DE2507974B2 - COPPER OROTATE - Google Patents
COPPER OROTATEInfo
- Publication number
- DE2507974B2 DE2507974B2 DE19752507974 DE2507974A DE2507974B2 DE 2507974 B2 DE2507974 B2 DE 2507974B2 DE 19752507974 DE19752507974 DE 19752507974 DE 2507974 A DE2507974 A DE 2507974A DE 2507974 B2 DE2507974 B2 DE 2507974B2
- Authority
- DE
- Germany
- Prior art keywords
- copper
- orotate
- copper orotate
- salt
- cell systems
- 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.)
- Granted
Links
- WKQFGWKSVRJAMI-UHFFFAOYSA-L copper;2,4-dioxo-1h-pyrimidine-6-carboxylate Chemical compound [Cu+2].[O-]C(=O)C1=CC(=O)NC(=O)N1.[O-]C(=O)C1=CC(=O)NC(=O)N1 WKQFGWKSVRJAMI-UHFFFAOYSA-L 0.000 title claims description 10
- 239000010949 copper Substances 0.000 claims description 9
- 229910052802 copper Inorganic materials 0.000 claims description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- XTVRPSBYSGATQQ-UHFFFAOYSA-N 1,2-dinitrosodioxidane Chemical compound O=NOON=O XTVRPSBYSGATQQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 description 4
- 230000001684 chronic effect Effects 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 3
- 239000005749 Copper compound Substances 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- 229960005010 orotic acid Drugs 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 241000282412 Homo Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- LROWILPKXRHMNL-UHFFFAOYSA-N copper;thiourea Chemical compound [Cu].NC(N)=S LROWILPKXRHMNL-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001373 regressive effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000010981 turquoise Substances 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid
-
- 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 Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Die Erfindung betrifft das Kupfersalz der Orotsäure der StrukturformelThe invention relates to the copper salt of orotic acid of the structural formula
ONOONOONOONO
und der Bruttoformel Cu(CsHsNzOOa- Die erfindungsigemäße Verbindung eignet sich insbesondere zur therapeutischen Verwendung bei der Kupfer-Therapie in oraler oder rektaler Verabreichung.and the gross formula Cu (CsHsNzOOa- The inventive Compound is particularly suitable for therapeutic use in copper therapy in oral or rectal administration.
Es wurde gefunden, daß sich Kupfer-orotat in besonders wirksamer Weise für die Behandlung von menschlichen Erkrankungen eignet, die mit einer krankheitstypischen Mobilisierung von Kupfer aus Zellsystemen einhergehen, insbesondere die Behandlung des chronischen Rheumatismus.It has been found that copper orotate is particularly effective for the treatment of human diseases that are characterized by a mobilization of copper that is typical of the disease Cell systems, especially the treatment of chronic rheumatism.
Es ist an sich seit langem bekannt, daß Kupfer-Verbindungen eine interessante Wirkung gegen Rheuma-Erkrankungen entfalten können, z. B. das S-Kupfersalz des N-Allyl-N'-{3-carboxyphenyi)-isothioharnstoffs und Kupfer-Caseinhydrolysat-Komplexe. Diese bekannten Präparate mußten jedoch im Laufe der Zeit aufgegeben werden, weil ihre Giftigkeit, z. B. auf die Nieren, großIt has long been known that copper compounds can develop an interesting effect against rheumatic diseases, e.g. B. the S-copper salt of N-allyl-N '- {3-carboxyphenyi) -isothiourea and Copper-casein hydrolyzate complexes. However, these known preparations had to be abandoned in the course of time because their toxicity, e.g. B. on the kidneys, great
ίο war.ίο was.
Untersuchungen mit dem Ziel einer gerichteten bzw. gezielten Kupfer-Aufladung von entzündlich veränderten Zellsystemen führten nun zum erfindungsgemäßen Kupfer-orotatInvestigations with the aim of a directed or targeted copper charge of inflammatory changes Cell systems now led to the copper orotate according to the invention
Bei am Menschen (16 Patienten) durchgeführten Versuchen mit primär chronischem Gelenkrheumatismus (PcP) ergab sich, daß Kupfer-orotat, im Vergleich zum eingangs erwähnten Kupfer-Isothioharnstoff-Salz 600- bis 800mal stärker wirksam istIn tests carried out on humans (16 patients) with primarily chronic rheumatoid arthritis (PcP) was found to be copper orotate, in comparison is 600 to 800 times more effective than the copper isothiourea salt mentioned at the outset
Außerdem wurde bei weiteren Tierversuchen an Impftumoren der Ratte und Spontantumoren der Maus festgestellt, daß Kupfer-orotat stark regressiv wirktIn addition, in further animal experiments on vaccine tumors in rats and spontaneous tumors in mice found that copper orotate has a strong regressive effect
Aufgrund dieser Erkenntnisse stellt sich Kupfer-orotat als ein hochwirksamer, allen bisher bekannten Kupfer-Verbindungen weit überlegener Stoff von antirheumatischer, entzündungshemmender Wirkung dar, der bei hauptsächlich oraler Verabreichung für die Behandlung von menschlichen Erkrankungen, die mit einer krankheitstypischen Mobilisierung von Kupfer aus Zellsystemen einhergehen, insbesondere dem chronischen Rheumatismus, besonders geeignet erscheintBased on these findings, copper orotate turns out to be a highly effective one known to all Copper compounds far superior substance of anti-rheumatic, anti-inflammatory effects when administered primarily orally for the treatment of human diseases associated with mobilization of copper from cell systems typical of the disease, especially the chronic one Rheumatism, seems particularly suitable
Kupfer-orotat (bzw. di-orotat) kann synthetisch in der Weise gewonnen werden, daß man bei normaler oder etwas erhöhter Temperatur ein lösliches Kupfersalz in stöchiometrischer Menge in einer wäßrigen Lösung mit Orotsäure umsetzt. Das Kupfersalz, z. B. C11CI2 oder Cu(CH3COO)j, wird unter Rühren langsam eingegeben, wobei Kupfer-orotat ausfällt und abfiltriert wird. Die Kristalle werden mit heißem Wasser gewaschen und dann getrocknet. Es entstehen eine türkisfarbene, feinkristalline Substanz, die in den üblichen Lösungsmitteln schwer löslich ist, d. h. ihre Lösungsfähigkeit liegt unter 0,25%; der Schmelzpunkt liegt über 35O0C. Die Gehaltsbestimmung im Wege der komplexometrischen Kupfertitration (Fehlergrenze ± 1%) ergibt ber. 15,52% Cu.Copper orotate (or di-orotate) can be obtained synthetically by reacting a soluble copper salt in an aqueous solution with orotic acid in a stoichiometric amount at normal or slightly elevated temperature. The copper salt, e.g. B. C11CI2 or Cu (CH3COO) j, is slowly added with stirring, whereupon copper orotate precipitates and is filtered off. The crystals are washed with hot water and then dried. The result is a turquoise, finely crystalline substance that is sparingly soluble in the usual solvents, ie its solubility is below 0.25%; the melting point is above 35O 0 C. The determination of the content by means of complexometric copper titration (error limit ± 1%) results in 15.52% Cu.
Claims (2)
1. Kupfer-orotat der FormelPatent claims:
1. Copper orotate of the formula
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752507974 DE2507974C3 (en) | 1975-02-25 | Copper orotate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752507974 DE2507974C3 (en) | 1975-02-25 | Copper orotate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2507974A1 DE2507974A1 (en) | 1976-09-02 |
| DE2507974B2 true DE2507974B2 (en) | 1977-04-14 |
| DE2507974C3 DE2507974C3 (en) | 1977-12-01 |
Family
ID=
Also Published As
| Publication number | Publication date |
|---|---|
| DE2507974A1 (en) | 1976-09-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: PERMICUTAN-KG DR. EULER, 4790 PADERBORN, DE |
|
| 8339 | Ceased/non-payment of the annual fee |