CN114831969A - Piroxicam-containing gel emplastrum for local skin and preparation method thereof - Google Patents

Piroxicam-containing gel emplastrum for local skin and preparation method thereof Download PDF

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CN114831969A
CN114831969A CN202210556468.3A CN202210556468A CN114831969A CN 114831969 A CN114831969 A CN 114831969A CN 202210556468 A CN202210556468 A CN 202210556468A CN 114831969 A CN114831969 A CN 114831969A
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piroxicam
skin
gel
plaster
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吴玫颖
刘晨红
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Sun Yat Sen University
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/5415—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/02—Inorganic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
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    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/38—Cellulose; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/42—Proteins; Polypeptides; Degradation products thereof; Derivatives thereof, e.g. albumin, gelatin or zein
    • 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
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

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  • Medicinal Preparation (AREA)

Abstract

The application discloses a piroxicam-containing gel emplastrum for local skin and a preparation method thereof, relating to the field of pharmaceutical preparations; the piroxicam-containing gel emplastrum for the skin local application is prepared from the following components in parts by weight: 0.1-5 wt% of piroxicam, 1-20 wt% of solvent, 1-20 wt% of penetration enhancer, 10-90 wt% of gel plaster matrix and the balance of water. In order to prevent the adverse reaction of the medicaments and improve the compliance of patients, the development direction of the application mainly changes the existing administration form of the piroxicam, namely the development of gel emplastrum for local application to skin. Based on the advantages of the gel plaster in local application, the piroxicam is taken as a model medicament, and aims to prolong the local action time of the model medicament, improve the skin permeability and stably exert the curative effect.

Description

Piroxicam-containing gel emplastrum for local skin and preparation method thereof
Technical Field
The application relates to the field of medicinal preparations, in particular to a piroxicam-containing gel emplastrum for local skin and a preparation method thereof.
Background
Musculoskeletal diseases occur in 20% to 33% of the world's population. A recent report in the united states indicates that one out of every two adults has musculoskeletal disease with an incidence rate equivalent to the sum of patients with cardiovascular disease and chronic respiratory disease. At present, no method for quick radical treatment exists, and the aim of drug treatment is to achieve a reasonable level which can be tolerated by patients by controlling pain and inflammation and improve the quality of life. Compared with an oral administration way, the local external preparation is directly applied to the skin of a lesion part, reaches a pain tissue through skin penetration to play an analgesic role, has the advantages of quick response, high local concentration, less systemic exposure, less systemic adverse reaction and the like, and is more suitable for treating acute and chronic inflammatory pain of a musculoskeletal system. Wherein, the non-steroidal anti-inflammatory drugs (NSAIDs) are first-line drugs for treating rheumatoid arthritis, osteoarthritis, neck, shoulder, waist and leg pain, gout and various mild and moderate pains, especially acute and chronic inflammatory pains and the like. Topical NSAIDs provide analgesic effects comparable to oral NSAIDs; of all external analgesics, external NSAIDs have the most significant therapeutic effect. Topical NSAIDs may be preferred if there is only localized mild to moderate pain (acute pain or acute episodes of chronic pain). Currently marketed external NSAIDs include piroxicam, indomethacin, loxoprofen sodium, flurbiprofen, diclofenac, ketoprofen, and the like.
Disclosure of Invention
In view of the above disadvantages, the present application provides a piroxicam-containing gel patch for topical application to the skin and a preparation method thereof.
In order to solve the technical problem, the technical scheme provided by the application is as follows: a piroxicam-containing gel emplastrum for topical skin is prepared from the following components in parts by weight:
0.1-5 wt% of piroxicam, 1-20 wt% of solvent, 1-20 wt% of penetration enhancer, 10-90 wt% of gel plaster matrix and the balance of water.
As some alternative embodiments herein, the solvent is N-methylpyrrolidone and the penetration enhancer is at least one of laurocapram and isopropyl myristate.
As some alternative embodiments of the present application, the gel plaster base comprises: at least one of a humectant, a tackifier, a filler, a matrix material and a crosslinking modifier.
As some alternative embodiments herein, the humectants are glycerin and propylene glycol;
the tackifier is at least one of polyvinyl alcohol, gelatin and sodium carboxymethylcellulose;
the filler is at least one of talcum powder, kaolin and titanium dioxide;
the crosslinking regulator is at least one of aluminum dihydroxyl glycolate, edetate disodium and L-tartaric acid.
As some optional embodiments of the present application, the scaffolding matrix material is sodium polyacrylate NP-700.
In order to solve the technical problem, the present application further provides: a process for the preparation of the piroxicam-containing gel patch for topical application to the skin as described above, comprising the steps of:
mixing piroxicam, penetration enhancer and solvent in proportion to obtain piroxicam solution;
and mixing the piroxicam solution and the gel plaster substrate, and uniformly stirring to obtain the piroxicam-containing gel plaster for the topical skin.
As some alternative embodiments of the present application, the gel plaster base comprises a gel plaster first base and a gel plaster second base;
wherein the first matrix of the gel plaster is obtained by mixing the crosslinking regulator, the tackifier and water;
the second matrix of the gel plaster is obtained by mixing the skeleton matrix material, the filler, the tackifier, the crosslinking regulator and the humectant.
As some optional embodiments of the present application, the method comprises the following steps:
mixing piroxicam, penetration enhancer and solvent in proportion to obtain piroxicam solution;
mixing the piroxicam solution with the second matrix of the gel plaster, and then mixing with the first matrix of the gel plaster to obtain the piroxicam-containing gel plaster for the topical skin.
As some optional embodiments herein, the gel plaster first base is obtained by mixing the crosslinking modifier, the tackifier and water, and comprises:
the mixing temperature of the crosslinking regulator, the tackifier and water is 45 +/-5 ℃.
As some optional embodiments of the present application, after the step of mixing the piroxicam solution and the gel patch base and uniformly stirring to obtain the piroxicam-containing gel patch for topical application to skin, the method further comprises:
and (3) placing the piroxicam-containing gel plaster for local skin into a coating machine for coating, wherein the weight of each plaster is 10g, the cutting size is 14cm x 10cm, and the plaster is packaged by a paper-aluminum-plastic composite tape and then placed at 20-25 ℃ for crosslinking for 1 week to obtain a finished product.
Piroxicam is a long-acting non-steroidal anti-inflammatory and anti-rheumatic drug, has high bioavailability and long plasma half-life, and has the action mechanism that the synthesis and accumulation of Prostaglandins (PGs) are reduced by inhibiting the bioactivity of Cyclooxygenase (COX) in the metabolism process of arachidonic acid in cell membranes, so as to play roles of antipyresis, analgesia, anti-inflammation and anti-rheumatism. The long-term oral administration of the medicine can effectively control pain and simultaneously cause adverse reactions such as gastrointestinal tract and the like. At present, the main preparation forms comprise patches, gels, ointments, capsules, tablets and injections, and no piroxicam gel plaster is sold on the market temporarily. In order to prevent the adverse reaction of the medicaments and improve the compliance of patients, the development direction of the application mainly changes the existing administration form of the piroxicam, namely the development of gel emplastrum for local application to skin. Based on the advantages of the gel plaster in local application, the piroxicam is taken as a model medicament, and aims to prolong the local action time of the model medicament, improve the skin permeability and stably exert the curative effect.
Drawings
FIG. 1 is a graph of the cumulative transdermal (rat skin) penetration in vitro of piroxicam-containing gel patches for topical application to the skin at different drug loading rates according to the examples of the present application;
fig. 2 is a graph of the cumulative transdermal (pigskin) penetration in vitro of piroxicam-containing gel patches for topical application to skin at different drug loading rates according to the examples of the present application.
The implementation, functional features and advantages of the objectives of the present application will be further explained with reference to the accompanying drawings.
Detailed Description
It should be understood that the specific embodiments described herein are merely illustrative of the present application and are not intended to limit the present application.
Examples 1 to 5
The formulations of examples 1-5 are shown in Table 1:
table 1:
Figure BDA0003655119790000041
the preparation methods of examples 1 to 5 are as follows:
piroxicam solution: uniformly mixing laurocapram, isopropyl myristate and N-methylpyrrolidone, adding piroxicam, and stirring at room temperature until complete dissolution;
gel patch first matrix: adding disodium edetate into appropriate amount of water at room temperature, heating to 45 + -5 deg.C when disodium edetate is completely dissolved, adding L-tartaric acid and gelatin while stirring, cooling to 35 + -5 deg.C when disodium edetate is completely dissolved, and stirring at constant temperature;
gel patch secondary matrix: sequentially adding propylene glycol, partially neutralized sodium polyacrylate NP-700, titanium dioxide, talcum powder, sodium carboxymethylcellulose and dihydroxyaluminum glycinate into a proper amount of glycerol, mixing, uniformly stirring, stirring at a constant speed at normal temperature for later use, and adjusting the rotating speed to be 500rpm +/-50 rpm;
mixing the piroxicam solution with the second matrix of the gel plaster, stirring at high speed, adding the first matrix of the gel plaster, stirring at low speed to obtain the target plaster, coating the plaster in a coating machine, cutting into pieces of 14cm by 10cm, packaging with paper-aluminum-plastic composite tape, and crosslinking at 25 deg.C for 1 week.
Comparative examples 1 to 5
The formulations of comparative examples 1-5 are shown in Table 2:
table 2:
Figure BDA0003655119790000051
Figure BDA0003655119790000061
the preparation methods of comparative examples 1 to 5 are as follows:
piroxicam solution: uniformly mixing span 83, polysorbate 80, dementholized peppermint oil, menthol and isopropyl myristate with N-methylpyrrolidone, then adding piroxicam, and stirring at room temperature for later use after complete dissolution;
gel patch first matrix: adding disodium edetate into appropriate amount of water at room temperature, heating to 45 + -5 deg.C when disodium edetate is completely dissolved, adding L-tartaric acid and gelatin while stirring, cooling to 35 + -5 deg.C when disodium edetate is completely dissolved, and stirring at constant temperature;
gel patch secondary matrix: sequentially adding propylene glycol, partially neutralized sodium polyacrylate NP-700, titanium dioxide, talcum powder, sodium carboxymethylcellulose and dihydroxyaluminum glycinate into a proper amount of glycerol, mixing, uniformly stirring, stirring at a constant speed at normal temperature for later use, and adjusting the rotating speed to be 500rpm +/-50 rpm;
mixing the piroxicam solution with the second matrix of the gel plaster, stirring at high speed, adding the first matrix of the gel plaster, stirring at low speed to obtain the target plaster, coating the plaster in a coating machine, cutting into pieces of 14cm by 10cm, packaging with paper-aluminum-plastic composite tape, and crosslinking at 25 deg.C for 1 week.
The products obtained in examples 1 to 5 and comparative examples 1 to 5 were subjected to quality evaluation, and the evaluation results are shown in table 3:
table 3:
Figure BDA0003655119790000062
Figure BDA0003655119790000071
as can be seen from the above table, example 3, comparative example 1 and comparative example 3 have devitrification, i.e., unacceptable properties, and thus the in vitro transdermal and in vitro release was not subsequently examined for example 3, comparative example 1 and comparative example 3. In vitro release assay:
an improved Franz diffusion cell method is adopted, a cellulose acetate membrane is taken as a barrier, the piroxicam gel emplastrum with qualified properties is subjected to in vitro transdermal test determination, and 3 groups of parallel tests are respectively set.
Solution preparation:
pbsph7.4 medium: 3.628g disodium hydrogen phosphate, 0.24g potassium dihydrogen phosphate, 8.0g sodium chloride and 0.2g potassium sodium chloride, adding water to 1000ml, stirring thoroughly to dissolve, then adding concentrated hydrochloric acid to adjust pH to 7.4.
Physiological saline: 9g of sodium chloride is dissolved by adding 1000ml of water and evenly mixed to obtain the sodium chloride.
The determination method comprises the following steps:
cutting the Jinlong cellulose acetate film into a circular sheet with the diameter of 1.4cm, immediately soaking the circular sheet in physiological saline for 30min, wiping water by absorbent paper, fixing the cut Jinlong cellulose acetate film on a release port of a Franz diffusion cell, adding PBSpH7.4 serving as a release medium into a receiving chamber, keeping the water bath temperature constant at (32 +/-0.5) DEG C, stirring at 500rpm, sucking the release medium for 4m1 in 0h, 0.5h, 1h, 2h, 4h, 6h, 8h, 10h, 12h, 16h, 20h and 24h respectively, and simultaneously adding the same amount of PBSpH7.4. The results of calculating the cumulative percent absorption (i.e. the cumulative percentage of piroxicam that permeated over the total amount of piroxicam in the drug) are shown in table 4:
table 4:
Figure BDA0003655119790000081
as can be seen from the above table, the in vitro cumulative release rates of comparative example 2, comparative example 4 and comparative example 5 are lower than those of the examples, and the in vitro cumulative release rates of example 4 and example 5 are higher. Example 4 and example 5 were therefore examined subsequently for in vitro transdermal penetration.
In vitro transdermal test:
an in vitro transdermal test assay was performed using the piroxicam gel patch prepared in examples 4 and 5 using the modified Franz diffusion cell method with the ex vivo pigskin/rat skin as a barrier, wherein 3 sets of parallel tests were set for each of examples 4 and 5.
Solution preparation:
pbsph7.4 medium: 3.628g disodium hydrogen phosphate, 0.24g potassium dihydrogen phosphate, 8.0g sodium chloride and 0.2g potassium sodium chloride, adding water to 1000ml, stirring thoroughly to dissolve, then adding concentrated hydrochloric acid to adjust pH to 7.4.
Physiological saline: 9g of sodium chloride is dissolved by adding 1000ml of water and evenly mixed to obtain the sodium chloride.
The determination method comprises the following steps:
taking out the cut small fragrant pigskin from a refrigerator, naturally thawing, measuring the moisture by using a skin moisture loss instrument and measuring the thickness of the pigskin by using a vernier caliper, wherein the moisture and the thickness are within a certain range (the moisture is less than 10 percent, and the weight RSD (relative standard deviation) < 5 percent), and the skin quality consistency is ensured by controlling the surface moisture and the thickness. Then, the skin was soaked in physiological saline for 30min, the absorbent paper was wiped to dry, the treated skin was fixed to the release port of a Franz diffusion cell, pbsph7.4 was added to the receiving chamber as a release medium, the stratum corneum faced the supply cell, and the dermis faced the receiving cell. The temperature of the water bath is constant at (32 +/-0.5) DEG C, the stirring speed is 600rpm, the release medium is sucked for 4m1 within 0h, 1h, 4h, 8h, 12h, 18h and 24h respectively, and meanwhile, the PBSpH7.4 with the same amount is supplemented. The results of calculating the cumulative percent absorption (i.e., the percentage fraction of cumulative total piroxicam permeated to the total amount of piroxicam in the drug) are shown in tables 4-5 and fig. 1-2:
table 4:
Figure BDA0003655119790000091
table 5:
Figure BDA0003655119790000092
Figure BDA0003655119790000101
it can be seen that the development of the present application has been directed mainly to the change of the existing piroxicam administration form, i.e. the development of gel patch for topical application to the skin. Based on the advantages of the gel plaster in local application, the piroxicam is taken as a model medicament, and aims to prolong the local action time of the model medicament, improve the skin permeability and stably exert the curative effect.
The above description is only a preferred embodiment of the present application, and not intended to limit the scope of the present application, and all modifications of equivalent structures and equivalent processes, which are made by the contents of the specification and the drawings of the present application, or which are directly or indirectly applied to other related technical fields, are included in the scope of the present application.

Claims (10)

1. A piroxicam-containing gel emplastrum for topical skin is characterized by being prepared from the following components in parts by weight:
0.1-5 wt% of piroxicam, 1-20 wt% of solvent, 1-20 wt% of penetration enhancer, 10-90 wt% of gel plaster matrix and the balance of water.
2. The piroxicam-containing gel patch for topical application to the skin according to claim 1, wherein the solvent is N-methylpyrrolidone and the penetration enhancer is at least one of laurocapram and isopropyl myristate.
3. The piroxicam-containing gel patch for topical application to the skin according to claim 1, wherein said gel patch base comprises: at least one of a humectant, a tackifier, a filler, a matrix material and a crosslinking modifier.
4. The piroxicam-containing topical gel patch of claim 3, wherein the humectants are glycerin and propylene glycol;
the tackifier is at least one of polyvinyl alcohol, gelatin and sodium carboxymethylcellulose;
the filler is at least one of talcum powder, kaolin and titanium dioxide;
the crosslinking regulator is at least one of aluminum dihydroxyl glycolate, edetate disodium and L-tartaric acid.
5. The piroxicam-containing gel patch for topical application to the skin of claim 3, wherein the matrix material is sodium polyacrylate NP-700.
6. A process for the preparation of piroxicam-containing gel patches for topical application to the skin as claimed in any of claims 1 to 5, comprising the following steps:
mixing piroxicam, penetration enhancer and solvent in proportion to obtain piroxicam solution;
and mixing the piroxicam solution and the gel plaster substrate, and uniformly stirring to obtain the piroxicam-containing gel plaster for the topical skin.
7. The process for preparing a piroxicam-containing gel patch for topical application to the skin according to claim 6, wherein the gel patch base comprises a first gel patch base and a second gel patch base;
wherein the first matrix of the gel plaster is obtained by mixing the crosslinking regulator, the tackifier and water;
the second matrix of the gel plaster is obtained by mixing the skeleton matrix material, the filler, the tackifier, the crosslinking regulator and the humectant.
8. The process for preparing a piroxicam-containing gel patch for topical application to the skin according to claim 7, characterized in that it comprises the following steps:
mixing piroxicam, penetration enhancer and solvent in proportion to obtain piroxicam solution;
mixing the piroxicam solution with the second matrix of the gel plaster, and then mixing with the first matrix of the gel plaster to obtain the piroxicam-containing gel plaster for the topical skin.
9. The method for preparing piroxicam-containing gel patch for topical application to the skin according to claim 7, wherein the first matrix of gel patch is obtained by mixing the cross-linking modifier, the tackifier and water, and comprises the steps of:
the mixing temperature of the crosslinking regulator, the tackifier and water is 45 +/-5 ℃.
10. The method for preparing piroxicam-containing gel patch for topical skin application according to claim 6, wherein after the steps of mixing said piroxicam solution with the gel patch base and stirring to obtain piroxicam-containing gel patch for topical skin application, further comprising:
and (3) placing the piroxicam-containing gel plaster for local skin into a coating machine for coating, wherein the weight of each plaster is 10g, the cutting size is 14cm x 10cm, and the plaster is packaged by a paper-aluminum-plastic composite tape and then placed at 20-25 ℃ for crosslinking for 1 week to obtain a finished product.
CN202210556468.3A 2022-05-20 2022-05-20 Piroxicam-containing gel emplastrum for local skin and preparation method thereof Pending CN114831969A (en)

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Publication number Priority date Publication date Assignee Title
JPH09176015A (en) * 1995-12-28 1997-07-08 Showa Denko Kk Analgesic and anti-inflammatory cataplasm for external use
AU2001259348A1 (en) * 2000-09-15 2002-06-13 Elk Premium Building Products, Inc. Asphalt coated structural article
JP2014028767A (en) * 2012-07-31 2014-02-13 Lion Corp Patch

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Publication number Priority date Publication date Assignee Title
US6500560B1 (en) * 1999-11-30 2002-12-31 Elk Corporation Of Dallas Asphalt coated structural article

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09176015A (en) * 1995-12-28 1997-07-08 Showa Denko Kk Analgesic and anti-inflammatory cataplasm for external use
AU2001259348A1 (en) * 2000-09-15 2002-06-13 Elk Premium Building Products, Inc. Asphalt coated structural article
JP2014028767A (en) * 2012-07-31 2014-02-13 Lion Corp Patch

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Title
孟鸽飞等: "中药凝胶贴膏基质处方的研究进展" *

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Application publication date: 20220802