DE1593297C3 - - Google Patents
Info
- Publication number
- DE1593297C3 DE1593297C3 DE19661593297 DE1593297A DE1593297C3 DE 1593297 C3 DE1593297 C3 DE 1593297C3 DE 19661593297 DE19661593297 DE 19661593297 DE 1593297 A DE1593297 A DE 1593297A DE 1593297 C3 DE1593297 C3 DE 1593297C3
- Authority
- DE
- Germany
- Prior art keywords
- glucosamine
- aneurine
- bis
- glucosamine salt
- pyrophosphate
- 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
Links
- JZRWCGZRTZMZEH-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 claims description 16
- MSWZFWKMSRAUBD-QZABAPFNSA-N beta-D-glucosamine Chemical class N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-QZABAPFNSA-N 0.000 claims description 15
- 235000019157 thiamine Nutrition 0.000 claims description 14
- 239000011721 thiamine Substances 0.000 claims description 14
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 12
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 11
- 235000011180 diphosphates Nutrition 0.000 claims description 11
- RNBGYGVWRKECFJ-ZXXMMSQZSA-N alpha-D-fructofuranose 1,6-bisphosphate Chemical compound O[C@H]1[C@H](O)[C@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O RNBGYGVWRKECFJ-ZXXMMSQZSA-N 0.000 claims description 8
- 229940025237 fructose 1,6-diphosphate Drugs 0.000 claims description 8
- HZSAJDVWZRBGIF-UHFFFAOYSA-O thiamine monophosphate Chemical compound CC1=C(CCOP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N HZSAJDVWZRBGIF-UHFFFAOYSA-O 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 10
- 239000013081 microcrystal Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 5
- 229960002442 glucosamine Drugs 0.000 description 4
- 241000700159 Rattus Species 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000723382 Corylus Species 0.000 description 2
- 235000001543 Corylus americana Nutrition 0.000 description 2
- 235000007466 Corylus avellana Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000001177 diphosphate Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- WDZWAUROVWONEO-BWIGVGPWSA-N (2R)-2-[(R)-carboxy(hydroxy)methyl]-4-(4-hydroxyphenyl)-3-(methylamino)oxetane-2-carboxylic acid Chemical compound CNC1[C@@]([C@H](C(O)=O)O)(C(O)=O)OC1C(C=C1)=CC=C1O WDZWAUROVWONEO-BWIGVGPWSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- 208000007848 Alcoholism Diseases 0.000 description 1
- 206010003840 Autonomic nervous system imbalance Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010029240 Neuritis Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 206010036105 Polyneuropathy Diseases 0.000 description 1
- 201000007930 alcohol dependence Diseases 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 230000003555 analeptic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229940125692 cardiovascular agent Drugs 0.000 description 1
- 239000002327 cardiovascular agent Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229950001485 cocarboxylase Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 208000019629 polyneuritis Diseases 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- YXVCLPJQTZXJLH-UHFFFAOYSA-N thiamine(1+) diphosphate chloride Chemical compound [Cl-].CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N YXVCLPJQTZXJLH-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
- C07H5/06—Aminosugars
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/093—Polyol derivatives esterified at least twice by phosphoric acid groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Description
Die Erfindung betrifftThe invention relates to
1. das Bis-D-glucosaminsalz von ß-Aminoäthanolphosphat, 1. the bis-D-glucosamine salt of ß-aminoethanol phosphate,
2. das Mono-D-glucosaminsalz von Aneurinmonophosphatchlorid, 2. the mono-D-glucosamine salt of aneurine monophosphate chloride,
3. das Bis-D-glucosaminsalz von Aneurinmonophosphatchlorid, 3. the bis-D-glucosamine salt of aneurine monophosphate chloride,
4. das Bis-D-glucosaminsalz von Fructose-l,6-diphosphat, 4. the bis-D-glucosamine salt of fructose-1,6-diphosphate,
5. das Tetra-D-glucosaminsalz von Fructose-l,6-diphosphat, 5. the tetra-D-glucosamine salt of fructose-1,6-diphosphate,
6. das Bis-D-glucosaminsalz von Aneurinpyrophosphat und6. the bis-D-glucosamine salt of aneurine pyrophosphate and
7. das Mono-D-glucosaminsalz von Aneurinpyrophosphat. 7. the mono-D-glucosamine salt of aneurine pyrophosphate.
Das Verfahren zur Herstellung dieser D-glucosaminsalze ist erfindungsgemäß dadurch gekennzeichnet, daß man etwa 20gewichtsprozentige Lösungen von /S-Aminoäthanolphosphat, Aneurinmonophosphatchlorid, Fructose-l,6-diphosphat oder Aneurinpyrophosphat allmählich unter Rühren bei einer Temperatur von höchstens 400C mit der entsprechenden stöchiometrischen Menge D-Glucosamin bei einem pH-Wert zwischen 3 und 7 versetzt, die Mischung anschließend etwa 1 Stunde in diesem pH-Bereich unter Rühren umsetzt, das Reaktionsgemisch mit Wasser auf eine Konzentration von 10 Gewichtsprozent verdünnt, filtriert, das Filtrat 6 bis 25 Stunden auf —50 bis —100C vorkühlt und gefriertrocknet. Es erfolgt hierbei eine Quaternisierung des Stickstoffatoms des D-Glucosamins durch die genannten Phosphorsäureester. The method for producing these D-glucosamine according to the invention characterized in that about 20gewichtsprozentige solutions of / S-Aminoäthanolphosphat, Aneurinmonophosphatchlorid, fructose-l, 6-diphosphate or Aneurinpyrophosphat gradually stoichiometric with stirring at a temperature not exceeding 40 0 C with the corresponding Amount of D-glucosamine added at a pH between 3 and 7, the mixture then reacted for about 1 hour in this pH range with stirring, the reaction mixture diluted with water to a concentration of 10 percent by weight, filtered, the filtrate 6 to 25 hours pre-cooling to -10 0 C to -50 and freeze-dried. In this case, the nitrogen atom of D-glucosamine is quaternized by the phosphoric acid esters mentioned.
Gegenüber den als Pharmazeutika verwendeten Phosphorsäureestern besitzen deren D-Glucosaminsalze generell den Vorzug einer geringeren Toxizität und eines langsameren Abbaus im Organismus.Compared to the phosphoric acid esters used as pharmaceuticals, they have D-glucosamine salts generally the advantage of a lower toxicity and a slower degradation in the organism.
Insbesondere ist das Bis-D-glucosaminsalz von jö-Aminoäthanolphosphat gegenüber Alkalisalzen bzw. Erdalkalisalzen des /J-Aminoäthanolphosphats, die beiIn particular, the bis-D-glucosamine salt of jö-aminoethanol phosphate is compared to alkali salts or Alkaline earth salts of the / I-aminoethanol phosphate, which at
ίο vegetativer Dystonie indiziert werden, und vergleichbaren, auf das periphere Nervensystem wirkenden Therapeutica wegen größerer Verträglichkeit und der geringeren Toxizität überlegen. Gegenüber bekannten, j auf das Zentralnervensystem wirkenden Herz- und Kreislaufmitteln, wie Pentamethylentetrazol oder 1 - (4 - Hydroxyphenyl) - 2 - methylaminoäthanol - tartrat sind neben der geringeren Toxizität auch die geringeren Nebenwirkungen hervorzuheben. Die an Ratten bestimmte LD50 beträgt bei dem erfindungsgemäßen Bis-D-glucosaminsalz von /3-Aminoäthanolphosphat 1800 mg/kg intravenös und 6000 mg/kg subkutan. ί Gegenüber /J-Aminoäthanolphosphat wurde eine aus- | geprägtere analeptische Kreislaufwirkung beobachtet. ' Die Mono- und Bis-D-glucosaminsalze von Aneurinmonophosphatchlorid (LD50 bei der Ratte 2450 mg/kg intravenös und 5000 mg/kg intraperitoneal) und von Aneurinpyrophosphat (LD50 bei der Ratte 2200 mg/kg intravenös und 7100 mg/kg intraperitoneal) sind wesentlich weniger toxisch als das wirkungsmäßig gleichgerichtete Vitamin B1 (Thiamin) (LD50 84 mg/kg intravenös und 329 mg/kg subkutan) bzw. Aneurinpyrophosphat (= Cocarboxylase) und können daher als Mittel zur Behandlung von Polyneuritis und des Alkoholismus höher dosiert werden oder zur Sloßbehandlung eingesetzt werden. Außerdem wurde eine erhebliche Wirkungsdauerverlängerung beobachtet.ίο vegetative dystonia are indicated, and are superior to comparable therapeutic agents acting on the peripheral nervous system because of their greater tolerance and lower toxicity. Compared to known cardiovascular agents that act on the central nervous system, such as pentamethylenetetrazole or 1- (4-hydroxyphenyl) -2-methylaminoethanol-tartrate, in addition to the lower toxicity, the lower side effects are to be emphasized. The LD 50 determined in rats for the bis-D-glucosamine salt of / 3-aminoethanol phosphate according to the invention is 1800 mg / kg intravenously and 6000 mg / kg subcutaneously. ί Compared to / J-Aminoethanolphosphat an off | more pronounced analeptic circulatory effects were observed. The mono- and bis-D-glucosamine salts of aneurine monophosphate chloride (LD 50 in the rat 2450 mg / kg intravenous and 5000 mg / kg intraperitoneally) and of aneurine pyrophosphate (LD 50 in the rat 2200 mg / kg intravenous and 7100 mg / kg intraperitoneally ) are significantly less toxic than vitamin B 1 (thiamine) (LD 50 84 mg / kg intravenous and 329 mg / kg subcutaneously) or aneurine pyrophosphate (= cocarboxylase) and can therefore be used as an agent for the treatment of polyneuritis and alcoholism be dosed or used for slough treatment. In addition, a considerable increase in the duration of action was observed.
Die Bis- bzw. Tetra-D-glucosaminsalze von Fruc-The bis- or tetra-D-glucosamine salts of fruit
tose-l,6-diphosphat (LD50 bei Swiss-Mäusen über 6000 mg/kg subkutan, über 1500 mg/kg intravenös) sind verglichen mit dem als Leberschutzmittel gegenüber toxischen Einwirkungen, z. B. durch Alkohol, bekannten Fructose-l,6-diphosphat länger wirksam. Im Tierversuch wurde eine Schutzdauer von 20 Tagen gegenüber 2 bis 3 Tagen bei der bekannten Verbindung · festgestellt.tose-1,6-diphosphate (LD 50 in Swiss mice over 6000 mg / kg subcutaneously, over 1500 mg / kg intravenously) are compared with the liver protection agent against toxic effects, e.g. B. by alcohol, known fructose-1,6-diphosphate longer effective. In animal experiments, a duration of protection of 20 days versus 2 to 3 days for the known compound was found.
Außerdem stellt D-Glucosamin einen Mangelstoff im Organismus dar und wird diesem durch die erfindungsgemäßen Verbindungen zugeführt. Die folgenden Beispiele sollen die Erfindung näher veranschaulichen.In addition, D-glucosamine represents a deficiency in the organism and is this by the invention Connections fed. The following examples are intended to further illustrate the invention illustrate.
Beispiele Ibis7Examples Ibis7
Die jeweiligen Reaktionsteilnehmer, deren Mengen, die Reaktionsbedingungen, die jeweils erhaltenen D-Glucosaminsalze sowie deren Eigenschaften sind in Tabelle I zusammengefaßt. Die Herstellung der einzelnen D-Glucosaminsalze wurde wie folgt durchgeführt: The respective reactants, their amounts, the reaction conditions, the respectively obtained D-glucosamine salts and their properties are summarized in Table I. The making of each D-glucosamine salts were performed as follows:
In ein in einem thermostatisch geregelten Bad befindliches Reaktionsgefäß wurde jeweils eine etwa 20gewichtsprozentige wäßrige Lösung des betreffenden Phosphorsäureesters, welcher in der jeweiligen Lösung in der in Tabelle I angegebenen Menge enthalten war, eingefüllt. Zu der in dem Reaktionsgefäß befindlichen Phosphorsäureesterlösung wurde innerhalb von 30 bis 90 Minuten freies D-Glucosamin in der jeweils angegebenen Menge zugesetzt. Das verwendete freie D-Glucosamin bestand aus weißen, in ;In a reaction vessel located in a thermostatically controlled bath, approx 20 weight percent aqueous solution of the phosphoric acid ester concerned, which in the respective Solution was contained in the amount specified in Table I, filled. To the one in the reaction vessel The phosphoric acid ester solution contained within 30 to 90 minutes was free D-glucosamine in added to the specified amount. The free D-glucosamine used consisted of white, in;
Wasser sehr gut löslichen Kristallen mit einem Schmelzpunkt von 110° C und einer spezifischen Drehung, gemessen in einer l%igen wäßrigen Lösung, d. h. bei einer Konzentration von 1 g D-Glucosamin-Base in 100 ml Wasser von [α]20 = +47,5°, und besaß folgende Analysenwerte:Water very soluble crystals with a melting point of 110 ° C and a specific rotation, measured in a 1% aqueous solution, ie at a concentration of 1 g of D-glucosamine base in 100 ml of water of [α] 20 = +47 , 5 °, and had the following analysis values:
Berechnet ... C 40,22, H 7,31, N 7,82, O 44,65%; gefunden ... C40,21, H7,3, N7,79, O44,6%.Calculated ... C 40.22, H 7.31, N 7.82, O 44.65%; found ... C40.21, H7.3, N7.79, O44.6%.
Die Zugabe des D-Glucosamins zu der Phosphorsäureesterlösung erfolgte unter Rühren in kleinen Anteilen, wobei die in Tabelle I angegebene Temperatur eingehalten wurde. Während der Zugabe des D-Glucosamins zu der Phosphorsäureesterlösung wurde laufend die Änderung des pH-Wertes des Reaktionsgemisches kontrolliert, wobei im Falle, daß der pH-Wert von 7 überschritten wurde, die Zugabe von D-Glucosamin unterbrochen und/oder weiterer Phosphorsäureester zugegeben wurde. Nach beendeter Glucosaminzugabe wurde das Reaktionsgemisch 1 Stunde lang gerührt, worauf es mit Wasser bis zu einer Konzentration von 10% verdünnt wurde. Schließlich wurde das Reaktionsgemisch während der in Tabelle I angegebenen Zeit bei den ebenfalls inThe addition of the D-glucosamine to the phosphoric acid ester solution took place with stirring in small portions, the temperature given in Table I. was adhered to. During the addition of the D-glucosamine to the phosphoric acid ester solution the change in the pH of the reaction mixture was continuously monitored, in the event that the pH 7 was exceeded, the addition of D-glucosamine was interrupted and / or further phosphoric acid ester was admitted. When the addition of glucosamine was complete, the reaction mixture was stirred for 1 hour, after which it was mixed with water up to at a concentration of 10%. Finally, the reaction mixture was during the in Table I for the time also in
ίο Tabelle I angegebenen Temperaturen vorgefroren und endlich in bekannter Weise im Autoklav unter Vakuum gefriergetrocknet.ίο Table I pre-frozen and specified temperatures finally freeze-dried in a known manner in an autoclave under vacuum.
Sämtliche in den Beispielen 1 bis 7 erhaltenen Salze sind hygroskopisch und ausgezeichnet wasserlöslich.All of the salts obtained in Examples 1 to 7 are hygroscopic and extremely water-soluble.
is Sie besitzen die in der folgenden Tabelle I angegebenen physikalischen Eigenschaften.is You have those given in Table I below physical properties.
MrMr
Tabelle I (Fortsetzung)Table I (continued)
Nr.example
No.
temperatur
(in 0QPre-frozen
temperature
(in 0 Q
Vorgefrierung
(in Std.)Duration of
Pre-freezing
(in hours)
2
3
4
5
6
71
2
3
4th
5
6th
7th
-30°
-35°
-40°
-40°
-35°
-35°-35 °
-30 °
-35 °
-40 °
-40 °
-35 °
-35 °
10
10
20
20
10
108th
10
10
20th
20th
10
10
Mono-D-glucosaminsalz von Aneurinmonophosphat-
chlorid
Bis-D-glucosaminsalz von Aneurinmonophosphat-
chlorid
Bis-D-glucosaminsalz von Fructose-l,6-diphosphat
Tetra-D-glucosaminsalz von Fructose-l,6-diphosphat
Bis-D-glucosaminsalz von Aneurinpyrophosphat
Mono-D-glucosaminsalz von AneurinpyrophosphatBis-D-glucosamine salt of / S-aminoethanol phosphate
Mono-D-glucosamine salt of aneurine monophosphate
chloride
Bis-D-glucosamine salt of aneurine monophosphate
chloride
Bis-D-glucosamine salt of fructose-1,6-diphosphate
Tetra-D-glucosamine salt of fructose-1,6-diphosphate
Bis-D-glucosamine salt of aneurine pyrophosphate
Mono-D-glucosamine salt of aneurine pyrophosphate
Tabelle I (Fortsetzung)Table I (continued)
Beispiel Nr.Example no.
Ausbeute (in %); Summenformel; physikalische Eigenschaften
Elementar-Analyse
C]HjNYield (in%); Molecular formula; physical properties elemental analysis
C] HjN
weiße Mikrokristallewhite microcrystals
013 weiße Mikrokristalle 013 white microcrystals
97% C24H44N6O14PClS strohfarbene Mikrokristalle97% C 24 H 44 N 6 O 14 PClS straw-colored microcrystals
95% C18H40N2O22P2 95% C 18 H 40 N 2 O 22 P 2
hell haselnußbraune Mikrokristallelight hazelnut brown microcrystals
95»/oC30H66N4032P2 95 »/ oC 30 H 66 N 4 0 32 P 2
hell haselnußbraune Mikrokristallelight hazelnut brown microcrystals
96% C24H45N6O17P2ClS96% C 24 H 45 N 6 O 17 P 2 ClS
weiße Mikrokristallewhite microcrystals
957,,C18H32N5O12P2ClS weiße Mikrokristalle957 ,, C 18 H 32 N 5 O 12 P 2 ClS white microcrystals
berech.calc.
gefun.found
berech.calc.
gefun.found
berech.calc.
gefun.found
berech.calc.
gefun.found
berech.calc.
gefun.found
berech.calc.
gefun.found
berech.calc.
gefun.found
6,202 6,19 5,53 5,496.202 6.19 5.53 5.49
4,91 4,114.91 4.11
8,8718,871
8,68.6
5,8625,862
5,85.8
7,557.55
7,37.3
9,749.74
9,579.57
Claims (8)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER0043067 | 1966-04-15 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1593297A1 DE1593297A1 (en) | 1970-04-16 |
| DE1593297B2 DE1593297B2 (en) | 1973-10-25 |
| DE1593297C3 true DE1593297C3 (en) | 1974-07-25 |
Family
ID=7406836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661593297 Granted DE1593297B2 (en) | 1966-04-15 | 1966-04-15 | D Glucosamine salts and processes for their preparation |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1593297B2 (en) |
-
1966
- 1966-04-15 DE DE19661593297 patent/DE1593297B2/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE1593297B2 (en) | 1973-10-25 |
| DE1593297A1 (en) | 1970-04-16 |
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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 |