JP2005511743A5 - - Google Patents
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- Publication number
- JP2005511743A5 JP2005511743A5 JP2003551131A JP2003551131A JP2005511743A5 JP 2005511743 A5 JP2005511743 A5 JP 2005511743A5 JP 2003551131 A JP2003551131 A JP 2003551131A JP 2003551131 A JP2003551131 A JP 2003551131A JP 2005511743 A5 JP2005511743 A5 JP 2005511743A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- oxo
- quinoline
- piperidinyl
- fluoro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000003839 salts Chemical class 0.000 claims 197
- -1 1-aminocyclohexylcarbonyl Chemical group 0.000 claims 80
- 239000002253 acid Chemical group 0.000 claims 52
- 239000005973 Carvone Substances 0.000 claims 50
- 239000000203 mixture Substances 0.000 claims 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 14
- 238000000034 method Methods 0.000 claims 14
- 230000003287 optical effect Effects 0.000 claims 13
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 12
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 claims 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 238000000113 differential scanning calorimetry Methods 0.000 claims 12
- 229940050410 gluconate Drugs 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 9
- 238000004458 analytical method Methods 0.000 claims 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 239000003960 organic solvent Substances 0.000 claims 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 208000015181 infectious disease Diseases 0.000 claims 6
- 238000002360 preparation method Methods 0.000 claims 6
- 230000009885 systemic effect Effects 0.000 claims 6
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 5
- SSCLELDZYWNJJT-QLJPJBMISA-N 1-cyclopropyl-6-fluoro-7-[(3r,4r)-4-hydroxy-3-methylpiperidin-1-yl]-8-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound C1C[C@@H](O)[C@H](C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1C SSCLELDZYWNJJT-QLJPJBMISA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 150000001413 amino acids Chemical class 0.000 claims 4
- 125000001589 carboacyl group Chemical group 0.000 claims 4
- 239000000843 powder Substances 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 3
- WPBQEWYKGUXFAT-UHFFFAOYSA-N 1-cyclopropyl-7-[3,3-dimethyl-4-(phenylmethoxycarbonylamino)piperidin-1-yl]-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=CN2C3CC3)=O)=C2C(OC)=C1N(CC1(C)C)CCC1NC(=O)OCC1=CC=CC=C1 WPBQEWYKGUXFAT-UHFFFAOYSA-N 0.000 claims 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 3
- SOWSVRBSHHQLAB-UHFFFAOYSA-N 5-amino-7-(4-amino-3,3-dimethylpiperidin-1-yl)-1-cyclopropyl-6-fluoro-8-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C(N)C(C(C(C(O)=O)=CN2C3CC3)=O)=C2C(C)=C1N1CCC(N)C(C)(C)C1 SOWSVRBSHHQLAB-UHFFFAOYSA-N 0.000 claims 3
- DWHXCQMDSVTVCU-UHFFFAOYSA-N 7-(4-amino-3,3-dimethylpiperidin-1-yl)-1,8-diethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=CN2CC)=O)=C2C(CC)=C1N1CCC(N)C(C)(C)C1 DWHXCQMDSVTVCU-UHFFFAOYSA-N 0.000 claims 3
- BDSBSELVBOBYOQ-UHFFFAOYSA-N 7-(4-amino-3,3-dimethylpiperidin-1-yl)-1-(2,4-difluorophenyl)-6-fluoro-8-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=CN2C=3C(=CC(F)=CC=3)F)=O)=C2C(C)=C1N1CCC(N)C(C)(C)C1 BDSBSELVBOBYOQ-UHFFFAOYSA-N 0.000 claims 3
- MZJYKRXJUVVRLL-UHFFFAOYSA-N 7-(4-amino-3,3-dimethylpiperidin-1-yl)-1-(2,4-difluorophenyl)-8-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=CN2C=3C(=CC(F)=CC=3)F)=O)=C2C(CC)=C1N1CCC(N)C(C)(C)C1 MZJYKRXJUVVRLL-UHFFFAOYSA-N 0.000 claims 3
- AALWVRXNONLKQH-UHFFFAOYSA-N 7-(4-amino-3,3-dimethylpiperidin-1-yl)-1-ethyl-6-fluoro-8-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound CC1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCC(N)C(C)(C)C1 AALWVRXNONLKQH-UHFFFAOYSA-N 0.000 claims 3
- FKQVCNIEJCPZQT-MEBBXXQBSA-N 7-[(3r,4r)-4-amino-3-methylpiperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=CN2C3CC3)=O)=C2C(OC)=C1N1CC[C@@H](N)[C@H](C)C1 FKQVCNIEJCPZQT-MEBBXXQBSA-N 0.000 claims 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- MGGWXOOXFIXMCF-UHFFFAOYSA-N benzyl 4-amino-3,3-dimethylpiperidine-1-carboxylate Chemical compound C1CC(N)C(C)(C)CN1C(=O)OCC1=CC=CC=C1 MGGWXOOXFIXMCF-UHFFFAOYSA-N 0.000 claims 3
- 229910052796 boron Inorganic materials 0.000 claims 3
- 239000013522 chelant Substances 0.000 claims 3
- OKZIUSOJQLYFSE-UHFFFAOYSA-N difluoroboron Chemical compound F[B]F OKZIUSOJQLYFSE-UHFFFAOYSA-N 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 230000003301 hydrolyzing effect Effects 0.000 claims 3
- UPXRTDGIBOVLGV-UHFFFAOYSA-N tert-butyl n-(3,3-dimethylpiperidin-4-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1CCNCC1(C)C UPXRTDGIBOVLGV-UHFFFAOYSA-N 0.000 claims 3
- BIRRFYKJOVTPGR-BDJLRTHQSA-N 1,8-diethyl-6-fluoro-7-[(3r,4r)-4-hydroxy-3-methylpiperidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=CN2CC)=O)=C2C(CC)=C1N1CC[C@@H](O)[C@H](C)C1 BIRRFYKJOVTPGR-BDJLRTHQSA-N 0.000 claims 2
- SKJVBTKTRDJINY-MPBGBICISA-N 1-(2,4-difluorophenyl)-8-ethyl-6-fluoro-7-[(3r,4r)-4-hydroxy-3-methylpiperidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=CN2C=3C(=CC(F)=CC=3)F)=O)=C2C(CC)=C1N1CC[C@@H](O)[C@H](C)C1 SKJVBTKTRDJINY-MPBGBICISA-N 0.000 claims 2
- BXENYJFWTOWMLO-UHFFFAOYSA-N 1-benzyl-3-ethyl-n,3-dimethylpiperidin-4-amine Chemical compound C1CC(NC)C(CC)(C)CN1CC1=CC=CC=C1 BXENYJFWTOWMLO-UHFFFAOYSA-N 0.000 claims 2
- SAMHFFGNBBJKBM-UHFFFAOYSA-N 1-cyclopropyl-7-[4-(dimethylamino)-3-methylpiperidin-1-yl]-6-fluoro-8-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound C1CC(N(C)C)C(C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1C SAMHFFGNBBJKBM-UHFFFAOYSA-N 0.000 claims 2
- CKIYQWIJAIZFGL-PIGZYNQJSA-N 1-cyclopropyl-8-ethyl-6-fluoro-7-[(3r,4r)-4-hydroxy-3-methylpiperidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=CN2C3CC3)=O)=C2C(CC)=C1N1CC[C@@H](O)[C@H](C)C1 CKIYQWIJAIZFGL-PIGZYNQJSA-N 0.000 claims 2
- SVZYXCYFQWYNKL-MEBBXXQBSA-N 1-ethyl-6-fluoro-7-[(3r,4r)-4-hydroxy-3-methylpiperidin-1-yl]-8-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound CC1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CC[C@@H](O)[C@H](C)C1 SVZYXCYFQWYNKL-MEBBXXQBSA-N 0.000 claims 2
- QNNHERLTFGYZFS-BDJLRTHQSA-N 7-[(3r,4r)-4-amino-3-methylpiperidin-1-yl]-1,8-diethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=CN2CC)=O)=C2C(CC)=C1N1CC[C@@H](N)[C@H](C)C1 QNNHERLTFGYZFS-BDJLRTHQSA-N 0.000 claims 2
- BCVAMDPUKLPDNZ-ADLMAVQZSA-N 7-[(3r,4r)-4-amino-3-methylpiperidin-1-yl]-1-(2,4-difluorophenyl)-6-fluoro-8-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound C1C[C@@H](N)[C@H](C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C=3C(=CC(F)=CC=3)F)C2=C1C BCVAMDPUKLPDNZ-ADLMAVQZSA-N 0.000 claims 2
- QHCUWXGKRRWDPY-CWTRNNRKSA-N 7-[(3r,4r)-4-amino-3-methylpiperidin-1-yl]-1-(2,4-difluorophenyl)-8-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=CN2C=3C(=CC(F)=CC=3)F)=O)=C2C(CC)=C1N1CC[C@@H](N)[C@H](C)C1 QHCUWXGKRRWDPY-CWTRNNRKSA-N 0.000 claims 2
- CGOYMYAGVNRAGM-XGAJLMLQSA-N 7-[(3r,4r)-4-amino-3-methylpiperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methyl-4-oxoquinoline-3-carboxylic acid;hydrochloride Chemical compound Cl.C1C[C@@H](N)[C@H](C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1C CGOYMYAGVNRAGM-XGAJLMLQSA-N 0.000 claims 2
- NDOZWLIOAXKRQZ-MEBBXXQBSA-N 7-[(3r,4r)-4-amino-3-methylpiperidin-1-yl]-1-ethyl-6-fluoro-8-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound CC1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CC[C@@H](N)[C@H](C)C1 NDOZWLIOAXKRQZ-MEBBXXQBSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- KSXRRCOGLFVKJR-SJKOYZFVSA-N C1(CC1)N1C=C(C(C2=CC(=C(C(=C12)C)N1C[C@H]([C@@H](CC1)O)CC)F)=O)C(=O)O Chemical compound C1(CC1)N1C=C(C(C2=CC(=C(C(=C12)C)N1C[C@H]([C@@H](CC1)O)CC)F)=O)C(=O)O KSXRRCOGLFVKJR-SJKOYZFVSA-N 0.000 claims 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 238000002441 X-ray diffraction Methods 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 150000001350 alkyl halides Chemical class 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 125000000539 amino acid group Chemical group 0.000 claims 2
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims 2
- IDONWUALARWGFR-UHFFFAOYSA-N benzyl 3,3-dimethyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]piperidine-1-carboxylate Chemical compound C1C(C)(C)C(NC(=O)OC(C)(C)C)CCN1C(=O)OCC1=CC=CC=C1 IDONWUALARWGFR-UHFFFAOYSA-N 0.000 claims 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- SHTUTXIOXCCHBW-UHFFFAOYSA-N ethyl 4-amino-3,5-dimethylpiperidine-1-carboxylate Chemical compound CCOC(=O)N1CC(C)C(N)C(C)C1 SHTUTXIOXCCHBW-UHFFFAOYSA-N 0.000 claims 2
- SKSJFDIIYVNVPZ-UHFFFAOYSA-N ethyl n-(3,3-dimethylpiperidin-4-yl)carbamate Chemical compound CCOC(=O)NC1CCNCC1(C)C SKSJFDIIYVNVPZ-UHFFFAOYSA-N 0.000 claims 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- HAUKUCGBYWFHFC-GDBMZVCRSA-N tert-butyl n-[(3r,4r)-1-benzyl-3-methylpiperidin-4-yl]carbamate Chemical compound C1C[C@@H](NC(=O)OC(C)(C)C)[C@H](C)CN1CC1=CC=CC=C1 HAUKUCGBYWFHFC-GDBMZVCRSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims 1
- CTPZKIHDODPEDW-UHFFFAOYSA-N 1,8-diethyl-6-fluoro-7-(4-hydroxy-3,3-dimethylpiperidin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=CN2CC)=O)=C2C(CC)=C1N1CCC(O)C(C)(C)C1 CTPZKIHDODPEDW-UHFFFAOYSA-N 0.000 claims 1
- UTSTUTABZSMOOJ-UHFFFAOYSA-N 1,8-diethyl-6-fluoro-7-(4-hydroxypiperidin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=CN2CC)=O)=C2C(CC)=C1N1CCC(O)CC1 UTSTUTABZSMOOJ-UHFFFAOYSA-N 0.000 claims 1
- SSQOZCFPOXGDLG-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-6-fluoro-7-(4-hydroxy-3,3-dimethylpiperidin-1-yl)-8-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=CN2C=3C(=CC(F)=CC=3)F)=O)=C2C(C)=C1N1CCC(O)C(C)(C)C1 SSQOZCFPOXGDLG-UHFFFAOYSA-N 0.000 claims 1
- YIIYDJHBXHVWFJ-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-6-fluoro-7-(4-hydroxypiperidin-1-yl)-8-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=CN2C=3C(=CC(F)=CC=3)F)=O)=C2C(C)=C1N1CCC(O)CC1 YIIYDJHBXHVWFJ-UHFFFAOYSA-N 0.000 claims 1
- BRCVXCLSBOTCIT-NSPYISDASA-N 1-(2,4-difluorophenyl)-6-fluoro-7-[(3r,4r)-4-hydroxy-3-methylpiperidin-1-yl]-8-methyl-4-oxoquinoline-3-carboxylic acid Chemical class C1C[C@@H](O)[C@H](C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C=3C(=CC(F)=CC=3)F)C2=C1C BRCVXCLSBOTCIT-NSPYISDASA-N 0.000 claims 1
- JWOYQZDQRBLMSR-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-8-ethyl-6-fluoro-7-(4-hydroxy-3,3-dimethylpiperidin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=CN2C=3C(=CC(F)=CC=3)F)=O)=C2C(CC)=C1N1CCC(O)C(C)(C)C1 JWOYQZDQRBLMSR-UHFFFAOYSA-N 0.000 claims 1
- GZPKHJXGWSSWHK-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-8-ethyl-6-fluoro-7-(4-hydroxypiperidin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=CN2C=3C(=CC(F)=CC=3)F)=O)=C2C(CC)=C1N1CCC(O)CC1 GZPKHJXGWSSWHK-UHFFFAOYSA-N 0.000 claims 1
- DQXXKLYTOYMITI-UHFFFAOYSA-N 1-(dimethylamino)piperidin-2-one Chemical compound CN(C)N1CCCCC1=O DQXXKLYTOYMITI-UHFFFAOYSA-N 0.000 claims 1
- HERVTRCHMAOCNM-UHFFFAOYSA-N 1-benzyl-3,3-diethylpiperidin-4-amine Chemical compound C1CC(N)C(CC)(CC)CN1CC1=CC=CC=C1 HERVTRCHMAOCNM-UHFFFAOYSA-N 0.000 claims 1
- ZSWUAMLORPBSTM-UHFFFAOYSA-N 1-benzyl-3,3-dimethylpiperidin-4-amine Chemical compound C1CC(N)C(C)(C)CN1CC1=CC=CC=C1 ZSWUAMLORPBSTM-UHFFFAOYSA-N 0.000 claims 1
- GYHFWENUVFMIBE-UHFFFAOYSA-N 1-benzyl-3,5-diethyl-3-methylpiperidin-4-amine Chemical compound C1C(C)(CC)C(N)C(CC)CN1CC1=CC=CC=C1 GYHFWENUVFMIBE-UHFFFAOYSA-N 0.000 claims 1
- TYLFZMBNLFRBNH-UHFFFAOYSA-N 1-benzyl-3,5-diethylpiperidin-4-amine Chemical compound C1C(CC)C(N)C(CC)CN1CC1=CC=CC=C1 TYLFZMBNLFRBNH-UHFFFAOYSA-N 0.000 claims 1
- HYERCZPARKEXQI-UHFFFAOYSA-N 1-benzyl-3-ethyl-3,5-dimethylpiperidin-4-amine Chemical compound C1C(C)C(N)C(CC)(C)CN1CC1=CC=CC=C1 HYERCZPARKEXQI-UHFFFAOYSA-N 0.000 claims 1
- XZUJMFOTXYKCTA-UHFFFAOYSA-N 1-benzyl-3-ethyl-3-methylpiperidin-4-amine Chemical compound C1CC(N)C(CC)(C)CN1CC1=CC=CC=C1 XZUJMFOTXYKCTA-UHFFFAOYSA-N 0.000 claims 1
- BOZBHPFGGMLULS-UHFFFAOYSA-N 1-benzyl-n-cyclopropyl-3-ethyl-3-methylpiperidin-4-amine Chemical compound C1CC(NC2CC2)C(CC)(C)CN1CC1=CC=CC=C1 BOZBHPFGGMLULS-UHFFFAOYSA-N 0.000 claims 1
- SJZKULRDWHPHGG-UHFFFAOYSA-N 1-benzylpiperidin-4-one Chemical compound C1CC(=O)CCN1CC1=CC=CC=C1 SJZKULRDWHPHGG-UHFFFAOYSA-N 0.000 claims 1
- YCKFHFFSDLPAKF-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-(4-hydroxy-3,3,5-trimethylpiperidin-1-yl)-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=CN2C3CC3)=O)=C2C(OC)=C1N1CC(C)C(O)C(C)(C)C1 YCKFHFFSDLPAKF-UHFFFAOYSA-N 0.000 claims 1
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- 125000004442 acylamino group Chemical group 0.000 claims 1
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- LBFRWJZMFMQWTF-UHFFFAOYSA-N ethyl 4-(cyclopropylamino)-3-methylpiperidine-1-carboxylate Chemical compound CC1CN(C(=O)OCC)CCC1NC1CC1 LBFRWJZMFMQWTF-UHFFFAOYSA-N 0.000 claims 1
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- HBWVHKLBIDCOHJ-UHFFFAOYSA-N ethyl 4-(ethylamino)-3-methylpiperidine-1-carboxylate Chemical compound CCNC1CCN(C(=O)OCC)CC1C HBWVHKLBIDCOHJ-UHFFFAOYSA-N 0.000 claims 1
- LMBHFRKOOBDTIT-UHFFFAOYSA-N ethyl 4-amino-3,3-dimethylpiperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(N)C(C)(C)C1 LMBHFRKOOBDTIT-UHFFFAOYSA-N 0.000 claims 1
- LVIDFINDEFXGRY-UHFFFAOYSA-N ethyl 4-amino-3-methylpiperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(N)C(C)C1 LVIDFINDEFXGRY-UHFFFAOYSA-N 0.000 claims 1
- LIIUTFVNVAJAKG-UHFFFAOYSA-N ethyl n-(1-benzyl-3,3-dimethylpiperidin-4-yl)carbamate Chemical compound C1C(C)(C)C(NC(=O)OCC)CCN1CC1=CC=CC=C1 LIIUTFVNVAJAKG-UHFFFAOYSA-N 0.000 claims 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 229940124307 fluoroquinolone Drugs 0.000 claims 1
- 125000003147 glycosyl group Chemical group 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 230000026045 iodination Effects 0.000 claims 1
- 238000006192 iodination reaction Methods 0.000 claims 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- FHWXHXRRCMIUIK-UHFFFAOYSA-N n,3,3-trimethylpiperidin-4-amine Chemical compound CNC1CCNCC1(C)C FHWXHXRRCMIUIK-UHFFFAOYSA-N 0.000 claims 1
- YPSXMDISEKEGKH-UHFFFAOYSA-N n,3,5-trimethylpiperidin-4-amine Chemical compound CNC1C(C)CNCC1C YPSXMDISEKEGKH-UHFFFAOYSA-N 0.000 claims 1
- PAIUOUOHLLEEEP-UHFFFAOYSA-N n,3-dimethylpiperidin-4-amine Chemical compound CNC1CCNCC1C PAIUOUOHLLEEEP-UHFFFAOYSA-N 0.000 claims 1
- LTVSDBIRNKOKKA-UHFFFAOYSA-N n,n,3,3-tetramethylpiperidin-4-amine Chemical compound CN(C)C1CCNCC1(C)C LTVSDBIRNKOKKA-UHFFFAOYSA-N 0.000 claims 1
- JCIHJQGIECMFCJ-UHFFFAOYSA-N n,n,3,5-tetramethylpiperidin-4-amine Chemical compound CC1CNCC(C)C1N(C)C JCIHJQGIECMFCJ-UHFFFAOYSA-N 0.000 claims 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 claims 1
- TWXWNGCNYWNMJR-UHFFFAOYSA-N n-(1-benzyl-3,3-dimethylpiperidin-4-yl)acetamide Chemical compound C1C(C)(C)C(NC(=O)C)CCN1CC1=CC=CC=C1 TWXWNGCNYWNMJR-UHFFFAOYSA-N 0.000 claims 1
- UQGJFKSHEAMPKR-UHFFFAOYSA-N n-(3,3-dimethylpiperidin-4-yl)acetamide Chemical compound CC(=O)NC1CCNCC1(C)C UQGJFKSHEAMPKR-UHFFFAOYSA-N 0.000 claims 1
- CLMPJOHICGFIQG-UHFFFAOYSA-N n-benzyl-3,3-dimethylpiperidin-4-amine Chemical compound CC1(C)CNCCC1NCC1=CC=CC=C1 CLMPJOHICGFIQG-UHFFFAOYSA-N 0.000 claims 1
- GLXSANUPYLXYBF-UHFFFAOYSA-N n-cyclopropyl-3,3-dimethylpiperidin-4-amine Chemical compound CC1(C)CNCCC1NC1CC1 GLXSANUPYLXYBF-UHFFFAOYSA-N 0.000 claims 1
- PZQUEAMFJFUJGG-UHFFFAOYSA-N n-cyclopropyl-3,5-dimethylpiperidin-4-amine Chemical compound CC1CNCC(C)C1NC1CC1 PZQUEAMFJFUJGG-UHFFFAOYSA-N 0.000 claims 1
- SMIRTKHVMVGXDQ-UHFFFAOYSA-N n-cyclopropyl-3-ethyl-3-methylpiperidin-4-amine Chemical compound CCC1(C)CNCCC1NC1CC1 SMIRTKHVMVGXDQ-UHFFFAOYSA-N 0.000 claims 1
- OSUUPRKVGLPDBB-UHFFFAOYSA-N n-cyclopropyl-3-ethylpiperidin-4-amine Chemical compound CCC1CNCCC1NC1CC1 OSUUPRKVGLPDBB-UHFFFAOYSA-N 0.000 claims 1
- CAZWZOFUXCIGSR-UHFFFAOYSA-N n-cyclopropyl-3-methylpiperidin-4-amine Chemical compound CC1CNCCC1NC1CC1 CAZWZOFUXCIGSR-UHFFFAOYSA-N 0.000 claims 1
- WQXHWNIFQVJVSZ-UHFFFAOYSA-N n-ethyl-3,3-dimethylpiperidin-4-amine Chemical compound CCNC1CCNCC1(C)C WQXHWNIFQVJVSZ-UHFFFAOYSA-N 0.000 claims 1
- QDZDQKRSBWFIAK-UHFFFAOYSA-N n-ethyl-3,5-dimethylpiperidin-4-amine Chemical compound CCNC1C(C)CNCC1C QDZDQKRSBWFIAK-UHFFFAOYSA-N 0.000 claims 1
- AXIBJJFOGYUHHJ-UHFFFAOYSA-N n-ethyl-3-methylpiperidin-4-amine Chemical compound CCNC1CCNCC1C AXIBJJFOGYUHHJ-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 claims 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 claims 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- WJBJAZZZQBXWOQ-UHFFFAOYSA-N tert-butyl 3,3-dimethyl-4-(phenylmethoxycarbonylamino)piperidine-1-carboxylate Chemical compound CC1(C)CN(C(=O)OC(C)(C)C)CCC1NC(=O)OCC1=CC=CC=C1 WJBJAZZZQBXWOQ-UHFFFAOYSA-N 0.000 claims 1
- MNJCZOJFFXXZKR-UHFFFAOYSA-N tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(N)C(C)(C)C1 MNJCZOJFFXXZKR-UHFFFAOYSA-N 0.000 claims 1
- LHSNRJGZDUFKQT-RKDXNWHRSA-N tert-butyl n-[(3r,4r)-3-methylpiperidin-4-yl]carbamate Chemical compound C[C@@H]1CNCC[C@H]1NC(=O)OC(C)(C)C LHSNRJGZDUFKQT-RKDXNWHRSA-N 0.000 claims 1
- LHSNRJGZDUFKQT-BDAKNGLRSA-N tert-butyl n-[(3r,4s)-3-methylpiperidin-4-yl]carbamate Chemical compound C[C@@H]1CNCC[C@@H]1NC(=O)OC(C)(C)C LHSNRJGZDUFKQT-BDAKNGLRSA-N 0.000 claims 1
- 125000004385 trihaloalkyl group Chemical group 0.000 claims 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34116501P | 2001-12-13 | 2001-12-13 | |
| US10/128,996 US6964966B2 (en) | 2001-04-25 | 2002-04-23 | Generation triple-targeting, chiral, broad-spectrum antimicrobial 7-substituted piperidino-quinolone carboxylic acid derivatives, their preparation, compositions and use as medicaments |
| PCT/IN2002/000111 WO2002085886A2 (en) | 2001-04-25 | 2002-04-24 | Chiral, broad-spectrum antibacterial 7-substituted piperidino-quinolone carboxylic acid derivatives, their preparation and compositions |
| PCT/IN2002/000232 WO2003050107A1 (en) | 2001-12-13 | 2002-12-12 | New generation triple-targeting, chiral, broad-spectrum antimicrobial 7-substituted piperidino-quinolone carboxylic acid derivatives, their preparation, compositions and use as medicaments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005511743A JP2005511743A (ja) | 2005-04-28 |
| JP2005511743A5 true JP2005511743A5 (da) | 2006-01-19 |
Family
ID=27271958
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003551131A Abandoned JP2005511743A (ja) | 2001-12-13 | 2002-12-12 | 新世代の三重標的化したキラルな広域スペクトラム抗菌性の７位置換ピペリジノ−キノロンカルボン酸誘導体、その調製方法、組成物、および医薬としての使用 |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1453824A1 (da) |
| JP (1) | JP2005511743A (da) |
| AU (1) | AU2002361493A1 (da) |
| WO (1) | WO2003050107A1 (da) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005026145A2 (en) * | 2003-09-12 | 2005-03-24 | Warner-Lambert Company Llc | Quinolone antibacterial agents |
| EP1694667A2 (en) | 2003-11-20 | 2006-08-30 | Wockhardt Limited | Polymorphs of 1-cyclopropyl-6-fluoro-8-methoxy-7-(4-amino-3, 3-dimethylpiperidin-1-yl)-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid hydrochloride and mesalyte salts |
| DE102004035203A1 (de) | 2004-07-21 | 2006-02-16 | Bayer Healthcare Ag | Substituierte Chinolone |
| DE102005030524A1 (de) | 2005-06-30 | 2007-01-18 | Aicuris Gmbh & Co. Kg | Substituierte Chinolone II |
| DE102006005861A1 (de) | 2006-02-09 | 2007-08-23 | Aicuris Gmbh & Co. Kg | Substituierte Chinolone III |
| US7902227B2 (en) | 2007-07-27 | 2011-03-08 | Janssen Pharmaceutica Nv. | C-7 isoxazolinyl quinolone / naphthyridine derivatives useful as antibacterial agents |
| NZ584892A (en) | 2007-10-05 | 2012-06-29 | Cylene Pharmaceuticals Inc | Quinolone analogs and methods related thereto |
| US20100331546A1 (en) * | 2008-02-27 | 2010-12-30 | Sumitomo Chemical Company, Limited | Method for optical resolution of alkyl piperidin-3-yl carbamate and intermediate therefor |
| JP2009256337A (ja) * | 2008-03-26 | 2009-11-05 | Sumitomo Chemical Co Ltd | ピペリジン−３−イルカーバメート化合物の製造方法 |
| RU2547835C1 (ru) * | 2014-03-06 | 2015-04-10 | Федеральное государственное бюджетное учреждение науки Институт органического синтеза им. И.Я. Постовского Уральского отделения Российской академии наук | Азолоазиниевые соли фторхинолонов, обладающие антибактериальным и противовирусным действием |
| CN107949562B (zh) | 2015-06-09 | 2021-07-23 | 拜耳制药股份公司 | 毒蕈碱性m2受体的正性变构调节剂 |
| CA3005730A1 (en) | 2015-11-20 | 2017-05-26 | Senhwa Biosciences, Inc. | Combination therapy of tetracyclic quinolone analogs for treating cancer |
| US9957282B2 (en) | 2015-12-14 | 2018-05-01 | Senhwa Biosciences, Inc. | Crystalline forms of quinolone analogs and their salts |
| WO2018011017A1 (de) | 2016-07-11 | 2018-01-18 | Bayer Pharma Aktiengesellschaft | 7-substituierte 1-pyridyl-naphthyridin-3-carbonsäureamide und ihre verwendung |
| JOP20190045A1 (ar) | 2016-09-14 | 2019-03-14 | Bayer Ag | مركبات أميد حمض 1- أريل-نفثيريدين-3-كربوكسيليك مستبدلة في الموضع 7 واستخدامها. |
| EP3296298A1 (de) | 2016-09-14 | 2018-03-21 | Bayer Pharma Aktiengesellschaft | 7-substituierte 1-aryl-naphthyridin-3-carbonsäureamide und ihre verwendung |
| WO2019168688A2 (en) | 2018-02-15 | 2019-09-06 | Senhwa Biosciences, Inc. | Quinolone analogs and their salts, compositions, and method for their use |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO156828C (no) * | 1980-11-10 | 1987-12-02 | Otsuka Pharma Co Ltd | Analogifremgangsm te for fremstilling av antibakterielt virksomme benzoheterocykliske forbindelser. |
| JPS62215572A (ja) * | 1986-03-17 | 1987-09-22 | Kyorin Pharmaceut Co Ltd | キノロンカルボン酸誘導体 |
| JP2000505451A (ja) * | 1996-02-21 | 2000-05-09 | ダーウィン・ディスカバリー・リミテッド | キノロン類およびこれらの治療的使用 |
| EP1117406A1 (en) * | 1998-09-30 | 2001-07-25 | Alcon Laboratories, Inc. | Antibiotic compositions for treatment of the eye, ear and nose |
| DE60040979D1 (de) * | 1999-05-07 | 2009-01-15 | Wockhardt Ltd | (s)-benzochinolizincarbonsäuren und ihre verwendung als antibakterielle mittel |
| AU7866701A (en) * | 2000-05-08 | 2001-11-20 | Shiv Kumar Agarwal | Antibacterial chiral 8-(substituted piperidino)-benzo (i, j) quinolizines, processes, compositions and methods of treatment |
| AU2001280091A1 (en) * | 2000-08-01 | 2002-02-13 | Wockhardt Limited | Inhibitors of cellular efflux pumps of microbes |
-
2002
- 2002-12-12 WO PCT/IN2002/000232 patent/WO2003050107A1/en active Application Filing
- 2002-12-12 JP JP2003551131A patent/JP2005511743A/ja not_active Abandoned
- 2002-12-12 AU AU2002361493A patent/AU2002361493A1/en not_active Abandoned
- 2002-12-12 EP EP02796957A patent/EP1453824A1/en not_active Withdrawn
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