CN102898317A - Organic amino compounds serving as immunopotentiators, metabolic enhancers or roborants and preparation method and use thereof - Google Patents

Organic amino compounds serving as immunopotentiators, metabolic enhancers or roborants and preparation method and use thereof Download PDF

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CN102898317A
CN102898317A CN2012103881543A CN201210388154A CN102898317A CN 102898317 A CN102898317 A CN 102898317A CN 2012103881543 A CN2012103881543 A CN 2012103881543A CN 201210388154 A CN201210388154 A CN 201210388154A CN 102898317 A CN102898317 A CN 102898317A
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ethyl
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organic amine
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amine compound
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CN102898317B (en
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崔恒敏
叶平
李英伦
邹平
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Sichuan Agricultural University
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Abstract

The invention discloses organic amino compounds serving as immunopotentiators, metabolic enhancers or roborants. The structural formula of the compounds is shown in the description. In the formula, (1) R1 is 2-hydroxypropyl, R2 is ethyl, and R3 is ethyl; (2)R1 is 2-hydroxypropyl, R2 is hydrogen, and R3 is isopropyl; (3) R1 is n-butyl, R2 is methyl or ethyl, and R3 is methyl or ethyl; (4) R1 is n-butyl, R2 is hydrogen, and R3 is isopropyl; (5) R1 is p-hydroxy phenyl ethyl, R2 is methyl or ethyl and R3 or methyl or ethyl; or (6)R1 is p-hydroxy phenyl ethyl, R2 is hydrogen and R3 is propyl. The compounds can increase the immunity in organisms, so that the organisms can resist fermentation with viruses, parasites and bacteria; the compounds can help to treat chronic wasting diseases; the compounds can allow organisms to get strength in time and be more tolerating to resist various irritation; and the compounds can be used as metabolic enhancers, roborants and fat metabolic enhancers to reduce blood fat and help users lose weight.

Description

Be used as organic amine compound of immunostimulant, metabolic improver, tonic and its preparation method and application
Technical field
The present invention relates to the compound applied technical field, in particular a kind of organic amine compound that is used as immunostimulant, metabolic improver, tonic and its preparation method and application.
Background technology
Virus can cause the multiple infectious disease of people and various domestic animals and fowls, epiphytotics generation, and its disease that causes is many far beyond other microorganism as a kind of pathogenic microorganism.For human, common acute respiratory infection 90%-95% is caused by virus.Show that according to pertinent data virus is caused a disease and accounted for human infectious disease's 70%-80%.Such as common influenza, mumps, infectious hepatitis, viral enteritis, viral myocarditis, epidemic encephalitis type B, epidemic hemorrhagic fever, zoster, measles and AIDS etc., all be due to the virus.Virus can also be integrated into host cell with the autogene group, is the cause of disease of some tumour.New virus is also constantly producing and is occurring, and virus originally is easy to again morph, and along with the variation of self, can cause new various disease again.The disease that present virus causes has strong, the popular wide model of infectivity, case fatality rate high mostly.Such as " coronavirus atypical pneumonia ", the highly pathogenic H5N1 bird flu, the variation swine influenza virus that broke out in recent years, hand foot mouth disease, " tick is stung disease " etc. have been caused human fear.
Virus is very harmful to body, and the disease that virus causes usually is heavy in hand, or even fatal.Behind the Virus entry body, in the permissive cell at invasion position, breed rapidly first, and to closing on diffusion in cell and the tissue, cause the local infection focus.In case virus is not suppressed, virus namely enters in lymphocyte and the mononuclear phagocyte system by blood breeds, and destroys immunity system and reduces immunizing power, and again invade each organ-tissue of whole body by blood, causes various pathologies, thereby various clinical symptom occur.Virus easily causes various types of many cause of diseases polyinfections to immune interference and destruction, relatively typical as: human AIDS; The breeding of pig and respiratory syndrome (blue otopathy), II type PCV-II, Mild type HC, they grow in lymphsystem, badly damaged immunity of organisms; The infectious bursal disease of poultry, Marek, avian leukosis, fowl RE hyperplasia disease, chicken infectious anemia etc. are to damage immunity of organisms equally, cause serious production loss.
The development of antibiotic research makes a lot of bacteriosises be easy to control, and virus just becomes unprecedented outstanding cause of disease.In a century in the past, struggle with virus infection from two approach.The one, the development vaccine comprises deactivation vaccine, weak malicious seedling, subunit seedling etc., makes body produce in advance antibody, the prevention poisoning intrusion, but some viruses so can be invaded body lower of the situation of having made vaccine; The 2nd, development specificity antivirus medicine, this makes progress always very slow on the one hand.Past 30 Years is to the research explanation of mammalian virus, virus strictly parasitizes in the cell, rely on the host cell enzyme system to breed, medicine is difficult to enter cell on the one hand, on the other hand in the viral metabolic process of impact simultaneously, may also disturb the normal cell metabolic process, medicine is difficult to reach efficient specificity, and side effect is little again.Virus also may enter host cell with gene integration, hides for a long time, reactivates under certain condition, and the variability of virus also is higher than bacterium in addition, and these have all strengthened the difficulty of antiviral research.
In any case, the alternative antiviral drug of clinical medicine is considerably less now, drug effect neither be very definite, existing antiviral such as Aminodiamantane, iodoxuridine, virazole, acyclovir, sulfated polysaccharides etc., the infection that basically can not solve the ubiquitous reproductive and respiratory syndrome virus of current swinery, PCV-II and Pestivirus suis.Above-mentioned virus causes the sub-health status of swinery, causes polytype bacillary secondary infection, causes a large amount of direct economic losses, and is high such as sow miscarriage, piggy mortality ratio height, swine growth degradation, swinery stress reaction.
Before the high-efficiency broad spectrum antiviral drug was not invented, we improved body physical efficiency and immunizing power by the enhancing body resistance against diseases, were another strategies that better solves the virus infection problem.But for now, can effectively promote the medicine of immunity of organisms seldom, Western medicine only has several, and great majority are Chinese medicine, but Chinese medicine generally needs long-term prescription just to produce effect, so it is extremely urgent to study broad-spectrum high-efficiency and low-toxicity medicament for immunity enhancement of new generation.
Summary of the invention
The present invention obtains the new organic amine compound of a class with the method for chemosynthesis, experimental results show that this compounds has following pharmacological action and application: (1) immunity of organism enhancement; (2) help body disease-resistant poison, parasite, bacterium to infect the chronic wasting disease assisting therapy after immunity of organism strengthens; (3) the body physical efficiency is replenished and the endurance enhancement; (4) anti-various stress reactions; (5) organism metabolism promotor, tonic; (6) metabolism of fat promotor can be used for reducing blood-fat, fat-reducing.
A kind of organic amine compound as immunostimulant, metabolic improver, tonic, its structural formula is as follows:
Figure BDA0000224969351
Be liquid under the normal temperature, can with sour salify, be solid crystals behind the salify;
(1) R 1Be the 2-hydroxypropyl; R 2Be ethyl; R 3Be ethyl;
(2) R 1Be the 2-hydroxypropyl; R 2Be hydrogen; R 3Be sec.-propyl;
(3) R 1Be normal-butyl; R 2Be methyl or ethyl; R 3Be methyl or ethyl;
(4) R 1Be normal-butyl; R 2Be hydrogen; R 3Be sec.-propyl;
(5) R 1Be the para hydroxybenzene ethyl; R 2Be methyl or ethyl; R 3Be methyl or ethyl;
(6) R 1Be the para hydroxybenzene ethyl; R 2Be hydrogen; R 3Be sec.-propyl.
Described organic amine compound describedly comprises hydrochloric acid, sulfuric acid, acetic acid, citric acid, succsinic acid, Succinic Acid, Whitfield's ointment, paraacetaminobenzoic acid for the used acid of salify.
The application of described organic amine compound, preparation immunostimulant, antiviral, metabolic improver, tonic, reducing blood-fat, the human drugs of weight losing function and the application in the healthcare products.
The application of described organic amine compound, preparation immunostimulant, antiviral, metabolic improver, the medicine for animals of tonic function and the application in the healthcare products.
The application of described organic amine compound, the fishing of preparation immunostimulant, antiviral, metabolic improver, tonic function is with the application in medicine and the healthcare products.
This compounds can be developed into the medicine of the relevant pharmacological action that is applied to the mankind, Mammals, hydrocoles etc., healthcare products.
Pharmacological experiment proves: this product can improve body specificity and non-specific immunity simultaneously; Promote human body energy metabolism and mobile, promote inose to utilize first the decomposition, be conducive to synthesizing and storage of ATP; Can increase the physical efficiency load of body, the stress reaction under the anti-various environment unfavourable condition; The antivirus action of this product is not direct virus replication, but realizes resisting poisoning intrusion and and breeding by enhancing body specificity and non-specific immunity.
A further object of the invention provides the application of this organic amine compound in people's medicine and human healthcare products.
A further object of the invention provides the application of this organic amine compound in veterinary drug and animal health product.
A further object of the invention provides the application of this organic amine compound in the fishing medicine.
Compared with prior art, the present invention has following advantage:
(1) carboxylate salt of this organic amine compound, can be added in cultivated animals (pig, rabbit, cattle and sheep, poultry, the fishes and shrimps etc.) feed, can strengthen the immunological competence of cultivated animals, improve resistance against diseases, make the few sick few medication of cultivated animals, replace the antibiotic interpolation of part to use, improve the animal product quality, reduce antibiotic remains in the product.
(2) carboxylate salt of this organic amine compound can be added in cultivated animals (pig, rabbit, cattle and sheep, poultry, the fishes and shrimps etc.) feed, promotes the cultivated animals growth, improve food conversion ratio, improve breeding performonce fo animals, reduced production cost, improved fanning economics.
(3) this organic amine compound has certain antiobesity action, reduces blood cholesterol and blood fat, promotes body fat to decompose, and exploit person has potentiality with reducing blood-fat, the relevant medicine of fat-reducing and healthcare products.
Description of drawings
Fig. 1 is 1-diethylin-2-propyl alcohol 1The H-NMR spectrum;
Fig. 2 is 1-diethylin-2-propyl alcohol 13The C-NMR spectrum;
Fig. 3 is the sec.-propyl n-butylamine 1The H-NMR spectrum;
Fig. 4 is the sec.-propyl n-butylamine 13The C-NMR spectrum;
Fig. 5 is the 4-(2-isopropylamino) ethylphenol 1The H-NMR spectrum;
Fig. 6 is the 4-(2-isopropylamino) ethylphenol 13The C-NMR spectrum;
Embodiment
The specific embodiment that provides below in conjunction with the contriver further specifies beneficial effect and the application of organic amine compound of the present invention.
Embodiment 1
Structure for reagent product sec.-propyl n-butylamine is as follows:
Figure BDA0000224969352
The isolated perfusion experiment of the frog heart and the mouse heart
For reagent product: sec.-propyl n-butylamine and paraacetaminobenzoic acid 1:1(mol ratio, lower same) organic amine salt of salify.
The frog heart and mouse core are made the ventricle perfusion that exsomatizes, with the pollex of polygraph record ventricular muscles, 0.05% organic slat solution has cardiotonic, and it is more obvious to increase cardiotonic with test solution concentration, and (5%) also is safe to heart under the high density, does not suppress the pollex of heart.
The experiment of rabbits infestines motion
Supply the reagent product: the organic amine salt of sec.-propyl n-butylamine and paraacetaminobenzoic acid 1:1 salify.
The rabbits infestines preparation places the maxwell bath cup, with the wriggling of polygraph record myenteron, the Tai Shi solution that contains 0.05% organic amine salt has the effect that strengthens the unstriated muscle wriggling, and myenteron wriggling strength and amplitude increase, the wriggling time obviously prolongs, but peristalsis frequency does not significantly increase.
The hungry endurance experiment of small white mouse
Supply the reagent product: the organic amine salt of sec.-propyl n-butylamine and paraacetaminobenzoic acid 1:1 salify.
Small white mouse stops to throw in food, freely drinks the 0.1% organic amine salt aqueous solution, can strengthen the ability of the anti-hunger of small white mouse, increases the survival time, and this effect is decomposed the energy supply realization by accelerating body fat.
The obese rat model is set up and weight-reducing experiment
Supply the reagent product: the organic amine salt of sec.-propyl n-butylamine and paraacetaminobenzoic acid 1:1 salify.
By giving the nutritional imbalance diet of the high fat high calorie of rat, set up obese model, obese rat is freely drunk the 0.1% organic amine salt aqueous solution, proves to have obvious antiobesity action.
Small white mouse physical efficiency Enhancement test
Supply the reagent product: the organic amine salt of sec.-propyl n-butylamine and paraacetaminobenzoic acid 1:1 salify.
Small white mouse is freely drunk the 0.1% organic amine salt aqueous solution, and the time of drinking is a week, can prolong small white mouse frozen water swimming time.
Small white mouse cold-hot stress tests
Supply the reagent product: the organic amine salt of sec.-propyl n-butylamine and paraacetaminobenzoic acid 1:1 salify.
Small white mouse is freely drunk the 0.1% organic amine salt aqueous solution, and the time of drinking is a week.Small white mouse is placed respectively 42 ℃, and 5 ℃ of environment have the mouse of raising opposing cold stress, and the heat stress effect prolongs mouse in the survival time of extreme environment.
The Breeding of Broiler Chicks experiment
Supply the reagent product: the organic amine salt of sec.-propyl n-butylamine and paraacetaminobenzoic acid 1:1 salify.
One monthly age broiler chicken is divided into blank group and experimental group.Experimental group contains in the experimental group feed for reagent product 0.1% with for reagent product spice, and other system component of feed is consistent.Feeding time is one month, and two monthly age broiler chicken are weighed, broiler growth and efficiency of feed utilization during the experiment with computing.Experimental results show that for the reagent product and can improve broiler growth rate 11.3%, improve efficiency of feed utilization 9.4%.
The pigling immunity determination experiment
Supply the reagent product: the organic amine salt of sec.-propyl n-butylamine and paraacetaminobenzoic acid 1:1 salify.
60 age in days piglets with for reagent product spice, contain in the feed for reagent product 0.1%, and feeding time is one month, measure body fluid and the cellular immunity of pig during 90 age in days.Experimental results show that can improve body antibody for the reagent product produces ability (improving associated antibodies molecular amounts in the blood, the antibody response the level rise), can improve macrophage in body phagocytic activity (carbon clearance experiment) simultaneously.
Embodiment 2
Synthesizing of 1-diethylin-2-propyl alcohol:
Figure BDA0000224969353
Synthetic method: the diethylamine that in the 250mL four-hole boiling flask that agitator, reflux condensing tube and two dropping funnels are housed, adds 0.2mol, under heating in water bath, slowly drip the 1-chloro-2-propanol of 0.1mol, drip again 40% aqueous sodium hydroxide solution 20ml, control total time for adding 2h, then boiling reflux 1h cools off to get thick product.Filtering sodium-chlor, the filtrate standing demix, water phase separated and organic phase, water extracted with diethyl ether 3 times, extraction liquid and organic phase merge, dried overnight.The distillation of filtering siccative obtains product.
With reference to figure 1 and Fig. 2, structured data: 1H-NMR (400MHz, CDCl 3) δ 1.0(m, 9H) 2.4(t, 4H) 2.6(d, 1H) 3.4(m, 1H) 4.8(s, 1H); 13C-NMR (400MHz, CDCl 3) δ 13.3(2C) 21.7(1C) 47.7(2C) 61.5(1C) 66.5(1C).
Embodiment 3
Synthesizing of sec.-propyl n-butylamine:
Figure BDA0000224969354
Synthetic method: the isopropylamine that in the 250mL four-hole boiling flask of agitator, reflux condensing tube and dropping funnel is housed, adds 0.2mol, under heating in water bath, slowly drip the 1-n-butyl bromide of 0.1mol, drip again 40% aqueous sodium hydroxide solution 20ml, control total time for adding 2h, then boiling reflux 1h cools off to get thick product.Filtering sodium-chlor, the filtrate standing demix, water phase separated and organic phase, water extracted with diethyl ether 3 times, extraction liquid and organic phase merge, dried overnight.The distillation of filtering siccative obtains product.
With reference to figure 3 and Fig. 4, structured data: 1H-NMR (400MHz, CDCl 3) δ 0.9(t, 3H) 1.1(d, 6H) 1.3(m, 4H) 2.0(s, 1H) 2.5(t, 2H) 3.0(m, 1H); 13C-NMR (400MHz, CDCl 3) δ 13.8(1C) 20.1(1C) 23.7(2C) 61.5(1C) 33.0(1C) 46.8(1C) 48.7(1C).
Embodiment 4
The 4-(2-isopropylamino) ethylphenol is synthetic
Figure BDA0000224969355
Synthetic method: the isopropylamine that in the 250mL four-hole boiling flask of agitator, reflux condensing tube and dropping funnel is housed, adds 0.2mol, the 4-(2 ' of slow adding 0.1mol-chlorine under heating in water bath) ethylphenol, drip again 40% aqueous sodium hydroxide solution 20ml, control total time for adding 2h, then boiling reflux 1h, separate out solid after the cooling, suction filtration gets thick product.Obtain product with the appropriate solvent recrystallization.
With reference to figure 5 and Fig. 6, structured data: 1H-NMR:(400MHz, CDCl 3), δ 1.1(d, 6H) 2.0(s, 1H) 2.7(t, 2H) 2.8(t, 2H) 3.0(m, 1H) 6.9(q, 4H) 9.4(s, 1H)
13C-NMR:(400MHz,CDCl 3),δ23.7(2C) 35.9(1C) 48.7(2C) 115.8(2C) 128.1(1C) 130.2(2C) 155.7(1C)
Should be understood that, for those of ordinary skills, can be improved according to the above description or conversion, and all these improvement and conversion all should belong to the protection domain of claims of the present invention.

Claims (6)

1. organic amine compound as immunostimulant, metabolic improver, tonic is characterized in that its structural formula is as follows:
Figure FDA0000224969341
Be liquid under the normal temperature, can with sour salify, be solid crystals behind the salify;
(1) R 1Be the 2-hydroxypropyl; R 2Be ethyl; R 3Be ethyl;
(2) R 1Be the 2-hydroxypropyl; R 2Be hydrogen; R 3Be sec.-propyl;
(3) R 1Be normal-butyl; R 2Be methyl or ethyl; R 3Be methyl or ethyl;
(4) R 1Be normal-butyl; R 2Be hydrogen; R 3Be sec.-propyl;
(5) R 1Be the para hydroxybenzene ethyl; R 2Be methyl or ethyl; R 3Be methyl or ethyl;
(6) R 1Be the para hydroxybenzene ethyl; R 2Be hydrogen; R 3Be sec.-propyl.
2. organic amine compound as claimed in claim 1 is characterized in that, described organic amine compound describedly comprises hydrochloric acid, sulfuric acid, acetic acid, citric acid, succsinic acid, Succinic Acid, Whitfield's ointment, paraacetaminobenzoic acid for the used acid of salify.
3. the application of organic amine compound as claimed in claim 1 or 2 is characterized in that, preparation immunostimulant, antiviral, metabolic improver, tonic, reducing blood-fat, the human drugs of weight losing function and the application in the healthcare products.
4. the application of organic amine compound as claimed in claim 1 or 2 is characterized in that, preparation immunostimulant, antiviral, metabolic improver, the medicine for animals of tonic function and the application in the healthcare products.
5. the application of organic amine compound as claimed in claim 1 or 2 is characterized in that, the fishing of preparation immunostimulant, antiviral, metabolic improver, tonic function is with the application in medicine and the healthcare products.
6. structural molecule as claimed in claim 1 or 2 is characterized in that, describedly comprises hydrochloric acid, sulfuric acid, acetic acid, citric acid, succsinic acid, Succinic Acid, Whitfield's ointment, paraacetaminobenzoic acid for the used acid of salify.
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