DE272035C - - Google Patents
Info
- Publication number
- DE272035C DE272035C DENDAT272035D DE272035DA DE272035C DE 272035 C DE272035 C DE 272035C DE NDAT272035 D DENDAT272035 D DE NDAT272035D DE 272035D A DE272035D A DE 272035DA DE 272035 C DE272035 C DE 272035C
- Authority
- DE
- Germany
- Prior art keywords
- solution
- alcohol
- stand
- alkali
- parts
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 150000001495 arsenic compounds Chemical class 0.000 claims description 4
- 239000007859 condensation product Substances 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- -1 aldehyde sulfonic acids Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- AWYSLGMLVOSVIS-UHFFFAOYSA-N phenyl(phenylarsanylidene)arsane Chemical class C1=CC=CC=C1[As]=[As]C1=CC=CC=C1 AWYSLGMLVOSVIS-UHFFFAOYSA-N 0.000 claims description 2
- OHFDBBFDFZXHJQ-UHFFFAOYSA-N phenylarsane Chemical compound [AsH2]C1=CC=CC=C1 OHFDBBFDFZXHJQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 229940093920 gynecological arsenic compound Drugs 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 150000001447 alkali salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- ZLIAPAVPGRSMIB-UHFFFAOYSA-N aminooxyarsonic acid Chemical class NO[As](O)(O)=O ZLIAPAVPGRSMIB-UHFFFAOYSA-N 0.000 description 1
- VJWWIRSVNSXUAC-UHFFFAOYSA-N arsinic acid Chemical class O[AsH2]=O VJWWIRSVNSXUAC-UHFFFAOYSA-N 0.000 description 1
- NDXGGKDTNFVFGA-UHFFFAOYSA-N arsinous amide Chemical class [AsH2]N NDXGGKDTNFVFGA-UHFFFAOYSA-N 0.000 description 1
- URCJRDMSDWTSGZ-UHFFFAOYSA-N benzaldehyde;sodium Chemical compound [Na].O=CC1=CC=CC=C1 URCJRDMSDWTSGZ-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- QJQZEJFUIOWFMS-UHFFFAOYSA-N formaldehyde;sulfanediol Chemical compound O=C.OSO QJQZEJFUIOWFMS-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
- C07F9/74—Aromatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
Vi 272035-KLASSE 12 o. GRUPPE Vi 272035- CLASS 12 or GROUP
Dr. HEINRICH BART in BAD DÜRKHEIM.Dr. HEINRICH BART in BAD DÜRKHEIM.
Patentiert im Deutschen Reiche vom 14. Mai 1912 ab.Patented in the German Empire on May 14, 1912.
Es wurde gefunden, daß Aldehyde, welche mindestens eine Sulfogruppe an einem der Kohlenstoffatome des betreffenden Moleküls gebunden enthalten, mit in Wasser schwer löslichen Derivaten des Arsenobenzols und des Phenylarsins, welche außer Aminogruppen gegebenenfalls noch andere Substituenten, wie z. B. OH usw., enthalten, ganz allgemein sich zu Verbindungen vereinigen, welche z. B.It has been found that aldehydes which contain at least one sulfo group bonded to one of the carbon atoms of the molecule in question with derivatives of arsenobenzene and phenylarsine which are sparingly soluble in water and which, in addition to amino groups, may have other substituents such as. B. OH , etc., contain, very generally combine to form compounds which, for. B.
ίο in Form ihrer Alkalisalze in Wasser leicht löslich sind. Diese Kondensationsprodukte haben vor den nach den Patenten 245756 und 249726 herstellbaren Kondensationsprodukten des Aminoarsenobenzols mit Formaldehyd und Bisulfit bezugsweise Formaldehydsulfoxylat den Vorzug, daß sie gegen Luftoxydation viel widerstandsfähiger sind, wie sich beim Stehenlassen der wäßrigen Lösungen an der Luft alsbald erkennen läßt,ίο in the form of their alkali salts in water easily are soluble. These condensation products have prior to those according to patents 245756 and 249726 producible condensation products of aminoarsenobenzene with formaldehyde and Bisulphite and formaldehyde sulphoxylate have the advantage that they are resistant to air oxidation are much more resistant, as when the aqueous solutions are left to stand Air immediately reveals,
Von dem Verfahren des Patents 193542, welches die Kondensation von Aldehyden mit Aminoarsinsäuren betrifft, unterscheidet sich das vorliegende Verfahren dadurch, daß es sich hier um Kondensation von Aminoarsenobenzolen bezugsweise Aminoarsinen mit Aldehydsäuren handelt, zu dem Zwecke, sie neutral löslich zu machen, während die Arsinsäuren ja an sich bereits neutral lösliche Salze bilden.From the process of patent 193542 which allows the condensation of aldehydes with Concerning amino arsenic acids, the present process differs in that it This is about the condensation of aminoarsenobenzenes or aminoarsines with aldehyde acids acts, for the purpose of making them neutrally soluble, while the arsinic acids are already neutrally soluble salts form.
Zur Ausführung des Verfahrens läßt man beispielsweise ein oder mehrere Moleküle einer Aldehydsäure auf ein Molekül der betreffenden Arsenverbindung, zweckmäßig in alkalischer, neutraler oder nicht zu stark saurer Lösung einwirken. Man erhält auf diese 40 To carry out the process, one or more molecules of an aldehyde acid, for example, are allowed to act on a molecule of the arsenic compound in question, expediently in an alkaline, neutral or not too strongly acidic solution. You get 40
Weise therapeutisch wertvolle Verbindungen, die bei verhältnismäßig geringer Toxizität in Wasser mit neutraler Reaktion löslich sind.Way therapeutically valuable compounds that are relatively low in toxicity in Are soluble in water with a neutral reaction.
1. 2Teile4,4'-Dioxy-3,3'-diaminoarsenobenzol werden in eine Lösung von etwa 2 bis 5 Teilen Benzaldehydsulf osäure (erhalten aus Benzaldehyd und rauchender Schwefelsäure) in etwa 50 Teilen Wasser eingetragen. Nun wird mit so viel Alkalilauge (10 Prozent) oder Alkalicarbonat versetzt, bis vollständige Lösung, gegebenenfalls unter Erwärmen, eingetreten ist. Man läßt einige Zeit stehen. Sollte die Lösung alkalisch geworden sein, dann neutralisiert man mit einer Säure, z. B. Essigsäure. Die so erhaltene gut haltbare Lösung der Arsenverbindung kann direkt therapeutisch verwendet werden. Will man jedoch das Reduktionsprodukt in fester Form gewinnen, dann gießt man die oben erhaltene neutrale Lösung in etwa 200 Teile Alkohol, wobei die entsprechende neue Arsenverbindung als Alkalisalz in Form eines gelben Pulvers ausfällt. 1. 2 parts of 4,4'-dioxy-3,3'-diaminoarsenobenzene are in a solution of about 2 to 5 parts of benzaldehyde sulfonic acid (obtained from benzaldehyde and fuming sulfuric acid) in about 50 parts of water. Now is done with as much alkali (10 percent) or alkali carbonate added until complete solution, if necessary with heating, has occurred. One lets stand for some time. Should the Solution have become alkaline, then neutralized with an acid, e.g. B. acetic acid. The well-preserved solution of the arsenic compound obtained in this way can be used directly for therapeutic purposes be used. However, if one wants to obtain the reduction product in solid form, the neutral solution obtained above is then poured into about 200 parts of alcohol, the corresponding new arsenic compound precipitates as an alkali salt in the form of a yellow powder.
2. Verwendet man an Stelle des Dioxydiaminoarsenobenzols das entsprechende 4-Oxy-3-aminophenylarsin und verfährt im übrigen genau so wie oben beschrieben, so erhält man auch hier das entsprechende Kondensationsprodukt. 2. If the corresponding 4-oxy-3-aminophenylarsine is used instead of the dioxydiaminoarsenobenzene and if the rest of the procedure is exactly as described above, the corresponding condensation product is also obtained here.
3. In eine wäßrige Lösung von 2 Teilen benzaldehydsulfosaurem Natron wird eine Paste von 1 Teil 2,2-Dioxy-5,5-diaminoarsenobenzol eingetragen und durch Rühren fein3. In an aqueous solution of 2 parts of sodium benzaldehyde sulfonic acid is one Paste of 1 part of 2,2-dioxy-5,5-diaminoarsenobenzene entered and fine by stirring
6060
6565
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE272035C true DE272035C (en) |
Family
ID=528639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT272035D Active DE272035C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE272035C (en) |
-
0
- DE DENDAT272035D patent/DE272035C/de active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE272035C (en) | ||
| DE2906805C3 (en) | Concentrated, storage-stable solutions of coupling components for ice dye dyeing, their manufacture and use | |
| EP0528269A2 (en) | Flowable dyestuff preparations containing polyazodyes | |
| DE260235C (en) | ||
| DE633786C (en) | Process for the preparation of complex compounds of 1,3-dimethylxanthine | |
| DE293640C (en) | ||
| DE293866C (en) | ||
| DE268220C (en) | ||
| DE141967C (en) | ||
| DE267411C (en) | ||
| DE129031C (en) | Process for the preparation of easily soluble in water, resistant alkali salts of the decomposition products resulting from the alkaline hydrolysis of the native protein | |
| DE175593C (en) | ||
| DE194237C (en) | ||
| DE568943C (en) | Process for the representation of asymmetrical arsenic compounds | |
| DE172932C (en) | ||
| DE728533C (en) | Process for the preparation of salts of aliphatic aminosulfinic acids | |
| DE237787C (en) | ||
| DE251571C (en) | ||
| DE862941C (en) | Process for the preparation of stable solutions of sulfonamides | |
| DE180830C (en) | ||
| DE255030C (en) | ||
| DE185197C (en) | ||
| DE636310C (en) | Process for the production of condensation products with a tanning effect | |
| DE243583C (en) | ||
| DE537897C (en) | Process for the preparation of gold compounds of the thiobenzimidazole series |