DE1054090B - Process for the production of 3-aminomethyl-6,7-dioxy-phthalide or its N-monomethyl derivative - Google Patents
Process for the production of 3-aminomethyl-6,7-dioxy-phthalide or its N-monomethyl derivativeInfo
- Publication number
- DE1054090B DE1054090B DEA27211A DEA0027211A DE1054090B DE 1054090 B DE1054090 B DE 1054090B DE A27211 A DEA27211 A DE A27211A DE A0027211 A DEA0027211 A DE A0027211A DE 1054090 B DE1054090 B DE 1054090B
- Authority
- DE
- Germany
- Prior art keywords
- phthalide
- aminomethyl
- dioxy
- production
- monomethyl derivative
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- 239000000150 Sympathomimetic Substances 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 210000001525 retina Anatomy 0.000 description 2
- 230000001975 sympathomimetic effect Effects 0.000 description 2
- 229940064707 sympathomimetics Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JIRTYXPBFWHBDA-UHFFFAOYSA-N 3-(aminomethyl)-6,7-dimethoxy-3h-2-benzofuran-1-one Chemical compound COC1=CC=C2C(CN)OC(=O)C2=C1OC JIRTYXPBFWHBDA-UHFFFAOYSA-N 0.000 description 1
- XRCFWZNKTPZSBM-UHFFFAOYSA-N 6,7-dimethoxy-3-(methylaminomethyl)-3H-2-benzofuran-1-one Chemical compound CNCC1OC(=O)C2=C(C(=CC=C12)OC)OC XRCFWZNKTPZSBM-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DEUTSCHESGERMAN
Es wurde gefunden, daß 3-Aminomethyl-6,7-dioxyphthalid bzw. sein N-Monomethylderivat neue und besondere therapeutische Wirkungen aufweisen. Zum Beispiel fördern sie die Blutzirkulation der Retina in hohem Maße. Eine weitere Wirkung dieser Verbindungen besteht darin, daß sie schon in sehr kleinen Dosen die blutdruckerhöhende Wirkung der Sympathikomimetika, z. B. Adrenalin, erhöhen und ihre Wirkungsdauer verlängern. Sie besitzen eine sehr geringe Toxizität.It has been found that 3-aminomethyl-6,7-dioxyphthalide and its N-monomethyl derivative are new and special have therapeutic effects. For example, they promote blood circulation in the retina to a high degree. Another effect of these compounds is that even in very small doses they die antihypertensive effects of sympathomimetics, e.g. B. adrenaline, and extend their duration of action. They have a very low toxicity.
Im Sinne der Erfindung wird 3-Aminomethyl-6,7-dioxy-phthalid bzw. sein N-Monomethylderivat dadurch hergestellt, daß aus den entsprechenden, in 6- und 7-Stellung alkylierten oder aralkylierten Verbindungen die Alkyl- bzw. Aralkylreste in an sich bekannter Weise abgespalten werden.For the purposes of the invention, 3-aminomethyl-6,7-dioxy-phthalide is used or its N-monomethyl derivative prepared in that from the corresponding, in 6- and 7-position alkylated or aralkylated compounds, the alkyl or aralkyl radicals in a manner known per se be split off.
Zur Herstellung von 3-Aminomethyl-6,7-dioxy-phthalid verwendet man zweckmäßig das 3-Aminomethyl-6,7-dimethoxy-phthalid. 3-aminomethyl-6,7-dimethoxy-phthalide is expediently used for the preparation of 3-aminomethyl-6,7-dioxy-phthalide.
In den Beispielen der USA.-Patentschrift 2 268 990 sind N-alkylierte 3-Aminomethyl-5,7- und 4,5,6-oxyphthalide angeführt. Diese Verbindungen tragen an der Aminogruppe einen Substituenten mit mehr als einem C-Atom. Sie können zur Behandlung von allergischen Krankheiten und Infektionen verwendet werden.In the examples of U.S. Patent 2,268,990 are N-alkylated 3-aminomethyl-5,7- and 4,5,6-oxyphthalides cited. These compounds have a substituent with more than one on the amino group C atom. They can be used to treat allergic diseases and infections.
Die nach dem erfindungsgemäßen Verfahren hergestellten Verbindungen besitzen dagegen —■ wie bereits oben erwähnt — ganz besondere und von den in der USA.-Patentschrift angeführten Verbindungen abweichende Eigenschaften. Sie fördern die Blutzirkulation der Retina in hohem Maße, erhöhen schon in sehr kleinen Dosen die blutdruckerhöhende Wirkung der Sympathikomimetika und verlängern deren Wirkungsdauer.In contrast, the compounds prepared by the process according to the invention have - ■ as already mentioned above - very special compounds that differ from the compounds listed in the USA patent specification Properties. They promote the blood circulation of the retina to a great extent, increase it even in very small amounts Doses the hypertensive effect of the sympathomimetics and extend their duration of action.
10 g S-Aminomethyl-o^-dimethoxy-phthalid-hydro-Chlorid (F. 248 bis 249° C) werden in 60 ecm 45%iger Bromwasserstoffsäure 90 Minuten gekocht. Nach dem Abkühlen wird das ausgeschiedene Produkt abgenutscht und mit heißem Alkohol säurefrei gewaschen. Man erhält auf diese Weise 10 g S-Aminomethyl-oJ-dioxy-phthalidhydrobromid ais eine weiße, kristalline Verbindung, die in Wasser gut, in Äthanol schlecht löslich ist. F. 290 bis 292°C. Ausbeute: 94%.10 g of S-aminomethyl-o ^ -dimethoxy-phthalide-hydrochloride (F. 248 to 249 ° C) are boiled in 60 ecm 45% hydrobromic acid for 90 minutes. After this After cooling, the precipitated product is filtered off with suction and washed free of acid with hot alcohol. You get in this way 10 g of S-aminomethyl-oJ-dioxy-phthalide hydrobromide ais a white, crystalline compound which is readily soluble in water and poorly soluble in ethanol. F. 290 to 292 ° C. Yield: 94%.
10 g 3-Methylaminomethyl-6,7-dimethoxy-phthalid werden mit 60 ecm 45%iger Brom wasserstoff säure 90 MiVerfahren zur Herstellung10 g of 3-methylaminomethyl-6,7-dimethoxy-phthalide are mixed with 60 ecm of 45% hydrobromic acid 90 ml for the production
von S-Aminomethyl-e^-dioxy-phthalidof S-aminomethyl-e ^ -dioxy-phthalide
bzw. seinem N-Monomethylderivator its N-monomethyl derivative
Anmelder:Applicant:
ALKALOIDA Vegyeszeti Gyar,
Tiszavasväri (Ungarn)ALKALOIDA Vegyeszeti Gyar,
Tiszavasväri (Hungary)
Vertreter:
Dr. G. W. Lotterhos und Dr.-Ing. H. W. Lotterhos,Representative:
Dr. GW Lotterhos and Dr.-Ing. HW Lotterhos,
Patentanwälte,
Frankfurt/M., Lichtensteinstr. 3Patent attorneys,
Frankfurt / M., Lichtensteinstr. 3
Beanspruchte Priorität:
Ungarn vom 25. Mai 1956Claimed priority:
Hungary from May 25, 1956
Dr. Denes Beke, Budapest, Dr. Zoltan Dimer,Dr. Denes Beke, Budapest, Dr. Zoltan Dimer,
Szeged und Csaba Szäntay, Budapest (Ungarn),Szeged and Csaba Szäntay, Budapest (Hungary),
sind als Erfinder genannt wordenhave been named as inventors
nuten gekocht. Nach dem Abkühlen scheiden sich 11,6 g (90 °/0) einer weißen kristallinen Verbindung aus, die, aus 80%igem Äthanol umkristallisiert, bei 168 bis 1700C schmilzt. Im Vakuum über Phosphorpentoxyd getrocknet verliert sie 1 Mol Kristallwasser. Das so erhaltene 3-Methylaminomethyl-6,7-dioxy-phthalid schmilzt bei bis 246° C unter Zersetzung.utes cooked. After cooling, 11.6 g (90 ° / 0) secrete a white crystalline compound, composed of 80% ethanol recrystallized melts at 168-170 0 C. When dried in vacuo over phosphorus pentoxide, it loses 1 mol of water of crystallization. The 3-methylaminomethyl-6,7-dioxy-phthalide thus obtained melts at up to 246 ° C. with decomposition.
Claims (1)
USA.-Patentschrift Nr. 2 268 990;
Karrer, Lehrbuch der organischen Chemie, 12. Auflage (1954), S. 427.Considered publications:
U.S. Patent No. 2,268,990;
Karrer, Textbook of Organic Chemistry, 12th Edition (1954), p. 427.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU1054090X | 1956-05-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1054090B true DE1054090B (en) | 1959-04-02 |
Family
ID=11003122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEA27211A Pending DE1054090B (en) | 1956-05-25 | 1957-05-24 | Process for the production of 3-aminomethyl-6,7-dioxy-phthalide or its N-monomethyl derivative |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1054090B (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2268990A (en) * | 1939-08-22 | 1942-01-06 | Loewe Siegfried | Secondary and tertiary 3-amino-methyl-polyhydroxy-phthalides |
-
1957
- 1957-05-24 DE DEA27211A patent/DE1054090B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2268990A (en) * | 1939-08-22 | 1942-01-06 | Loewe Siegfried | Secondary and tertiary 3-amino-methyl-polyhydroxy-phthalides |
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