GB2026492A - A process for the preparation of aminoacid salts of (-)-cis-1,2- epoxypropylphosphonic acid - Google Patents
A process for the preparation of aminoacid salts of (-)-cis-1,2- epoxypropylphosphonic acid Download PDFInfo
- Publication number
- GB2026492A GB2026492A GB7924643A GB7924643A GB2026492A GB 2026492 A GB2026492 A GB 2026492A GB 7924643 A GB7924643 A GB 7924643A GB 7924643 A GB7924643 A GB 7924643A GB 2026492 A GB2026492 A GB 2026492A
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- GB
- United Kingdom
- Prior art keywords
- aminoacid
- cis
- process according
- 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.)
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- 235000001014 amino acid Nutrition 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 18
- -1 aminoacid salts Chemical class 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- XWCIXXXLOAAWPU-IHWYPQMZSA-N [(z)-prop-1-enyl]phosphonic acid Chemical compound C\C=C/P(O)(O)=O XWCIXXXLOAAWPU-IHWYPQMZSA-N 0.000 claims abstract description 8
- 238000006735 epoxidation reaction Methods 0.000 claims abstract description 6
- 150000001413 amino acids Chemical class 0.000 claims description 14
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 7
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 5
- 229910020341 Na2WO4.2H2O Inorganic materials 0.000 claims description 5
- WPZFLQRLSGVIAA-UHFFFAOYSA-N sodium tungstate dihydrate Chemical group O.O.[Na+].[Na+].[O-][W]([O-])(=O)=O WPZFLQRLSGVIAA-UHFFFAOYSA-N 0.000 claims description 5
- 239000004472 Lysine Substances 0.000 claims description 4
- 235000019766 L-Lysine Nutrition 0.000 claims description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 3
- 229930064664 L-arginine Natural products 0.000 claims description 3
- 235000014852 L-arginine Nutrition 0.000 claims description 3
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 229960003104 ornithine Drugs 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GGTYBZJRPHEQDG-WCCKRBBISA-N (2s)-2,5-diaminopentanoic acid hydrochloride Chemical compound Cl.NCCC[C@H](N)C(O)=O GGTYBZJRPHEQDG-WCCKRBBISA-N 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 235000009697 arginine Nutrition 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 235000018977 lysine Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A process for the preparation of aminoacid salts of (-)-cis-1,2- epoxypropylphosphonic acid comprises the epoxidation of the corresponding salt of cis-propenylphosphonic acid. Where diastereoisomeric salts are obtained they can be resolved.
Description
SPECIFICATION
A process for the preparation of aminoacid salts of (-)-cis-1,2-Epoxypropylphosphonic acid
The present invention relates to a new process for the preparation of aminoacid salts of (-)-cis-1,2epoxypropylphosphonic acid.
The salts forming the object of the invention are of the general formula
in which A is an aminoacid, and more particularly a natural aminoacid such as lysine, arginine, ornithine, cysteine, etc.
In our British Application No. 7903684 of February 2, 1979 a process is described for the preparation of the compounds (I) and related compounds, the process comprising the reaction of substantially equimolecular quantities of (-)-cls-1,2-epoxypropylphosphonic acid and of the aminoacid, in aqueous or aqueous/alcoholic acid.
It has now been found that the salts of formula (I) can be obtained with on the whole better yields (calculated on the (-)-cls-1,2-epoxypropylphosphonic acid), and with a better purity, by subjecting to an epoxidation the corresponding salt of (cis-propenylphosphonic acid (II) with the appropriate aminoacid, following the reaction scheme:
CH3 /POSH poxidntion (I) H /C=C .AH+ H \H in which A has the above-indicated meaning.
In particular, when A represents an optically active aminoacid, the epoxidation leads to a mixture of diastereoisomeric salts, which can be separated by fractional crystallization or other resolution procedure.
The epoxidation can be performed by per se known methods, as for instance with peroxyacids (particularly with peroxybenzoic,m-chloroperbenzoic or monoperphthalic acid), or with H2O2, suitably in the presence of alkali metal tungstates e.g. Na2WO4.2H2O.
Illustrative Examples are given below of the process of the present invention.
EXAMPLE 1
L-arginine (-)-cis-epoxypropylphosphonate 13.3g (0.1 mol) of cis-propenylphosphonic acid (bromometric titre: 91%) was dissolved in 80 ml of isopropanol; 1 ig (0.06 mol) of L-arginine was added; and the mixture stirred for 60 minutes.
The pH of the mixture was adjusted from 5.6 to 5.7 with triethylamine, and then 0.5 g of Na2WO4.2H2O and 0.1 g of EDTA.Na2, dissolved in 1.5 ml of water, were added.
After heating of the resultant mixture to 48-50"C, 1 6.3 ml of H202 (30% v/v) was added drop by drop, the temperature being maintained at 50-55"C.
The mixture was stirred for 60 minutes, cooled, and the resultant solid residue (1 5g) recrystallized three times from ethanol-water (1: 1) to give the desired compound.
M.p. = 212-217 C (with decomposition)
Analysis for C9H2106N4P (MW 312)
%C %H %N %P
Theoretical 34.61 6.73 17.95 9.93
Found 34.33 7.00 17.71 9.73 (a)365 = + 13.3 (C = 5% in H2O)
NMR-spectrum (in D20) 6:1.47 (CH3); 1.6-2 (CH2CH2); 2.85 (CH-P); 3-3.3 (CH, CH2NH); 3.7 (CH-NH2).
EXAMPLE2
L-lysine (-)-cis-epoxypropylphosphonate
13.3 g (0.1 mol) of cis-propenylphosphonic acid (bromometric titre: 91%) was dissolved in 80 ml of isopropanol; 0.1 mol (29 g, 50% in H2O) of L-lysine was added, and the mixture stirred for 60 minutes; thereafter 0.5 g of Na2WO4.2H2O and 0.1 g of EDTA.Na2 in 1.5 ml of H2O were added.
To the mixture, heated to 48-500C, was added 16.3 ml of H202 (30% v/v) drop by drop, the temperature being regulated at 50-55 C by a water bath. Stirring for 60 minutes, cooling and addition of 150 ml of absolute ethanol gave a gummy product which was separated by decantation and treated with absolute ethanol.
17 g of a solid, the desired compound, was obtained, m.p. = 170-72 C (decomposition).
The product was recrystallized three times from methanol.
M.p. = 1650C (decomposition)
Analysis: for CgH21N206P (MW 284)
%C %H %N %P
Theoretical 38.03 7.39 9.86 10.91
Found 38.18 7.43 9.81 10.96 (a)365 = + 9.32 (C = A% in H2O)
NMR-spectrum (in 1)20) b: 1.4-2.1 (CH3, (CH2)3); 2.8 (CH-P); 3.3 (CH)- 3.7 (CHNH2); 2.9-3.2 (CH2NH2).
EXAMPLE3
L-ornithine (-)-cis-epoxypropylphosphonate
6.7 g (0.05 mol) of cis-propenylphosphonic acid (bromometric titre: 91%) was added to a mixture of 8.5 g (0.05 mol) of L-ornithine hydrochloride, 40 ml of ethanol (80%) and 29 (0.05 mols) of NaOH.
A solution of 0.25 g of Na2WO4.2H2O and 0.05 g of EDTA.Na2 in 1.5 ml of water was added.
The mixture was heated to 480C, then 8.2 ml of H202 (30% v/v) added, the temperature being maintained at 50-55 C by a water bath.
After stirring of the resultant mix for three hours, 150 ml of absolute ethanol was added, and a gummy residue separated by decantation and recrystallized 3 times from ethanol-water (2:1).
The desired product was obtained, melting at 191-193 C (with decomposition).
Analysis: for C8H19N206P (MW 270)
%C %H %N %P
Theoretical 35.56 7.04 10.37 11.48
Found 35.64 7.01 10.24 11.56 (a)3D5 = + 10.2 (C = 5% in H2O)
NMR-spectrum (in D2O) b: 1.48 (CH3); 1.7-2 (CH2-CH2); 2.8-3.3 (CH-P, CH2NH2); 3.45 (CH); 3.85 (CHNH2).
Claims (9)
1. A process for the preparation of an aminoacid salt of (-)-cis-1 ,2-epoxypropylphosphonic acid with the general formula (I)
in which A is an aminoacid, wherein the corresponding salt of cis-propenylphosphonic acid with the appropriate aminoacid (II) is subjected to epoxidation, in accordance with the reaction scheme:
CHO PQsH C C = C / AH+ epoxidntion H \H (wherein A is as defined).
2. A process according to Claim 1, in which the aminoacid is a natural aminoacid.
3. A process according to Claim 2, in which the aminoacid is L-arginine.
4. A process according to Claim 2, in which the aminoacid is L-lysine.
5. A process according to Claim 2, in which the aminoacid is L-ornithine.
6. A process according to any of Claims 1 to 5, in which the epoxidation is carried out with H202 in the presence of an alkali metal tungstate.
7. A process according to Claim 6, in which the tungstate is Na2WO4.2H2O.
8. A process according to Claims 2 to 7, in which diastereoisomeric salts are produced and are separated,
9. Salts of cis-propenylphosphonic acid with aminoacids, whenever obtained by a process according to any of Claims 1 to 8.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT26304/78A IT1097578B (en) | 1978-07-31 | 1978-07-31 | METHOD FOR PREPARING ACID SALTS (-) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2026492A true GB2026492A (en) | 1980-02-06 |
Family
ID=11219184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7924643A Withdrawn GB2026492A (en) | 1978-07-31 | 1979-07-16 | A process for the preparation of aminoacid salts of (-)-cis-1,2- epoxypropylphosphonic acid |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5562097A (en) |
| BE (1) | BE877644A (en) |
| DE (1) | DE2929953A1 (en) |
| DK (1) | DK291479A (en) |
| ES (1) | ES483027A1 (en) |
| FR (1) | FR2432523A1 (en) |
| GB (1) | GB2026492A (en) |
| IT (1) | IT1097578B (en) |
| LU (1) | LU81553A1 (en) |
| NL (1) | NL7905458A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2165152A (en) * | 1984-10-05 | 1986-04-09 | Seuref Ag | Hydrosoluble antibiotic pharmaceutical compositions |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3625982A (en) * | 1968-05-15 | 1971-12-07 | Merck & Co Inc | (1,2-epoxypropyl)phosphonous acid derivatives |
| JPS5414924A (en) * | 1977-07-01 | 1979-02-03 | Kanebo Ltd | Preparation of (-)-cis-1,2-epoxypropylphosphonic acid derivative |
-
1978
- 1978-07-31 IT IT26304/78A patent/IT1097578B/en active
-
1979
- 1979-07-11 DK DK291479A patent/DK291479A/en unknown
- 1979-07-12 BE BE2/57947A patent/BE877644A/en not_active IP Right Cessation
- 1979-07-12 NL NL7905458A patent/NL7905458A/en not_active Application Discontinuation
- 1979-07-16 GB GB7924643A patent/GB2026492A/en not_active Withdrawn
- 1979-07-18 FR FR7918632A patent/FR2432523A1/en active Pending
- 1979-07-24 DE DE19792929953 patent/DE2929953A1/en not_active Withdrawn
- 1979-07-25 JP JP9553779A patent/JPS5562097A/en active Pending
- 1979-07-27 LU LU81553A patent/LU81553A1/en unknown
- 1979-07-31 ES ES483027A patent/ES483027A1/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2165152A (en) * | 1984-10-05 | 1986-04-09 | Seuref Ag | Hydrosoluble antibiotic pharmaceutical compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| IT7826304A0 (en) | 1978-07-31 |
| ES483027A1 (en) | 1980-04-16 |
| FR2432523A1 (en) | 1980-02-29 |
| LU81553A1 (en) | 1979-10-31 |
| NL7905458A (en) | 1980-02-04 |
| JPS5562097A (en) | 1980-05-10 |
| IT1097578B (en) | 1985-08-31 |
| DE2929953A1 (en) | 1980-02-21 |
| BE877644A (en) | 1979-11-05 |
| DK291479A (en) | 1980-02-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |