IL107596A - Crystalline carbapenem derivatives, pharmaceutical compositions containing the same and methods for the preparation thereof - Google Patents

Crystalline carbapenem derivatives, pharmaceutical compositions containing the same and methods for the preparation thereof

Info

Publication number: IL107596A
Authority: IL; Israel
Prior art keywords: compound; formula; doublet; crystals; crystalline form
Prior art date: 1992-11-17

Application number

IL107596A

Other languages

English (en)

Other versions

IL107596A0 (en

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.)

1992-11-17

Filing date

1993-11-12

Publication date

1998-02-08

1993-11-12 Application filed by Sankyo Co filed Critical Sankyo Co

1994-02-27 Publication of IL107596A0 publication Critical patent/IL107596A0/xx

1998-02-08 Publication of IL107596A publication Critical patent/IL107596A/en

Links

238000000034 method Methods 0.000 title claims description 22
238000002360 preparation method Methods 0.000 title claims description 21
239000008194 pharmaceutical composition Substances 0.000 title claims description 4
YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical class C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 title abstract description 8
-1 pivaloyloxymethyl ester Chemical class 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims description 48
239000013078 crystal Substances 0.000 claims description 42
239000002904 solvent Substances 0.000 claims description 24
239000000843 powder Substances 0.000 claims description 14
238000002844 melting Methods 0.000 claims description 11
230000008018 melting Effects 0.000 claims description 11
238000002441 X-ray diffraction Methods 0.000 claims description 6
230000003115 biocidal effect Effects 0.000 claims description 6
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
229910052802 copper Inorganic materials 0.000 claims description 5
239000010949 copper Substances 0.000 claims description 5
238000011282 treatment Methods 0.000 claims description 5
239000003242 anti bacterial agent Substances 0.000 claims description 4
208000035143 Bacterial infection Diseases 0.000 claims description 3
241000124008 Mammalia Species 0.000 claims description 3
208000022362 bacterial infectious disease Diseases 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
238000001035 drying Methods 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
238000002955 isolation Methods 0.000 claims description 2
238000011321 prophylaxis Methods 0.000 claims description 2
238000005406 washing Methods 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 2
CTEFNVKDRWMZSL-CTNSIQBBSA-N (4r,5s,6s)-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(3r)-5-oxopyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 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]1CNC(=O)C1 CTEFNVKDRWMZSL-CTNSIQBBSA-N 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
239000000203 mixture Substances 0.000 description 43
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
238000001704 evaporation Methods 0.000 description 22
230000008020 evaporation Effects 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
238000001914 filtration Methods 0.000 description 8
238000000862 absorption spectrum Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
RCGMCMAJECIOHO-RXMQYKEDSA-N s-[(3r)-5-oxopyrrolidin-3-yl] ethanethioate Chemical compound CC(=O)S[C@H]1CNC(=O)C1 RCGMCMAJECIOHO-RXMQYKEDSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
230000003287 optical effect Effects 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
239000003480 eluent Substances 0.000 description 4
238000010828 elution Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
IOGISYQVOGVIEU-UHFFFAOYSA-N (-4-Hydroxy-2-pyrrolidone Natural products OC1CNC(=O)C1 IOGISYQVOGVIEU-UHFFFAOYSA-N 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
IOGISYQVOGVIEU-VKHMYHEASA-N (4s)-4-hydroxypyrrolidin-2-one Chemical compound O[C@@H]1CNC(=O)C1 IOGISYQVOGVIEU-VKHMYHEASA-N 0.000 description 2
JYWKEVKEKOTYEX-UHFFFAOYSA-N 2,6-dibromo-4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=C(Br)C(=O)C(Br)=C1 JYWKEVKEKOTYEX-UHFFFAOYSA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000588724 Escherichia coli Species 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
241000191967 Staphylococcus aureus Species 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000000783 alginic acid Substances 0.000 description 2
235000010443 alginic acid Nutrition 0.000 description 2
229920000615 alginic acid Polymers 0.000 description 2
229960001126 alginic acid Drugs 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
239000001506 calcium phosphate Substances 0.000 description 2
229910000389 calcium phosphate Inorganic materials 0.000 description 2
235000011010 calcium phosphates Nutrition 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
PELJISAVHGXLAL-UHFFFAOYSA-N iodomethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCI PELJISAVHGXLAL-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
244000000010 microbial pathogen Species 0.000 description 2
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 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
238000012360 testing method Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
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 2
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 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
DVLFYONBTKHTER-UHFFFAOYSA-N 3-(N-morpholino)propanesulfonic acid Chemical compound OS(=O)(=O)CCCN1CCOCC1 DVLFYONBTKHTER-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
241000606124 Bacteroides fragilis Species 0.000 description 1
108020004256 Beta-lactamase Proteins 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
241000588914 Enterobacter Species 0.000 description 1
241000194032 Enterococcus faecalis Species 0.000 description 1
241000192125 Firmicutes Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241000588747 Klebsiella pneumoniae Species 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
241000589517 Pseudomonas aeruginosa Species 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
241000607720 Serratia Species 0.000 description 1
241000607768 Shigella Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910000318 alkali metal phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
229940032049 enterococcus faecalis Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
244000005700 microbiome Species 0.000 description 1
239000008183 oral pharmaceutical preparation Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000008055 phosphate buffer solution Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
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150000003462 sulfoxides Chemical class 0.000 description 1
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235000012222 talc Nutrition 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
241001148471 unidentified anaerobic bacterium Species 0.000 description 1
210000002700 urine Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole Compounds (AREA)

IL107596A 1992-11-17 1993-11-12 Crystalline carbapenem derivatives, pharmaceutical compositions containing the same and methods for the preparation thereof IL107596A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP30688492		1992-11-17
JP17026793		1993-07-09

Publications (2)

Publication Number	Publication Date
IL107596A0 IL107596A0 (en)	1994-02-27
IL107596A true IL107596A (en)	1998-02-08

Family

ID=26493307

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL107596A IL107596A (en)	1992-11-17	1993-11-12	Crystalline carbapenem derivatives, pharmaceutical compositions containing the same and methods for the preparation thereof

Country Status (20)

Country	Link
US (1)	US5424306A (de)
EP (1)	EP0599512B1 (de)
JP (1)	JP2848552B2 (de)
KR (1)	KR100236845B1 (de)
CN (1)	CN1036714C (de)
AT (1)	ATE178066T1 (de)
AU (1)	AU677235B2 (de)
CA (1)	CA2103223C (de)
CZ (1)	CZ280507B6 (de)
DE (1)	DE69324106T2 (de)
DK (1)	DK0599512T3 (de)
ES (1)	ES2131560T3 (de)
FI (1)	FI103576B (de)
GR (1)	GR3029975T3 (de)
HU (1)	HU219582B (de)
IL (1)	IL107596A (de)
NO (1)	NO304431B1 (de)
NZ (1)	NZ250201A (de)
PH (1)	PH30464A (de)
TW (1)	TW360657B (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
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WO1997041853A1 (en) *	1996-05-09	1997-11-13	Sankyo Company, Limited	Anti-helicobacter pylori compositions containing 1-methylcarbapenem derivatives as the active ingredient
US7041660B2 (en) *	1999-07-06	2006-05-09	Sankyo Company, Limited	Crystalline 1-methylcarbapenem derivatives
TWI250160B (en)	1999-07-06	2006-03-01	Sankyo Co	Crystalline 1-methylcarbapenem compound
KR100451672B1 (ko) *	2001-06-05	2004-10-08	한미약품 주식회사	결정성 세프디니르 산부가염, 이의 제조방법 및 이를이용한 세프디니르의 제조방법
ITMI20012364A1 (it) *	2001-11-09	2003-05-09	Antibioticos Spa	Processo di sintesi della cefixima via alchil-o arilsolfonati
EP2316468A1 (de)	2002-02-22	2011-05-04	Shire LLC	Abgabesystem und Verfahren zum Schutz und zur Verabreichung von Dextroamphetamin
WO2004035539A1 (ja) *	2002-10-18	2004-04-29	Meiji Seika Kaisha, Ltd.	カルバペネム類の製造方法およびその製造に用いられる中間体
US20070249827A1 (en) *	2004-06-02	2007-10-25	Sandoz Ag	Meropenem Intermediatein in Crystalling Form
JP2009143808A (ja) *	2006-03-28	2009-07-02	Kaneka Corp	メロペネム中間体の単離方法
ES2602566T3 (es)	2007-01-12	2017-02-21	Novartis Ag	Proceso para preparar ácido 5-bifenil-4-amino-2-metil pentanoico

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE68919508T2 (de) *	1988-04-01	1995-07-20	Sankyo Co	2-(Heterocyclylthio)carbapenemderivate, deren Herstellung und deren Verwendung als Antibiotika.
US5242914A (en) *	1988-04-01	1993-09-07	Sankyo Company, Limited	2-(heterocyclylthio) carbapenem derivatives, their preparation and their use as antibiotics
JPH0745499B2 (ja) *	1988-05-10	1995-05-17	三共株式会社	１―メチルカルバペネム誘導体
EP0462521A1 (de) *	1990-06-19	1991-12-27	Takeda Chemical Industries, Ltd.	Kristallines Penem, Herstellung und Verwendung

1993
- 1993-11-09 AT AT93308921T patent/ATE178066T1/de not_active IP Right Cessation
- 1993-11-09 EP EP93308921A patent/EP0599512B1/de not_active Expired - Lifetime
- 1993-11-09 DE DE69324106T patent/DE69324106T2/de not_active Expired - Fee Related
- 1993-11-09 ES ES93308921T patent/ES2131560T3/es not_active Expired - Lifetime
- 1993-11-09 DK DK93308921T patent/DK0599512T3/da active
- 1993-11-11 AU AU50631/93A patent/AU677235B2/en not_active Ceased
- 1993-11-12 US US08/151,517 patent/US5424306A/en not_active Expired - Fee Related
- 1993-11-12 IL IL107596A patent/IL107596A/en not_active IP Right Cessation
- 1993-11-15 NZ NZ250201A patent/NZ250201A/en unknown
- 1993-11-16 TW TW082109560A patent/TW360657B/zh active
- 1993-11-16 NO NO934140A patent/NO304431B1/no not_active IP Right Cessation
- 1993-11-16 HU HU9303245A patent/HU219582B/hu not_active IP Right Cessation
- 1993-11-16 JP JP5285444A patent/JP2848552B2/ja not_active Expired - Fee Related
- 1993-11-16 FI FI935063A patent/FI103576B/fi not_active IP Right Cessation
- 1993-11-16 CA CA002103223A patent/CA2103223C/en not_active Expired - Fee Related
- 1993-11-16 PH PH47271A patent/PH30464A/en unknown
- 1993-11-17 CN CN93121439A patent/CN1036714C/zh not_active Expired - Fee Related
- 1993-11-17 CZ CZ932454A patent/CZ280507B6/cs not_active IP Right Cessation
- 1993-11-17 KR KR1019930024477A patent/KR100236845B1/ko not_active Expired - Fee Related
1999
- 1999-04-16 GR GR990401054T patent/GR3029975T3/el unknown

Also Published As

Publication number	Publication date
GR3029975T3 (en)	1999-07-30
PH30464A (en)	1997-05-28
TW360657B (en)	1999-06-11
DK0599512T3 (da)	1999-10-11
CA2103223C (en)	2002-09-24
CA2103223A1 (en)	1994-05-18
AU5063193A (en)	1994-06-02
US5424306A (en)	1995-06-13
HK1011977A1 (en)	1999-07-23
HU219582B (hu)	2001-05-28
FI935063L (fi)	1994-05-18
CZ245493A3 (en)	1995-08-16
NO934140L (no)	1994-05-18
JPH07165759A (ja)	1995-06-27
ATE178066T1 (de)	1999-04-15
NZ250201A (en)	1995-04-27
DE69324106T2 (de)	1999-12-09
EP0599512A1 (de)	1994-06-01
AU677235B2 (en)	1997-04-17
IL107596A0 (en)	1994-02-27
CN1093366A (zh)	1994-10-12
FI103576B1 (fi)	1999-07-30
NO934140D0 (no)	1993-11-16
JP2848552B2 (ja)	1999-01-20
KR100236845B1 (ko)	2000-02-01
NO304431B1 (no)	1998-12-14
KR940011463A (ko)	1994-06-21
HUT66001A (en)	1994-08-29
ES2131560T3 (es)	1999-08-01
FI103576B (fi)	1999-07-30
FI935063A0 (fi)	1993-11-16
EP0599512B1 (de)	1999-03-24
CZ280507B6 (cs)	1996-02-14
DE69324106D1 (de)	1999-04-29
CN1036714C (zh)	1997-12-17

Legal Events

Date	Code	Title
1998-07-15	FF	Patent granted
1998-12-06	KB	Patent renewed
2000-07-26	KB	Patent renewed
2000-08-31	KB	Patent renewed
2004-01-04	KB	Patent renewed
2008-11-03	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
AU2002348986B2 (en)	2008-04-03	Formulations comprising a cephalosporin compound and their use treating bacterial infections in cats and dogs
DE2837264A1 (de)	1979-03-01	7 beta -arylmalonamido-7 alpha -methoxy-3-thiadiazolylthio-1-oxadethiacephalosporine, ihre ester und salze, sowie verfahren zu deren herstellung
US5424306A (en)	1995-06-13	Crystalline carbapenem derivative
WO2017216765A1 (en)	2017-12-21	Antibacterial compositions
KR100472842B1 (ko)	2005-03-10	피롤리딜티오카르바페넴 유도체의 신형결정
DE3019244C2 (de)	1989-04-06
EP0329008B1 (de)	1999-08-11	Cephalosporinderivative und Verfahren zu ihrer Herstellung
US4123547A (en)	1978-10-31	Thienamycin sulfoxide and sulphone
EP0301394B1 (de)	1993-10-06	Stabile Oxapenem- 3-carbonsäuren
JPS60233077A (ja)	1985-11-19	１‐テヘロ‐６‐〔１‐ヒドロキシエチル〕‐２‐ｓｒ↑８‐１‐カルバデチアペン‐２‐エム‐３‐カルボン酸
US4123539A (en)	1978-10-31	6-Ethylpenicillanic acid
JPS60233078A (ja)	1985-11-19	６‐〔１‐ヒドロキシエチル〕‐２‐ｓｒ↑８‐１‐メチル‐１‐カルバデチアペン‐２‐エム‐３‐カルボン酸
RU2090567C1 (ru)	1997-09-20	Кристаллический пивалоилоксиметил (ir, 5s, 6s)-[(4r)-2-оксо-4-пирролидинилтио]-6-[(ir)-1-гидроксиэтил]-1-метил-1-карбапен-2-ем-3-карбоксилат и способ его получения
CH640236A5 (en)	1983-12-30	3-(2-Aminoethylthio)-6-ethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2 -carboxylic acid and process for its preparation
EP0362622B1 (de)	1995-03-29	Verwendung stabiler Oxapenem-3-carbonsäuren zur Herstellung Beta-Lactamase hemmender Arzneimittel
HK1011977B (en)	2000-04-07	Crystalline carbapenem derivative
DE69909098T2 (de)	2004-04-08	C-2 s/o- und s/n-formaldehydacetal-derivate von carbapenem-3-carbonsäuren und deren verwendung als antibiotika und beta-lactamas-inhibitoren
DE69829720T2 (de)	2006-03-09	Antimikrobielle Zusammensetzungen welche Vinylpyrrolidinon-Cephalosporin-Derivate und ein Carbapenemantibiotikum oder ein beta-lactamaseinhibitor enthaten
DE69130363T2 (de)	1999-04-22	Antibakterielle penemverbindungen
EP0548790B1 (de)	1996-05-01	(1'S)-Hydroxyalkyloxapenem-3-carbonsäuren und ihre Verwendung als Betalactamasehemmer
DE2819453C2 (de)	1993-02-25
CA1202617A (en)	1986-04-01	Bacampicillin napsylate
WO1995014692A1 (en)	1995-06-01	Cabapenem derivatives and processes for preparing the same
DE2818985C2 (de)	1995-08-17	Halogenarylmalonamidooxacephalosporine und deren Verwendung bei der Bekämpfung bakterieller Infektionen
AU2002348985A1 (en)	2003-07-09	Methods of treating bacterial infections in dogs and cats