NO322011B1 - Aminometylpyrrolidin-derivater som har aromatiske substituenter - Google Patents
Aminometylpyrrolidin-derivater som har aromatiske substituenter Download PDFInfo
- Publication number
- NO322011B1 NO322011B1 NO20014374A NO20014374A NO322011B1 NO 322011 B1 NO322011 B1 NO 322011B1 NO 20014374 A NO20014374 A NO 20014374A NO 20014374 A NO20014374 A NO 20014374A NO 322011 B1 NO322011 B1 NO 322011B1
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- compound
- fluoro
- salts
- hydrates
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- VMPYTOIPVPQDNX-UHFFFAOYSA-N pyrrolidin-1-ylmethanamine Chemical class NCN1CCCC1 VMPYTOIPVPQDNX-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 181
- 150000003839 salts Chemical class 0.000 claims abstract description 67
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 34
- 125000005843 halogen group Chemical group 0.000 claims abstract description 28
- 125000003277 amino group Chemical group 0.000 claims abstract description 18
- 239000003814 drug Substances 0.000 claims abstract description 18
- 229940079593 drug Drugs 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 4
- -1 3-carboxy-6-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-4-oxo-1, 8-naphthyridin-7-yl group Chemical group 0.000 claims description 61
- 150000004677 hydrates Chemical class 0.000 claims description 51
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 239000003242 anti bacterial agent Substances 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 21
- 241000894006 Bacteria Species 0.000 abstract description 8
- 125000003118 aryl group Chemical group 0.000 abstract description 7
- 230000003389 potentiating effect Effects 0.000 abstract description 6
- 150000002148 esters Chemical class 0.000 abstract description 5
- 150000007660 quinolones Chemical class 0.000 abstract description 4
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 description 235
- 239000000243 solution Substances 0.000 description 195
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 191
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 181
- 239000002904 solvent Substances 0.000 description 139
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 130
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 124
- 238000006243 chemical reaction Methods 0.000 description 110
- 238000001816 cooling Methods 0.000 description 94
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 83
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 77
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 75
- 239000000203 mixture Substances 0.000 description 68
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
- 239000012044 organic layer Substances 0.000 description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 39
- 238000010898 silica gel chromatography Methods 0.000 description 38
- 238000005481 NMR spectroscopy Methods 0.000 description 34
- 239000007788 liquid Substances 0.000 description 34
- 239000000725 suspension Substances 0.000 description 33
- 239000013078 crystal Substances 0.000 description 31
- 238000010828 elution Methods 0.000 description 30
- 101150041968 CDC13 gene Proteins 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 26
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 26
- 238000010992 reflux Methods 0.000 description 26
- 238000005160 1H NMR spectroscopy Methods 0.000 description 25
- 230000002269 spontaneous effect Effects 0.000 description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 20
- 238000001953 recrystallisation Methods 0.000 description 20
- IBRJQBANIHRLOX-BUIHEHBWSA-N 5-amino-7-[(3r)-3-[amino(1,3-thiazol-2-yl)methyl]pyrrolidin-1-yl]-6,8-difluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid Chemical compound C([C@H](C1)C(N)C=2SC=CN=2)CN1C(C=1F)=C(F)C(N)=C(C(C(C(O)=O)=C2)=O)C=1N2[C@@H]1C[C@@H]1F IBRJQBANIHRLOX-BUIHEHBWSA-N 0.000 description 19
- 238000000921 elemental analysis Methods 0.000 description 19
- 239000012230 colorless oil Substances 0.000 description 18
- 125000006239 protecting group Chemical group 0.000 description 18
- 229920006395 saturated elastomer Polymers 0.000 description 18
- 239000012299 nitrogen atmosphere Substances 0.000 description 17
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 14
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 12
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019270 ammonium chloride Nutrition 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- JSCZIAPHPBQUJU-CRCLSJGQSA-N 5-amino-6,7,8-trifluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)C=2C(N)=C(F)C(F)=C(F)C=2N1[C@@H]1C[C@@H]1F JSCZIAPHPBQUJU-CRCLSJGQSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 241000192125 Firmicutes Species 0.000 description 8
- HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 229940072132 quinolone antibacterials Drugs 0.000 description 8
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000012046 mixed solvent Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical class C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 125000003808 silyl group Chemical class [H][Si]([H])([H])[*] 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- QSIKXMCGUZFIKE-DGCLKSJQSA-N (3r)-n-methoxy-n-methyl-5-oxo-1-[(1r)-1-phenylethyl]pyrrolidine-3-carboxamide Chemical compound O=C1C[C@@H](C(=O)N(C)OC)CN1[C@H](C)C1=CC=CC=C1 QSIKXMCGUZFIKE-DGCLKSJQSA-N 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 4
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- 230000000694 effects Effects 0.000 description 4
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 4
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- OTMCXXZKALNTAY-HNVBAWDGSA-N (4r)-4-[azido(1,3-thiazol-2-yl)methyl]-1-[(1r)-1-phenylethyl]pyrrolidin-2-one Chemical compound [N-]=[N+]=NC([C@H]1CN(C(C1)=O)[C@H](C)C=1C=CC=CC=1)C1=NC=CS1 OTMCXXZKALNTAY-HNVBAWDGSA-N 0.000 description 3
- RBDBRNQOFYSVNR-HZBOCPGUSA-N (4r)-4-[azido(pyridin-3-yl)methyl]-1-[(1r)-1-phenylethyl]pyrrolidin-2-one Chemical compound [N-]=[N+]=NC([C@H]1CN(C(C1)=O)[C@H](C)C=1C=CC=CC=1)C1=CC=CN=C1 RBDBRNQOFYSVNR-HZBOCPGUSA-N 0.000 description 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
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- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
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- 101100185029 Homo sapiens MSMB gene Proteins 0.000 description 3
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- 206010041925 Staphylococcal infections Diseases 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 3
- 150000005130 benzoxazines Chemical group 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- MRSGPYRZKDVHMJ-DUSLRRAJSA-N benzyl (3r)-3-[furan-2-yl-[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidine-1-carboxylate Chemical compound C([C@H](C1)C(NC(=O)OC(C)(C)C)C=2OC=CC=2)CN1C(=O)OCC1=CC=CC=C1 MRSGPYRZKDVHMJ-DUSLRRAJSA-N 0.000 description 3
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
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- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 3
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- QSIKXMCGUZFIKE-JTDNENJMSA-N n-methoxy-n-methyl-5-oxo-1-[(1r)-1-phenylethyl]pyrrolidine-3-carboxamide Chemical compound O=C1CC(C(=O)N(C)OC)CN1[C@H](C)C1=CC=CC=C1 QSIKXMCGUZFIKE-JTDNENJMSA-N 0.000 description 3
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- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
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- ZBKADWKMVSDECW-DGCLKSJQSA-N (4r)-1-[(1r)-1-phenylethyl]-4-(1,3-thiazole-2-carbonyl)pyrrolidin-2-one Chemical compound O=C([C@H]1CN(C(C1)=O)[C@H](C)C=1C=CC=CC=1)C1=NC=CS1 ZBKADWKMVSDECW-DGCLKSJQSA-N 0.000 description 2
- DXCDVOOOSFUKJU-CZUORRHYSA-N (4r)-1-[(1r)-1-phenylethyl]-4-(pyridine-3-carbonyl)pyrrolidin-2-one Chemical compound O=C([C@H]1CN(C(C1)=O)[C@H](C)C=1C=CC=CC=1)C1=CC=CN=C1 DXCDVOOOSFUKJU-CZUORRHYSA-N 0.000 description 2
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- 239000003782 beta lactam antibiotic agent Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 208000010217 blepharitis Diseases 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 201000009267 bronchiectasis Diseases 0.000 description 1
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229940038705 chlamydia trachomatis Drugs 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 208000003167 cholangitis Diseases 0.000 description 1
- 201000001352 cholecystitis Diseases 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 201000009151 chronic rhinitis Diseases 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 201000007717 corneal ulcer Diseases 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 206010014665 endocarditis Diseases 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 201000010063 epididymitis Diseases 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 208000020426 gonococcal urethritis Diseases 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940047650 haemophilus influenzae Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 208000002557 hidradenitis Diseases 0.000 description 1
- 208000008025 hordeolum Diseases 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 206010025226 lymphangitis Diseases 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- FCPRDUXJWIUVPZ-UHFFFAOYSA-M magnesium;methoxybenzene;bromide Chemical compound [Mg+2].[Br-].COC1=CC=CC=[C-]1 FCPRDUXJWIUVPZ-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 229960001180 norfloxacin Drugs 0.000 description 1
- OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 201000005115 pasteurellosis Diseases 0.000 description 1
- 201000001245 periodontitis Diseases 0.000 description 1
- 206010034674 peritonitis Diseases 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 208000007578 phototoxic dermatitis Diseases 0.000 description 1
- 231100000018 phototoxicity Toxicity 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 208000008423 pleurisy Diseases 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 201000007094 prostatitis Diseases 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical group C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 201000005113 shigellosis Diseases 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
- DRJWAGLRTNDTHS-CMCURQENSA-N tert-butyl n-[[(3r)-5-oxo-1-[(1r)-1-phenylethyl]pyrrolidin-3-yl]-(1,3-thiazol-2-yl)methyl]carbamate Chemical compound CC(C)(C)OC(=O)NC([C@H]1CN(C(C1)=O)[C@H](C)C=1C=CC=CC=1)C1=NC=CS1 DRJWAGLRTNDTHS-CMCURQENSA-N 0.000 description 1
- JTBDNLLDILHUTL-RWANSRKNSA-N tert-butyl n-[furan-2-yl-[(3r)-pyrrolidin-3-yl]methyl]carbamate Chemical compound C=1C=COC=1C(NC(=O)OC(C)(C)C)[C@@H]1CCNC1 JTBDNLLDILHUTL-RWANSRKNSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 206010044008 tonsillitis Diseases 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 208000000143 urethritis Diseases 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002132 β-lactam antibiotic Substances 0.000 description 1
- 229940124586 β-lactam antibiotics Drugs 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
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)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6280699 | 1999-03-10 | ||
| PCT/JP2000/001439 WO2000053594A1 (fr) | 1999-03-10 | 2000-03-09 | Derives aminomethylpyrrolidine possedant des substituants aromatiques |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20014374D0 NO20014374D0 (no) | 2001-09-07 |
| NO20014374L NO20014374L (no) | 2001-11-12 |
| NO322011B1 true NO322011B1 (no) | 2006-08-07 |
Family
ID=13210961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20014374A NO322011B1 (no) | 1999-03-10 | 2001-09-07 | Aminometylpyrrolidin-derivater som har aromatiske substituenter |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US6762181B1 (ru) |
| EP (1) | EP1182202B1 (ru) |
| KR (1) | KR20010102560A (ru) |
| CN (1) | CN1258531C (ru) |
| AT (1) | ATE268329T1 (ru) |
| AU (1) | AU2940300A (ru) |
| DE (1) | DE60011264T2 (ru) |
| NO (1) | NO322011B1 (ru) |
| RU (1) | RU2255938C2 (ru) |
| WO (1) | WO2000053594A1 (ru) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE268329T1 (de) * | 1999-03-10 | 2004-06-15 | Daiichi Seiyaku Co | Aminomethylpyrrolidin-derivate mit aromatischen substituenten |
| US7384773B1 (en) | 2001-05-10 | 2008-06-10 | Pfizer Inc | Crystal of HIV protease-cleaved human beta secretase and method for crystallization thereof |
| US7012144B2 (en) * | 2001-12-31 | 2006-03-14 | Korea Research Institute Of Chemical Technology | Quinolone carboxylic acid derivatives |
| JP4675234B2 (ja) * | 2003-06-06 | 2011-04-20 | 第一三共株式会社 | 光学活性なキノロンカルボン酸誘導体の製造中間体およびその製造法 |
| WO2005111030A1 (en) * | 2004-05-12 | 2005-11-24 | Warner-Lambert Company Llc | Quinolone antibacterial agents |
| CN100441580C (zh) * | 2006-07-14 | 2008-12-10 | 中山大学 | 喹啉二酮衍生物及其在制备抗菌药物中的应用 |
| FR2928150A1 (fr) | 2008-02-29 | 2009-09-04 | Vetoquinol Sa Sa | Nouveaux derives 7-substitues de 3-carboxy-oxadiazino-quinolones, leur preparation et leur application comme anti-bacteriens |
| EP2145891A1 (en) | 2008-07-09 | 2010-01-20 | Vetoquinol S.A. | 9-substituted-5-carboxy-oxadiazino-quinolone derivatives, their preparation and their application as anti-bacterials |
| TW201033184A (en) | 2008-12-05 | 2010-09-16 | Mochida Pharm Co Ltd | Morpholinone compounds as factor IXa inhibitors |
| US8987242B2 (en) | 2008-12-05 | 2015-03-24 | Merck Sharp & Dohme Corp. | Morpholinone compounds as factor IXA inhibitors |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0207420B1 (en) | 1985-06-26 | 1992-05-06 | Daiichi Pharmaceutical Co., Ltd. | Pyridonecarboxylic acid derivatives |
| JPH0723369B2 (ja) * | 1986-12-27 | 1995-03-15 | 第一製薬株式会社 | ピリドンカルボン酸誘導体 |
| US4920120A (en) * | 1988-01-25 | 1990-04-24 | Warner-Lambert Company | Antibacterial agents |
| IL90062A (en) | 1988-04-27 | 1994-10-07 | Daiichi Seiyaku Co | History of pyridonecarboxylic acid, their preparation and pharmaceutical preparations containing them |
| US5157128A (en) * | 1990-11-30 | 1992-10-20 | Warner-Lambert Company | Certain optically active substituted α,α-dialkyl-pyrrolidine-3-methamines useful as intermediates |
| JP3833738B2 (ja) * | 1995-11-15 | 2006-10-18 | 第一製薬株式会社 | 置換アミノメチルピロリジン誘導体 |
| JP4323574B2 (ja) * | 1995-12-13 | 2009-09-02 | 大日本住友製薬株式会社 | 抗腫瘍剤 |
| DE69717988T2 (de) | 1996-05-10 | 2003-07-24 | Pharmacia & Upjohn Co., Kalamazoo | Topische verabreichung von premafloxacin zur behandlung von systemischen bakteriellen erkrankungen |
| JPH10324686A (ja) | 1997-03-27 | 1998-12-08 | Hokuriku Seiyaku Co Ltd | ７−（ヒドロキシピロリジニル）キノリンカルボン酸誘導体 |
| JPH10287669A (ja) | 1997-04-10 | 1998-10-27 | Dai Ichi Seiyaku Co Ltd | 置換アミノメチルピロリジン誘導体 |
| ATE268329T1 (de) * | 1999-03-10 | 2004-06-15 | Daiichi Seiyaku Co | Aminomethylpyrrolidin-derivate mit aromatischen substituenten |
-
2000
- 2000-03-09 AT AT00907973T patent/ATE268329T1/de not_active IP Right Cessation
- 2000-03-09 RU RU2001124813/04A patent/RU2255938C2/ru not_active IP Right Cessation
- 2000-03-09 DE DE60011264T patent/DE60011264T2/de not_active Expired - Fee Related
- 2000-03-09 WO PCT/JP2000/001439 patent/WO2000053594A1/ja active IP Right Grant
- 2000-03-09 KR KR1020017011497A patent/KR20010102560A/ko active IP Right Grant
- 2000-03-09 US US09/936,050 patent/US6762181B1/en not_active Expired - Fee Related
- 2000-03-09 CN CNB008073570A patent/CN1258531C/zh not_active Expired - Fee Related
- 2000-03-09 EP EP00907973A patent/EP1182202B1/en not_active Expired - Lifetime
- 2000-03-09 AU AU29403/00A patent/AU2940300A/en not_active Abandoned
-
2001
- 2001-09-07 NO NO20014374A patent/NO322011B1/no unknown
-
2004
- 2004-04-29 US US10/834,079 patent/US7186843B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20040209940A1 (en) | 2004-10-21 |
| RU2255938C2 (ru) | 2005-07-10 |
| CN1258531C (zh) | 2006-06-07 |
| KR20010102560A (ko) | 2001-11-15 |
| EP1182202A4 (en) | 2002-03-27 |
| DE60011264D1 (de) | 2004-07-08 |
| AU2940300A (en) | 2000-09-28 |
| CN1350527A (zh) | 2002-05-22 |
| DE60011264T2 (de) | 2005-07-14 |
| EP1182202B1 (en) | 2004-06-02 |
| NO20014374D0 (no) | 2001-09-07 |
| NO20014374L (no) | 2001-11-12 |
| EP1182202A1 (en) | 2002-02-27 |
| US6762181B1 (en) | 2004-07-13 |
| US7186843B2 (en) | 2007-03-06 |
| ATE268329T1 (de) | 2004-06-15 |
| WO2000053594A1 (fr) | 2000-09-14 |
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