CA1146543A - Cefadroxil salts with amino acids - Google Patents
Cefadroxil salts with amino acidsInfo
- Publication number
- CA1146543A CA1146543A CA000372782A CA372782A CA1146543A CA 1146543 A CA1146543 A CA 1146543A CA 000372782 A CA000372782 A CA 000372782A CA 372782 A CA372782 A CA 372782A CA 1146543 A CA1146543 A CA 1146543A
- Authority
- CA
- Canada
- Prior art keywords
- cefadroxil
- salt
- arginine
- formula
- lysine
- 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
Links
- NBFNMSULHIODTC-CYJZLJNKSA-N cefadroxil monohydrate Chemical class O.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=C(O)C=C1 NBFNMSULHIODTC-CYJZLJNKSA-N 0.000 title claims abstract description 39
- 150000001413 amino acids Chemical class 0.000 title claims abstract description 8
- 229960004841 cefadroxil Drugs 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 238000004108 freeze drying Methods 0.000 claims abstract description 10
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 claims abstract description 8
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims abstract description 8
- 229930064664 L-arginine Natural products 0.000 claims abstract description 8
- 235000014852 L-arginine Nutrition 0.000 claims abstract description 8
- 229960004308 acetylcysteine Drugs 0.000 claims abstract description 8
- 235000001014 amino acid Nutrition 0.000 claims abstract description 7
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 claims abstract description 7
- 239000007900 aqueous suspension Substances 0.000 claims abstract description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
- 239000012453 solvate Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 5
- PEWXENMTDDNSMK-BYPYZUCNSA-N acetyl (2r)-2-amino-3-sulfanylpropanoate Chemical compound CC(=O)OC(=O)[C@@H](N)CS PEWXENMTDDNSMK-BYPYZUCNSA-N 0.000 claims description 4
- KDXKERNSBIXSRK-UHFFFAOYSA-M lysinate Chemical compound NCCCCC(N)C([O-])=O KDXKERNSBIXSRK-UHFFFAOYSA-M 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims 3
- -1 cefadroxil arginine salt Chemical class 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 abstract description 5
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 229910001868 water Inorganic materials 0.000 description 6
- 230000003115 biocidal effect Effects 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229960001065 cefadroxil monohydrate Drugs 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000002906 microbiologic effect Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 150000001483 arginine derivatives Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3
-
- 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)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21098A/80 | 1980-04-01 | ||
| IT21098/80A IT1148778B (it) | 1980-04-01 | 1980-04-01 | Sali cefadrovixil con aminoacidi |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1146543A true CA1146543A (en) | 1983-05-17 |
Family
ID=11176702
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000372782A Expired CA1146543A (en) | 1980-04-01 | 1981-03-11 | Cefadroxil salts with amino acids |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS56140996A (enExample) |
| CA (1) | CA1146543A (enExample) |
| CH (1) | CH651048A5 (enExample) |
| DE (1) | DE3112168A1 (enExample) |
| FR (1) | FR2479226A1 (enExample) |
| GB (1) | GB2073192B (enExample) |
| IL (1) | IL62377A (enExample) |
| IT (1) | IT1148778B (enExample) |
| NL (1) | NL8101272A (enExample) |
| YU (1) | YU84681A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351885B (zh) * | 2011-08-19 | 2012-08-22 | 深圳立健药业有限公司 | 用于制备头孢呋辛-l-精氨酸水合物的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3985741A (en) * | 1972-09-15 | 1976-10-12 | Bristol-Myers Company | Production of p-hydroxycephalexin |
| ES412429A1 (es) * | 1973-03-08 | 1976-01-01 | Gallardo Antonio Sa | Un procedimiento para la obtencion de sales de antibioticoscon aminoacidos de naturaleza basica. |
| JPS5089517A (enExample) * | 1973-12-18 | 1975-07-18 | ||
| JPS557434A (en) * | 1978-06-30 | 1980-01-19 | Matsushita Electric Works Ltd | Preparation of woody cement board |
| ES472186A1 (es) * | 1978-07-28 | 1979-02-16 | Liofilizaciones Esterilizacion | Procedimiento para la obtencion de sales del acido 7-(d-(-) a-amino a-(4-hidroxifenil) acetamido)-3-metil-3-cefem-4-car-boxilico con aminoacidos |
-
1980
- 1980-04-01 IT IT21098/80A patent/IT1148778B/it active
-
1981
- 1981-03-11 CA CA000372782A patent/CA1146543A/en not_active Expired
- 1981-03-13 CH CH1733/81A patent/CH651048A5/it not_active IP Right Cessation
- 1981-03-16 NL NL8101272A patent/NL8101272A/nl not_active Application Discontinuation
- 1981-03-16 IL IL62377A patent/IL62377A/xx unknown
- 1981-03-16 JP JP3666881A patent/JPS56140996A/ja active Granted
- 1981-03-25 FR FR8106000A patent/FR2479226A1/fr active Granted
- 1981-03-27 DE DE19813112168 patent/DE3112168A1/de not_active Withdrawn
- 1981-03-31 YU YU00846/81A patent/YU84681A/xx unknown
- 1981-03-31 GB GB8109981A patent/GB2073192B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| YU84681A (en) | 1983-10-31 |
| GB2073192B (en) | 1983-12-07 |
| IL62377A (en) | 1984-10-31 |
| JPS56140996A (en) | 1981-11-04 |
| JPH0161115B2 (enExample) | 1989-12-27 |
| IL62377A0 (en) | 1981-05-20 |
| CH651048A5 (it) | 1985-08-30 |
| FR2479226A1 (fr) | 1981-10-02 |
| FR2479226B1 (enExample) | 1984-11-02 |
| IT1148778B (it) | 1986-12-03 |
| NL8101272A (nl) | 1981-11-02 |
| DE3112168A1 (de) | 1982-01-14 |
| IT8021098A0 (it) | 1980-04-01 |
| GB2073192A (en) | 1981-10-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |