CN100428930C - Application of p-hydroxybenzoic acid and its analogue in the preparing process of medicine for preventing and treating skin mucous membrane virus infection - Google Patents
Application of p-hydroxybenzoic acid and its analogue in the preparing process of medicine for preventing and treating skin mucous membrane virus infection Download PDFInfo
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- CN100428930C CN100428930C CNB2005100122885A CN200510012288A CN100428930C CN 100428930 C CN100428930 C CN 100428930C CN B2005100122885 A CNB2005100122885 A CN B2005100122885A CN 200510012288 A CN200510012288 A CN 200510012288A CN 100428930 C CN100428930 C CN 100428930C
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0034—Urogenital system, e.g. vagina, uterus, cervix, penis, scrotum, urethra, bladder; Personal lubricants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0043—Nose
Abstract
The invention discloses an application of p-hydroxybenzoic acid and analogue in the skin virus infection drug, which is characterized by the following: fitting for infectious drug of people breast tumour virus and herpetoviridae virus; allocating each auxiliary material to prepare different agent or personal nursing product.
Description
Technical field
The present invention relates to the application in preparation prevention and treatment skin and mucosa infection medicine of P-hydroxybenzoic acid and analog thereof.Or rather, relate to the application in preparing prevention and treatment humans and animals skin mucosa human papillomavirus, herpesvirus infection medicine of P-hydroxybenzoic acid and analog thereof.
Background technology
2 hydroxybenzoic acid (salicylic acid) has been used to treat the antibacterial and the fungal infectious disease of skin mucosa.P-hydroxybenzoic acid and ester thereof are as the antiseptic of food, medicine.Gallic acid (promptly 3,4,5-trihydroxybenzoic acid) usually is used for antioxidant, and being proved to be has inhibitory action (Guangzhou medical science higher junior college of PLA journal, 1998,26 (2): 5-7) to hepatitis B HBV virus.But still do not have relevant document record hydroxy benzoic acid and analog (except the salicylic acid) thereof so far, comprise 3,4, the 5-trihydroxybenzoic acid is used for preparation treatment skin mucosa medicine for treating viral infections.Though, experimental results show that gallic acid has inhibitory action to some virus, do not represent effectively all virus, just many antiviral drugs are the same as is known.Confirm that in research whether medicine effectively and before the pharmacological basis, can not predict its effect to certain type of virus.
Antimicrobial compositions has been described in the invention of Chinese patent CN1411339, U.S. Pat 6294186, and its benzoic acid analog that comprises safe and effective amount comprises those with following structure (II):
R wherein
1, R
2, R
4And R
5Be independently selected from H, OH, F, I, Br, Cl, SH, NH2, CN, alkyl, alkoxyl, NR
2, OR, NO
2, COR, CONR
2, CO
2R, SO
3R; Wherein R is independently selected from H, alkyl and alkoxyl.R
3Be independently selected from H, OH, F, I, Br, Cl, SH, CN, alkyl, alkoxyl, OR, NO
2, COR, CONR
2, CO
2R, SO
3R; Wherein R is independently selected from H, alkyl and alkoxyl.This patent also proposes most preferably to be selected from from salicylic acid (being 2 hydroxybenzoic acid), benzoic acid and their combination.
Though virus is minimum pathogenic microorganism, the propagation of virus is the widest, and nearly in the world 3/4 infectious disease is to be caused by virus at present, and more clinically disease is relevant with viral infection.
Condyloma acuminatum claims genital wart or genital wart again, is the skin mucosa benign neoplasm that is caused by human papillomavirus (HPV), for present modal one of disease that spreads through sex intercourse, with the substantial connection that has of phallic inflammation and cancer.At present, the medicine of treatment condyloma acuminatum has podophyllotoxin d, and advantage is a short treating period, but has zest, problem that toxic and side effects is big.Concrete manifestation is pain, edema, erosion etc.Recombinant human interferon-alpha-2 β the gel of medicine for external use treatment condyloma acuminatum is to generally acknowledge resultful medicine at present.
In recent years result of study shows (Chen Fuqiang etc., treatment and prevention of tumour magazine, 2001,8 (4) 342-344; Xu Chengkang, Zhongshan Medical Univ.'s journal, 1998,19 (3): 223-226), 29.3% patients of cervical ruin presents the HPV positive, and the normal cervix positive rate only is 11.1%.It is reported (Ahn ws et al, J CellBiochem Suppl, 1997; 28-29:133-139), high-risk HPV (human papillomavirus) 16,18 type expression rates are 69% in the chronic cervicitis, high-risk HPV 16,18 recall rates present with the increase of cervical erosion degree and increase progressively trend, and granular pattern or papillary erosion HPV16,18 recall rates and normal cervix comparing difference are remarkable.With PCR can record HPV16 in the cervical cancer, 18 positive rates reach 83.33%, high-risk HPV DNA is incorporated into host cell chromosome, can produce E6, E7 oncoprotein, they suppress antioncogene p53 and Rb respectively, make cell escape the control of p53 and Rb, cause cell cycle control not normal, make active, the tumor growth of the hyperplasia that remains static usually.If HPV16 continues to exist, just can make the cervical lesions progress.Cervical HPV infection and pudendum infect different, based on the HPV16/18 type, condyloma latum does not often take place change, but with the inapparent infection long-term existence, cause atypical hyperplasia earlier in the palace, when other factors participate in and cause canceration.
Herpes simplex virus (HSV) is a distrand DNA virus, its through the oral cavity, number of ways such as respiratory tract, reproductive tract mucosa and damaged skin invade body.The people infects very general, and infection rate reaches 80～90%, and common clinical manifestation is the herpes that mucosa or local skin gather, and also serious systemic disease can take place occasionally, involves internal organs.Studies show that HSV-1 and HSV-2 may be relevant with lip cancer, carcinoma vulvae and cervical cancer respectively, once be subjected to people and pay attention to (Sun He etc., Chinese practical gynecological and obstetrics' magazine, 2001,17 (7): 407-409).Medicine has iodouracil desoxyriboside, cytosine arabinoside, vidarabine, bromine ethylene uridnine and acycloguanosine etc. at present, but treatment time is longer, needs 5 to 7 days.
Summary of the invention
Main purpose of the present invention is to provide P-hydroxybenzoic acid and the application of analog in preparation prevention and treatment skin mucous membrane virus infection medicine thereof, wherein P-hydroxybenzoic acid and analog thereof are selected from one or more in the represented chemical compound of following general formula (I)
R wherein
1, R
2, R
3, R
4Be independently selected from OH or H, preferred P-hydroxybenzoic acid, 2,4-resorcylic acid, 3,4-resorcylic acid, 2,3,4-trihydroxybenzoic acid, 3,4,5-trihydroxybenzoic acid, 2,4,5-trihydroxybenzoic acid; More preferably P-hydroxybenzoic acid, 2,4-resorcylic acid, 3,4,5-trihydroxybenzoic acid; Most preferably 3,4, the 5-trihydroxybenzoic acid is a gallic acid.
Above-claimed cpd and/or contain the effective dose of the compositions of above-claimed cpd as active component, can be used on the purposes of preparation treatment humans and animals skin mucous membrane virus disease medicament, particularly treat the purposes of humans and animals skin mucosa HPV viral disease medicine, comprise condyloma acuminatum, vagina, cervicitis and cervical erosion and auxiliary treatment cervical cancer.
The present invention observes active component and product effect by the change of the amount of fluorescence quantitative PCR detection HPV virus, and this method is used (Cai Youling etc., Chinese std aids control, 2002,8:2,108 in the several pieces of documents of publishing; Wu Yuansheng, model are auspicious strong etc., and the practical combination of Chinese and Western medicine is clinical, and 2003,3:2,1).
The result shows, the tissue homogenate of condyloma acuminatum after adding gallic acid 24 hours, FQ-POVR can not detect virus again, add P-hydroxybenzoic acid, 2,3-resorcylic acid, 2, behind the 4-resorcylic acid, the HPV16/18 minimizing is made an appointment with half, 3, the 4-resorcylic acid slightly reduces, and blank pipe and control sample benzoic acid, salicylic acid, benzoic acid and salicylic acid composition pipe have the very HPV virus quantity of high concentration, illustrate that chemical compound of the present invention is in external ability with the condyloma acuminatum virus of fast and effeciently going out.And the preferred benzoic acid of invention, salicylic acid and the benzoic acid of Chinese patent CN1411339, U.S. Pat 6294186 and salicylic acid composition can not be killed HPV virus, after adding benzoic acid, salicylic acid and benzoic acid and salicylic acid composition, virus quantity and blank winding are near.
Above-claimed cpd and/or contain its compositions as the active component effective dose, preparing various preparations with the various supplementary product compatibilities of skin mucosa medication, can be pharmaceutically acceptable preparation of unguentum, gel, lotion, tablet, suppository, membrane, spray and other.
Above-claimed cpd and/or contain its compositions as the active component effective dose, as antimicrobial products, wherein said product is selected from the personal care product, and described personal care product is hand soaps, sanitary washing agent, bathing agent, shower glue, bath lotion, personal nursing wiping examination thing, facial tissue, intranasal spray and their combination.
Mostly compound activity composition of the present invention is known compound, and some have been used to prepare food additive, some are pharmaceutic adjuvants, and also having some is medicinal intermediate, can buy on the market, also can extract from natural plants.
When preparation the said goods, can use unification compound or its compositions.When being used to prepare pharmaceutical formulation, can with different medicine and pharmaceutically acceptable carrier combinations, be beneficial to the formation of preparation, these carriers can be:
Starch, dextrin, tween 80, carbomer, cellulose, sodium carboxymethyl cellulose, sodium alginate, glycerol, propylene glycol, Polyethylene Glycol, laurocapram, isopropyl alcohol, triethanolamine, sorbester p18, but be not limited thereto.
In addition, unification compound or its compositions as active component, can also add in disinfectant solution, hand soaps, sanitary washing agent, bathing agent, shower glue, bath lotion, personal nursing wiping examination thing, facial tissue, the intranasal spray, be used to kill the virus on skin mucosa surface.
The specific embodiment
Below in conjunction with embodiment, further specify the present invention, but the present invention is not limited to these embodiment, any on essence spirit of the present invention improvement or substitute, still belong to desired protection domain in claims of the present invention.
Main material of the present invention (content is all greater than 99%) and source thereof:
Material source
P-hydroxybenzoic acid Chemical Reagent Co., Ltd., Sinopharm Group
2, big chemical industry company limited in the city of 3-resorcylic acid Taizhou
2, big chemical industry company limited in the city of 4-resorcylic acid Taizhou
3, big chemical industry company limited in the city of 4-resorcylic acid Taizhou
3, the special Fine Chemical Co., Ltd of 5-resorcylic acid Haimen City bass
2,3,4-trihydroxybenzoic acid Nanjing Longyuan Natural Polyphenols Synthesis Factory
Gallic acid Zhejiang Province Ouhai chemical reagent factory
2,4,5-trihydroxybenzoic acid Nanjing Longyuan Natural Polyphenols Synthesis Factory
Salicylic acid Tianjin benchmark chemical reagent company limited
Fanyu, benzoic acid Guangzhou power is strengthened factory
Recombinant human interferon-alpha-2 β gel Zhaofeng Keda Pharmaceutics Co., Ltd., Hefei
Polyinosini Guangdong is opened and is changed pharmaceutical factory all one's life
The preparation of embodiment 1 anti-HPV virus microemulsion disinfectant solution
Get 1,2-propylene glycol 20ml, Tween 80 15ml, azone 5ml mix, and adding sterile purified water to cumulative volume is 100ml, gets external preparation solution.Get P-hydroxybenzoic acid, gallic acid, 2,4-resorcylic acid 10g adds external preparation solution 50ml respectively, regulate pH to 5.5, add external preparation solution then to 100ml, get 10% P-hydroxybenzoic acid, gallic acid, 2,4-resorcylic acid microemulsion.
The preparation of embodiment 2 compound recipe gallic acid effervescent tablets
Get gallic acid 0.25g, polyinosini 0.01g, tartaric acid 0.45g and cross 80 mesh sieves respectively, make soft material with 95% ethanol, the wet grain of the 12 mesh sieve systems of crossing, in 50 ℃ of dryings, standby.Other gets sodium bicarbonate 0.65g, dextrin 0.02g adds sterile distilled water system soft material, and the wet grain of the 12 mesh sieve systems of crossing in 50 ℃ of dryings, mixes with above-mentioned dry granular then, and granulate adds an amount of sterile purified water, and baking adds 0.01g PEG6000 for a moment.Mixing, tabletting, promptly.
The experiment of embodiment 3 fluorescence quantitative PCR detection HPV virus screening of medicaments
The drug sample preparation:
Respectively get 1,2-propylene glycol 20ml, Tween 80 15ml are solvent, respectively with benzoic acid, salicylic acid, P-hydroxybenzoic acid, 3,4-resorcylic acid, gallic acid, 2,3-resorcylic acid, 2, the 4-resorcylic acid is mixed with the solution of 0.01mol/L, regulates pH to 5.5.
The HPV viral source:
From the condyloma acuminatum specimen of multidigit patients clinical standard, after cutting,, under aseptic condition, specimen is shredded with normal saline flush away blood, add 3 times of volume normal saline mixings, grind to form homogenate placement-40C ° standby.
Test method:
Press grouping shown in the table 1, get condyloma acuminatum tissue homogenate 50 μ l for every group, add respectively for each 50 μ l of reagent product solution.37 ℃ of incubations 24 hours, then by reaching the HPV6 that peace gene diagnosis center provides, 11 and 16, the operating procedure that 18 type FQ-PCR diagnostic kits provide detects: adopt conventional alkaline lysis method of extracting DNA0.2ml to go in the thin-walled reaction tube, add certain density primer, F-PROBE, DNTP, archaeal dna polymerase and buffer etc. simultaneously, use ABI PRISM
TM7700 fluorescent quantitative PCR instrument, after 93 ℃ of 2min gave degeneration, by 93 ℃ of 45s, 55 ℃ of 120s carried out 40 circulations repeatedly, and quantitative result is calculated the quantitative result of initial copy number by the computer software automatic analyser.Data see Table 1.
The result shows: the tissue homogenate of condyloma acuminatum after adding gallic acid 24 hours, FQ-POVR can not detect virus again, add P-hydroxybenzoic acid, 2,3-resorcylic acid, 2, behind the 4-resorcylic acid, the HPV16/18 minimizing is made an appointment with half, 3, the 4-resorcylic acid slightly reduces, and and blank pipe and control sample benzoic acid, salicylic acid and benzoic acid and salicylic acid composition pipe have the very HPV virus quantity of high concentration, illustrate that chemical compound of the present invention is in external ability with the condyloma acuminatum virus of fast and effeciently going out.
The experiment of table 1 fluorescence quantitative PCR detection HPV virus screening of medicaments
Embodiment 4 clinical external curing condyloma acuminatum are observed
Diagnostic criteria:
Compile with reference to health and epidemic prevention department of Ministry of Health of the People's Republic of China that " related content in the prevention and treatment of venereal diseases handbook 1994 the 2nd edition: the soft proliferation of typical pudendum (or crissum) skin mucosa position nipple sample, cauliflower form or other shape, 5% acetic acid is tested the positive in vain.
Include in and exclusion standard:
Meet above-mentioned diagnostic criteria, single skin lesion diameter≤0.5cm, the patient that preceding 2 weeks of going to a doctor were not carried out relevant treatment includes clinical observation in.Pudendum genitals fungus, infusorian, bacterial infection or other complication person are arranged, age of sucking, anemia of pregnant woman or have the chronic wasting disease of whole body, serious hepatorenal disease person not to include observation in.When treating, the aeg avoids menstrual phase.
Experimental technique:
Outpatient service selects to meet condyloma acuminatum patient 40 examples of observation condition, and random packet is divided into P-hydroxybenzoic acid group, gallic acid group and recombinant human interferon-alpha-2 β gel matched group.
Each 10 gram of gallic acid and P-hydroxybenzoic acid, two groups add 1 respectively, 2-propylene glycol 20ml, Tween 80 15ml, azone 5ml, respectively adding sterile purified water to cumulative volume after the mixing is 100ml, gets 10% external preparation solution.
Patient smears the affected part with gallic acid or hydroxy benzoic acid solution or recombinant human interferon-alpha-2 β gel, divides early, middle and late local dispenser every day 3 times, is advisable can hide the wart body, and the medicine-feeding back exposes affected part and restraint 20min.
Curative effect determinate standard:
Observing time: 8 days, the person of not coming off continued usefulness, followed up a case by regular visits to for 12 weeks.
Observation index: position, form, size and the number of carefully checking and describe the wart body before the treatment.
Recovery from illness: all skin lesion all disappear; Produce effects: 70% above skin lesion disappears; Progressive: 30% above skin lesion disappears; Invalid: the skin lesion less than 30% that disappears, former skin lesion no change or increase.Observed result sees Table 2.
The result shows: the recombinant human interferon-alpha-2 β gel of medicine for external use treatment condyloma acuminatum is to generally acknowledge the medicine of effect at present, but also wants for 4 weeks the shortest course of treatment.Learn by statistics and handle, P-hydroxybenzoic acid and gallic acid effect are obviously good than reorganization human interferon-alpha-2 β gel, and there were significant differences.And The compounds of this invention does not have obvious irritation to skin mucosa, and side effect only has one or two people to feel burning sensation.
The clinical external curing condyloma acuminatum of table 2 observed result
Embodiment 5 clinical external curing herpes simplex virus (HSV) infect
Get embodiment 1 preparation gallic acid microemulsion disinfectant solution, choosing is divided into gallic acid microemulsion disinfectant solution group and acycloguanosine ointment group at random through clinical diagnosis herpes simplex virus (HSV) the infected 22 people, and 11 person-times every group, medication every day three times, the affected part is smeared in external.The result shows: the gallic acid disinfectant solution group natural law of on average fully recovering is 3 days, and the acycloguanosine ointment group natural law of on average fully recovering is 5.5 days, and there were significant differences for both.Gallic acid disinfectant solution group effect is better than acycloguanosine ointment group.
The preparation of embodiment 6 liquid hand soaps
According to listed each composition and usage ratio thereof in the table 4, add about 5% water and the material except that P-hydroxybenzoic acid, NaOH or HCl in the blending tank, be heated to 80 ℃ also stirring until dissolving.Cool to room temperature adds gallic acid, stirs until material dissolution.Adjust pH value to 5.0 with NaOH or HCl, the water that adds surplus is made product.
The preparation of table 3 liquid hand soaps
| Component (wt.%) | 6 | 7 | 8 | 9 | 10 |
| Myristyl sodium sulfate | -- | 5.00 | 5.00 | -- | 5.00 |
| 1, the 2-propylene glycol | 20.00 (V/V) | 20.00 (V/V) | 20.00 (V/V) | 20.00 (V/V) | 20.00 (V/V) |
| Gallic acid | 1.00 | 5.00 | 8.00 | 4.00 | -- |
| NaOH/HCl | To pH5.0 | To pH4.5 | To pH4.0 | To pH6.5 | To pH6.0 |
| Between right-chloro--xylenols | 1.50 | -- | -- | -- | -- |
| Triclosan | -- | 0.25 | 1.00 | -- | 1.00 |
| Spice | 1.0 | 1.0 | -- | 1.0 | 1.0 |
| Sterile purified water | To 100% | To 100% | To 100% | To 100% | To 100% |
Claims (4)
1, chemical compound 3,4, the application of 5-trihydroxybenzoic acid in preparation prevention and treatment skin mucous membrane virus infection medicine, and wherein said skin mucous membrane virus infection is meant humans and animals human papillomavirus's infection.
2, application as claimed in claim 1 is with 3,4, unguentum, gel, lotion, tablet, suppository, membrane or the spray that 5-trihydroxybenzoic acid and enepidermic various supplementary product compatibility are prepared into and other preparations of acceptable pharmaceutically.
3, application as claimed in claim 1 is with 3,4, and 5-trihydroxybenzoic acid and enepidermic various supplementary product compatibility are prepared into disinfectant solution, sanitary washing agent, bathing agent, personal nursing wiping examination thing, intranasal spray and their combination.
4, as the arbitrary described application of claim 1-3, wherein skin mucous membrane virus infection is meant vaginitis, cervicitis and the cervical erosion that human papilloma virus infection causes.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100122885A CN100428930C (en) | 2005-08-02 | 2005-08-02 | Application of p-hydroxybenzoic acid and its analogue in the preparing process of medicine for preventing and treating skin mucous membrane virus infection |
| PCT/CN2006/001791 WO2007014514A1 (en) | 2005-08-02 | 2006-07-21 | Use of p-hydroxybenzoic acid and analogues for the manufacture of a mendicament for the prevention and treatment of skin mucosa virus infection |
| US12/024,833 US8044098B2 (en) | 2005-08-02 | 2008-02-01 | Use of hydroxybenzoic acids and their esters and analogues for preventing or treating virus infection |
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|---|---|---|---|
| CNB2005100122885A CN100428930C (en) | 2005-08-02 | 2005-08-02 | Application of p-hydroxybenzoic acid and its analogue in the preparing process of medicine for preventing and treating skin mucous membrane virus infection |
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| CN100428930C true CN100428930C (en) | 2008-10-29 |
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| GB2450358A (en) * | 2007-06-20 | 2008-12-24 | Roy Arlington Jordan | Alkyl- and alkanolammonium hydroxybenzoate salts for the topical treatment of infection, inflammation and pain |
| CN106474142A (en) * | 2016-08-28 | 2017-03-08 | 贺秀平 | A kind of oral formulations treating leukoplakia of cervix complication prevention and preparation method thereof |
| CN107929384A (en) * | 2017-11-28 | 2018-04-20 | 辽宁大学 | Application of the black raspberry extract in treatment cervicitis, cervical erosion medicine is prepared |
| CN108498557A (en) * | 2018-07-05 | 2018-09-07 | 周长征 | The active component and preparation method of the anti-HSV-1 viruses of Ramulus euonymi |
| CN109620820B (en) * | 2019-01-30 | 2021-03-30 | 桂林医学院 | Application of p-hydroxybenzoic acid in preparing medicine for treating inflammatory bowel disease |
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| JPH09328404A (en) * | 1996-06-07 | 1997-12-22 | Iwao Hishida | Microbicidal, antimicrobial and inactivating agent |
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| CN1907275A (en) | 2007-02-07 |
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