JPH0461849B2 - - Google Patents
Info
- Publication number
- JPH0461849B2 JPH0461849B2 JP59215683A JP21568384A JPH0461849B2 JP H0461849 B2 JPH0461849 B2 JP H0461849B2 JP 59215683 A JP59215683 A JP 59215683A JP 21568384 A JP21568384 A JP 21568384A JP H0461849 B2 JPH0461849 B2 JP H0461849B2
- Authority
- JP
- Japan
- Prior art keywords
- lysine
- formula
- ornithine
- benzoyl
- ethoxycarbonyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- 229960003104 ornithine Drugs 0.000 claims description 34
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 32
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 32
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 17
- 150000002668 lysine derivatives Chemical class 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 230000003115 biocidal effect Effects 0.000 claims description 6
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- 229940088710 antibiotic agent Drugs 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 206010029155 Nephropathy toxic Diseases 0.000 claims description 4
- 230000007694 nephrotoxicity Effects 0.000 claims description 4
- 231100000417 nephrotoxicity Toxicity 0.000 claims description 4
- -1 isobutyryl Chemical group 0.000 description 68
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 18
- 239000004472 Lysine Substances 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 10
- 210000003734 kidney Anatomy 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HHXMXAQDOUCLDN-RXMQYKEDSA-N penem Chemical compound S1C=CN2C(=O)C[C@H]21 HHXMXAQDOUCLDN-RXMQYKEDSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 2
- YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical compound C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CVCQLTQQMALEDZ-XCWJXAQQSA-N (2R)-2,5-diamino-2-benzoyl-6-oxo-6-phenylhexanoic acid Chemical compound NC(CC[C@](N)(C(O)=O)C(=O)c1ccccc1)C(=O)c1ccccc1 CVCQLTQQMALEDZ-XCWJXAQQSA-N 0.000 description 1
- DKFKBNFMYXJNDQ-YFKPBYRVSA-N (2S)-5-amino-2-isocyanatopentanoic acid Chemical compound C(=O)=N[C@@H](CCCN)C(=O)O DKFKBNFMYXJNDQ-YFKPBYRVSA-N 0.000 description 1
- GEIQGKVZWVWVQZ-JTQLQIEISA-N (2s)-5-amino-2-(cyclohexanecarbonylamino)pentanoic acid Chemical compound NCCC[C@@H](C(O)=O)NC(=O)C1CCCCC1 GEIQGKVZWVWVQZ-JTQLQIEISA-N 0.000 description 1
- SVTCKTHFYSBYMF-LURJTMIESA-N (2s)-5-amino-2-(ethoxycarbonylamino)pentanoic acid Chemical compound CCOC(=O)N[C@H](C(O)=O)CCCN SVTCKTHFYSBYMF-LURJTMIESA-N 0.000 description 1
- FMFHPZAFJYWRAH-YFKPBYRVSA-N (2s)-5-amino-2-(methoxycarbonylamino)pentanoic acid Chemical compound COC(=O)N[C@H](C(O)=O)CCCN FMFHPZAFJYWRAH-YFKPBYRVSA-N 0.000 description 1
- PKONOCQSEOHHJW-JTQLQIEISA-N (2s)-5-azaniumyl-2-benzamidopentanoate Chemical compound [NH3+]CCC[C@@H](C([O-])=O)NC(=O)C1=CC=CC=C1 PKONOCQSEOHHJW-JTQLQIEISA-N 0.000 description 1
- DRHCRKHWTWJZJQ-QMMMGPOBSA-N (2s)-6-amino-2-(2-methylpropanoylamino)hexanoic acid Chemical compound CC(C)C(=O)N[C@H](C(O)=O)CCCCN DRHCRKHWTWJZJQ-QMMMGPOBSA-N 0.000 description 1
- VAWJDJJVJBQDHP-QMMMGPOBSA-N (2s)-6-amino-2-(butanoylamino)hexanoic acid Chemical compound CCCC(=O)N[C@H](C(O)=O)CCCCN VAWJDJJVJBQDHP-QMMMGPOBSA-N 0.000 description 1
- WXUPNROOSXELJT-VIFPVBQESA-N (2s)-6-amino-2-(butoxycarbonylamino)hexanoic acid Chemical compound CCCCOC(=O)N[C@H](C(O)=O)CCCCN WXUPNROOSXELJT-VIFPVBQESA-N 0.000 description 1
- SNMHDKLCGMWALN-ZETCQYMHSA-N (2s)-6-amino-2-(ethoxycarbonylamino)hexanoic acid Chemical compound CCOC(=O)N[C@H](C(O)=O)CCCCN SNMHDKLCGMWALN-ZETCQYMHSA-N 0.000 description 1
- QUMLYZRLVFEBQN-LURJTMIESA-N (2s)-6-amino-2-(methoxycarbonylamino)hexanoic acid Chemical compound COC(=O)N[C@H](C(O)=O)CCCCN QUMLYZRLVFEBQN-LURJTMIESA-N 0.000 description 1
- QJVATVNUTAKZJF-VIFPVBQESA-N (2s)-6-amino-2-(pentanoylamino)hexanoic acid Chemical compound CCCCC(=O)N[C@H](C(O)=O)CCCCN QJVATVNUTAKZJF-VIFPVBQESA-N 0.000 description 1
- TVRJDJXBFPCFLT-ZETCQYMHSA-N (2s)-6-amino-2-(propanoylamino)hexanoic acid Chemical compound CCC(=O)N[C@H](C(O)=O)CCCCN TVRJDJXBFPCFLT-ZETCQYMHSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- JRLGPAXAGHMNOL-LURJTMIESA-N N(2)-acetyl-L-ornithine Chemical compound CC(=O)N[C@H](C([O-])=O)CCC[NH3+] JRLGPAXAGHMNOL-LURJTMIESA-N 0.000 description 1
- DTERQYGMUDWYAZ-ZETCQYMHSA-N N(6)-acetyl-L-lysine Chemical compound CC(=O)NCCCC[C@H]([NH3+])C([O-])=O DTERQYGMUDWYAZ-ZETCQYMHSA-N 0.000 description 1
- 241000283977 Oryctolagus Species 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- NKLCHDQGUHMCGL-UHFFFAOYSA-N cyclohexylidenemethanone Chemical group O=C=C1CCCCC1 NKLCHDQGUHMCGL-UHFFFAOYSA-N 0.000 description 1
- 125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 150000002337 glycosamines Chemical class 0.000 description 1
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000001402 nonanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59215683A JPS6193117A (ja) | 1984-10-15 | 1984-10-15 | 副作用の軽減されたペネム型またはカルバペネム型抗生物質製剤 |
| IE252285A IE59395B1 (en) | 1984-10-15 | 1985-10-14 | Composition containing a penem or carbapenem antibiotic |
| DK469385A DK165665C (da) | 1984-10-15 | 1985-10-14 | Laegemiddel indeholdende et penem- eller carbapenemantibiotikum og et aminosyrederviat |
| NO854056A NO172099C (no) | 1984-10-15 | 1985-10-14 | Fremgangsmaate til fremstilling av et preparat som inneholder et penem -eller karbapenemantibiotikum og en n-acetylert aminosyre |
| NZ213829A NZ213829A (en) | 1984-10-15 | 1985-10-15 | Antibiotic compositions containing a penem or carbapenem plus certain n-acylated amino acids |
| DE8585307427T DE3585262D1 (de) | 1984-10-15 | 1985-10-15 | Zusammensetzung mit gehalt an einem penem- oder carbapenemantibiotikum. |
| EP85307427A EP0178911B1 (en) | 1984-10-15 | 1985-10-15 | Composition containing a penem or carbapenem antibiotic |
| AT85307427T ATE71836T1 (de) | 1984-10-15 | 1985-10-15 | Zusammensetzung mit gehalt an einem penem- oder carbapenemantibiotikum. |
| HU853994A HU200922B (en) | 1984-10-15 | 1985-10-15 | Process for producing pharmaceutical compositions comprising penem or carbapenem antibiotic |
| CA000493012A CA1268708A (en) | 1984-10-15 | 1985-10-15 | Composition containing a penem or carbapenem antibiotic and a method of using the same |
| FI854014A FI854014L (fi) | 1984-10-15 | 1985-10-15 | Antibiotik sammansaettning innehaollande penem eller karbapenem och foerfarande foer anvaendning av desamma. |
| ZA857886A ZA857886B (en) | 1984-10-15 | 1985-10-15 | Composition containing a penem or carbapenem antibiotic and a method of using the same |
| KR1019850007574A KR910009050B1 (ko) | 1984-10-15 | 1985-10-15 | 페넴 또는 카르바페넴 항생물질과 아미노산 유도체와의 조성물의 제조방법 |
| AU48730/85A AU589377B2 (en) | 1984-10-15 | 1985-10-15 | Composition containing a penem or carbapenem antibiotic and a method of using the same |
| ES547896A ES8703476A1 (es) | 1984-10-15 | 1985-10-15 | Un procedimiento para la preparacion de una composicion de un antibioticos de peben y un aminoacido n-acilado. |
| US06/917,793 US4757066A (en) | 1984-10-15 | 1986-10-10 | Composition containing a penem or carbapenem antibiotic and the use of the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59215683A JPS6193117A (ja) | 1984-10-15 | 1984-10-15 | 副作用の軽減されたペネム型またはカルバペネム型抗生物質製剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6193117A JPS6193117A (ja) | 1986-05-12 |
| JPH0461849B2 true JPH0461849B2 (ko) | 1992-10-02 |
Family
ID=16676427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59215683A Granted JPS6193117A (ja) | 1984-10-15 | 1984-10-15 | 副作用の軽減されたペネム型またはカルバペネム型抗生物質製剤 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS6193117A (ko) |
| ZA (1) | ZA857886B (ko) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63290860A (ja) * | 1987-05-22 | 1988-11-28 | Sanraku Inc | アミノエチルシステイン誘導体 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS505520A (ko) * | 1973-05-17 | 1975-01-21 |
-
1984
- 1984-10-15 JP JP59215683A patent/JPS6193117A/ja active Granted
-
1985
- 1985-10-15 ZA ZA857886A patent/ZA857886B/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS505520A (ko) * | 1973-05-17 | 1975-01-21 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6193117A (ja) | 1986-05-12 |
| ZA857886B (en) | 1987-06-24 |
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