US2043650A - Aqueous solutions of addition com - Google Patents
Aqueous solutions of addition com Download PDFInfo
- Publication number
- US2043650A US2043650A US2043650DA US2043650A US 2043650 A US2043650 A US 2043650A US 2043650D A US2043650D A US 2043650DA US 2043650 A US2043650 A US 2043650A
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- US
- United States
- Prior art keywords
- water
- salts
- acid
- soluble
- aqueous solutions
- 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
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- 239000007864 aqueous solution Substances 0.000 title description 18
- 239000011780 sodium chloride Substances 0.000 description 62
- 150000003839 salts Chemical class 0.000 description 60
- 229910001385 heavy metal Inorganic materials 0.000 description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- DZBUGLKDJFMEHC-UHFFFAOYSA-O acridine;hydron Chemical class C1=CC=CC2=CC3=CC=CC=C3[NH+]=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-O 0.000 description 22
- 238000000034 method Methods 0.000 description 22
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 20
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- LMEWRZSPCQHBOB-UHFFFAOYSA-M silver;2-hydroxypropanoate Chemical compound [Ag+].CC(O)C([O-])=O LMEWRZSPCQHBOB-UHFFFAOYSA-M 0.000 description 12
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 10
- 150000001735 carboxylic acids Chemical class 0.000 description 10
- 230000001225 therapeutic Effects 0.000 description 10
- VXGOQVMIGNMUGC-UHFFFAOYSA-O 1-methylacridin-10-ium Chemical compound C1=CC=C2C=C3C(C)=CC=CC3=[NH+]C2=C1 VXGOQVMIGNMUGC-UHFFFAOYSA-O 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 8
- 239000004310 lactic acid Substances 0.000 description 8
- 235000014655 lactic acid Nutrition 0.000 description 8
- 230000000737 periodic Effects 0.000 description 8
- OPQARKPSCNTWTJ-UHFFFAOYSA-L Copper(II) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 150000003378 silver Chemical class 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butanoic acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 4
- AAWZDTNXLSGCEK-WYWMIBKRSA-N Quinic acid Chemical class O[C@@H]1C[C@](O)(C(O)=O)C[C@@H](O)[C@H]1O AAWZDTNXLSGCEK-WYWMIBKRSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- -1 for instance Chemical class 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-K 2qpq Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- SCJNCDSAIRBRIA-DOFZRALJSA-N Arachidonyl-2'-chloroethylamide Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCCl SCJNCDSAIRBRIA-DOFZRALJSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- SVBVQSOWIBYSDK-UHFFFAOYSA-N C(C)(=O)[O-].NC=1C=C(C2=CC3=CC=C(C=C3[NH+]=C2C1)N)C Chemical compound C(C)(=O)[O-].NC=1C=C(C2=CC3=CC=C(C=C3[NH+]=C2C1)N)C SVBVQSOWIBYSDK-UHFFFAOYSA-N 0.000 description 2
- GUWSLQUAAYEZAF-UHFFFAOYSA-L Lead(II) acetate Chemical compound O1C(C)=O[Pb]21O=C(C)O2 GUWSLQUAAYEZAF-UHFFFAOYSA-L 0.000 description 2
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L Mercury(II) acetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 2
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N O-Toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N P-Toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 2
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M Silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 2
- KCWWJBVKSFUTJO-UHFFFAOYSA-L [Pb+2].CC([O-])=O.CC(O)C([O-])=O Chemical compound [Pb+2].CC([O-])=O.CC(O)C([O-])=O KCWWJBVKSFUTJO-UHFFFAOYSA-L 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- YPQQCGIIMOFILY-UHFFFAOYSA-N acridine;2-hydroxypropanoic acid Chemical compound CC(O)C(O)=O.C1=CC=CC2=CC3=CC=CC=C3N=C21 YPQQCGIIMOFILY-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-M aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 229940027985 antiseptics and disinfectants Silver compounds Drugs 0.000 description 2
- NGBNXJUWQPLNGM-UHFFFAOYSA-O azanium;silver Chemical class [NH4+].[Ag+] NGBNXJUWQPLNGM-UHFFFAOYSA-O 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000001734 carboxylic acid salts Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000003841 chloride salts Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- DYROSKSLMAPFBZ-UHFFFAOYSA-L copper;2-hydroxypropanoate Chemical compound [Cu+2].CC(O)C([O-])=O.CC(O)C([O-])=O DYROSKSLMAPFBZ-UHFFFAOYSA-L 0.000 description 2
- 229940076286 cupric acetate Drugs 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000174 gluconic acid Substances 0.000 description 2
- 229950006191 gluconic acid Drugs 0.000 description 2
- 235000012208 gluconic acid Nutrition 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-M glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- PVFSDGKDKFSOTB-UHFFFAOYSA-K iron(3+);triacetate Chemical compound [Fe+3].CC([O-])=O.CC([O-])=O.CC([O-])=O PVFSDGKDKFSOTB-UHFFFAOYSA-K 0.000 description 2
- 229940046892 lead acetate Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229940071536 silver acetate Drugs 0.000 description 2
- 150000003379 silver compounds Chemical class 0.000 description 2
- 229940100890 silver compounds Drugs 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 229960001367 tartaric acid Drugs 0.000 description 2
- 230000001131 transforming Effects 0.000 description 2
Classifications
-
- 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
- A61K31/555—Heterocyclic compounds containing heavy metals, e.g. hemin, hematin, melarsoprol
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic System
- C07F1/10—Silver compounds
Definitions
- aqueous solutions of valuable complex heavy metal addition compounds of acridinium bases are obtained by mixing with heavy metal salts the water-soluble salts of acridinium bases obtainable, for instance, according to the above named application.
- This process allows the combined pharmaceutical application of quaternary ammonium salts with heavy metal salts, for instance, silver salts.
- the chlorides and sulfates of the quaternary ammonium bases cannot be applied simultaneously with silver salts on account of the formation of insoluble silver salts, complex silver compounds of the ammonium salts may readily be obtained with the aid of the bicarbonates.
- the bicarbonates are dissolved in an organic acid, such as lactic acid, and when the evolution of carbon dioxide gas has ceased silver lactate is added, completely stable solutions of the silver ammonium salts being thus obtained.
- Carboxylic acids in which the bicarbonates may be dissolved are, for instance, formic acid, acetic acid, propionic acid, butyric acid, lactic acid, tartaric acid, benzoic acid, ortho-toluic acid, meta-toluio acid, para-toluic acid, glycollic acid, citric acid, gluconic acid, and quinic acid.
- saltsof the above named acids with copper, silver, gold, iron, mercury, lead, particularly those of the first group of the periodic system, for instance, silver lactate, silver acetate, cupric acetate, lead acetate, mercuric acetate and ferric acetate.
Description
Patented June 9, 1936 UNITED STATES PATENT OFFICE 2,043,650 AQUEOUS SOLUTIONS OF ADDIT ON oOM- POUNDS OF ALKYLACRIDINIUM SALTS WITH HEAVY METAL SALTS AND A PROC- ESS F PREPARING THEM No Drawing.
Application March 28, 1935, Serial No. 13,580. In Germany May 26, 1932 13 Claims. (Cl. 260-11) v for instance, been described in our co-pending The present invention relates to aqueous solutions of addition compounds of alkylacridinium salts with heavy metal salts and to a process of preparing them.
In our co-pending application Serial No. 13,579 filed March 28, 1935 there is described a process for preparing salts of acridinium bases by transforming salts of the ammonium bases into the bicarbonates and then dissolving the latter in any acids.
Now we have found that aqueous solutions of valuable complex heavy metal addition compounds of acridinium bases are obtained by mixing with heavy metal salts the water-soluble salts of acridinium bases obtainable, for instance, according to the above named application. This process allows the combined pharmaceutical application of quaternary ammonium salts with heavy metal salts, for instance, silver salts. Whereas, as is known, the chlorides and sulfates of the quaternary ammonium bases cannot be applied simultaneously with silver salts on account of the formation of insoluble silver salts, complex silver compounds of the ammonium salts may readily be obtained with the aid of the bicarbonates. In this case the bicarbonates are dissolved in an organic acid, such as lactic acid, and when the evolution of carbon dioxide gas has ceased silver lactate is added, completely stable solutions of the silver ammonium salts being thus obtained.
The following table shows the results of tests regarding the solubilities of some of the acridinium salts obtainable by Way of the bicarbonates, and of their heavy metal compounds; the limit of solubility was not attained in these tests:
3,6-diamino--methylacridinium acetate 3,6-diamin0-l0-methylacridinium glycolate--. 3,6-diamino-IO-methylacridinium aminoacetat 3,6diaminO-IO-methyIacridinium citrate The quinic acid salt of 3,6-diamino-l0-methylacr ium base- 3,6-diamino l0-methylacridinium-alpl1a-hydroxyphenylacetate 3,fi-diamino-lO-acridinium lactate 3,ii-iiamino-lO-methylacridinium lactate copper acea e- 3,6-diamino-lO-methylacridinium lactate lead acetate at least 1:10
3,G-diamino-lO-methylacridinium acetate copper acetate application above referred to. Carboxylic acids, in which the bicarbonates may be dissolved are, for instance, formic acid, acetic acid, propionic acid, butyric acid, lactic acid, tartaric acid, benzoic acid, ortho-toluic acid, meta-toluio acid, para-toluic acid, glycollic acid, citric acid, gluconic acid, and quinic acid. As heavy metal salts there may be'used the saltsof the above named acids with copper, silver, gold, iron, mercury, lead, particularly those of the first group of the periodic system, for instance, silver lactate, silver acetate, cupric acetate, lead acetate, mercuric acetate and ferric acetate.
The following example serves to illustrate the invention, but it is not intended to limit it thereto 2.2 grams of the bicarbonate of 3.6-diamino-10- methylacridinium hydroxide prepared, for instance, according to Example 1 of our co-pending application above referred to, are mixed with 0.9 gram of lactic acid of 90 per cent strength; the whole is made up to 200 cc. after addition of 1.5 grams of silver lactate. The solution is stable. If desired, buffer substances may be added or the solution may be adjusted to neutral reaction.
We claim:
1. The process which comprises dissolving the bicarbonate of an acridinium base substituted at the nitrogen by an alkyl radical of the lower series in a carboxylic acid forming a water-soluble salt with said base and causing a water-soluble heavy metal salt of carboxylic acid to act in the presence of water upon the water-soluble alkylacridinium salt thus obtained.
2. The process which comprises dissolving the bicarbonate of an acridinium base substituted at the nitrogen by an alkyl radical of the lower series in a lower aliphatic carboxylic acid forming a water-soluble salt with said base and causing a water-soluble heavy metal salt of carboxylic acid to act in the presence of water upon the water-soluble alkylacridinium salt thus obtained.
3. The process which comprises dissolving the bicarbonate of a methylacridinium base in a lower aliphatic carboXylic acid forming a watersoluble salt with said base and causing a watersoluble salt of a heavy metal from the first group of the periodic system and a carboxylic acid to act in the presence of water upon the watersoluble methylacridinium salt thus obtained.
4. The process which comprises dissolving 3.6- diamino-l0-methylacridinium bicarbonate in lactic acid and causing silver lactate to act in the presence of water upon the acridinium lactate thus obtained.
5. The process which comprises causing a water-soluble salt or" an acridinium base substituted at the nitrogen by an alkyl radical of the lower series with a carboxylic acid to act upon a water-soluble heavy metal salt of a carboxylic acid in the presence of water.
6; The process which comprises causing a water-soluble salt of an acridinium base substituted at the nitrogen by an alkyl radical of the lower series with a lower aliphatic carboxylic acid to act upon a water-soluble heavy metal salt of a carboxylic acid in the presence of water.
7. The process which comprises causing a water-soluble salt of a methylacridinium base with a lower aliphatic carboxylic acid to act in the presence of water upon a water-soluble salt of a heavy metal from the first group of the periodic system and a carboxylic acid.
8. The process which comprises causing the lactate of 3,6-diarm'no-IO-methylacridinium hydroxide to act upon silver lactate in the presence of water.
9. Aqueous solutions of complex addition compounds of water-soluble salts of acridinium bases substituted at the nitrogen by an alkyl radical of the lower series with water-soluble salts of heavy metals of carboxylic acids, said solutions showing valuable therapeutic properties.
10. Aqueous solutions of complex addition compounds of water-soluble carboxylic acid salts of acridinium bases substituted at the nitrogen by an alkyl radical of the lower series with watersoluble salts of heavy metals of carboxylic acids, said solutions showing valuable therapeutic properties.
11. Aqueous solutions of complex addition compounds of water-soluble lower aliphatic oarboxylic acid salts of acridinium bases substituted at the nitrogen by an alkyl radical of the lower series with water-soluble salts of heavy metals of carboXylic acids, said solutions showing valuable therapeutic properties.
12. Aqueous solutions of complex addition compounds of Water-soluble lower aliphatic carboxylic acid salts of methyl-acridinium bases with water-soluble salts of heavy metals from the first group of the periodic system and carboxylic acids, said solutions showing valuable therapeutic properties.
13. Aqueous solutions of the complex addition compounds of 3.6-diamino-IO-methylacridinium lactate with silver lactate, said solutions showing valuable therapeutic properties.
MAX BocKMiiHL. LEONHARD STEIN.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2043650A true US2043650A (en) | 1936-06-09 |
Family
ID=3427945
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2043650D Expired - Lifetime US2043650A (en) | Aqueous solutions of addition com |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2043650A (en) |
-
0
- US US2043650D patent/US2043650A/en not_active Expired - Lifetime
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