CN100348577C - Medicinal compound and anthelminthic application - Google Patents
Medicinal compound and anthelminthic application Download PDFInfo
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- CN100348577C CN100348577C CNB2004100182542A CN200410018254A CN100348577C CN 100348577 C CN100348577 C CN 100348577C CN B2004100182542 A CNB2004100182542 A CN B2004100182542A CN 200410018254 A CN200410018254 A CN 200410018254A CN 100348577 C CN100348577 C CN 100348577C
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- histozoic
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- biliary tract
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 12
- 230000000507 anthelmentic effect Effects 0.000 title description 4
- 244000045947 parasite Species 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 11
- 241000243777 Trichinella spiralis Species 0.000 claims abstract description 10
- 229940096911 trichinella spiralis Drugs 0.000 claims abstract description 9
- 210000003445 biliary tract Anatomy 0.000 claims abstract description 8
- 241001327965 Clonorchis sinensis Species 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 6
- LIWZHTNKADMXKZ-UHFFFAOYSA-N C(CCC(=O)O)(=O)O.C1(=CC=CC=C1)CC(=N)N(C)C Chemical compound C(CCC(=O)O)(=O)O.C1(=CC=CC=C1)CC(=N)N(C)C LIWZHTNKADMXKZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 241000244206 Nematoda Species 0.000 claims abstract description 5
- 230000000968 intestinal effect Effects 0.000 claims abstract description 4
- 241001465677 Ancylostomatoidea Species 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 241000242722 Cestoda Species 0.000 claims description 5
- 241001126260 Nippostrongylus Species 0.000 claims description 5
- 239000000921 anthelmintic agent Substances 0.000 claims description 3
- 230000003071 parasitic effect Effects 0.000 claims 2
- 241001465754 Metazoa Species 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 7
- 229940079593 drug Drugs 0.000 abstract description 5
- 238000010171 animal model Methods 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 230000003285 pharmacodynamic effect Effects 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- -1 amino-benzene amidine compound Chemical class 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 238000007689 inspection Methods 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000001384 succinic acid Substances 0.000 description 4
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 3
- 241000283707 Capra Species 0.000 description 3
- 208000030852 Parasitic disease Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000699800 Cricetinae Species 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- 230000029087 digestion Effects 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 210000004013 groin Anatomy 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000012716 precipitator Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- 238000002255 vaccination Methods 0.000 description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- 208000007743 Acute Abdomen Diseases 0.000 description 1
- 241000244203 Caenorhabditis elegans Species 0.000 description 1
- 101100391174 Dictyostelium discoideum forC gene Proteins 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 102000057297 Pepsin A Human genes 0.000 description 1
- 108090000284 Pepsin A Proteins 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 244000046109 Sorghum vulgare var. nervosum Species 0.000 description 1
- 208000031320 Teratogenesis Diseases 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 241000243774 Trichinella Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229960002669 albendazole Drugs 0.000 description 1
- HXHWSAZORRCQMX-UHFFFAOYSA-N albendazole Chemical compound CCCSC1=CC=C2NC(NC(=O)OC)=NC2=C1 HXHWSAZORRCQMX-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000012443 analytical study Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 244000144980 herd Species 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960003439 mebendazole Drugs 0.000 description 1
- BAXLBXFAUKGCDY-UHFFFAOYSA-N mebendazole Chemical group [CH]1C2=NC(NC(=O)OC)=NC2=CC=C1C(=O)C1=CC=CC=C1 BAXLBXFAUKGCDY-UHFFFAOYSA-N 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- VEHZLOXNVVKFAG-UHFFFAOYSA-N n,n-dimethyl-2-phenylethanimidamide Chemical compound CN(C)C(=N)CC1=CC=CC=C1 VEHZLOXNVVKFAG-UHFFFAOYSA-N 0.000 description 1
- 210000003928 nasal cavity Anatomy 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 239000002297 parasiticide Substances 0.000 description 1
- 230000024241 parasitism Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 229940111202 pepsin Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention relates to a medicinal compound of which the chemical name is N'-(4-amido) phenyl N, N-dimethyl acetamidine succinate, and the chemical structural formula of the medicinal compound is the formula disclosed in the specification. The present invention not only has good curative effects on expelling intestinal nematode but also has very excellent curative effects on curing the food-borne parasites of histozoic parasites (trichinella spiralis) and biliary tract parasites (clonorchis sinensis). Animal experiments show that the parasite expelling rate of the present invention is obviously better than that of the existing clinical medication.
Description
Technical field
The present invention relates to field of medicaments, particularly a kind of medicinal compound and can prepare the purposes of anthelmintic drug.
Background technology
Enterozoa is to colonize in enteron aisle or the caused disease of digestion organs, establishes a capital at the enteron aisle parasitism because each growth period of Enterozoa differs, and therefore, causes that pathology just is not limited to enteron aisle.The harm of parasitosis is a large amount of nutrition of predation human body, the material that is produced after the polypide metabolism can mechanically damage tissue and function, therefore, expelling parasite is having extremely long-pending meaning aspect the raising human life quality, the insect repellent of at present using often clinically is Vermox and albendazole, though the anthelmintic action of these two kinds of medicines is stronger, but they can cause the roundworm migration, cause insect to get out or cause acute abdomen such as biliary tract ascarid from patient's mouth or nasal cavity, and such medicine is to the Salmonella reversion test teratogenesis that has been positive, and reason is due to its benzimidazolyl structure.
Scientists has been carried out a large amount of research for seeking novel non-benzimidazolyl class medicine at present, because the amino-benzene amidine compound has the effect of driving Enterozoa, Woll Weber in 1971 etc. have synthesized first phenalgin amidine (amides), referring to German patent DE 2029293 (1971), DE2346939 (1975); Nineteen eighty-three Yao Run China, Chen Yaoqing etc. have synthesized triphenyl diamidine (Xue husband alkali class), referring to Chinese patent CN96116360.7 (1996), CN96116469.7 (1996).But these medicines can not be fully up to expectations to the result of treatment of histozoic (Trichinella spiralis) and biliary tract parasite (clonorchis sinensis), and clinically this two classes parasite is also lacked specific medicament at present.
Summary of the invention
The inventor is carrying out behind the structure activity study above-mentioned two compounds, has synthesized amino benzene carbon amidine organic acid salt compound and has found that it has very strong wide spectrum anthelmintic action.
So the objective of the invention is to overcome the defective of prior art, a kind of novel medicinal compound be provided.
The chemical name of above-mentioned medicinal compound is: N '-(4-amino) phenyl N, and N-dimethyl ethanamidine succinate, its chemical structural formula is:
Above-mentioned medicinal compound is intermediate product N '-(4-amino) the phenyl N by synthetic triphenyl diamidine among the Chinese patent CN96116360.7 in fact, and N-dimethyl ethanamidine (its preparation is referring to the embodiment 1-2 of above-mentioned patent) reacts the xln that obtains with Succinic Acid in suitable organic solvent.
In one embodiment of this invention, with N '-(4-amino) phenyl N, N-dimethyl ethanamidine is dissolved in the acetone soln, react with the mixing solutions of Succinic Acid and organic solvent, and the salt crystal that obtains behind the recrystallization.
Wherein, can be dehydrated alcohol, ethyl acetate etc. with Succinic Acid blended organic solvent.
Another object of the present invention then provides the purposes of this medicinal compound in the preparation anthelmintic drug.It has all well and good curative effect except driving away intestinal nematodes such as Brazilian Nippostrongylus, American hookworm and tapeworm, especially histozoic (Trichinella spiralis) and this class food source property parasite of biliary tract parasite (clonorchis sinensis) there is very strong therapeutic action, so tool wide spectrum anthelminthic effect; And laboratory animal shows that its deworming rates obviously is better than existing clinical application.
Embodiment
Embodiment 1 N '-(4-nitro) phenyl N, the preparation of N-dimethyl ethanamidine (referring to the embodiment 1 of CN96116360.7)
Take by weighing p-Nitroaniline 41.4 grams (0.3 mole), N,N-DIMETHYLACETAMIDE 30.5 grams (0.35 mole) and 100 milliliters of toluene place three-necked bottle, under agitation drip phosphorus oxychloride 15.3 grams (0.1 mole) and finish the post-heating backflow 3-5 hour, boil off solvent under the decompression, in the residue impouring frozen water, slowly add the liquid caustic soda of 30% concentration, transfer pH to 8-9, solid is separated out, and filters, washing, oven dry, ethyl alcohol recrystallization gets 66 grams, productive rate 90%, fusing point 94-96 ℃.
Embodiment 2 N '-(4-amino) phenyl N, the preparation of N-dimethyl ethanamidine (referring to the embodiment 2 of CN96116360.7)
Tin protochloride (SnCl
22H
2O) 90 grams (0.4 mole) are put in the three-necked bottle, add 180 milliliters of concentrated hydrochloric acids, slowly be warming up to 50 ℃, stir down, with N '-(4-nitro) phenyl N of the embodiment 1 of 38.6 grams (0.2 mole), N-dimethyl ethanamidine divides 5 addings, finish the back in 40-80 ℃ of insulation 2-5 hour, under cooling, splash into 30%NaOH, regulate pH to 10-12 ethyl acetate extraction, anhydrous Na
2SO
4Drying, vinyl acetic monomer is removed in decompression, and recrystallization gets 28.5 grams, productive rate 80%, fusing point 92-93 ℃.
Embodiment 3 N '-(4-amino) phenyl N, the preparation of N-dimethyl ethanamidine succinate
3.54 N '-(4-amino) phenyl N of gram (0.02 mole), N-dimethyl ethanamidine adds 100 milliliters of acetone and places flask together, stirring at room half an hour, drips 2.36 gram Succinic Acid (0.02 mole) and 100 milliliters of solution that dehydrated alcohol is made into, temperature of reaction 30-70 ℃, be incubated 2 hours, separate out fine needle crystal after the reaction cooling, filter, dry, get 3.2 grams, use the dehydrated alcohol recrystallization, 136-138 ℃ of product fusing point.
The N ' of secondary recrystallization-(4-amino) phenyl N, N-dimethyl ethanamidine succinate sample is through ultimate analysis, infrared spectra, UV spectrum, proton nmr spectra and carbon spectrum and mass spectral instrumental analysis, and to its spectrum analysis, draw the content of element, the molecular weight of mass spectrum prompting is all in N ' shown in us-(4-amino) phenyl N, the theoretical numerical value unanimity of the chemical structure of N-dimethyl ethanamidine succinate, the distinctive group absorption peak of its structure also obtain authentication at infrared spectra, UV spectrum and proton nmr spectra and carbon spectrum.
Ultimate analysis (seeing the following form):
Molecular formula: C
14H
21N
3O
4Molecular weight: 295
| Analysis project | Analytical results (%) | Theoretical value (%) | |||
| 1 | 2 | 3 | 4 | ||
| C | 56.91 | 56.90 | 56.77 | 56.64 | 56.95 |
| H | 7.18 | 7.18 | 7.07 | 7.13 | 7.12 |
| N | 14.07 | 14.11 | 14.24 | 14.24 | 14.24 |
Annotate: 1,2 is Shanghai Institute of Pharmaceutical Industry's synthetic drugs research department measured result in upward showing; 3,4 is the analytical study result of Shanghai Organic Chemistry Institute, Chinese Academy of Sciences.
' H NMR:7.20 (dj, 2H, benzene H), 6.28 (dj, 2H, benzene H), 3.16-3.22 (2s, 6H, N (CH
3)
2), 2.40-2.41 (d, 4H-CH
2-CH
2-), 2.08 (s, 3H ,=C-CH
3). IR:3313,3207 (w=C--CH
3), 1645 (s, C=N.C=O) .1521 (s, C
6H
5-) .1409 (m..NCH
3).
MS：m/z(％)177(M
+，66.49)，133(M
+，100)，92(M
+，66.20)：AnalCalcd.forC
14H
21.O
4N
3：：C56.95，H7.12，N14.24：found C56.77，H7.07，N14.24
Experimental example 1 is driven away Brazilian Nippostrongylus pharmacodynamics test
Animal, body weight, animal model: the SD rat is available from west, Shanghai pul-Bi Kai laboratory animal company limited, card SCXK (Shanghai) 2003-0002, body weight 60-70 gram, female, hero half and half, experimental animal model are that Prevention ﹠ Control Station of Parasitic Disease, China Diseases Prevention ﹠ C plants so far in nineteen sixty introduction guarantor.
1) method and step: every mouse is from 300 of groin subcutaneous vaccination period of infection Brazil Nippostrongylus larvas, injection capacity 0.15ml, inoculate administration after 12 days, after administration, collected whole ight soil of each mouse respectively in 24 hours, 48 hours, wash precipitator method inspection worm counting with water.
2) efficacy assessment index:
3) test-results: infected rats is once irritated the deworming rates that stomach awards 8mg/kg and 16mg/kg and is respectively 90.8% and 100%.
Experimental example 2 is driven away American hookworm animal pharmacodynamics test
Animal, body weight, animal model: Syria hamster is available from Shanghai Vaccine and Serum Institute's Experimental Animal Center, card number is SCXK (Shanghai) 2002-0029, body weight 60-70 gram, male and female half and half, to be Prevention ﹠ Control Station of Parasitic Disease, China Diseases Prevention ﹠ C set up in 1974 hamster-American hookworm model, protects kind so far.
1) method and step: every mouse infects 250 of American hookworm larvas from the groin subcutaneous vaccination, injection capacity is 0.15ml, inoculate after 49 days and do the excrement inspection with the saturated brine floating method, get positive mouse administration, whole ight soil of collecting each mouse after administration in 24 hours, 48 hours respectively wash precipitator method inspection worm counting with water.
2) efficacy assessment index:
3) experimental result: the deworming rates that the infection hamster is once irritated stomach 50mg/kg and 100mg/kg is respectively 84.7% and 97.8%.
Experimental example 3 is driven away the pharmacodynamics test of tapeworm
Laboratory animal: the goat that Chinese sorghum village, Ta Ha township, Fuyu County, Heilongjiang Province herds naturally, excrement are examined every gram faecal egg number＞200, body weight 15-50kg.
1) efficacy assessment index:
2) test-results: infecting once the take medicine tapeworm negative conversion rate of 20mg/kg of goat is 80%.
Experimental example 4 treatment clonorchis sinensis pharmacodynamics tests
Experimental animal: it is that the cavy mouth is raised 100 of clonorchis sinensis capsule childrens that Britain plants, the mouse administration that the excrement inspection is positive after 25 days.
1) efficacy assessment index:
2) experimental result: when infecting cavy administration total dose 72mg/kg, 90mg/kg and 120mg/kg, worm reduction rate is respectively 93.1%, 93.7% and 100%.
The pharmacodynamics test of experimental example 5 treatment Trichinella spiraliss
Laboratory animal: Kunming strain mouse (20 ± 1g), every mouse on an empty stomach mouth raise trichinella larvae, 300 of adult groups, 100 (gastric pepsin digestion method) of larva group.
2) test-results:
Dosage be 10mg/kg to the enteron aisle Trichinella spiralis excystation phase larva worm reduction rate, negative conversion rate be 100%.
To be 20mg/kg and 30mg/kg be respectively 91.0% and 97.1% to the worm reduction rate of enteron aisle Trichinella spiralis adult to dosage.
Total dose 70mg/kg and 140mg/kg are respectively 78.2% and 86.9% to the worm reduction rate of muscle Trichinella spiralis stage of invasion larva.
Total dose 70mg/kg and 140mg/kg are respectively 83.7% and 96.7% to the worm reduction rate of muscle Trichinella spiralis encystation phase larva.
By above-mentioned experimental example as can be known, N ' of the present invention-(4-amino) phenyl N, N-dimethyl ethanamidine succinate is through the research of pharmacodynamics, the result shows that its parasiticide has the characteristics of wide spectrum, the Enterozoa (Brazilian Nippostrongylus, American hookworm etc.) of animal infection modal and the goat of herding infection such as multiple gastrointestinal nematode, tapeworm are naturally all had expeling effect preferably and therapeutic action, and its used drug dose is less than present clinical application; And N ' of the present invention-(4-amino) phenyl N, N-dimethyl ethanamidine succinate also has reasonable expeling effect and therapeutic action to histozoic (Trichinella spiralis), biliary system parasite (clonorchis sinensis).
Claims (5)
1, a kind of medicinal compound N '-(4-amino) phenyl N, N-dimethyl ethanamidine succinate, its chemical structural formula is:
2, medicinal compound according to claim 1 can be driven away histozoic or the parasitic anthelmintic drug of biliary tract in preparation, perhaps can drive away the application in the parasitic broad-spectrum de-worming medicine thing at least two positions in intestinal nematodes, histozoic and the biliary tract parasite.
3, application according to claim 2 is characterized in that this intestinal nematodes is Brazilian Nippostrongylus, American hookworm and/or tapeworm.
4, application according to claim 2 is characterized in that this histozoic is a Trichinella spiralis.
5, application according to claim 2 is characterized in that this biliary tract parasite is a clonorchis sinensis.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100182542A CN100348577C (en) | 2004-05-12 | 2004-05-12 | Medicinal compound and anthelminthic application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100182542A CN100348577C (en) | 2004-05-12 | 2004-05-12 | Medicinal compound and anthelminthic application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1696108A CN1696108A (en) | 2005-11-16 |
| CN100348577C true CN100348577C (en) | 2007-11-14 |
Family
ID=35349022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004100182542A Expired - Fee Related CN100348577C (en) | 2004-05-12 | 2004-05-12 | Medicinal compound and anthelminthic application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100348577C (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2029299A1 (en) * | 1970-06-13 | 1971-12-30 | Farbenfabriken Bayer Ag, 5090 Leverkusen | New aminophenylamidines, processes for their production and their use as pharmaceuticals |
| CN1150147A (en) * | 1995-11-16 | 1997-05-21 | 山东新华医药集团有限责任公司 | Process for preparing N-(2 or 3-M, 5 or 6-M', 4-amino-phenyl)-N',N'-dimethyl acetamidine |
-
2004
- 2004-05-12 CN CNB2004100182542A patent/CN100348577C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2029299A1 (en) * | 1970-06-13 | 1971-12-30 | Farbenfabriken Bayer Ag, 5090 Leverkusen | New aminophenylamidines, processes for their production and their use as pharmaceuticals |
| CN1150147A (en) * | 1995-11-16 | 1997-05-21 | 山东新华医药集团有限责任公司 | Process for preparing N-(2 or 3-M, 5 or 6-M', 4-amino-phenyl)-N',N'-dimethyl acetamidine |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1696108A (en) | 2005-11-16 |
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