CN111743864B - Sports trauma spray and preparation method thereof - Google Patents
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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
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
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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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- 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
- A61K47/06—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
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- 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
- A61K47/06—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
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- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
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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
- A61K9/10—Dispersions; Emulsions
- A61K9/12—Aerosols; Foams
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
Abstract
The invention discloses a sports trauma spray and a preparation method thereof. In particular, the physical trauma spray is a nanoemulsion spray made from N-tert-butyl-4- {3- [ (4-chlorophenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide, isopropyl myristate, ethyl oleate, span 80, propylene glycol, benzalkonium chloride and water. The sports trauma spray is suitable for nursing sports trauma, in particular hemorrhagic wounds such as abrasion or laceration.
Description
Technical Field
The invention belongs to the field of sports medicine, and particularly relates to a sports trauma spray and a preparation method thereof.
Background
Sports injuries generally refer to various injuries occurring during sports activities, mainly including bruises, contusions, sprains, lacerations, dislocations and fractures, among others. The injury site and severity of physical trauma are related to the sport and technical characteristics. For example, a track and field training athlete is likely to suffer from skin abrasion, muscle strain, joint ligament strain, muscle spasm, soreness, etc., the injured parts of a gymnastic athlete are mostly the wrist, shoulder, and waist, and tennis athletes and javelins are frequently suffering from tennis elbow, etc.
Sports trauma is one of the important reasons affecting the physical health of the sporter and hindering sports training. Because of the wide variety of sports, there is also a diversity of injuries from sports injuries. From the aspect of morbidity, although the types of trauma vary from one sport to another and from one body part to another, generally, small wounds (such as abrasions) are more and less severe. Some small wounds are not cared properly, and the wounds can be infected suppuratively, even serious complications such as systemic infection and the like which are life-threatening. Therefore, various traumas occurring during physical exercise must be treated in a timely manner.
At present, the wound treatment of sports trauma is carried out in a manner which is not limited to the use of various protective bands, support bands and the application of topical physiotherapy, such as massage, physiotherapy, topical application of Chinese medicines, topical closure (for example, the use of procaine, prednisolone, hydrocortisone acetate, hyaluronidase, chymotrypsin), and the like. These measures have the effect of preventing strain and re-injury, improving wound metabolism, eliminating edema, accelerating healing, eliminating paralysis and scar adhesion, etc. However, these conventional methods are cumbersome to apply and the rate of wound healing is relatively slow. Thus, there is a continuing unmet need in the art for new drugs to treat sports injuries.
Disclosure of Invention
One object of the present invention is to provide a sports trauma spray. The invention also aims to provide a preparation method of the sports trauma spray.
As a result of intensive studies, the present inventors have found that the compound N-tert-butyl-4- {3- [ (4-chlorophenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide, particularly N-tert-butyl-4- {3- [ (4-chlorophenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide in the form of a nanoemulsion spray prepared by the method of the present invention, has a superior therapeutic effect on a trauma model of guinea pigs, and thus have completed the present invention.
Accordingly, the invention provides a sports trauma spray. In particular, the physical trauma spray is a nanoemulsion spray made from N-tert-butyl-4- {3- [ (4-chlorophenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide, isopropyl myristate, ethyl oleate, span 80, propylene glycol, benzalkonium chloride and water. The sports trauma spray is suitable for nursing sports trauma, in particular hemorrhagic wounds such as abrasion or laceration.
Accordingly, the invention provides a sports trauma spray, which is characterized in that the sports trauma spray is a nano-emulsion spray prepared from N-tert-butyl-4- {3- [ (4-chlorphenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide, isopropyl myristate, ethyl oleate, span 80, propylene glycol, benzalkonium chloride and water, wherein the mass ratio of N-tert-butyl-4- {3- [ (4-chlorphenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide, isopropyl myristate, ethyl oleate, span 80, propylene glycol, benzalkonium chloride and water is 0.5-2:2.5-10:1.5-6:10-40:3.5-14:0.05-0.2: 40-160.
For example, in one embodiment, the mass ratio of N-tert-butyl-4- {3- [ (4-chlorophenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide, isopropyl myristate, ethyl oleate, span 80, propylene glycol, benzalkonium chloride, and water is 1:5:3:20:7:0.1: 80.
In addition, the invention also provides a preparation method of the sports trauma spray, which comprises the following steps:
(1) mixing isopropyl myristate, ethyl oleate, span 80 and propylene glycol thoroughly, then adding N-tert-butyl-4- {3- [ (4-chlorophenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide under stirring to form an oil phase;
(2) dissolving benzalkonium chloride in water to form a water phase;
(3) adding the oil phase prepared in the step (1) into the water phase prepared in the step (2) under stirring, and putting the mixture into an ultrasonic generator for shaking and mixing to obtain the sports trauma spray.
In one embodiment, the stirring in step (1) and/or (3) is performed by magnetic stirring under the condition of a thermostatic water bath. Preferably, the temperature of the water bath is 30-45 ℃, more preferably 37 ℃.
In another embodiment, the oscillatory mixing in step (3) is high frequency oscillatory mixing at 40-50Hz for 15-25 min. Preferably, the oscillatory mixing in step (3) is oscillatory mixing at a high frequency of 45Hz for 20 min.
The structural formula of the compound N-tertiary butyl-4- {3- [ (4-chlorphenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide in the sports trauma spray of the invention is as follows:
this compound is disclosed in international patent publication No. WO2011/140164a1 (see page 46). This patent document relates generally to compounds that inhibit Fatty Acid Amide Hydrolase (FAAH) activity, compositions comprising the compounds, and methods of using the same. The compounds are believed to be useful in the treatment of diseases, conditions or disorders that would benefit from inhibition of fatty acid amide hydrolase and increased endogenous fatty acid amide levels. However, the patent document does not mention the use of said compounds for the treatment of sports injuries.
The sports trauma spray of the invention may be administered by filling into a suitable spray. The nebulizer is a device for converting a liquid medicine or other liquid into a mist by suction and uniformly spraying the mist onto an affected part or other objects, and generally comprises a container, a compressed air device, a thin tube, a nozzle, and the like. The size of a nebulizer suitable for the sports trauma spray of the invention is suitably 10mL, 25mL, etc., all as known in the art.
The invention has the following beneficial effects:
1. the new pharmaceutical application of the compound N-tert-butyl-4- {3- [ (4-chlorphenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide is found, and the clinical drug selection is enriched.
2. Compared with the traditional penetration mode, the nano-emulsion spray has improved biocompatibility, so that the active ingredients can accelerate the healing of wounds.
To further illustrate the concepts and advantages of the present invention, the following description of the preferred embodiments of the invention and their effects are presented in conjunction with specific examples. It should be understood, however, that the description of these preferred embodiments is in no way intended to limit the invention as claimed.
Detailed Description
Example 1
The physical trauma spray of this example was prepared by weighing 0.5g of N-tert-butyl-4- {3- [ (4-chlorophenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide, 5g of isopropyl myristate, 3g of ethyl oleate, 8020g of span, 7g of propylene glycol, 0.1g of benzalkonium chloride and 80g of water as follows:
(1) fully mixing isopropyl myristate, ethyl oleate, span 80 and propylene glycol, and then adding N-tert-butyl-4- {3- [ (4-chlorphenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide under magnetic stirring in a constant-temperature water bath at 37 ℃ to form an oil phase;
(2) dissolving benzalkonium chloride in water to form a water phase;
(3) adding the oil phase prepared in the step (1) into the water phase prepared in the step (2) under the magnetic stirring of a thermostatic water bath at 37 ℃, and placing the mixture in an ultrasonic generator to mix for 20min under high-frequency oscillation at 45Hz, thereby obtaining the sports trauma spray.
Example 2
The physical trauma spray of the embodiment is prepared by weighing 1g of N-tert-butyl-4- {3- [ (4-chlorophenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide, 5g of isopropyl myristate, 3g of ethyl oleate, 8020g of span, 7g of propylene glycol, 0.1g of benzalkonium chloride and 80g of water according to the following method:
(1) fully mixing isopropyl myristate, ethyl oleate, span 80 and propylene glycol, and then adding N-tert-butyl-4- {3- [ (4-chlorphenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide under magnetic stirring in a constant-temperature water bath at 37 ℃ to form an oil phase;
(2) dissolving benzalkonium chloride in water to form a water phase;
(3) adding the oil phase prepared in the step (1) into the water phase prepared in the step (2) under the magnetic stirring of a thermostatic water bath at 37 ℃, and placing the mixture in an ultrasonic generator to mix for 20min under high-frequency oscillation at 45Hz, thereby obtaining the sports trauma spray.
Example 3
Weighing 2g of N-tert-butyl-4- {3- [ (4-chlorophenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide, 5g of isopropyl myristate, 3g of ethyl oleate, 8020g of span, 7g of propylene glycol, 0.1g of benzalkonium chloride and 80g of water, preparing the physical trauma spray according to the following method:
(1) fully mixing isopropyl myristate, ethyl oleate, span 80 and propylene glycol, and then adding N-tert-butyl-4- {3- [ (4-chlorphenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide under magnetic stirring in a constant-temperature water bath at 37 ℃ to form an oil phase;
(2) dissolving benzalkonium chloride in water to form a water phase;
(3) adding the oil phase prepared in the step (1) into the water phase prepared in the step (2) under the magnetic stirring of a thermostatic water bath at 37 ℃, and placing the mixture in an ultrasonic generator to mix for 20min under high-frequency oscillation at 45Hz, thereby obtaining the sports trauma spray.
Experimental example 1
Particle size investigation of sports trauma spray
The particle size of the spray of example 2 was measured using a laser particle size analyzer. 5mL of the spray of example 2 was measured using polystyrene spherical beads as external standards at a 90 ℃ light scattering measurement angle. The results showed that the spray of example 2 had an average particle size of (86.87. + -. 4.23) nm and a polydispersity of 0.108.
Experimental example 2
Effect test
1. Test object
The experimental animals used in this experiment were English guinea pigs (Guineapig, purchased from Tokyo Weitongli Hua laboratory animal technology Co., Ltd.) weighing 300. + -.20 g. Guinea pigs were acclimated in a clean animal house with room temperature of 22-23 deg.C, air humidity of 45% -55%, light/dark switching every 12 hours for 2 days. Animals can eat and drink water freely.
2. Experimental methods
Before the start of the experiment, guinea pig skin was exposed by depilating the back with a shaver, followed by depilatory with a commercially available depilatory cream and rinsing with tap water. After 24 hours, a skin incision of 1cm in length and 0.5cm in depth was made in the skin with a scalpel. Then, the guinea pigs were randomly divided into 4 groups, i.e., a blank control group, a positive control group, a compound group, and example groups, 10 animals per group, and hermaphrodites were administered to the animals of each group according to the following dosing schedule:
blank control group: only applying proper medical sterilized alcohol to the wound, and applying the medical sterilized alcohol to the wound for 1 time every 12 hours;
positive control group: the commercially available ointment of mupirocin, bazedoary, was applied to the wound at a dose of 0.1 g/tube 1 time per 12 hours;
group of compounds: applying to the wound N-tert-butyl-4- {3- [ (4-chlorophenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide dissolved in ethanol at a dose of 2mg N-tert-butyl-4- {3- [ (4-chlorophenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide per one, 1 administration per 12 hours;
example set: the spray prepared according to example 2 was applied to the wound at a dose corresponding to 2mg of N-tert-butyl-4- {3- [ (4-chlorophenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide per mouse, 1 application per 12 hours.
The time range of wound healing (lower limit of the range is the time at which the group of guinea pigs are the earliest to develop healing and upper limit of the range is the time at which the group of guinea pigs are the latest to develop healing) and the scar thickness after healing were recorded for each group of guinea pigs and observed for bacterial infection.
3. Results of the experiment
See table 1 below.
TABLE 1 Guinea pig trauma treatment protocol
Values are mean ± standard deviation of results for each experimental group.
The experimental results in table 1 show that the wound healing speed of the guinea pigs of the positive control group, the compound group, and the example group was significantly accelerated, and at the same time, the scar formation and the bacterial proliferation were inhibited, compared to the blank control group. These results suggest that N-tert-butyl-4- {3- [ (4-chlorophenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide accelerates wound healing and, at the same time, inhibits scarring and bacterial infection, and is therefore suitable for the care of bleeding wounds, particularly abrasions or lacerations, in sports injuries. In addition, these results also suggest that the use of N-tert-butyl-4- {3- [ (4-chlorophenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide as a nanoemulsion spray according to the method of the present invention can improve the corresponding therapeutic efficacy of the compound. This is probably due to the solubilizing ability of the nanoemulsion, which can affect the structure of the skin and thus increase the penetration of the drug into the skin.
Claims (2)
1. Use of a nanoemulsion spray made from N-tert-butyl-4- {3- [ (4-chlorophenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide, isopropyl myristate, ethyl oleate, span 80, propylene glycol, benzalkonium chloride and water in the manufacture of a medicament for a sports trauma spray for the care of bleeding wounds, wherein the mass ratio of N-tert-butyl-4- {3- [ (4-chlorophenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide, isopropyl myristate, ethyl oleate, span 80, propylene glycol, benzalkonium chloride and water is 0.5-2:2.5-10:1.5-6:10-40:3.5-14:0.05-0.2:40-160, the preparation method of the sports trauma spray comprises the following steps:
(1) mixing isopropyl myristate, ethyl oleate, span 80 and propylene glycol thoroughly, then adding N-tert-butyl-4- {3- [ (4-chlorophenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide under stirring to form an oil phase;
(2) dissolving benzalkonium chloride in water to form a water phase;
(3) adding the oil phase prepared in the step (1) into the water phase prepared in the step (2) under stirring, putting the mixture into an ultrasonic generator, and mixing the mixture in a shaking way to obtain the sports trauma spray,
wherein the stirring in the step (1) and/or (3) is performed by magnetic force under the condition of thermostatic water bath at 37 ℃, and the oscillatory mixing in the step (3) is performed by high-frequency oscillatory mixing at 45Hz for 20 min.
2. Use according to claim 1, characterized in that the mass ratio of N-tert-butyl-4- {3- [ (4-chlorophenyl) sulfanyl ] -1H-pyrrolo [2,3-b ] pyridin-2-yl } benzenesulfonamide, isopropyl myristate, ethyl oleate, span 80, propylene glycol, benzalkonium chloride and water is 1:5:3:20:7:0.1: 80.
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| UA108233C2 (en) * | 2010-05-03 | 2015-04-10 | Fatty acid amide hydrolysis activity modulators | |
| US20130059850A1 (en) * | 2010-05-06 | 2013-03-07 | Merck Sharp & Dohme Corp. | Aza-indole derivatives useful as modulators of faah |
| AR084433A1 (en) * | 2010-12-22 | 2013-05-15 | Ironwood Pharmaceuticals Inc | FAAH INHIBITORS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
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| CN110664756B (en) * | 2019-10-09 | 2020-11-17 | 吉林大学 | Trauma spray for children and preparation method thereof |
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