NO333481B1 - 7-(4-substituert-3-cyklopropylaminometyl-1-pyrrolidinyl)kinolonkarboksylsyrederivater, samt antibakterielt middel inneholdende samme - Google Patents
7-(4-substituert-3-cyklopropylaminometyl-1-pyrrolidinyl)kinolonkarboksylsyrederivater, samt antibakterielt middel inneholdende samme Download PDFInfo
- Publication number
- NO333481B1 NO333481B1 NO20061050A NO20061050A NO333481B1 NO 333481 B1 NO333481 B1 NO 333481B1 NO 20061050 A NO20061050 A NO 20061050A NO 20061050 A NO20061050 A NO 20061050A NO 333481 B1 NO333481 B1 NO 333481B1
- Authority
- NO
- Norway
- Prior art keywords
- fluoro
- group
- cyclopropylaminomethyl
- dihydro
- oxo
- Prior art date
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- -1 7- (4-substituted-3-cyclopropylaminomethyl-1-pyrrolidinyl) quinolone carboxylic acid Chemical class 0.000 title claims abstract description 22
- 239000003242 anti bacterial agent Substances 0.000 title claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 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 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 8
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 8
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- UWXREBKAHFTQNW-KPZWWZAWSA-N 1-cyclopropyl-7-[(3s,4s)-3-[(cyclopropylamino)methyl]-4-fluoropyrrolidin-1-yl]-6-fluoro-8-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound C([C@@H]1[C@H](F)CN(C1)C1=C(C2=C(C(C(C(O)=O)=CN2C2CC2)=O)C=C1F)C)NC1CC1 UWXREBKAHFTQNW-KPZWWZAWSA-N 0.000 claims description 4
- ZFIOCUITTUUVPV-MEDUHNTESA-N 7-[(3s,4s)-3-[(cyclopropylamino)methyl]-4-fluoropyrrolidin-1-yl]-6-fluoro-1-(2-fluoroethyl)-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound C([C@@H]1[C@H](F)CN(C1)C1=C(C2=C(C(C(C(O)=O)=CN2CCF)=O)C=C1F)OC)NC1CC1 ZFIOCUITTUUVPV-MEDUHNTESA-N 0.000 claims description 4
- SHJNBBLBEWBCED-JWSRLSBWSA-N 7-[(3s,4s)-3-[(cyclopropylamino)methyl]-4-fluoropyrrolidin-1-yl]-6-fluoro-1-[(1r,2s)-2-fluorocyclopropyl]-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound C([C@@H]1[C@H](F)CN(C1)C1=C(C2=C(C(C(C(O)=O)=CN2[C@H]2[C@H](C2)F)=O)C=C1F)OC)NC1CC1 SHJNBBLBEWBCED-JWSRLSBWSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- URGGPCGRXSPNKQ-MGPLVRAMSA-N 8-chloro-1-cyclopropyl-7-[(3s,4s)-3-[(cyclopropylamino)methyl]-4-fluoropyrrolidin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(Cl)C(N3C[C@H](CNC4CC4)[C@H](F)C3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 URGGPCGRXSPNKQ-MGPLVRAMSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- HKJXBKLPEVUUMT-IINYFYTJSA-N 5-amino-1-cyclopropyl-7-[(3s,4s)-3-[(cyclopropylamino)methyl]-4-fluoropyrrolidin-1-yl]-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound C([C@@H]1[C@H](F)CN(C1)C1=C(C2=C(C(C(C(O)=O)=CN2C2CC2)=O)C(N)=C1F)OC)NC1CC1 HKJXBKLPEVUUMT-IINYFYTJSA-N 0.000 claims description 2
- HTWDALGYZDLPNI-OLRMPSLUSA-N 5-amino-7-[(3s,4s)-3-[(cyclopropylamino)methyl]-4-fluoropyrrolidin-1-yl]-6-fluoro-1-[(1r,2s)-2-fluorocyclopropyl]-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound C([C@@H]1[C@H](F)CN(C1)C1=C(C2=C(C(C(C(O)=O)=CN2[C@H]2[C@H](C2)F)=O)C(N)=C1F)OC)NC1CC1 HTWDALGYZDLPNI-OLRMPSLUSA-N 0.000 claims description 2
- KYNRMIVOIFUPKP-MVEWNYDKSA-N 7-[(3s,4s)-3-[(cyclopropylamino)methyl]-4-fluoropyrrolidin-1-yl]-6,8-difluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3C[C@H](CNC4CC4)[C@H](F)C3)=C(F)C=C2C(=O)C(C(=O)O)=CN1[C@@H]1C[C@@H]1F KYNRMIVOIFUPKP-MVEWNYDKSA-N 0.000 claims description 2
- FCPGYXMBVQSZAH-MVEWNYDKSA-N 8-chloro-7-[(3s,4s)-3-[(cyclopropylamino)methyl]-4-fluoropyrrolidin-1-yl]-6-fluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(Cl)C(N3C[C@H](CNC4CC4)[C@H](F)C3)=C(F)C=C2C(=O)C(C(=O)O)=CN1[C@@H]1C[C@@H]1F FCPGYXMBVQSZAH-MVEWNYDKSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- OWOHDMCHJWDCEO-BSLXNSKLSA-N 5-amino-7-[(3s,4s)-3-[(cyclopropylamino)methyl]-4-fluoropyrrolidin-1-yl]-6-fluoro-1-[(1r,2s)-2-fluorocyclopropyl]-8-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound C([C@@H]1[C@H](F)CN(C1)C1=C(C2=C(C(C(C(O)=O)=CN2[C@H]2[C@H](C2)F)=O)C(N)=C1F)C)NC1CC1 OWOHDMCHJWDCEO-BSLXNSKLSA-N 0.000 claims 1
- 241000894006 Bacteria Species 0.000 abstract description 12
- 239000003814 drug Substances 0.000 abstract description 11
- 229940079593 drug Drugs 0.000 abstract description 11
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 7
- 241000192125 Firmicutes Species 0.000 abstract description 4
- OYAXZPAIVGVTTM-APPDUMDISA-N 1-cyclopropyl-7-[(3s,4s)-3-[(cyclopropylamino)methyl]-4-fluoropyrrolidin-1-yl]-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound C([C@@H]1[C@H](F)CN(C1)C1=C(C2=C(C(C(C(O)=O)=CN2C2CC2)=O)C=C1F)OC)NC1CC1 OYAXZPAIVGVTTM-APPDUMDISA-N 0.000 abstract description 3
- 230000003389 potentiating effect Effects 0.000 abstract description 2
- 102100025142 Beta-microseminoprotein Human genes 0.000 abstract 1
- 101100185029 Homo sapiens MSMB gene Proteins 0.000 abstract 1
- 206010041925 Staphylococcal infections Diseases 0.000 abstract 1
- 208000015688 methicillin-resistant staphylococcus aureus infectious disease Diseases 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 257
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 171
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 138
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 129
- 239000000203 mixture Substances 0.000 description 125
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 108
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 105
- 239000000243 solution Substances 0.000 description 85
- 238000000034 method Methods 0.000 description 79
- 238000010898 silica gel chromatography Methods 0.000 description 61
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
- 239000011541 reaction mixture Substances 0.000 description 57
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 55
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- 239000003480 eluent Substances 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
- 230000015572 biosynthetic process Effects 0.000 description 48
- 238000003786 synthesis reaction Methods 0.000 description 48
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- 239000010410 layer Substances 0.000 description 42
- 239000013078 crystal Substances 0.000 description 39
- QZFXTAVCZYQMQZ-HTRCEHHLSA-N n-[[(3r,4s)-4-fluoropyrrolidin-3-yl]methyl]cyclopropanamine Chemical compound F[C@@H]1CNC[C@@H]1CNC1CC1 QZFXTAVCZYQMQZ-HTRCEHHLSA-N 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 238000000921 elemental analysis Methods 0.000 description 32
- 239000005457 ice water Substances 0.000 description 32
- 238000003756 stirring Methods 0.000 description 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 30
- 239000007864 aqueous solution Substances 0.000 description 30
- 238000005406 washing Methods 0.000 description 29
- 239000000706 filtrate Substances 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 25
- 235000002639 sodium chloride Nutrition 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 239000000460 chlorine Substances 0.000 description 23
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
- 239000003054 catalyst Substances 0.000 description 22
- 239000003921 oil Substances 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 239000006188 syrup Substances 0.000 description 15
- 235000020357 syrup Nutrition 0.000 description 15
- 239000002198 insoluble material Substances 0.000 description 14
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 12
- 229910052796 boron Inorganic materials 0.000 description 12
- 239000012230 colorless oil Substances 0.000 description 12
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 12
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- 235000017557 sodium bicarbonate Nutrition 0.000 description 11
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 10
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- WOMQTKDTCNPUAH-NEPJUHHUSA-N benzyl (3r,4r)-3-hydroxy-4-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound C1[C@H](O)[C@@H](CO)CN1C(=O)OCC1=CC=CC=C1 WOMQTKDTCNPUAH-NEPJUHHUSA-N 0.000 description 8
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 8
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 7
- 235000011054 acetic acid Nutrition 0.000 description 7
- 150000004677 hydrates Chemical class 0.000 description 7
- 239000002808 molecular sieve Substances 0.000 description 7
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 7
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 6
- 229910000085 borane Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 6
- 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 6
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
- 239000005909 Kieselgur Substances 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- PMCKNQJLBLXDNO-RYUDHWBXSA-N diazonio-[[(3r,4r)-4-hydroxy-1-phenylmethoxycarbonylpyrrolidin-3-yl]methyl]azanide Chemical compound C1[C@H](CN=[N+]=[N-])[C@@H](O)CN1C(=O)OCC1=CC=CC=C1 PMCKNQJLBLXDNO-RYUDHWBXSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
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- UUPRZHFECHMJNI-WFASDCNBSA-N (3r,4r)-1-benzyl-n-cyclopropyl-4-methylpyrrolidine-3-carboxamide Chemical compound C([C@@H]([C@H](C1)C(=O)NC2CC2)C)N1CC1=CC=CC=C1 UUPRZHFECHMJNI-WFASDCNBSA-N 0.000 description 4
- AAIPXTOLUFTTBB-NOLJZWGESA-N (3r,4s)-n-cyclopropyl-4-(hydroxymethyl)-1-[(1s)-1-phenylethyl]pyrrolidine-3-carboxamide Chemical compound O=C([C@@H]1[C@H](CO)CN(C1)[C@@H](C)C=1C=CC=CC=1)NC1CC1 AAIPXTOLUFTTBB-NOLJZWGESA-N 0.000 description 4
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- GLFBPDDMMVIVQJ-WCQYABFASA-N [(3r,4r)-1-benzyl-4-methylpyrrolidin-3-yl]methanamine Chemical compound C1[C@@H](CN)[C@@H](C)CN1CC1=CC=CC=C1 GLFBPDDMMVIVQJ-WCQYABFASA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
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- BZMMRNKDONDVIB-UHFFFAOYSA-N (1-ethoxycyclopropyl)oxy-trimethylsilane Chemical compound CCOC1(O[Si](C)(C)C)CC1 BZMMRNKDONDVIB-UHFFFAOYSA-N 0.000 description 3
- BSQXZHMREYHKOM-UHNVWZDZSA-N (3r,4r)-4-(hydroxymethyl)pyrrolidin-3-ol Chemical compound OC[C@H]1CNC[C@@H]1O BSQXZHMREYHKOM-UHNVWZDZSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
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- 208000035473 Communicable disease Diseases 0.000 description 3
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QRDWIYAPESWLCD-KGLIPLIRSA-N [(3r,4r)-1-benzyl-4-methylsulfonyloxypyrrolidin-3-yl]methyl methanesulfonate Chemical compound C1[C@H](OS(C)(=O)=O)[C@@H](COS(=O)(=O)C)CN1CC1=CC=CC=C1 QRDWIYAPESWLCD-KGLIPLIRSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000002829 antibacterial sensitivity test Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- ILUUGGSFJQTCJS-SJORKVTESA-N benzyl (3r,4r)-3-[tert-butyl(dimethyl)silyl]oxy-4-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound C1[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)CN1C(=O)OCC1=CC=CC=C1 ILUUGGSFJQTCJS-SJORKVTESA-N 0.000 description 1
- BPCBXAMBPRGIHU-KGLIPLIRSA-N benzyl (3r,4r)-3-methylsulfonyloxy-4-(methylsulfonyloxymethyl)pyrrolidine-1-carboxylate Chemical compound C1[C@H](OS(C)(=O)=O)[C@@H](COS(=O)(=O)C)CN1C(=O)OCC1=CC=CC=C1 BPCBXAMBPRGIHU-KGLIPLIRSA-N 0.000 description 1
- JVJIAXHMDGHNPE-NWDGAFQWSA-N benzyl (3s,4s)-3-(aminomethyl)-4-fluoropyrrolidine-1-carboxylate Chemical compound C1[C@@H](F)[C@@H](CN)CN1C(=O)OCC1=CC=CC=C1 JVJIAXHMDGHNPE-NWDGAFQWSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- KZEUBCHQWLGYRM-UHFFFAOYSA-N ethyl 1-tert-butyl-6,7,8-trifluoro-4-oxoquinoline-3-carboxylate Chemical compound FC1=C(F)C=C2C(=O)C(C(=O)OCC)=CN(C(C)(C)C)C2=C1F KZEUBCHQWLGYRM-UHFFFAOYSA-N 0.000 description 1
- XIAGPZODABVXHC-UHFFFAOYSA-N ethyl 1-tert-butyl-6,7-difluoro-4-oxoquinoline-3-carboxylate Chemical compound FC1=C(F)C=C2C(=O)C(C(=O)OCC)=CN(C(C)(C)C)C2=C1 XIAGPZODABVXHC-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229960003085 meticillin Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- RULHSLKSRFNQJO-UHFFFAOYSA-N n-(methoxymethyl)-1-phenyl-n-trimethylsilylmethanamine Chemical compound COCN([Si](C)(C)C)CC1=CC=CC=C1 RULHSLKSRFNQJO-UHFFFAOYSA-N 0.000 description 1
- ACBQVTXYPJOGLH-UHFFFAOYSA-N n-[6,6-dimethyl-2,4-dioxo-1-(oxolan-2-ylmethyl)-3-(trifluoromethyl)-5,7-dihydroindol-3-yl]pyridine-3-carboxamide Chemical compound O=C1CC(C)(C)CC(N(C2=O)CC3OCCC3)=C1C2(C(F)(F)F)NC(=O)C1=CC=CN=C1 ACBQVTXYPJOGLH-UHFFFAOYSA-N 0.000 description 1
- WMXHCDXOKJTPPA-HTQZYQBOSA-N n-[[(3r,4s)-4-methylpyrrolidin-3-yl]methyl]cyclopropanamine Chemical compound C[C@@H]1CNC[C@@H]1CNC1CC1 WMXHCDXOKJTPPA-HTQZYQBOSA-N 0.000 description 1
- ASIUOPIHNSIMCP-JBACZVJFSA-N n-[[(3s,4s)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-[(1s)-1-phenylethyl]pyrrolidin-3-yl]methyl]cyclopropanamine Chemical compound C([C@H]1CN(C[C@H]1CO[Si](C)(C)C(C)(C)C)[C@@H](C)C=1C=CC=CC=1)NC1CC1 ASIUOPIHNSIMCP-JBACZVJFSA-N 0.000 description 1
- YAEIDJCDTOJWLQ-WLYNEOFISA-N n-[[(3s,4s)-4-methylpyrrolidin-3-yl]methyl]cyclopropanamine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C[C@@H]1CNC[C@H]1CNC1CC1 YAEIDJCDTOJWLQ-WLYNEOFISA-N 0.000 description 1
- AELLFKPPLQHPRV-UHFFFAOYSA-N n-propan-2-yl-7-propan-2-yliminocyclohepta-1,3,5-trien-1-amine Chemical compound CC(C)NC1=CC=CC=CC1=NC(C)C AELLFKPPLQHPRV-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- 229960001180 norfloxacin Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- VMPYTOIPVPQDNX-UHFFFAOYSA-N pyrrolidin-1-ylmethanamine Chemical compound NCN1CCCC1 VMPYTOIPVPQDNX-UHFFFAOYSA-N 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- BSTWKRUNXOFBPE-SFYZADRCSA-N tert-butyl (3r,4r)-3-hydroxy-4-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C[C@H](O)[C@@H](CO)C1 BSTWKRUNXOFBPE-SFYZADRCSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C([O-])=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003318897 | 2003-09-10 | ||
| PCT/JP2004/013049 WO2005026147A1 (ja) | 2003-09-10 | 2004-09-08 | ７−（４−置換−３−シクロプロピルアミノメチル−１−ピロリジニル）キノロンカルボン酸誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20061050L NO20061050L (no) | 2006-04-04 |
| NO333481B1 true NO333481B1 (no) | 2013-06-24 |
Family
ID=34308537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20061050A NO333481B1 (no) | 2003-09-10 | 2006-03-03 | 7-(4-substituert-3-cyklopropylaminometyl-1-pyrrolidinyl)kinolonkarboksylsyrederivater, samt antibakterielt middel inneholdende samme |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US7514451B2 (ja) |
| EP (1) | EP1666477B1 (ja) |
| JP (1) | JP4639149B2 (ja) |
| KR (1) | KR101077755B1 (ja) |
| CN (1) | CN100410249C (ja) |
| AU (1) | AU2004272414B2 (ja) |
| BR (1) | BRPI0413964B8 (ja) |
| CA (1) | CA2536429C (ja) |
| CY (1) | CY1114476T1 (ja) |
| DK (1) | DK1666477T3 (ja) |
| ES (1) | ES2424676T3 (ja) |
| NO (1) | NO333481B1 (ja) |
| NZ (1) | NZ545472A (ja) |
| PL (1) | PL1666477T3 (ja) |
| PT (1) | PT1666477E (ja) |
| SG (1) | SG144936A1 (ja) |
| SI (1) | SI1666477T1 (ja) |
| WO (1) | WO2005026147A1 (ja) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI1666477T1 (sl) * | 2003-09-10 | 2013-10-30 | Kyorin Pharmaceutical Co., Ltd. | Derivati 7-(4-substituiran 3-ciklopropilaminometil-1-pirolidinil) kinolonkarboksilne kisline |
| US7667049B2 (en) * | 2006-03-09 | 2010-02-23 | Kyorin Pharmaceutical Co., Ltd. | Process for producing 3,4-disubstituted pyrrolidine derivative and production intermediate thereof |
| WO2011152354A1 (ja) * | 2010-05-31 | 2011-12-08 | 杏林製薬株式会社 | ３－置換－４－フルオロピロリジン誘導体の製造方法 |
| EP2634172A4 (en) | 2010-10-25 | 2014-01-29 | Kyorin Seiyaku Kk | METHOD FOR MANUFACTURING DISUBSTITUTED DERIVED DERIVATIVE 3, 4 |
| SA112330992B1 (ar) | 2011-11-10 | 2015-09-13 | كيورين فارماسوتيكال كو.، ليمتد | صورة متبلرة من 7-{(s4، s3)-3-[(سيكلو بروبيل أمينو) ميثيل]-4-فلورو بيروليدين-1-يل}-6-فلورو-1-(2-فلورو إيثيل)- 8-ميثوكسي-4-أوكسو-1، 4-داي هيدرو كينولين-3- حمض كربوكسيلي |
| WO2013145749A1 (ja) * | 2012-03-29 | 2013-10-03 | 杏林製薬株式会社 | カプセル製剤 |
| JP6062422B2 (ja) * | 2012-03-29 | 2017-01-18 | 杏林製薬株式会社 | カプセル製剤 |
| JP5700740B1 (ja) * | 2013-04-25 | 2015-04-15 | 杏林製薬株式会社 | 固形医薬組成物 |
| JP5651812B1 (ja) * | 2013-04-25 | 2015-01-14 | 杏林製薬株式会社 | 固形医薬組成物 |
| JP6349306B2 (ja) * | 2013-04-25 | 2018-06-27 | 杏林製薬株式会社 | 錠剤 |
| US10154993B2 (en) * | 2014-10-23 | 2018-12-18 | Kyorin Pharmaceutical Co., Ltd. | Solid pharmaceutical composition |
| KR102532681B1 (ko) * | 2015-03-13 | 2023-05-15 | 교린 세이야꾸 가부시키 가이샤 | 호흡기 감염증 치료제 |
| JP6031217B1 (ja) * | 2015-06-02 | 2016-11-24 | 杏林製薬株式会社 | 水性液剤 |
| CA2988092A1 (en) * | 2015-06-02 | 2016-12-08 | Kyorin Pharmaceutical Co., Ltd. | Aqueous liquid formulation |
| EP3305295A4 (en) * | 2015-06-02 | 2019-02-20 | Kyorin Pharmaceutical Co., Ltd. | AQUEOUS MEDICINE |
| CA2987879A1 (en) * | 2015-06-02 | 2016-12-08 | Kyorin Pharmaceutical Co., Ltd. | Aqueous drug |
| JP6031216B1 (ja) * | 2015-06-02 | 2016-11-24 | 杏林製薬株式会社 | 水性液剤 |
| CN106831795B (zh) * | 2017-01-16 | 2018-12-21 | 石家庄学院 | 喹诺酮异土木香内酯衍生物及其制备和应用 |
| KR20200016960A (ko) | 2017-06-16 | 2020-02-17 | 교린 세이야꾸 가부시키 가이샤 | 흡인성 폐렴, 폐화농증 또는 폐농양의 치료제 |
| KR20240096794A (ko) | 2017-06-16 | 2024-06-26 | 교린 세이야꾸 가부시키 가이샤 | 흡인성 폐렴, 폐화농증 또는 폐농양의 치료제 |
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-
2004
- 2004-09-08 SI SI200432069T patent/SI1666477T1/sl unknown
- 2004-09-08 PL PL04787732T patent/PL1666477T3/pl unknown
- 2004-09-08 AU AU2004272414A patent/AU2004272414B2/en not_active Ceased
- 2004-09-08 ES ES04787732T patent/ES2424676T3/es not_active Expired - Lifetime
- 2004-09-08 BR BRPI0413964A patent/BRPI0413964B8/pt not_active IP Right Cessation
- 2004-09-08 SG SG200805397-7A patent/SG144936A1/en unknown
- 2004-09-08 WO PCT/JP2004/013049 patent/WO2005026147A1/ja active Application Filing
- 2004-09-08 NZ NZ545472A patent/NZ545472A/xx not_active IP Right Cessation
- 2004-09-08 EP EP04787732.9A patent/EP1666477B1/en not_active Expired - Lifetime
- 2004-09-08 CA CA2536429A patent/CA2536429C/en not_active Expired - Fee Related
- 2004-09-08 CN CNB2004800260554A patent/CN100410249C/zh not_active Expired - Lifetime
- 2004-09-08 US US10/569,062 patent/US7514451B2/en not_active Expired - Lifetime
- 2004-09-08 JP JP2005513875A patent/JP4639149B2/ja not_active Expired - Lifetime
- 2004-09-08 KR KR1020067005026A patent/KR101077755B1/ko active IP Right Grant
- 2004-09-08 PT PT47877329T patent/PT1666477E/pt unknown
- 2004-09-08 DK DK04787732.9T patent/DK1666477T3/da active
-
2006
- 2006-03-03 NO NO20061050A patent/NO333481B1/no not_active IP Right Cessation
-
2009
- 2009-02-26 US US12/379,699 patent/US8106072B2/en not_active Expired - Fee Related
-
2013
- 2013-09-13 CY CY20131100794T patent/CY1114476T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0413964B8 (pt) | 2021-05-25 |
| US20090176824A1 (en) | 2009-07-09 |
| EP1666477A1 (en) | 2006-06-07 |
| CN100410249C (zh) | 2008-08-13 |
| CA2536429C (en) | 2012-02-14 |
| AU2004272414A1 (en) | 2005-03-24 |
| JP4639149B2 (ja) | 2011-02-23 |
| SG144936A1 (en) | 2008-08-28 |
| CY1114476T1 (el) | 2016-10-05 |
| WO2005026147A1 (ja) | 2005-03-24 |
| KR101077755B1 (ko) | 2011-10-27 |
| BRPI0413964A (pt) | 2006-10-31 |
| NO20061050L (no) | 2006-04-04 |
| PL1666477T3 (pl) | 2013-11-29 |
| NZ545472A (en) | 2009-09-25 |
| US7514451B2 (en) | 2009-04-07 |
| EP1666477B1 (en) | 2013-07-03 |
| BRPI0413964B1 (pt) | 2017-03-28 |
| SI1666477T1 (sl) | 2013-10-30 |
| JPWO2005026147A1 (ja) | 2007-11-08 |
| DK1666477T3 (da) | 2013-07-29 |
| CA2536429A1 (en) | 2005-03-24 |
| KR20060123096A (ko) | 2006-12-01 |
| AU2004272414B2 (en) | 2009-05-28 |
| EP1666477A4 (en) | 2008-10-22 |
| PT1666477E (pt) | 2013-08-28 |
| CN1849316A (zh) | 2006-10-18 |
| US8106072B2 (en) | 2012-01-31 |
| US20060281779A1 (en) | 2006-12-14 |
| ES2424676T3 (es) | 2013-10-07 |
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