), na temperaturi između 0°C i temperature refluksa reakcijske smjese.
9) Heterociklilalkilpiperidinski derivati opće formule (II) u kojima R1, R'1, R'2, R'3, R'4 ili R'5 predstavljaju hidroksimetilni radikal mogu se pripraviti redukcijom heterociklilalkilpiperidinskog derivata opće formule (II) u kojem jedan od radikala R'i predstavlja karboksilni radikal, primjenom reducirajućeg sredstva kao što je, na primjer, litij aluminijev hidrid ili borohidrid, u inertnom solventu kao što je eter (na primjer tetrahidrofuran ili dioksan) ili kloriranom solventu (na primjer metilenski klorid, 1,2-dikloroetan ili kloroform), na temperaturi između 0°C i temperature refluksa reakcijske smjese.
Heterociklilalkilpiperidinski derivati opće formule (II) u kojima R1, R'1, R'2, R'3, R'4 ili R'5 predstavljaju alkiloksimetil ili cikloalkiloksimetilni radikal mogu se pripraviti djelovanjem odgovarajućeg derivata (prikladno bromo derivata) na odgovarajući heterociklilalkilpiperidinski derivat u kojem radikal R'i predstavlja hidroksimetilni radikal. Reakcija se općenito izvodi u inertnom solventu kao što je eter (na primjer tetrahidrofuran ili dioksan), amidu (na primjer N,N-dimetilformamid) ili dimetil sulfoksidu, u prisustvu kiselinskog akceptora kao što trialkilamin (na primjer trietilamin) ili hidrid alkalijskog metala (na primjer natrijev hidrid), na temperaturi između 20°C i 100°C.
Heterociklilalilpiperidinski derivati opće formule (II) u kojima R1, R'1, R'2, R'3, R'4 ili R'5 predstavljaju fluorometilni radikal mogu se pripraviti djelovanjem fluorirajućeg agensa na heterociklilakilpiperidinski derivat u kojem odgovarajući radikal R'i predstavlja hidroksimetilni radikal. Reakcija se može izvesti pod prethodno opisanim fluorirajućim uvjetima za umetanje radikala Re koji označava fluor.
Heterociklilalkilpiperidinski derivati opće formule (II) u kojima R1, R'1, R'2, R'3, R'4 ili R'5 označavaju alkiltiometilni ili cikloalkiltiometilni radikal mogu se pripraviti djelovanjem odgovarajućeg tiola na
heterociklilalkilpiperidinski derivat u kojem modificirani radikal R'i predstavlja halometil (halogen koji povoljno označava brom ili atom klora). Reakcija se općenito izvodi u inertnom sloventu kao što je eter (na primjer tetrahidrofuran ili dioksan), amid (na primjer N,N-dimetilformamid) ili dimetil sulfoksid, u prisustvu kiselinskog akceptora kao što je trialkilamin (na primjer trietilamin) ili hidrida alkalijskog metala (na primjer natrijev hidrid), na temperaturi između 20°C i temperature refluksa reakcijske smjese.
Heterociklilalkilpiperidinski derivati koji nose halometilni radikal R'i se pripravljaju iz odgovarajućih derivata u kojima R'i predstavlja hidroksimetilni radikal djelovanjem halogenirajućeg agensa (halofosfornog derivata ili diotnilnog klorida). Reakcija se po izboru izvodi u inertnom solventu kao što je diklorometan, na temperaturi između 0°C i 60°C, po izboru u prisustvu baze kao što je piridin.
Heterociklilalkilpiperidinski derivati opće formule (II) u kojima R1, R'1, R'2, R'3, R'4 ili R'5 predstavljaju radikal -CH2-NRaRb mogu se dobiti djelovanjem amina HNRaRb na heterociklilalkilpiperidinski derivat u kojem modificirani radikal R'i predstavlja halometil (halogen koji povoljno predstavlja atom broma ili klora). Reakcija se izvodi u inertnom solventu kao što je eter (na primjer tetrahidrofuran ili dioksan), amid (na primjer N,N-dimetilformamid) ili dimetil sulfoksid, u prisustvu kiselinskog akceptora kao što je trialkilamin (na primjer trietilamin) ili hidrida alkalijskog metala (na primjer natrijeva hidrida), na temperaturi između 20°C i temperature refluksa reakcijske smjese. Halometilni derivat je pripravljen u skladu s prethodno navedenim postupkom.
Heterociklilalkilpiperidinski derivati opće formule (II) u kojima R1, R'1, R'2, R'3, R'4 ili R'5 predstavljaju karboksimetilni radikal mogu se pripraviti djelovanjem alkalijskog cijanida na heterociklilalkilpiperidinski derivat u kojem modificirani radikal R'i predstavlja halometil (halogen koji u povoljnom slučaju predstavlja atom broma ili klora), te potom hidrolizom nitrila. Reakcija se izvodi primjenom natrijeva cijanida ili kalijeva cijanida u organskom solventu kao što je dimetil sulfoksid ili dimetilformamid, ili u smjesi vode i alkohola, na temperaturi između 0°C i temperature vrenja reakcijske smjese, a zatim djelovanjem jake kiseline kao što je klorovodična kiselina, po izboru u prisustvu nižeg alifatskog alkohola, na temperaturi između 0°C i točke vrenja reakcijske smjese.
Heterociklilalkilpiperidinski derivati opće formule (II) u kojima R1, R'1, R'2, R'3, R'4 ili R'5 predstavljaju alkiloksikarbonilmetil, cikloalkiloksi-karbonilmetil ili -CH2-CO-NRaRb radikal mogu se pripraviti iz odgovarajuće kiseline u skladu s uobičajenim postupcima za pretvorbu kisline u ester ili amid, a koji ne utječu na ostatak molekule, osobito u prisustvu veznog sredstva kao što je karbodiimid u skladu s prethodno navedenim postupkom.
Heterociklički derivati opće formule (III) u kojima Ha1 predstavlja atom broma, R1 je u skladu s prethodno navedenom definicijom, X1 do X4 predstavljaju, osobito, >C-R'1 do >C-R'4, a X5 predstavlja >CH, mogu se pripraviti bromiranjem odgovarajućeg 4-hidroksikinolina primjenom bromirajućeg agensa kao što je fosforni oksitribromid ili tionilni bromid bez solventa, na temperaturi između 20°C i 115°C.
4-hidroksikinolini se mogu pripraviti dekarboksilacijom odgovarajućeg 3-karboksi-4-hidroksi-kinolina, u solventu kaošto je difenilni eter, na temperaturi između 100°C i 260°C.
3-Karboksi-4-hidroksikinolini mogu se pripraviti analogno s postupkom opisanim u europskoj patentnoj prijavi EP-A-0 379 412, počevši od željenog anilinskog derivata.
Heterociklički derivati opće formule (III) u kojima Ha1 predstavlja atom broma, R1 je definiran kao što je prethodno navedeno, X1 do X4 predstavljaju, osobito, >C-R'1 do >C-R'4, a X5 predstavlja >C-C1, mogu se pripraviti bromiranjem odgovarajućeg 3-kloro-4-hidroksikinolina. Bromiranje se općenito izvodi trifenil-fosfin dibromidom u acetonitrilu na temperaturi između 20°C i 85°C.
3-Kloro-4-hidroksikinolini se mogu pripraviti kloriranjem 4-hidroksikinolina. Kloriranje se izvodi, na primjer, primjenom N-klorosukcinimida u solventu kao što je octena kiselina, na temperaturi između 20°C i 100°C.
Heterociklički derivati opće formule (III) u kojima Ha1 predstavlja atom broma, R1 je prethodno definiran, X1 do X4 predstavljaju, osobito, >C-R'1 do >C-R'4, a X5 predstavlja >C-COCF3, a mogu se pripraviti analogno s pripravljanjem derivata u kojima X5 predstavlja >CH, bromiranjem odgovarajućeg 4-hidroksi-3-fluoracdetilkinolinskog derivata. Reakcija se izvodi bez solventa, primjenom bromirajućeg agensa kao što je fosforni oksitribromid, na temperaturi između 20°C i 115°C. 4-Hidroksi-3-trifluoro-acetilkinolin se može pripraviti analogno s postupkom opisanim za pripravljanje 3-karboksi-4-hidroksikinolina.
Heterociklički derivati opće formule (III) u kojima Ha1 predstavlja atom joda, R1 je metoksi radikal, X1 do X4 predstavlja >C-R'1 do >C-R'4, a X5 predstavlja >C-F, mogu se pripraviti analogno studijama E. Arzel i sur., Tetrahedron, 55, 12149-12156 (1999) počevši od 3-fluoro-6-metoksi-kinolina, u slijedu djelovanjem baze, a zatim joda. Na primjer, litij diizopropilamida u solventu kao što je eter (tetrahidrofuran) na primjenjenoj temperaturi između -80°C i 20°C. 3-Fluoro-6-metoksikinolin mogu se pripraviti pirolizom 6-metoksikinolin diazonij 3-tetra-fluoroborata ili 3-heksafluorofosfata u skladu s Balz-Schiemanovom reakcijom, Org. Synth., Coll 5, 133 (1973), na temperaturi između 100°C i 240°C. 6-Metoksi-kinolin diazonij 3-tetrafluoroborat ili 6-metoksi-kinolin diazonij 3-heksafluorofosfat se mogu pripraviti iz 3-amino-6-metoksikinolina djelovanjem alkalnog nitrita (na primjer natrijeva nitrita) u kiselinom mediju (tetrafluoroborna kiselina ili heksafluorofosforna kiselina) u solventu kao što je voda na temperaturi između -10°C i +20°C, analogno studijama A. Roe i sur., J. Am. Chem. Soc., 71, 1785-86 (1949) ili djelovanjem alkilnog nitrita (kao što je, na primjer, izoamilni nitrit) i trifluoroborat/dietilni eter kompleksa u solventu kao što je eter (na primjer tetrahidrofuran) na temperaturi između -10°C i +10°C.
3-Amino-6-metoksikinolin je pripravljen kao što je opisano u N. Heindel, J. Med. Chem. (1970) 13, 760.
Heterociklički derivati opće formule (III) u kojima Ha1 predstavlja atom broma, ri je definiran kao što je prethodno navedeno, X2 do X4 predstavljaju >C-R'2 do >C-R'4, a X1 predstavlja atom dušika ili na drugi način X1, X3 i X4 predstavljaju >C-R'1, >C-R'3 i >C-R'4, a X2 predstavlja atom dušika, dok X5 predstavlja >CH ili >C-Cl, a mogu se pripraviti analogno prethodno opisanim postupcima kada X1 do X4 predstavljaju >C-R'1 do >C-R'4 ili u skladu sa sintezom opisanom u Adams J.T. i sur., J. Am. Chem. Soc., 68, 1317 (1946) za l,5-naftilhiridine i S. Radi i sur., Collect. Chech. Chem. Commun., 56, 2420 (1991) za l,7-naftilhiridine, počevši od 3-aminopiridina. Hidroksinafthiridin neophodan za izvođenje reakcije isto tako se pripravlja analogno prethodno opisanim postupcima za hidroksikinoline, no počevši s 3-aminopiridinom ili njegovim supstituiranim derivatima. 3-Aminopiridinski derivati se mogu dobiti prilagodbom postupaka opisanih u «The Chemistry of Heterocyclic Compounds», Vol. 14, Piridini i njihovi derivati, dodatni dio III, strana 41, Ed. R.A. Abramovitch, InterScience Publication.
Heterociklički derivati opće formule (III) u kojima Ha1 predstavlja atom broma, ri je u skladu s prethodno navedenom definicijom, X1, X2 i X4 predstavljaju >C-R'1, >C-R'2 i >C-R'4, a X3 predstavlja atom dušika, dok X5 predstavlja >CH ili >C-Cl, a mogu se pripraviti analogno prethodno opisanim postupcima kada X1 do X4 predstavljaju >C-R'1 do >C-R'4 ili u skladu sa sintezom opisanom u D. Heber i sur., Arzneim-Forsch, 44, 809 (1994) počevši od 2-aminopiridina ili njegovih supstituiranih derivata.
2-Aminopiridini se mogu pripraviti primjenom ili prilagodbom postupaka opisanih u «Kemiji heterocikličkih spojeva», Vol. 14, Piridini i njihovi derivati, dodatni dio III, strana 41. Ed. R.A. Abramovitch, InterScience Publication.
Derivati opće formule (III) u kojima Ha1 predstavlja atom broma, R1 je u skladu s prethodno navedenom definicijom, a X$ predstavlja atom dušika mogu se pripraviti iz 2-amino-benzenamida kao što je opisano u J. Am. Chem. Soc., 69, 184 (1947). 2-Amino-benzamid je cikliziran u prisustvu alkil ortoformata kao što je etilni ortoformat u solventu kao što je dietilen glikol na temperaturi između 105°C i 120°C do nastanka 4-hidroksikinazolina, koji je bromiran kao što je prethodno opisano. 2-Amino-benzamid je dobiven iz odgovarajućeg anilina primjenom ili prilagodbom postupaka opisanih u V. Snieckus, Chem. Rev., 90, 879 (1990) i Pure Appl. Chem., 62, 2047 (1990).
Heterociklički derivati opće formule (III) u kojima Ha1 predstavlja atom broma, ri je u skladu s prethodno navedenom definicijom, a X4 predstavlja atom dušika mogu se pripraviti iz 2-acetilanilina kao što je opisano u Synth. Commun., 19, 3087 (1989). Dobiveni 4-hidroksikinolin je bromiran pod prethodno opisanim uvjetima. 2-Acetil-anilini su dobiveni iz odgovarajućeg anilina primjenom postupaka prethodno navedenih za 2-aminobenzamid.
Piperidinski derivati opće formule (IV) u kojima n=0 i R''2 predstavlja karboksil mogu se pripraviti iz odgovarajućih piperidinskih derivata opće formule:
[image]
u kojoj je R''2 prethodno zaštićen, a u skladu je s gore navedenom definicijom, a Rz je prethodno definiran, analogno studijama Koppel, J. Chem. Soc. Chem. Commun., 473(1975), reakcijom između piperidinskog derivata i vinil fenilnog sulfoksida u prisustvu baze (na primjer natrijeva hidrida, litijeva diizopropilamida ili litijeva heksametildizililamida) u solventu kao što je eter (na primjer tetrahidrofuran) na temperaturi između 0°C i 100°C. Dobiveni intermedijarni adukt je zatim termoliziran između 60°C i 150°C u inertnom solventu (na primjer kloroform, tetrahidrofuran, toluen ili ksilen). Rz predstavlja zaštitnu skupinu za dušikov atom kao što je, na primjer, t-butiloksikarbonil.
Piperidinski derivati opće formule (IV) u kojima n=1 ili 2, a R''2 predstavlja karboksil mogu se pripraviti iz odgovarajućeg piperidinskog derivata opće formule (V) u kojoj je R''2 prethodno zaštićen, u skladu s ili analogno s postupcima navedenim u Primjerima. Osobito, postupak se izvodi djelovanjem u slijedu baze kao što je, na primjer, litijev diizopropilamid ili n-butillitij, u solventu kao što je eter (na primjer tetrahidrofuran) na temperaturi između -80°C i 0°C, a zatim alkenil halida (alil halida ili l-halo-3-butena).
Piperidinski derivati opće formule (IV) u kojma je n u skladu s prethodno navedenom definicijom, a R''2 predstavlja alkiloksikarbonil, cikloalkiloksikarbonil, -CO-NRaRb, alkiloksikarbonilmetil, alkiloksikarboniletil, cikloalkiloksikarbonilmetil, cikloalkiloksikarboniletil, -CH2-CONRaRb, ili - (CH2)2-CONRaRb ili u kojima Rc u R2 predstavlja alkiloksikarbonil, cikloalkiloksikarbonil ili -CO-NRaRb mogu se pripraviti iz odgovarajućih derivata karboksilne kiseline, u skladu s uobičajenim postupcima za pretvorbu u ester ili amid, a koji ne utječu na ostatak molekule. Esteri su pripravljeni u prisustvu veznog sredstva kao što je karbodiimid (na primjer (N,N1-diciklo[lacuna]-karbodiimid) ili N,N'-karbonildiimidazol u eteru (na primjer tetrahidrofuran ili dioksan), amidu (na primjer diklorometan, 1,2-dikloroetan ili kloroform), na temperaturi između 0°C i temperature refluksa reakcijske smjese. Amidi su pripravljeni djelovanjem odgovarajućih amina u identičnim uvjetima kao što je prethodno navedeno. Osobito, kada se odnose na pripravljanje derivata u kojima Rc u R''2 predstavlja ester, analogno postupcima opisnim u Saha i sur., J. Chem. Soc. Perkin I, 505 (1985), djelovanjem diazoalkana (na primjer diazometana) u eteru (na primjer dietilnom eteru) na temperaturi između -10°C i 5°C.
Piperidinski derivati opće formule (IV) u kojma je n u skladu s prethodno navedenom definicijom, a R''2 predstavlja cijano, -CH2-CN ili -(CH2)2-CN mogu se pripraviti iz odgovarajućih amida djelovanjem dehidratirajućeg agensa, prilagodbom postupka opisanog u Bieron i sur., Zabicky «Kemija amida» Wiley, str. 274-283 (1970). Reakcija se izvodi u prisustvu fosforna pentoksida ili fosforna oksiklorida s ili bez solventa, na temperaturi između 20°C i temperature refluksa reakcijske smjese.
Piperidinski derivati opće formule (IV) u kojma je n u skladu s prethodno navedenom definicijom, a R''2 predstavlja hidroksimetil, cijanometil ili karboksimetil mogu se pripraviti iz piperidinskog derivata opće formule:
[image]
u kojoj Rz i n su u skladu s prethodno navedenom definicijom, a Ry predstavlja zaštitni radikal podložan hidrolizi, osobito djelovanjem hidrida (na primjer litij aluminijeva hidrida ili diizobutilaluminijeva hidrida) u solventu kao što je eter (na primjer tetrahidrofuran) na temperaturi između 20°C i 60°C do nastanka piperidinskog derivata u kojem R''2 predstavlja hidroksimetil, a zatim slijedi pretvorba hidroksimetilnog radikala u cijanometilni radikal, a potom u karboksimetilni radikal u skladu s uobičajenim postupcima koji ne utječu na ostatak molekule.
Kada Ry predstavlja radikal podložan hidrolizi, može osobito biti odabran između alkila (1 do 4 atoma ugljika u ravnog ili razgranatog lanca), benzila, cikloalkila, fenilpropila i alila.
Pretvorba u kiselinu se može izvesti osobito iz zadnjeg spoja, djelovanjem halogenirajućeg agensa kao što je, na primjer, tionilklorid ili fosforni triklorid ili tribromid ili djelovanjem alkansulfonilnog klorida (na primjer metansulfonilnog klorida ili p-toluensulfonilnog klorida) u inertnom sloventu (na primjer diklorometanu), te potom djelovanjem alkalnog cijanida (na primjer kalijeva cijanida ili natrijeva cijanida) i hidrolizom. Reakcija halogenacije se izvodi u kloriranom solventu (na primjer diklorometanu ili kloroformu), na temperaturi između 0°C i temperature refluksa reakcijske smjese. Reakcija alkalnog cijanida se može izvesti u dimetilnom sulfoksidu, amidu (na primjer dimetilformamidu), ketonu (na primjer acetonu), eteru (na primjer tetrahidrofuranu) ili alkoholu (na primjer metanolu ili etanolu), na temperaturi između 20°C i temperature refluksa reakcijske smjese. Nitril je hidroliziran u skladu s uobičajenim postupcima koji ne utječu na ostatak molekule, osobito djelovanjem klorovodične kiseline u metanolskom mediju, na temperaturi između 20°C i 70°C, te potom saponifikacijom dobivenog estera (na primjer s natrijevim hidroksidom u smjesi dioksana i vode), ili izravno djelovanjem vodene otopine sulfatne kiseline na temperaturi između 50°C i 80°C.
Piperidinski derivati opće formule (IV) u kojma su n i Rz u skladu s prethodno navedenom definicijom, a R''2 predstavlja 2-karboksietilni radikal mogu se pripraviti iz derivata opće formule (IV) u kojima R''2 predstavlja hidroksimetilni radikal putem halo derivata (pripravljenog kao što je gore navedeno), a zatim vezanjem s natrijevom soli ili dietilnim malonatom, te potom kiselom hidrolizom vodenog medija dobivenog produkta.
Piperidinski derivati opće formule (IV) u kojima su n i Rz u skladu s prethodno navedenom definicijom, a R''2 predstavlja karboksihidroksimetil ili karboksikarbonil mogu se pripraviti homologacijom piperdinskog derivata opće formule:
[image]
u kojoj Rz i n su u skladu s prethodno navedenom definicijom, primjenom ili prilagodbom postupaka opisanih u M. Mizuno i sur., Tetrahedron Lett., 39, 9209 (1998). Reakcija se izvodi djelovanjem dialkilnog fosforocijanidata (na primjer dietilnog fosforocijanidata) u prisustvu organske baze (na primjer trietilamina) u eteru (na primjer tetrahidrofuran) na temperaturi između -50°C i 10°C. Dobiveni međuprodukt dicijanofosfat je zatim hidroliziran u kiselom mediju (na primjer koncentrirana klorovodična kiselina) u polarnom solventu (na primjer vodi) na temperaturi refluksa reakcijske smjese. Derivati u kojima R''2 predstavlja karboksikarbonil, dobiveni su oksidacijom odgovarajućih estera, primjenom psotupaka opisanih u Burhardt i sur., Tetrahedron Lett., 29, 3433 (1988), te potom hidrolizom dobivenog produkta. Osobito djelovanjem oksidirajućeg agensa kao što je triacetoksi-1,1-dihidro-1,2-benziodoksol-3(IH)jedan u solventu kao što je nitril ili klorirani derivat (na primjer acetonitril ili diklorometan) na temperaturi između 0°C i 40°C, te potom hidrolizom djelovanjem baze (na primjer natrijeva hidroksida) u vodeno-alkoholnom solventu (na primjer voda-metanol) na temperaturi između 20°C i temperature refluksa reakcijske smjese.
Piperidinski derivati opće formule (IV) u kojima su n i Rz u skladu s prethodno navedenom definicijom, a R''2 predstavlja -CF2-Rc mogu se pripraviti djelovanjem fluorirajućeg agensa na piperidinski derivat opće formule (IV) u kojoj R''2 predstavlja radikal -CO-Rc, a Rc je ester, analogno postupcima opisanim u M. Parisi i sur., J. Org. Chem, 60, 5174 (1995), po izboru zatim slijedi hidroliza piperidinskog derivata u kojem Rc predstavlja karboksil. Uvjeti fluoriranja su nalik onim prethodno opisanim za pripravljanje derivata u kojima Re u Y predstavlja atom fluora. Hidroliza se izvodi djelovanjem baze u vodeno-alkoholnom mediju prema prethodno opisanim uvjetima.
Piperidinski derivati opće formule (IV) u kojima su n i Rz u skladu s prethodno navedenom definicijom, a R''2 predstavlja radikal -CH=CH-Rc mogu se pripraviti oksidacijom aldehida derivata opće formule (IV) u kojoj R''2 predstavlja hidroksimetilni radikal prilagodbom postupaka opisanih u Org. Synth. Coll., Vol. II, str. 541, Coll. Vol. 5, str. 242, te zatim pretvorbom derivata u kojima R1'2 predstavlja -CH=CH-Rc, a u kojem je Rc ester, primjenom Wittigovog postupka, te po izboru zatim hidrolizom dobivenog estera u kiselinu. Oksidacija se izvodi djelovanjem oksidirajućeg agensa (na primjer kalijeva dikromata) u kiselom mediju (na primjer sumporna kiselina) u polarnom solventu (na primjer voda) ili kromovom oksidu u prisustvu baze (na primjer piridina) u kloriranom solventu (na primjer diklorometanu) na temperaturi između 0°C i 20°C. Pretvorba u nezasićeni derivat se izvodi primjenom postupaka opisanih u Johnson «Ylid Chemistry» Academic Press (1966) djelovanjem fosfornog ylida (na primjer karboksimetilentrifenilfosforana) u ugljikovodiku (na primjer toluenu) na temperaturi između 60°C i temperature refluksa reakcijske smjese. Hidroliza se izvodi u skladu s prethodno opisanim postupcima.
Piperidinski derivati opće formule (IV) u kojima su n i Rz u skladu s prethodno navedenom definicijom, a R''2 predstavlja radikal C(CH3)CH2Rc ili -C(cikloalk)Rc mogu se pripraviti iz derivata opće formule (IV) u kojoj R''2 predstavlja -CH2-COOH primjenom postupaka opisanih u Ashutosh i sur., Tetrahedron Lett., 40, 4733 (1999) i Sauers, J. Org. Chem., 57, 671 (1992) po izboru zatim slijedi hidroliza dobivenog estera. Reakcija se izvodi osobito u slijedu djelovanjem amida (na primjer litij diizopropilamida), te zatim metilnog halida (na primjer metilnog jodida) ili derivata formule Hal-Alk-Ha1 (Ha1 povoljno predstavlja atom broma) u polarnom solventu (na primjer heksametilfosforotiramida) na temperaturi između 0°C i 60°C.
Potrebno je uočiti da prethodno navedeni postupak za pripravljanje piperidinskih derivata opće formule (IV) se isto tako može primijeniti na derivate opće formule (II) ako je potrebno prvo vezati piperidin sa heterocikličkim derivatom opće formule (III), a zatim pretvoriti radikal R2 u prethodno opisanim uvjetima.
Isto tako je jasno da postupci opisani u Primjerima isto tako predstavljaju dio prikazanog izuma.
Očito je da derivati opće formule (I) i (II) mogu postojati u enantiomerskom boliku ili u Syn ili anti obliku. Enantiomerički i dijastereoizomerički, te syn ili anti oblici i njihove smjese isto tako se ubrajaju u kontekst prikazanog izuma. Navedeni oblici se mogu razdvojiti u skladu s uobičajenim postupcima, osobito kromatografijom na silikgelu ili tekućom kromatograijom visoke učinkovitosti (HPLC).
Heterociklilalkilpiperidinski derivati opće formule (I) se mogu pročistiti, a kada je prikladno, odgovarajućim fizičkim postupcima kao što su kristalizacija ili kromatografija.
Heterociklilalkilpiperidinski derivati opće formule (I) se mogu kada je prikladno, pretvoriti u adicijske soli s kiselinama, a poznatim postupcima. Jasno je da navedene soi isto tako pripadaju kontekstu prikazanog izuma.
Kao primjere adicijskih soli farmaceutski prihvatljivih kiselina, mogu se spomenuti soli mineralnih kiselina (hidrokloridi, hidrobromidi, sulfati, nitrati i fosfati) ili organskih kiselina (sukcinati, fumarati, tartarati, acetati, propionati, maleati, citrati, metansulfonati, etansulfonati, fenilsulfonati, p-toluensulfonati, izetionati, naftilsulfonati ili kamforsulfonati, ili supstitucijski derivati navedenih spojeva).
Neki od heterociklilalkilpiperidinskih derivata opće formule (I) koji nose karboksilni radikal mogu se pretvoriti u soli metala ili u adicijske soli s dušikovim bazama u skladu s već poznatim postupcima. Navedene soli isto tako pripadaju u opseg prikazanog izuma. Soli se mogu dobiti djelovanjem metalne baze (na primjer alkalijskog metala ili zemno-alkalijskog metala), amonijaka ili amina, na produkt u skladu s izumom, u prikladnom solventu kao što je alkohol, eter ili voda, ili izmjeničnom reakcijom sa soli organske kiseline. Po izboru koncentracijom otopine soli tvore precipitate koji se mogu odvojiti filtracijom, taloženjem ili smrzavanjem-sušenjem. Primjeri farmaceutski prihvatljivih soli predstavljaju soli alkalijskih metala (natrija, kalija ili litija) ili zemno-alkalijskih metala (magnezija ili kalcija), amonijeve soli ili soli dušikovih baza (etanolamin, dietanolamin, trimetilamin, trietilamin, metilamin, propilamin, diizopropilamin, N-N-dimetiletanolamin, benzilamin, dicikloheksilamin, N-benzil-β-fenetilamin, N,N'-dibenziletilendiamin, difenilendiamin, benzhidrilamin, kinin, kolin, arginin, lizin, leucin ili dibenzilamin).
Heterociklilalkilpiperidinski derivati u skladu s izumom su osobito korisna antibakterijska sredstva.
In vitro je uočeno da heterociklilalkilpiperidinski derivati u skladu s izumom djeluju na gram pozitivne mikroorganizme u koncentracijama između 0.03 μg/ml i 4 μg/ml na meticilin rezistentni Staphγlococcus aureus AS5155, a isto tako, za većinu njih, u koncentracijama između 0.03 μg/ml i 8 μg/ml na Streptococcus pneumoniae 6254-01; isto tako je uočeno da djeluju na gram-negativne mikroorganizme kao što su, na primjer, i na neograničavajući način, Moraxella catarrhalis IPA 152, u koncentracijama između 0.12 μg/ml i 64 μg/ml. In vivo, je zabilježeno da djeluju na eksperimentalne infekcije miševa sa Staphylococcus aureus IP8203, bilo supkutano primijenjeni u dozama između 18 mg/kg i 150 mg/kg (DC50), ili oralno u dozama između 20 mg/kg i 150 mg/kg.
Na kraju, produkti u skladu s izumom imaju osobitu prednost zbog niske toksičnosti. Niti jedan od produkata nije pokazao toksičnost supkutano primijenjen miševima u dozi od 100 mg/kg (2 primjene).
U općoj formuli (I), produkti u kojima
X1, X2, X3, X4 i X5 predstavljaju >C-R'1, do >C-R'5, ili alternativno, najviše jedan od njih predstavlja atom dušika,
R1, R'1, R'2, R'3, R'4 i R'5 su identični ili različiti i predstavljaju atom vodika ili halogeni atom ili alkilni ili alkoksi radikal, ili predstavljaju metilenski radikal supstituiran s alkoksi.
R2 predstavlja karboksil, alkiloksikarbonil ili CONRaRb (u kojem Ra predstavlja atom vodika, a Rb predstavlja atom vodika ili hidroksilni radikal) ili
R2 predstavlja hidroksimetil, alkil koji sadrži 1 ili 2 atoma ugljika supstituirana s karboksilom ili alkiloksi-karbonilom,
R3 predstavlja radikal alk-R°3, u kojem alk predstavlja alkilni radikal, a R°3 predstavlja vodik, cikloalkil, cikloalkiltio, fenil, fenoksi, feniltio, fenilamino, heterocikliloksi ili heterocikliltio ili alternativno R°3 predstavlja -CR'b=CR'c-R'a u kojem R'a predstavlja fenil, te u kojem R'b i R'c predstavljaju vodik,
Y predstavlja radikal >CH-Re u kojem Re je vodik, fluoro ili hidroksil,
n je cijeli broj od 2 do 3,
a uočeno je da osobitu prednost imaju fenilni ili heterociklilni radikali ili prethodno navedeni dijelovi po izboru supstituirani na prstenu s 1 do 4 halogena atoma.
Osobito su prikladni dolje navedeni heterociklilalkil piperidinski derivati opće formule (I):
• 4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna kiselina
• 4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-karboksilna kiselina
• 4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-(2-tiazol-2-tioetil)piperidin-4-karboksilna kiselina
• 1-(2-Ciklopentiltioetil)-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilna kiselina
• 4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-(3-fenilalil)piperidin-4-karboksilna kiselina, te njihove soli.
Među produktima u skladu s izumom koji će biti detaljnije prikazani su heterociklilalkilpiperidinski derivati opće formule (I), nazivi koji slijede:
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-heptil-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-fenil-butil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(2-fluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(3-fluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(4-fluorofenil)butil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,3-difluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,6-difluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-difluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-fenil-tiopropil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-fluorofeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluorofeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-fluorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3-difluorofeniltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofeniltio)propil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,6-difluorofeniltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilaraino)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofeniltio)propil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-klorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-klorofeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-klorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-klorofeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-klorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3- (4-klorofeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metilfeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metilfeniltio)propil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metilfeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metilfeniltio)propil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metilfeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metilfeniltio)propil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-trifluorometilfeniltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-trifluorometilfeniltio)propil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-trifluorometilfeniltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-trifluorometilfeniltio)propil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-trifluorometilfeniltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-trifluorometilfeniltio)propil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metoksifeniltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metoksifeniltio)propil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metoksifeniltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metoksifeniltio)propil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metoksifeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metoksifeniltio)propil]-piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[ciklopentilmetil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentil)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(ciklopentiltio)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(cikloheksiltio)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-2-il)butil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)tiopropil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-3-il)butil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-3-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)tiopropil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(1,3-tiazol-2-il)butil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-2-il)butil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)tiopropil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-3-il)butil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-raetoksikinolin-4-il)propil]-1-[2-(pirid-3-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)tiopropil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-raetoksikinolin-4-il)propil]-1-[4-(pirid-4-il)butil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-4-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)tiopropil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirazin-2-il)butil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirazin-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)tiopropil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4-difluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4-difluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-3-fluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-4-fluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-kloro-4-fluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-5-fluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-2-fluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluoro-4-metilfenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-bis(trifluorometil)fenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-4-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-5-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]-piperidin-4-karboksilna
kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il) propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-propil]piperidin-4-karboksilna kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-propil]piperidin-4-karboksilna kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)-etil]piperidin-4-karboksilna
kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)-etil]piperidin-4-karboksilna kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)-etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)-etil]piperidin-4-karboksilna
kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)-etil]piperidin-4-karboksilna kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)-etil]piperidin-4-karboksilna kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)-etil]piperidin-4-karboksilna kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)-etil]piperidin-4-karboksilna kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]-piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)-etil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)-etil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)-etil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)-etil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-propil]piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-propil]piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)-etil]piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)-etil]piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)-etil]piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-karboksilna kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-heptilpiperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-fenilbutil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2-fluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(3-fluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(4-fluorofenil)butil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofenil)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,3-difluorofenil)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofenil)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,6-difluorofenil)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-difluorofenil)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-feniltio-propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-fluorofeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluorofeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-fluorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3-difluorofeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofeniltio)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,6-difluorofeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1- [2-(3,4,5-trifluorofeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-karboksilna
kiselina
54
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofeniltio)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-klorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-klorofeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-klorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-klorofeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-klorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-klorofeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metilfeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metilfeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metilfeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metilfeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metilfeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metilfeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-trifluorometilfeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-trifluorometilfeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-trifluorometilfeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-trifluorometilfeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-trifluorometilfeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-trifluorometilfeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metoksifeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metoksifeniltio)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metoksifeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metoksifeniltio)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metoksifeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metoksifeniltio)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[ciklopentilmetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentil)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(ciklopentiltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(cikloheksiltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-2-il)butil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)tiopropil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-3-il)butil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-3-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)tiopropil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(1,3-tiazol-2-il)butil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-2-il)butil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)tiopropil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-3-il)butil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-3-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)tiopropil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-4-il)butil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-4-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)tiopropil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-raetoksikinolin-4-il)propil]-1-[4-(pirazin-2-il)butil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirazin-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)tiopropil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4-difluorofenil)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4-difluorofenil)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-3-fluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-4-fluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-kloro-4-fluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-5-fluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-2-fluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluoro-4-metilfenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-bis(trifluorometil)fenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-4-il)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-1iazol-5-il)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(cikloneksil)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-raetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-raetil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-raetoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-arainometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinoraetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-prop-2-inil]piperidin-
4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-prop-2-inil]piperidin-
4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-prop-2-inil]piperidin-
4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-prop-2-inil]piperidin-
4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-prop-2-inil]piperidin-
4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-prop-2-inil]piperidin-
4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-prop-2-inil]piperidin-
4-karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-fenilbutil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2-fluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(3-fluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(4-fluorofenil)butil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,3-difluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,6-difluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-difluorofenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-fenilti-propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-fluorofeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluorofeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-fluorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3-difluorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofeniltio)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,6-difluorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofeniltio)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-klorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-klorofeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-klorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-klorofeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-klorofeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-klorofeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metilfeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metilfeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metilfeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metilfeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metilfeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metilfeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-trifluorometilfeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-trifluorometilfeniltio)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-trifluorometilfeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-trifluorometilfeniltio)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-trifluorometilfeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-trifluorometilfeniltio)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metoksifeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metoksifeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metoksifeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metoksifeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metoksifeniltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metoksifeniltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[ciklopentilmetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentil)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(ciklopentiltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(cikloheksiltio)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-2-il)butil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)tiopropil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-3-il)butil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-3-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)tiopropil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(1,3-tiazol-2-il)butil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-2-il)butil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)tiopropil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-3-il)butil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-3-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)tiopropil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-4-il)butil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-4-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)tiopropil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirazin-2-il)butil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirazin-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)tiopropil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4-difluorofenil)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4-difluorofenil)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-3-fluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-4-fluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-kloro-4-fluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-5-fluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-2-fluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluoro-4-metilfenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-bis(trifluorometil)fenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-4,-il) prop-2-inil] piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-5-il)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-difluorofeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-karboksilna kiselina
83
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna
kiselina
88
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilaraino)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(21 4,6-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2f4,6-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-karboksilna
kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil] [sic] kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluororaetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-raetoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-arainometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
karboksilna kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-heptilpiperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-fenil-butil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(2-fluorofenil)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(3-fluorofenil)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(4-fluorofenil)butil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofenil)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,3-difluorofenil)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofenil)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,6-difluorofenil)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-difluorofenil)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-fenil-tiopropil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-fluorofeniltio)-propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluorofeniltio)-propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-fluorofeniltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofeniltio)-propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3-difluorofeniltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofeniltio)-propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,6-difluorofeniltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)-etil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)-etil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]-piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]-piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]-piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]-piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]-piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofeniltio)propil]-piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-klorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-klorofeniltio)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-klorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-klorofeniltio)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-klorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-klorofeniltio)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metilfeniltio)etil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metilfeniltio)propil]-piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metilfeniltio)etil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metilfeniltio)propil]-piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metilfeniltio)etil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metilfeniltio)propil]-piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-trifluorometilfeniltio)etil]-piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-trifluorometilfeniltio)propil]-piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-trifluorometilfeniltio)etil]-piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-trifluorometilfeniltio)propil]-piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-trifluorometilfeniltio)etil]-piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-trifluorometilfeniltio)propil]-piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metoksifeniltio)etil]-piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metoksifeniltio)propil]-piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metoksifeniltio)etil]-piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metoksifeniltio)propil]-piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metoksifeniltio)etil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metoksifeniltio)propil]-piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[ciklopentilmetil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentil)etil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(ciklopentiltio)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(cikloheksiltio)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-2-il)butil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)tiopropil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-3-il)butil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-3-il)tioetil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)tiopropil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(1,3-tiazol-2-il)butil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-2-il)butil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)tiopropil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-3-il)butil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-3-il)tioetil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)tiopropil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-4-il)butil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-4-il)tioetil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)tiopropil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)propil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirazin-2-il)butil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirazin-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)tiopropil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4-difluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4-difluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-3-fluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-4-fluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-kloro-4-fluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-5-fluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-2-fluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluoro-4-metilfenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-bis(trifluorometil)fenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-4-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-5-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]-piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]-piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]-piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]-piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]-piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]-piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-raetoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]-piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]-piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]-piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]-piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]-piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]-piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-raetoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tio-etil]piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tio-etil]piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]-piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenil-amino)etil]-piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenil-amino)etil]piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]-piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]-piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)-etil]-piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]-piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]-piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)-propil]piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]-piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]-piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]-piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]-piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]-piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)-propil]piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)-etil]-piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)-etil]piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)-etil]-piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)-etil]-piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]-piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)-propil]piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenil-amino)etil]-piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenil-amino)etil]piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]-piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]-piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-raetoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenil-tio)etil]piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentil-tio)etil]piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]-piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]-piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)-prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-propil]piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)-etil]piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)-etil]piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]-piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]-piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]-piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]-piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)-etil]-piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)-etil]-piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]-piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]-piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-propil]piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-propil]piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenil-amino)etil]piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenil-amino)etil]piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)-etil]piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)-etil]piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-propil]piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)-etil]piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)-etil]piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)-etil]piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-propil]piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-propil]piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)-etil]piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)-etil]piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)-etil]piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)-etil]piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-propil]piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-propil]piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)-etil]piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)-etil]piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)-etil]piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-propil]piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-propil]piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)-etil]piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenil-amino)etil]piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenil-amino)etil]piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluoro-fenoksi)etil]piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluoro-fenoksi)etil]piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluoro-fenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluoro-fenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-heptilpiperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-fenilbutil]-piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]-piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2-fluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(3-fluorofenil)-propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)-propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(4-fluorofenil)-butil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluoro-fenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,3-difluoro-fenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluoro-fenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,6-difluoro-fenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-difluoro-fenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-feniltio-propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-fluorofeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluorofeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-fluorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3-difluorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,6-difluorofeniltio)etil]piperidin-4-octena kiselina 4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-octena kiselina 4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-octena kiselina 4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-octena kiselina 4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-octena kiselina 4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2F3,5-trifluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-octena kiselina 4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-octena kiselina 4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-klorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-klorofeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-klorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-klorofeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-klorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-klorofeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metilfeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metilfeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metilfeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metilfeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metilfeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metilfeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-trifluorometilfeniltio)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-trifluorometilfeniltio)propil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-trifluorometilfeniltio)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-trifluorometilfeniltio)propil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-trifluorometilfeniltio)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-trifluorometilfeniltio)propil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metoksifeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metoksifeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metoksifeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metoksifeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metoksifeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metoksifeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[ciklopentilmetil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentil)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(ciklopentiltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(cikloheksiltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-2-il)butil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)tiopropil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-3-il)butil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-3-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)tiopropil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(1,3-tiazol-2-il)butil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-2-il)butil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)tiopropil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-3-il)butil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-3-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)tiopropil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-4-il)butil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-4-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)tiopropil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirazin-2-il)butil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirazin-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)tiopropil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4-difluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4-difluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-3-fluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-4-fluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-kloro-4-fluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-5-fluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-2-fluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluoro-4-metilfenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-bis(trifluorometil)fenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-4-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-5-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
123
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
124
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2F3,5-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-octena kiselina
127
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3~hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-heptilpiperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-fenilbutil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2-fluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(3-fluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(4-fluorofenil)butil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,3-difluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,6-difluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-difluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-feniltio-propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-fluorofeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluorofeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2- (4-fluorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3- (4-fluorofeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3-difluorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofeniltio)propil]piperidin-4-octena kiselina 4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,6-difluorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-octena kiselina 4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-octena kiselina 4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-octena kiselina 4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-octena kiselina 4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-octena kiselina 4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-octena kiselina 4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-klorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-klorofeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-klorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-klorofeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-klorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-klorofeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metilfeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metilfeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metilfeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metilfeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metilfeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metilfeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-trifluorometilfeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-trifluorometilfeniltio)propil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-trifluorometilfeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-trifluorometilfeniltio)propil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-trifluorometilfeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-trifluorometilfeniltio)propil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metoksifeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metoksifeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metoksifeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metoksifeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metoksifeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metoksifeniltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[ciklopentilmetil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentil)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(ciklopentiltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(cikloheksiltio)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-2-il)butil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)tiopropil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-3-il)butil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-3-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)tiopropil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(1,3-tiazol-2-il)butil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-2-il)butil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)tiopropil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-3-il)butil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-3-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)tiopropil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-4-il)butil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-4-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)tiopropil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirazin-2-il)butil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirazin-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)tiopropil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4-difluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4-difluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-3-fluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-4-fluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-kloro-4-fluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-5-fluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-2-fluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluoro-4-metilfenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-bis(trifluorometil)fenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-4-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-5-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-iljpropil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-octena kiselina 4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-octena kiselina 4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2- (2,4,6-trifluorofeniltio)etil]piperidin-4-octena kiselina 4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-octena kiselina 4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-octena kiselina 4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-octena
kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propilJpiperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-octena kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(3-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
octena kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-heptil-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-fenil-butil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(2-fluorofenil)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(3-fluorofenil)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(4-fluorofenil)butil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofenil)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,3-difluorofenil)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofenil)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,6-difluorofenil)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-difluorofenil)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)-propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-fenil-tiopropil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-fluorofeniltio)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluorofeniltio)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-fluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofeniltio)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3-difluorofenil-tio)etil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofenil-tio)propil]-piperidin-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,6-difluorofenil-tio)etil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenil-tio)etil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenil-tio)etil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenil-tio)etil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofeniltio)propil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-klorofeniltio)etil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-klorofeniltio)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-klorofeniltio)etil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-klorofeniltio)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-klorofeniltio)etil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-klorofeniltio)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metilfeniltio)etil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metilfeniltio)propil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metilfeniltio)etil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metilfeniltio)propil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metilfeniltio)etil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metilfeniltio)propil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-trifluorometilfeniltio)etil]-piperidin-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-trifluorometilfeniltio)propil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-trifluorometilfeniltio)etil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-trifluorometilfeniltio)propil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-trifluorometilfeniltio)etil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-trifluorometilfeniltio)propil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metoksifeniltio)etil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metoksifeniltio)propil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metoksifeniltio)etil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metoksifeniltio)propil]-piperidin-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metoksifeniltio)etil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metoksifeniltio)propil]-piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[ciklopentilmetil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentil)etil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(ciklopentiltio)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(cikloheksiltio)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-iljpropil]-1-[4-(tien-2-il)butil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)tiopropil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-3-il)butil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-3-il)tioetil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)tiopropil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(1,3-tiazol-2-il)butil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)tioetil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-2-il)butil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)tiopropil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-3-il)butil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-3-il)tioetil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)tiopropil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-4-il)butil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-4-il)tioetil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)tiopropil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)propil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirazin-2-il)butil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirazin-2-il)tioetil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)tiopropil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4-difluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4-difluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-3-fluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-4-fluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-kloro-4-fluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-5-fluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-2-fluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluoro-4-metilfenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-bis(trifluorometil)fenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-4-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-5-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]-piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]-piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]-piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]-piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]-piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenil-amino)etil]piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenil-amino)etil]piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)-etil]piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluoro-fenilamino)etil]-piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluoro-fenilamino)etil]-piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]-piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]-piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]-piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]-piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]-piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]-piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)-propil]piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]-piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)-etil]piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)-etil]piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]-piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]-piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tio-etil]piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tio-etil]piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]-piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-(cikloheksil)etil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenil-amino)etil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenil-amino)etil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)-etil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)-etil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)-etil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]-piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)-propil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)-etil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)-etil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)-etil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)-etil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)-etil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)-etil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)-etil]piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)-propil]piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenil-amino)etil]piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]-piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]-piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenil-tio)etil]piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)-etil]piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]-piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]-piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluoro-fenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluoro-fenil)propil]piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluoro-fenil)propil]piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenil-tio)etil]piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)-etil]piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)-etil]piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)-etil]piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)-etil]piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)-etil]piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-propil]piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-propil]piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]-piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]-piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenil-amino)etil]-piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenil-amino)etil]-piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]-piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]-piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-propil]piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-propil]piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenil-tio)etil]piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenil-tio)etil]piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenil-amino)etil]-piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenil-amino)etil]piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)-etil]piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluoro-fenoksi)etil]piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluoro-fenil)propil]piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenil-tio)etil]piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenil-tio)etil]piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenil-amino)etil]piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenil-amino)etil]piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)-etil]piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)-etil]piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenil-tio)etil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenil-tio)etil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenil-amino)etil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenil-amino)etil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)-etil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)-etil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-propil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-propil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)-etil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)-etil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenil-amino)etil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)-etil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)-etil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)-etil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-propil]piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-propil]piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)-etil]piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)-etil]piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenil-amino)etil]piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenil-amino)etil]piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)-etil]piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)-etil]piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-prop-2-inil]piperid-4-ilmetanol
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-heptilpiperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-fenilbutil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2-fluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(3-fluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(4-fluorofenil)-butil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofenil)-propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,3-difluorofenil)-propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofenil)-propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,6-difluorofenil)-propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-difluorofenil)-propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-feniltio-propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-fluorofenil-tio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluorofenil-tio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-fluorofenil-tio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil-tio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3-difluorofenil-tio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofenil-tio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,6-difluorofenil-tio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluoro-fenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluoro-fenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluoro-fenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluoro-fenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluoro-fenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluoro-fenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluoro-fenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluoro-fenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluoro-feniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-kloro-feniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-kloro-feniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-kloro-feniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-feniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-kloro-feniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-feniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metilfenil-tio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metilfenil-tio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metilfenil-tio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metilfenil-tio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metilfenil-tio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metilfenil-tio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-trifluorometil-feniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-trifluorometil-feniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-trifluorometil-feniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-trifluorometil-feniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-trifluorometil-feniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-trifluorometil-feniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metoksifenil-tio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metoksifenil-tio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metoksifenil-tio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metoksifenil-tio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metoksifenil-tio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metoksifenil-tio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[ciklopentilmetil]-piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentil)etil]-piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]-piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(ciklopentiltio)-propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(cikloheksiltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-2-il)butil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)tiopropil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-3-il)butil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)tiopropil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(1,3-tiazol-2-il)butil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-2-il)butil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)tiopropil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-3-il)butil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-3-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)tiopropil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-4-il)butil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-4-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)tiopropil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirazin-2-il)butil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirazin-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)tiopropil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4-difluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4-difluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-3-fluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-4-fluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-kloro-4-fluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-5-fluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-2-fluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluoro-4-metilfenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-bis(trifluorometil)fenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-4-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-5-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-{fenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2, 3,5-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propilJpiperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi) etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)-prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4/6-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-heptilpiperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-fenilbutil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2-fluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(3-fluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(4-fluorofenil)butil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,3-difluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,6-difluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-difluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-feniltio-propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-fluorofeniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluorofeniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-fluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofeniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3-difluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofeniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,6-difluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofeniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-klorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-klorofeniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-klorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-klorofeniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-klorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-klorofeniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metilfeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metilfeniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metilfeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metilfeniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metilfeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metilfeniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-trifluorometilfeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-trifluorometilfeniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-trifluorometilfeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-trifluorometilfeniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-trifluorometilfeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-trifluorometilfeniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metoksifeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metoksifeniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metoksifeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metoksifeniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metoksifeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metoksifeniltio)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[ciklopentilmetil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentil)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)-etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)-etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(ciklopentiltio)-propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(cikloheksiltio)-propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]-piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-2-il)butil]-piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)tiopropil]-piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)propil]-piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-3-il)butil]-piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]-piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-3-il)tioetil]-piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)tiopropil]-piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(1,3-tiazol-2-il)butil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-2-il)butil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)tiopropil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-3-il)butil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-3-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)tiopropil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-4-il)butil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-4-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)tiopropil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirazin-2-il)butil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirazin-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)tiopropil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4-difluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4-difluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-3-fluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-4-fluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-kloro-4-fluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-5-fluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-2-fluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluoro-4-metilfenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-bis(trifluorometil)fenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-1iazol-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-4-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-5-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-difluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperid-4-ilmetanol'
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperid-4-ilmetanol
195
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2R3,5-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperid-4-ilmetanol
201
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-iljpropil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperid-4-
ilmetanol
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-heptilpiperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-fenil-butil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propilj-1-[3-(fenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(2-fluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(3-fluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(4-fluorofenil)butil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,3-difluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,6-difluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-difluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-fenil-tiopropil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-fluorofeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluorofeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-fluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3-difluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,6-difluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2- (3,4,5-trifluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-klorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-klorofeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-klorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-klorofeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-klorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-klorofeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metilfeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metilfeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metilfeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metilfeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metilfeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metilfeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-trifluorometilfeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-trifluorometilfeniltio)propil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-trifluorometilfeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-trifluorometilfeniltio)propil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-trifluorometilfeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-trifluorometilfeniltio)propil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metoksifeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metoksifeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metoksifeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metoksifeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metoksifeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metoksifeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[ciklopentilmetil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentil)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(ciklopentiltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(cikloheksiltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-2-il)butil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)tiopropil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-3-il)butil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-3-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)tiopropil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(1,3-tiazol-2-il)butil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-2-il)butil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)tiopropil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-3-il)butil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-3-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)tiopropil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-4-il)butil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-4-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)tiopropil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirazin-2-il)butil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirazin-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)tiopropil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4-difluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4-difluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-3-fluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-4-fluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-kloro-4-fluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-5-fluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-2-fluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluoro-4-metilfenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-bistrifluorometilfenil)prop-2-inil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-4-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-5-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]-piperidin-4-hidroksamična
kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]-piperidin-4-hidroksamična
kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tio-etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)-etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]-piperidin-4-hidroksamična kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]-piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]-piperidin-4-hidroksamična
kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)-propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propilj-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična
kiselina
4-[3-(3-Morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-heptil piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-fenilbutil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2-fluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(3-fluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(4-fluorofenil)butil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,3-difluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,6-difluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-difluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-feniltiopropil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-fluorofeniltio)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluorofeniltio)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-fluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofeniltio)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3-difluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,6-difluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-klorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-klorofeniltio)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-klorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-klorofeniltio)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-klorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-klorofeniltio)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metilfeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metilfeniltio)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metilfeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metilfeniltio)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metilfeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metilfeniltio)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-trifluorometilfeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-trifluorometilfeniltio)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-trifluorometilfeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-trifluorometilfeniltio)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-trifluorometilfeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-trifluorometilfeniltio)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metoksifeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metoksifeniltio)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metoksifeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metoksifeniltio)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metoksifeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metoksifeniltio)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[ciklopentilmetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentil)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(ciklopentiltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(cikloheksiltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-2-il)butil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)tiopropil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-l-[4-(tien-3-il)butil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-3-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)tiopropil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(1,3-tiazol-2-il)butil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-2-il)butil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)tiopropil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-3-il)butil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-3-il)tioetil]piperidin-4-hidroksamična kiselina 4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)tiopropil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)propil]piperidin-4-hidroksamična kiselina 4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-4-il)butil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-4-il)tioetil]piperidin-4-hidroksamična kiselina 4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)tiopropil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirazin-2-il)butil]piperidin-4-hidroksamična kiselina 4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirazin-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)tiopropil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4-difluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4-difluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-3-fluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-4-fluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-kloro-4-fluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-5-fluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-2-fluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluoro-4-metilfenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-bistrifluorometilfenil)prop-2-inil]-piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)prop-2-inil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-4-il)prop-2-inil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-5-il)prop-2-inil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)prop-2-inil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)prop-2-inil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)prop-2-inil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3~hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propilJpiperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]-piperidin-
4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]-piperidin-
4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]-piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)-etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)-etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]-piperidin-
4-hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]-piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]-piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)-etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Hidroksi-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-heptilpiperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-fenilbutil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2-fluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(3-fluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(4-fluorofenil)butil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,3-difluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(2,6-difluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-difluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-feniltiopropil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-fluorofeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluorofeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-fluorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3-difluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofeniltio)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,6-difluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]-piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]-piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofeniltio)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-klorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-klorofeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-klorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-klorofeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-klorofeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-klorofeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metilfeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metilfeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metilfeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metilfeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metilfeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metilfeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-trifluorometilfeniltio)etil]-piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-trifluorometilfeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-trifluorometilfeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-trifluorometilfeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-trifluorometilfeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-trifluorometilfeniltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-metoksifeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-metoksifeniltio)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3-metoksifeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-metoksifeniltio)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(4-metoksifeniltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-metoksifeniltio)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[ciklopentilmetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentil)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(ciklopentiltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(cikloheksiltio)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-2-il)butil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)tiopropil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(tien-3-il)butil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-3-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)tiopropil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(1,3-tiazol-2-il)butil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-2-il)butil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)tiopropil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-3-il)butil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-3-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)tiopropil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirid-4-il)butil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-4-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)tiopropil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[4-(pirazin-2-il)butil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirazin-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirazin-2-il)tiopropil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)prop-2-inil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4-difluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4-difluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-3-fluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-4-fluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(2-kloro-4-fluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-kloro-5-fluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(4-kloro-2-fluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluoro-4-metilfenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-bistrifluorometilfenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(tien-3-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-2-il)prop-2-inil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-4-il)prop-2-inil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(1,3-tiazol-5-il)prop-2-inil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-2-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-3-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[3-(pirid-4-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična kiselina
253
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2F3,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propilJpiperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(cikloheksil)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(fenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(tien-2-il)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-metil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-diraetilamino-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-dimetilamino-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-hidroksamična
kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-hidroksimetil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-fluorometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-aminometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)propil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofeniltio)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenilamino)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(2,4,6-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(R,S)-Fluoro-3-(3-morfolinometil-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)prop-2-inil]piperidin-4-
hidroksamična kiselina
4-[3-(Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2-fluorofenil)alil]piperidin-4-karboksilna kiselina
4-[3-(Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3-fluorofenil)alil]piperidin-4-karboksilna kiselina
4-[3-(Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(4-fluorofenil)alil]piperidin-4-karboksilna kiselina
4-[3-(Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3-difluorofenil)alil]piperidin-4-karboksilna kiselina
4-[3-(Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4-difluorofenil)alil]piperidin-4-karboksilna kiselina
4-[3-(Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,6-difluorofenil)alil]piperidin-4-karboksilna kiselina
4-[3-(Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,5-difluorofenil)alil]piperidin-4-karboksilna kiselina
4-[3-(Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4-difluorofenil)alil]piperidin-4-karboksilna kiselina
4-[3-(Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,5-trifluorofenil)alil]piperidin-4-karboksilna kiselina
4-[3-(Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,4-trifluorofenil)alil]piperidin-4-karboksilna kiselina
4-[3-(Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,3,6-trifluorofenil)alil]piperidin-4-karboksilna kiselina
4-[3-(Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,5-trifluorofenil)alil]piperidin-4-karboksilna kiselina
4-[3-(Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,4,6-trifluorofenil)alil]piperidin-4-karboksilna kiselina
4-[3-(Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,4,5-trifluorofenil)alil]piperidin-4-karboksilna kiselina
4-[3-(Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(3,5,6-trifluorofenil)alil]piperidin-4-karboksilna kiselina
Primjeri koji slijede na ne ograničavajući način opisuju prikazani izum.
Primjer 1
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]-piperidin-4-karboksilna kiselina dihidroklorid
Smjesa 0.6 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]-piperidin-4-karboksilat u 7.72 cm3 vodene otopine 6N klorovodične kiseline ostavljena je na temperaturi od 100°C uz miješanje u inertnoj atmosferi tijekom 2 sata. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do suhoće pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveni ostatak je stavljen u 10 cm3 smjese diklorometana/metanola (90/10 volumena). Smjesa je koncentrirana do isušenja pod prethodno navedenim uvjetima. Dobiveno je 0.58 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]-piperidin-4-karboksilna kiselina dihidroklorida u obliku bež obojene pjene točke taljenja na 130°C uz raspadanje.
1H NMR spektar (250 MHz, (CD3)2SO-d6 na temperaturi od 373 K, δ u ppm): od 1.50 do 2.30 (mts: 8H u cijelosti); od 2.70 do 3.80 (mts: 10H u cijelosti); 3.99 (s: 3H); 7.09 (dd, J = 5 i 3.5 Hz: 1H); 7.29 (široko d, J = 3.5 Hz; 1H); 7.40 (d, J = 2.5 Hz: 1H); 7.46 (dd, J = 9 i 2.5 Hz: 1H); 7.64 (široko d, J = 5 Hz: 1H); 7.99 (d, J = 9 Hz: 1H); 8.67 (s: 1H).
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il) tioetil]-piperidin-4-karboksilat
Smjesa od 0.6 g benzil 4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilata, 0.36 g 2-(2-bromoetiltio)tiofena i 0.22 g kalijeva karbonata u 20 cm3 acetonitrila je zagrijavana tijekom 16 sati na temperaturi od 80°C, uz miješanje i pod inertnom atmosferom. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je koncentrirana pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom, pod tlakom dušika od 100 kPa, na stupcu silikagela (veličine čestice 40-63 μ; promjera 3.5 cm; visine 28 cm), te je eluiran sa smjesom diklorometana/metanola (97.5/2.5 u volumenu) i sakupljene su 35-cm3 frakcije. Frakcije 15 do 20 su kombinirane, a zatim koncentrirane do isušenja pod gore navedenim uvjetima. Dobiveno je 0.67 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]-piperidin-4-karboksilata u obliku narančastog viskoznog ulja.
Infra-crveni spektar (CCl4) 2955; 1727; 1622; 1503; 1229; 1117; 833 i 698 cm-1.
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat
Dodano je 1.27 cm3 trifluorooctene kiseline, uz miješanje i pod inertnom atmosferom, na temperaturi od 20°C, otopini 2.05 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1 (terc-butiloksikarbonil)-piperidin-4-karboksilat u 50 cm3 trifluorooctene kiseline, te nakon daljnjih 30 minuta, dodano je još 1.27 cm3. Reakcija je završena konačnim dodavanjem 1.27 cm3 trifluorooctene kiseline. Nakon jednog sata, reakcijska smjesa je koncentrirana pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Ostatak nakon uparavanja je obrađen sa 50 cm3 etilnog acetata i 20 cm3 vode. Nakon dodavanja 5 g kalijeva karbonata i miješanja tijekom 5 minuta, faze su ostavljene da se razdvoje taloženjem, a organska faza je odvojena s 20 cm3 10% vodene otopine (težine) otopine natrijeva klorida. Nakon isušenja na magnezijevom sulfatu, a zatim filtracije, organska otopina je koncentrirana pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom, pod tlakom dušika od 100 kPa, na stupcu silikagela (veličina čestice 40-63 μ; promjer 3.5 cm; visina 30 cm), eluiranjem sa smjesom diklorometan/metanola/32% vodene otopine amonijaka (89/10/1 volumena), i sakupljanjem 40-cm3 frakcija. Frakcije 14 do 23 se kombiniraju, a zatim koncentriraju do isušenja pod gore navedenim uvjetima. Dobiveno je 1.36 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata u obliku bež krute tvari točke taljenja na 95°C.
Infra-crveni spektar (KBr) 2960; 1721; 1621; 1503; 1232; 1115; 829 i 744 cm-1.
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(terc-butiloksikarbonil) -piperidin-4-karboksilat.
1.98 g benzil 4-alil-1-(terc-butiloksikarbonil)piperidin-4-karboksilata je ohlađeno na temperaturu od -30°C i dodano je 11.32 cm3 0.5 M otopine 9-borabiciklo[3,3,l]nonana u tetrahidrofuranu uz miješanje pod inertnom atmosferom. Nakon dodavanja, temperatura smjese je dovedena na 20°C. Dobivena otopina je miješana tijekom daljnja 4 sata, a zatim je slijedilo dodavanje 40 cm3 dioksana, 0.183 g difenil-fosfinoferocenpaladijeva klorida, 2 g 4-bromo-3-kloro-6-metoksikinolina i 3.0 g tribazičnog kalijeva fosfata. Nakon miješanja tijekom 16 sati na temperaturi od 60°C, reakcijska smjesa je ohlađena na približno 20°C i filtrirana. Netopljivi materijal je ispran tri puta s 20 cm3 etilnog acetata, a zatim je kombinirano filtriranje i ispiranje vodom, te miješanje s 40 cm3 vode i 100 cm3 etilnog acetata. Organska faza je odvojena taloženjem, isprana dva puta s 20 cm3 vode i 40 cm3 10% vodene otopine (po težini) natrijeva klorida, isušena magnezijevim slufatom, filtrirana i koncentrirana pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom, pod tlakom dušika od 100 kPa, na stupcu silikagela (veličina čestice 40-63 μ; promjer 3.5 cm; visina 30 cm), eluiranjem sa smjesom diklorometan/metanola (98.5/1.5 volumena), i sakupljanjem 35-cm3 frakcija. Frakcije 22 do 29 su kombinirane, a zatim koncentrirane pod gore navedenim uvjetima. Dobiveno je 2.09 g 4-[3-(3-kloro-6-metoksi-kinolin-4-il)propil]-1-(terc-butiloksikarbonil)-piperidin-4-karboksilata u obliku gustog žutog ulja.
Infra-crveni spektar (CCl4) 2930; 1728; 1695; 1622; 1503; 1230; 1172; 833 i 697 cm -1.
Benzil 4-alil-1-(terc-butiloksikarbonil)piperidin-4-karboksilat.
15.4 g kalijeva karbonata, a zatim 10.6 cm3 benzil bromida je dodano, na temperaturi od 20°C, uz miješanje i u inertnoj atmosferi, otopini od 20 g 4-alil-1-(terc-butiloksikarbonil) piperidin-4-karboksilne kiseline u 200 cm3 dimetilformamida. Smjesa je miješana tijekom 16 sati na temperaturi od približno 20°C, a zatim filtrirana. Netopljivi materijal je ispran dva puta sa 100 cm3 etilnog acetata. Filtracija i ispiranje su kombinirani, te je 250 cm3 vode dodano i smjesa je zatim ekstrahirana jedanput s 500 cm3 i jedanput sa 150 cm3 etilnog acetata. Organski ekstrakti su kombinirani, isprani dva puta sa 125 cm3 10% vodene otopine (po težini) natrijeva klorida, isušeni magnezijevim sulfatom, filtrirani i koncentrirani pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveno ulje je pročišćeno kromatografijom, pod tlakom od 100 kPa dušika, na stupcu silikagela (veličina čestice 40-63 μ; promjer 7 cm; visina 30 cm), eluiranjem sa smjesom diklorometan/metanola (99/1 volumena), i sakupljanjem 200-cm3 frakcija. Frakcije 6 do 16 su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveno je 25 g benzil 4-alil-1-(terc-butiloksikarbonil)piperidin-4-karboksilata u obliku svijetložute tekućine.
Infra-crveni spektar (CH2Cl2) 2980; 1725; 1683; 1426; 1171; 1142; 974 i 624 cm-1.
4-Alil-1-(terc-butiloksikarbonil)piperidin-4-karboksilna kiselina.
4.44 cm3 vode, a zatim 30.62 g etil 4-alil-1-(terc-butiloksikarbonil) -piperidin-4-karboksilata prethodno otopljenog u 150 cm3 tetrahidrofurana je dodano, uz miješanje i u inertnoj atmosferi, smjesi 48.52 g kalijeva terc-butoksida u 350 cm3 tetrahidrofurana, te ohlađeno na temperaturu od 0°C. Nakon što je smjesa ostavljena da se ugrije na 20°C, smjesa je miješana tijekom 24 sata na navedenoj temperaturi i zatim koncentrirana do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Vodeni ostatak je ekstrahiran s 300 cm3 dietilnog etera. Nakon stajanja tijekom 16 sati, vodena faza je zakiseljena na pH vrijednosti od 3 do 4 dodatkom približno 215 cm3 vodene otopine klorovodične kiseline, a zatim je ekstrahirana sa 3 puta 300 cm3 dietilnog etera. Eterski ekstrakti su kombinirani, isušeni magnezijevim sulfatom, filtrirani i koncentrirani do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveno je 26.1 g 4-alil-1-(terc-butiloksikarbonil)piperidin-4-karboksilne kiseline u obliku prljavo bijele krute tvari.
Spektar mase: EI m/z 269 M+ m/z=168 (M - C5C9O2)+
m/z=124 (m/z=168 - CO2) + m/z=57 C4H9+
bazni vršak
Etil alil-1-(terc-butiloksikarbonil)piperidin-4-karboksilat.
Dodano je 70 cm3 otopine butillitija u heksanu (2.5M koncentracije), uz miješanje u inertnoj atmosferi, u 150 cm3 tetrahidrofurana ohlađenog na -70°C, a zatim je dodano 50 cm3 tetrahidrofurana i 23 cm3 diizopropilamina prethodno otopljenog u 300 cm3 tetrahidrofurana. Nakon daljnjeg dodavanja 50 cm3 tetrahidrofurana, smjesa je miješana tijekom 15 min na približno -70°C, a zatim je dodano 45.15 g etilnog l-(terc-butiloksikarbonil) izonipekotata prethodno otopljenog u 400 cm3 tetrahidrofurana, te na kraju 50 cm3 istog solventa. Nakon miješanja smjese tijekom l sata na temperaturi od -70°C, dodano je 16.7 cm3 alilnog bromida prethodno otopljenog u 150 cm3 tetrahidrofurana i smjesa je zatim ugrijana na 20°C, te miješana tijekom 17 sati. Smjesa je izlivena u 200 cm3 zasićene vodene otopine amonijeva klorida i zatim ekstrahirana s 2 litre etilnog acetata. Kombinirani ekstrakti su isušeni natrijevim sulfatom, filtrirani i koncentrirani pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveno je ulje, koje je zatim pročišćeno kromatografijom, pod tlakom dušika od 100 kPa, na stupcu silikagela (promjer 12 cm, visina 50 cm), te eluirano smjesnom diklorometan/metanol (99.5/0.5 volumena) i sakupljene su 200-cm3 frakcije. Frakcije 20 do 84 su kombinirane i koncentrirane pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveno je 27.85 g etil 4-alil-1-(terc-butiloksikarbonil)-piperidin-4-karboksilata u obliku žutog ulja.
Spektar mase: EI m/z 297 M+ m/z=240 (M - C4H9)+
m/z=196(m/z=240 - CO2)+ m/z=168
(m/z=240 - CO2Et)+ m/z=124
(m/z=168 – CO2)+ m/z=57 C4H9+ bazni vršak
Etil 1-(terc-butiloksikarbonil)izonipekotat.
88.3 cm3 trietilamina je dodavano tijekom 1 sata, uz miješanje u inertnoj atmosferi u otopinu od 100 g etilnog izonipekotata u 1500 cm3 diklorometana ohlađenog na temperaturu od 5°C, a zatim, tijekom istog perioda, dodano je 300 cm3 diklorometana. Reakcijska smjesa je miješana tijekom 16 sati pri čemu se temperatura vraćala na 20°C. Nakon daljnjeg dodavanja 41.6 g di-terc-butil dikarbonata otopljenog u 70 cm3 diklorometana, reakcijska smjesa je miješana tijekom 3 sata na temperaturi od 20°C, a zatim isprana s dva puta po 600 cm3 zasićene vodene otopine natrijeva klorida, isušena na natrijevom sulfatu, filtrirana i koncentrirana pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveno je 171 g etil l-(terc-butiloksikarbonil)izonipekotata u obliku smeđeg ulja. Spektar mase: DCI m/z=275 MNH/ bazni vršak m/z=258 MH+
2-(2-Bromoetilsulfanil)tiofen se može pripraviti prema Sadykhovk, K.I., Aliev, S.M. i Seidov, M.M. Khim. Getgerotsikl. Soedin, 3, 344-5 (1975).
4-Bromo-3-kloro-6-metoksikinolin
Smjesa 20 g 3-kloro-4-hidroksi-6-metoksikinolina u 1000 cm3 acetonitrila, u koju je dodano 80.8 g trifenilfosfin bromida, miješana je tijekom 2 sata i 30 minuta na temperaturi od 85°C. Dobivena otopina je ohlađena na 20°C, a zatim miješana tijekom 16 sati na istoj temperaturi. Reakcijska smjesa je koncentrirana pod sniženim tlakom (5 kPa) na temperaturi od 40°C, a uhlapljeni ostatak je zatim obrađen s 200 cm3 zasićene vodene otopine natrij hidrogen karbonata i 200 cm3 etilnog acetata. Organska faza je odvojena nakon taloženja, te isprana dva puta s 200 cm3 destilirane vode. Vodena faza je ekstrahirana još jedanput s etilnim acetatom, a organski ekstrakti su zatim kombinirani, isušeni magnezijevim sulfatom, filtrirani i koncentrirani pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveni produkt je pročišćen kromatografijom pod tlakom dušika od 100 kPa, na stupcu silikagela (promjer 7.5 cm; masa silicija 700 g), te eluiran smjesom cikloheksan/etilni acetat (70/30 volumena). Sakupljene su frakcije koje odgovaraju očekivanom produktu. Navedene frakcije su kombinirane, a zatim koncentrirane pod gore navedenim uvjetima. Dobiveno je 20.7 g 4-bromo-3-kloro-6-metoksikinolina u obliku bijele krute tvari točke taljenja 108°C. Spektar mase: EI m/z 271 M+ vršak baze m/z=256
(M - CH3)+ m/z=228 (m/z=256 – CO)+
m/z=149 (m/z=228 - Br)+
m/z=114 (m/z=149 - Cl)+
3-Kloro-4-hidroksi-6-metoksikinolin.
14.26 g N-klorosukcinimida je dodano, na temperaturi od 20°C uz miješanje smjesi od 17 g 4-hidroksi-6-metoksikinolina u 700 cm3 octene kiseline i smjesa je zatim zagrijavana na temperaturi između 50 i 70°C tijekom 4 sata. Dobivena otopina je zatim ohlađena na približno 20°C i zatim koncentrirana do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Kruti ostatak je obrađen sa 250 cm3 zasićene vodene otopine natrijeva hidrogen karbonata. Smjesa je miješana tijekom l sata. Netopljivi materijal je filtracijom uklonjen, te je smjesa isprana 3 puta sa 250 cm3 vode. Dobiveni kristali su isušivani pod sniženim tlakom (10 kPa) tijekom 3 sata na temperaturi od 20°C. Dobiveno je 20 g 3-kloro-4-hidroksi-6-metoksikinolina u obliku žute krute tvari. Spektar mase: EI m/z 209 M+' vršak baze m/z=194
(M - CH3)+ m/z=166 (m/z=194 - CO)+
4-hidroksi-6-metoksikinolin.
Suspenzija od 53.5 g 4-hidroksi-6-metoksikinolin-3-karboksilne kiseline u 1000 cm3 difenilnog etera zagrijavana je uz miješanje, na temperaturi između 250°C i 260°C, tijekom 2 sata i 45 minuta. Reakcijska smjesa je ohlađena na 20°C. Nakon miješanja tijekom 16 sati na navedenoj temperaturi, smjesa je izlivena uz miješanje u l litru pentana, a zatim je filtrirana. Dobivena masa je isprana s tri puta po 100 cm3 pentana, a zatim s 3 puta po 100 cm3 diizopropilnog etera. Nakon sušenja na zraku, dobiveno je 37 g 4-hidroksi-6-metoksikinolina u obliku bež krute tvari.
Spektar mase: DCI m/z 176 M+ vršak baze
4-Hidroksi-6-metoksikinolin-3-karboksilna kiselina se može pripraviti prema B.R. Baker i Ray R. Bramhall, J. Med. Chem.LS, 230 (1972).
Primjer 2
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]-piperidin-4-karboksilna kiselina.
Smjesa 0.7 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)-etil]piperidin-4-karboksilata u 10 cm3 vodene otopine 5M klorovodične kiseline miješana je tijekom 5 sati na temperaturi od 100°C. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod tlakom dušika od 100 kPa, na stupcu silikagela (veličina čestice 40-63 μ; promjer 2.5 cm; visina 35 cm), eluiranjem sa smjesom diklorometan/metanol/28% vodena otopina amonijaka (89/10/1 volumena), te sakupljanjem 25-cm3 frakcija. Frakcije 16 do 25 su sakupljene. Navedene frakcije su zatim kombinirane i koncentrirane pod gore navedenim uvjetima. Dobiveni ostatak nakon uhlapljenja je stavljen u 10 cm3 diizopropilnog etera. Nastali kristalni produkt je filtracijom odvojen, ispran dva puta s 5 cm3 istog solventa i isušen na zraku. Dobiveno je 0.37 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]-piperidin-4-karboksilne kiseline u obliku bijele krute tvari točke taljenja 204°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.20 do 2.15 (mt: 10H); 2.62 (t, J = 5.5 Hz: 2H); od 2.65 do 2.80 (mt: 2H); 3.18 (mt: 2H); 3.96 (s: 3H); 4.08 (t, J = 5.5 Hz: 2H); od 6.60 do 6.85 (mt: 3H); 7.38 (d, J = 2.5 Hz: 1H); 7.46 (dd, J = 9 i 2.5 Hz: 1H); 8.68 (s: 1H).
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]-piperidin-4-karboksilat.
Suspenzija koja se sastoji od 1.36 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.95 g 1-(2-bromoetoksi)-3,5-difluoro-benzena (90% čistoće) i 0.5 g kalijeva karbonata u 45 cm3 acetonitrila je zagrijavana na temperaturu od 80°C tijekom 16 sati, uz miješanje u inertnoj atmosferi. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je filtrirana, a netopljivi materijal je ispran acetonitrilom. Filtrat i voda za ispiranje su kombinirani i koncentrirani pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je pročišćen kromatografijom pod tlakom dušika od 100 kPa, na stupcu silikagela (veličina čestice 40-63 μ; promjer 3.5 cm; visina 45 cm), eluiranjem sa smjesom diklorometan/metanol (97/3 volumena), te sakupljanjem 40-cm3 frakcija. Frakcije 18 do 23 su sakupljene. Navedene frakcije su zatim kombinirane i koncentrirane do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveno je 1.56 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]-piperidin-4-karboksilata u obliku narančasto obojenog ulja.
Infra-crveni spektar (CH2Cl2) : 2955; 1723; 1622; 1599; 1229; 1153; 1116 i 843 cm-1.
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil] piperidin-4-karboksilat je pripravljen u skladu s Primjerom 1.
Primjer 3
4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(2-cikloheksiletil)piperidin-4-karboksilna kiselina.
Smjesa 0.6 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(2-cikloheksiletil)-piperidin-4-karboksilata u 9 cm3 vodene otopine 5M klorovodične kiseline zagrijavana je na temperaturu od 100°C uz miješanje tijekom 5 sati. Dobivena otopina je koncentrirana pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je stavljen u diizopropilni eter. Dobiveni kristalni produkt je filtracijom odvojen, ispran istim solventom i isušen u pećnici na temperaturi od 60°C, pod sniženim tlakom (10 kPa). Dobivena je kruta tvar, koja je zatim pročišćena kromatografijom pod tlakom dušika od 100 kPa, na stupcu silikagela (veličina čestice 40-63 μ; promjer 2.5 cm; visina 40 cm), eluiranjem sa smjesom diklorometan/metanol/32% vodena otopina amonijaka (89/10/1 volumena), te sakupljanjem 25-cm3 frakcija. Frakcije 16 do 25 su sakupljene i koncentrirane pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiven je kristalni produkt je umiješan u 5 cm3 diizopropilnog etera. Nastali produkt je filtracijom odvojen, ispran istim solventom i isušen na zraku. Dobiveno je 0.33 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(2-cikloheksiletil)-piperidin-4-karboksilne kiseline u obliku bijele krute tvari točke taljenja 234°C.
1H NMR spektar (300 MHz, CD3OD-d4, δ u ppm) : od 0.95 do 2.20 - 2.42 - od 2.90 do 3.15 i od 3.30 do 3.50 (odnosno, mt, široki d, J = 13.5 Hz, mt i mt: 29H ukupno); 4.11 (s: 3H); 7.52 (mt: 2H); 8.02 (široko d, J = 9 Hz: 1H); 8.68 (s: 1H).
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(2-cikloheksiletil)piperidin-4-karboksilat.
Dodano je 0.56 cm3 2-cikloheksil bromida i 0.5 g kalijeva karbonata, uz miješanje u inertnoj atmosferi, na temperaturi od 20°C, u otopinu od 1.36 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata u 50 cm3 acetonitrila. Dobivena suspenzija je zagrijavana na 80°C tijekom 16 sati, a nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je filtrirana i koncentrirana do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod tlakom dušika od 100 kPa, na stupcu silikagela (veličina čestice 40-63 μ; promjer 3.5 cm; visina 45 cm), eluiranjem sa smjesom diklorometan/metanol (97/3 volumena), te sakupljanjem 40-cm3 frakcija. Frakcije 22 do 30 su kombinirane i koncentrirane do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveno je 1.33 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(2-cikloheksil)piperidin-4-karboksilata u obliku narančasto obojenog ulja.
Infra-crveni spektar (CCl4) : 2925; 1727; 1622; 1503; 1230; 1116; 833 i 697 cm-1.
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil] piperidin-4-karboksilat je pripravljen u Primjeru 1.
Primjer 4
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)-piperidin-4-karboksilna kiselina dihidroklorid.
0.5 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)-piperidin-4-karboksilat u 8 cm3 5N klorovodične kiseline zagrijavano je na temperaturi od 100°C uz miješanje tijekom 5 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Ostatak dobiven uparavanjem je obrađen sa 6 cm3 smjese diklorometana/metanola (90/10 volumena), a smjesa je ponvno koncentrirana do isušenja pod prethodno navedenim uvjetima. Dobivena je pjena, koja je zatim obrađena sa 5 cm3 diizopropilnog etera. Dobiveni kristalni produkt je zatim filtracijom odvojen, ispran tri puta sa 5 cm3 prethodno navedenog solventa i isušen u peći pod sniženim tlakom (10 kPa) na temperaturi od 50°C. Dobiveno je 0.46 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)piperidin-4-karboksilne kiseline dihidroklorida u obliku bež obojene krute tvari.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.40 do 2.25 i od 2.50 do 3.60 (mts: 20H ukupno); 3.96 (s: 3H); od 7.10 do 7.45 (mt: 5H); 7.39 (d, J = 2.5 Hz: 1H); 7.47 (dd, J = 9 i 2.5 Hz: 1H); 7.98 (d, J = 9 Hz: 1H); 8.70 (s: 1H);
[lakuna]
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)piperidin-4-karboksilat.
Smjesa koja sa sastoji od 1.36 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.55 cm3 l-bromo-3-fenilpropana i 0.5 g kalijeva karbonata u 45 cm3 acetonitrila je zagrijavana uz miješanje u inertnoj atmosferi tijekom 16 sati na temperaturi od 80°C. Nakon hlađenja, reakcijska smjesa je filtrirana, a netopljivi materijal je zatim ispran acetonitrilom. Filtrat je koncentriran do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveno je ulje, koje je zatim pročišćeno kromatografijom pod tlakom dušika od 100 kPa, na stupcu silikagela (veličina čestice 40-63 μ; promjer 3.5 cm; visina 30 cm), eluiranjem sa smjesom diklorometan/metanol (97/3 volumena), te sakupljanjem 40-cm3 frakcija. Frakcije 21 do 25 su kombinirane i koncentrirane kao što je gore navedeno. Dobiveno je 21 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)-piperidin-4-karboksilata u obliku narančasto obojenog ulja.
Infra-crveni spektar (CH2Cl2) : 2948; 2812; 1722; 1622; 1504; 1229; 1118 i 834 cm-1.
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil] piperidin-4-karboksilat je pripravljen u Primjeru 1.
Primjer 5
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna kiselina trihidroklorid.
Smjesa 0.4 g etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilata u 7 cm3 vodene otopine 5M klorovodične kiseline održavana je na temperaturi od 100°C uz miješanje u inertnoj atmosferi tijekom 4 sati. Nakon hlađenja na 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen sa 10 cm5 smjese diklorometan/metanol (90/10 volumena). Smjesa je koncentrirana do isušenja prema prethodno navedenim uvjetima. Dobiveno je 0.45 g 4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilna kiselina trihidroklorida u obliku pjene koja se topi i raspada na 132°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.59 (mt: 2H); od 1.65 do 1.95 (mt: 4H); 2.20 (široko d, J = 13.5 Hz: 2H); 2.86 (mt: 2H); od 3.10 do 3.65 (mt: 8H); 3.99 (s: 3H); 7.19 (široko dd, J = 7.5 i 4.5 Hz: 1H); od 7.35 do 7.50 (mt: 2H); 7.50 (dd, J = 9 i 3 Hz: 1H); 7.71 (otopljeno t, J = 7.5 i 1.5 Hz: 1H); 8.01 (d, J = 9 Hz: 1H); 8.48 (široko d, J = 4.5 Hz: 1H); 8.74 (s: 1H); 10.70 (mnnogostruko: 1H).
Etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il) tioetil]piperidin-4-karboksilat.
Etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(pirid-2-il)tioetil]piperidin-4-karboksilat je pripravljen analogno postupku iz Primjera l, počevši od etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilat hidroklorida.
Infra-crveni spektar (CCl4) : 2955; 1726; 1622; 1580; 1503; 1414; 1229; 1125; 1030 i 833 cm-1.
Etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat hidroklorid.
Smjesa 2.6 g etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(terc-butiloksikarbonil)-piperidin-4-karboksilata u 40 cm3 dioksana, u koju je dodano 14 cm3 4 N klorovodičnog dioksana, miješana je tijekom 16 sati na temperaturi od 20°C. Dobivena suspenzija je razrijeđena dodavanjem 100 cm3 dietilnog etera, te je miješana na 20°C tijekom l sata, a zatim filtrirana. Masa je isprana dva puta s 40 cm3 dietilnog etera, a zatim isušena u sušilici pod sniženim tlakom (5 kPa). Dobiveno je 1.9 g etilnog 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata u obliku bijele krute tvari.
Infra-crveni spektar (KBr): 2965; 2474; 1720; 1620; 1584; 1416; 1241; 1119; 1019; 872 i 743 cm-1.
Etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(terc-butiloksikarbonil)piperidin-4-karboksilat.
30 cm3 0.5M otopine 9-borabiciklo[3.3.1]nonana u tetrahidrofuranu je dodano otopini 2.96 g etilnog 4-alil-1-(terc-butiloksikarbonil)-piperidin-4-karboksilata u 30 cm3 tetrahidrofurana, uz miješanje na temperaturi od -10°C u inertnoj atmosferi, te održavanje temperature ispod 0°C. Nakon dodavanja, temperatura smjese je dovedena na približno 20°C i smjesa je zatim miješana tijekom daljnja 4 sata. Dodano je 3.1 g 4-bromo-3-kloro-6-metoksikinolina, zatim 50 cm3 dioksna, 6.4 g tribazičnog kalijevog fosfata i 0.22 g difenilfosfinoferocen paladijeva klorida. Reakcijska smjesa je zagrijavana na temperaturu od 50°C tijekom 16 sati. Nakon hlađenja na temperaturu od 20°C, smjesa je filtrirana i masa je zatim isprana 3 puta sa 50 cm3 etilnog acetata. Filtrat je ispran sa 100 cm3 vode, a zatim sa dva puta po 50 cm3 zasićene vodene otopine natrijeva klorida. Organska faza je isušena magnezijevim sulfatom, filtrirana i koncentrirana pod sniženim tlakom (5 kPa), na temperaturi od 40°C. Dobiveno je smeđe ulje, koje je zatim pročišćeno kromatografijom, pod tlakom od 50 kPa dušika, na stupcu silikagela (veličina čestice 20-45 μ; promjer 4.5 cm; visina 42 cm), eluiranjem sa smjesom cikloheksan/etilni acetat (80/20 volumena). Sakupljene su frakcije koje sadrže očekivani produkt. Navedene frakcije su kombinirane, a zatim koncentrirane pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveno je 2.62 g etilnog 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(terc-butiloksikarbonil)piperidin-4-karboksilata u obliku žutog ulja.
Infra-crveni spektar (CH2Cl2) : 1720; 1682; 1622; 1504; 1423; 1367; 1229; 1174; 1027 i 834 cm-1.
Etil 4-alil-1-(terc-butiloksikarbonil)-piperidin-4-karboksilat je pripravljen u Primjeru 1.
Primjer 6
Natrijeva sol 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-heptilpiperidin-4-karboksilne kiseline.
Smjesa od 0.48 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-heptilpiperidin-4-karboksilata u u 7 cm3 vodene otopine 5 M klorovodične kiseline održavana je na temperaturi od 100°C uz miješanje u inertnoj atmosferi tijekom 6 sati. Nakon hlađenja na 20°C, reakcijska smjesa je miješana tijekom 24 sata, a zatim uparena pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod tlakom dušika od 100 kPa, na stupcu silikagela (veličina čestice 40-63 μ; promjer 2.5 cm; visina 35 cm), eluiranjem sa smjesom diklorometan/metanol/vodena otopina amonijaka (84/15/1 volumena), te sakupljanjem 40-cm3 frakcija. Frakcije 19 do 24 su kombiniran, a potom koncentrirane prema prethodno navedenim uvjetima. Dobivena kruta tvar je umiješana u 10 cm3 diizopropilnog etera, filtrirana i isprana sa 3 puta po 5 cm3 diizopropilnog etera. Dobiveno je 0.35 g natrijeve soli 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-heptilpiperidin-4-karboksilne kiseline u obliku krute tvari točke taljenja 223°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, S u ppm) : 0.87 (t, J = 7 Hz: 3H); od 1.10 do 1.45 (mt: 12H); od 1.45 do 1.70 (mt: 4H); od 1.85 do 2.05 (mt: 2H); 1.97 (široko d, J = 10.5 Hz: 2H); 2.17 (široko t, J = 7.5 Hz: 2H); od 2.45 do 2.60 (mt: 2H); 3.15 (mt: 2H); 3.97 (s: 3H); 7.40 (mt: 1H); 7.44 (dd, J -9 i 3 Hz: 1H); 7.95 (d, J = 9 Hz: 1H); 8.66 (s: 1H).
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-heptilpiperidin-4-karboksilat.
1.36 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata i 0.5 g kalijeva karbonata je dodanok, na temperaturi od 20°C, uz miješanje u inertnoj atmosferi, otopini od 0.61 cm3 1-jodoheptana u 45 cm3 acetonitrila. Nakon zagrijavanja tijekom 18 sati na temperaturi od 80°C, dodano je daljnjih 1.17 cm3 1-jodoheptana. Nakon zagrijavanja tijekom 40 sati na temperaturi od 80°C/ reakcijska smjesa je ohlađena na 20°C, filtrirana i koncentrirana pod sniženim tlakom (l kPa) na temperaturi od 50°C. Dobiveni ostatak je pročišćen kromatografijom pod tlakom dušika od 100 kPa, na stupcu silikagela (veličina čestice 40-60 μ; promjer 3.5 cm; visina 35 cm), eluiranjem sa smjesom diklorometan/metanol (95/05 volumena), te sakupljanjem 35-cm3 frakcija. Frakcije 18 do 26 su kombinirane, a zatim koncentrirane kao što je gore navedeno. Dobiveno je 0.36 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-heptilpiperidin-4-karboksilata.
Infra-crveni spektar (CH2Cl2) : 2957; 2931; 1722; 1622; 1504; 1229; 1159; 1118; [lakuna]
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat je pripravljen u Primjeru 1.
Primjer 7
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilna kiselina dihidroklorid.
Smjesa od 0.55 g etilnog 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilata u 8 cm3 vodene otopine 6 N klorovodične kiseline, zagrijavana je na temperaturi od 100°C, uz miješanje u inertnoj atmosferi, tijekom 5 sati. Nakon miješanja tijekom 18 sati na temperaturi od 20 °C, dobivena otopina je koncentrirana pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Ostatak dobiven uparavanjem je obrađen sa 10 cm3 smjese diklorometan/metanol (90/10 volumena), a zatim koncentriran pod istim uvjetima kao što je prethodno navedeno. Dobiveno je 0.59 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilne kiseline dihidroklorida u obliku pjene koja se topi na 129°C uz omekšavanje.
1H NMR spektar (300 MHz, (CD3)2SO-d6, Z u ppm) : od 1.30 do 2.10 (mt: 14H); 2.15 (široko d, J = 13.5 Hz: 2H); od 2.65 do 3.00 (mt: 4H); od 3.05 do 3.40 (mt: 5H); 3.46 (široko d, J = 12 Hz: 2H); 3.97 (s: 3H); 7.42 (d, J = 2.5 Hz: 1H); 7.48 (dd, J = 9 i 2.5 Hz: 1H); 7.99 (d, J = 9 Hz: 1H); 8.72 (s: 1H); od 10.55 do 10.90 (multiplo: 1H).
Etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilat.
1.2 g etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata i 0.51 g kalijeva karbonata i 0.61 g kalijeva jodida je dodano, na temperaturi od 20°C, uz miješanje u inertnoj atmosferi, otopini od 0.607 g (2-kloroetiltio)ciklopentana u 50 cm3 acetonitrila. Nakon zagrijavanja tijekom 20 sati na temperaturi od 80°C, reakcijska smjesa je ohlađena na 20°C, filtrirana i koncentrirana pod sniženim tlakom (l kPa) na temperaturi od 50°C. Dobiveni ostatak je pročišćen kromatografijom pod tlakom dušika od 100 kPa, na stupcu silikagela (veličina čestice 40-60 μ; promjer 3.5 cm), eluiranjem sa smjesom [lakuna] 35 cm3 [lakuna]. Frakcije 25 do 31 su kombinirane, a zatim koncentrirane kao što je gore navedeno. Dobiveno je 0.9 g etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-karboksilata.
Infra-crveni spektar (CCl4) : 958; 1726; 1622; 1503; 1229; 1117; 1030 i 833 cm-1.
Etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat je pripravljen kao što je opisano u Primjeru 5.
Primjer 8
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-tien-2-il)tioetil]piperidin-4-octena kiselina.
Postupkom analognim prethodnim primjerima, pripravljena je 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2-tien-2-il)tioetil] piperidin-4-octena kiselina.
1H NMR spektar (300 MHz, (CD3)2SO-d6, S u ppm) : od 1.30 do 1.70 (mt: 8H); 2.14 (s: 2H); 2.33 (mt: 4H); od 2.45 do 2.60 (mt: 2H); 2.92 (široko t, J = 7 Hz: 2H); 3.13 (mt: 2H); 3.96 (s: 3H) ; 7.05 (dd, J = 5.5 i 3.5 Hz: 1H); 7.18 (dd, J = 3.5 i l Hz: 1H); 7.39 (d, J = 3 Hz: 1H); 7.44 (dd, J = 9 i 3 Hz: 1H); 7.60 (dd, J = 5.5 i l Hz: 1H); 7.95 (d, J = 9 Hz: 1H); 8.66 (s: 1H).
Primjer 9
{4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-il}metanol.
Postupkom analognim prethodnim primjerima, pripravljen je {4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltio)etil]piperidin-4-il}metanol.
1H NMR spektar (300 MHz, (CD3)2SO-d6, S u ppm): od 1.15 do 1.75 (mt: 14H); 1.95 (mt: 2H); od 2.20 do 2.40 (mt: 4H); 2.44 (mt: 4H); 2.57 (mt: 2H); od 3.05 do 3.25 (mt: 5H); 3.97 (s: 3H); 4.38 (t, J = 5.5 Hz: 1H); 7.38 (d, J = 3 Hz: 1H); 7.45 (dd, J = 9 i 3 Hz: 1H); 7.96 (d, J = 9 Hz: 1H); 8.68 (s: 1H).
Primjer 10
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[(3-fenilpropil)piperidin-4-il]metanol.
Postupkom analognim prethodnim primjerima, pripravljen je 4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[(3-fenilpropil)piperidin-4-il]metanol.
1H NMR spektar (300 MHz, (CD3)2SO-d6, Σ u ppm) : 1.59 (mt: 2H); od 1.65 do 1.95 (mt: 4H); od 2.20 (široko d, J = 13.5 Hz: 2H); 2.86 (mt: 2H); od 3.10 do 3.65 (mt: 8H); 3.99 (s: 3H); 7.19 (široko dd, J = 7.5 i 4.5 Hz: 1H); od 7.35 do 7.50 (mt: 2H); 7.50 (dd, J = 9 i 3 Hz: 1H); 7.71 (određeno t, J = 7.5 i 1.5 Hz: 1H); 8.01 (d, J = 9 Hz: 1H); 8.48 (široko d, J = 4.5 Hz: 1H); 8.74 (s: 1H); 10.70 (multipli: 1H).
Primjer 11
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna kiselina.
Smjesa od 0.4 g etil 4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilata u 5 cm3 vodene otopine 5 N klorovodične kiseline i 3 cm3 dioksana održavana je na temperaturi od 100°C uz miješanje u inertnoj atmosferi tijekom 20 sati. Nakon hlađenja na 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Smjesa je filtrirana, a zatim kromatografirana, pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 40-63 μ; promjer 1.5 cm; masa 55 g), eluiranjem sa smjesom kloroform/metanol/vodena otopina amonijaka (12/3/0.5 volumena), te sakupljanjem 15-cm3 frakcija. Frakcije 5 do 12 su kombinirane, a potom koncentrirane do isušenja prema prethodno navedenim uvjetima. Dobiveno je 0.26 g 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilne kiseline u obliku bijele kristalne krute tvari točke taljenja 180°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.31 (vrlo široko t), J = 13 Hz: 2H); od 1.50 do 1.70 (mt: 4H); od 1.85 do 2.05 (mt: 4H); 2.45 (široko t, J = 7 Hz: 2H); 2.60 (široko d, J = 11 Hz: 2H); 2.91 (široko t, J = 7 Hz: 2H); 3.04 (jako široko t, J = 6 Hz: 2H); 3.96 (s: 3H); 7.04 (dd, J = 5 i 3.5 Hz: 1H); 7.17 (dd, J = 3.5 i l Hz: 1H); 7.35 (d, J = 2.5 Hz: 1H); 7.40 (dd, J = 9 i 2.5 Hz: 1H); 7.60 (dd, J = 5 i l Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.70 (široko s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilat
Smjesa 0.8 g etilnog 4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.6 g 2-(2-bromoetiltio)tiofena i 1.5 g kalijeva karbonata u 10 cm3 acetonitrila je zagrijavana tijekom 18 sati na temperaturi od 80°C, uz miješanje u inertnoj atmosferi. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen s diklorometanom i vodom. Organska faza je isprana vodom i zasićenom otopinom natrijeva klorida, isušena magenzijevim sulfatom, filtrirana i koncentrirana do isušenja pod prethodno navedenim uvjetima. Ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 70-200 μ; promjer 3 cm; masa 50 g), eluiran sa smjesom etilni acetat/petrolejski eter (40-65°C) (75/25 volumena) i sakupljene su 30-cm3 frakcije. Frakcije 3 do 5 su kombinirane, a zatim koncentrirane do isušenja pod gore navedenim uvjetima. Dobiveno je 0.7 g 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilata u obliku gustog bezbojnog ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 0.99 (t, J = 7 Hz: 3H); 1.34 (vrlo široko t, J = 12 Hz: 2H); od 1.45 do 1.65 (mt: 4H); od 1.85 do 2.00 (mt: 4H); 2.44 (široko t, J = 7 Hz: 2H); 2.59 (široko d, J = 11.5 Hz: 2H); 2.89 (široko t, J = 7 Hz: 2H); 3.03 (jako široko t, J = 6.5 Hz: 2H); 3.94 (q, J = 7 Hz: 2H); 7.02 (dd, J = 5 i 3.5 Hz: 1H); 7.16 (dd, J = 3.5 i l Hz: 1H); 7.32 (d, J = 2.5 Hz: 1H); 7.39 (dd, J = 9 i 2.5 Hz: 1H); 7.58 (dd, J = 5 i l Hz: 1H); 7.96 (d, J = 9 Hz: 1H); 8.69 (široko s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilat
Dodano je 2 cm3 trifluorooctene kiseline, uz miješanje u inertnoj atmosferi, na temperaturi od 5°C, u otopinu od 0.5 g etilnog 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(terc-butiloksikarbonil)piperidin-4-karboksilata u 10 cm3 diklorometana. Nakon 45 minuta, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Ostatak je obrađen u dietilnom eteru i ispran zasićenom otopinom kalijeva bikarbonata, a zatim zasićenom otopinom kalijeva karbonata. Organska faza je isprana dva puta sa 5 cm3 vode, a zatim sa zasićenom otopinom natrijeva klorida, isušena na magnezijevom sulfatu, filtrirana i koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 0.26 g etilnog 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata u obliku gustog ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm): 1.02 (t, J = 7 Hz: 3H); 1.28 (mt: 2H); od 1.45 do 1.65 (mt: 4H); od 1.45 do 1.70 (mt: 4H); 1.90 (široko d, J = 13.5 Hz: 2H); 2.46 (široko t, J = 12 Hz: 2H); 2.79 (d mt, J - 12 Hz: 2H); 3.06 (široko t, J = 6 Hz: 2H); 3.95 (s: 3H); 3.98 (q, J = 7 Hz: 2H); 7.35 (d, J = 2.5 Hz: 1H); 7.40 (dd, J = 9 i 2.5 Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.70 (d, J = l Hz: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(terc-butiloksikarbonil)piperidin-4-karboksilat
1.4 g etil 4-alil-1-(terc-butiloksikarbonil)piperidin-4-karboksilata je ohlađeno na temperaturu od -30°C i dodano je 11 cm3 0.5 M otopine 9-borabiciklo[3.3.1]nonana u tetrahidrofuranu, uz miješanje u inertnoj atmosferi. Nakon dodavanja, temperatura smjese je vraćena na približno 20°C. Dobivena otopina je miješana tijekom daljnja 4 sata, potom je dodano 0.09 g paladijeva difenilfosfinoferocen klorida, 1.4 g 4-jodo-3-fluoro-6-metoksikinolina i 2.5 g tribazičnog kalijeva fosfata. Po završetku miješanja od 16 sati na temperaturi od 60°C, reakcijska smjesa je ohlađena na 20°C, a zatim koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen etilnim acetatom i vodom, faze su odvojene taloženjem, a organska faza je isušena na magnezijevom sulfatu, filtrirana i koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom, pod atmosferskim tlakom, na stupcu silikagela (veličine čestice 70-200 μ; promjer 4.5 cm; masa 125 g), eluiran sa smjesom diklorometan/etilni acetat (98/2 volumena) i sakupljene su 20-cm3 frakcije. Frakcije 98 do 170 su kombinirane, a zatim koncentrirane do isušenja pod gore navedenim uvjetima. Dobiveno je 1.5 g etilnog 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(terc-butiloksikarbonil)piperidin-4-karboksilata u obliku gustog smeđeg ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.02 (t, J = 7 Hz: 3H); 1.30 (mt: 2H); 1.39 (s: 9H); od 1.45 do 1.70 (mt: 4H); 1.92 (široko d, J = 13.5 Hz: 2H); 2.81 (mt: 2H); 3.05 (široko t, J = 6.5 Hz: 2H); 3.69 (široko d, J = 13.5 Hz: 2H); 3.95 (s: 3H); 4.00 (q, J = 7 Hz: 2H); 7.34 (d, J = 2.5 Hz: 1H); 7.40 (dd, J = 9 i 2.5 Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.70 (d, J = 1 Hz: 1H).
4-Jodo-3-fluoro-6-metoksikinolin
1.8 cm3 diizopropilamina u 80 cm3 tetrahidrofurana ohlađeno je na temperaturu od -75°C i dodano je 7.7 cm3 1.6 M otopine butil litija u heksanu, uz miješanje u inertnoj atmosferi. Nakon miješanja tijekom 20 minuta na temperaturi od -75°C, dodana je otopina 2.2 g 3-fluoro-6-metoksikinolina u 20 cm3 tetrahidrofurana. Dobivena otopina je miješana tijekom daljnja 4 sata, zatim je dodana otopina 3.3 g dvostruko sublimiranog joda u 10 cm3 tetrahidrofurana. Nakon miješanja tijekom 2 sata na temperaturi od 20°C, reakcijska smjesa je hidrolizirana sa 200 cm3 smjese 90/10 tetrahidrofuran/voda, a zatim 100 cm3 zasićene otopine natrijeva klorida i 150 cm3 etilnog acetata. Smjesa je isprana 3 puta sa 80 cm3 zasićene otopine natrijeva klorida, isušena na magnezijevom sulfatu, filtrirana i koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom, pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 70-200 μ; promjer 5 cm; visina 35 cm), eluiranjem sa smjesom 90/10 petrolejski eter/etilni acetat. Frakcije 66 do 95 su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveno je 0.9 g 4-jodo-3-fluoro-6-metoksikinolina u obliku krem obojene krute tvari.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 4.00 (s: 3H); 7.31 (d, J = 2.5 Hz: 1H); 7.47 (dd, J = 9 i 2.5 Hz: 1H); 8.01 (d, J = 9 Hz: 1H); 8.64 (s: 1H).
3-Fluoro-6-metoksikinolin
Smjesa od 1.35 g 4-kloro-3-fluoro-6-metoksikinolina, 1.1 cm3 trietilamina i 100 mg paladija-na-ugljenu u 23 cm3 metanola, miješana je na temperaturi od 20°C pod tlakom vodika od 2 bara tijekom 18 sati. Reakcijska smjesa je filtrirana i koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 70-200 μ; promjer 3 cm; masa 40 g), eluiranjem sa diklorometanom/etilnim acetatom (95/5 volumena). Frakcije koje sadrže produkt su kombinirane, a zatim koncentrirane do isušenja u skladu s gore navedenim uvjetima. Dobiven je l g 3-fluoro-6-metoksikinolina.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 3.92 (s: 3H); 7.40 (mt: 2H); 8.07 (d, J = 9 Hz: 1H); 8.04 (dd, J = 10 i 3 Hz: 1H); 8.77 (d, J = 3 Hz: 1H).
4-Kloro-3-fluoro-6-metoksikinolin
1.3 cm3 diizopropilamina u 50 cm3 tetrahidrofurana je ohlađeno na temperaturu od -75°C i dodano je 5.8 cm3 1.6 M otopine butil litija u heksanu, uz miješanje u inertnoj atmosferi. Nakon miješanja tijekom 20 minuta na temperaturi od -75°C, dodana je otopina od 1.2 g 4-kloro-6-metoksikinolina u 20 cm3 tetrahidrofurana. Dobivena otopina je miješana tijekom daljnja 4 sata, potom je dodana otopina od 2.9 g N-fluorobenzen sulfonimida u 10 cm3 tetrahidrofurana. Nakon miješanja tijekom 2 sata na temperaturi od 40°C, reakcijska smjesa je hidrolizirana sa 200 cm3 smjese omjera 90/10 tetrahidrofuran/voda, a zatim sa 100 cm3 zasićene otopine natrijeva klorida i 150 cm3 etilnog acetata. Smjesa je isprana 3 puta sa 80 cm3 zasićene otopine natrijeva klorida, te isušena na megnezijevom sulfatu, filtrirana i koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom, pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 70-200 μ; promjer 4 cm; masa 100 g), eluiranjem sa diklorometanom. Frakcije koje sadržavaju produkt su kombinirane, a potom koncentrirane do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveno je 0.4 g 4-kloro-3-fluoro-6-metoksikinolina.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 4.01 (s: 3H); 7.43 (d, J = 2.5 Hz: 1H); 7.52 (dd, J = 9 i 2.5 Hz: 1H); 8.07 (d, J = 9 Hz: 1H); 8.91 (d, J = l Hz: 1H).
4-Kloro-6-metoksikinolin
Smjesa 12 g 4-hidroksi-6-metoksikinolina u 50 cm3 [lakuna] oksiklorida [lakuna] inertna atmosfera, tijekom 2 sata. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40 °C, a zatim hidrolizirana ledom i dovedena na vrijednost pH = 10 primjenom 5 N otopine natrijeva hidroksida. Smjesa je ekstrahirana etilnim acetatom, isušena na magnezij evom sulfatu, filtrirana i koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je kromatografiran, pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 70-200 μ), eluiranjem sa smjesom diklorometan/metanol (85/15 volumena). Frakcije koje sadržavaju produkt su kombinirane, a potom koncentrirane do isušenja pod gore navedenim uvjetima. Dobiveno je 12 g 4-kloro-6-metoksikinolina u obliku krute bijele tvari točke taljenja 82°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm): 3.958 (s: 3H) ; 7.45 (d, J = 2.5 Hz: 1H); 7.53 (dd, J = 9 i 2.5 Hz: 1H) ; 7.76 (d, J = 4.5 Hz: 1H); 8.04 (d, J = 9 Hz: 1H); 8.70 (d, J = 4.5 Hz: 1H).
Etil 4-alil-1-(terc-butiloksikarbonil)-piperidin-4-karboksilat je pripravljen u Primjeru 1.
4-Hidroksi-6-metoksikinolin je pripravljen kao što je opisano u Primjeru 1.
Primjer 12
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluoro-6-fenoksi) etil]piperidin-4-karboksilna kiselina
Smjesa 0.4 g etilnog 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluoro-6-fenoksi)etil]piperidin-4-karboksilata u 6 cm3 vodene otopine 5N klorovodične kiseline i 10 cm3 dioksana je održavana na temperaturi od 100°C, uz miješanje u inertnoj atmosferi, tijekom 20 sati. Nakon hlađenja na 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je kromatografiran, pod atmosferskim tlakom, na stupcu silikagela (veličina čestica 70-200 μ; promjer 1.5 cm; masa 50 g), eluiranjem sa smjesom kloroform/metanol/vodena otopina amonijaka (12/3/0.5 volumena) i sakupljanjem 15-cm3 frakcija. Frakcije 10 do 15 su kombinirane, a potom koncentrirane do isušenja u skladu s gore navedenim uvjetima. Dobiveno je 0.2 g 4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluoro-6-fenoksi)etil]piperidin-4-karboksilne kiseline u obliku bijele krute tvari točke taljenja 175°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.33 (vrlo široko t, J = 13 Hz: 2H); od 1.50 do 1.70 (mt: 4H); 1.95 (široko d, J = 13 Hz: 2H); 2.05 (široko t, J = 11.5 Hz: 2H) ; 2.60 (t, J = 6 Hz: 2H); 2.69 (široko d, J = 11.5 Hz: 2H); 3.04 (mt: 2H); 3.96 (s: 3H); 4.06 (t, J = 6 Hz: 2H); od 6.65 do 6.85 (mt: 3H); 7.34 (d, J = 2.5 Hz: 1H); 7.39 (dd, J = 9 i 2.5 Hz: 1H); 7.96 (d, J = 9 Hz: 1H); 8.69 (široko s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluoro-6-fenoksi)etil]piperidin-4-karboksilat
Smjesa od 0.4 g etilnog 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.3 g 1-(2-bromoetoksi)-3,5-difluorobenzena, 0.18 g kalijeva jodida i 0.74 g kalijeva karbonata u 10 cm3 acetonitrila je zagrijavana tijekom 18 sati na temperaturi od 75°C, uz miješanje u inertnoj atmosferi. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen u etilnom acetatu i vodi. Organska faza je isprana vodom i zasićenom otopinom natrijeva klorida, isušena na magnezijevom sulfatu, filtrirana i koncentrirana do isušenja pod gore navedenim uvjetima. Ostatak je pročišćen kromatografijom, pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 70-200 μ; promjer 1.5 cm, masa 35 g), eluiranjem s diklorometanom. Frakcije 7 do 11 su kombinirane, a potom koncentrirane do isušenja u skladu sa gore navedenim uvjetima. Dobiveno je 0.4 g etilnog 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluoro-6-fenoksi)etil]piperidin-4-karboksilata u obliku gustog bezbojnog ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.00 (t, J = 7 Hz: 3H); 1.38 (vrlo široko t, J = 12 Hz: 2H); od 1.45 do 1.70 (mt: 4H); od 1.90 do 2.10 (mt: 4H); 2.60 (t, J = 6 Hz: 2H); 2.69 (vrlo široko d, J = 12 Hz: 2H); 3.05 (vrlo široko t, J = 6.5 Hz: 2H); 3.95 (s: 3H); 3.98 (q, J = 7 Hz: 2H); 4.06 (t, J = 6 Hz: 2H); od 6.65 do 6.85 (mt: 3H); 7.34 (d, J = 2.5 Hz: 1H); 7.40 (dd, J = 9 i 2.5 Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.70 (široko s: 1H).
Etil 4-alil-1-(terc-butiloksikarbonil)-piperidin-4-karboksilat je pripravljen u Primjeru 1.
1-(2-Bromoetoksi)-3,5-difluorobenzen se može dobiti primjenom postupka opisanog u Primjeru 16.
Primjer 13
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluoro-6-fenoksi)etil]piperidin-4-karboksilna kiselina dihidroklorid
Smjesa od l g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluoro-6-fenoksi)etil]piperidin-4-karboksilata u 50 cm3 vodene otopine 5N klorovodične kiseline je održavana na temperaturi od 100°C, uz miješanje tijekom 20 sati. Nakon hlađenja na 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen u 50 cm3 acetona, filtriran, ispran sa 3 puta po 15 cm3 [lakuna] i potom isušen u sušilici pod sniženim tlakom (0.1 kPa) na temperaturi od 40°C. Dobiveno je 0.88 g 4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluoro-6-fenoksi)etil]piperidin-4-karboksilna kiselina dihidroklorida u obliku bijele krute tvari točke taljenja 170°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.45 do 2.30 (mt: 8H); od 2.85 do 3.70 (mt: 8H); 3.97 (s: 3H); 4.50 (mt: 2H); 7.15 (mt: 2H); 7.40 (d, J = 3 Hz: 1H); 7.46 (dd, J = 9 i 3 Hz: 1H); 7.46 (dd, J = 9 i 3 Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.69 (s: 1H); 10.07 (nedefinirani vršak: 1H); od 12.50 do 13.10 (široki nedefinirani vršak: 1H).
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluoro-6-fenoksi)etil]piperidin-4-karboksilata
Smjesa od 1.4 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilat hidroklorida, 0.9 g 1-(2-bromoetoksi)-2,3,5-trifluorobenzena, 0.6 g kalijeva jodida i 2 g kalijeva karbonata u 100 cm3 acetonitrila je zagrijavana tijekom 18 sati na temperaturi od 75°C uz miješanje u inertnoj atmosferi. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je filtrirana i isprana sa 3 puta po 30 cm3 acetonitrila. Filtrat je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 20-45 μ; promjer 3 cm; visina 27 cm), eluiran sa etilnim acetatom i sakupljene su 50-cm3 frakcije. Frakcije 9 do 23 su kombinirane, a zatim koncentrirane do isušenja prema prethodno navedenim uvjetima. Dobiveno je 1.27 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2F3,5-trifluoro-6-fenoksi)etil]piperidin-4-karboksilata u obliku gustog žutog ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.30 do 1.60 (mt: 4H); 1.72 (mt: 2H); od 1.95 do 2.15 (mt: 4H); 2.64 (t, J = 5.5 Hz: 2H); 2.71 (d - nedefinirani vršak, J = 12 Hz: 2H); 3.13 (široko t, J = 7.5 Hz: 2H); 3.93 (s: 3H); 4.16 (t, J = 5.5 Hz: 2H); 5.04 (s: 2H); od 6.95 do 7.15 (mt: 2H); od 7.20 do 7.30 (mt: 5H); 7.34 (d, J = 3 Hz: 1H); 7.45 (dd, J = 9 i 3 Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.67 (s: 1H).
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilat hidroklorid
Smjesa od 17.4 g benzil l-terc-butiloksikarbonil-4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata u 75 cm3 5N klorovodične kiseline otopljene u dioksanu i 200 cm3 dioksana miješana je na temperaturi od 20 °C, uz miješanje tijekom 20 sati. U reakcijsku smjesu je dodano 200 cm3 dietilnog etera. Nastali precipitat je filtracijom odvojen do nastanka 14.26 g benzil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilat hidroklorida.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm): 1.49 (mt: 2H); od 1.65 do 1.85 (mt: 4H); 2.11 (d - nedefinirani vršak, J = 14 Hz: 2H); 2.78 (mt: 2H); od 3.10 do 3.25 (mt: 2H); 3.20 (široko t, J = 7.5 Hz: 2H); 3.96 (s: 3H); 5.09 (s: 2H); 7.28 (mt: 5H); 7.43 (d, J = 3 Hz: 1H); 7.53 (dd, J = 9 i 3 Hz); 8.06 (d, J = 9 Hz: 1H); 8.80 (s: 1H); od 9.05 do 9.30 (nedefinirani vršak: 2H).
1-(2-Bromoetoksi)-2,3,4-trifluorobenzen
Smjesa od 11.4 g 2,3,4-trifluorofenola, 40.5 cm3 1,2-dibromoetana i 15.3 g kalijeva karbonata u 200 cm3 acetonitrila je zagrijavana tijekom 18 sati na temperaturi od 75°C, uz miješanje u inertnoj atmosferi. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je filtrirana i isprana sa 4 puta po 50 cm3 acetonitrila. Filtrat je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen sa 150 cm3 petrolejskog etera (40-65°C), filtriran i ispran sa 3 puta po 30 cm3 petrolejskog etera (40-65°C). Filtrat je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 20-45 μ; promjer 5 cm; visina 33 cm), eluiran petrolejskim eterom (40-65°C) i sakupljene su 100 cm3 frakcije. Frakcije 28 do 63 su kombinirane, a potom koncentrirane do isušenja pod gore navedenim uvjetima. Dobiveno je 16.15 g 1-(2-bromoetoksi)-2,3,5-trifluorobenzena u obliku gustog, bezbojnog ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 3.83 (široko t, J = 5.5 Hz: 2H); 4.45 (široko t, J = 5.5 Hz: 2H) ; od 7.00 do 7.15 (mt: 2H).
Benzil 4-alil-1-(terc-butiloksikarbonil)-piperidin-4-karboksilat je pripravljen u Primjeru 1.
Primjer 14
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,5-difluoro-6-feniltio)etil]piperidin-4-karboksilna kiselina
Smjesa od 1.3 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,5-difluoro-6-[lakuna]piperidin-4-karboksilata u 15 cm3 vodene otopine 5N klorovodične kiseline i 15 cm3 dioksana je održavana na temperaturi od 100°C, uz miješanje u inertnoj atmosferi tijekom 20 sati. Nakon hlađenja na 20°C, reakcijska smjesa je uparena pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen četiri puta u toluenu, uz uparavenje između svakog ispiranja. Dobiveno ulje je obrađeno u smjesi kloroform/metanol/vodena otopina amonijaka (12/3/0.5 volumena), faze su odvojene taloženjem, a organska faza je isprana vodom i potom ostavljena da kristalizira tijekom 20 sati. Dobivena kruta tvar je filtracijom odvojena, a potom isušena u sušilici pod sniženim tlakom (0.1 kPa) na temperaturi od 40°C. Dobiveno je 0.6 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,5-difluoro-6-pentiltio)etil]piperidin-4-karboksilne kiseline u obliku bijele kristalne krute tvari točke taljenja 205°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.39 (nedefinirani vršak: 2H); 1.55 (mt: 2H); 1.70 (mt: 2H); od 1.90 do 2.20 (mt: 4H); od 2.40 do 2.85 (široki nedefinirani vršak: 4H)/ od 3.05 do 3.25 (mt: 2H); 3.17 (široki t, J = 7.5 Hz: 2H); 3.96 (s: 3H); 7.07 (mt: 1H); 7.26 (mt: 1H); 7.33 (mt: 1H); 7.38 (d, J = 2.5 Hz: 1H); 7.46 (dd, J = 9 i 2.5 Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.68 (s: 1H); od 12.00 do 12.50 (nedefinirani vršak: 1H).
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,5-difluoro-6-feniltio)etil]piperidin-4-karboksilat
Smjesa od 1.4 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.9 g 1-(2-bromoetiltio)-2,5-difluorobenzena, 0.6 g kalijeva jodida i 2 g kalijeva karbonata u 100 cm3 acetonitrila je zagrijavana tijekom 18 sati na temperaturi od 75°C uz miješanje u inertnoj atmosferi. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen vodom i ekstrahiran etilnim acetatom. Organska faza je isprana zasićenom otopinom natrijeva klorida, isušena na magnezijevom sulfatu, a potom koncentrirana do isušenja kao što je prethodno navedeno. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 70-200 μ; promjer 2.5 cm; masa 50 g), eluiran sa smjesom etilnog acetata i diklorometana (05/95 volumena) i sakupljene su 15-cm3 frakcije. Frakcije 21 do 100 su kombinirane, a zatim koncentrirane do isušenja prema prethodno navedenim uvjetima. Dobiveno je 1.35 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,5-difluoro-6-fenoiltio)etil]piperidin-4-karboksilata u obliku krute bijele tvari točke taljenja 95°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.30 do 1.60 (mt: 4H); 1.71 (mt: 2H); od 1.85 do 2.05 (mt: 4H); od 2.40 do 2.60 (mt: 2H); 2.66 (d-nedefinirani vršak, J = 12 Hz: 2H); od 3.05 do 3.20 (mt: 2H); 3.11 (široki t, J = 7.5 Hz: 2H); 3.92 (s: 3H); 5.03 (S: 2H); 7.04 (mt: 1H); od 7.15 do 7.35 (mt: 7H); 7.35 (d, J = 3 Hz: 1H); 7.44 (dd, J = 9 i 3 Hz: 1H); 7.95 (d, J = 9 Hz: 1H); 8.66 (s: 1H).
1-(2-Bromoeiltio)-2,5-difluorobenzen
Smjesa od 5.8 g S(2,5)-difluorofeil-dimetil tiokarbamata u 80 cm3 10% otopine kalijeva hidroksida u metanolu je zagrijavana tijekom l sata na temperaturi od 100°C, uz miješanje u inertnoj atmosferi. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen vodom, ekstrahiran dietilnim eterom, a potom zakiseljen s 40 cm3 5N klorovodične kiseline. Vodena faza je ekstrahirana s dva puta po 30 cm3 dietilnog etera. Organske faze su kombinirane, isprane zasićenom otopinom natrijeva klorida, isušene na natrijevom sulfatu, filtrirane, a zatim koncentrirane do isušenja kao što je prethodno navedeno. Dobiveni ostatak je obrađen sa 30 cm3 1,2-dibromoetana i 0.5 g alkivota 336, a potom je dodano 20 cm3 hladne otopine natrijeva hidroksida. Dobivena otopina je miješana tijekom daljnjih 18 sati na temperaturi od 20°C, a zatim isprana s dva puta po 15 cm3 vode. Organske faze su kombinirane, isprane zasićenom ostopinom natrijeva klorida, isušene na natrijevom sulfatu, filtrirane i koncentrirane do isušenja kao što je prethodno navedeno. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 70-200 μ; promjer 2.5 cm; masa 75 g), eluiran petrolejskim eterom i sakupljene su 50-cm3 frakcije. Frakcije 4 do 13 su kombinirane, a potom koncentrirane do isušenja pod gore navedenim uvjetima. Dobiveno je 4.4 g 1-(2-bromoeiltio)-2,5-difluorobenzena u obliku bezbojnog, tekućeg ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 3.50 (mt: 2H); 3.66 (mt: 2H); 7.15 (mt: 1H); 7.32 (udvostručeni triplet, J = 9 i 4.5 Hz: 1H); 7.42 (ddd, J = 9-6.5 i 3 Hz: 1H).
Dimetil S-(2,5)-difluorofeniltiokarbamat
2 g dimetil O-(2,5)-difluorofeniltiokarbamata je zagrijavano na temperaturi od 235°C tijekom 40 minuta. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 70-200 μ; promjer 3 cm; masa: 25 g), eluiran smjesom petrolejskog etera i diklorometana (50/50 omjer volumena) i sakupljanjem 15-cm3 frakcija. Frakcije 6 do 11 su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 1.25 g dimetil S-(2,5)-difluorofeniltiokarbamata u obliku bijele krute tvari točke taljenja 96°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm): 2.96 (nedefinirani vršak: 3H); 3.08 (nedefinirani vršak: 3H); od 7.35 do 7.50 (mt: 3H).
Dimetil O-(2,5)-difluorofeniltiokarbamat
14.1 g dimetiltiokarbamatnog klorida i 13 g 1,4-diaza[2.2.2]triciklooktana je dodano uz miješanje otopini od 7.5 g 2,5-difluorofenolla u 120 cm3 dimetilformamida. Nakon miješanja tijekom l sata na temperaturi od 20°C, reakcijska smjesa je obrađena s l dm3 vode i 100 cm3 suhe koncentrirane klorovodične kiseline, te ekstrahirana sa 400 cm3 dietilnog etera. Organska faza je isušena na natrijevom sulfatu, filtrirana i zatim koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 70-200 μ; promjer 10 cm; masa 400 g), eluiranjem sa smjesom petrolejskog etera i diklorometana (50/50 volumena). Frakcije koje sadrže očekivani produkt su kombinirane, a potom koncentrirane do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Dobiveno je 12.4 g dimetil O-(2,5)-difluorofeniltiokarbamata u obliku krute tvari točke taljenja 62°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 3.53 (s: 3H)/ 3.40 (s: 3H); od 7.15 do 7.30 (mt: 2H); 7.42 (udvostručeni triplet, J = 9.5 i 5.5 Hz: 1H).
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilat hidroklorid je pripravljen u Primjeru 13.
Primjer 15
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,6-difluorofenoksi)etil]piperidin-4-karboksilna kiselina dihidroklorid
Smjesa od l g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,6-difluorofenoksi)-etil]piperidin-4-karboksilata u 50 cm3 vodene otopine 5N klorovodične kiseline je održavana na temperaturi od 100°C, uz miješanje u inertnoj atmosferi tijekom 20 sati. Nakon hlađenja na 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen sa 50 cm3 acetona, a potom miješan tijekom l sata na temperaturi od 20°C. Smjesa je filtrirana, isprana 3 puta sa 15 cm3 acetona i zatim isušena u sušilici pod sniženim tlakom (0.1 kPa) na temperaturi od 40°C. Dobiveno je 0.86 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,6-difluorofenoksi)-etil]piperidin-4-karboksilne kiseline dihidroklorida u obliku bijele krute tvari točke taljenja 218°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.59 (mt: 2H); 1.75 (mt: 2H); 1.82 (vrlo široki t, J = 14 Hz: 2H); 2.22 (široki d, J = 14 Hz: 2H); 2.98 (mt: 2H); 3.22 (široki t, J = 7.5 Hz: 2H); od 3.45 do 3.70 (mt: 4H); 3.98 (s: 3H); 4.51 (t, J = 5 Hz: 2H); od 7.15 do 7.25 (mt: 3H); 7.42 (d, J = 3 Hz: 1H); 7.48 (dd, J = 9 i 3 Hz: 1H); 7.99 (d, J = 9 Hz: 1H); 8.72 (s: 1H); 10.66 (nedefinirani vršak: 1H).
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,6-difluorofenoksi)etil]piperidin-4-karboksilat
Smjesa od 1.4 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.82 g 1-(2-bromoetoksi)-2,6-difluorobenzena, 0.6 g kalijeva jodida i 2 g kalijeva karbonata u 100 cm3 acetonitrila je zagrijavana tijekom 18 sati na temperaturi od 75°C uz miješanje u inertnoj atmosferi. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je filtrirana i isprana sa 3 puta po 30 cm3 acetonitrila. Filtrat je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 20-45 μ; promjer 3 cm; visina 27 cm), eluiran sa etilnim acetatom i sakupljene su 50-cm3 frakcije. Frakcije 7 do 17 su kombinirane, a zatim koncentrirane do isušenja prema prethodno navedenim uvjetima. Dobiveno je 1.65 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,6-difluorofenoksi)etil]piperidin-4-karboksilata u obliku gustog žutog ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm): od 1.25 do 1.55 (mt: 4H); 1.70 (mt: 2H); od 1.90 do 2.10 (mt: 4H); 2.59 (t, J = 6 Hz: 2H); 2.66 (d - nedefinirani vršak, J = 12 Hz: 2H); 3.13 (široko t, J = 7.5 Hz: 2H); 3.93 (s: 3H); 4.14 (t, J = 6 Hz: 2H); 5.03 (s: 2H); od 7.05 do 7.20 (mt: 3H); 7.35 (d, J = 3 Hz: 1H); 7.46 (dd, J = 9 i 3 Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.67 (s: 1H).
1-(2-Bromoetoksi)-2,6-difluorobenzen
Smjesa od 10 g 2,6-difluorofenola, 40.5 cm3 1,2-dibromoetana i 15.3 g kalijeva karbonata u 300 cm3acetonitrila je zagrijavana tijekom 18 sati na temperaturi od 75°C, uz miješanje u inertnoj atmosferi. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je filtrirana i isprana sa 3 puta po 30 cm3 acetonitrila. Filtrat je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen sa 200 cm3petrolejskog etera (40-65°C), filtriran i ispran sa 3 puta po 30 cm3 petrolejskog etera (40-65°C). Filtrat je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 20-45 μ; promjer 7 cm; visina 28 cm), eluiran petrolejskim eterom (40-65°C) i sakupljene su 100 cm3 frakcije. Frakcije 22 do 58 su kombinirane, a potom koncentrirane do isušenja pod gore navedenim uvjetima. Dobiveno je 14.5 g 1-(2-bromoetoksi)-2,6-difluorobenzena u obliku gustog, bezbojnog ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 3.76 (široko t, J = 6 Hz: 2H); 4.42 (široko t, J = 6 Hz: 2H); od 7.10 do 7.25 (mt: 3H).
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilatni hidroklorid je pripravljen u Primjeru 13.
Primjer 16
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,5-difluorofenoksi)etil]piperidin-4-karboksilna kiselina dihidroklorid
Smjesa od l g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,5-difluorofenoksi)etil]piperidin-4-karboksilata u 50 cm3 5N klorovodične kiseline je održavana na temperaturi od 100°C, uz miješanje u inertnoj atmosferi tijekom 20 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen sa 50 cm3 acetona, a potom miješan tijekom l sata na temperaturi od 20°C. Smjesa je filtrirana, isprana 3 puta sa 15 cm3 acetona i zatim isušena u sušilici pod sniženim tlakom (0.1 kPa) na temperaturi od 40°C. Dobiveno je 0.8 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,5-difluorofenoksi)-etil]piperidin-4-karboksilne kiseline dihidroklorida u obliku bijele krute tvari točke taljenja 180°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.58 (mt: 2H)/ 1.72 (mt: 2H); 1.84 (vrlo široki t, J = 14 Hz: 2H); 2.19 (široki d, J = 14 Hz: 2H); 2.95 (mt: 2H); 3.22 (široki t, J = 7.5 Hz: 2H); 3.53 (mt: 4H); 3.98 (s: 3H); 4.52 (t, J= 5 Hz: 2H); 6.84 (mt: 1H); 7.22 (ddd, J = 9 - 7 i 3 Hz: 1H); e7.30 (ddd, J = 10.5 - 9 i 4.5 Hz: 1H); 7.42 (d, J = 2.5 Hz: 1H); 7,48 (dd, J = 9 i 2.5 Hz: 1H); 8.00 (d, J = 9 Hz: 1H); 8.74 (s: 1H); 10.97 (nedefinirani vršak: 1H).
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,5-difluorofenoksi)etil]piperidin-4-karboksilat
Smjesa od 1.4 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilatnog hidroklorida, 0.82 g 1-(2-bromoetoksi)-2,5-difluorobenzena, 0.6 g kalijeva jodida i 2 g kalijeva karbonata u 100 cm3 acetonitrila je zagrijavana tijekom 18 sati na temperaturi od 75°C uz miješanje u inertnoj atmosferi. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je filtrirana i isprana sa 3 puta po 30 cm3 acetonitrila. Filtrat je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 20-45 μ; promjer 2.4 cm; visina 26 cm), eluiran sa etilnim acetatom i sakupljene su 30-cm3 frakcije. Frakcije 7 do 14 su kombinirane, a zatim koncentrirane do isušenja prema prethodno navedenim uvjetima. Dobiveno je 1.6 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,5-difluorofenoksi)etil]piperidin-4-karboksilata u obliku gustog žutog ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.35 do 1.60 (mt: 4H); 1.73 (mt: 2H); od 1.95 do 2.15 (mt: 4H); 2.63 (t, J = 5.5 Hz: 2H); 2.72 (d - nedefinirani vršak, J = 12 Hz: 2H); 3.14 (široko t, J = 7.5 Hz: 2H); 3.92 (s: 3H); 4.12 (t, J = 5.5 Hz: 2H); 5.04 (s: 2H); 6.75 (trostruka trojka, J = 9 i 3 Hz: 1H); 7.13 (ddd, J = 10.5 - 7.5 i 3 Hz: 1H); od 7.20 do 7.30 (mt: 6H); 7.34 (d, J = 3 Hz: 1H); 7.45 (dd, J = 9 i 3 Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.67 (s: 1H).
1-(2-Bromoetoksi)-2,5-difluorobenzen
Smjesa od 10 g 2,5-difluorofenola, 40.5 cm3 1,2-dibromoetana i 15.3 g kalijeva karbonata u 200 cm3 acetonitrila je zagrijavana tijekom 18 sati na temperaturi od 75°C, uz miješanje u inertnoj atmosferi. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je filtrirana i isprana sa 4 puta po 50 cm3 acetonitrila. Filtrat je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen sa 150 cm3petrolejskog etera (40-65°C), filtriran i ispran sa 3 puta po 30 cm3 petrolejskog etera (40-65°C). Filtrat je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 20-45 μ; promjer 7 cm; visina 49 cm), eluiran petrolejskim eterom (40-65°C) i sakupljene su 100 cm3 frakcije. Frakcije 29 do 88 su kombinirane, a potom koncentrirane do isušenja pod gore navedenim uvjetima. Dobiveno je 13.5 g 1-(2-bromoetoksi)-2,5-difluorobenzena u obliku gustog, bezbojnog ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 3.85 (široko t, J = 6 Hz: 2H); 4.44 (široko t, J = 6 Hz: 2H); 6.82 (mt: 1H); 7.18 (ddd, J = 9 - 7 i 3 Hz: 1H); 7.29 (ddd, J = 11 - 9 i 5 Hz: 1H).
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilatni hidroklorid je pripravljen u Primjeru 13.
Primjer 17
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3-difluorofenoksi)etil]piperidin-4-karboksilna kiselina dihidroklorid
Smjesa od l g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3-difluorofenoksi)etil]piperidin-4-karboksilata u 50 cm3 5N vodene otopine klorovodične kiseline je održavana na temperaturi od 100°C, uz miješanje u inertnoj atmosferi tijekom 20 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen sa 50 cm3 acetona, a potom miješan tijekom l sata na temperaturi od 20°C. Smjesa je filtrirana, isprana sa 3 puta po 15 cm3 acetona i zatim isušena u sušilici pod sniženim tlakom (0.1 kPa) na temperaturi od 40°C. Dobiveno je 0.9 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3-difluorofenoksi)etil]piperidin-4-karboksilne kiseline dihidroklorida u obliku bijele krute tvari točke taljenja 259°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm): od 1.45 do 1.65 (mt: 2H); 1.73 (mt: 2H); 1.81 (vrlo široki t, J = 14 Hz: 2H); 2.20 (široki d, J = 14 Hz: 2H); 2.97 (mt: 2H); 3.22 (široki t, J = 7.5 Hz: 2H); od 3.45 do 3.60 (mt: 4H); 3.98 (s: 3H); 4.54 (t, J = 5 Hz: 2H); 7.04 (mt: 2H); 7.20 (mt: 1H); 7.42 (d, J = 2.5 Hz: 1H); 7,48 (dd, J = 9 i 2.5 Hz: 1H); 7.99 (d, J = 9 Hz: 1H); 8.72 (s: 1H); 10.70 (nedefinirani vršak: 1H); od 12.40 do 13.30 (široki nedefinirani vršak: 1H).
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3-difluorofenoksi)etil]piperidin-4-karboksilat
Smjesa od 1.4 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilatnog hidroklorida, 0.82 g 1-(2-bromoetoksi)-2,3-difluorobenzena, 0.6 g kalijeva jodida i 2 g kalijeva karbonata u 100 cm3 acetonitrila je zagrijavana tijekom 18 sati na temperaturi od 75°C uz miješanje u inertnoj atmosferi. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je filtrirana i isprana sa 3 puta po 30 cm3 acetonitrila. Filtrat je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 20-45 μ; promjer 2.7 cm; visina 32 cm), eluiran sa etilnim acetatom i sakupljene su 30-cm3 frakcije. Frakcije 7 do 21 su kombinirane, a zatim koncentrirane do isušenja prema prethodno navedenim uvjetima. Dobiveno je 1.6 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,3-difluorofenoksi)etil]piperidin-4-karboksilata u obliku gustog žutog ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.35 do 1.55 (mt: 4H); 1.72 (mt: 2H); od 1.95 do 2.15 (mt: 4H); 2.64 (t, J = 6 Hz: 2H); 2.72 (d - nedefinirani vršak, J = 12 Hz: 2H); 3.13 (široko t, J = 7.5 Hz: 2H); 3.93 (s: 3H); 4.15 (t, J = 6 Hz: 2H); 5.04 (s: 2H); od 6.90 do 7.20 (mts: 3H); 7.25 (mt: 5H); 7.35 (d, J = 3 Hz: 1H); 7.46 (dd, J = 9 i 3 Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.67 (s: 1H).
1-(2-Bromoetoksi)-2,3-difluorobenzen
Smjesa od 10 g 2,3-difluorofenola, 40.5 cm3 1,2-dibromoetana i 15.3 g kalijeva karbonata u 200 cm3 acetonitrila je zagrijavana tijekom 48 sati na temperaturi od 75°C, uz miješanje u inertnoj atmosferi. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je filtrirana i isprana sa 6 puta po 30 cm3 acetonitrila. Filtrat je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 20-45 μ; promjer 7 cm; visina 42 cm), eluiran smjesom diklorometana i etilnog acetata (90/10 omjer volumena), te sakupljanjem 100-cm3 frakcija. Frakcije 4 do 10 su kombinirane, a potom koncentrirane do isušenja pod gore navedenim uvjetima. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 20-45 μ; promjer 5 cm; visina 30 cm), eluiran petrolejskim eterom (40-65°C) i sakupljene su 100-cm3 frakcije. Frakcije 34 do 82 su kombinirane, a potom koncentrirane do isušenja pod gore navedenim uvjetima. Dobiveno je 13.6 g 1-(2-bromoetoksi)-2,3-difluorobenzena u obliku bezbojnog, tekućeg ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 3.85 (široko t, J = 6 Hz: 2H); 4.44 (široko t, J = 6 Hz: 2H); 6.82 (mt: 1H); 7.18 (ddd, J = 9 - 7 i 3 Hz: 1H); 7.29 (ddd, J = 11 - 9 i 5 Hz: 1H).
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilatni hidroklorid je pripravljen u Primjeru 13.
Primjer 18
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-(2-tiazol-2-tioetil)piperidin-4-karboksilna kiselina
Smjesa od 0.3 g etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(2-tiazol-2-tioetil)piperidin-4-karboksilata u 6 cm3 5N vodene otopine klorovodične kiseline je održavana na temperaturi od 100°C, uz miješanje u inertnoj atmosferi tijekom 6 sati. Nakon hlađenja i miješanja tijekom 16 sati na temperaturi od 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen sa 10 cm3 dikloroetana koji sadrži 10% metanola, a zatim je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 40-60 μ; promjer 2.5 cm; visina 30 cm), eluiran sa smjesom diklorometan/metanol/vodena otopina amonijaka (89/10/1 omjera volumena). Frakcije 18 do 41 su kombinirane, a potom koncentrirane do isušenja pod prethodno navedenim uvjetima. Dobiveni ostatak je obrađen sa 5 cm3 izopropilnog etera, filtriran i isušen u sušilici pod sniženim tlakom (0.1 kPa) na temperaturi od 40°C. Dobiveno je 0.24 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(2-tiazol-2-tioetil)piperidin-4-karboksilne kiseline u obliku bijele krute tvari točke taljenja 200°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.34 (mt: 2H); 1.55 (mt: 2H); 1.69 (mt: 2H); od 1.85 do 2.15 (mt: 4H); 2.59 (široki t, J = 7 Hz: 2H); 2.67 (d - nedefinirani vršak, J = 12 Hz: 2H); 3.17 (široko t, J = 6 Hz: 2H); od 3.20 do 3.50 (mt: 2H); 3.96 (s: 3H); 7.38 (široko s: 1H); 7.45 (široko dd, J = 9 i 2.5 Hz: 1H); 7.63 (d, J = 3 Hz: 1H); 7.71 (d, J = 3 Hz: 1H); 7.96 (d, J = 9 Hz: 1H); 8.68 (s: 1H); od 11.90 do 12.55 (vrlo široki nedefinirani vršak: 1H).
Etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(2-tiazol-2-tioetil)piperidin-4-karboksilat
0.28 g 2-merkaptotiazola, 0.33 g kalijeva karbonata i 0.39 g kalijeva jodida je dodano u otopinu od 0.9 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(2-kloroetil)piperidin-4-karboksilat u 50 cm3 acetonitrila na temperaturi od 20°C, uz miješanje u inertnoj atmosferi. Nakon zagrijavanja tijekom 20 sati na temperaturi od 80°C, reakcijska smjesa je ohlađena na približno 20°C, filtrirana i koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 50°C. Dobiveni ostatak je pročišćen kromatografijom pod tlakom od 100 kPa dušika, na stupcu silikagela (veličina čestice 40-60 μ; promjer 3.5 cm; visina 35 cm), eluiran sa smjesom diklorometan/metanol (95/0.5 omjer volumena) i sakupljene su 40-cm3 frakcije. Frakcije koje sadržavaju produkt su kombinirane, a zatim pročišćene kromatografijom pod tlakom dušika od 100 kPa, na stupcu silikagela (veličina čestice 40-60 μ; promjer 3.5 cm; visina 3 cm), eluirane sa smjesom etilnog acetata/cikloheksana (75/25 omjer volumena) i sakupljanjem 30-cm3 frakcija. Frakcije 23 do 40 su kombinirane, a zatim koncentrirane do isušenja prema prethodno navedenim uvjetima. Dobiveno je 0.75 g etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(2-tiazol-2-tioetil)piperidin-4-karboksilata.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.05 (t, J = 7 Hz: 3H); 1.38 (mt: 2H); 1.52 (mt: 2H); 1.68 (mt: 2H); od 1.90 do 2.05 (mt: 4H); 2.59 (t, J = 7 Hz: 2H); 2.68 (široko d, J = 12 Hz: 2H); 3.17 (široko t, J = 7.5 Hz: 2H); od 3.25 do 3.40 (mt: 2H); 3.97 (s: 3H); 4.00 (q, J = 7 Hz: 2H); 7.38 (d, J = 2.5 Hz: 1H); 7.46 (dd, J = 9 i 2.5 Hz: 1H); 7.63 (d, J = 3.5 Hz: 1H); 7.71 (d, J = 3.5 Hz: 1H); 7.96 (d, J = 9 Hz: 1H); 8.68 (s: 1H).
Etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(2-kloroetil)piperidin-4-karboksilat
1.21 cm3 tionilnog klorida je dodano otopini od 1.8 g etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(2-hidroksietil)piperidin-4-karboksilata u 40 cm3 diklorometana uz miješanje na temperaturi od 20°C. Nakon miješanja tijekom 48 sati na temperaturi od 20°C, reakcijska smjesa je koncentrirana pod sniženim tlakom (l kPa) na temperaturi od 50°C. Ostatak je obrađen u 50 cm3 vode i 50 cm3 etilnog acetata uz snažno miješanje na temperaturi od 20°C, a potom je dodano 10 g kalijeva karbonata. Organska faza je isprana sa 25 cm3 vode, a zatim sa 25 cm3 zasićene vodene otopine natrijeva klorida, isušena na magnezijevom sulfatu, filtrirana i koncentrirana pod sniženim tlakom (l kPa) na temperaturi od 50°C. Dobiveno je 1.8 g Etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(2-kloroetil)piperidin-4-karboksilata.
Infra-crveni spektar (CCl4) : 2957; 1726; 1622; 1503; 1230; 1116; 1029 i 833 cm-1.
Etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(2-hidroksietil)piperidin-4-karboksilat
3.9 g etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilata i 2.07 g kalijeva karbonata je dodano otopini od 1.17 cm3 2-jodoetanola u 80 cm3 acetonitrila, na temperaturi od 20°C uz miješanje u inertnoj atmosferi. Nakon zagrijavanja tijekom 23 sata na temperaturi od 80°C, daljnjih 1.17 cm3 2-jodoetanola je dodano. Nakon zagrijavanja tijekom 40 sati na temperaturi od 80°C, reakcijska smjesa je ohlađena na približno 20°C, filtrirana i koncentrirana pod sniženim tlakom (1 kPa) na temperaturi od 50°C. Dobiveni ostatak je pročišćen kromatografijom pod tlakom dušika od 100 kPa, na stupcu silikagela (veličina čestice 40-60 μ; promjer 4 cm; visina 60 cm), eluiran sa smjesom diklorometan/metanol/vodena otopina amonijaka (89/10/1 omjer volumena) i sakupljanjem 50-cm3 frakcija. Frakcije 14 do 17 su kombinirane, a zatim koncentrirane kao što je prethodno navedeno. Dobiveno je 1.9 g etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(2-hidroksietil)piperidin-4-karboksilata.
Infra-crveni spektar (CCl4) : 2439; 2952; 1726; 1622; 1503; 1230; 1116; 1029 i 833 cm-1.
Primjer 19
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltioetil)piperidin-4-il]-metanol dihidroklorid
Smjesa 0.6 g {3-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]piperidin-4-il}metanol dihidroklorida, 0.24 g l-bromo-2-(ciklopentiltio)etila, 0.22 g kalijeva jodida i 0.9 g kalijeva karbonata u 25 cm3 acetonitrila je zagrijavana uz miješanje tijekom 20 sati na temperaturi od 75°C. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen sa 20 cm3 vode, a zatim ekstrahiran s 3 puta po 20 cm3 etilnog acetata. Organske faze su kombinirane, isušene na magnezijevom sulfatu, filtrirane i zatim koncentrirane do isušenja kao što je prethodno navedeno. Dobiveni ostatak je pročišćen kromatografijom pod tlakom dušika od 50 kPa, na stupcu silikagela (veličina čestice 20-45 μ; promjer 3 cm; visina 18 cm), eluiran sa smjesom diklorometan/metanol (90/10 omjer volumena). Frakcije koje sadržavaju očekivani produkt su kombinirane, a zatim koncentrirane do isušenja pod prethodno navedenim uvjetima. Dobiveni ostatak je obrađen sa 5 cm3 acetona, a zatim zakiseljen sa 3 cm3 1N otopine klorovodika u dietilnom eteru. Dobivena suspenzija je razrijeđena sa 20 cm3 dietilnog etera, miješana na temperaturi od 20°C tijekom 3 sata, filtrirana, isprana dietilnim eterom, a zatim isušena u sušilici pod sniženim tlakom (0.1 kPa) na temperaturi od 40°C. Dobiveno je 0.4 g 4-[3-(R,S)-hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(ciklopentiltioetil)-piperidin-4-il]-metanol dihidroklorida u obliku svijetložute krute tvari točke taljenja 120°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, uz dodatak nekoliko kapi CD3COOD-d4 na temperaturi od 373K, δ u ppm) : od 1.20 do 2.15 (mt: 16H); 2.93 (široki t, J = 7.5 Hz: 2H); od 3.10 do 3.30 (mt: 7H); 3.33 (široko s: 2H); 3.91 (s: 3H); 5.49 (mt: 1H); 7.41 (dd, J = 9 i 3 Hz: 1H); 7.93 (d, J = 9 Hz: 1H); 8.22 (d, J = 3 Hz: 1H); 8.60 (s: 1H).
{4-[3-(3-Kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]piperidin-4-il}metanol dihidroklorid
Smjesa od 1.5 g terc-butil 4-(terc-butildimetilsilaniloksimetil)-4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]piperidin-1-karboksilata u 6.5 cm3 5N klorovodične kiseline otopljene u dioksanu i 30 cm3 dioksana je miješana na temperaturi od 20°C tijekom 17 sati. Dodano je 100 cm3 dietilnog etera u reakcijsku smjesu. Nastali precipitat je filtracijom odvojen do nastanka 1.24 g {4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]piperidin-4-il}metanol dihidroklorida u obliku svijetložute krute tvari.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.20 do 2.10 (mt: 8H); od 2.85 do 3.10 (mt: 4H); 3.26 (široko s: 2H) ; 3.91 (s: 3H); 5.45 (mt: 1H); 7.47 (dd, J = 9 i 3 Hz: 1H); 7.98 (d, J = 9 Hz: 1H); 8.23 (d, J = 3 Hz: 1H); od 8.60 do 8.80 (nedefinirani vršak: 2H); 8.69 (s: 1H).
terc-Butil 4-(terc-butildimetilsilaniloksimetil)-4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]-piperidin-1-karboksilat
Otopina od 5.26 g terc-butil 4-(terc-butildimetilsilaniloksimetil)-4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-1-karboksilata u 300 cm3 dimetilnog sulfoksida i 75 cm3 terc-butanola je miješana u atmosferi zasićenoj kisikom na temperaturi od 20°C. Nakon 5 minuta, dodana je u reakcijsku smjesu otopina od 2.1 g kalijeva terc-butoksida u 30 cm3 terc-butanola. Nakon izlaganja kisiku tijekom l sata i 30 minuta, reakcijska smjesa je pažljivo izlivena na smjesu 300 g leda, 300 cm3 diklorometana. Organske faze su kombinirane, isprane sa dva puta po 300 cm3 vode, isušene na magnezijevom sulfatu, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod tlakom dušika od 50 kPa, na stupcu silikagela (veličina čestice 20-45 μ; promjer 4 cm; visina 27 cm), eluiranjem sa smjesom cikloheksan/etilni acetat (50/50 omjer volumena). Frakcije koje sadržavaju očekivani produkt su kombinirane, a zatim koncentrirane do isušenja pod prethodno navedenim uvjetima. Dobiveno je 3.4 g terc-butil 4-(terc-butildimetilsilaniloksi-metil)-4-[3-(3-kloro-6-metoksikinolin-4-il)-3-hidroksipropil]-piperidin-1-karboksilata u obliku bijele pjene.
Spektar mase: EI m/z = 578 M+
m/z = 521 C26H38ClN2O5Si+
m/z = 465 C22H30ClN2O5Si+
m/z = 421 C21H30Cln2O5Si+ bazni vršak
m/z = 57 C4H9+
DCI m/z =579 MH+
m/z = 523 C26H40ClN2O5Si+
terc-Butil 4-(terc-butildimetilsilaniloksimetil)-4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-1-karboksilat
Smjesa od 0.45 g terc-butil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-4-hidroksimetil-piperidin-1-karboksilata, 0.3 g terc-butildimetilsilil klorida, 0.17 cm3 trietilamina i 0.04 g dimetilaminopiridina u 20 cm3 diklorometana je miješana u inertnoj atmosferi na temperaturi od 20°C. Nakon miješanja tijekom 18 sati, dodano je 0.3 g terc-butildimetilsililnog klorida, 0.04 g dimetilaminopiridina i 0.2 cm3 trietilamina. Reakcijska smjesa je stavljena u 20 cm3 vode. Vodena faza je ekstrahirana s dva puta po 20 cm3 diklorometana. Organske faze su kombinirane, isprane s dva puta po 300 cm3 zasićene vodene otopine natrijeva klorida, isušene na magnezijevom sulfatu, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod tlakom dušika od 50 kPa, na stupcu silikagela (veličina čestice 20-45 μ; promjer 2.5 cm; visina 15 cm), eluiranjem sa smjesom cikloheksan/etilni acetat (70/30 omjer volumena). Frakcije koje sadržavaju očekivani produkt su kombinirane, a zatim koncentrirane do isušenja pod prethodno navedenim uvjetima. Dobiveno je 0.48 g terc-butil 4-(terc-butildimetilsilaniloksi-metil)-4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-1-karboksilata u obliku bezbojnog laka.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : -0.04 (s: 6H); 0.76 (s: 9H); 1.29 (mt: 4H); 1.39 (s: 9H); 1.58 (mt: 4H); 3.19 (mt: 2H); od 3.20 do 3.45 (mt: 6H); 3.95 (s: 3H);, 7.41 (d, J = 3 Hz: 1H); 7.45 (dd, J = 9 i 3 Hz: 1H); 7.95 (d, J = 9 Hz: 1H); 8.67 (s: 1H).
terc-Butil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-4-hidroksimetilpiperidin-1-karboksilat
1.05 g litij aluminijeva hidrida je dodano u dijelovima, uz miješanje u inertnoj atmosferi, u otopinu od 12.3 g etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(terc-butiloksikarbonil)-piperidin-1-karboksilata u 250 cm3 tetrahidrofurana, na temperaturi od -20°C. Nakon miješanja tijekom 2 sata na temperaturi od 20°C, dodano je u reakcijsku smjesu 0.5 g litij aluminijeva hidrida na temperaturi od -20°C. Nakon jednog sata i trideset minuta, reakcijska smjesa je ohlađena na 0°C, te je zatim hidrolizirana u slijedu dodavanjem 1.8 cm3 vode, 1.3 cm3 5N natrijeva hidroksida i 5.7 cm3 vode. Nakon miješanja tijekom 30 minuta na temperaturi od 20°C, reakcijska smjesa je filtrirana, a zatim isprana sa 400 cm3 etilnog acetata. Filtrat je ispran sa 200 cm3 zasićene otopine natrijeva klorida, isušen na magnezijevom sulfatu, a zatim koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 10.9 g terc-butil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-4-hidroksimetilpiperidin-1-karboksilata.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm): 1.23 (mt: 2H); 1.32 (mt: 2H); 1.39 (s: 9H); 1.58 (mt: 4H); od 3.10 do 3.40 (mt: 6H); 3.22 (d, J= 5 Hz: 2H); 3.96 (s: 3H); 4.50 (t, J = 5 Hz: 1H); 7.40 (d, J = 3 Hz: 1H); 7.45 (dd, J = 9 i 3 Hz: 1H); 7.96 (d, J = 9 Hz: 1H); 8.68 (s: 1H).
Etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(terc-butiloksikarbonil)piperidin-4-karboksilat je pripravljen u Primjeru 5.
Primjer 20
4-[3-(3-Kloro-6-metoksikinolin-4-il)-3-(R,S)-fluoropropil]-1-(3-fenilpropil)piperidin-4-karboksilna kiselina
Smjesa od 0.5 g metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-fluoropropil]-1-(3-fenilpropil)piperidin-4-karboksilata u 8 cm3 5N vodene otopine klorovodične kiseline je održavana na temperaturi od 100°C, uz miješanje u inertnoj atmosferi tijekom 6 sati. Nakon miješanja tijekom 18 sati na temperaturi od 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen sa 10 cm3 diklorometana i filtriran. Filtrat je koncentriran do isušenja pod gore navedenim uvjetima, obrađen sa diizopropilnim eterom, a zatim isušen u sušilici pod sniženim tlakom (0.1 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod tlakom dušika od 60 kPa, na stupcu silikagela (veličina čestice 20-45 μ; promjer 2.5 cm; visina 40 cm), eluiran sa smjesom diklorometan/metanol/vodena otopina amonijaka (83/15/2 omjera volumena). Frakcije 13 do 20 su kombinirane, a potom koncentrirane do isušenja pod prethodno navedenim uvjetima. Dobiveno je 0.24 g 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-fluoropropil]-1-(3-fenilpropil)piperidin-4-karboksilne kiseline u obliku bijele krute tvari točke taljenja 240°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.20 do 2.35 i od 2.40 do 2.70 (mts: 18H ukupno); 3.94 (široko s: 3H); 6.36 (2 mts, JHF = 48 Hz: 1H); od 7.10 do 7.35 (mt: 5H); 7.52 (široko d, J = 9 Hz: 1H); 7.57 (široko s: 1H); 8.02 (široko d, J = 9 Hz: 1H); 8.75 (široko s: 1H).
Metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-fluoropropil]-1-(3-fenilpropil)piperidin-4-karboksilat
0.31 cm3 dietilaminosulfur trifluorida je dodano u otopinu od 0.66 g metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]-1-(3-fenil-propil)piperidin-4-karboksilata u 40 cm3 diklorometana, uz miješanje u inetnoj atmosferi, na temperaturi od -15°C. Nakon miješanja tijekom 3 sata na temperaturi od 20°C, dodano je u reakcijsku smjesu 0.31 cm3 dietilaminosulfur trifluorida, a zatim 20 cm3 zasićene otopine natrijeva hidrogen karbonata. Vodena faza je ekstrahirana s 20 cm3 diklorometana. Organske faze su kombinirane, isprane zasićenom otopinom natrijeva klorida, isušene na magnezijevom sulfatu, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod tlkaom dušika od 100 kPa, na stupcu silikagela (veličina čestice 20-45 μ; promjer 3.5 cm; visina 35 cm), eluiran sa smjesom diklorometan/metanol (97/3 omjera volumena). Frakcije 15 do 21 su kombinirane, a potom koncentrirane do isušenja pod prethodno navedenim uvjetima. Dobiveno je 0.5 g 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-fluoropropil]-1-(3-fenilpropil)piperidin-4-karboksilata u obliku smeđeg ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.30 do 2.35 i od 2.50 do 2.80 (mts: 18H ukupno); 3.54 (s: 3H); 3.93 (s: 3H); 6.36 (ddd, JHF = 48-8.5 i 4.5 Hz: 1H); od 7.19 (mt: 5H); 7.29 (široko t, J - 7.5 Hz: 2H); 7.52 (mt: 2H); 8.04 (d, J = 9 Hz: 1H); 8.75 (široko s: 1H).
Metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]-1-(3-fenilpropil)piperidin-4-karboksilat
Smjesa od l g metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]piperidin-4-karboksilata, 0.58 g 1-bromo-3-fenilpropana i 0.53 g kalijeva karbonata u 50 cm3 acetonitrila je zagrijavana tijekom 22 sata na temperaturi od 75°C, uz miješanje u inertnoj atmosferi. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je filtrirana i isprana acetonitrilom. Filtrat je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod tlakom dušika od 100 kPa, na stupcu silikagela (veličina čestice 70-200 μ; promjer 3.5 cm; visina 40 cm), eluiranjem sa diklorometanom/metanolom (95/05). Frakcije 21 do 48 su kombinirane i koncentrirane do isušenja pod gore navedenim uvjetima. Dobiveno je 0.7 g metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksi-propil]-1-(3-fenilpropil)piperidin-4-karboksilata.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.20 do 2.35 i od 2.45 do 2.75 (mts: 18H ukupno); 3.48 (s: 3H); 3.88 (s: 3H); 5.40 (mt: 1H); 6.07 (d, J = 4 Hz: 1H); od 7.20 do 7.25 (mt: 3H); 7.27 (široko t, J = 7.5 Hz: 2H); 7.44 (dd, J = 9 i 3 Hz: 1H); 9.96 (d, J = 9 Hz: 1H); 8.14 (d, J = 3 Hz: 1H); 8.66 (s: 1H).
Metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]piperidin-4-karboksilat je pripravljen u Primjeru 49.
Primjer 21
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-karboksilat je pripravljen u obliku žutog ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm): od 1.35 do 1.60 (mt: 4H ukupno); 1.74 (mt: 2H); od 1.95 do 2.10 (mt: 4H); 2.40 (t, J = 7.5 Hz: 2H); od 2.60 do 2.75 (mt: 2H); 3.07 (mt: 2H); 3.15 (široko t, J = 7.5 Hz: 2H); 3.94 (s: 3H); 5.05 (s: 2H); 6.05 (široko t, J = 5 Hz: 1H); od 6.15 do 6.30 (mt: 3H); 7.27 (mt: 5H); 7.36 (d, J = 2.5 Hz: 1H); 7.47 (dd, J = 9 i 2.5 Hz: 1H); 7.98 (d, J = 9 Hz: 1H); 8.68 (s: 1H).
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilami.no) etil]piperidin-4-karboksilna kiselina
Smjesa od 0.73 g benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-karboksilata u 12 cm3 5N klorovodične kiseline je održavana na temperaturi od 100°C, uz miješanje u inertnoj atmosferi tijekom 3.5 sata. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je uparena pod sniženim tlakom (2 kPa) na temperaturi od 50°C. Uparavanjem dobiveni ostatak je obrađen sa 50 cm3 acetona, a zatim je koncentriran do isušenja pod gore navedenim uvjetima. Dobivena pjena je pročišćena kromatografijom pod tlakom argona od 50 kPa, na stupcu silikagela (veličina čestice 20-45 μ; promjer 2.5 cm; visina 38 cm), eluirana sa smjesom kloroform/metanol/vodena otopina amonijaka (12/3/0.5 omjera volumena). Frakcije 31 do 46 su kombinirane, a potom koncentrirane do isušenja pod prethodno navedenim uvjetima. Dobiveni prašak je isušen u pećnici pod sniženim tlakom (0.1 kPa) na temperaturi od 40°C. 0.28 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenilamino)etil]piperidin-4-karboksilne kiseline u obliku ružičasto-bijele krute tvari točke taljenja 210°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.45 (široko t, J = 12.5 Hz: 2H); 1.56 (mt: 2H); 1.68 (mt: 2H); od 1.90 do 2.10 (mt: 4H); 2.41 (t, J = 6.5 Hz: 2H); 2.66 (široko d, J = 12 Hz: 2H); 3.08 (mt: 2H); 3.18 (široko t, J = 7.5 Hz: 2H); 3.97 (s: 3H); 6.08 (široko t, J = 4.5 Hz: 1H); od 6.15 do 6.30 (mt: 3H); 7.38 (d, J = 2.5 Hz: 1H); 7.45 (dd, J = 9 i 2,5 Hz: 1H); 7.96 (d, J = 9 Hz: IH: 1H); 8.68 (s: 1H).
Primjer 22
4-[3-(R,S)-Hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-3-il)tioetil]piperidin-4-il metanol
321
Smjesa 0.6 g etilnog {4-[3-(3-kloro-6-metoksikinolin-4il)-3-(R,S)-hidroksipropil]piperidin-4-il}metanol dihidroklorid, 0.34 g 2-(2-bromoetiltio)tiofena i 0.95 g kalijeva karbonata i 0.23 g kalijeva jodida u 25 cm3 acetonitrila je zagrijavana tijekom 17 sati na temperaturi od 80°C, uz miješanje u inertnoj atmosferi. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je razrijeđena sa 30 cm3 vode, a zatim ekstrahirana s dva puta po 30 cm3 etilnog acetata. Organski ekstrakti su kombinirani, a zatim koncentrirani do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno ulje je pročišćeno kromatografijom pod tlakom argona od 50 kPa, na stupcu silikagela (veličina čestice 20-45 μ; promjer 3 cm; visina 27 cm), eluiranjem sa smjesom diklorometan/metanol (93/7 omjer volumena). Frakcije koje sadrže produkt su kombinirane, a zatim koncentrirane do isušenja pod gore navedenim uvjetima. Dobiveno ulje je zakiseljeno s 2 cm3 1N klorovodičnog etera, razrijeđeno sa 20 cm3 dietilnog etera i miješano tijekom l sata na temperaturi od 20°C. Kruta tvar je filtracijom odvojena, isprana dietilnim eterom, a zatim isušena u pećnici pod sniženim tlakom (10 kPa) na temperaturi od 40°C. Dobiveno je 0.28 g 4-[3-(R,S)-hidroksi-3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-3-il)tioetil]piperidin-4-il} metanol hidroklorida u obliku žuto obojene krute tvari točke taljenja 118°C koja prelazi u pastu.
1H NMR Spektar (400 MHz, (CD3)2SO-d6, δ u ppm). Dobivena je smjesa od dva dijastereoizomera u približnom omjeru proprorcija 50/50.
* od 1.35 do 2.10 (mt: 8H); od 2.85 do 3.60 (mt: 10H); 3.86 do 3.87 (2s: 3H ukupno); 5.41 (mt: 1H); od 5.80 do 6.30 (široki nedefinirani vršak: 1H); 7.10 (mt: 1H); 7.29 (mt: 1H); 7.43 (dd, J = 9 i 3 Hz: 1H); 7.70 (mt: 1H); 7.94 (d, J = 9 Hz: 1H); 8.19 (široko s: 1H); 8.64 (s: 1H); 9.48 (nedefinirani vršak: 1H).
{4-[3-(3-Kloro-6-metoksikinolin-4-il)-3-(R,S) -hidroksipropil]piperidin-4-il}metanol dihidroklorid je pripravljen u Primjeru 19.
Primjer 23
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)piperidin-4-karboksamid
15.6 cm3 0.5N vodene otopine amonijaka u dioksanu, 0.26 g 1-hidroksibenzotriazolnog hidrata, 0.75 g 1-[3-(dimetilamino)propil]-3-etilkarbodiimidnog hidroklorida i 0.55 cm3 trietilamina je dodano smjesi od 0.75 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)piperidin-4-karboksilne kiseline u obliku natrijeve soli, u 20 cm3 diklorometana. Dobivena suspenzija je miješana tijekom 17 sati na temperaturi od 20°C. Reakcijska smjesa je razrijeđena sa 25 cm3 vode i miješana, a faze su razdvojene taloženjem. Vodena faza je ekstrahirana sa dva puta po 25 cm3 diklorometana, a organski ekstrakti su kombinirani, isprani sa 25 cm3 fiziološke otopine, isušeni na magnezijevom sulfatu, a zatim koncentrirani do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je pročišćen kromatografijom pod tlakom argona od 50 kPa, na stupcu silikagela (veličina čestice 20-45 μ; promjer 3 cm; visina 21 cm), eluiranjem sa smjesom diklorometan/metanol (90/10 omjer volumena). Frakcije koje sadrže produkt su kombinirane, a zatim koncentrirane do isušenja pod gore navedenim uvjetima. Dobiveno je 0.22 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)piperidin-4-karboksamida u obliku bijele krute tvari točke taljenja 160°C.
1H NMR Spektar (400 MHz, (CD3)2SO-d6, δ u ppm). 1.33 (široko t, J = 12 Hz: 2H); 1.53 (mt: 2H); 1.67 (mt: 4H); 1.98 (mt: 4H); 2.20 (t, J = 7.5 Hz: 2H); od 2.40 do 2.60 (mt: 4H) ; 3.15 (t, J = 7.5 Hz: 2H); 3.97 (s: 3H); 6.87 (s: 1H); 7.10 (s: 1H); 7.20 (široko d, J = 7.5 Hz: 2H); 7.27 (široko t, J = 7.5 Hz: 2H); 7.37 (d, J = 2.5 Hz: 1H); 7.45 (dd, J = 9 i 2.5 Hz: 1H); 7.96 (d, J = 9 Hz: 1H); 8.68 (s: 1H).
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)piperidin-4-karboksilna kiselina dihidroklorid je pripravljen u Primjeru 4.
Primjer 24
4-[3-(3-Kloro-6,7-dimetoksikinolin-4-il)propil]-1-[2-(tiofen-2-iltio) etil]piperidin-4-karboksilna kiselina
26 cm3 5N otopine natrijeva hidroksida i 20 cm3 metanola je dodano otopini od 1.47 g etil 4-[3-(3-kloro-6, 7-dimetoksikinolin-4-il)propil]-1-[2-(tiofen-2-iltio)etil]-piperidin-4-karboksilata u 20 cm3 dioksana, uz miješanje na temperaturi od 20°C, a temperatura smjese je zatim odražavana na 70°C tijekom 21 sata. Reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod tlakom argona od 50 kPa, na stupcu silikagela (veličina čestice 40-63 μ; masa 60 g), eluiranjem sa smjesom diklorometan/metanol/ vodena otopina amonijaka (12/3/0.5 omjer volumena). Frakcije 11 do 25 su kombinirane, a zatim koncentrirane do isušenja pod gore navedenim uvjetima. Dobiveno je 1.03 g 4-[3-(3-kloro-6,7-dimetoksikinolin-4-il)propil]-1-[2-(tiofen-2-iltio)etil] piperidin-4-karboksilne kiseline u obliku bijele krute tvari točke taljenja 214°C.
1H NMR Spektar (400 MHz, (CD3)2SO-d6, δ u ppm). 1.27 (vrlo široko t, J = 12 Hz: 2H); od 1.45 do 1.75 (mt: 4H) ; od 1.85 do 2.10 (mt: 4H); 2.44 (mt: 2H); od 2.50 do 2.65 (mt: 2H); 2.98 (široko t, J = 7.5 Hz: 2H); 3.13 (mt: 2H); 3.93 (s: 3H); 3.96 (s: 3H); 7.02 (dd, J = 5.5 i 3.5 Hz: 1H); 7.15 (dd, J = 3.5 i l Hz: 1H); 7.30 (široko s: 1H); 7.58 (dd, J = 5.5 i l Hz: 1H); 8.58 (s: 1H).
Etil 4-[3-(3-kloro-6,7-dimetoksikinolin-4-il)propil]-1-[2-(tiofen-2-iltio)etil]piperidin-4-karboksilat
Smjesa 0.65 g etil 4-[3-(3-kloro-6,7-dimetoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.16 g 2-(2-bromo-etiltio)tiofena, 1.63 g kalijeva karbonata 50 cm3 acetonitrila je miješana tijekom 23 sata na temperaturi od 20°C. Suspenzija je filtrirana, a filtrat je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je stavljen u 50 cm3 etilnog acetata, ispran sa dva puta po 50 cm3 vode i 40 cm3 zasićene vodene otopine natrijeva klorida, isušen na magnezijevom sulfatu, filtriran i koncentriran do isušenja pod gore navedenim uvjetima. Dobiveno ulje je pročišćeno kromatografijom pod tlakom argona od 50 kPa, na stupcu silikagela (veličina čestice 40-63 μ; promjer 4 cm), eluirano sa smjesom diklorometan/metanol/ acetonitril (95/2.5/2.5 omjer volumena). Frakcije koje sadržavaju očekivani produkt su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 1.47 g 4-[3-(3-kloro-6,7-dimetoksikinolin-4-il)propil]-1-[2-(tiofen-2-iltio)etil]-piperidin-4-karboksilne kiseline u obliku ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.05 (t, J = 7 Hz: 3H); 1.37 (široko t, J = 12 Hz: 2H); 1.52 (mt: 2H); od 1.60 do 1.75 (mt: 2H); od 1.85 do 2.05 (mt: 4H); 2.46 (mt: 2H); 2.61 (široko d, J = 12 Hz: 2H); 2.91 (mt: 2H); 3.15 (široko t, J = 7.5 Hz: 2H); 3.95 (s: 3H); 3.97 (s: 3H); 4.00 (q, J = 7 Hz: 2H); 7.04 (dd, J = 5.5 i 3.5 Hz: 1H); 7.17 (dd, J = 3.5 i l Hz: 1H); 7.31 (široko s: 1H); 7.40 (široko s: 1H); 7.60 (dd, J = 5.5 i l Hz: 1H); 8.61 (s: 1H).
Etil 4-[3-(3-kloro-6,7-dimetoksikinolin-4-il)piperidin-4-karboksilat
3 cm3 trifluorooctene kiseline je dodano kap po kap u smjesu od 2.05 g etil 4-[3-(3-kloro-6,7-dimetoksikinolin-4-il)propil]-1-(terc-butiloksikarbonil)piperidin-4-karboksilat u 20 cm3 diklorometana, uz miješanje na temperaturi od 20°C. Nakon 2 sata, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Ostatak je stavljen u 20 cm3 vode i 10 cm3 etilnog acetata, a zatim ekstrahiran sa dva puta po 10 cm3 1N vodene otopine klorovodične kiseline. Vodena faza je postala bazična dodavanjem vodene otopine 30% natrijeva hidroksida sve do postizanja pH vrijednosti od približno 10, a zatim je ekstrahirana sa 3 puta po 30 cm3 etilnog acetata. Organski ekstrakti su kombinirani, isušeni na magnezijevom sulfatu, filtrirani, a zatim koncentrirani do isušenja kao što je prethodno navedeno. Dobiveno je 1.65 g etil 4-[3-(3-kloro-6,7-dimetoksikinolin-4-il)piperidin-4-karboksilata u obliku žutog ulja.
Spektar mase: EI m/z = 420 M+ m/z = 364 C19H23ClNO4+
m/z = 264 C14H15ClNO2+ m/z = 237
C12H12ClNO2+ vršak baze
m/z = 184 C10H18NO2+
Etil 4-[3-(3-kloro-6,7-dimetoksikinolin-4-il)propil]-1-(terc-butiloksikarbonil) piperidin-4-karboksilat
21 cm3 0.5M otopine 9-borabiciklo[3.3.1]nonana je ohlađeno na temperaturu od 0°C i dodano je kap po kap 2.61 g etil 4-alil-1-(terc-butiloksikarbonil)-piperidin-4-karboksilata u 26 cm3 tetrahidrofurana, uz miješanje u inertnoj atmosferi, te odražavanjem temperature na približno 0°C. Po završetku dodavanja, temperatura smjese je vraćena na 20°C. Dobivena otopina je miješana tijekom daljnja 4 sata na navedenoj temperaturi, zatim je dodano 37 cm3 dioksana, 0.19 g paladij-difenilfosfinoferocen klorida, 3.05 g 4-bromo-3-fluoro-6-metoksikinolina i 5.58 g tribazičnog kalijevog fosfata. Nakon miješanja tijekom 24.75 sati na temperaturi od 60°C, reakcijska smjesa je ohlađena na približno 20°C i filtrirana, a filtrat je zatim koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je stavljen u 100 cm3 etilnog acetata i 100 cm3 vode, faze su odvojene taloženjem, a organska faza je zatim isprana sa 100 cm3 zasićene otopine natrijeva klorida. Organska faza je isušena na magnezijevom sulfatu, filtrirana i koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno ulje je pročišćeno kromatografijom, pod tlakom argona od 50 kPa, na stupcu silikagela (veličina čestice 40-63 μ; volumen 690 cm3), eluiranjem sa smjesom diklorometan/metanol/ acetonitril (98/1/1 omjer volumena). Frakcije koje sadržavaju očekivani produkt su kombinirane, a zatim koncentrirane do isušenja u skladu s prethodno navedenim uvjetima. Dobiveno je 2.16 g etil 4-[3-(3-kloro-6,7-dimetoksikinolin-4-il)propil]-1-(terc-butiloksikarbonil)piperidin-4-karboksilata u obliku žutog gela.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.06 (t, J = 7 Hz: 3H); od 1.25 do 1.45 (mt: 2H); 1.39 (s: 9H); 1.53 (mt: 2H); 1.69 (mt: 2H); 1.93 (široko d, J = 13.5 Hz: 2H); 2.82 (nedefinirani vršak: 2H); 3.14 (široko t, J = 7.5 Hz: 2H); 3.69 (široko d, J = 13.5 Hz: 2H); 3.94 (s: 3H); 3.97 (s: 3H); 4.03 (q, J = 7 Hz: 2H); 7.31 (široko s: 1H); 7.40 (široko s: 1H); 8.61 (s: 1H).
4-Bromo-3-kloro-6,7-dimetoksikinolin
19 g trifenilfosfin dibromida je dodano u otopinu od 5.39 g 3-kloro-4-hidroksi-6,7-dimetoksikinolina u 270 cm3 acetonitrila, uz miješanje na temperaturi od 20°C. Reakcijska smjesa je zagrijavana na približno 80°C tijekom 8.25 sati. Nakon hlađenja na temperaturu od 20°C, netopljivi materijal je filtracijom odvojen. Dobiveno je 5.67 g 4-bromo-3-kloro-6,7-dimetoksikinolina u obliku sive krute tvari.
Spektar mase: DCI m/z = 302 MH+
3-Kloro-4-hidroksi-6,7-dimetokiskinolin
5.45 g N-klorosukcinimida je dodano u otopinu [lakuna] 6,7-dimetoksikinolin-4-ola u 300 cm3 octene kiseline, uz miješanje i na temperaturi od 20°C. Reakcijska smjesa je zagrijavana na temperaturu od 50°C tijekom 6 sati. Nakon hlađenja na približno 20°C i miješanja tijekom 18 sati na navedenoj temperaturi, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dodano je kap po kap 100 cm3 otopine natrijeva hidrogen karbonata u upareni ostatak i suspenzija je zatim miješana tijekom 24 sata na temperaturi od 20°C. Netopljivi materijal je filtracijom odvojen, a zatim isušen u pećnici pod sniženim tlakom (20 kPa). Dobiveno je 5.39 g 3-kloro-4-hidroksi-6,7-dimetoksikinolina u obliku tamnozelene krute tvari.
Spektar mase: DCI m/z = 240 MH+
6,7-Dimetoksi-4-hidroksikinolin
Smjesa od 0.24 g 4-hidroksi-6,7-dimetoksikinolin-3-karboksilne kiseline u 185 cm3 difenilnog etera je održavana, uz mehaničko miješanje, na temperaturi od 250°C tijekom 1.3 sata. Nakon hlađenja reakcijske smjese na približno 20°C, dodano je 100 cm3 diizopropilnog etera. Suspenzija je miješana tijekom 8 sati i filtrirana, filtracijom dobivena masa je isprana sa 3 puta po 100 cm3 diizopropilnog etera. Dobiveno je 7.96 g 6,7-dimetoksikinolin-4-ola u obliku smeđe krute tvari.
Infra-crveni spektar (KBr): 3242; 1605; 1548; 1500; 1273; 1239: 1220; 1075 i 822 cm-1.
4-Hidroksi-6,7-dimetoksikinolin-3-karboksilna kiselina
10.2 g fosfornog pentoksida je oprezno dodano, uz mehaničko miješanje, smjesi od 21.1 g dietilnog 2-[(3,4-dimetoksifenilamino)-metilen]malonata u 42 cm3 nitrobenzena. Temperatura reakcijske smjese je održavana na 150°C tijekom 4 sata. Nakon hlađenja na 20°C i miješanje tijekom 18 sati na istoj temperaturi, dodano je kap po kap 14 cm3 vode, a reakcijska smjesa je zatim zagrijavana na približno 110°C tijekom 7 sati. Nakon hlađenja na temperaturu od 20°C, dodano je 42 cm3 etilnog acetata. Suspenzija je miješana pod navedenim uvjetima tijekom 18 sati, faze su zatim odvojene taloženjem, organska faza je filtrirana, a filtracijom dobivena masa je isprana sa 3 puta po 40 cm3 etilnog acetata, 40 cm3 etanola i 40 cm3 vode. Dobiveno je 9.25 g 4-hidroksi-6,7-dimetoksikinolin-3-karboksilne kiseline u obliku krem obojene krute tvari.
Infra-crveni spektar (KBr): 2842; 1673; 1631; 1590; 1503; 1437; 1279; 1220; 1006; 807; 586 i 357 cm-1.
Dietil 2-[(3,4-dimetoksifenilamino)metilen]malonat
Smjesa od 10 g 3,4-dimetoksianilina u 13.2 cm3 dietilnog etoksimetilenmalonata je miješana tijekom 1.5 sati na temperaturi od 110°C. Nakon hlađenja na 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 50°C. Dobiveno je 21.1 g dietilnog 2-[(3,4-dimetoksifenilamino)metilen]malonata u obliku smeđe krute tvari.
Spektar mase: DCI m/z = 324 MH+
Etil 4-alil-1-(terc-butiloksikarbonil)-piperidin-4-karboksilat je pripravljen u Primjeru 1.
Primjer 25
4-[3-(3-Kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]-1-[2-(2,5-difluorofeniltio)etil]-piperidin-4-karboksilna kiselina monohidroklorid
5 cm3 5N otopine natrijeva hidroksida je dodano u otopinu od 0.6 g (R,S)-3-(3-kloro-6-metoksikinolin-4-il)-9-[2-(2,5-difluorofeniltio)-etil]-2-oksa-9-azaspiro[5.5]undekan-1-ona u 50 cm3 acetona, uz miješanje na temperaturi od 20°C. Nakon 2 sata, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je stavljen u 10 cm3 dietilnog etera i filtriran, a filtracijom dobivena masa je isprana sa dietilnim eterom, a zatim isušena u pećnici pod sniženim tlakom (10 kPa) na temperaturi od 50°C. Kruta tvar je stavljena u vodu i zakiseljena dodatkom 1N vodene otopine klorovodične kiseline do postizanja pH vrijednosti od 3. Dodan je diklorometan na temperaturi od 20°C uz umjereno miješanje, a kruta tvar je zatim filtracijom odvojena. Dobiveno je 0.32 g 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]-1-[2-(2,5-difluorofeniltio)etil]-piperidin-4-karboksilna kiselina monohidroklorida u obliku bijele krute tvari.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.30 do 2.35 (mt: 8H); 2.84 (nedefinirani vršak: 2H); od 3.05 do 3.70 (mt: 6H); 3.90 (široko s: 3H); 5.43 (nedefinirani vršak: 1H); 6.16 (nedefinirani vršak: 1H); 7.14 (nedefinirani vršak: 1H); 7.33 (nedefinirani vršak: 1H); 7.46 (mt: 2H); 7.96 (široko d, J = 9 Hz: 1H); 8.16 (široko s: 1H); 8.67 (široko s: 1H); od 10.20 do 10.60 (široki nedefinirani vršak: 1H).
4-[3-(3-Kloro-6-metoksikinolin-4-il)-9-[2-(2,5-difluorofeniltio)etil]-2-oksa-9-azaspiro[5.5]undekan-1-on
Smjesa od 1.75 g 4-[3-(3-kloro-6-metoksikinolin-4-il)-(R,S)-propil]piperidin-4-karboksilatnog dihidroklorida, 0.95 g 2-(2-bromoetiltio)-l,4-difluorobenzena, 0.62 g kalijeva jodida i 3.11 g kalijeva karbonata u 30 cm3 acetonitrila i 20 cm3 dimetilformamida je zagrijavana uz miješanje tijekom 18 sati na temperaturi od 85°C. Nakon hlađenja na 20°C, reakcijska smjesa je filtrirana na dijatomejskoj zemlji (Celit), a filtrat je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen s vodom i dietilnim eterom. Organska faza je isušena na magnezijevom sulfatu, filtrirana i koncentrirana do isušenja kao što je prethodno navedeno. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 70-200 μ; promjer 4 cm), eluiranjem sa smjesom diklorometan/metanol (97.5/2.5 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane i koncentrirane do isušenja pod prethodno navedenim uvjetima. Dobiveno je 0.6 g 3-(3-kloro-6-metoksikinolin-4-il)-9-[2-(2, 5-difluorofeniltio)etil]-2-oksa-9-azaspiro[5.5]undekan-1-ona. Spektar mase: EI m/z = 532 M+ m/z = 373 C20H22ClN2O3+ vršak baze
2-(2-Bromoetiltio)-l,4-difluorobenzen je pripravljen u Primjeru 14.
Metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]piperidin-4-karboksilat je pripravljen u Primjeru 49.
Primjer 26
4-[3-(3-Kloro-6-metoksikinolin-4-il)-3-(R,S)-fluoropropil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-karboksilat
Smjesa od 0.4 g metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-fluoropropil]-1-[2-(3,5-difluorofenoksi)etil]-piperidin-4-karboksilata u 6.6 cm3 5N vodene otopine klorovodične kiseline je održavana na temperaturi od 100°C, uz miješanje u inertnoj atmosferi tijekom 6 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je miješana tijekom 20 sati na navedenoj temperaturi, a zatim koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen sa smjesom diklorometan/metanol (90/10 omjer volumena), a zatim koncentriran do isušenja ponovno pod istim uvjetima. Uparavanjem dobiveni ostatak je pročišćen kromatografijom pod tlakom argona od 60 kPa, na stupcu silikagela (veličina čestice 40-60 μ; promjer 2.5 cm; visina 41 cm), eluiranjem sa smjesom diklorometan/metanol/28% vodena otopina amonijaka (83/15/2 omjera volumena) i sakupljanjem 30-cm3 frakcija. Frakcije 16 do 22 su kombinirane, a potom koncentrirane do isušenja pod prethodno navedenim uvjetima. Dobiveni ostatak je raspoređen u 10 cm3 diizopropilog etera, filtriran i isušen. Dobiveno je 0.21 g 4-[3-(3-kloro-6-metoksikinolin-4-il) -3- (R, S) -fluoropropil] -1- [2- (3, 5-dif luorofenoksi) etil] piperidin-4-karboksilata u obliku prljavo bijele krute tvari točke taljenja 205°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.20 do 1.70 (mt: 3H); od 1.80 do 2.40 (mt: 7H); od 2.30 do 2.80 (mt: 2H); 2.61 (t, J = 6 Hz: 2H); 3.92 (s: 3H)/ 4.17 (t, J = 6 Hz: 2H); 6.36 (d mt, JHF = 48 Hz: 1H); od 6.65 do 6.85 (mt: 3H) ; 7.51 (dd, J = 9 i 2.5 Hz: 1H); 7.55 (široko s: 1H); 8.02 (d, J = 9 Hz: 1H); 8.74 (s: 1H).
Metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-fluoropropil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-karboksilat
0.4 cm3 dietilaminosulfurng trifluorida je dodano u otopinu od 1.1 g metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]-1-[2-(3,5-difluorofenoksi)etil]-piperidin-4-karboksilata u 50 cm3 diklorometana, uz miješanje u inertnoj atmosferi, na temperaturi od -10°C. Nakon miješanja tijekom 4 sata na temperaturi od 20°C, dodano je u reakcijsku smjesu 0.4 cm3 dietilaminosulfurnog trifluorida i reakcijska smjesa je zatim miješana tijekom 20 sati na navedenoj temperaturi. Dodano je zatim 20 cm3 zasićene otopine natrij hidrogen karbonata. Vodena faza je ekstrahirana sa 25 cm3 diklorometana. Organska faza je isprana sa dva puta po 25 cm3 10% vodene otopine (u težini) natrijeva klorida, isušena na magnezijevom sulfatu, a zatim koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno ulje je pročišćeno kromatografijom pod tlakom argona od 100 kPa, na stupcu silikagela (veličina čestice 40-60 μ; promjer 3.5 cm; visina 35 cm), eluiranjem sa smjesom diklorometan/metanol (97/3 omjera volumena) i sakupljanjem 35-cm3 frakcija. Frakcije 20 do 21 su kombinirane, a potom koncentrirane do isušenja pod prethodno navedenim uvjetima. Dobiveno je 0.62 g metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-fluoropropil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-karboksilata u obliku narančasto obojenog ulja.
Infra-crveni spektar: (CH2Cl2) : 2953; 1725; 1622; 1599; 1504; 1466; 1234; 1152; 1117 i 837 cm-1.
Metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-karboks ilat
0.47 cm3 tionilnog klorida je dodano kap po kap, uz miješanje u inertnoj atmosferi, u smjesu od 1.1 g 3-(3-kloro-6-metoksikinolin-4-il)-9-[2-(3,5-difluorofenoksi)-etil]-2-oksa-9-azaspiro[5.5]undekan-1-ona u 20 cm3 metanola i ohlađeno je na -20°C, a smjesa je potom miješana tijekom 24 sata na temperaturi od 20°C. Reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Ostatak je obrađen sa 30 cm3 etilnog acetata i 15 cm3 vode. Nakon dodatka 5 g kalijeva karbonata i snažnog miješanja tijekom 5 minuta, smjesa je ostavljena da se istaloži, a organska faza je odvojena i isprana sa 3 puta po 15 cm3 10% vodene otopine (u težini) natrijeva klorida. Nakon sušenja na magnezijevom sulfatu, a potom filtracije, organska otopina je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 1.12 g metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-karboksilata u obliku smeđeg laka.
Infra-crveni spektar: (CCl4) : 3615; 2952; 1732; 1622; 1600; 1466; 1233; 1154; 1117; 841 i 671 cm-1.
3-(3-Kloro-6-metoksikinolin-4-il)-9-[2-(3,5-difluorofenoksi)-etil]-2-oksa-9-azaspiro[5.5]undekan-1-on
Smjesa od l g metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]piperidin-4-karboksilata, 0.8 g 1-(2-bromoetoksi)-3,5-difluorobenzena i 0.42 g kalijeva karbonata u 45 cm3 acetonitrila je održavana na temperaturi od 80°C uz miješanje u atmosferi argona tijekom 20 sati. Suspenzija je filtrirana, netopljivi materijal je ispran etilnim acetatom, a filtrat je zatim koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Ostatak je pročišćen kromatografijom pod tlakom argona od 100 kPa, na stupcu silikagela (veličina čestice 40-60 μ; promjer 3.5 cm; visina 38 cm), eluiranjem sa smjesom diklorometan/metanol (97/4 omjer volumena) i sakupljanjem 35-cm3 frakcija. Frakcije 9 i 20 su kombinirane i koncentrirane do isušenja pod prethodno navedenim uvjetima. Dobiveno je 1.1 g 3-(3-kloro-6-metoksikinolin-4-il)-9-[2-(3,5-difluorofenoksi)etil]-2-oksa-9-azaspiro[5.5]undekan-1-ona.
Infra-crveni spektar: (CCl4) : 2940; 1735; 1622; 1600; 1503; 1467; 1233; 1153; 1117; 841 i 671 cm-1.
Metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-hidroksipropil]piperidin-4-karboksilat je pripravljen u Primjeru 49.
1-(2-Bromoetoksi)-3,5-difluorobenzen se može pripraviti primjenom postupka opisanog u Primjeru 16.
Primjer 27
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-karboksamid
13.4 cm3 0.5N vodene otopine amonijaka u dioksanu, 0.229 g 1-hidroksibenzotriazolnog hidrata, 0.64 g 1-[3-(dimetilamino)-propil]-3-etilkarbodiimidnog hidroklorida i 0.46 cm3 trietilamina je dodano, uz miješanje u inertnoj atmosferi, u smjesu od 0.69 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-karboksilne kiseline u 30 cm3 diklorometana. Dobivena suspenzija je miješana tijekom 17 sati na temperaturi od 20°C. Reakcijska smjesa je razrijeđena sa 50 cm3 vode, miješana, a faze su razdvojene taloženjem. Vodena faza je ekstrahirana sa dva puta po 25 cm3 diklorometana i organski ekstrakti su kombinirani, isprani sa 25 cm3 zasićene vodene otopine natrijeva klorida, isušeni na magnezijevom sulfatu, a zatim koncentrirani do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Kruta tvar je obrađena sa 20 cm3 diizopropilnog etera, miješana, a zatim filtrirana. Dobiveno je 0.52 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3, 5-difluoro-fenoksi)etil]piperidin-4-karboksamida.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.34 (široko t, J = 12.5 Hz: 2H); 1.54 (mt: 2H); 1.66 (mt: 2H); 2.02 (široko d, J = 12.5 Hz: 2H); 2.12 (široko t, J = 11 Hz: 2H); od 2.55 do 2.75 (mt: 4H); 3.16 (široko t, J = 7.5 Hz: 2H); 3.97 (s: 3H); 4.08 (t, J = 6 Hz: 2H); od 6.65 do 6.85 (mt: 3H); 6.91 (široko s: 1H); 7.15 (široko s: 1H); 7.37 (d, J = 3 Hz: 1H); 7.45 (dd, J = 9 i 3 Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.69 (s: 1H).
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-karboksilna kiselina je pripravljena u Primjeru 2.
Primjer 28
Natrijeva sol 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(cinamil)piperidin-4-karboksilne kiseline
Smjesa od 0.72 g etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(cinamil)piperidin-4-karboksilata u 14 cm3 dioksana, 14 cm3 metanola i 14 cm3 5N vodene otopine natrijeva hidroksida je miješana na temperaturi od 20°C. Nakon 2 sata, dodano je daljnjih 14 cm3 5N vodene otopine natrijeva hidroksida, a zatim još 14 cm3 nakon slijedećih 18 sati. Temperatura reakcijske smjese je održavana na 70°C tijekom 21 sata. Nakon hlađenja na 20°C reakcijska masa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen sa 15 cm3 destilirane vode, dilatriran, te sušen na zraku tijekom 18 sati. Dobiveno je 0.49 g natrijeve soli od natrijeve soli 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(cinamil)piperidin-4-karboksilne kiseline u obliku bijele krute tvari točke taljenja 230°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.16 (vrlo široki t, J = 12 Hz: 2H); od 1.45 do 1.70 (mt: 4H); od 1.95 do 2.20 (mt: 4H); od 2.45 do 2.60 (mt: 2H); 2.99 (d, J = 6.5 Hz: 2H); 3.14 (široki t, J = 7 Hz: 2H); 3.99 (s: 3H); 6.28 (dt, J = 15.5 i 6.5 Hz: 1H); 6.48 (d, J = 15.5 Hz: 1H); 7.24 (široki t, J = 7.5 Hz: 1H); 7.33 (široki t, J = 7.5 Hz: 2H); od 7.40 do 7.50 (mt: 4H); 7.95 (d, J = 9 Hz: 1H); 8.66 (s: 1H).
Etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(cinamil)piperidin-4-karboksilat
Smjesa od l g etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.551 g cinamilnog bromida, 0.42 g kalijeva jodida i 1.05 g kalijeva karbonata u 20 cm3 acetonitrila je miješana tijekom 18.5 sati na temperaturi od 20°C. Reakcijska smjesa je filtrirana, netopljivi materijal je ispran sa 20 cm3 acetonitrila, te sa 30 cm3 diklorometana. Filtrat je isušen na magnezijevom sulfatu, filtriran i koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod tlakom argona od 50 kPa, na stupcu silikagela (veličina čestice 40-63 μ; promjer 2.5 cm; masa 35 g), eluiranjem sa smjesom cikloheksan/etilni acetat (90/10 omjer volumena), a zatim sa smjesom cikloheksan/etilni acetat (60/40 omjer volumena) i sakupljanjem 20-cm3 frakcija. Frakcije koje sadrže produkt su kombinirane i koncentrirane do isušenja pod prethodno navedenim uvjetima. Dobiveno je 0.72 g etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(3-fenil-alil)piperidin-4-karboksilata u obliku viskoznog narančastog ulja.
Spektar mase: EI m/z = 406 M+
m/z = 415 C23H28ClN2O3+
m/z = 300 C19H26NO2+
m/z = 117 C9H9+ vršak baze
Etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilat je pripravljen u obliku monohidroklorida u Primjeru 5.
Primjer 29
4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-octena kiselina
Smjesa 0.18 g metil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-il}-karboksilata u 10 cm3 dioksana, 10 cm3 metanola i 0.99 cm3 vodene otopine natrijeva hidroksida je miješano na temperaturi od 75°C tijekom 17 sati. Nakon hlađenja na 45°C, reakcijska smjesa je koncentrirana do isušenja uz postupno sniženje tlaka do 9 kPa na temperaturi od 40°C. Pastozni ostatak je obrađen sa 3 cm3 kloroforma/metanola/vodene otopine amonijaka (12/3/0.5 omjer volumena), a organska faza je zatim pročišćena kromatografijom pod atmosferskim tlakom, na stupcu silikagela (Bond Elut; veličina čestice 70-200 μ; promjer 2 cm; masa 5 g), eluiranjem sa smjesnom kloroform/metanol/vodena otopina amonijaka (12/3/0.5 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C, a produkt je isušen u peći pod sniženim tlakom (50 kPa) na temperaturi od 50°C. Dobiveno je 0.15 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-octene kiseline.
1H NMR spektar (500 MHz, (CD3)2SO-d6, δ u ppm) : 1.39 (mt: 2H); 1.50 (mt: 2H); 1.61 (mt: 4H); 2.15 (široko s: 2H); od 2.30 do 2.60 (mt: 4H); 2.63 (široko t, J = 5.5 Hz: 2H); 3.12 (nedefinirani vršak: 2H); 3.94 (s: 3H); 4.06 (široko t, J = 5.5 Hz: 2H); od 6.65 do 6.75 (mt: 3H); 7.36 (široko s: 1H); 7.41 (široko d, J = 9 Hz: 1H); 7.93 (d, J = 9 Hz: 1H); 8.64 (s: 1H).
Metil {4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-il}acetat
Smjesa od 0.35 g metil {4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-il}acetata, 0.318 g 1-(2-bromoetoksi)-3,5-difluorobenzena, 0.15 g kalijeva jodida i 0.62 g kalijeva karbonata u u 20 cm3 acetonitrila je zagrijavana tijekom 18 sati na temperaturi od 70°C. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je filtrirana kroz silicijski umetak (Bond Elut), a zatim isprana s dva puta po 2 cm3 acetonitrila. Organska faza je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 45°C. Uparavanjem dobiveni ostatak je otopljen u 12 cm3 dimetilformamida, a zatim pročišćen injiciranjem 4 puta po 3 cm3 po kromatografiji na SCX silika-gelskom umetku (masa l g), eluiranjem sa gradijentom od čistog metanola do smjese 4N amonijskog metanola. Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod komprimiranim zrakom na temperaturi od 45°C. Uparavanjem dobiveni ostatak je obrađen diklorometanom, te sušen na zraku tijekom 48 sati, a potom sušen u pećnici pod sniženim tlakom (10 kPa) na temperaturi od 50°C. Dobiveno je 0.195 g metil {4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)etil]piperidin-4-il}acetata.
1H NMR spektar (500 MHz, (CD3)2SO-d6, na temperaturi od 353 K, δ u ppm): od 1.45 do 2.70 (mt: 16H); 3.17 (mt: 2H); 3.51 (mt: 3H); 3.96 (s: 3H); 4.24 (nedefinirani vršak: 2H); od 6.60 do 6.70 (mt: 3H); 7.38 (široko s: 1H); 7.42 (široko d, J = 9 Hz: 1H); 7.94 (d, J = 9 Hz: 1H); 8.62 (široko s: 1H).
Metil {4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-il}acetat
Smjesa od 17 g terc-butil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-4-cijanometilpiperidin-1-karboksilata u 100 cm3 vodene otopine 12N klorovodične kiseline (koncentrirana do isušenja) je postupno dovedena na temperaturu od 100°C uz miješanje tijekom 18 sati. Reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 60°C. Dobiveno ulje je obrađeno sa acetonom, a precipitat je filtracijom odvojen, te ispran acetonom. Dobiveno je 20.4 g {4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-il}octene kiseline dihidroklorida u obliku sivkaste krute tvari točke taljenja 181°C koja je postala ljepljiva. Gore navedeni produkt je otopljen u 400 cm3 metanola i 10 cm3 suho koncentrirane sulfatne kiseline, miješan i zagrijavan na temperaturu od 100°C tijekom 1.5 sati. Reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 50°C. Dobiveno ulje je obrađeno sa 300 cm3 vode uz miješanje, neutralizirano sa natrij hidrogen karbonatom, bazificirano sa kalijevim karbonatom i ekstrahirano sa etilnim acetatom. Organska faza je odvojena po završetku taloženja, isprana vodom, isušena na magnezijevom sulfatu, filtrirana i potom koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Vodena faza je postala bazična do pH vrijednosti od 8 dodatkom 5N vodene otopine natrijeva hidroksida i ekstrahiranjem sa etilnim acetatom, faze su razdvojene taloženjem, a organski ekstrakti su isprani, isušeni na magnezijevom sulfatu i koncentrirani do isušenja u skladu sa prethodno opisanim uvjetima. Svi ostaci nastali organskim uparavanjem su kombinirani i pročišćeni kromatografijom pod tlakom argona od 50 kPa, na stupcu silikagela (veličina čestice 20-43 μ; masa 200 g), eluiranjem sa smjesom diklorometan/metanol/vodena otopina amonijaka (40/5/0.5 omjer volumena). Frakcije koje sadrže produkt su kombinirane i koncentrirane do isušen ja kao što je opisano u prethodno navedenim uvjetima. Dobiveno je 7.6 g metil {4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-il}acetata u obliku narančasto obojenog ulja.
Spektar mase: EI m/z = 390 M+ m/z = 270 C11H10ClNO+
m/ z = 184 C10H18NO2+
terc-Butil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-4-cijanometilpiperidin-1-karboksilat
Smjesa od 30.58 g terc-butil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-4-metan-sulfoniloksimetil-piperidin-1-karboksilata i 15.1 g kalijeva cijanida u 436 cm3 dimetilnog sulfoksida je zagrijavana uz miješanje na temperaturi od 100°C tijekom 48 sati, a zatim je miješana na temperaturi od 20°C tijekom 24 sata. Dodano je 2 000 cm3 ledene vode u reakcijsku smjesu, nastala suspenzija je miješana tijekom l sata na temperaturi od 20°C, potom je filtrirana, a filtracijom dobivena masa je isprana sa 3 puta po 200 cm3 vode, te isušena na zraku. Ostatak je pročišćen kromatografijom pod tlakom argona od 50 kPa, na stupcu silikagela (veličina čestice 20-45 μ; promjer 9 cm; visina 45 cm), eluiranjem sa smjesom cikloheksan/etilni acetat (90/10 omjer volumena). Frakcije 40 do 100 su kombinirane i koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 45°C. Dobiveno je 19.25 g terc-butil 4-[3-(3-kloro-6-metoksikinolin-4-il) propil]-4-cijanometilpiperidin-1-karboksilata u obliku žute krute tvari točke taljenja 160°C.
Infra-crveni spektar (KBr) : 2968; 2924; 2235; 1684; 1622; 1505; 1414; 1230; 1166; 1151; 826 i 738 cm-1.
terc-Butil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-4-mβtansulfoniloksimetilpiperidin-1-karboksilat
Smjesa od 24.8 g terc-butil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-4-hidroksimetil-piperidin-1-karboksilata u 400 cm3 diklorometana i 12.9 cm3 trietilamina je ohlađena na približno 0°C uz miješanje u inertnoj atmosferi. Dodan je kap po kap metansulfonilni klorid prethodno otopljen u 125 cm3 diklorometana i reakcijska smjesa je miješana tijekom 18 sati na temperaturi od 20°C. Dodano je 200 cm3 vode u reakcijsku masu, potom je dalje dodano 3 000 cm3 vode. Faze su razdvojene taloženjem, a vodena faza je ekstrahirana sa 200 cm3 diklorometana. Organski ekstrakti su isprani sa 300 cm3 vodene otopine natrijeva klorida, isušeni na natrijevom sulfatu, filtrirani, a potom koncentrirani do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 45°C. Dobiveno je 30.6 g terc-butil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-4-metansulfoniloksimetilpiperidin-1-karboksilata u obliku narančasto obojenog ulja.
Spektar mase: DCI m/z = 507 MH+
m/z = 431 M-CH3SO3
m/z = 397 431-C1
m/z = 375 431-tBu
m/z = 331 431-BOC
1-(2-bromoetoksi)-3,5-difluorobenzen je pripravljen u Primjeru 16.
Terc-butil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-4-hidroksimetilpiperidin-1-karboksilat je pripravljen u Primjeru 19.
Primjer 30
{4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,5-difluorofenoksi)etil]piperidin-4-il}octβna kiselina
Smjesa 0.35 g metil {4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,5-difluorofenoksi)etil]piperidin-4-il}acetata u 10 cm3 dioksana, 10 cm3 metanola i 1.91 cm3 5N vodene otopine natrijeva hidroksida je miješana na temperaturi od 75°C tijekom 17 sati. Nakon hlađenja na 45°C, reakcijska smjesa je koncentrirana do isušenja uz postupno sniženje tlaka do 9 kPa na temperaturi od 40°C. Pastozni ostatak je obrađen sa 3 cm3 smjese kloroforma/metanola/vodene otopine amonijaka (12/3/0.5 omjer volumena), a organska faza je zatim pročišćena kromatografijom pod atmosferskim tlakom, na stupcu silikagela (Bond Elut; veličina čestice 70-200 μ; promjer 2 cm; masa 5 g), eluiranjem sa smjesnom kloroform/metanol/vodena otopina amonijaka (12/3/0.5 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C, a produkt je isušen u pećnici pod sniženim tlakom (50 kPa) na temperaturi od 50°C. Dobiveno je 0.27 g {4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,5-difluorofenoksi)etil]piperidin-4-iljoctene kiseline.
1H NMR spektar (500 MHz, (CD3)2SO-d6, δ u ppm) : 1.39 (mt: 2H); 1.50 (mt: 2H); 1.60 (mt: 4H); 2.15 (široko s: 2H); od 2.30 do 2.60 (mt: 4H); 2.67 (t, J = 6 Hz: 2H); 3.12 (nedefinirani vršak: 2H); 3.93 (s: 3H); 4.12 (t, J = 6 Hz: 2H); 6.72 (mt: 1H); 7.11 (mt: 1H); 7.21 (mt: 1H); 7.37 (široko s: 1H); 7.41 (široko d, J = 9 Hz: 1H); 7.93 (d, J = 9 Hz: 1H); 8.64 (s: 1H).
Metil {4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,5-difluorofenoksi)etil]piperidin-4-il}acetat
Smjesa od 0.35 g metil {4-[3-(3-kloro-6-metoksikinolin-4-il)propil]piperidin-4-il}acetata, 0.32 g 2-(2-bromoetoksi)-l,4-difluorobenzena, 0.15 g kalijeva jodida i 0.62 g kalijeva karbonata u 20 cm3 acetonitrila je miješana tijekom 18 sati na temperaturi od 70°C. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je filtrirana kroz silicijski umetak (Bond Elut), a zatim isprana s dva puta po 2 cm3 acetonitrila. Organska faza je koncentrirana do isušenja pod sniženim tlakom (2.4 kPa) na temperaturi od 45°C. Uparavanjem dobiveni ostatak je otopljen u 12 cm3 dimetilformamida, a zatim pročišćen injiciranjem 4 puta po 3 cm3 po kromatografiji na SCX silika-gelskom umetku (masa l g), eluiranjem sa gradijentom od čistog metanola do smjese 4N amonijskog metanola. Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod komprimiranim zrakom na temperaturi od 45°C. Uparavanjem dobiveni ostatak je obrađen diklorometanom, te sušen na zraku tijekom 48 sati, a potom sušen u pećnici pod sniženim tlakom (10 kPa) na temperaturi od 50°C. Dobiveno je 0.38 g metil {4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(2,5-difluorofenoksi)etil]piperidin-4-il}acetata.
1H NMR spektar (500 MHz, (CD3)2SO-d6, δ u ppm) : od 1.30 do 1.65 (mt: 8H); 2.25 (široko s: 2H); od 2.30 do 2.60 (mt: 4H); 2.69 (mt: 2H); 3.14 (mt: 2H); 3.47 (široko s: 3H); 3.95 (široko s: 3H); 4.12 (mt: 2H); 6.72 (mt: 1H); 7.11 (mt: 1H); 7.21 (mt: 1H); 7.38 (široko s: 1H); 7.43 (široko d, J = 9 Hz: 1H); 7.94 (široko d, J = 9 Hz: 1H); 8.66 (široko s: 1H).
2-(2-bromoetoksi)-l,4-difluorobenzen je pripravljen u Primjeru 16.
Metil {4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-piperidin-4-il}acetat je pripravljen u Primjeru 29.
Primjer 31
1-(2-Ciklopentiltioetil)-4-[3-(3-fluoro-6-xnetoksikinolin-4-il)propil]piperidin-4-karboksilna kiselina
Smjesa 0.4 g etil 1-(2-ciklopentiltioetil)-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata u 3 cm3 dioksana, 3 cm3 metanola i 2.4 cm3 5N otopine natrijeva hidroksida je miješana na temperaturi od 70°C tijekom 17 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja uz postupno sniženje tlaka od 30 do 2.5 kPa na temperaturi od 45°C. Ostatak je obrađen sa 5 cm3 smjese diklorometana/metanola/vodene otopine amonijaka (40/5/0.5 omjer volumena), a zatim je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 10 g), eluiranjem sa smjesnom diklorometan/metanol/vodena otopina amonijaka (40/5/0.5 omjer volumena), a potom sa smjesom kloroforma/ metanola/vodene otopine amonijaka (13/3/0.5). Frakcije koje sadržavaju precipitat su kombinirane, filtrirane, a zatim isprane metanolom. Dobivena kruta tvar je rekristalizirana iz 15 cm3 uzavrelog metanola, ohlađena, filtrirana, isprana metnolom i osušena u pećnici pod sniženim tlakom (10 kPa) na temperaturi od 20°C. Filtracijske tekućine su kombinirane i koncentrirane do isušenja pod sniženim tlakom(2 kPa) na temperaturi od 40°C. Tekućine, jedanput koncentrirane do isušenja, te prethodno dobivena kruta tvar su kombinirani do nastanka 0.179 g 1-(2-ciklopentiltioetil)-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilne kiseline u obliku bijele krute tvari.
1H NMR spektar (400 MHz, (CD3)2SO-d6, uz dodatak nekoliko kapi CF3COOD, δ u ppm): 1.41 (mt: 2H); od 1.50 do 1.75 (mt: 8H); od 1.90 do 2.05 (mt: 4H); 2.20 (široko d, J = 14 Hz: 2H); od 2.75 do 2.90 (mt: 4H); od 3.10 do 3.25 (mt: 1H); 3.16 (t, J = 7 Hz: 2H); 3.29 (mt: 2H); 3.50 (široko d, J = 14 Hz: 2H) ; 3.99 (s: 3H); 7.47 (d, J = 2.5 Hz: 1H); 7.55 (dd, J = 9 i 2.5 Hz: 1H); 8.06 (d, J = 9 Hz: 1H); 8.98 (široko s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilat
Smjesa od 0.5 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.253 g (2-kloroetiltio)-ciklopentana, 0.25 g kalijeva jodida i 0.92 g kalijeva karbonata u 15 cm3 acetonitrila je miješana tijekom 18 sati na temperaturi od 70°C. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je filtrirana, a zatim isprana s dva puta po 3 cm3 acetonitrila. Organska faza je koncentrirana do isušenja pod sniženim tlakom (2.4 kPa) na temperaturi od 45°C. Uparavanjem dobiveni ostatak je otopljen u smjesi etilnog acetata/40-60°C petrolejskog etera (8/2 omjer volumena), a zatim pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 10 g), eluiranjem sa smjesom etilnog acetata/40-60°C petrolejskog etera (8/2 omjer volumena). Frakcije 5 i 14 su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 0.43 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata.
1H NMR spektar (500 MHz, (CD3)2SO-d6, δ u ppm) : 0.98 (t, J = 7 Hz: 3H); 1.36 (mt: 4H); od 1.40 do 1.70 (mt: 8H); od 1.80 do 2.00 (mt: 6H); od 2.30 do 2.65 (mt: 6H); 3.02 (mt: 2H); 3.09 (mt: 1H); 3.92 (s: 3H); 3.94 (q, J = 7 Hz: 2H); 7.31 (široko s: 1H); 7.37 (široko d, J = 9 Hz: 1H); 7.94 (d, J = 9 Hz: 1H); 8.66 (široko s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat je pripravljen u Primjeru 11.
Primjer 32
1-(2-Cikloheksiletil)-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilna kiselina
Smjesa 0.2 g etil 1-(2-cikloheksiletil)-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata u 3 cm3 dioksana, 3 cm3 metanola i 1.2 cm3 5N otopine natrijeva hidroksida je miješana na temperaturi od 70°C tijekom 22 sata. Nakon hlađenja na približno 20°C, reakcijska smjesa je uparena uz postupno sniženje tlaka od 30 do 2.5 kPa na temperaturi od 45°C. Ostatak je obrađen sa 5 cm3 smjese diklorometana/ metanola/vodene otopine amonijaka (40/5/0.5 omjer volumena), a zatim je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 10 g), eluiranjem sa smjesnom diklorometan/metanol/vodena otopina amonijaka (40/5/0.5 omjer volumena), a potom sa smjesom kloroforma/metanola/vodene otopine amonijaka (13/3/0.5). Frakcije koje sadržavaju produkt su kombinirane, koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C, te isušene u sušilici (10 kPa). Dobiveno je 0.14 g 1-(2-cikloheksiletil)-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilne kiseline u obliku bijele krute tvari.
1H NMR spektar (400 MHz, (CD3)2SO-d6, uz dodatak nekoliko kapi CF3COOD, δ u ppm): od 0.80 do 1.00 (mt: 2H); od 1.05 do 1.35 (mt: 5H); od 1.40 do 1.75 (mt: 12H); 2.19 (široko d, J = 14 Hz: 2H); 2.78 (široko t, J = 12.5 Hz: 2H); 3.07 (mt: 2H) ; 3.20 (široko t, J = 6.5 Hz: 2H); 3.45 (široko d, J = 12.5 Hz: 2H); 4.00 (s: 3H); 7.52 (d, J = 2.5 Hz: 1H); 7.60 (dd, J = 9 i 2.5 Hz: 1H); 8.10 (d, J = 9 Hz: 1H); 9.10 (d, J = 2 Hz: 1H).
Etil 1-(2-cikloheksiletil)-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilat
Smjesa od 0.4 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.245 g l-bromo-2-cikloheksiletana, 0.18 g kalijeva jodida i 0.737 g kalijeva karbonata u 15 cm3 acetonitrila je miješana tijekom 18 sati na temperaturi od 70°C. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 12 g), eluiranjem sa smjesom etilnog acetata/40-60°C petrolejskog etera (8/2 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 0.23 g etil 1-(2-cikloheksiletil)-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata.
1H NMR spektar (500 MHz, (CD3)2SO-d6, δ u ppm) : 0.84 (mt: 2H); 0.98 (t, J = 7 Hz: 3H); od 1.00 do 2.65 (mt: 25H); 3.02 (mt: 2H); 3.93 (s: 3H); 3.95 (q, J = 7 Hz: 2H); 7.31 (široko s: 1H); 7.35 (široko d, J = 9 Hz: 1H); 7.94 (d, J = 9 Hz: 1H); 8.67 (široko s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat je pripravljen u Primjeru 11.
Primjer 33
1-(2-Cikloheksiltioetil)-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilna kiselina
Smjesa 0.3 g etil 1-(2-cikloheksiltioetil)-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata u 3 cm3 dioksana, 3 cm3 metanola i 1.7 cm3 5N vodene otopine natrijeva hidroksida je miješana na temperaturi od 70°C tijekom 17 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja uz postupno sniženje tlaka od 30 do 2.5 kPa na temperaturi od 45°C. Ostatak je obrađen sa 5 cm3 smjese diklorometana/ metanola/vodene otopine amonijaka (40/5/0.5 omjer volumena), a zatim je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 10 g), eluiranjem sa smjesnom diklorometan/metanol/vodena otopina amonijaka (40/5/0.5 omjer volumena), a potom sa smjesom kloroforma/ metanola/vodene otopine amonijaka (13/3/0.5). Frakcije koje sadržavaju produkt su kombinirane, koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C, te isušene u sušilici (10 kPa). Dobiveno je 0.25 g 1-(2-cikloheksil-tioetil)-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilne kiseline u obliku bijele krute tvari.
1H NMR spektar (400 MHz, (CD3)2SO-d6, uz dodatak nekoliko kapi CF3COOD, δ u ppm): od 1.15 do 1.35 (mt: 5H); od 1.50 do 1.75 (mt: 8H); od 1.80 do 2.05 (mt: 3H); 2.20 (široko d, J = 14 Hz: 2H); od 2.65 do 2.90 (mt: 5H); 3.20 (široko t, J = 7 Hz: 2H) ; 3.25 (mt: 2H); 3.50 (široko d, J = 12 Hz: 2H); 4.00 (s: 3H); 7.50 (d, J = 2.5 Hz: 1H); 7.59 (dd, J = 9 i 2.5 Hz: 1H); 8.09 (d, J = 9 Hz: 1H); 9.07 (d, J = 2.5 Hz: 1H).
Etil 1-(2-cikloheksiltioetil)-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilat
Smjesa od 0.4 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.23 g 2-kloroetiltio-cikloheksana, 0.18 g kalijeva jodida i 0.74 g kalijeva karbonata u 15 cm3 acetonitrila je miješana tijekom 18 sati na temperaturi od 70°C. Nakon hlađenja na temperaturu od 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 12 g), eluiranjem sa smjesom etilnog acetata/40-60°C petrolejskog etera (8/2 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 0.32 g etil 1-(2-cikloheksiletil)-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata.
1H NMR spektar (500 MHz, (CD3)2SO-d6, δ u ppm) : 0.97 (t, J = 7 Hz: 3H); od 1.05 do 1.70 (mt: 14H); od 1.75 do 2.00 (mt: 6H); od 2.25 do 2.60 (mt: 6H); 2.62 (mt: 1H); 3.01 (mt: 2H) ; 3.91 (s: 3H); 3.94 (q, J = 7 Hz: 2H); 7.30 (široko s: 1H); 7.37 (široko d, J = 9 Hz: 1H); 7.93 (d, J = 9 Hz: 1H); 8.66 (široko s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat je pripravljen u Primjeru 11.
Primjer 34
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)piperidin-4-karboksilna kiselina
Smjesa 0.1 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)-piperidin-4-karboksilata u 3 cm3 dioksana, 3 cm3 metanola i 0.6 cm3 5N vodene otopine natrijeva hidroksida je miješana na temperaturi od 70°C tijekom 17 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja uz postupno sniženje tlaka od 30 do 2.5 kPa na temperaturi od 45°C. Ostatak je obrađen sa 5 cm3 smjese diklorometana/metanola/vodene otopine amonijaka (40/5/0.5 omjer volumena), a zatim je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 10 g), eluiranjem sa smjesnom diklorometan/metanol/vodena otopina amonijaka (40/5/0.5 omjer volumena), a potom sa smjesom kloroforma/-metanola/vodene otopine amonijaka (13/3/0.5). Frakcije koje sadržavaju produkt su kombinirane, koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C, te isušene u sušilici (10 kPa). Dobiveno je 0.25 g 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)-piperidin-4-karboksilne kiseline u obliku bijele krute tvari.
1H NMR spektar (400 MHz, (CD3)2SO-d6, uz dodatak nekoliko kapi CF3COOD, δ u ppm): od 1.50 do 1.75 (mt: 6H); od 1.85 do 2.05 (mt: 2H); 2.19 (široko d, J = 14 Hz: 2H); 2.60 (t, J = 7.5 Hz: 2H); 2.81 (široko d, J = 12.5 Hz: 2H); 3.07 (mt: 2H); 3.20 (široko t, J = 7.5 Hz: 2H); 3.47 (široko d, J = 12.5 Hz: 2H); 3.99 (s: 3H); od 7.15 do 7.35 (mt: 5H); 7.51 (d, J = 2.5 Hz: 1H); 7.59 (dd, J = 9 i 2.5 Hz: 1H); 8.10 (d, J = 9 Hz: 1H) ; 9.08 (d, J = 2 Hz: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)piperidin-4-karboksilat
Smjesa od 0.4 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.25 g l-bromo-3-fenilpropana, 0.181 g kalijeva jodida i 0.74 g kalijeva karbonata u 15 cm3 acetonitrila je miješana tijekom 18 sati na temperaturi od 70°C. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 12 g), eluiranjem sa smjesom etilnog acetata/40-60°C petrolejskog etera (8/2 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 0.1 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)piperidin-4-karboksilata.
1H NMR spektar (500 MHz, (CD3)2SO-d6, δ u ppm) : 0.97 (t, J = 7 Hz: 3H); od 1.25 do 2.00 (mt: 12H); od 2.25 do 2.70 (mt: 6H); 3.01 (mt: 2H); 3.91 (s: 3H); 3.94 (široki q, J = 7 Hz: 2H); 7.15 (mt: 3H); 7.24 (široki t, J = 7.5 Hz: 2H); 7.30 (široko s: 1H); 7.36 (široko d, J = 9 Hz: 1H); 7.93 (d, J = 9 Hz: 1H); 8.66 (široko s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat je pripravljen u Primjeru 11.
Primjer 35
1-[2-(2,5-Difluorofeniltio)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilna kiselina
Smjesa 0.26 g etil 1-[2-(2,5-difluorofeniltio)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata u 3 cm3 dioksana, 3 cm3 metanola i 1.4 cm3 5N vodene otopine natrijeva hidroksida je miješana na temperaturi od 70°C tijekom 17 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja uz postupno sniženje tlaka od 30 do 2.5 kPa na temperaturi od 45°C. Ostatak je obrađen sa 5 cm3 smjese diklorometana/metanola/vodene otopine amonijaka (40/5/0.5 omjer volumena), a zatim je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 10 g), eluiranjem sa smjesom diklorometan/metanol/vodena otopina amonijaka (90/9/0.9 omjer volumena), a potom sa smjesom kloroforma/-metanola/vodene otopine amonijaka (77.5/19.5/3). Frakcije koje sadržavaju produkt su kombinirane, koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C, te isušene u sušilici (10 kPa). Dobiveno je 0.3 g 1-[2-(2,5-difluoro-feniltio)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilne kiseline u obliku bijele krute tvari.
1H NMR spektar (400 MHz, (CD3)2SO-d6, uz dodatak nekoliko kapi CF3COOD, δ u ppm): od 1.50 do 1.75 (mt: 6H); 2.21 (široko d, J = 14 Hz: 2H); 2.89 (široko t, J = 12.5 Hz: 2H); 3.16 (mt: 2H); od 3.25 do 3.50 (mt: 4H); 3.54 (široko d, J = 12.5 Hz: 2H); 3.99 (s: 3H); 7.14 (mt: 1H); 7.30 (udvostručeni triplet, J = 9 i 5 Hz: 1H); 7.39 (mt: 1H); 7.47 (d, J = 2.5 Hz: 1H); 7.54 (dd, J = 9 i 2.5 Hz: 1H); 8.07 (d, J = 9 Hz: 1H); 8.97 (d, J = 2 Hz: 1H).
Etil 1-[2-(2,5-difluorofeniltio)etil]-4-[3-(3-fluoro-6-xnetoksikinolin-4-il)propil]piperidin-4-karboksilat
Smjesa od 0.4 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.324 g 2-(2-bromoetiltio)-l,4-difluorobenzena, 0.181 g kalijeva jodida i 0.74 g kalijeva karbonata u 15 cm3 acetonitrila je miješana tijekom 18 sati na temperaturi od 70°C. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C.
Uparavanjem dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 12 g), eluiranjem sa smjesom etilnog acetata/40-60°C petrolejskog etera (8/2 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 0.27 g etil 1-[2-(2,5-difluorofeniltio)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata.
1H NMR spektar (500 MHz, (CD3)2SO-d6, δ u ppm) : 0.97 (t, J = 7 Hz: 3H); 1.31 (široko t, J = 11 Hz: 2H); od 1.40 do 2.00 (mt: 4H); od 1.80 do 2.00 (mt: 4H); od 2.35 do 2.70 (mt: 4H); 3.01 (mt: 2H); 3.07 (široki t, J = 7 Hz: 2H); 3.91 (s: 3H); 3.94 (q, J = 7 Hz: 2H); 7.00 (mt: 2H); 7.21 (mt: 1H); 7.26 (mt: 1H); 7.30 (široko s: 1H); 7.37 (široko d, J = 9 Hz: 1H); 7.93 (d, J = 9 Hz: 1H); 8.66 (široko s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat je pripravljen u Primjeru 11.
1-(2-Bromoetiltio)-2,5-difluorobenzen je pripravljen u Primjeru 14.
Primjer 36
1-[2-(2,5-Difluorofenoksi)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilna kiselina
Smjesa 0.38 g etil 1-[2-(2,5-difluorofenoksi)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata u 3 cm3 dioksana, 3 cm3 metanola i 2.1 cm3 5N vodene otopine natrijeva hidroksida je miješana na temperaturi od 70°C tijekom 17 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja uz postupno sniženje tlaka od 30 do 2.5 kPa na temperaturi od 45°C. Ostatak je obrađen sa 5 cm3 smjese diklorometana/metanola/-vodene otopine amonijaka (40/5/0.5 omjer volumena), a zatim je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 10 g), eluiranjem sa smjesnom diklorometan/metanol/vodena otopina amonijaka (90/9/0.9 omjer volumena), a potom sa smjesom kloroforma/metanola/vodene otopine amonijaka (77.5/19.5/3). Frakcije koje sadržavaju produkt su kombinirane, koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C, te isušene u sušilici (10 kPa). Dobiveno je 0.36 g 1-[2-(2,5-difluorofenoksi)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilne kiseline u obliku bijele krute tvari.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.32 (široko t, J = 13 Hz: 2H); od 1.50 do 1.70 (mt: 4H); 1.96 (široko d, J = 13 Hz: 2H); 2.09 (široko t, J = 11.5 Hz: 2H); 2.64 (t, J = 6 Hz: 2H); 2.70 (široko d, J = 11.5 Hz: 2H) ; 3.05 (vrlo široko t, J = 6.5 Hz: 2H); 3.96 (s: 3H) ; 4.13 (t, J = 6 Hz: 2H); 6.75 (mt: 1H); 7.14 (mt: 1H); 7.24 (mt: 1H); 7.34 (d, J = 2.5 Hz: 1H); 7.41 (dd, J = 9 i 2.5 Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.69 (široko s: 1H).
Etil 1-[2-(2,5-difluorofenoksi)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilat
Smjesa od 0.4 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.30 g 2-(2-bromoetoksi)-l,4-difluorobenzena, 0.181 g kalijeva jodida i 0.74 g kalijeva karbonata u 15 cm3 acetonitrila je miješana tijekom 18 sati na temperaturi od 70°C. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 12 g), eluiranjem sa smjesom etilnog acetata/40-60°C petrolejskog etera (8/2 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 0.4 g etil 1-[2-(2,5-difluorofenoksi)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata.
1H NMR spektar (500 MHz, (CD3)2SO-d6, δ u ppm) : 0.97 (t, J = 7 Hz: 3H); 1.36 (široko t, J = 11.5 Hz: 2H); od 1.40 do 1.60 (mt: 4H); od 1.80 do 2.10 (mt: 4H); 2.61 (široki t, J = 5.5 Hz: 2H); 2.69 (široko d, J = 11 Hz: 2H); 3.02 (mt: 2H); 3.92 (s: 3H); 3.94 (q, J = 7 Hz: 2H); 4.09 (mt: 2H); 6.71 (mt: 1H); 7.10 (mt: 1H); 7.19 (mt: 1H); 7.29 (široko s: 1H); 7.37 (široko d, J = 9 Hz: 1H); 7.93 (d, J = 9 Hz: 1H); 8.66 (široko s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat je pripravljen u Primjeru 11.
2-(2-Bromoetoksi)-l,4-difluorobenzen je pripravljen u Primjeru 16.
Primjer 37
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-karboksilna kiselina
Smjesa 0.42 g 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2, 3, 5-trifluorofenoksi)etil]piperidin-4-karboksilata u 3 cm3 dioksana, 3 cm3 metanola i 2.3 cm3 5N vodene otopine natrijeva hidroksida je miješana na temperaturi od 70°C tijekom 17 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja uz postupno sniženje tlaka od 30 do 2.5 kPa na temperaturi od 45°C. Ostatak je obrađen sa 5 cm3 smjese diklorometana/metanola/-vodene otopine amonijaka (40/5/0.5 omjer volumena), a zatim je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 10 g), eluiranjem sa smjesnom diklorometan/metanol/vodena otopina amonijaka (90/9/0.9 omjer volumena), a zatim sa smjesom kloroforma/metanola/vodene otopine amonijaka (77.5/19.5/3). Frakcije koje sadržavaju produkt su kombinirane, koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C, te isušene u sušilici (10 kPa). Dobiveno je 0.39 g 4-[3-(3-fluoro-6-metoksikinolin-4-il) propil]-1-[2-(2,3,5-trifluorofenoksi)etil] piperidin-4-karboksilne kiseline u obliku bijele krute tvari.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.32 (vrlo široki t, J = 12.5 Hz: 2H) ; 1.60 (mt: 4H) ; 1.95 (široko d, J = 12.5 Hz: 2H) ; 2.09 (široko t, J = 11 Hz: 2H) ; 2.64 (t, J = 5.5 Hz: 2H) ; 2.70 (široko d, J = 11 Hz: 2H) ; 3.04 (vrlo široki t, J = 6 Hz: 2H) ; 3.96 (s: 3H) ; 4.16 (t, J = 5.5 Hz: 2H) ; od 6.95 do 7.15 (mt: 2H) ; 7.34 (d, J = 2.5 Hz: 1H); 7.40 (dd, J = 9 i 2.5 Hz: 1H); 7.96 (d, J = 9 Hz: 1H); 8.69 (široki s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,3,5-trifluorofenoksi)etil]piperidin-4-karboksilat
Smjesa od 0.4 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.33 g 1-(2-bromoetoksi)-2,3,5-trifluorobenzena, 0.181 g kalijeva jodida i 0.74 g kalijeva karbonata u 15 cm3 acetonitrila je miješana tijekom 18 sati na temperaturi od 70°C. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 12 g; volumen 25 cm3), eluiranjem sa smjesom etilnog acetata/40-60°C petrolejskog etera (8/2 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 0.43 g etil 4-[3- (3-fluoro-6-metoksikinolin-4-il)propil] -1- [2- (2, 3, 5-trifluorofenoksi) -etil] piperidin-4-karboksilata.
1H NMR spektar (500 MHz, (CD3)2SO-d6, δ u ppm) : 0.98 (t, J = 7 Hz: 3H) ; 1.34 (široko t, J = 11.5 Hz: 2H) ; od 1.45 do 1.60 (mt: 4H) ; od 1.80 do 2.10 (mt: 4H) ; od 2.50 do 2.70 (mt: 4H) ; 3.02 (mt: 2H) ; 3.92 (s: 3H) ; 3.94 (q, J = 7 Hz: 2H) ; 4.14 (mt : 2H) ; 7.02 (mt: 2H) ; 7.30 (široko s: 1H); 7.37 (široko d, J = 9 Hz: 1H); 7.94 (d, J = 9 Hz: 1H); 8.66 (široko s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat je pripravljen u Primjeru 11.
1-(2-Bromoetoksi) -2, 3, 5-trifluorobenzen je pripravljen kao što je opisano u Primjeru 13.
Primjer 38
4-[3-(3-Fluoro-6-metoksikinolin-4-il) propil] -1-heptilpiperidin-4-karboksilna kiselina
Smjesa 0.16 g 4-[3- (3-fluoro-6-metoksikinolin-4-il)propil] -1-heptilpiperidin-4-karboksilata, u 3 cm3 dioksana, 3 cm3 metanola i l cm3 5N vodene otopine natrijeva hidroksida je miješana na temperaturi od 70°C tijekom 17 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja uz postupno sniženje tlaka od 30 do 2.5 kPa na temperaturi od 45 °C. Ostatak je obrađen sa 5 cm3 smjese diklorometana/metanola/vodene otopine amonijaka (40/5/0.5 omjer volumena), a zatim je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 10 g), eluiranjem sa smjesnom diklorometan/metanol/vodena otopina amonijaka (40/5/0.5 omjer volumena), a zatim sa smjesom kloroforma/metanola/vodene otopine amonijaka (13/3/0.5). Frakcije koje sadržavaju produkt su kombinirane, koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C, te isušene u sušilici (10 kPa). Dobiveno je 0.07 g 4-[3-(3-fluoro-6-metoksikinolin-4-il) propil]-1-heptilpiperidin-4-karboksilne kiseline u obliku bijele krute tvari.
1H NMR spektar (400 MHz, (CD3)2SO-d6, uz dodatak nekoliko kapi CF3COOD, δ u ppm): 0.85 (t, J = 7 Hz: 3H); od 1.15 do 1.35 (mt: 8H); od 1.50 do 1.75 (mt: 8H); 2.19 (široko d, J = 14 Hz: 2H); 2.78 (široko t, J = 11 Hz: 2H); 2.64 (t, J = 5.5 Hz: 2H); 2.70 (široko d, J = 12.5 Hz: 2H); 3.02 (mt: 2H); 3.19 (široki t, J = 7 Hz: 2H); 3.45 (široko d, J = 12.5 Hz: 2H); 4.00 (s: 3H); 7.50 (d, J = 2.5 Hz: 1H); 7.58 (dd, J = 9 i 2.5 Hz: 1H); 8.09 (d, J = 9 Hz: 1H); 9.04 (d, J - 2 Hz: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-heptilpiperidin-4-karboksilat
Smjesa od 0.4 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.23 g 1-bromoheptana, 0.18 g kalijeva jodida i 0.737 g kalijeva karbonata u 15 cm3 acetonitrila je miješana tijekom 18 sati na temperaturi od 70°C. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (veličina čestice 70-200 μ; masa 12 g), eluiranjem sa smjesom etilnog acetata/40-60°C petrolejskog etera (8/2 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 0.2 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-heptilpiperidin-4-karboksilata.
1H NMR spektar (500 MHz, (CD3)2SO-d6, δ u ppm): 0.84 (t, J = 7 Hz: 3H); 0.98 (t, J = 7 Hz: 3H); od 1.10 do 1.30 (mt: 8H); 1.33 (mt: 4H); od 1.40 do 1.60 (mt: 4H); 1.83 (široki t, J = 11 Hz: 2H); 1.93 (široko d, J = 13 Hz: 2H); 2.13 (mt: 2H); od 2.35 do 2.55 (mt: 2H); 3.01 (mt: 2H); 3.89 (s: 3H); 3.94 (mt: 2H); 7.31 (široko s: 1H); 7.37 (široko d, J = 9 Hz: 1H); 7.94 (d, J = 9 Hz: 1H); 8.67 (široko s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat je pripravljen u Primjeru 11.
Primjer 39
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-(2-feniltioetil)piperidin-4-karboksilna kiselina
Smjesa 0.39 g 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(2-feniltioetil)piperidin-4-karboksilata u 3 cm3 dioksana, 3 cm3 metanola i 2.3 cm3 5N vodene otopine natrijeva hidroksida je miješana na temperaturi od 70°C tijekom 17 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja uz postupno sniženje tlaka od 30 do 2.5 kPa na temperaturi od 45°C. Ostatak je obrađen sa 5 cm3 smjese diklorometana/metanola/vodene otopine amonijaka (40/5/0.5 omjer volumena), a zatim je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 10 g), eluiranjem sa smjesnom diklorometan/metanol/vodena otopina amonijaka (90/9/0.9 omjer volumena), a zatim sa smjesom kloroforma/-metanola/vodene otopine amonijaka (77.5/19.5/3). Frakcije koje sadržavaju produkt su kombinirane, koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C, te isušene u sušilici (10 kPa). Dobiveno je 0.3 g 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(2-feniltioetil)piperidin-4-karboksilne kiseline u obliku bijele krute tvari.
1H NMR spektar (400 MHz, (CD3)2SO-d6, uz dodatak nekoliko kapi CF3COOD, δ u ppm): od 1.50 do 1.75 (mt: 6H); 2.20 (široko d, J = 14 Hz: 2H); 2.87 (široko t, J = 13 Hz: 2H); 3.16 (mt: 2H); 3.41 (s: 4H); 3.53 (široko d, J = 13 Hz: 2H); 4.00 (s: 3H); 7.25 (široki t, J = 7.5 Hz: 1H); od 7.30 do 7.45 (mt: 4H); 7.48 (d, J = 2.5 Hz: 1H); 7.54 (dd, J = 9 i 2.5 Hz: 1H); 8.07 (d, J = 9 Hz: 1H); 8.97 (d, J = 2Hz: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(2-feniltioetil)piperidin-4-karboksilat
Smjesa od 0.4 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.28 g 2-bromoetil fenil sulfida, 0.181 g kalijeva jodida i 0.74 g kalijeva karbonata u 15 cm3 acetonitrila je miješana tijekom 18 sati na temperaturi od 70°C. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 12 g), eluiranjem sa smjesom etilnog acetata/40-60°C petrolejskog etera (8/2 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 0.4 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(2-feniltioetil]-piperidin-4-karboksilata.
1H NMR spektar (500 MHz, (CD3)2SO-d6, δ u ppm) : 0.97 (t, J = 7 Hz: 3H); 1.33 (široko t, J = 12.5 Hz: 2H); od 1.45 do 1.65 (mt: 4H); od 1.85 do 2.00 (mt: 4H); od 2.30 do 2.70 (mt: 4H) ; 3.01 (mt: 2H); 3.92 (s: 3H); 3.94 (mt: 2H); 7.15 (mt: 1H); od 7.20 do 7.35 (mt: 5H); 7.37 (široko d, J = 9 Hz: 1H); 8.66 (široko s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat je pripravljen u Primjeru 11.
Primjer 40
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3-fluorofeniltio)etil]piperidin-4-karboksilna kiselina
Smjesa 0.2 g 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(2-feniltioetil)piperidin-4-karboksilata u 3 cm3 dioksana, 3 cm3 metanola i 1.1 cm3 5N vodene otopine natrijeva hidroksida je miješana na temperaturi od 70°C tijekom 17 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja uz postupno sniženje tlaka od 30 do 2.5 kPa na temperaturi od 45°C. Ostatak je obrađen sa 5 cm3 smjese diklorometana/metanola/vodene otopine amonijaka (40/5/0.5 omjer volumena), a zatim je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 10 g), eluiranjem sa smjesnom diklorometan/metanol/vodena otopina amonijaka (90/9/0.9 omjer volumena), a zatim sa smjesom kloroforma/metanola/vodene otopine amonijaka (77.5/19.5/3). Frakcije koje sadržavaju produkt su kombinirane, koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C, te isušene u sušilici (10 kPa). Dobiveno je 0.18 g 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3-fluorofeniltio)etil]piperidin-4-karboksilne kiseline.
1H NMR spektar (400 MHz, (CD3)2SO-d6, uz dodatak nekoliko kapi CF3COOD, δ u ppm): od 1.50 do 1.75 (mt: 6H); 2.20 (široko d, J = 14 Hz: 2H); 2.89 (široko t, J = 12.5 Hz: 2H) ; 3.18 (mt: 2H); od 3.25 do 3.45 (mt: 4H); 3.54 (široko d, J = 12.5 Hz: 2H); 3.99 (s: 3H); 7.05 (udvostručeni triplet, J = 9 i 2.5 Hz: 1H); od 7.15 do 7.30 (mt: 2H); 7.38 (mt: 1H); 7.48 (d, J = 2.5 Hz: 1H); 7.55 (dd, J = 9 i 2.5 Hz: 1H); 8.08 (d, J = 9 Hz: 1H); 9.00 (d, J = 2 Hz: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(2-feniltioetil)piperidin-4-karboksilat
Smjesa od 0.4 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.30 g 3-fluoro-2-bromoetil fenil sulfida, 0.18 g kalijeva jodida i 0.74 g kalijeva karbonata u 15 cm3 acetonitrila je miješana tijekom 18 sati na temperaturi od 70°C. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je pročišćen kromatografijom pod tlakom argona, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 12 g), eluiranjem sa smjesom etilnog acetata/40-60°C petrolejskog etera (8/2 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 0.22 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(2-feniltioetil)piperidin-4-karboksilata.
1H NMR spektar (500 MHz, (CD3)2SO-d6, δ u ppm) : 0.98 (t, J = 7 Hz: 3H); 1.33 (široko t, J = 12 Hz: 2H); od 1.45 do 1.65 (mt: 4H); od 1.85 do 2.00 (mt: 4H); od 2.30 do 2.70 (mt: 4H); 3.02 (mt: 2H); 3.07 (t, J= 6.5 Hz: 2H); 3.92 (s: 3H); 3.94 (q, J = 7 Hz: 2H); 6.94 (široki t, J = 8.5 Hz: 1H); od 7.05 do 7.20 (mt: 2H); od 7.25 do 7.35 (mt: 2H); 7.37 (široki d, J = 9 Hz: 1H); 7.94 (d, J = 9 Hz: 1H); 8.66 (široko s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat je pripravljen u Primjeru 11.
3-Fluoro-6-bromoetil fenil sulfid je pripravljen u skladu s postupkom opisanim u Primjeru 14.
Primjer 41
1-[2-(3,4-Difluorofenoksi)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilna kiselina
Smjesa 0.38 g etil 1-[2-(3,4-difluorofenoksi)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata u 3 cm3 dioksana, 3 cm3 metanola i 2.1 cm3 5N vodene otopine natrijeva hidroksida je miješana na temperaturi od 70°C tijekom 17 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja uz postupno sniženje tlaka od 30 do 2.5 kPa na temperaturi od 45°C. Ostatak je obrađen sa 5 cm3 smjese diklorometana/metanola/-vodene otopine amonijaka (40/5/0.5 omjer volumena), a zatim je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 10 g), eluiranjem sa smjesnom diklorometan/metanol/vodena otopina amonijaka (90/9/0.9 omjer volumena), a zatim sa smjesom kloroforma/metanola/vodene otopine amonijaka (77.5/19.5/3). Frakcije koje sadržavaju produkt su kombinirane, koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C, te isušene u sušilici (10 kPa). Dobiveno je 0.3 g 1-[2-(3,4-difluorofenoksi)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilne kiseline u obliku bijele krute tvari.
1H NMR spektar (400 MHz, (CD3)2SO-d6, uz dodatak nekoliko kapi CF3COOD, δ u ppm): od 1.50 do 1.75 (mt: 6H); 2.21 (široko d, J = 14 Hz: 2H); 2.96 (široko t, J = 13 Hz: 2H); 3.19 (široki t, J= 6.5 Hz: 2H); od 3.50 do 3.65 (mt: 4H); 4.00 (s: 3H); 4.31 (t, J = 5.5 Hz: 2H); 6.82 (mt: 1H); 7.11 (mt: 1H); 7.35 (mt: 1H); 7.50 (d, J = 2.5 Hz: 1H); 7.57 (dd, J = 9 i 2.5 Hz: 1H); 8.09 (d, J = 9 Hz: 1H); 9.03 (d, J = 2 Hz: 1H).
Etil 1-[2-(3,4-difluorofenoksi)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilat
Smjesa od 0.4 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.3 g 4-(2-bromoetoksi)-1,2-difluorobenzena, 0.18 g kalijeva jodida i 0.74 g kalijeva karbonata u 15 cm3 acetonitrila je miješana tijekom 18 sati na temperaturi od 70°C. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 12 g), eluiranjem sa smjesom etilnog acetata/40-60°C petrolejskog etera (8/2 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 0.4 g etil 1-[2-(3,4-difluorofenoksi)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata.
1H NMR spektar (500 MHz, (CD3)2SO-d6, δ u ppm) : 0.98 (t, J = 7 Hz: 3H); 1.36 (široko t, J = 12 Hz: 2H); od 1.45 do 1.65 (mt: 4H); 1.93 (široko d, J = 12 Hz: 2H); 2.00 (široki t, J = 11.5 Hz: 2H); od 2.40 do 2.70 (mt: 4H); 3.02 (mt: 2H); 3.92 (s: 3H); 3.94 (q, J = 7 Hz: 2H); 3.99 (mt: 2H); 6.73 (mt: 2H); 7.03 (mt: 1H); od 7.25 do 7.35 (mt: 2H); 7.37 (široki d, J = 9 Hz: 1H); 7.93 (d, J = 9 Hz: 1H); 8.66 (široko s: 1H).
4-(2-Bromoetoksi)-1,2-difluorobenzen
Smjesa 15 g 3,4-difluorofenola, 23.5 g kalijeva karbonata i 60 cm3 1,2-dibromoetana u 250 cm3 acetonitrila je miješana na temperaturi od 70°C tijekom 18 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je filtrirana kroz dijatomejsku zemlju (Celit), a zatim koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 70-200 μ; promjer 8 cm; masa 400 g), eluiranjem sa 40-60°C petrolejskog etera. Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 15.7 g 4-(2-bromoetoksi)-1,2-difluorobenzena u obliku ulja.
Infra-crveni spektar (CCl4) : 1609; 1516; 1264; 1253; 1215; 1206; 1162; 1019; 854 i 834 cm-1.
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat je pripravljen u Primjeru 11.
Primjer 42
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3-fluorofeniltio)etil]piperidin-4-karboksilna kiselina
Smjesa 0.39 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(2-fenoksietil)piperidin-4-karboksilata u 3 cm3 dioksana, 3 cm3 metanola i 2.4 cm3 5N vodene otopine natrijeva hidroksida je miješana na temperaturi od 70°C tijekom 17 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja uz postupno sniženje tlaka od 30 do 2.5 kPa na temperaturi od 45°C. Ostatak je obrađen sa 5 cm3 smjese diklorometana/metanola/vodene otopine amonijaka (40/5/0.5 omjer volumena), a zatim je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 10 g), eluiranjem sa smjesnom diklorometan/metanol/vodena otopina amonijaka (90/9/0.9 omjer volumena), a zatim sa smjesom kloroforma/-metanola/vodene otopine amonijaka (77.5/19.5/3). Frakcije koje sadržavaju produkt su kombinirane, koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C, te isušene u sušilici (10 kPa). Dobiveno je 0.33 g 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(2-fenoksietil)piperidin-4-karboksilne kiseline u obliku bijele krute tvari.
1H NMR spektar (300 MHz, (CD3)2SO-d6, uz dodatak nekoliko kapi CF3COOD, δ u ppm): 1.36 (široko t, J = 12.5 Hz: 2H); od 1.50 do 1.70 (mt: 4H); 1.96 (široko d, J = 12.5 Hz: 2H); 2.08 (široko t, J = 11.5 Hz: 2H); 2.62 (t, J = 6 Hz: 2H); 2.71 (široko d, J = 11.5 Hz: 2H); 3.05 (široko t, J = 6.5 Hz: 2H); 3.97 (s: 3H); 4.03 (t, J = 6 Hz: 2H); od 6.85 do 7.00 (mt: 3H); 7.29 (široko t, J = 8 Hz: 2H); 7.35 (d, J = 2.5 Hz: 1H); 7.40 (dd, J = 9 i 2.5 Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.70 (široko s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(2-fenoksietil)piperidin-4-karboksilat
Smjesa od 0.4 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.26 g 2-bromoetil fenil etera, 0.181 g kalijeva jodida i 0.737 g kalijeva karbonata u 15 cm3 acetonitrila je miješana tijekom 18 sati na temperaturi od 70°C. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 12 g), eluiranjem sa smjesom etilnog acetata/40-60°C petrolejskog etera (8/2 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 0.4 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(2-fenoksietil)piperidin-4-karboksilata.
1H NMR spektar (500 MHz, (CD3)2SO-d6, δ u ppm) : 0.99 (t, J = 7 Hz: 3H); 1.37 (mt: 2H); od 1.45 do 1.65 (mt: 4H); od 1.85 do 2.10 (mt: 4H); od 2.35 do 2.75 (mt: 4H); 3.03 (mt: 2H); 3.93 (s: 3H); 3.96 (q, J = 7 Hz: 2H); 4.02 (mt: 2H); 6.90 (mt: 3H); 7.26 (široki t, J = 7.5 Hz: 2H); 7.32 (široko s: 1H); 7.38 (široko d, J = 9 Hz: 1H); 7.95 (d, J = 9 Hz: 1H); 8.68 (široko s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat je pripravljen u Primjeru 11.
Primjer 43
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3-fluorofenoksi)etil]piperidin-4-karboksilna kiselina
Smjesa 0.415 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3-fluorofenoksi)etil]piperidin-4-karboksilata u 3 cm3 dioksana, 3 cm3 metanola i 2.4 cm3 5N vodene otopine natrijeva hidroksida je miješana na temperaturi od 70°C tijekom 17 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja uz postupno sniženje tlaka od 30 do 2.5 kPa na temperaturi od 45°C. Ostatak je obrađen sa 5 cm3 smjese diklorometana/metanola/vodene otopine amonijaka (40/5/0.5 omjer volumena), a zatim je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 10 g), eluiranjem sa smjesnom diklorometan/metanol/vodena otopina amonijaka (90/9/0.9 omjer volumena), a zatim sa smjesom kloroforma/-metanola/vodene otopine amonijaka (77.5/19.5/3). Frakcije koje sadržavaju produkt su kombinirane, koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C, te isušene u sušilici (10 kPa). Dobiveno je 0.34 g 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3-fluorofenoksi)-etil]piperidin-4-karboksilne kiseline u obliku bijele krute tvari.
1H NMR spektar (300 MHz, (CD3)2SO-d6, uz dodatak nekoliko kapi CF3COOD, δ u ppm): 1.34 (široko t, J = 12.5 Hz: 2H) ; od 1.50 do 1.70 (mt: 4H); 1.96 (široko d, J = 12.5 Hz: 2H); 2.08 (široko t, J = 11 Hz: 2H); 2.63 (t, J = 6 Hz: 2H); 2.70 (široko d, J = 11 Hz: 2H); 3.05 (široko t, J = 6.5 Hz: 2H); 3.97 (s: 3H); 4.06 (t, J = 6 Hz: 2H); od 6.70 do 6.90 (mt: 3H); od 7.25 do 7.40 (mt: 1H); 7.35 (d, J = 2.5 Hz: 1H); 7.40 (dd, J = 9 i 2.5 Hz: 1H); 7,97 (d, J = 9 Hz: 1H); 8.70 (široko s: 1H).
Etil 4-[3-(3-f luoro-6-xnetoksikinolin-4-il)propil]-1-[2-(3-fluorofenoksi)etil]piperidin-4-karboksilat
Smjesa od 0.4 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.281 g 1-(2-bromoetoksi)-3-fluorobenzena, 0.181 g kalijeva jodida i 0.737 g kalijeva karbonata u 15 cm3 acetonitrila je miješana tijekom 18 sati na temperaturi od 70°C. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 12 g), eluiranjem sa smjesom etilnog acetata/40-60°C petrolejskog etera (8/2 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 0.43 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3-fluorofenoksi)etil]piperidin-4-karboksilata.
1H NMR spektar (500 MHz, (CD3)2SO-d6, δ u ppm) : 0.98 (t, J = 7 Hz: 3H); 1.35 (široki t, J = 12 Hz: 2H) ; od 1.45 do 1.65 (rat: 4H); 1.92 (široko d, J = 12 Hz: 2H); 2.00 (široko t, J = 11.5 Hz: 2H); od 2.30 do 2.70 (mt: 4H); 3.91 (s: 3H); 3.94 (q, J = 7 Hz: 2H); 4.01 (mt: 2H); od 6.65 do 6.80 (mt: 3H); od 7.20 do 7.30 (mt: 1H); 7.28 (široko s: 1H); 7.36 (široko d, J = 9 Hz: 1H); 7.93 (d, J = 9 Hz: 1H); 8.65 (široko s: 1H).
1-(2-Bromoetoksi)-3-fluorobenzen
Smjesa 8.6 g 3-fluorofenola, 15.3 g kalijeva karbonata i 40.5 cm3 l,2-dibromoetana u 200 cm3 acetonitrila je miješana u inertnoj atmosferi, na temperaturi od 70°C tijekom 25 sati. Nakon hlađenja na približno 20°C, suspenzija je filtrirana, a netopljivi materijal je ispran sa 3 puta po 50 cm3 acetonitrila i filtrat je zatim koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen sa 50 cm3 dietilnog etera, potom filtriran, a filtracijom dobivene tekućine su koncentrirane do isušenja pod prethodno navedenim uvjetima. Uparavanjem dobiveno ulje je pročišćeno kromatografijom pod tlakom argona od 50 kPa, na stupcu silikagela (veličina čestice 20-45 μ; promjer 4.5 cm; visina 22 cm), eluiranjem sa 40-60°C petrolejskog etera. Frakcije 8 do 60 su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 7.67 g 1-(2-bromoetoksi)-3-fluorobenzena.
Infra-crveni spektar (CCl4) : 1616; 1596; 1492; 1279; 1265; 1168; 1140; 1025; 853 i 679 cm-1.
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat je pripravljen u Primjeru 11.
Primjer 44
1-[2-(2,6-Difluorofenoksi)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilna kiselina
Smjesa 0.39 g etil 1-[2-(2,6-difluorofenoksi)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata u 3 cm3 dioksana, 3 cm3 metanola i 2.2 cm3 5N vodene otopine natrijeva hidroksida je miješana na temperaturi od 70°C tijekom 17 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja uz postupno sniženje tlaka od 30 do 2.5 kPa na temperaturi od 45°C. Ostatak je obrađen sa 5 cm3 smjese diklorometana/metanola/-vodene otopine amonijaka (40/5/0.5 omjer volumena), a zatim je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 10 g), eluiranjem sa smjesnom diklorometan/metanol/vodena otopina amonijaka (90/9/0.9 omjer volumena), a zatim sa smjesom kloroforma/metanola/vodene otopine amonijaka (77.5/19.5/3). Frakcije koje sadržavaju produkt su kombinirane, koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C, te isušene u sušilici (10 kPa). Dobiveno je 0.3 g 1-[2-(2,6-difluorofenoksi)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilne kiseline u obliku bijele krute tvari.
1H NMR spektar (400 MHz, (CD3)2SO-d6, δ u ppm) : 1.33 (široki t, J = 12.5 Hz: 2H); od 1.50 do 1.65 (mt: 4H); 1.91 (široko d, J = 12.5 Hz: 2H); 2.05 (široko t, J = 11 Hz: 2H); 2.60 (t, J= 6 Hz: 2H); 2.63 (mt: 2H); 3.05 (mt: 2H); 3.97 (s: 3H); 4.16 (t, J = 6 Hz: 2H); od 7.05 do 7.20 (mt: 3H); 7.35 (d, J = 2.5 Hz: 1H); 7.40 (dd, J = 9 i 2.5 Hz: 1H); 7.97 (d, J - 9 Hz: 1H); 8.70 (široko s: 1H).
Etil 1-[2-(2,6-difluorofenoksi)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilat
Smjesa od 0.4 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.304 g 1-(2-bromoetoksi)-3-fluorobenzena, 0.181 g kalijeva jodida i 0.74 g kalijeva karbonata u 15 cm3 acetonitrila je miješana tijekom 18 sati na temperaturi od 70°C. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 12 g), eluiranjem sa smjesom etilnog acetata/40-60°C petrolejskog etera (8/2 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 0.4 g etil 1-[2-(2,6-difluorofenoksi)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata.
1H NMR spektar (500 MHz, (CD3)2SO-d6, δ u ppm) : 0.97 (t, J = 7 Hz: 3H); 1.26 (široko t, J = 125 Hz: 2H); od 1.40 do 1.60 (mt: 4H); 1.88 (široko d, J = 12 Hz: 2H); 1.98 (široki t, J = 11 Hz: 2H); od 2.30 do 2.65 (mt: 4H); 3.00 (mt: 2H); 3.92 (s: 3H); 3.94 (mt: 2H); 4.11 (mt: 2H); od 6.95 do 7.10 (mt: 3H); 7.30 (široko s: 1H); 7.37 (široki d, J = 9 Hz: 1H); 7.93 (d, J = 9 Hz: 1H); 8.66 (široko s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat je pripravljen u Primjeru 11.
1-(2-bromoetoksi)-3-fluorobenzen je pripravljen u skladu s postupkom opisanim u Primjeru 15.
Primjer 45
1-[2-(2,3-Difluorofenoksi)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilna kiselina
Smjesa 0.42 g etil 1-[2-(2,3-difluorofenoksi)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata u 3 cm3 dioksana, 3 cm3 metanola i 2.4 cm3 5N vodene otopine natrijeva hidroksida je miješana na temperaturi od 70°C tijekom 17 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja uz postupno sniženje tlaka od 30 do 2.5 kPa na temperaturi od 45°C. Ostatak je obrađen sa 5 cm3 smjese diklorometana/metanola/-vodene otopine amonijaka (40/5/0.5 omjer volumena), a zatim je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 10 g), eluiranjem sa smjesnom diklorometan/metanol/vodena otopina amonijaka (90/9/0.9 omjer volumena), a zatim sa smjesom kloroforma/metanola/vodene otopine amonijaka (77.5/19.5/3). Frakcije koje sadržavaju produkt su kombinirane, koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C, te isušene u sušilici (10 kPa). Dobiveno je 0.32 g 1-[2-(2,3-difluorofenoksi)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilne kiseline u obliku bijele krute tvari.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.34 (široki t, J = 12.5 Hz: 2H); od 1.50 do 1.70 (mt: 4H); 1.96 (široko d, J = 12.5 Hz: 2H); 2.09 (široki t, J = 11.5 Hz: 2H); 2.65 (t, J= 6 Hz: 2H); 2.71 (široki d, J = 11.5 Hz: 2H); 3.05 (mt: 2H); 3.97 (s: 3H); 4.16 (t, J = 6 Hz: 2H); od 6.90 do 7.20 (mt: 3H); 7.34 (d, J = 2.5 Hz: 1H); 7.40 (dd, J = 9 i 2.5 Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.70 (široko s: 1H).
Etil 1-[2-(2,3-difluorofenoksi)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilat
Smjesa od 0.4 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata, 0.3 g 1-(2-bromoetoksi)-2,3-difluorobenzena, 0.181 g kalijeva jodida i 0.74 g kalijeva karbonata u 15 cm3 acetonitrila je miješana tijekom 18 sati na temperaturi od 70°C. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (5 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na umetku silikagela (Bond Elut; veličina čestice 70-200 μ; masa 12 g), eluiranjem sa smjesom etilnog acetata/40-60°C petrolejskog etera (8/2 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 0.43 g etil 1-[2-(2,3-difluorofenoksi)etil]-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilata.
1H NMR spektar (500 MHz, (CD3)2SO-d6, δ u ppm) : 0.99 (mt: 3H); 1.34 (mt: 2H); od 1.40 do 1.60 (mt: 4H); 1.93 (široko d, J = 12.5 Hz: 2H); od 1.95 do 2.10 (mt: 2H); od 2.45 do 2.70 (mt: 4H); 3.02 (mt: 2H); 3.93 (s: 3H); 3.95 (mt: 2H); 4.12 (mt: 2H); od 6.85 do 7.05 (mt: 2H); 7.09 (mt: 1H); 7.37 (široki d, J = 9 Hz: 1H); 7.94 (d, J = 9 Hz: 1H); 8.66 (široko s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat je pripravljen u Primjeru 11.
1-(2-Bromoetoksi)-2,3-difluorobenzen je pripravljen u Primjeru 17.
Primjer 46
4-[3-(3-Fluorokinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilna kiselina
Smjesa 1.29 g etil 4-[3-(3-fluorokinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilata u 65 cm3 dioksana, 65 cm3 metanola i 8 cm3 5N vodene otopine natrijeva hidroksida je miješana na temperaturi od 70°C tijekom 20 sati. 8 cm3 5N vodene otopine natrijeva hidroksida je dodano u reakcijsku smjesu, koja je miješana na 70°C tijekom daljnjih 6 sati. Nakon hlađenja na približno 20°C, reakcijska masa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 50°C. Ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 20-45 μ; promjer 6 cm; visina 30 cm), eluiranjem sa smjesom kloroforma/metanola/vodene otopine amonijaka (12/3/0.5 omjera volumena) i sakupljanjem 100-cm3 frakcija. Frakcije 8 do 24 su kombinirane i koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Bijela kruta tvar je obrađena sa 60 cm3 diizopropilnog etera i miješana tijekom 18 sati na temperaturi od 20°C. Suspenzija je filtrirana, isprana sa 3 puta po 15 cm3 diizopropilnog etera, filtrirana centrifugom i zatim isušena pod sniženim tlakom (10 kPa) na približno 50°C. Dobiveno je 0.8 g 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilne kiseline u obliku bijele krute tvari točke taljenja 180°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.27 (mt: 2H); 1.56 (mt: 4H); od 1.85 do 2.05 (mt: 4H); 2.44 (široko t, J = 7 Hz: 2H); 2.57 (mt: 2H); 2.90 (široko t, J = 7 Hz: 2H); 3.06 (nedefinirani vršak: 2H); 7.04 (dd, J = 5.5 i 3.5 Hz: 1H); 7.17 (dd, J = 3.5 i 1.5 Hz: 1H); 7.60 (dd, J = 5.5 i 1.5 Hz: 1H); 7.71 (široki t, J = 7.5 Hz: 1H); 7.77 (široki t, J = 7.5 Hz: 1H); 8.08 (široki d, J = 7.5 Hz: 1H); 8.15 (široki d, J = 7.5 Hz: 1H); 8.89 (d, J = 1.5 Hz: 1H).
Etil 4-[3-(3-fluorokinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilat
Smjesa od 1.8 g etil 1-(2-kloroetil)-4-[3-(3-fluoro-kinolin-4-il)propil]piperidin-4-karboksilatnog monohidroklorida, 0.48 cm3 tiofen-2-tiola, 2.8 g kalijeva karbonata i 0.75 g kalijeva jodida u 200 cm3 anhidroznog acetonitrila je miješana u inertnoj atmosferi tijekom 18 sati na temperaturi od 70°C, suspenzija je filtrirana, isprana sa 3 puta po 30 cm3 acetonitrila, a filtrat je zatim koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 50°C. Uparavanjem dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 20-45 μ; promjer 6 cm; visina 30 cm), eluiranjem sa etilnim acetatom i sakupljanjem 50-cm3 frakcija. Frakcije 25 do 52 su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 1.3 g etil 4-[3-(3-fluorokinolin-4-il)propil]-1-[2-(tiofen-2-iltio)etil]piperidin-4-karboksilata u obliku viskoznog narančasto obojenog ulja.
1H NMR spektar (500 MHz, (CD3)2SO-d6, δ u ppm) : 0.99 (t, J = 7 Hz: 3H); 1.34 (vrlo široki t, J = 13 Hz: 2H); od 1.85 do 2.00 (mt: 4H); 2.45 (široki t, J = 7 Hz: 2H); 2.59 (široko d, J = 11.5 Hz: 2H); od 2.90 (široki t, J = 7 Hz: 2H); 3.07 (široki t, J = 6.5 Hz: 2H; 3.95 (q, J = 7 Hz: 2H); 7.04 (dd, J = 5.5 i 3.5 Hz: 1H); 7.17 (dd, J = 3.5 i 1.5 Hz: 1H); 7.60 (dd, J = 5.5 i 1.5 Hz: 1H); 7.70 (široki t, J = 7.5 Hz: 1H); 7.77 (dvostruki triplet, J = 7.5 i 1.5 Hz: 1H); 8.08 (široko d, J = 7.5 Hz: 1H); 8.13 (široko d, J = 7.5 Hz: 1H); 8.89 (d, J = iHz: 1H).
Etil 1-(2-kloroetil)-4-[3-(3-fluorokinolin-4-il)propil]-piperidin-4-karboksilatni hidroklorid
1.2 cm3 tionilnog klorida u 5 cm3 diklorometana je dodano otopini od 1.55 g etil 4-[3-(3-fluorokinolin-4-il)propil]-1-(2-hidroksi-etil)piperidin-4-karboksilata u 35 cm3 diklorometana uz miješanje na temperaturi od 20°C. Nakon miješanja tijekom 42 sata na temperaturi od 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (1.2 kPa) na približno 50°C. Dobivena pjena je obrađena sa 3 puta po 100 cm3 cikloheksana, koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C, te isušena u pećnici pod sniženim tlakom (10 kPa) na temperaturi od 20°C. Dobivno je 1.8 g 1-(2-kloroetil)-4-[3-(3-fluorokinolin-4-il)propil]-piperidin-4-karboksilatnog monohidroklorida u obliku bež obojene krute tvari.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.03 (t, J = 7 Hz: 3H); od 1.45 do 2.10 (mt: 6H); 2.16 (široko d, J = 14 Hz: 2H); od 2.70 do 3.00 (mt: 2H); 3.12 (mt: 2H); od 3.40 do 3.55 (mt: 4H); od 3.95 do 4.10 (mt: 4H); 7.72 (široko t, J = 7.5 Hz: 1H); 7.79 (široki t, J = 7.5 Hz: 1H); 8.09 (široko d, J = 7.5 Hz: 1H); 8.18 (široko d, J = 7.5 Hz: 1H); 8.92 (široko s: 1H); od 10.10 do 10.35 (nedefinirani vršak: 1H).
Etil 4-[3-(3-fluorokinolin-4-il)propil]-1-(2-hidroksi-etil)piperidin-4-karboksilat
1.14 cm3 2-jodoetanola i 1.9 g kalijeva karbonata je dodano otopini od 4.4 g etilnog 4-[3-(3-fluorokinolin-4-il)propil]piperidin-4-karboksilata u 100 cm3 anhidroznog acetonitrila, uz snažno miješanje u inertnoj atmosferi. Reakcijska smjesa je miješana tijekom 18 sati na temperaturi od 20°C, filtrirana i isprana sa 3 puta po 30 cm3 acetonitrila. Filtrat je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 50°C. Uparavanjem dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 20 do 45 μ; promjer 5 cm; visina 32 cm), eluiranjem sa smjesom diklorometana/-metanola/vodene otopine amonijaka (40/5/0.5 omjer volumena) i sakupljanjem 100-cm3 frakcija. Frakcije 8 do 12 su kombinirane, a potom koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 3.5 g etilnog 4-[3-(3-fluorokinolin-4-il)propil]-1-(2-hidroksi-etil)piperidin-4-karboksilata u obliku viskoznog narančasto obojenog ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm): 0.99 (t, J = 7 Hz: 3H); 1.36 (mt: 2H); 1.57 (mt: 4H); od 1.85 do 2.05 (mt: 4H); 2.29 (t, J = 6.5 Hz: 2H); 2.61 (d mt, J = 12 Hz: 2H); 3.08 (široki t, J = 6 Hz: 2H; 3.45 (mt: 2H); 3.96 (q, J = 7 Hz: 2H); 4.31 (t, J = 5.5 Hz: 1H); 7.70 (široki t, J = 7.5 Hz: 1H); 7.77 (dvostruki triplet, J = 7.5 i 1.5 Hz: 1H); 8.08 (dd, J = 7.5 i 1.5 Hz: 1H); 8.14 (dd, J = 7.5 i 1.5 Hz: 1H); 8.89 (d, J = 1Hz: 1H).
Etil 4-[3-(3-fluorokinolin-4-il)propil]piperidin-4-karboksilat
50 cm3 otopine klorovodika u dioksanu u koncentraciji od 4M je oprezno dodano u otopinu od 8.7 g etil 4-[3-(3-fluorokinolin-4-il)propil]-1-(terc-butiloksikarbonil)-piperidin-4-karboksilata u 150 cm3 anhidroznog dioksana, uz održavanje temperature ispod 30°C tijekom dodavanja. Nakon miješanja tijekom 18 sati na temperaturi od 20°C, suspenzija je razrijeđena sa 250 cm3 dietilnog etera, filtrirana i isprana sa 5 puta po 50 cm3 dietilnog etera, a kruta tvar je isušena u sušilici pod sniženim tlakom (2 kPa) na temperaturi od 20°C. Kruta tvar je obrađena sa 50 cm3 vode i dodano je 5N vodene otopine natrijeva hidroksida kako bi se postigla vrijednost pH od približno 10, a smjesa je zatim ekstrahirana sa 5 puta po 100 cm3 dietilnog etera. Organske faze su kombinirane, isušene na magnezijevom sulfatu, obrađene sa drvenim ugljenom (3S), filtrirane i koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 50°C. Dobiveno je 4.7 g etilnog 4-[3-(3-fluorokinolin-4-il)propil]piperidin-4-karboksilata u obliku viskoznog narančasto obojenog ulja.
Spektar mase: EI m/z = 344 M+ m/z = 288 C17H19FNO2+
m/z = 184 C10H18NO2+
vršak baze m/z = 161 C10H8FN+
Etil 4-[3-(3-fluorokinolin-4-il)propil]-1-(terc-butiloksikarbonil) piperidin-4-karboksilat
17.7 g etil 4-alil-1-(terc-butiloksikarbonil)piperidin-4-karboksilata u 200 cm3 tetrahidrofurana je ohlađeno na temperaturu od -30°C i dodano je 135 cm3 0.5M otopine 9-borabiciklo[3.3.l]nonana u tetrahidrofuranu uz miješanje u inertnoj atmosferi. Po završetku dodavanja, temperatura smjese je vraćena na 20°C i smjesa je miješana tijekom 2 sata. Dodano je 14.8 g 3-fluoro-4-jodokinolina u 430 cm3 tetrahidrofurana, 1.3 g paladij difenilfosfinoferocenskog klorida i 29.8 g trobazičnog kalijevog fosfata. Reakcijska smjesa je zatim zagrijavana na temperaturi od 70°C tijekom 20 sati. Nakon hlađenja na temperaturu od 20°C, reakcijska masa je filtrirana i isprana sa 3 puta po 100 cm3 tetrahidrofurana. Filtrat je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je obrađen sa 500 cm3 dietilnog etera, netopljivi materijal je ispran sa 3 puta po 100 cm3 dietilnog etera, a filtrat je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je ulje pročišćeno kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 20-45 μ: promjer 6 cm; visina 45 cm), eluiranjem sa smjesom diklorometan/etilni acetat (90/10 omjer volumena) i sakupljanjem 120-cm3 frakcija. Frakcije 30 do 76 su kombinirane, a zatim koncentrirane do isušenja pod identičnim uvjetima kao što je prethodno navedeno. Dobiveno je 13.7 g etilnog 4-[3-(3-fluorokinolin-4-il)propil]-1-(terc-butiloksikarbonil)piperidin-4-karboksilata u obliku viskoznog narančasto obojenog ulja.
Spektar mase: EI m/z = 444 M+ m/z = 388 [M - tBu]+
m/z = 343 [M - BOC]+
m/z = 288 Ci7H19FNO2+ m/z = 184 C10H18NO2+-
m/z = 161 C10H8FN+ m/z = 57 C4H9+
5-fluoro-4-jodokinolin
17.3 cm3 diizopropilamina u 650 cm3 tetrahidrofurana je ohlađeno na temperaturu od -75°C i dodano je 76 cm3 1.6M otopine butil litija u heksanu uz miješanje u inertnoj atmosferi, te odražavanjem temperature na približno -70°C. Nakon miješanja tijekom 20 minuta na temperaturi od -75°C, dodana je otopina od 11.9 g 3-fluorokinolina u 200 cm3 tetrahidrofurana. Dobivena otopina je miješana tijekom daljnja 4 sata na -75°C, potom je dodana otopina od 32.2 g dvostruko sublimiranog joda u 150 cm3 tetrahidrofurana. Nakon miješanja tijekom 2 sata na temperaturi od -40°C, reakcijska smjesa je hidrolizirana sa 200 cm3 smjese tetrahidrofurana/vode (90/10 omjer volumena), a zatim sa 200 cm3 zasićene otopine natrijeva klorida. Na temperaturi od 20°C, smjesa je razrijeđena sa 300 cm3 etilnog acetata i isprana sa dva puta 250 cm3 zasićene otopine natrijeva klorida. Organska faza je isušena magnezijevim sulfatom, filtrirana i koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 50°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 20-45 μ: promjer 10 cm; visina 30 cm), eluiranjem sa diklorometanom i sakupljanjem 120-cm3 frakcija. Frakcije 45 do 80 su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 15.1 g 3-fluro-4-jodokinolina u obliku krem obojene krute tvari točke taljenja 110°C.
Spektar mase: EI m/z = 273 M+, vršak baze m/z = 146 [M - I]+
3-Fluorokinolin
23.5 g 3-aminokinolina i 12.1 g natrijeva nitrita u 20 cm3 destilirane vode je dodano oprezno u 100 cm3 tetrafluoro-borične kiseline ohlađene na 0°C, uz snažno miješanje, a reakcijska smjesa je zatim miješana tijekom 30 minuta. Suspenzija je filtrirana, centrifugiranjem filtrirana, isprana sa 3 puta po 30 cm3 ledeno-hladne tetrafluoroborične kiseline, 50 cm3 ledeno-hladnog etanola i 4 puta po 30 cm3 dietilnog etera. Kruta tvar je isušena u sušilici (2 kPa) na temperaturi od 20°C, a zatim obrađena sa 200 cm3 toluena i zagrijavana na temperaturi od 90°C tijekom l sata uz miješanje. Nakon hlađenja na 20°C, faze reakcijske mase su razdvojene taloženjem, a netopljivo ulje je isprano sa 3 puta po 100 cm3 toluena i obrađeno sa 110 cm3 vode, te bazificirano dodatkom natrijeva hidrogen karbonata do postizanja pH vrijednosti 8. Vodena faza je ekstrahirana sa 5 puta po 100 cm3 dietilnog etera, a organske faze su kombinirane, isprane sa dva puta po 50 cm3 vode, isušene na magnezijevom sulfatu i obrađene sa drvenim ugljenom (3S), filtrirane i koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 45°C. Ulje je obrađeno sa 50 cm3 smjese 40-60°C petrolejskog etera/etilnog acetata (90/10 omjer volumena), a netopljivi materijal je filtracijom odvojen, ispran sa dva puta po 25 cm3 40-60°C smjese petrolejskog etera/etilnog acetata (90/10 omjer volumena) i isušen u sušilici pod sniženim tlakom (2 kPa) na temperaturi od 20°C. Filtrat je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 20-45 μ: promjer 5 cm; visina 45 cm), eluiranjem sa smjesom 40-60°C petrolejskog etera/etilnog acetata (90/10 omjer volumena) i sakupljanjem 100-cm3 frakcija. Frakcije 20 do 31 su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 13 g 3-flurokinolina u obliku bezbojne tekućine.
Spektar mase: EI m/z = 147 M+ vršak baze m/z = 127 [M - HF]+
m/z = 120 [M - HCN]+
Etil 4-alil-1-(terc-butoksikarbonil)-piperidin-4-karboksilat je pripravljen u Primjeru 1.
Primjer 47
Etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(piridin-2-iloksi)etil]piperidin-4-karboksilat je pripravljen u obliku viskoznog bezbojnog ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.04 (t, J = 7 Hz: 3H); 1.39 (vrlo široki t, J = 12 Hz: 2H); 1.51 (mt: 2H); 1.68 (mt: 2H); od 1.90 do 2.15 (mt: 4H); 2.60 (t, J = 6 Hz: 2H); 2.70 (široko d, J = 12 HZ: 2HI); 3.16 (široki t, J = 7.5 Hz: 2H); 3.95 (s: 3H); 3.99 (q, J = 7 Hz: 2H); 4.31 (t, J = 6 Hz: 2H); 6.78 (d, J = 8 Hz: 1H); 6.96 (široko dd, J = 7.5 i 5 Hz: 1H); 7.37 (d, J = 2.5 Hz: 1H); 7.45 (dd, J = 9 i 2.5 Hz: 1H); 7.69 (ddd, J = 8-7.5 i 2 Hz: 1H); 7.96 (d, J = 9 Hz: 1H); 8.14 (široko dd, J = 5 i 2 Hz: 1H); 8.67 (s: 1H).
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-[2-(piridin-2-iloksi)etil]piperidin-4-karboksilna kiselina
Smjesa 0.12 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(piridin-2-iloksi)etil]piperidin-4-karboksilata u 5 cm3 dioksana, 5 cm3 metanola i l cm3 5N vodene otopine natrijeva hidroksida je miješana na temperaturi od 70°C tijekom 21 sata. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja uz sniženi tlak (5 kPa) na temperaturi od 60°C. Ostatak je obrađen sa 5 cm3 smjese diklorometana/metanola/vodene otopine amonijaka (40/5/0.5 omjer volumena), a zatim je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 70-200 μ; promjer 1.5 cm; masa 20 g), eluiranjem sa smjesnom diklorometan/metanol/vodena otopina amonijaka (40/5/0.5 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Pjena je obrađena sa 2 cm3 metanola, filtrirana, isprana sa l cm3 metanola i 2 cm3 dietilnog etera, a zatim isušena u pećnici pod sniženim tlakom (10 kPa), na temperaturi od približno 50°C. Dobiveno je 0.115 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(piridin-2-iloksi)etil]piperidin-4-karboksilne kiseline u obliku bijele krute tvari, točke taljenja 70°C koja je postala ljepljivom.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.20 do 1.80 (mt: 6H); 1.98 (vrlo široko d, J = 13.5 Hz: 2H); 2.09 (vrlo široki t, J = 11 Hz: 2H); 2.60 (t, J = 6 Hz: 2H); 2.67 (mt: 2H); 3.16 (mt: 2H); 3.98 (s: 3H); 4.32 (t, J = 6 Hz: 2H); 6.80 (d, J = 8 Hz: 1H); 6.96 (ddd, J = 7.5 - 5 i l Hz: 1H); 7.39 (široko s: 1H); 7.45 (dd, J = 9 i 2.5 Hz: 1H); 7.70 (ddd, J = 8-7.5 i 2 Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.16 (široko dd, J = 5 i 2 Hz: 1H); 8.67 (s: 1H).
Primjer 48
4-[3-(3-Kloro-6-metoksikinolin-4-il)-3-(R,S)-fluoropropil]-1-[2-(2,5-difluorofeniltio)etil]piperidin-4-karboksilna kiselina
Smjesa 0.07 g metil 4-[3-(3-fluoro-6-metoksikinolin-4-il)-3-(R,S)-fluoropropil]-1-[2-(2,5-difluorofeniltio)etil]-piperidin-4-karboksilata u 3 cm3 dioksana, 3 cm3 metanola i 0.9 cm3 5N vodene otopine natrijeva hidroksida je održavana na temperaturi od 70°C tijekom 4 sata. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Ostatak je kromatografiran pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 70-200 μ; masa 10 g), eluiranjem sa smjesnom diklorometan/metanol/vodena otopina amonijaka (40/5/0.5 omjer volumena). Frakcije 10 do 15 su kombinirane, a zatim koncentrirane do isušenja pod prethodno navedenim uvjetima. Dobiveno je 0.04 g 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-fluoropropil]-1-[2-(2,5-difluorofeniltio)etil]piperidin-4-karboksilne kiseline u obliku bijele krute tvari.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm): od 1.20 do 2.60 (mt: 12H); 2.66 (mt: 2H); 3.03 (t, J = 7 Hz: 2H); 3.93 (s: 3H); 6.38 (mt, JHF = 48 Hz: 1H); 7.05 (mt: 1H); od 7.20 do 7.40 (mt: 2H); 7.52 (dd, J = 9 i 2.5 Hz: 1H); 7.56 (d, J = 2.5 Hz: 1H); 8.04 (d, J = 9 Hz: 1H); 8.75 (široko s: 1H); od 12.30 do 12.70 (široki nedefinirani vršak: 1H).
Metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-fluoropropil]-1-[2-(2,5-difluorofeniltio)etil]piperidin-4-karboksilat
0.1 cm3 dietilaminosulfur trifluorida je dodano otopini od 0.25 g metilnog 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]-1-[2-(2,5-difluorofeniltio)etil]piperidin-4-karboksilata u 10 cm3 dioklorometana, uz miješanje u inertnoj atmosferi, na temperaturi od 5°C. Nakon miješanja tijekom 7 sati na temperaturi od 20°C, dodana je u reakcijsku smjesu zasićena otopina natrij hidrogen karbonata. Vodena faza je ekstrahirana diklorometanom. Organska faza je isušena na magnezijevom sulfatu, filtrirana, a zatim koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 70-200 μ; masa: 15 g), eluiranjem sa 60 cm3 diklorometana, a potom sa 45 cm3 smjese etilnog acetata/diklorometana (1/9 omjer volumena), te sa 30 cm3 smjese etilnog acetata/diklorometana (2/8 omjer volumena) i sa 210 cm3 smjese etilnog acetata/diklorometana (3/7 omjer volumena), te na kraju sa etilnim acetatom. Frakcije 24 do 26 su kombinirane i koncentrirane do isušenja u skladu sa prethodno navedenim uvjetima. Dobiveno je 0.08 g metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-fluoropropil]-1-[2-(2,5-difluorofeniltio)etil]piperidin-4-karboksilata u obliku gustog žutog ulja.
1H NMR spektar (400 MHz, (CD3)2SO-d6, δ u ppm) : od 1.20 do 2.60 (mt: 12H); od 2.55 do 2.75 (mt: 2H); 3.11 (t, J = 7 Hz: 2H); 3.54 (s: 3H); 3.93 (s: 3H); 6.36 (mt, JHF = 48 Hz: 1H); 7.05 (mt: 1H); od 7.15 do 7.35 (mt: 2H); od 7.45 do 7.55 (mt: 2H); 8.03 (d, J = 9 Hz: 1H); 8.75 (široko s: 1H).
Metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]-1-[2-(2,5-difluorofeniltio)etil]piperidin-4-karboksilat
Smjesa od 1.75 g etil 4-[3-(3-kloro-6-metoksikinolin-4-il)-propil]piperidin-4-karboksilatnog dihidroklorida, 0.95 g 2-(2-bromoetiltio)-1,4-difluorobenzena, 0.622 g kalijeva jodida i 3.11 g kalijeva karbonata u 30 cm3 acetonitrila i 20 cm3 dimetilformamida je zagrijavana uz miješanje tijekom 18 sati na temperaturi od 85°C. Nakon hlađenja na približno 20°C, reakcijska smjesa je filtrirana na dijatomejskoj zemlji (Celit) i filtrat je zatim koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen vodom i dietilnim eterom. Organska faza je isušena na magnezijevom sulfatu, filtrirana i koncentrirana do isušenja kao što je prethodno navedeno. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 70-200 μ; promjer 4 cm), eluiranjem sa smjesom diklorometan/metanol (97.5/2.5 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod prethodno navedenim uvjetima. Dobiveno je 0.6 g metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]-1-[2-(2,5-difluorofeniltio)etil]piperidin-4-karboksilata.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.20 do 2.15 (mt: 10H); od 2.45 do 2.55 (mt: 2H); 2.64 (mt: 2H); 3.12 (t, J = 7 Hz: 2H); 3.47 (s: 3H); 3.87 (s: 3H); 5.41 (mt: 1H); 6.10 (nedefinirani vršak: 1H); 7.04 (mt: 1H); od 7.15 do 7.35 (mt: 2H); od 7.45 (dd, J = 9 i 2.5 Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.13 (vrlo široko d, J = 2.5 Hz: 1H); 8.66 (s: 1H).
2-(2-bromoetiltio)-l,4-difluorobenzen je dobiven primjenom postupka opisanog u Primjeru 14.
Metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]piperidin-4-karboksilat je pripravljen u Primjeru 49.
Primjer 49
4-[3-(3-Kloro-6-metoksikinolin-4-il)-3-(R,S)-fluoropropil]-1-[2-(2,5-difluorofenoksi)etil]piperidin-4-karboksilna kiselina
Smjesa 0.15 g etil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-fluoropropil]-1-[2-(2,5-difluorofenoksi)etil]piperidin-4-karboksilata u 3 cm3 dioksana, 3 cm3 metanola i l cm3 5N vodene otopine natrijeva hidroksida je održavana na temperaturi od 70°C tijekom 4 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Ostatak je kromatografiran pod atosferskim tlakom od 60 kPa, na Bond Elut od 60 cm3 silikagela (veličina čestice 70-200 μ; masa 25 g), eluiranjem sa 60 cm3 smjese diklorometan/metanol/vodena otopina amonijaka (40/5/0.5 omjer volumena), a zatim sa smjesom diklorometana/metanola/vodene otopine amonijaka (40/5/2 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane i koncentrirane do isušenja pod prethodno navedenim uvjetima. Dobiveno je 0.04 g 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-fluoropropil]-1-[2-(2,5-difluorofenoksi)etil]piperidin-4-karboksilne kiseline u obliku bijele krute tvari.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.20 do 2.40 (mt: 10H); 2.65 (t, J = 6 Hz: 2H); 2.72 (mt: 2H); 3.93 (s: 3H); 4.03 (t, J = 6 Hz: 2H); 6.37 (mt, JHF = 48 Hz: 1H); 6.75 (mt: 1H); 7.14 (mt: 1H); 7.25 (mt: 1H); 7.52 (dd, J = 9 i 2.5 Hz: 1H); 7.56 (d, J = 2.5 Hz: 1H); 8.03 (d, J = 9 Hz: 1H); 8.75 (d, J = l Hz: 1H).
Metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-fluoropropil]-1-[2-(2,5-difluorofenoksi)etil]piperidin-4-karboksilat
0.2 cm3 dietilaminosulfur trifluorida je dodano otopini od 0.5 g metilnog 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]-1-[2-(2,5-difluorofenoksi)etil]piperidin-4-karboksilata u 20 cm3 dioklorometana, uz miješanje u inertnoj atmosferi, na temperaturi od 3°C. Nakon miješanja tijekom 7 sati na temperaturi od 20°C, dodana je u reakcijsku smjesu zasićena otopina natrij hidrogen karbonata. Vodena faza je ekstrahirana diklorometanom. Organska faza je isušena na magnezijevom sulfatu, filtrirana, a zatim koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 70-200 μ; promjer 1.5 cm; masa: 15 g), eluiranjem sa smjesom etilog acetata/petrolejskog etera (40-60°C) (8/2 omjer volumena). Frakcije 9 do 11 su kombinirane i koncentrirane do isušenja u skladu sa prethodno navedenim uvjetima. Dobiveno je 0.21 g metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-fluoropropil]-1-[2-(2,5-difluorofenoksi)etil]piperidin-4-karboksilata u obliku gustog žutog ulja.
Spektar mase: DCI m/z = 551 MH+
Prisustvo nečistoće m' = 532.
Metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]-1-[2-(2,5-difluorofenoksi)etil]piperidin-4-karboksilat
Smjesa od 1.55 g metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-hidroksipropil]piperidin-4-karboksilata, 1.03 g 1-(2-bromoetoksi)-2,5-difluorobenzena, 0.65 g kalijeva jodida i 2.7 g kalijeva karbonata u 30 cm3 acetonitrila i 20 cm3 dimetilformamida je zagrijavana uz miješanje tijekom 17 sati na temperaturi od 85°C. Nakon hlađenja na približno 20°C, reakcijska smjesa je filtrirana na dijatomejskoj zemlji (Celit) i filtrat je zatim koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je obrađen diklorometanom i vodom. Organska faza je isušena na magnezijevom sulfatu, filtrirana i koncentrirana do isušenja kao što je prethodno navedeno. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 70-200 μ; promjer 4 cm), eluiranjem sa smjesom diklorometan/metanol (97/3 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa), na temperaturi od 40°C, te pod istim uvjetima kao što je gore navedeno. Dobiveno je 0.5 g metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]-1-[2-(2,5-difluorofenoksi)etil]piperidin-4-karboksilata.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.20 do 2.20 (mt: 10H); od 2.60 do 2.80 (mt: 2H); 2.64 (t, J = 6 Hz: 2H) ; 3.48 (s: 3H) ; 3.88 (s: 3H) ; 4.12 (t, J = 6 Hz: 2H) ; 5.40 (mt: 1H); 6.10 (široko s: 1H); 6.74 (mt: 1H); 7.13 (mt: 1H); 7.24 (mt: 1H); 7.44 (dd, J = 9 i 2.5 Hz: 1H); 7.96 (d, J = 9 Hz: 1H); 8.14 (d, J = 2.5 Hz: 1H); 8.66 (s: 1H).
Metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]piperidin-4-karboksilat
Smjesa od 2.95 g metilnog 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]-(terc-butiloksikarbonil)-piperidin-4-karboksilata i 2.3 cm3 sulfatne kiseline u 100 cm3 metanola je zagrijavana na temperaturi od 80°C tijekom l sata i 30 minuta. Nakon hlađenja, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Ostatak je obrađen sa 10 cm3 vode, bazificiran do pH vrijednosti 11 primjenom zasićene otopine natrijeva bikarbonata, a zatim zasićene otopine natrijeva karbonata i koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 20-45 μ; promjer 2 cm; volumen 80 cm3), eluiranjem sa smjesom kloroforma/metaola/vodene otopine amonijaka (12/3/0.5 omjer volumena). Frakcije 8 do 20 su kombinirane, a zatim koncentrirane do isušenja pod identičnim uvjetima kao što je prethodno navedeno. Dobiveno je 1.37 g metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]piperidin-4-karboksilata u obliku krem obojene pjene.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.10 do 1.45 (mt: 3H); od 1.55 do 1.75 (mt: 1H); od 1.80 do 2.05 (mt: 4H); 2.40 (mt: 2H); 2.72 (mt: 2H); 3.50 (s: 3H); 3.90 (s: 3H) ; 5.42 (široki t, J = 6.5 Hz: 1H); 6.09 (mt: 1H); 7.45 (dd, J = 9 i 3 Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.15 (d, J = 3 Hz: 1H); 8.67 (s: 1H).
Metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]-(terc-butiloksikarbonil)piperidin-4-karboksilat
Otopina od 5 g etil 4-[3-(3-kloro-6-metoksikinolin-4-il)-propil]-(terc-butiloksikarbonil)piperidin-4-karboksilata u 400 cm3 dimetilnog sulfoksida i 120 cm3 terc-butanola je miješana u atmosferi zasićenoj kisikom na temperaturi od 20°C. Nakon 5 minuta, dodana je u reakcijsku smjesu otopina od 2.8 g kalijeva terc-butoksida u 30 cm3 terc-butanola. Nakon raspršenja sa kisikom tijekom 2 sata, dodano je oprezno 300 cm3 ledeno hladne vode i 3.5 cm3 octene kiseline. Vodena faza je ekstrahirana sa dva puta po 200 cm3 diklorometana. Organske faze su kombinirane i isprane sa 4 puta po l dm3 vode. Organska faza je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Ostatak je obrađen sa 200 cm3 dietilnog etera, filtriran, ispran sa 20 cm3 dietilnog etera i zatim isušen u sušilici pod sniženim tlakom (0.1 kPa) na temperaturi od 40°C. Dobiveno je 3 g metil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-(R,S)-hidroksipropil]-(terc-butiloksikarbonil)piperidin karboksilata u obliku bijele krute tvari točke taljenja 222°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.10 do 1.50 (mt: 3H); 1.39 (s: 9H); 1.70 (mt: 1H); od 1.80 do 2.10 (mt: 4H); 2.81 (mt: 2H); 3.69 (mt: 2H); 3.89 (s: 3H); 5.41 (dd, J = 9 i 5 Hz: 1H); od 5.80 do 6.30 (široki nedefinirani vršak: 1H); 7.44 (dd, J = 9 i 3 Hz: 1H); 7.95 (d, J = 9 Hz: 1H); 8.16 (d, J = 3 Hz: 1H); 8.65 (s: 1H); od 12.00 do 12.90 (široki nedefinirani vršak: 1H).
1-(2-Bromoetoksi)-2,5-difluorobenzen je pripravljen u Primjeru 16.
Etil 4-[3-(3-kloro-6-metoksikinolinil)propil]-1-(terc-butoksikarbonil)piperidin-4-karboksilat je pripravljen u Primjeru 5.
Primjer 50
Etil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tiazol-2-iloksi)etil]piperidin-4-karboksilat je pripravljen.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm): 1.05 (t, J = 7 Hz: 3H); 1.40 (vrlo široki t, J = 12 Hz: 2H); 1.53 (mt: 2H); 1.69 (mt: 2H); od 1.90 do 2.15 (mt: 4H); 2.64 (t, J = 5.5 Hz: 2H); 2.70 (široko d, J = 11.5 Hz: 2H); 3.16 (široki t, J = 7.5 Hz: 2H); 3.96 (s: 3H); 4.01 (q, J = 7 Hz: 2H); 4.42 (t, J = 5.5 Hz: 2H); 7.04 (d, J = 3.5 Hz: 1H); 7.17 (d, J = 3.5 Hz: 1H); 7.37 (d, J = 2.5 Hz: 1H); 7.46 (dd, J = 9 i 2.5 Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.67 (s: 1H).
4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tiazol-2-iloksi)etil]piperidin-4-karboksilna kiselina
Smjesa 0.68 g etilnog 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tiazol-2-iloksi)etil]piperidin-4-karboksilata u 7 cm3 dioksana, 9 cm3 metanola i 2 cm3 5N vodene otopine natrijeva hidroksida je održavana na temperaturi od 60°C tijekom 20 sati. Nakon hlađenja na približno 20°C, reakcijska masa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je kromatografiran pod tlakom argona od 50 kPa, na stupcu silikagela (veličina čestice 20-45 μ; promjer 2.2 cm; masa 20 g), eluiranjem sa smjesom diklorometana/metanola (70/30 omjer volumena). Frakcije koje sadržavaju očekivani produkt su kombinirane, a zatim koncentrirane do isušenja pod prethodno navedenim uvjetima. Dobiveni ostatak je obrađen sa 5 cm3 etilnog acetata, miješan tijekom l sata na sobnoj temperaturi, a zatim filtriran i ispran sa 3 puta po 3 cm3 etilnog acetata, te sa 3 puta po 3 cm3 etilnog acetata i sa 3 puta po 3 cm3 pentana. Dobiveno je 0.27 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tiazol-2-iloksi)etil]piperidin-4-karboksilne kiseline u obliku bijele krute tvari točke taljenja 188°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.39 (široki t, J = 12 Hz: 2H); od 1.50 do 1.65 (mt: 2H); 1.71 (mt: 2H); 1.98 (široki d, J = 12 Hz: 2H); 2.12 (nedefinirani vršak: 2H); od 2.60 do 2.85 (mt: 4H); 3.17 (široki t, J = 7.5 Hz: 2H); 3.96 (s: 3H); 4.45 (vrlo široki t, J = 5.5 Hz: 2H); 7.05 (d, J = 3.5 Hz: 1H); 7.18 (d, J = 3.5 Hz: 1H); 7.37 (d, J = 2.5 Hz: 1H); 7.46 (dd, J = 9 i 2.5 Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.68 (s: 1H); od 11.80 do 12.70 (široki nedefinirani vršak: 1H).
Primjer 51
4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(4,5-dihidrotiazol-2-iltio)etil]piperidin-4-karboksilna kiselina
Smjesa 0.15 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(4,5-dihidrotiazol-2-iltio)etil]piperidin-4-karboksilata u 5 cm3 dioksana, 5 cm3 metanola i l cm3 5N vodene otopine natrijeva hidroksida je održavana na temperaturi od 70°C tijekom 20 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (Bond Elut; veličina čestice 70-200 μ; masa 7 g), eluiranjem sa smjesnom diklorometan/metanol/vodena otopina amonijaka (40/5/0.5 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C, te isušene u pećnici pod sniženim tlakom (10 kPa) na temperaturi od 50°C. Dobiveno je 0.1 g 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(4,5-dihidrotiazol-2-iltio)etil]piperidin-4-karboksilne kiseline u obliku bijele krute tvari.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.33 (vrlo široki t, J = 11.5 Hz: 2H); 1.61 (mt: 4H); od 1.90 do 2.10 (mt: 4H); od 2.45 do 2.60 (mt: 2H); 2.63 (široko d, J = 11.5 Hz: 2H); 3.05 (mt: 2H); 3.19 (t, J = 6.5 Hz: 2H); 3.44 (t, J = 8 Hz: 2H); 3.97 (s: 3H); 4.15 (t, J = 8 Hz: 2H); 7.35 (široki s: 1H); 7.40 (široki d, J = 9Hz: 1H); 7.97 (široki d, J = 9 Hz: 1H); 8.69 (široki s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2- (4,5-dihidrotiazol-2-iltio)etil]piperidin-4-karboksilat
Smjesa 0.7 g etil 1-(2-kloroetil)-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilatni dihidroklorida, 0.18 g 2-merkaptotiazolina i 0.63 cm3 trietilamina u 10 cm3 dimetilformamida je miješana u inertnoj atmosferi tijekom 23 sata na temperaturi od 80°C. Nakon hlađenja na 20°C, reakcijska smjesa je obrađena vodom, ekstrahirana etilnim acetatom i isprana zasićenom otopinom natrijeva klorida. Organska faza je isušena na magnezijevom sulfatu, filtrirana i zatim koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je dodan otopini od 0.18 g 2-merkaptotiazolina i 0.06 g 10% natrijeva hidrida u 10 cm3 dimetilformamida, a smjesa je zatim zagrijavana na temperaturi od 80°C tijekom 15 sati. Nakon hlađenja na 20°C, reakcijska smjesa je obrađena vodom, ekstrahirana etilnim acetatom i isprana zasićenom otopinom natrijeva klorida. Organska faza je isušena na magnezijevom sulfatu, filtrirana i zatim koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom na stupcu silikagela (veličina čestice 70-200 μ; promjer 2 cm; masa 40 g), eluiranjem sa smjesom diklorometan/etanol (95/5 omjer volumena) i sakupljanjem 10-cm3 frakcija. Frakcije 11 do 24 su kombinirane i zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 0.15 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(4,5-dihidrotiazol-2-iltio)etil]piperidin-4-karboksilata u obliku smeđeg ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, uz dodatak nekoliko kapi CD3COOD d4, δ u ppm): 1.06 (t, J = 7 Hz: 3H); 1.41 (mt: 2H); od 1.50 do 1.70 (mt: 4H); 1.98 (široki d, J = 13.5 Hz: 2H); 2.14 (široki t, J = 11.5 Hz: 2H); 2.66 (t, J = 7 Hz: 2H); 2.80 (vrlo široki d, J = 11.5 Hz: 2H); 3.04 (široki t, J = 6.5 Hz: 2H); 3.21 (t, J = 7 Hz: 2H); 3.42 (t, J = 8 Hz: 2H); 3.94 (s: 3H); 3.97 (q, J = 7 Hz: 2H); 4.12 (t, J =8 Hz: 2H); 7.32 (d, J = 2.5 Hz: 1H); 7.38 (dd, J = 9 i 2.5 Hz: 1H); 7.96 (d, J = 9 Hz: 1H); 8.66 (d, J = 1.5 Hz: 1H).
Etil 1-(2-kloroetil)-(4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilatni dihidroklorid
5.73 cm3 tionilnog klorida je dodano kap po kap otopini od 0.6 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(2-hidroksietil)piperidin-4-karboksilata u 10 cm3 diklorometana uz miješanje na temperaturi od 20°C. Smjesa je miješana tijekom 24 sata na temperaturi od 20°C. Reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Ostatak je obrađen sa 3 puta po 30 cm3 cikloheksana i uparen do isušenja pod prethodno navedenim uvjetima. Dobiveno je 0.67 g etil 1-(2-kloroetil)-(4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilatnog dihidroklorida u obliku bež obojene krute tvari.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.05 (t, J = 7 Hz: 3H); od 1.45 do 2.00 (mt: 6H); 2.19 (široki d, J = 14 Hz: 2H); od 2.75 do 2.95 (mt: 2H); 3.09 (mt: 2H); od 3.40 do 3.60 (mt: 4H); od 3.95 do 4.15 (mt: 2H); 3.96 (s: 3H); 4.05 (q, J = 7 Hz: 2H); 7.37 (d, J = 2.5 Hz: 1H); 7.42 (dd, J = 9 i 2.5 Hz: 1H); 7.99 (d, J = 9 Hz: 1H); 8.73 (široko s: 1H); 10.00 nedefinirani vršak: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(2-hidroksietil)piperidin-4-karboksilat je pripravljen analogno postupku opisanom u Primjeru 46.
Primjer 52
4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-karboksilna kiselina
Smjesa 0.8 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-karboksilata u 50 cm3 dioksana, 50 cm3 metanola i 4.4 cm3 5N vodene otopine natrijeva hidroksida je miješana na temperaturi od 70°C tijekom 18 sati. U reakcijsku smjesu je zatim dodano daljnjih 4.4 cm3 5N vodene otopine natrijeva hidroksida, te je miješana tijekom 6 sati na temperaturi od 70°C. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (1.1 kPa) na temperaturi od 50°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 20-45 μ; promjer 4 cm; visina 20cm), eluiranjem sa smjesnom kloroform/-metanol/vodena otopina amonijaka (12/3/0.5 omjer volumena) i sakupljanjem 60-cm3 frakcija. Frakcije 8 do 19 su kombinirane, koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C, te isušene u pećnici pod sniženim tlakom (10 kPa) na približno 50°C. Dobiveno je 0.59 g 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-triflorofeniksi)etil]piperidin-4-karboksilne kiseline u obliku bijele krute tvari, točke taljenja 120°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.32 (vrlo široki t, J = 12 Hz: 2H); 1.59 (mt: 4H); 1.95 (široki d, J = 12 Hz: 2H); 2.07 (široki t, J = 11 Hz: 2H); 2.59 (t, J = 5.5 Hz: 2H); 2.68 (vrlo široki d, J = 11 Hz: 2H); 6.97 (mt: 2H); 7.34 (d, J = 2.5 Hz: 1H); 7.39 (dd, J = 9 i 2.5 Hz: 1H); 7.96 (d, J = 9 Hz: 1H); 8.69 (široki s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4,5-trifluorofenoksi)etil]piperidin-4-karboksilat
Smjesa od 0.62 g etil 4-[3-(3-kloro-6-metoksikinolin-4-il)-3-hidroksipropil]piperidin-4-karboksilata, 0.505 g 5-(2-bromoetoksi)-l,2,3-trifluorobenzena, 0.34 g kalijeva jodida i 1.14 g kalijeva karbonata u 80 cm3 acetonitrila je miješana u inertnoj atmosferi tijekom 18 sati na temperaturi od 70°C. Nakon hlađenja na približno 20°C, suspenzija je filtrirana, a netopljivi materijal je ispran sa 3 puta po 30 cm3 acetonitrila. Filtrat je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 20-45 μ; promjer 3 cm; visina 21 cm), eluiranjem sa etilnim acetatom i sakupljanjem 40-cm3 frakcija. Frakcije 9 do 24 su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 0.8 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(3,4, 5-trifluorofenoksi)-etil]piperidin-4-karboksilata u obliku blijedožutog viskoznog ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm): 0.99 (t, J = 7 Hz: 3H); 1.37 (vrlo široki t, J = 12 Hz: 2H); od 1.45 do 1.70 (mt: 4H); od 1.90 do 2.10 (mt: 4H); 2.59 (t, J = 5.5 Hz: 2H); 2.69 (široki d, J = 12 Hz: 2H); 3.04 (široki t, J = 7 Hz: 2H); 3.94 (s: 3H); 3.97 (q, J = 7 Hz: 2H); 4.03 (t, J = 5.5 Hz: 2H); 6.97 (mt: 2H); 7.33 (d, J = 2.5 Hz: 1H); 7.39 (dd, J = 9 i 2.5 Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.69(široko s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat je pripravljen u Primjeru 11.
5-(2-Bromoetoksi)-1,2,3-trifluorobenzen je pripravljen primjenom postupka opisanog u Primjeru 13.
Primjer 53
4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tiazol-2-iltio)etil]piperidin-4-karboksilna kiselina
Smjesa 0.15 g 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tiazol-2-iltio)etil]piperidin-4-karboksilata u 3 cm3 dioksana, 3 cm3 metanola i l cm3 5N vodene otopine natrijeva hidroksida je miješana na temperaturi od 70°C tijekom 18 sati. Nakon hlađenja na približno 20°C, reakcijska masa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 50°C. Dobiveni ostatak je obrađen sa dva puta po 20 cm3 toluena i zatim koncentriran do isušenja pod gore navedenim uvjetima. Kruta tvar je pročišćena kromatografijom pod atmosferskim tlakom, na stupcu silikagela (Bond Elut; veličina čestice 70-200 μ; masa 7 g), eluiranjem sa smjesnom kloroform/metanol/vodena otopina amonijaka (84/14/2 omjer volumena) i sakupljanjem 5-cm3 frakcija. Frakcije 8 do 19 su kombinirane, koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C, te isušene u pećnici pod sniženim tlakom (10 kPa) na približno 50°C. Dobivno je 0.114 g 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tiazol-2-il-tio)etil]piperidin-4-karboksilne kiseline u obliku bijele krute tvari.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.31 (široki t, J = 12 Hz: 2H); od 1.45 do 1.70 (mt: 4H); od 1.90 do 2.10 (mt: 4H); 2.58 (t, J = 7 Hz: 2H); 2.65 (široki d, J = 12 Hz: 2H); 3.04 (mt: 2H); od 3.25 do 3.45 (mt: 2H); 3.95 (s: 3H); 7.34 (d, J = 2.5 Hz: 1H); 7.39 (dd, J = 9 i 2.5 Hz: 1H); 7.63 (d, J = 3.5 Hz: 1H); 7.71 (d, J = 3.5 Hz: 1H); 7.96 (d, J = 9 Hz: 1H); 8.68 (d, J = l Hz: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tiazol-2-iltio)etil]piperidin-4-karboksilat
Smjesa od 0.65 g etil 1-(2-kloroetil)-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilatnog dihidroklorida, 0.183 g 2-merkaptotiazola, 0.21 g kalijeva jodida i 0.88 g kalijeva karbonata u 50 cm3 acetonitrila je miješana u inertnoj atmosferi tijekom 18 sati na temperaturi od 70°C. Nakon hlađenja na približno 20°C, suspenzija je filtrirana, a netopljivi materijal je ispran acetonitrilom. Filtrat je koncentriran do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Uparavanjem dobiveni ostatak je obrađen sa smjesom etilnog acetata/40-60°C petrolejskog etera (8/2 omjer volumena) i filtriran, a filtrat je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 70-200 μ; promjer 1.5 cm; masa 100 g), eluiranjem sa etilnim acetatom/40-60°C petrolejskog etera (8/2 omjer volumena) i sakupljanjem 15-cm3 frakcija. Frakcije 41 do 100 su kombinirane, a zatim koncentrirane do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveno je 0.15 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(tiazol-2-iltio)etil]piperidin-4-karboksilata u obliku gustog žutog ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm): 1.00 (t, J = 7 Hz: 3H); 1.36 (široki t, J = 11.5 Hz: 2H); od 1.45 do 1.70 (mt: 4H); od 1.85 do 2.10 (mt: 4H); 2.59 (t, J = 7 Hz: 2H); 2.68 (široki d, J = 12 Hz: 2H) ; 3.05 (vrlo široki t, J = 7 Hz: 2H); 3.33 (mt: 2H); 3.96 (s: 3H) ; 3.98 (q, J = 7 Hz: 2H); 7.35 (d, J = 2.5 Hz: 1H); 7.40 (dd, J = 9 i 2.5 Hz: 1H); 7.64 (d, J = 3.5 Hz: 1H); 7.72 (d, J = 3.5 Hz: 1H); 7.97 (d, J = 9 Hz: 1H); 8.70 (d, J = l Hz: 1H).
Etil 1-(2-kloroetil)-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilatni dihidroklorid je pripravljen u Primjeru 51.
Primjer 54
4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(3-fenilalil)piperidin-4-karboksilna kiselina
Smjesa 0.13 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(3-fenilalil)piperidin-4-karboksilata u 2 cm3 dioksana, 2 cm3 metanola i 1.32 cm3 5N vodene otopine natrijeva hidroksida je održavana na temperaturi od 70°C tijekom 18 sati. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen sa 10 cm3 vode, zakiseljen octenom kiselinom i ekstrahiran etilnim acetatom, ostavljen da se odvoji taloženjem, a zatim filtriran i ispran sa dva puta po 10 cm3etanola. Dobivno je 0.12 g 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(3-fenilalil)-piperidin-4-karboksilne kiseline u obliku bijele krute tvari, točke taljenja 240°C.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.35 (široki t, J = 11.5 Hz: 2H); od 1.50 do 1.75 (mt: 4H); od 1.85 do 2.10 (mt: 4H); 2.63 (široki d, J = 11.5 Hz: 2H); od 2.95 do 3.15 (mt: 4H); 3.96 (s: 3H); 6.26 (dt, J = 16 i 7 Hz: 1H); 6.50 (d, J = 16 Hz: 1H); od 7.10 do 7.50 (mt: 7H); 8.06 (d, J = 9 Hz: 1H); 8.69 (široki s: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(3-fenilalil)piperidin-4-karboksilat
77 mg boran-piridinskog kompleksa je dodano u smjesu od 0.31 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilata i 0.1 cm3 trans-cinamaldehida u 10 cm3 etanola. Temperatura reakcijske smjese je održavana na 77°C tijekom 22 sata. Nakon hlađenja na približno 20°C, reakcijska smjesa je koncentrirana do isušenja pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je obrađen sa 20 cm3 vode, ekstrahiran sa dva puta po 10 cm3 diklorometana, isušen na magnezijevom sulfatu, filtriran i zatim koncentriran do isušenja pod gore navedenim uvjetima. Dobiveni ostatak je kromatografiran pod tlakom od 60 kPa argona, na stupcu silikagela (veličina čestice 70-200 μ; promjer 2.5 cm; masa 20 g), eluiran sa 500 cm3 smjese etilnog acetata/cikloheksana (40/60 omjer volumena), a zatim sa smjesom diklorometana/-metanola (95/5 omjer volumena). Frakcije koje sadržavaju očekivani produkt su kombinirane, a zatim koncentrirane do isušenja pod gore navedenim uvjetima. Dobiveno je 0.13 g etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(3-fenilalil)piperidin-4-karboksilata u obliku viskoznog ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.01 (t, J = 7 Hz: 3H); 1.40 (široki t, J = 11.5 Hz: 2H); od 1.45 do 1.75 (mt: 4H); od 1.90 do 2.05 (mt: 4H); 2.65 (vrlo široki d, J = 12 Hz: 2H); 3.02 (d, J = 7 Hz: 2H); 3.05 (mt: 2H); 3.96 (s: 3H); 3.97 (q, J = 7 Hz: 2H); 6.25 (dt, J = 16 i 7 Hz: 1H); 6.51 (d, J = 16 Hz: 1H); od 7.15 do 7.50 (mt: 7H); 7.96 (d, J = 9 Hz: 1H); 8.70 (d, J = l Hz: 1H).
Etil 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-karboksilat je pripravljen u Primjeru 11.
Primjer 55
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)piperidin-4-hidroksamična kiselina
Otopina od 0.1 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)-piperidin-4-terc-butoksikarboksamida u 2 cm3 trifluorooctene kiseline je ostavljena 60 dana na temperaturi od 20°C. Otopina je uparena pod sniženim tlakom (2 kPa) na temperaturi od 40°C, a zatim pročišćena kromatografijom pod atmosferskim tlakom na Bond Elut siliciju (veličina čestice 70-200 μ; volumen 25 cm3), eluiranjem sa smjesom diklorometana/metanola/vodene otopine amonijaka (40/5/0.3 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, a zatim uparene pod prethodno opisanim uvjetima. Dobiveno je 0.036 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)piperidin-4-hidroksamične kiseline u obliku bezbojnog ulja.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.33 (mt: 2H); 1.51 (mt: 2H); od 1.60 do 1.80 (mt: 4H); od 1.90 do 2.10 (mt: 4H); 2.18 (t, J = 7 Hz: 2H); od 2.45 do 2.65 (mt: 4H); 3.12 (široki t, J = 7.5 Hz: 2H); 3.96 (s: 3H); od 7.15 do 7.25 (mt: 3H); 7.28 (t mt, J = 7.5 Hz: 2H); 7.36 (d, J = 2.5 Hz: 1H); 7.45 (dd, J = 9 i 2.5 Hz: 1H); 7.96 (d, J = 9 Hz: 1H); 8.56 (nedefinirani vršak: 1H); 8.67 (s: 1H); 10.37 (nedefninirani vršak: 1H).
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)piperidin-4-terc-butoksamid
Smjesa od 0.5 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)piperidin-4-karboksilne kiseline, 0.175 g 1-hidroksi-benzotriazolnog hidrata, 0.498 g 1-[3-(dimetilamino)-propil]-3-etilkarbodiimidnog hidroklorida, 0.58 cm3 trietilamina i 0.4 g 0-terc-butilhidroksilamina je miješana tijekom 48 sati na temperaturi od 20°C. Reakcijska smjesa je razrijeđena sa 50 cm3 vode, miješana, a faze su zatim razdvojene taloženjem. Vodena faza je dva puta ekstrahirana sa 25 cm3 diklorometana, a organski ekstrakti su kombinirani, isušeni na magnezijevom sulfatu, filtrirani, a zatim upareni pod sniženim tlakom (2 kPa) na temperaturi od 40°C. Dobiveni ostatak je pročišćen kromatografijom pod atmosferskim tlakom, na stupcu silikagela (veličina čestice 20-45 μ; promjer 2.5 cm; masa 18 g), eluiranjem sa smjesom diklorometana/metanola/-vodene otopine amonijaka (40/5/0.2 omjer volumena). Frakcije koje sadržavaju produkt su kombinirane, a zatim uparene pod prethodno navedenim uvjetima. Dobiveno je 0.27 g 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)-piperidin-4-terc-butoksamida.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.09 (s: 9H); 1.35 (mt: 2H); 1.54 (mt: 2H); 1.67 (mt: 4H); 1.95 (široki t, J = 13.5 Hz: 2H); 2.19 (t, J = 7 Hz: 2H); od 2.50 do 2.65 (mt: 4H); 3.14 (široki t, J= 7.5 Hz: 2H); 3.98 (s: 3H); od 7.10 do 7.25 (mt: 3H); 7.27 (široki t, J = 7.5 Hz: 2H); 7.36 (d, J = 2.5 Hz: 1H); 7.45 (dd, J = 9 i 2.5 Hz: 1H); 7.96 (d, J = 9 Hz: 1H); 8.68 (s: 1H); 10.06 (široki s: 1H).
4-[3-(3-Kloro-6-metoksikinolin-4-il)propil]-1-(3-fenilpropil)piperidin-4-karboksilna kiselina je pripravljena u Primjeru 4.
Benzil 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1- (3-fenilpropil)piperidin-4-karboksilat je pripravljen u Primjeru 4.
Primjer 56
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,5-difluorofenil)prop-2-enil]piperidin-4-karboksilne kiseline hidroklorid
Analogno primjeru 54, pripravljen je 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[3-(2,5-difluorofenil)prop-2-enil]piperidin-4-karboksilne kiseline hidroklorid.
1H NMR spektar (300 MHz, (CD3)2SO-d6, uz dodatak nekoliko kapi CD3COOD-d4, na temperaturi od 383 K, δ u ppm): 1.73 (mt: 6H); 2.22 (široki d, J = 14 Hz: 2H); 3.01 (nedefinirani vršak: 2H); 3.11 (široki t, J = 7 Hz: 2H); 3.42 (vrlo široki d, J = 12 Hz: 2H); 3.94 (d, J = 7 Hz: 2H); 3.98 (s: 3H); 6.48 (dt, J = 16.5 Hz: 1H); 6.93 (d, J = 16.5 Hz: 1H); od 7.10 do 7.30 (mt: 2H); 7.35 (široki s: 1H); 7.40 (dd, J = 9 i 2.5 Hz: 1H); 7.44 (mt: 1H); 7.98 (d, J = 9 Hz: 1H); 8.64 (široki s: 1H).
Primjer 57
4-[3-(3-Fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,5-difluorofenoksi)etil]piperićLLn-4-hidroksamična kiselina
Analogno primjeru 55, pripravljen je 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-[2-(2,5-difluorofenoksi)etil]-piperidin-4-hidroksamična kiselina.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : od 1.45 do 1.70 (mt: 4H); 2.02 (široki d, J = 12.5 Hz: 2H); 2.10 (široki t, J = 11 Hz: 2H); od 2.55 do 2.75 (mt: 4H); 3.00 (mt: 2H); 3.97 (s: 3H); 4.12 (t, J = 5.5 Hz: 2H); 6.75 (mt: 1H); 7.14 (mt: 1H); 7.24 (mt: 1H); 7.33 (d, J = 3 Hz: 1H); 7.40 (dd, J = 9 i 3 Hz: 1H); 8.70 (d, J = 0.5 Hz: 1H); 10.40 (nedefinirani vršak: 1H).
Primjer 58
1-Cinamil-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-hidroksamična kiselina
Analogno primjeru 55, pripravljena je l-cinamil-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-piperidin-4-hidroksamična kiselina.
1H NMR spektar (300 MHz, (CD3)2SO-d6, uz dodatak nekoliko kapi CD3COOD-d4, na temperaturi od 383 K, δ u ppm) : 1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm): od 1.50 do 1.75 (mt: 6H); 2.23 (široki d, J = 14 Hz: 2H); 2.81 (široki t, J = 11.5 Hz: 2H); 3.04 (mt: 2H); 3.22 (široki d, J = 11.5 Hz: 2H); 3.69 (d, J = 7 Hz: 2H); 3.97 (s: 3H); 6.24 (dt, J = 16 i 7 Hz: 1H); 6.78 (d, J = 16 Hz: 1H); od 7.20 do 7.50 (mt: 7H); 7.96 (d, J = 9 Hz: 1H); 8.62 (široko s: 1H).
Primjer 59
Natrijev 4-[3-(3-kloro-6-trifluorometilkinolin-4-il)propil]-1-[2-(2,5-difluorofenoksi)etil]piperidin-4-karboksilat
Analogno primjeru l, pripravljen je natrijev 4-[3-(3-kloro-6-trifluorometilkinolin-4-il)propil]-1-[2-(2, 5-difluorofenoksi)etil]-piperidin-4-karboksilat.
1H NMR spektar (300 MHz, (CD3)2SO-d6, δ u ppm) : 1.09 (široki t, J = 11.5 Hz: 2H); od 1.40 do 1.70 (mt: 4H); 1.98 (široki d, J = 11.5 Hz: 2H); 2.14 (t, J = 10.5 Hz: 2H); od 2.50 do 2.70 (mt: 4H); 3.22 (široki t, J = 7 Hz: 2H); 4.10 (t, J = 5.5 Hz: 2H); 6.74 (mt: 1H); 7.12 (mt: 1H); 7.23 (mt: 1H); 8.06 (široko d, J = 9 Hz: 1H); 8.26 (d, J = 9 Hz: 1H); 8.26 (d, J = 9 Hz: 1H); 8.54 (široko s: 1H); 9.00 (s: 1H).
Prikazani izum se isto tako odnosi na farmaceutske pripravke koji sadrže najmanje jedan heterociklilalkil-piperidinski derivat u skladu s izumom, a gdje je prikladno pojavljuje se u obliku soli, u čistom obliku ili u kombinaciji s jednim ili više kompatibilnim i farmaceutski prihvatljivim diluensom i/ili adjuvansom.
Pripravci se u skladu s izumom mogu primijeniti oralnim putem, parenteralno, lokalno, rektalno ili u obliku raspršivača.
Kao kruti pripravci za oralnu primjenu mogu se koristiti tablete, pilule, gelatinozne kapsule, prašci ili granule. U navedenim pripravcima, aktivni produkt u skladu s izumom je smjesa s jednim ili više inertnih diluensa ili adjuvansa, kao što je sukroza, laktoza ili škrob. Navedeni pripravci mogu sadržavati druge supstance pored diluensa, kao na primjer lubrikans u obliku magnezijevog stearata ili mogu biti obloženi kako bi se postiglo kontrolirano otpuštanje supstance.
Tekući pripravci za oralnu primjenu mogu obuhvaćati farmaceutski prihvatljive otopine, suspenzije, emulzije, sirupe i eliksire koji sadrže inertne diluense kao što je voda ili tekući parafin. Navedeni pripravci mogu isto tako pored diluensa sadržavati supstance, kao što su sredstva za vlaženje, zaslađivači ili sredstva za poboljšanje okusa.
Pripravci za parenteralnu primjenu mogu doći u obliku sterilnih otopina ili emulzija. Solventi ili vehikuli koji se koriste mogu obuhvaćati vodu, propilen glikol, polietilen glikol, biljna ulja, osobito maslinovo ulje, te injektibilne organske estere, na primjer etilni oleat. Navedeni pripravci mogu isto tako sadržavati adjuvanse, osobito sredstva za vlaženje, izotonična sredstva, emulzifikatore, dispergirajuća sredstva i stabilizatore.
Sterilizacija se može izvesti na nekoliko načina, na primjer primjenom bakteriološkog filtera, zračenjem ili zagrijavanjem. Pripravci se mogu isto tako pripraviti u obliku sterilnih krutih pripravaka koji se zatim za vrijeme primjene otope u sterilnoj vodi ili drugom injektibilnom sterilnom mediju.
Pripravci za lokalnu primjenu mogu biti, na primjer, kreme, masti, losioni i aerosoli.
Pripravci za rektalnu primjenu su supozitoriji ili rektalne kapsule koje sadržavaju, pored aktivne supstance, ekscipijens kao što je kakao maslac, semi-sintetske gliceride ili polietilen glikole.
Pripravci mogu isto tako doći u obliku aerosola. Za primjenu u tekućim aerosolima, pripravci mogu biti stabilne, sterilne otopine ili kruti pripravci otopljeni u vrijeme primjene u apirogenoj sterilnoj vodi, fiziološkoj otopini ili bilo kojem drugom farmaceutski prihvatljivom vehiklu. Za primjenu u obliku suhih aerosola koji su namijenjeni izravnoj inhalaciji, aktivna komponenta je fino razdijeljena i kombinirana sa u vodi topljivim krutim diluensom ili vehiklom veličine čestice od 30 do 80 μm, na primjer dekstran, manitol ili laktoza.
U liječenju ljudi, novi heterociklilalkilpiperidinski derivati u skladu sa prikazanim izumom, osobito su korisni za liječenje infekcija bakterijskog porijekla. Doziranje ovisi o očekivanom učinku, te o duljini liječenja. Liječnik će odrediti dozu koju smatra najprikladnijom za liječenje, ovisno o dobi, tjelesnoj težini bolesnika, stupnju infekcije i drugim specifičnim faktorima za pojedinca koji se liječi. Općenito, prikladne su doze odraslu osobu između 750 mg i 3 g aktivnog produkta primjenjene 2 ili 3 puta dnevno oralno ili između 400 mg i 1.2 g primijenjene intravenozno.
Claims (12)
1. Heterociklilalkilpiperidinski derivat, naznačen time, da se bira iz skupine spojeva prikazanih općom formulom:
[image]
u kojoj:
X1, X2, X3, X4 i X5 predstavljaju od >C-R'1 do >C-R'5, ili na drugi način, najviše jedan među njima predstavlja atom dušika,
R1, R'1, R'2, R'3, R'4 i R'5 su identični ili različiti i predstavljaju vodik ili halogeni atom ili alkil, cikloalkil, fenil, feniltio, mono- ili biciklički aromatski heterociklil ili heterocikliltio, hidroksi. alkiloksi, trifluorometoksi, alkiltio, trifluorometiltio, cikloalkiloksi, cikloalkiltio, cijano, karboksil, alkiloksikarbonil, cikloalkiloksikarbonil, -NraRb ili -CONRaRb radikal (u kojem Ra i Rb mogu predstavljati vodik, alkil, cikloalkil, fenil, mono- ili biciklički aromatski heterociklil ili Ra i Rb tvore, zajedno sa atomom dušika na koji su vezani, 5- ili 6-člani heterociklički prsten koji može po izboru sadržavati drugi heteroatom odabran između O, S i N, te, kada je prikladno, nose alkil, fenil ili mono- ili biciklički aromatski heterociklil supstituiran na dušikovom atomu, ili gdje je prikladno, atom sumpora koji je oksidiran u obliku sulfinila ili sulfonila), ili predstavlja metilenski radikal supstituiran s fluoro, hidroksil, alkiloksi, alkiltio, cikloalkiloksi, cikloalkiltio, fenil, mono- ili biciklički aromatski heterociklil, karboksil, alkiloksikarbonil, cikloalkiloksikarbonil, -NRaRb ili -CONRaRb u kojima Ra i Rb su u skladu s prethodn onavedenom definicijom, ili predstavljaju fenoksi, heterocikliloksi, benziloksi, heterociklilmetiloksi, ili na drugi način R1 može isto tako predstavljati difluorometoksi, ili radikal strukture -CmF2m+1, SCmF2m+1, ili -OCmF2m+1 u kojima je m cijeli broj između 1 i 6, ili na drugi način R'5 može isto tako predstavljati trifluoroacetil.
R2 predstavlja karboksil, alkiloksikarbonil, cikloalkiloksikarbonil, cijano, -CONRaRb (u kojem Ra i Rb predstavljaju, odnosno su, vodik, alkil, cikloalkil, fenil, mono- ili biciklički aromatski heterociklil, ili Ra ili Rb predstavljaju hidroksil, alkiloksi, cikloalkiloksi, ili Ra i Rb tvore, zajedno s atomom dušika na koji su vezani, 5- ili 6-člani heterociklički prsten koji može po izboru sadržavati drugi heteroatom odabran između O, S i N, te kada je prikladno, nosi alkil, fenil, ili mono- ili biciklički aromatski heterociklil supstituiran na atomu dušika ili, kada je prikladno, atom sumpora koji je oksidiran u obliku sulfinila ili sulfonila), ili Ra predstavlja hidroksimetil, alkil koji sadrže l ili 2 atoma ugljika supstituiranih karboksilom, alkiloksikarbonilom, cikloalkiloksikarbonilom, cijano ili -CONRaRb u kojem su Ra i Rb kao što su prethodno definirani, ili R2 predstavlja radikal strukture -CF2-Rc, -C(CH3)2-Rc u kojem je Rc karboksil, alkilokisarbonil, cikloalkiloksikarbonil, ili -CONRaRb u kojem Ra i Rb su definirani kao što je prethono navedeno.
R3 predstavlja fenil, mono- ili biciklički aromatski heterociklil ili alk-R°3 radikal u kojem alk označava alkilni radikal i R°3 r predstavlja vodik, halogen, hidroksil, alkiloksi, alkiltio, alkilsulfinil, akilsulfonil, alkilamino, dialkilamino, cikloalkil, cikloalkiloksi, cikloalkiltio, cikloalkilsufinil, cikloalkilsulfonil, cikloalkilamino, N-cikloalkil-N-alkilamino, -N-(cikloalkil)2, acil, cikloalkilkarbonil, fenil, fenoksi, feniltio, fenilsulfinil, fneilsulfonil, fenilamio, N-alkil-N-fenilamino, N-cikloalkil-N-fenilamino, -N-(fenil)2, fenilalkiloksi, fenilalkiltio, fenilalkilsulfinil, fenilalkilsulfonil, fenilalkilamino, N-alkil-N-fenilaminoalkil, N-cikloalkil-N-fenilalkilamino, benzoil, mono- ili biciklični aromatski heterociklil, heterocikliloksi,heterocikliltio, heterociklilsulfinil, heterociklilsulfonil, heterociklilamino, N-alkil-N-heterociklilamino, N-cikloalkil-N-heterocikloilamino, heterociklilkarbonil, heterociklilalkiloksi, heterociklilalkiltio, heterociklilalkilsulfinil, heterociklilamlkilsulfonil, heterociklilalkilamino, N-alkil-N-heterociklilaminoalkil, N-cikloalkil-N-heterociklilaminoalkil, (prethodno navedeni heterociklički dijelovi se odnose na mono-ili bicikličke aromatske spojeve), karboksil, alkiloksikarbonil, -NraRb ili -CO-NraRb u kojima Ra i Rb su u skladu s prethodno navedenom definicijom za R2, ili na drugi način R°3 predstavlja -CR'b=CR'c-R'a u kojem je R'a fenil, fenilalkil, heterociklil ili heterociklilalkil u kojem heterociklički dio predstavlja mono- ili biciklički aromatski spoj,fenoksialkil, feniltioalkil, fenilsulfinilalkil, fenilsulfonilalkil, fenilaminoalkil, N-alkil-N-fenilaminoalkil, heterocikliloksialkil, heterocikliltioalkil, heterociklilsulfinilalkil, heterociklilsulfonilalkil, heterociklilaminoalkil, N-alkil-N-heterociklilaminoalkil, heterocikliltio, heterociklilsulfinil, heterociklilsulfonil, (prethodno navedeni heterociklički dijelovi predstavljaju mono- ili biciklički aromatski spoj), feniltio, fenilsulfinil, fenilsulfonil, te u kojima R'b i R'c predstavljaju vodik, alkil ili cikloalkil, ili na drugi način R°3 predstavlja radikal -C≡C-Rd u kojem Rd predstavlja alkil, fenil, fenilalkil, fenoksialkil, feniltioalkil, N-alkil-N-fenilaminoalkil, mono- ili biciklički aromatski heterociklil, heterociklilalkil, heterocikliloksialkil, heterocikliltioalkil, heterociklilaminoalkil, N-alkil-N-heterociklilaminoalkil, (prethodno navedeni heterociklički dijelovi predstavljaju mono- ili biciklički aromatski spoj), ili na drugi način R°3 predstavlja -CF2-fenil ili mono- ili biciklički aromatski –CF2-heterociklilni radikal,
Y predstavlja radikal >CH-Re u kojem Re predstavlja vodik, fluoro, hidroksil, alkiloksi, cikloalkiloksi, karbonil, alkiloksikarbonil, cikloalkiloksikarbonil, -NRaRb ili -CO-NraRb u kojem Ra i Rb su u skladu s prethodno navedenom definicijom za R2, ili jedan predstavlja atom vodika, a drugi je alkiloksikarbonil, akril, cikloalkilkarbonil, benzoil ili heterociklilkarbonilni radikal u kojem je heterociklički dio mono- ili biciklički aromatski spoj, ili na drugi način Y predstavlja difluorometilen, karbonil, hidroksiiminometilen, alkiloksiiminometilen ili cikloalkiloksiiminometilenski radikal ili l,1-ciklo-alkilenski radikal koji sadrži 3 do 6 atoma ugljika, a
n je cijeli broj od 0 do 4,
i podrazumijeva se da fenil, benzil, benzoil ili heterociklilni radikali ili prethodno navedeni dijelovi mogu po izboru biti supstituirani na prstenu s 1 do 4 supstituenata odabrana između halogena, hidroksi, alkila, alkiloksi, alkiloksialkila, haloalkila, trifluorometila, trifluorometoksi, trifluorometiltio, karbonila, alkiloksikarbonila, cijano, alkilamino, -NRaRb u kojem Ra i Rb su u skladu s prethodno navedenom definicijom, fenil, hidroksialkil, alkiltioalkil, alkilsulfinilalkil i alkilsulfonilalkil, te
se smatra da alkilni ili acilni radikali i dijelovi sadrže (osim gdje je izričito navedeno) l do 10 atoma ugljika u ravnom ili razgranatom lancu, te da cikloalkilni radikali sadrže od 3 do 6 atoma ugljika u njihovim enantiomerskim ili
dijastereoizomerskim oblicima ili smjese navedenih oblika, i/ili, gdje je prikladno, dolaze u njihovim sin ili anti oblicima ili njihovim smjesama, kao i u obliku njihovih soli.
2. Heterociklilalkilpiperidinski derivat u skladu sa zahtjevom 1, naznačen time, da od nabrojenih X1, X2, X3, X4 i X5, odnosno, >C-R'1 do >C-R'5 najviše jedan predstavlja atom dušika.
R1, R'1, R'2, R'3, R'4 i R'5 su identični ili različiti, a predstavljaju vodik ili halogeni atom ili alkil, ili alkoksi radikal, ili predstavljaju metilenski radikal supstituiran s alkoksi,
R2 predstavlja hidroksimetil, alkil koji sadrži od 1 do 2 atoma ugljika supstituiranih s karboksilom, ili alkiloksikarbonilom,
R3 predstavlja alk-R°3 radikal u kojem alk označava alkilni radikal i R°3 predstavlja vodik, cikloalkil, cikloalkiltio, fenoksi, feniltio, fenilamino, heterocikliloksi ili heterocikliltio ili na drugi način, R°3 predstavlja -CR'b=CR'c-R'a u kojem je R'a fenil, te u kojem R'b i R'c predstavljaju vodik,
Y predstavlja radikal >CH-Re u kojem Re predstavlja vodik, fluoro ili hidroksil,
n je cijeli broj između 2 i 3,
a podrazumijeva se da fenilni, ili heterociklilni radikali ili prethodno navedeni dijelovi mogu po izboru biti supstituirani na prstenu s 1 do 4 halogena, a smatra se da alkilni ili acilni radikali i dijelovi sadrže (osim gdje je izričito navedeno) 1 do 10 atoma ugljika u ravnom ili razgranatom lancu, te da cikloalkilni radikali sadrže od 3 do 6 atoma ugljika u njihovim enantiomerskim ili dijastereoizomerskim oblicima ili smjesama navedenih oblika, i/ili, gdje je prikladno, dolaze u njihovim sin ili anti oblicima ili njihovim smjesama, kao i u obliku njihovih soli.
3. Heterociklilalkilpiperidinski derivat u skladu sa zahtjevom 1, naznačen time, da predstavlja 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(tien-2-il)tioetil]piperidin-4-karboksilnu kiselinu, kao i njezine soli.
4. Heterociklilalkilpiperidinski derivat u skladu sa zahtjevom 1, naznačen time, da predstavlja 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-[2-(3,5-difluorofenoksi)-etil]piperidin-4-karboksilnu kiselinu, kao i njezine soli.
5. Heterociklilalkilpiperidinski derivat u skladu sa zahtjevom 1, naznačen time, da predstavlja 4-[3-(3-kloro-6-metoksikinolin-4-il)propil]-1-(2-tiazol-2-tioetil)piperidin-4-karboksilnu kiselinu, kao i njezine soli.
6. Heterociklilalkilpiperidinski derivat u skladu sa zahtjevom 1, naznačen time, da predstavlja 1-(2-ciklopentiltioetil)-4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]piperidin-4-karboksilnu kiselinu, kao i njezine soli.
7. Heterociklilalkilpiperidinski derivat u skladu sa zahtjevom 1, naznačen time, da predstavlja 4-[3-(3-fluoro-6-metoksikinolin-4-il)propil]-1-(3-fenilalil)piperidin-4-karboksilnu kiselinu, kao i njezine soli.
8. Postupak pripravljanja heterociklilalkilpiperidinskog derivata u skladu sa zahtjevom 1, naznačenog time, da je lanac R3, u skladu s definicijom iz zahtjeva l, vezan na heterociklilalkil-piperidinski derivat opće formule:
[image]
u kojoj su X1, X2, X3, X4, X5, R1, R2, Y i n u skladu sa prethodno navedenom definicijom, R2 je zaštićen kada nosi karboksilni ili amino radikal, a po izboru slijedi uklanjanje zaštitnog radikala kiseline ili amina, odvajanje enantiomeričnih ili dijastereoizomeričnih oblika i/ili, ako je prikladno, sin ili anti oblika, te konverzija dobivenog produkta u sol.
9. Postupak u skladu sa zahtjevom 8, naznačen time, da se vezanje R3 sa piperidinom izvodi djelovanjem derivata opće formule:
R3-X
u kojem je R3 u skladu s gore navedenom definicijom, a X predstavlja halogeni atom, metilsulfonilni radikal, trifluorometilsulofonilni radikal ili p-toluensulfonilni radikal.
10. Postupak u skladu s bilo kojim od zahtjeva 8 i 9, naznačen -time, da se u slučaju kada R3 predstavlja radikal -alk-R°a u kojem alk predstavlja alkilni radikal, a R°a predstavlja radikal -C=C-Rd u kojem je Rd fenil, fenilalkil, heterociklil ili mono- ili biciklični aromatski heterociklil-alkil, reakcija izvodi po mogućnosti vezanjem alkinilnog halida: HC≡C-alk-X u kojem je alk u skladu s prethodno navedenom definicijom i X predstavlja halogeni atom, a zatim supstitucijom lanca sa fenilnim, fenilalkilnim, heterociklilnim ili heterociklilalkilnim radikalom.
11. Postupak u skladu sa bilo kojim od zahtjeva 8 i 9, naznačen time, da se u slučaju kada R3 predstavlja radikal -alk- R°3,u kojem alk predstavlja alkilni radikal, a R°3 predstavlja fenoksi, feniltio, fenilamino, heterocikliloksi, heterocikliltio ili heterociklilamino radikal, u kojem je heterociklilni dio aromatski, reakcija izvodi postupnom izgradnjom lanca, prvo kondenziranjem lanca HO-alk-X, u kojem X predstavlja halogeni atom, a zatim pretvorbom hidroksialkilnog lanca pretvorenog u haloalkilni, metansulfonilalkilni ili p-toluensulfonilalkilni lanac, te na kraju reakcijom u bazičnom mediju sa aromatskim derivatom ili strukturom Ar-ZH u kojoj Ar predstavlja fenil ili aromatski heterociklilni radikal, a Z je atom sumpora, kisika ili dušika.
12. Farmaceutski pripravak, naznačen time, da sadrži najmanje jedan derivat u skladu sa zahtjevom l, u čistom obliku ili u kombinaciji s jednim ili više odgovarajućih i farmaceutski prihvatljivih diluensa i/ili adjuvansa.
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FR0014738A FR2816618B1 (fr) | 2000-11-15 | 2000-11-15 | Derives heterocyclylalcoyl piperidine, leur preparation et les compositions qui les contiennent |
PCT/FR2001/003559 WO2002040474A2 (fr) | 2000-11-15 | 2001-11-14 | Derives heterocyclylalcoyl piperidine et leur application comme antimicrobiens |
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PL366335A1 (en) | 2000-07-26 | 2005-01-24 | Smithkline Beecham P.L.C. | Aminopiperidine quinolines and their azaisosteric analogues with antibacterial activity |
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 |
GB0118238D0 (en) * | 2001-07-26 | 2001-09-19 | Smithkline Beecham Plc | Medicaments |
EP1470131A2 (en) | 2002-01-29 | 2004-10-27 | 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 |
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 |
GB0217294D0 (en) * | 2002-07-25 | 2002-09-04 | Glaxo Group Ltd | Medicaments |
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 |
DE10256405A1 (de) * | 2002-12-02 | 2004-06-17 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Neue Verbindungen, die Topoisomerase IV inhibieren |
ES2340484T3 (es) | 2002-11-05 | 2010-06-04 | Glaxo Group Limited | Agentes antibacterianos. |
EP1567520B1 (en) | 2002-12-04 | 2008-10-15 | Glaxo Group Limited | Quinolines and nitrogenated derivatives thereof and their use as antibacterial agents |
US7232833B2 (en) | 2003-03-28 | 2007-06-19 | Novexel | 4-substituted quinoline derivatives, method and intermediates for their preparation and pharmaceutical compositions containing them |
FR2852954B1 (fr) * | 2003-03-28 | 2006-07-14 | Aventis Pharma Sa | Derives de quinoleines-4-substituees, leurs procede et intermediaires de preparation et les compositions pharmaceutiques qui les contiennent |
FR2862301B1 (fr) * | 2003-11-17 | 2007-12-21 | Aventis Pharma Sa | Nouveau procede de preparation de quinoleines 3-fluorees |
FR2867472B1 (fr) * | 2004-03-12 | 2008-07-18 | Aventis Pharma Sa | Derives de quinoleines-4-substituees, leurs procede et intermediaires de preparation et les compositions pharmaceutiques qui les contiennent |
WO2006081182A2 (en) | 2005-01-25 | 2006-08-03 | Glaxo Group Limited | Antibacterial agents |
US7605169B2 (en) | 2005-01-25 | 2009-10-20 | Glaxo Group Limited | Antibacterial agents |
JP2008528586A (ja) | 2005-01-25 | 2008-07-31 | グラクソ グループ リミテッド | 抗菌剤 |
EP1845995A4 (en) | 2005-01-25 | 2010-03-03 | Glaxo Group Ltd | ANTIBACTERIAL AGENTS |
CN101166730A (zh) | 2005-03-01 | 2008-04-23 | 惠氏公司 | 噌啉化合物及其作为肝x受体调节剂的用途 |
MY150958A (en) | 2005-06-16 | 2014-03-31 | Astrazeneca Ab | Compounds for the treatment of multi-drug resistant bacterial infections |
ES2376488T3 (es) | 2006-01-26 | 2012-03-14 | Actelion Pharmaceuticals Ltd. | Antibióticos de tetrahidropirano. |
ATE481406T1 (de) | 2006-04-06 | 2010-10-15 | Glaxo Group Ltd | Pyrrolochinoxalinonderivate als antibakterielle mittel |
EP1992628A1 (en) | 2007-05-18 | 2008-11-19 | Glaxo Group Limited | Derivatives and analogs of N-ethylquinolones and N-ethylazaquinolones |
AR067008A1 (es) | 2007-06-15 | 2009-09-30 | Actelion Pharmaceuticals Ltd | Derivados 3- amino-6-(1- amino - etil)-tetrahidropirano |
EP2080761A1 (en) | 2008-01-18 | 2009-07-22 | Glaxo Group Limited | Compounds |
JP2012505866A (ja) | 2008-10-17 | 2012-03-08 | グラクソ グループ リミテッド | 抗菌剤として使用される三環式窒素化合物 |
WO2010081874A1 (en) | 2009-01-15 | 2010-07-22 | Glaxo Group Limited | Naphthyridin-2 (1 h)-one compounds useful as antibacterials |
CN107163038B (zh) * | 2012-08-15 | 2020-07-28 | 葛兰素集团有限公司 | 化学方法 |
SG11201700566SA (en) | 2014-08-22 | 2017-03-30 | Glaxosmithkline Ip Dev Ltd | Tricyclic nitrogen containing compounds for treating neisseria gonorrhoea infection |
WO2016138988A1 (en) * | 2015-03-02 | 2016-09-09 | University Of Copenhagen | Piperazine inhibitors of bacterial gyrase and topoisomerase iv |
UY36851A (es) | 2015-08-16 | 2017-03-31 | Glaxosmithkline Ip Dev Ltd | Compuestos para uso en aplicaciones antibacterianas |
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NL7908031A (nl) | 1979-11-01 | 1981-06-01 | Acf Chemiefarma Nv | Nieuwe chinolinederivaten en farmaceutische preparaten die een dergelijke verbinding bevatten, alsmede werk- wijze voor het bereiden van deze verbindingen. |
JPH0239546A (ja) | 1988-07-29 | 1990-02-08 | Origin Electric Co Ltd | 混成集積回路の製造方法 |
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AU2437900A (en) * | 1999-01-20 | 2000-08-07 | Smithkline Beecham Plc | Piperidinylquinolines as protein tyrosine kinase inhibitors |
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