CN1355169A - Vanadium compound and its preparing process and usage - Google Patents
Vanadium compound and its preparing process and usage Download PDFInfo
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- CN1355169A CN1355169A CN 00128053 CN00128053A CN1355169A CN 1355169 A CN1355169 A CN 1355169A CN 00128053 CN00128053 CN 00128053 CN 00128053 A CN00128053 A CN 00128053A CN 1355169 A CN1355169 A CN 1355169A
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- nanjiasuan
- barium
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Abstract
The present invention relates to a vanadium compound C10H6O7V with molecular weight of 289. It is prepared through the reaction between vanadylic sulfate and barium alpha-furancarboxylate. The said compound can be used to prepare the medicine for treating diabetes with lowerd poison.
Description
The present invention relates to a kind of vanadium compound, and the preparation method of this compound and the application in the medicine of preparation treatment diabetes.
Diabetes are the common big diseases of the elderly, and its main clinical characteristics is that the glucose content in the blood samples of patients is higher than normal population.Diabetes can be divided into I type and II type by the pathology characteristic.The I type adopts the treatment of external source supplementation with insulin usually owing to hypoinsulinism in the body causes; To be target cell produce the resistance effect to Regular Insulin to the II type causes, mostly occurs the obese people, still lacks treatment means safely and effectively at present.Vanadium is the trace element of needed by human, furthers investigate in a large number and investigation shows that the ubiquity vanadium lacks and insufficient state in diabetic subject's body, and the compound of oral vanadium can improve the state of an illness, and lowering blood glucose is all effective to I type and type ii diabetes.Therefore think that the compound of vanadium has the insulin resistance of elimination or " Insulin-Like " (insulin-mimics) acts on." J.Am.Chem.Soc " nineteen ninety-fives 117 " Reaction Chemistry of BMOV; Bis (maltolato) oxovanadium (IV)-APotent Insulin Mimetic Agent " literary composition of carrying of periodical, the two voitol vanadyl of a kind of compound (being called for short BOMV) are disclosed, STZ-diabetic mice oral test has significant hypoglycemic activity, can be used for treating hypertension and diabetes, but can cause that to GI side effect, its preparation method is: with VOSO
4.3H
2O is dissolved in water, joins in the hydrothermal solution of voitol, stirs 12 hours, transfers pH value to 8.5 with KOH, afterwards mixing solutions is refluxed 12 hours, obtains geometric configuration and is the tapered purple green precipitate product in four directions." Vanadium Complexes as InsulinMimetic Agents:Coordination Chemistry and in Vivo Studies ofOxovanadium (IV) and Dioxovanadium (V) Compexes Formed from NaturallyOccurring Chelating Oxazolinate; Thiazolinate; or Picolinate Units " literary composition that " Inorg.Chem. " 1999 38 phases publish, two (pyridine carboxylic acid) vanadyl of a kind of compound (being called for short VO-MPA) have been disclosed, the sustainable lowering blood glucose of oral test in during the STZ-diabetic mice is certain, its preparation method is: the aqueous solution of 2-Pyridinecarboxylic Acid is joined VOSO
4.3H
2In the aqueous solution of O, drip 2N NaOH solution, make pH value rise to 4.4, stir, leave standstill, suction filtration, washing obtains blue precipitation product.
First purpose of the present invention provides a kind of new vanadium compound with pharmaceutical use.
Another object of the present invention provides the preparation method of the described compound of a kind of aforementioned purpose.
Another object of the present invention provides the purposes of purpose one described compound aspect the medicine of preparation treatment diabetes.
The described vanadium compound name of the object of the invention is called two (α-Fu Nanjiasuan) vanadyl, and its English name is that (oxovanadium (IV) of α-furancarboxylato) claims the pyromucic acid vanadyl again, molecular formula: C to bis
10H
6O
7V, molecular weight FW=289, its chemical structural formula:
The preparation method of invention compound comprises following process steps successively:
A. α-Fu Nanjiasuan dissolving back is added barium carbonate and under usual conditions, carries out chemical reaction,
B. remove by filter barium carbonate, concentrated mother liquor obtains α-Fu Nanjiasuan barium,
C. α-Fu Nanjiasuan barium and vanadylic sulfate are blended in and carry out chemical reaction under the usual conditions,
D. remove by filter barium sulfate, concentrated mother liquor obtains green two (α-Fu Nanjiasuan) vanadyl crystallization.
Aforesaid compounds process for production thereof can carry out under looser condition, also need not carry out strict control as the mol ratio of reaction at normal temperatures and pressures, the comparatively preferred parameter area of its reaction is as follows: the α-Fu Nanjiasuan among the step a and the reaction of barium carbonate can be carried out under the mol ratio at 2: 1.05～2: 1.10,40～60 ℃ of temperature of reaction, 3～5 hours reaction times, concentrating among the step b can be carried out under 50～70 ℃, α-Fu Nanjiasuan barium recrystallization in water is purified, the α-Fu Nanjiasuan barium among the step c and the reaction of vanadylic sulfate can be carried out under the mol ratio at 1: 1, reaction times 2-3 hour, concentrating in the steps d can be carried out under 40～60 ℃, and two (α-Fu Nanjiasuan) vanadyl crystallization recrystallization in water is purified.
The chemical equation of the α-Fu Nanjiasuan in the inventive method and the chemical equation of barium carbonate and α-Fu Nanjiasuan barium and vanadylic sulfate is:
Chemical reaction between chemical reaction between above-mentioned α-Fu Nanjiasuan and the barium carbonate and α-Fu Nanjiasuan barium and the vanadylic sulfate can slowly take place under the room temperature normal pressure, and the length in reaction times only influences degree and the product yield that reaction is finished.
The contriver finds that this compound has significant hypoglycemic activity, and toxicity is lower, can use its treatment diabetes.
As long as it is above that the purity of the raw materials used α-Fu Nanjiasuan of the present invention, barium carbonate and vanadylic sulfate reaches chemical pure, the source all can be buied from market.
Two (α-Fu Nanjiasuan) vanadyl of compound of the present invention have fat-soluble and water-soluble, be absorption of human body easily, on the animal model of diabetes, can obviously improve symptom, its hypoglycemic activity is better than at present the vanadium compound of report both at home and abroad, toxicity is low, and have Orally active, demonstrate good prospects for application.
Embodiment 1: invent described compound and preparation thereof
After getting a certain amount of commercially available α-Fu Nanjiasuan dissolving, add barium carbonate, both mol ratios 2: 1.05, reacted 3 hours down at 40 ℃, remove by filter excessive barium carbonate, 50 ℃ of concentrated mother liquors of normal pressure obtain α-Fu Nanjiasuan barium, recrystallization is purified in water, α-Fu Nanjiasuan barium after the purification mixes to wait molar ratio with commercially available vanadylic sulfate, and stirring reaction removed by filter BaSO after 2 hours
4, concentrated mother liquor obtains green two (α-Fu Nanjiasuan) vanadyl crystallization under 40 ℃ of normal pressures, and recrystallization is purified and is obtained product, productive rate 81% in water then.The characteristic parameter analysis result data is as follows: ultimate analysis: calculated value: measured value
C, 41.52; H, 2.08; V, 17.61 C, 41.22; H, 2.28; V, 17.03IR (cm
-1, the KBr compressing tablet): 1642 (s, v
As(COO)), 1370 (s, v (COO)), 985 (s, V=O), 540 (m, V-O) .UV-vis (H
2O): λ
MAX=470nm.FAB-MS:m/z=259 (M
+), 112 (C
5H
3O
3 +), 67 (C
4H
3O
+). δ
H: 7.54 (1H, d, α-H), 6.42 (1H, d, β-H), 7.10 (1H, d, β-H). embodiment 2: invent described compound and preparation thereof
After getting a certain amount of commercially available α-Fu Nanjiasuan dissolving, add barium carbonate, both mol ratios 2: 1.08, reacted 4 hours down at 45 ℃, remove by filter excessive barium carbonate, 60 ℃ of following concentrated mother liquors of normal pressure obtain α-Fu Nanjiasuan barium, recrystallization is purified in water, α-Fu Nanjiasuan barium after the purification mixes to wait molar ratio with commercially available vanadylic sulfate, and stirring reaction removed by filter BaSO after 3 hours
4, concentrated mother liquor obtains green two (α-Fu Nanjiasuan) vanadyl crystallization under 50 ℃ of normal pressures, and recrystallization is purified and is obtained product, productive rate 83% in water then.The characteristic parameter analysis result data is as follows: ultimate analysis: calculated value: measured value
C, 41.52; H, 2.08; V, 17.61 C, 41.41; H, 2.08; V, 17.45IR (cm
-1, the KBr compressing tablet): 1646 (s, v
As(COO)), 1366 (s, v (COO)), 981 (s, V=O), 540 (m, V-O) .UV-vis (H
2O): λ
MAX=473nm.FAB-MS:m/z=289 (M
+), 112C
5H
3O
3 +), 67 (C
4H
3O
+). δ
H: 7.50 (1H, d, α-H), 6.38 (1H, d, β-H), 7.14 (1H, d, β-H). embodiment 3: invent described compound and preparation thereof
After getting a certain amount of commercially available α-Fu Nanjiasuan dissolving, add barium carbonate, both mol ratios 2: 1.10, reacted 5 hours down at 60 ℃, remove by filter excessive barium carbonate, 70 ℃ of following concentrated mother liquors of normal pressure obtain α-Fu Nanjiasuan barium, recrystallization is purified in water, α-Fu Nanjiasuan barium after the purification mixes to wait molar ratio with commercially available vanadylic sulfate, and stirring reaction removed by filter BaSO after 3 hours
4, concentrated mother liquor obtains green two (α-Fu Nanjiasuan) vanadyl crystallization under 60 ℃ of normal pressures, and recrystallization is purified and is obtained product, productive rate 79% in water then.The characteristic parameter analysis result data is as follows: ultimate analysis: calculated value: measured value
C, 41.52; H, 2.08; V, 17.61 C, 41.33; H, 2.21; V, 17.54IR (cm
-1, the KBr compressing tablet): 1640 (s, v
As(COO)), 1372 (s, v (COO)), 987 (s, V=O), 540 (m, V-O) .UV-vis (H
2O): λ
MAX=471nm.FAB-MS:m/z=289 (M
+), 112 (C
5H
3O
3 +), 67 (C
4H
3O
+). δ
H: 7.52 (1H, d, α-H), 6.39 (1H, d, β-H), 7.12 (1H, d, β-H). embodiment 4: the hypoglycemic activity of invention compound
Adopt the ICR mouse, the phonetic heavy stone used as an anchor of injection 80mg/kg four oxygen is set up the model of mouse diabetes.(blood sugar＞11mmol/L) is divided into solvent group (1.4% polyvinyl alcohol+5% propylene glycol solution) at random, organized by examination with the mouse of confirming as diabetes, irritating stomach every day gives solvent or is subjected to reagent 1 time, behind the successive administration 7 days, get blood, measure mouse blood glucose value after the meal from mouse tail vein.Experimental result is carried out statistical treatment, and the result is as follows:
Table 1. pair (α-Fu Nanjiasuan) vanadyl gastric infusion to the influence of blood glucose in diabetic mice (x ± s, n=8)
| Group | Dosage mg/kg | One week of administration before blood sugar (mmol/L) administration | |
| Normal group | Deng appearance NS | ???5.06±0.87 | ????5.26±0.47 |
| The solvent group | Etc. appearance | ??27.72±2.79 | ???26.55±1.87 |
| The VPA group | ???65.8 | ??27.87±2.14 | ???17.49±2.79×× |
| The BMOV group | ???63.2 | ??27.54±2.12 | ???19.88±3.38×× |
| Two (α-Fu Nanjiasuan) vanadyl | ???57.8 | ??27.64±3.45 | ???16.77±3.01×× |
Annotate: * * P＜0.01, compare with the solvent group.
Embodiment 5: preliminary toxicity
Two (α-Fu Nanjiasuan) vanadyl gastric infusion is to the LD of mouse
50For 788.0mg/kg (95% fiducial limit 671.6～924.5mg/kg), the glucose level to normal mouse does not exert an influence simultaneously, in the experiment with 57.8mg/kg.day
-1Dosed administration 7 days, mouse does not show tangible toxicity.
Claims (9)
1. a vanadium compound is characterized in that its molecular formula is C
10H
6O
7V, molecular weight are 289, and structural formula is:
2. method for preparing the described vanadium compound of claim 1 comprises following process steps successively:
A. get a certain amount of α-Fu Nanjiasuan dissolving back adding barium carbonate more excessive slightly and carry out chemical reaction than both ideal response mol ratios,
B. remove by filter barium carbonate, concentrated mother liquor obtains α-Fu Nanjiasuan barium,
C. α-Fu Nanjiasuan barium is mixed with vanadylic sulfate and carries out chemical reaction,
D. remove by filter BaSO
4, concentrated mother liquor obtains green two (α-Fu Nanjiasuan) vanadyl crystallization.
3. vanadium compound preparation method according to claim 2 is characterized in that described α-Fu Nanjiasuan of step a and barium carbonate are reflected at 2: 1.05～mol ratio under carry out 40～60 ℃ of temperature of reaction, 3～5 hours reaction times at 2: 1.10.
4. vanadium compound preparation method according to claim 2 is characterized in that described being concentrated under 50～70 ℃ of step b carry out.
5. vanadium compound preparation method according to claim 2 is characterized in that described α-Fu Nanjiasuan barium of step c and vanadylic sulfate are reflected at 1: 1 and carry out reaction times 2-3 hour under the mol ratio.
6. vanadium compound preparation method according to claim 2 is characterized in that described being concentrated under 40～60 ℃ of steps d carry out.
7. vanadium compound preparation method according to claim 2 is characterized in that the described α-Fu Nanjiasuan barium of step b and d and two (α-Fu Nanjiasuan) vanadyl crystallization recrystallization purification in water.
8. vanadium compound preparation method according to claim 2, it is characterized in that described α-Fu Nanjiasuan of step a and barium carbonate be reflected at 2: 1.05～mol ratio under carry out at 2: 1.10,40～60 ℃ of temperature of reaction, 3～5 hours reaction times, described being concentrated under 50～70 ℃ of step b carried out, described α-Fu Nanjiasuan barium recrystallization in water is purified, described α-Fu Nanjiasuan barium of step c and vanadylic sulfate are reflected at 1: 1 to carry out under the mol ratio, reaction times 2-3 hour, described being concentrated under 40～60 ℃ of steps d carried out, and described two (α-Fu Nanjiasuan) vanadyl crystallizations recrystallization in water is purified.
9. the application of the described vanadium compound of claim 1 in the medicine of preparation treatment diabetes.
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|---|---|---|---|
| CNB001280538A CN1178946C (en) | 2000-11-28 | 2000-11-28 | Vanadium compound and its preparing process and usage |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB001280538A CN1178946C (en) | 2000-11-28 | 2000-11-28 | Vanadium compound and its preparing process and usage |
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| Publication Number | Publication Date |
|---|---|
| CN1355169A true CN1355169A (en) | 2002-06-26 |
| CN1178946C CN1178946C (en) | 2004-12-08 |
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ID=4592931
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101953846A (en) * | 2010-06-24 | 2011-01-26 | 攀枝花兴辰钒钛有限公司 | Application of medicinal composition to preparing medicament for treating diabetes |
| CN101972273A (en) * | 2010-10-29 | 2011-02-16 | 攀枝花兴辰钒钛有限公司 | Application of medicine in preparing medicines for treating diabetes mellitus |
| CN102134738A (en) * | 2010-12-24 | 2011-07-27 | 华东师范大学 | Preparation method of oxalic acid hydroxylamine vanadium coordination compound crystalloid with bioactivity |
| CN103561733A (en) * | 2011-03-07 | 2014-02-05 | Cfm医药控股有限公司 | Use of vanadium compounds for maintaining normaglycemia in a mammal |
| CN103599107A (en) * | 2013-09-03 | 2014-02-26 | 昆明贵金属研究所 | Novel applications of bis(alpha-furancarboxylato)oxovanadium as anticancer medicine |
| CN104447852A (en) * | 2014-11-17 | 2015-03-25 | 云南大学 | Novel schiff base vanadium oxide compound as well as preparation method and application thereof |
| CN107412334A (en) * | 2017-09-06 | 2017-12-01 | 湖北厚品生物科技有限公司 | Compound control sugar mixture and its manufacture method |
-
2000
- 2000-11-28 CN CNB001280538A patent/CN1178946C/en not_active Expired - Fee Related
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101953846B (en) * | 2010-06-24 | 2011-12-28 | 攀枝花兴辰钒钛有限公司 | Application of medicinal composition to preparing medicament for treating diabetes |
| CN101953846A (en) * | 2010-06-24 | 2011-01-26 | 攀枝花兴辰钒钛有限公司 | Application of medicinal composition to preparing medicament for treating diabetes |
| CN101972273A (en) * | 2010-10-29 | 2011-02-16 | 攀枝花兴辰钒钛有限公司 | Application of medicine in preparing medicines for treating diabetes mellitus |
| CN101972273B (en) * | 2010-10-29 | 2011-12-21 | 攀枝花兴辰钒钛有限公司 | Application of medicine in preparing medicines for treating diabetes mellitus |
| CN102134738A (en) * | 2010-12-24 | 2011-07-27 | 华东师范大学 | Preparation method of oxalic acid hydroxylamine vanadium coordination compound crystalloid with bioactivity |
| CN107088202A (en) * | 2011-03-07 | 2017-08-25 | Cfm医药控股有限公司 | Purposes for maintaining normoglycemic vfanadium compound in mammal body |
| CN103561733A (en) * | 2011-03-07 | 2014-02-05 | Cfm医药控股有限公司 | Use of vanadium compounds for maintaining normaglycemia in a mammal |
| CN114177197A (en) * | 2011-03-07 | 2022-03-15 | Cfm医药控股有限公司 | Use of vanadium compounds for maintaining normoglycemia in a mammal |
| CN107088202B (en) * | 2011-03-07 | 2021-11-30 | Cfm医药控股有限公司 | Use of vanadium compounds for maintaining normoglycemia in a mammal |
| CN103599107A (en) * | 2013-09-03 | 2014-02-26 | 昆明贵金属研究所 | Novel applications of bis(alpha-furancarboxylato)oxovanadium as anticancer medicine |
| CN103599107B (en) * | 2013-09-03 | 2015-08-12 | 昆明贵金属研究所 | Two (α-furnancarboxylic acid) vanadyl is as the novelty teabag of cancer therapy drug |
| CN104447852B (en) * | 2014-11-17 | 2017-02-22 | 云南大学 | Schiff base vanadium oxide compound as well as preparation method and application thereof |
| CN104447852A (en) * | 2014-11-17 | 2015-03-25 | 云南大学 | Novel schiff base vanadium oxide compound as well as preparation method and application thereof |
| CN107412334A (en) * | 2017-09-06 | 2017-12-01 | 湖北厚品生物科技有限公司 | Compound control sugar mixture and its manufacture method |
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| Publication number | Publication date |
|---|---|
| CN1178946C (en) | 2004-12-08 |
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