NO321528B1 - Cykloalkyl-substituerte aminometylpyrrolidin-derivater, og antibakterielle midler inneholdende slike forbindelser - Google Patents

Cykloalkyl-substituerte aminometylpyrrolidin-derivater, og antibakterielle midler inneholdende slike forbindelser Download PDF

Info

Publication number: NO321528B1
Authority: NO; Norway
Prior art keywords: compound; group; formula; amino; cyclopropyl
Prior art date: 1998-11-24

Application number

NO20012522A

Other languages

English (en)

Norwegian (no)

Other versions

NO20012522L (no

NO20012522D0 (no

Inventor

Isao Hayakawa

Makoto Takemura

Hisashi Takahashi

Rie Miyauchi

Toshiyuki Takeda

Original Assignee

Daiichi Seiyaku Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-11-24

Filing date

2001-05-22

Publication date

2006-05-15

2001-05-22 Application filed by Daiichi Seiyaku Co filed Critical Daiichi Seiyaku Co

2001-05-22 Publication of NO20012522D0 publication Critical patent/NO20012522D0/no

2001-07-24 Publication of NO20012522L publication Critical patent/NO20012522L/no

2006-05-15 Publication of NO321528B1 publication Critical patent/NO321528B1/no

Links

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
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
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
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
238000009472 formulation Methods 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
230000014759 maintenance of location Effects 0.000 description 4
238000002156 mixing Methods 0.000 description 4
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
230000008020 evaporation Effects 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000002198 insoluble material Substances 0.000 description 3
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206010039447 salmonellosis Diseases 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
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
TWFKEGONKTUVSX-UHFFFAOYSA-N 1-cyclopropylprop-2-en-1-one Chemical compound C=CC(=O)C1CC1 TWFKEGONKTUVSX-UHFFFAOYSA-N 0.000 description 2
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
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 2
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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102100025142 Beta-microseminoprotein Human genes 0.000 description 2
241000283690 Bos taurus Species 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
208000003322 Coinfection Diseases 0.000 description 2
241000194033 Enterococcus Species 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
206010061190 Haemophilus infection Diseases 0.000 description 2
241000282412 Homo Species 0.000 description 2
101100185029 Homo sapiens MSMB gene Proteins 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
GSDSWSVVBLHKDQ-JTQLQIEISA-N Levofloxacin Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-JTQLQIEISA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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241000204031 Mycoplasma Species 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
206010035664 Pneumonia Diseases 0.000 description 2
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241000191940 Staphylococcus Species 0.000 description 2
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QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
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PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
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CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
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230000009885 systemic effect Effects 0.000 description 1
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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)

NO20012522A 1998-11-24 2001-05-22 Cykloalkyl-substituerte aminometylpyrrolidin-derivater, og antibakterielle midler inneholdende slike forbindelser NO321528B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP33223598		1998-11-24
PCT/JP1999/006521 WO2000031062A1 (en)	1998-11-24	1999-11-22	Cycloalkyl-substituted aminomethylpyrrolidine derivatives

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 (21)

Country	Link
US (1)	US6573260B1 (da)
EP (1)	EP1134219B1 (da)
KR (1)	KR100652470B1 (da)
CN (1)	CN1173971C (da)
AR (1)	AR028806A1 (da)
AT (1)	ATE297912T1 (da)
AU (1)	AU757805B2 (da)
BR (1)	BR9915599A (da)
CA (1)	CA2351497A1 (da)
DE (1)	DE69925859T2 (da)
DK (1)	DK1134219T3 (da)
ES (1)	ES2244248T3 (da)
ID (1)	ID28795A (da)
IL (2)	IL143210A0 (da)
MY (1)	MY125894A (da)
NO (1)	NO321528B1 (da)
PT (1)	PT1134219E (da)
RU (1)	RU2248970C2 (da)
TW (1)	TW542832B (da)
WO (1)	WO2000031062A1 (da)
ZA (1)	ZA200104139B (da)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE60130359T2 (de)	2000-11-20	2008-06-26	Daiichi Sankyo Co., Ltd.	Deshalogenverbindungen
US6818787B2 (en)	2001-06-11	2004-11-16	Xenoport, Inc.	Prodrugs of GABA analogs, compositions and uses thereof
US7232924B2 (en)	2001-06-11	2007-06-19	Xenoport, Inc.	Methods for synthesis of acyloxyalkyl derivatives of GABA analogs
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
MY162052A (en) *	2007-01-05	2017-05-31	Daiichi Sankyo Co Ltd	Fused substitute aminopyrrolidine derivative
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 (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4920120A (en) *	1988-01-25	1990-04-24	Warner-Lambert Company	Antibacterial agents
IL90062A (en) *	1988-04-27	1994-10-07	Daiichi Seiyaku Co	Pyridonecarboxylic acid derivatives, their preparation and pharmaceutical compositions 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
DE4120646A1 (de) *	1991-06-22	1992-12-24	Bayer Ag	7-isoindolinyl-chinolon- und naphthyridoncarbonsaeure-derivate
KR19990022524A (ko)	1995-06-06	1999-03-25	웨인스톡 스티븐 에프.	퀴놀리지논형화합물
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
SK286420B6 (sk) *	1997-09-15	2008-09-05	The Procter & Gamble Company	Zlúčenina so štruktúrou chinolónu, farmaceutický prostriedok s jej obsahom a jej použitie

1999
- 1999-11-22 ES ES99972631T patent/ES2244248T3/es not_active Expired - Lifetime
- 1999-11-22 BR BR9915599-0A patent/BR9915599A/pt not_active Application Discontinuation
- 1999-11-22 IL IL14321099A patent/IL143210A0/xx active IP Right Grant
- 1999-11-22 AT AT99972631T patent/ATE297912T1/de not_active IP Right Cessation
- 1999-11-22 US US09/856,631 patent/US6573260B1/en not_active Expired - Fee Related
- 1999-11-22 AU AU11862/00A patent/AU757805B2/en not_active Ceased
- 1999-11-22 CA CA002351497A patent/CA2351497A1/en not_active Abandoned
- 1999-11-22 WO PCT/JP1999/006521 patent/WO2000031062A1/ja not_active Ceased
- 1999-11-22 RU RU2001114213/04A patent/RU2248970C2/ru not_active IP Right Cessation
- 1999-11-22 DK DK99972631T patent/DK1134219T3/da active
- 1999-11-22 CN CNB998158380A patent/CN1173971C/zh not_active Expired - Fee Related
- 1999-11-22 KR KR1020017006537A patent/KR100652470B1/ko not_active Expired - Fee Related
- 1999-11-22 ID IDW00200101127A patent/ID28795A/id unknown
- 1999-11-22 EP EP99972631A patent/EP1134219B1/en not_active Expired - Lifetime
- 1999-11-22 DE DE69925859T patent/DE69925859T2/de not_active Expired - Fee Related
- 1999-11-22 PT PT99972631T patent/PT1134219E/pt unknown
- 1999-11-22 MY MYPI99005083A patent/MY125894A/en unknown
- 1999-11-24 TW TW088120516A patent/TW542832B/zh not_active IP Right Cessation
- 1999-11-24 AR ARP990105976A patent/AR028806A1/es active IP Right Grant
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

Also Published As

Publication number	Publication date
US6573260B1 (en)	2003-06-03
MY125894A (en)	2006-08-30
CA2351497A1 (en)	2000-06-02
DE69925859T2 (de)	2006-05-11
KR100652470B1 (ko)	2006-12-01
ID28795A (id)	2001-07-05
RU2248970C2 (ru)	2005-03-27
CN1173971C (zh)	2004-11-03
ZA200104139B (en)	2003-01-15
ES2244248T3 (es)	2005-12-01
NO20012522L (no)	2001-07-24
AU757805B2 (en)	2003-03-06
ATE297912T1 (de)	2005-07-15
HK1037635A1 (en)	2002-02-15
IL143210A0 (en)	2002-04-21
IL143210A (en)	2006-04-10
EP1134219B1 (en)	2005-06-15
CN1333765A (zh)	2002-01-30
BR9915599A (pt)	2001-11-20
NO20012522D0 (no)	2001-05-22
EP1134219A4 (en)	2002-11-06
DK1134219T3 (da)	2005-10-17
WO2000031062A1 (en)	2000-06-02
PT1134219E (pt)	2005-09-30
KR20010080564A (ko)	2001-08-22
EP1134219A1 (en)	2001-09-19
AR028806A1 (es)	2003-05-28
TW542832B (en)	2003-07-21
AU1186200A (en)	2000-06-13
DE69925859D1 (en)	2005-07-21

Publication	Publication Date	Title
US5849757A (en)	1998-12-15	Pyridonecarboxylic acid derivatives substituted by a bicyclic amino group as antibacterials
US6573260B1 (en)	2003-06-03	Cycloalkyl-substituted aminomethylpyrrolidine derivatives
US6184388B1 (en)	2001-02-06	Substituted aminocycloalkylpyrrolidine derivatives and cis-substituted aminocycloalkylpyrrolidine derivatives
CA2238765A1 (en)	1997-05-29	Substituted aminocycloalkylpyrrolidine derivatives
US6391889B2 (en)	2002-05-21	Cis-substituted aminocyclopropane derivatives
US6762181B1 (en)	2004-07-13	Aminomethylpyrrolidine derivatives having aromatic substituents
EP0995744B1 (en)	2003-02-12	Cis-substituted fluoromethylpyrrolidine derivatives
JPWO1998002431A1 (ja)	1999-08-24	シス置換アミノシクロプロパン誘導体
AU732175B2 (en)	2001-04-12	Substituted cyclobutylamine derivative
JPWO1998054169A1 (ja)	2000-12-05	置換シクロブチルアミン誘導体
HK1037635B (en)	2005-10-07	Cycloalkyl-substituted aminomethylpyrrolidine derivatives
MXPA01005206A (en)	2003-11-07	Cycloalkyl-substituted aminomethylpyrrolidine derivatives
JPWO2000031062A1 (ja)	2002-03-05	シクロアルキル置換アミノメチルピロリジン誘導体
JPH1081682A (ja)	1998-03-31	シス置換アミノシクロプロパン誘導体
EP0816355A1 (en)	1998-01-07	Heterocyclic spiro derivatives
HK1019064A (en)	2000-01-21	Substituted aminocycloalkylpyrrolidine derivatives
MXPA99011056A (en)	2000-09-04	Substituted cyclobutylamine derivatives