NO312900B1 - 1-metylkarbapenemderivater, preparat inneholdende dette og anvendelse derav for fremstilling av et medikament - Google Patents

1-metylkarbapenemderivater, preparat inneholdende dette og anvendelse derav for fremstilling av et medikament Download PDF

Info

Publication number: NO312900B1
Authority: NO; Norway
Prior art keywords: compound; group; reaction; reaction mixture; methyl
Prior art date: 1996-04-26

Application number

NO19984948A

Other languages

English (en)

Norwegian (no)

Other versions

NO984948D0 (no

NO984948L (no

Inventor

Isao Kawamoto

Katsuya Ishikawa

Katsuhiko Kojima

Yasuo Shimoji

Satoshi Ohya

Munetsugu Morimoto

Original Assignee

Sankyo 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.)

1996-04-26

Filing date

1998-10-23

Publication date

2002-07-15

1998-10-23 Application filed by Sankyo Co filed Critical Sankyo Co

1998-10-23 Publication of NO984948D0 publication Critical patent/NO984948D0/no

1998-12-21 Publication of NO984948L publication Critical patent/NO984948L/no

2002-07-15 Publication of NO312900B1 publication Critical patent/NO312900B1/no

Links

238000002360 preparation method Methods 0.000 title claims description 9
239000003814 drug Substances 0.000 title claims description 4
YKMONJZIUAOVEM-GDVGLLTNSA-N (5S)-4-methyl-1-azabicyclo[3.2.0]hept-2-en-7-one Chemical class CC1C=CN2[C@H]1CC2=O YKMONJZIUAOVEM-GDVGLLTNSA-N 0.000 title abstract description 7
-1 1-methylcarbapenem compound Chemical class 0.000 claims abstract description 73
150000003839 salts Chemical class 0.000 claims abstract description 24
150000001875 compounds Chemical class 0.000 claims description 108
230000002265 prevention Effects 0.000 claims description 8
208000035143 Bacterial infection Diseases 0.000 claims description 7
208000022362 bacterial infectious disease Diseases 0.000 claims description 7
HVWDGGLAJWHDOL-ILJVOIDVSA-N (4r,5s,6s)-6-[(1r)-1-hydroxyethyl]-4-methyl-3-[(3s,5s)-5-[(3r)-3-(methylaminomethyl)pyrrolidine-1-carbonyl]pyrrolidin-3-yl]sulfanyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C1[C@@H](CNC)CCN1C(=O)[C@H]1NC[C@@H](SC=2[C@@H]([C@H]3N(C([C@@H]3[C@@H](C)O)=O)C=2C(O)=O)C)C1 HVWDGGLAJWHDOL-ILJVOIDVSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
230000000844 anti-bacterial effect Effects 0.000 abstract description 15
125000001424 substituent group Chemical group 0.000 abstract description 15
125000000217 alkyl group Chemical group 0.000 abstract description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 6
125000003277 amino group Chemical group 0.000 abstract description 5
208000015181 infectious disease Diseases 0.000 abstract description 5
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
230000003449 preventive effect Effects 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
229910052739 hydrogen Inorganic materials 0.000 description 45
239000000203 mixture Substances 0.000 description 43
239000011541 reaction mixture Substances 0.000 description 43
238000006243 chemical reaction Methods 0.000 description 40
239000000243 solution Substances 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 28
230000002829 reductive effect Effects 0.000 description 26
125000006239 protecting group Chemical group 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
239000002904 solvent Substances 0.000 description 24
238000000034 method Methods 0.000 description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 20
238000001704 evaporation Methods 0.000 description 18
230000008020 evaporation Effects 0.000 description 18
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
238000004587 chromatography analysis Methods 0.000 description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
239000012044 organic layer Substances 0.000 description 14
238000003756 stirring Methods 0.000 description 13
238000000862 absorption spectrum Methods 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
239000002585 base Substances 0.000 description 11
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
238000012360 testing method Methods 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
101150041968 CDC13 gene Proteins 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
241000589517 Pseudomonas aeruginosa Species 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
DMJNNHOOLUXYBV-PQTSNVLCSA-N meropenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](C(=O)N(C)C)C1 DMJNNHOOLUXYBV-PQTSNVLCSA-N 0.000 description 8
229960002260 meropenem Drugs 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
239000003960 organic solvent Substances 0.000 description 8
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 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
239000001301 oxygen Substances 0.000 description 7
229910052760 oxygen Inorganic materials 0.000 description 7
239000000047 product Substances 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
206010029155 Nephropathy toxic Diseases 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
239000003638 chemical reducing agent Substances 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
238000000605 extraction Methods 0.000 description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
230000007694 nephrotoxicity Effects 0.000 description 6
231100000417 nephrotoxicity Toxicity 0.000 description 6
231100000989 no adverse effect Toxicity 0.000 description 6
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
230000035484 reaction time Effects 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
239000003242 anti bacterial agent Substances 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
238000009472 formulation Methods 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
239000000546 pharmaceutical excipient Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
241000894006 Bacteria Species 0.000 description 4
229940126062 Compound A Drugs 0.000 description 4
102000003850 Dipeptidase 1 Human genes 0.000 description 4
108090000204 Dipeptidase 1 Proteins 0.000 description 4
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000003480 eluent Substances 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000003826 tablet Substances 0.000 description 4
238000005406 washing Methods 0.000 description 4
MHSGOABISYIYKP-UHFFFAOYSA-N (4-nitrophenyl)methyl carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(COC(Cl)=O)C=C1 MHSGOABISYIYKP-UHFFFAOYSA-N 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
BSIMZHVOQZIAOY-SCSAIBSYSA-N 1-carbapenem-3-carboxylic acid Chemical compound OC(=O)C1=CC[C@@H]2CC(=O)N12 BSIMZHVOQZIAOY-SCSAIBSYSA-N 0.000 description 3
LVGIUOZGDVZIMK-UHFFFAOYSA-N 1-sulfanylpyrrolidine Chemical class SN1CCCC1 LVGIUOZGDVZIMK-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 3
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241001465754 Metazoa Species 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
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239000010410 layer Substances 0.000 description 3
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150000002825 nitriles Chemical class 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
230000000865 phosphorylative effect Effects 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
238000011084 recovery Methods 0.000 description 3
238000001226 reprecipitation Methods 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
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239000000126 substance Substances 0.000 description 3
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PDVFSPNIEOYOQL-UHFFFAOYSA-N (4-methylphenyl)sulfonyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OS(=O)(=O)C1=CC=C(C)C=C1 PDVFSPNIEOYOQL-UHFFFAOYSA-N 0.000 description 2
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
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229920001817 Agar Polymers 0.000 description 2
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IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
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229910052794 bromium Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
239000001175 calcium sulphate Substances 0.000 description 1
235000011132 calcium sulphate Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
229920003123 carboxymethyl cellulose sodium Polymers 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
229940105329 carboxymethylcellulose Drugs 0.000 description 1
229940084030 carboxymethylcellulose calcium Drugs 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
229960004926 chlorobutanol Drugs 0.000 description 1
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
DHSUYTOATWAVLW-WFVMDLQDSA-N cilastatin Chemical compound CC1(C)C[C@@H]1C(=O)N\C(=C/CCCCSC[C@H](N)C(O)=O)C(O)=O DHSUYTOATWAVLW-WFVMDLQDSA-N 0.000 description 1
229960004912 cilastatin Drugs 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
150000003946 cyclohexylamines Chemical class 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
JAUGGEIKQIHSMF-UHFFFAOYSA-N dialuminum;dimagnesium;dioxido(oxo)silane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O JAUGGEIKQIHSMF-UHFFFAOYSA-N 0.000 description 1
125000006003 dichloroethyl group Chemical group 0.000 description 1
125000006001 difluoroethyl group Chemical group 0.000 description 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical class CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
CCJXQRNXZKSOGJ-UHFFFAOYSA-N ethylsulfonyl ethanesulfonate Chemical compound CCS(=O)(=O)OS(=O)(=O)CC CCJXQRNXZKSOGJ-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
125000003630 glycyl group Chemical class [H]N([H])C([H])([H])C(*)=O 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
ZSKVGTPCRGIANV-ZXFLCMHBSA-N imipenem Chemical compound C1C(SCC\N=C\N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 ZSKVGTPCRGIANV-ZXFLCMHBSA-N 0.000 description 1
229960002182 imipenem Drugs 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000011835 investigation Methods 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229960003511 macrogol Drugs 0.000 description 1
229940037627 magnesium lauryl sulfate Drugs 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
HBNDBUATLJAUQM-UHFFFAOYSA-L magnesium;dodecyl sulfate Chemical compound [Mg+2].CCCCCCCCCCCCOS([O-])(=O)=O.CCCCCCCCCCCCOS([O-])(=O)=O HBNDBUATLJAUQM-UHFFFAOYSA-L 0.000 description 1
229940049920 malate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
CEAJFNBWKBTRQE-UHFFFAOYSA-N methanamine;methanol Chemical compound NC.OC CEAJFNBWKBTRQE-UHFFFAOYSA-N 0.000 description 1
IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000006916 nutrient agar Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
229950011346 panipenem Drugs 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229940067107 phenylethyl alcohol Drugs 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229940068968 polysorbate 80 Drugs 0.000 description 1
IXRMKTUAQDWCIF-UHFFFAOYSA-L potassium sodium 2-ethylhexanoate Chemical compound C(C)C(C(=O)[O-])CCCC.[K+].C(C)C(C(=O)[O-])CCCC.[Na+] IXRMKTUAQDWCIF-UHFFFAOYSA-L 0.000 description 1
DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
238000000039 preparative column chromatography Methods 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
235000019423 pullulan Nutrition 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
OQCUGPQOZNYIMV-UHFFFAOYSA-N pyrrolidin-3-ylmethanamine Chemical compound NCC1CCNC1 OQCUGPQOZNYIMV-UHFFFAOYSA-N 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
125000005624 silicic acid group Chemical class 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
OIIWPAYIXDCDNL-HGFPCDIYSA-M sodium;2,2,3,3-tetradeuterio-3-trimethylsilylpropanoate Chemical compound [Na+].[O-]C(=O)C([2H])([2H])C([2H])([2H])[Si](C)(C)C OIIWPAYIXDCDNL-HGFPCDIYSA-M 0.000 description 1
239000002195 soluble material Substances 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
MWACHFODPQVXHF-CYBMUJFWSA-N tert-butyl (3r)-3-(4-methylphenyl)sulfonyloxypyrrolidine-1-carboxylate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)O[C@H]1CN(C(=O)OC(C)(C)C)CC1 MWACHFODPQVXHF-CYBMUJFWSA-N 0.000 description 1
OGCCBDIYOAFOGK-MRVPVSSYSA-N tert-butyl (3r)-3-(aminomethyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@H](CN)C1 OGCCBDIYOAFOGK-MRVPVSSYSA-N 0.000 description 1
ZWHKCVQACIGDTP-OAHLLOKOSA-N tert-butyl (3r)-3-[[methyl-[(4-nitrophenyl)methoxycarbonyl]amino]methyl]pyrrolidine-1-carboxylate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1COC(=O)N(C)C[C@H]1CCN(C(=O)OC(C)(C)C)C1 ZWHKCVQACIGDTP-OAHLLOKOSA-N 0.000 description 1
VDDMCMFPUSCJNA-QMMMGPOBSA-N tert-butyl (3r)-3-cyanopyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@@H](C#N)C1 VDDMCMFPUSCJNA-QMMMGPOBSA-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
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229940033663 thimerosal Drugs 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000005550 wet granulation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
- C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 3
- C07D477/20—Sulfur atoms
- 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)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO19984948A 1996-04-26 1998-10-23 1-metylkarbapenemderivater, preparat inneholdende dette og anvendelse derav for fremstilling av et medikament NO312900B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP10736496		1996-04-26
PCT/JP1997/001452 WO1997041123A1 (en)	1996-04-26	1997-04-25	1-methylcarbapenem derivatives

Publications (3)

Publication Number	Publication Date
NO984948D0 NO984948D0 (no)	1998-10-23
NO984948L NO984948L (no)	1998-12-21
NO312900B1 true NO312900B1 (no)	2002-07-15

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ID=14457217

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Application Number	Title	Priority Date	Filing Date
NO19984948A NO312900B1 (no)	1996-04-26	1998-10-23	1-metylkarbapenemderivater, preparat inneholdende dette og anvendelse derav for fremstilling av et medikament

Country Status (17)

Country	Link
US (1)	US5977097A (de)
EP (1)	EP0900797B1 (de)
KR (1)	KR20000064997A (de)
CN (1)	CN1093861C (de)
AT (1)	ATE222588T1 (de)
AU (1)	AU710881B2 (de)
CA (1)	CA2252723A1 (de)
CZ (1)	CZ342098A3 (de)
DE (1)	DE69714841T2 (de)
DK (1)	DK0900797T3 (de)
ES (1)	ES2180977T3 (de)
HU (1)	HUP9902149A3 (de)
NO (1)	NO312900B1 (de)
NZ (1)	NZ332453A (de)
PT (1)	PT900797E (de)
RU (1)	RU2162088C2 (de)
WO (1)	WO1997041123A1 (de)

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CN1095843C (zh) *	1995-12-21	2002-12-11	三共株式会社	1－甲基碳代青霉烯衍生物
AU1415500A (en) *	1998-12-07	2000-06-26	Sankyo Company Limited	1-methylcarbapenem derivatives
AU748949B2 (en) *	1999-06-23	2002-06-13	Merck & Co., Inc.	Integrin receptor antagonists
IL160413A0 (en) *	2001-09-26	2004-07-25	Merck & Co Inc	Process for making carbapenem compounds
AU2004296261B2 (en) *	2003-12-09	2007-08-23	Choongwae Pharm. Co.	A new process for preparation of imipenem
WO2008026527A1 (fr) *	2006-08-28	2008-03-06	Kaneka Corporation	Procédé de fabrication d'un dérivé de 3-cyanopyrrolidine ou d'un de ses sels
CN101357917B (zh) *	2007-06-22	2011-03-23	山东轩竹医药科技有限公司	含有甲酰肼基的碳青霉烯化合物
CN101367809B (zh) *	2007-06-28	2011-04-27	山东轩竹医药科技有限公司	含有巯基吡咯烷甲酰肼的培南衍生物
CN101362760B (zh) *	2007-08-07	2010-12-15	山东轩竹医药科技有限公司	1β-甲基碳代青霉烯化合物

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CA1283906C (en) *	1983-05-09	1991-05-07	Makoto Sunagawa	.beta.-LACTAM COMPOUNDS AND PRODUCTION THEREOF
CA1281720C (en) *	1984-11-08	1991-03-19	Makoto Sunagawa	Carbapenem compounds and production thereof
JP2752143B2 (ja) *	1988-04-01	1998-05-18	三共株式会社	カルバペネム誘導体
DE68919508T2 (de) *	1988-04-01	1995-07-20	Sankyo Co	2-(Heterocyclylthio)carbapenemderivate, deren Herstellung und deren Verwendung als Antibiotika.
JPH023687A (ja) *	1988-06-22	1990-01-09	Sankyo Co Ltd	１−メチルカルバペネム誘導体
JPH04211083A (ja) *	1990-02-23	1992-08-03	Sankyo Co Ltd	カルバペネム−３−カルボン酸誘導体
CA2036941A1 (en) *	1990-02-23	1991-08-24	Isao Kawamoto	Carbapenem derivatives having antibiotic activity, their preparation and their use
US5712267A (en) *	1991-06-04	1998-01-27	Sankyo Company,. Limited	Carbapenem derivatives, their preparation and their use as antibiotics
CA2070305A1 (en) *	1991-06-04	1992-12-05	Isao Kawamoto	1-methylcarbapenem derivatives, their preparation and their use as antibiotics
HU218676B (hu) *	1992-03-11	2000-10-28	Sankyo Co. Ltd.	Antimikrobiális karbapenemszármazékok, ilyen vegyületeket tartalmazó gyógyászati készítmények és eljárás ezek előállítására
JP3411589B2 (ja) *	1992-05-11	2003-06-03	第一製薬株式会社	カルバペネム誘導体
JP3344662B2 (ja) *	1992-09-14	2002-11-11	三共株式会社	カルバペネム−３−カルボン酸誘導体
JPH06199860A (ja) *	1992-09-16	1994-07-19	Sankyo Co Ltd	カルバペネム誘導体
JPH07228570A (ja) *	1993-12-22	1995-08-29	Sankyo Co Ltd	４−メルカプトピロリジン誘導体
JP3199300B2 (ja) *	1994-05-09	2001-08-13	三共株式会社	１−メチルカルバペネム誘導体
JPH0848667A (ja) *	1994-06-03	1996-02-20	Sankyo Co Ltd	４−メルカプトピロリジン誘導体

1997
- 1997-04-25 RU RU98119310/04A patent/RU2162088C2/ru not_active IP Right Cessation
- 1997-04-25 CA CA002252723A patent/CA2252723A1/en not_active Abandoned
- 1997-04-25 WO PCT/JP1997/001452 patent/WO1997041123A1/ja not_active Ceased
- 1997-04-25 CN CN97195799A patent/CN1093861C/zh not_active Expired - Fee Related
- 1997-04-25 EP EP97919696A patent/EP0900797B1/de not_active Expired - Lifetime
- 1997-04-25 ES ES97919696T patent/ES2180977T3/es not_active Expired - Lifetime
- 1997-04-25 KR KR1019980708512A patent/KR20000064997A/ko not_active Ceased
- 1997-04-25 DK DK97919696T patent/DK0900797T3/da active
- 1997-04-25 HU HU9902149A patent/HUP9902149A3/hu unknown
- 1997-04-25 AU AU24076/97A patent/AU710881B2/en not_active Ceased
- 1997-04-25 AT AT97919696T patent/ATE222588T1/de not_active IP Right Cessation
- 1997-04-25 NZ NZ332453A patent/NZ332453A/xx unknown
- 1997-04-25 PT PT97919696T patent/PT900797E/pt unknown
- 1997-04-25 CZ CZ983420A patent/CZ342098A3/cs unknown
- 1997-04-25 DE DE69714841T patent/DE69714841T2/de not_active Expired - Fee Related
1998
- 1998-10-22 US US09/176,804 patent/US5977097A/en not_active Expired - Fee Related
- 1998-10-23 NO NO19984948A patent/NO312900B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
KR20000064997A (ko)	2000-11-06
ES2180977T3 (es)	2003-02-16
WO1997041123A1 (en)	1997-11-06
CZ342098A3 (cs)	1999-02-17
CA2252723A1 (en)	1997-11-06
DE69714841D1 (de)	2002-09-26
HUP9902149A2 (hu)	1999-10-28
EP0900797A4 (de)	2000-07-19
DK0900797T3 (da)	2002-09-09
NO984948D0 (no)	1998-10-23
NZ332453A (en)	2000-09-29
EP0900797A1 (de)	1999-03-10
CN1093861C (zh)	2002-11-06
HK1018260A1 (en)	1999-12-17
RU2162088C2 (ru)	2001-01-20
AU710881B2 (en)	1999-09-30
ATE222588T1 (de)	2002-09-15
DE69714841T2 (de)	2003-05-28
NO984948L (no)	1998-12-21
US5977097A (en)	1999-11-02
HUP9902149A3 (en)	2002-01-28
AU2407697A (en)	1997-11-19
CN1223655A (zh)	1999-07-21
PT900797E (pt)	2002-11-29
EP0900797B1 (de)	2002-08-21

Legal Events

Date	Code	Title	Description
2003-12-08	MM1K	Lapsed by not paying the annual fees	Free format text: LAPSED IN OCTOBER 2003

Publication	Publication Date	Title
JP2666118B2 (ja)	1997-10-22	２−［１−（１，３−チアゾリン−２−イル）アゼチジン−３−イル］チオ−カルバペネム化合物
JP2754679B2 (ja)	1998-05-20	３―ピロリジニルチオ―１―アザビシクロ［３．２．０］ヘプト―２―エン―２―カルボン酸化合物
JP2792103B2 (ja)	1998-08-27	３―ピロリジニルチオ―１―アザビシクロ［３．２．０］ヘプト―２―エン―２―カルボン酸化合物
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KR100589030B1 (ko)	2006-06-13	카르바페넴 유도체, 그 사용 방법 및 그 중간체 화합물
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HK1018260B (en)	2003-01-03	A 1-methylcarbapenem derivative
JP2003183282A (ja)	2003-07-03	カルバペネム化合物
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JPH0764846B2 (ja)	1995-07-12	２−（置換ピロリジニルチオ）カルバペネム誘導体
MXPA98008893A (en)	1999-04-27	Derivatives of 1-metilcarbapen
JPH11193232A (ja)	1999-07-21	１−メチルカルバペネム誘導体を含有する抗菌剤
HK1015766B (en)	2003-05-02	1-methylcarbapenem derivatives
JP2000344773A (ja)	2000-12-12	カルバペネム誘導体、およびその用途並びにその中間体化合物
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JPWO2000015640A1 (ja)	2001-11-27	カルバペネム化合物
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