NO321528B1 - Cykloalkyl-substituerte aminometylpyrrolidin-derivater, og antibakterielle midler inneholdende slike forbindelser - Google Patents
Cykloalkyl-substituerte aminometylpyrrolidin-derivater, og antibakterielle midler inneholdende slike forbindelser Download PDFInfo
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- NO321528B1 NO321528B1 NO20012522A NO20012522A NO321528B1 NO 321528 B1 NO321528 B1 NO 321528B1 NO 20012522 A NO20012522 A NO 20012522A NO 20012522 A NO20012522 A NO 20012522A NO 321528 B1 NO321528 B1 NO 321528B1
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- compound
- group
- formula
- amino
- cyclopropyl
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- 150000001875 compounds Chemical class 0.000 title claims description 135
- 239000003242 anti bacterial agent Chemical class 0.000 title claims description 15
- VMPYTOIPVPQDNX-UHFFFAOYSA-N pyrrolidin-1-ylmethanamine Chemical class NCN1CCCC1 VMPYTOIPVPQDNX-UHFFFAOYSA-N 0.000 title description 4
- -1 2-fluoro -4-hydroxyphenyl group Chemical group 0.000 claims description 51
- 150000003839 salts Chemical class 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 150000004677 hydrates Chemical class 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 11
- 125000003277 amino group Chemical group 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 7
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 6
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 130
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 86
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 64
- 238000006243 chemical reaction Methods 0.000 description 59
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 56
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 238000001816 cooling Methods 0.000 description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- 239000002904 solvent Substances 0.000 description 41
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 239000000203 mixture Substances 0.000 description 35
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 33
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
- 238000001914 filtration Methods 0.000 description 23
- 238000005481 NMR spectroscopy Methods 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 230000000844 anti-bacterial effect Effects 0.000 description 22
- 239000013078 crystal Substances 0.000 description 22
- 239000012044 organic layer Substances 0.000 description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- 229920006395 saturated elastomer Polymers 0.000 description 19
- 239000007864 aqueous solution Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000010898 silica gel chromatography Methods 0.000 description 16
- 239000011780 sodium chloride Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 230000002378 acidificating effect Effects 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 229940072132 quinolone antibacterials Drugs 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 8
- 239000012230 colorless oil Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 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 7
- 241000192125 Firmicutes Species 0.000 description 7
- 239000005909 Kieselgur Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 5
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- 239000012153 distilled water Substances 0.000 description 5
- 150000002148 esters Chemical group 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 150000007660 quinolones Chemical class 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 206010028470 Mycoplasma infections Diseases 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 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 3
- PVTXJGJDOHYFOX-UHFFFAOYSA-N 2h-1,4-benzoxazine Chemical group C1=CC=C2N=CCOC2=C1 PVTXJGJDOHYFOX-UHFFFAOYSA-N 0.000 description 3
- 241000271566 Aves Species 0.000 description 3
- 208000035473 Communicable disease Diseases 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 206010039438 Salmonella Infections Diseases 0.000 description 3
- 206010040047 Sepsis Diseases 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- YJJSUSRMSXJKAN-UHFFFAOYSA-N benzyl 3-[[1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopropyl]methyl]pyrrolidine-1-carboxylate Chemical compound C1CN(C(=O)OCC=2C=CC=CC=2)CC1CC1(NC(=O)OC(C)(C)C)CC1 YJJSUSRMSXJKAN-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 201000003146 cystitis Diseases 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
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- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- TUKJTSUSKQOYCD-STHAYSLISA-N (1r,2s)-2-fluorocyclopropan-1-amine Chemical compound N[C@@H]1C[C@@H]1F TUKJTSUSKQOYCD-STHAYSLISA-N 0.000 description 2
- RHDJWSFQLSPPOK-RLSDIYDTSA-N (4R)-4-(1-azidocyclobutyl)-3-methyl-1-[(1R)-1-phenylethyl]pyrrolidin-2-one Chemical compound N(=[N+]=[N-])C1(CCC1)[C@@H]1C(C(N(C1)[C@H](C)C1=CC=CC=C1)=O)C RHDJWSFQLSPPOK-RLSDIYDTSA-N 0.000 description 2
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- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
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- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 2
- XNIVKSPSCYJKBL-UHFFFAOYSA-N 2h-1,2-benzoxazine-6-carboxylic acid Chemical class O1NC=CC2=CC(C(=O)O)=CC=C21 XNIVKSPSCYJKBL-UHFFFAOYSA-N 0.000 description 2
- KRPCGTMSQPRVEJ-GXSJLCMTSA-N 6-fluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid Chemical class C12=CC=C(F)C=C2C(=O)C(C(=O)O)=CN1[C@@H]1C[C@@H]1F KRPCGTMSQPRVEJ-GXSJLCMTSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
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- 101150041968 CDC13 gene Proteins 0.000 description 2
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- 208000003322 Coinfection Diseases 0.000 description 2
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- 241000282412 Homo Species 0.000 description 2
- 101100185029 Homo sapiens MSMB gene Proteins 0.000 description 2
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- 229910052783 alkali metal Inorganic materials 0.000 description 2
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 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
- 230000001629 suppression Effects 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
- UTCBUDHYAHRXSX-QZTJIDSGSA-N tert-butyl n-[1-[[(3r)-1-[(1r)-1-phenylethyl]pyrrolidin-3-yl]methyl]cyclobutyl]carbamate Chemical compound C([C@H]1CCN(C1)[C@H](C)C=1C=CC=CC=1)C1(NC(=O)OC(C)(C)C)CCC1 UTCBUDHYAHRXSX-QZTJIDSGSA-N 0.000 description 1
- HAIWCOSKBUIMPO-TZHYSIJRSA-N tert-butyl n-[1-[[1-[(1r)-1-phenylethyl]pyrrolidin-3-yl]methyl]cyclopropyl]carbamate Chemical compound C1N([C@H](C)C=2C=CC=CC=2)CCC1CC1(NC(=O)OC(C)(C)C)CC1 HAIWCOSKBUIMPO-TZHYSIJRSA-N 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
- 229920002554 vinyl polymer Polymers 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP33223598 | 1998-11-24 | ||
| PCT/JP1999/006521 WO2000031062A1 (fr) | 1998-11-24 | 1999-11-22 | Derives d'aminomethylpyrrolidine substitues par des cycloalkyles |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20012522D0 NO20012522D0 (no) | 2001-05-22 |
| NO20012522L NO20012522L (no) | 2001-07-24 |
| NO321528B1 true NO321528B1 (no) | 2006-05-15 |
Family
ID=18252698
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20012522A NO321528B1 (no) | 1998-11-24 | 2001-05-22 | Cykloalkyl-substituerte aminometylpyrrolidin-derivater, og antibakterielle midler inneholdende slike forbindelser |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6573260B1 (zh) |
| EP (1) | EP1134219B1 (zh) |
| KR (1) | KR100652470B1 (zh) |
| CN (1) | CN1173971C (zh) |
| AR (1) | AR028806A1 (zh) |
| AT (1) | ATE297912T1 (zh) |
| AU (1) | AU757805B2 (zh) |
| BR (1) | BR9915599A (zh) |
| CA (1) | CA2351497A1 (zh) |
| DE (1) | DE69925859T2 (zh) |
| DK (1) | DK1134219T3 (zh) |
| ES (1) | ES2244248T3 (zh) |
| HK (1) | HK1037635A1 (zh) |
| ID (1) | ID28795A (zh) |
| IL (2) | IL143210A0 (zh) |
| MY (1) | MY125894A (zh) |
| NO (1) | NO321528B1 (zh) |
| PT (1) | PT1134219E (zh) |
| RU (1) | RU2248970C2 (zh) |
| TW (1) | TW542832B (zh) |
| WO (1) | WO2000031062A1 (zh) |
| ZA (1) | ZA200104139B (zh) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0115326A (pt) | 2000-11-20 | 2004-02-25 | Daiichi Seiyaku Co | Compostos dehalogenados |
| US6818787B2 (en) | 2001-06-11 | 2004-11-16 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| US7186855B2 (en) | 2001-06-11 | 2007-03-06 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| US8048917B2 (en) | 2005-04-06 | 2011-11-01 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| WO2005111030A1 (en) * | 2004-05-12 | 2005-11-24 | Warner-Lambert Company Llc | Quinolone antibacterial agents |
| US20090156577A1 (en) * | 2004-09-09 | 2009-06-18 | Benjamin Davis | 7-amino alkylidenyl-heterocyclic quinolones and naphthyridones |
| WO2008021491A2 (en) * | 2006-08-16 | 2008-02-21 | Achillion Pharmaceuticals, Inc. | Method for synthesis of 8-alkoxy-9h-isothiazolo[5,4-b]quinoline-3,4-diones |
| SI2097400T1 (sl) * | 2007-01-05 | 2013-10-30 | Daiichi Sankyo Company, Limited | Zliti substituirani aminopirolidinski derivat |
| US7902227B2 (en) * | 2007-07-27 | 2011-03-08 | Janssen Pharmaceutica Nv. | C-7 isoxazolinyl quinolone / naphthyridine derivatives useful as antibacterial agents |
| RU2636751C1 (ru) * | 2016-11-02 | 2017-12-01 | федеральное государственное автономное образовательное учреждение высшего образования "Казанский (Приволжский) федеральный университет" (ФГАОУ ВО КФУ) | Антибактериальные средства на основе производных ципрофлоксацина |
| CN114180594B (zh) * | 2020-09-14 | 2023-05-02 | 中国石油化工股份有限公司 | 一种ith分子筛的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4920120A (en) * | 1988-01-25 | 1990-04-24 | Warner-Lambert Company | Antibacterial agents |
| MY105136A (en) * | 1988-04-27 | 1994-08-30 | Daiichi Seiyaku Co | Optically active pyridonecarboxylic acid derivatives. |
| US5157128A (en) * | 1990-11-30 | 1992-10-20 | Warner-Lambert Company | Certain optically active substituted α,α-dialkyl-pyrrolidine-3-methamines useful as intermediates |
| IL122296A0 (en) * | 1995-06-06 | 1998-04-05 | Abbott Lab | Quinolizinone type compounds |
| JPH10198204A (ja) * | 1997-01-09 | 1998-07-31 | Fuji Xerox Co Ltd | 画像定着装置 |
| 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 |
| TR200001435T2 (tr) * | 1997-09-15 | 2000-08-21 | The Procter & Gamble Company | Antimikrobiyal kuinolonlar, bunların bileşimleri ve kullanımları |
-
1999
- 1999-11-22 EP EP99972631A patent/EP1134219B1/en not_active Expired - Lifetime
- 1999-11-22 ID IDW00200101127A patent/ID28795A/id unknown
- 1999-11-22 IL IL14321099A patent/IL143210A0/xx active IP Right Grant
- 1999-11-22 WO PCT/JP1999/006521 patent/WO2000031062A1/ja active IP Right Grant
- 1999-11-22 BR BR9915599-0A patent/BR9915599A/pt not_active Application Discontinuation
- 1999-11-22 ES ES99972631T patent/ES2244248T3/es not_active Expired - Lifetime
- 1999-11-22 AT AT99972631T patent/ATE297912T1/de not_active IP Right Cessation
- 1999-11-22 CN CNB998158380A patent/CN1173971C/zh not_active Expired - Fee Related
- 1999-11-22 RU RU2001114213/04A patent/RU2248970C2/ru not_active IP Right Cessation
- 1999-11-22 CA CA002351497A patent/CA2351497A1/en not_active Abandoned
- 1999-11-22 AU AU11862/00A patent/AU757805B2/en not_active Ceased
- 1999-11-22 KR KR1020017006537A patent/KR100652470B1/ko not_active IP Right Cessation
- 1999-11-22 DK DK99972631T patent/DK1134219T3/da active
- 1999-11-22 PT PT99972631T patent/PT1134219E/pt unknown
- 1999-11-22 DE DE69925859T patent/DE69925859T2/de not_active Expired - Fee Related
- 1999-11-22 US US09/856,631 patent/US6573260B1/en not_active Expired - Fee Related
- 1999-11-22 MY MYPI99005083A patent/MY125894A/en unknown
- 1999-11-24 AR ARP990105976A patent/AR028806A1/es active IP Right Grant
- 1999-11-24 TW TW088120516A patent/TW542832B/zh not_active IP Right Cessation
-
2001
- 2001-05-17 IL IL143210A patent/IL143210A/en not_active IP Right Cessation
- 2001-05-21 ZA ZA200104139A patent/ZA200104139B/en unknown
- 2001-05-22 NO NO20012522A patent/NO321528B1/no unknown
- 2001-12-11 HK HK01108680A patent/HK1037635A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1134219A4 (en) | 2002-11-06 |
| RU2248970C2 (ru) | 2005-03-27 |
| BR9915599A (pt) | 2001-11-20 |
| AR028806A1 (es) | 2003-05-28 |
| EP1134219B1 (en) | 2005-06-15 |
| IL143210A0 (en) | 2002-04-21 |
| ES2244248T3 (es) | 2005-12-01 |
| ATE297912T1 (de) | 2005-07-15 |
| HK1037635A1 (en) | 2002-02-15 |
| DE69925859D1 (en) | 2005-07-21 |
| CN1333765A (zh) | 2002-01-30 |
| EP1134219A1 (en) | 2001-09-19 |
| KR20010080564A (ko) | 2001-08-22 |
| NO20012522L (no) | 2001-07-24 |
| ZA200104139B (en) | 2003-01-15 |
| AU757805B2 (en) | 2003-03-06 |
| DE69925859T2 (de) | 2006-05-11 |
| ID28795A (id) | 2001-07-05 |
| DK1134219T3 (da) | 2005-10-17 |
| IL143210A (en) | 2006-04-10 |
| KR100652470B1 (ko) | 2006-12-01 |
| CN1173971C (zh) | 2004-11-03 |
| AU1186200A (en) | 2000-06-13 |
| PT1134219E (pt) | 2005-09-30 |
| MY125894A (en) | 2006-08-30 |
| TW542832B (en) | 2003-07-21 |
| CA2351497A1 (en) | 2000-06-02 |
| US6573260B1 (en) | 2003-06-03 |
| WO2000031062A1 (fr) | 2000-06-02 |
| NO20012522D0 (no) | 2001-05-22 |
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