ES477167A1 - Derivatives of (-)-cis-1,2- Epoxypropylphosphonic Acid, Their Preparation, and Pharmaceutical Compositions Containing Them - Google Patents
Derivatives of (-)-cis-1,2- Epoxypropylphosphonic Acid, Their Preparation, and Pharmaceutical Compositions Containing ThemInfo
- Publication number
- ES477167A1 ES477167A1 ES477167A ES477167A ES477167A1 ES 477167 A1 ES477167 A1 ES 477167A1 ES 477167 A ES477167 A ES 477167A ES 477167 A ES477167 A ES 477167A ES 477167 A1 ES477167 A1 ES 477167A1
- Authority
- ES
- Spain
- Prior art keywords
- cis
- derivatives
- pharmaceutical compositions
- epoxypropylphosphonic acid
- preparation
- 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
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 2
- 235000001014 amino acid Nutrition 0.000 abstract 2
- 150000001413 amino acids Chemical class 0.000 abstract 2
- 235000019441 ethanol Nutrition 0.000 abstract 2
- YMDXZJFXQJVXBF-STHAYSLISA-N fosfomycin Chemical compound C[C@@H]1O[C@@H]1P(O)(O)=O YMDXZJFXQJVXBF-STHAYSLISA-N 0.000 abstract 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract 2
- PHIQHXFUZVPYII-ZCFIWIBFSA-O (R)-carnitinium Chemical compound C[N+](C)(C)C[C@H](O)CC(O)=O PHIQHXFUZVPYII-ZCFIWIBFSA-O 0.000 abstract 1
- 239000004475 Arginine Substances 0.000 abstract 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 abstract 1
- LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 abstract 1
- 239000004471 Glycine Substances 0.000 abstract 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 abstract 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 abstract 1
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 abstract 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 abstract 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 abstract 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004472 Lysine Substances 0.000 abstract 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 abstract 1
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 abstract 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 abstract 1
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 abstract 1
- 229960003121 arginine Drugs 0.000 abstract 1
- 229960003237 betaine Drugs 0.000 abstract 1
- 229960004203 carnitine Drugs 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 230000000973 chemotherapeutic effect Effects 0.000 abstract 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 abstract 1
- 229960001231 choline Drugs 0.000 abstract 1
- 229960002173 citrulline Drugs 0.000 abstract 1
- 235000013477 citrulline Nutrition 0.000 abstract 1
- 229960003067 cystine Drugs 0.000 abstract 1
- 229960000308 fosfomycin Drugs 0.000 abstract 1
- 229960002449 glycine Drugs 0.000 abstract 1
- 229960003646 lysine Drugs 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 1
- 229930182817 methionine Natural products 0.000 abstract 1
- 229960004452 methionine Drugs 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229960003104 ornithine Drugs 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65502—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a three-membered ring
- C07F9/65505—Phosphonic acids containing oxirane groups; esters thereof
-
- 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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Derivatives of (-)-cis-1,2- epoxypropylphosphonic acid ("phosphonomycin" or "Fosfomycin") having antibacterial chemotherapeutic properties and of use in human therapy, e.g. as pharmaceutical compositions, are of the general formula: < IMAGE > in which A'<+> is cation of an aminoacid, as for example lysine, arginine, ornithine, cystine, methionine, glycine, citrulline, etc., or of a naturally occurring trimethylammonium derivative, as for example choline, carnitine, betaine, etc., and can be prepared by reaction between substantially equimolecular quantities of (-)-cis-1,2-epoxypropylphosphonic acid and the aminoacid or of trimethylammonium derivative, preferably in an aqueous solution, or in a mixture of water and an alcohol such as methyl or ethyl alcohol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT41002/78A IT1161974B (en) | 1978-02-02 | 1978-02-02 | CIS.I 2 EPOXYPROPYLPHOSPHONIC ACID DERIVATIVES THEIR PREPARATION PROCEDURE AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES477167A1 true ES477167A1 (en) | 1979-12-01 |
Family
ID=11249990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES477167A Expired ES477167A1 (en) | 1978-02-02 | 1979-01-25 | Derivatives of (-)-cis-1,2- Epoxypropylphosphonic Acid, Their Preparation, and Pharmaceutical Compositions Containing Them |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS54109922A (en) |
| BE (1) | BE873696A (en) |
| DE (1) | DE2820794C2 (en) |
| DK (1) | DK22279A (en) |
| ES (1) | ES477167A1 (en) |
| FR (1) | FR2416013A1 (en) |
| GB (1) | GB2013682A (en) |
| IT (1) | IT1161974B (en) |
| LU (1) | LU80864A1 (en) |
| NL (1) | NL7900608A (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2158828B (en) * | 1984-04-25 | 1987-12-09 | Espanola De La Penicilina Y An | Salts of fosfomycin |
| CH660306A5 (en) * | 1984-10-05 | 1987-04-15 | Schering Spa | WATER-SOLUBLE PHARMACEUTICAL COMPOSITIONS BASED ON SALTS OF (-)CIS-1,2-EPOXYPROPYLPHOSPHONIC ACID WITH AMINO ACIDS. |
| CH660305A5 (en) * | 1984-10-05 | 1987-04-15 | Schering Spa | WATER-SOLUBLE PHARMACEUTICAL COMPOSITIONS BASED ON SALTS OF (-)CIS-1,2-EPOXYPROPYLPHOSPHONIC ACID WITH AMINO ACIDS. |
| IT1244543B (en) * | 1991-02-01 | 1994-07-15 | La Fa Re Srl | TOPICAL USE OF PHOSPHOMYCIN AND ITS SALTS IN THE TREATMENT OF VAGINAL AND / OR URETHRAL INFECTIONS |
| EP1033133A4 (en) * | 1997-10-03 | 2004-09-01 | Meiji Seika Kaisha | Composition for treatment of diabetes and treatment of diabetes |
| ITMI20021725A1 (en) * | 2002-08-01 | 2002-10-31 | Zambon Spa | PHARMACEUTICAL COMPOSITIONS WITH ANTIBIOTIC ACTIVITY. |
| CN102579466A (en) * | 2011-01-10 | 2012-07-18 | 王乐 | Composition of fosfomycin or fosfomycin arginine salt and arginine |
| EP3812007A1 (en) | 2019-10-24 | 2021-04-28 | Sandoz Ag | New formulations of fosfomycin with reduced sodium content for parenteral use and methods of producing the same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6814979A (en) * | 1967-10-30 | 1969-05-02 |
-
1978
- 1978-02-02 IT IT41002/78A patent/IT1161974B/en active
- 1978-05-12 DE DE2820794A patent/DE2820794C2/en not_active Expired
-
1979
- 1979-01-18 DK DK22279A patent/DK22279A/en unknown
- 1979-01-25 BE BE2057565A patent/BE873696A/en not_active IP Right Cessation
- 1979-01-25 NL NL7900608A patent/NL7900608A/en not_active Application Discontinuation
- 1979-01-25 ES ES477167A patent/ES477167A1/en not_active Expired
- 1979-01-26 JP JP866779A patent/JPS54109922A/en active Pending
- 1979-01-29 FR FR7902181A patent/FR2416013A1/en active Pending
- 1979-02-01 LU LU80864A patent/LU80864A1/en unknown
- 1979-02-02 GB GB7903684A patent/GB2013682A/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| NL7900608A (en) | 1979-08-06 |
| GB2013682A (en) | 1979-08-15 |
| FR2416013A1 (en) | 1979-08-31 |
| JPS54109922A (en) | 1979-08-29 |
| BE873696A (en) | 1979-05-16 |
| IT7841002A0 (en) | 1978-02-02 |
| DE2820794B1 (en) | 1979-05-23 |
| DK22279A (en) | 1979-08-03 |
| DE2820794C2 (en) | 1980-01-17 |
| LU80864A1 (en) | 1979-06-07 |
| IT1161974B (en) | 1987-03-18 |
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