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WO2021111339A1 - (s)-3-[1-méthylpyrrolidin-2-yl]pyridine, ses analogues, ses précurseurs ou ses dérivés, destinés à être utilisés en tant que produit pharmaceutique sous forme de médicament topique semi-solide, visqueux et homogène, et médicament topique - Google Patents

(s)-3-[1-méthylpyrrolidin-2-yl]pyridine, ses analogues, ses précurseurs ou ses dérivés, destinés à être utilisés en tant que produit pharmaceutique sous forme de médicament topique semi-solide, visqueux et homogène, et médicament topique Download PDF

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Publication number
WO2021111339A1
WO2021111339A1 PCT/IB2020/061400 IB2020061400W WO2021111339A1 WO 2021111339 A1 WO2021111339 A1 WO 2021111339A1 IB 2020061400 W IB2020061400 W IB 2020061400W WO 2021111339 A1 WO2021111339 A1 WO 2021111339A1
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WO
WIPO (PCT)
Prior art keywords
methylpyrrolidin
pyridine
precursors
derivatives
analogues
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Ceased
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PCT/IB2020/061400
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English (en)
Inventor
Arturo Solis Herrera
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Priority to EP20820563.3A priority Critical patent/EP4069191A1/fr
Publication of WO2021111339A1 publication Critical patent/WO2021111339A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole

Definitions

  • the present invention relates to a (S)-3-[1-Methylpyrrolidin-2-yl]pyridine, analogues thereof, precursors thereof, or its derivatives - containing pharmaceutical in form of a homogeneous, viscous, semi-solid topical medication.
  • the invention relates to a topical medication.
  • (S)-3-[1- Methylpyrrolidin-2-yl]pyridine is accumulated in the leaves of these plants while its biosynthesis is taken place in the particular roots.
  • (S)-3-[1-Methylpyrrolidin-2- yl]pyridine constitutes approximately 0,6 to 0,3% of the dry weight of for example the tobacco plant and is present in the range of 2 to 7 pg/KG of various edible plants.
  • (S)-3-[1-Methylpyrrolidin-2-yl]pyridine is a stimulant drug acting as an agonist to most nicotinic acetylcholine receptors (nAChR). In lesser doses of approximately 1 mg the substance adds on as a stimulant in mammals, while high amounts of approximately 50 to 100 mg can start being harmful.
  • nAChR nicotinic acetylcholine receptors
  • (S)-3-[1-Methylpyrrolidin-2-yl]pyridine is hygroscopic, oily, colorless or pale yellow liquid, which is miscible with water and in its base form comprises a pyridine odor.
  • (S)-3-[1- Methylpyrrolidin-2-yl]pyridine comprises a molecular weight of approximately 172 g/mol, is readily soluble in alcohol, ether or light petroleum.
  • (S)-3-[1-Methylpyrrolidin-2- yl]pyridine forms salts with acids that are solid and water soluble. The substance is further absorbed from the intact skin and by the mucosa.
  • (S)-3-[1-Methylpyrrolidin-2- yl]pyridine undergoes extensive first pass metabolism when administered to the skin. Furthermore, (S)-3-[1-Methylpyrrolidin-2-yl]pyridine easily penetrates the skin, particularly the mucosa. The substance is able of being quickly distributed throughout the bloodstream and is even able to cross the blood-brain-barrier. The half-life of (S)-3-[1-Methylpyrrolidin-2- yl]pyridine in the body is approximately two hours.
  • (S)-3-[1-Methylpyrrolidin-2-yl]pyridine mentioned within the scope of the invention is always understood as (S)-3-[1-Methylpyrrolidin-2-yl]pyridine itself, analogues thereof, precursors thereof, its derivatives or nicotine which mimic the effect of (S)-3-[1-Methylpyrrolidin-2- yl]pyridine, either alone or in combination with other active substances can be used.
  • the special benefit of this invention is that a certain dosage of (S)-3-[1-Methylpyrrolidin-2- yl]pyridine, analogues thereof, precursors thereof or its derivatives, can be administered and reliably delivered to the desired destination within the body.
  • (S)-3-[1-Methylpyrrolidin-2-yl]pyridine analogues thereof, precursors thereof, or its derivatives can be used as a pharmaceutical in form of a homogeneous, viscous, semi-solid topical medication.
  • topical forms are presented as creams and/or gels and/or ointments and/or pastes.
  • they can contain one or more active ingredients dissolved or uniformly dispersed in a base or suitable excipients like emulsifiers, viscosity-increasing agents, antimicrobial agents, antioxidants, or stabilizing agents.
  • antimicrobial agents can be an advantage. Another advantage is that the medication neither irritates nor sensitizes the skin.
  • a smooth, inert, odourless, physically and chemically stable substance, compatible with the skin is preferred.
  • it comprises a consistency that spreads and softens easily.
  • a sterile condition is preferred.
  • (S)-3-[1-Methylpyrrolidin-2-yl]pyridine is intended as an ointment and/or lotion and/or cream and/or gel and/or tincture.
  • ointments are homogeneous, semi-solid preparations intended for external application to the skin or mucous membranes.
  • Ointments are formulated using hydrophobic, hydrophilic, or water-emulsifying bases to provide preparations that are immiscible, miscible, or emulsifiable with skin secretions.
  • Further ointments can be derived from hydrocarbon (fatty), absorption, water-removable, or water- soluble bases. Lotions are composed equally to ointments with the distinction that lotions are in general more liquid. Thereby lotions can be distributed more easily, especially on enlarged areas.
  • creams are homogeneous, semi-solid preparations consisting of opaque emulsion systems.
  • creams are intended for the application to the skin or certain mucous membranes in order to generate protective, therapeutic, or prophylactic purposes.
  • a cream is a soft, cosmetically acceptable type of preparation.
  • gels are usually homogeneous, clear, semi-solid preparations consisting of a liquid phase within a three-dimensional polymeric matrix with physical or sometimes chemical cross-linkage by means of suitable gelling agents.
  • gels are applied to the skin or certain mucous membranes for protective, therapeutic, or prophylactic purposes.
  • tinctures which are preferably administered with a device like a brush or rod in order to keep the target area sterile
  • (S)-3-[1-Methylpyrrolidin-2-yl]pyridine, analogues thereof, precursors thereof or its derivatives is intended for application on the skin, particularly on the mucosa.
  • the skin is an organ of the integumentary system of mammals consisting of multiple layers epithelial tissues with underlying muscles and organs.
  • the mucosa is a particular kind of skin, so called mucous membrane.
  • the mucosa is mostly of endodermal origin and is involved in absorption and recreation.
  • the mucosa of the present invention particularly refers to the oral and/or nasal cavity and/or the respiratory tract.
  • the stratum corneum constitutes the skin barrier for the diffusion of substances.
  • the application of (S)-3-[1-Methylpyrrolidin-2-yl]pyridine as a substance applied to the skin is able to transdermal penetrate the stratum corneum.
  • the solution is thereby applied as a topical medication. Therefore, the particles are of an adequate size for penetrating the skin. Said adequate size of particles regards to liquid and/or solid components within the topical medication. However, it is provided that the sizes are valid for the migration through the skin.
  • a preferred size is thereby approximately 1pm to approximately 15pm in diameter.
  • the size is between approx. 5pm to approx. 10pm in diameter.
  • the application of the substances to the skin allows an uptake into the bloodstream where the substance can affect the organism and thereby reduce the symptoms of diverse diseases. It is an advantage of an application to the skin that no digestion is required and the effective substance can be applied in the vicinity of the target tissue. The substance is directly transferred via the bloodstream to the predetermined pharmacological target location. Moreover, an application to the skin is fast drying, quickly absorbed and non irritating. Further, it is invisible after application and a reliable intake occurs. Further, applying a topical medication to the outer skin is an advantage for individuals needing a repeated administration of the substance since a topical medication can be applied locally without any effort of administering.
  • (S)-3-[1-Methylpyrrolidin-2-yl]pyridine, analogues thereof, precursors thereof or its derivatives contain a preservative and a vehicle substance.
  • the present delivery system contains a water-based and/or oil-based formulation.
  • (S)-3-[1-Methylpyrrolidin-2-yl]pyridine is a formulation, which is soluble in or miscible with a liquid carrier.
  • Another advantage is that the substance is soluble or miscible at room temperature.
  • (S)-3-[1-Methylpyrrolidin-2-yl]pyridine may be in form of a salt, which is solid at room temperature but can be dissolved in the liquid carrier, particularly in water and/or oil. Therefore, (S)-3-[1-Methylpyrrolidin-2-yl]pyridine like its salt formulations are generally soluble in water and/or oil. A process of mixing can occur in order to generate a homogeneous liquid mixture.
  • Beneath (S)-3-[1-Methylpyrrolidin-2-yl]pyridine also pharmacological analogues or derivatives or substances which mimic the effect of (S)-3- [1-Methylpyrrolidin-2-yl]pyridine, either alone or in combination with other active substances can be used.
  • the substance contains liposomes and/or triglycerides and/or ceramides and/or lecithin and/or squalene and/or dimethyl sulfoxide in order to be compatible with an application to the skin, particularly the mucosa.
  • (S)-3-[1-Methylpyrrolidin-2-yl]pyridine, analogues thereof, precursors thereof or its derivatives comprise a concentration of 0,3 mg/ml to 4,5 mg/ml, preferably 1,5 mg/ml to 3,0 mg/ml.
  • concentration of the active agent further depends on the liquidity at skin temperature (approximately 32°C) and/or the temperature of the body (approximately 36°C).
  • the delivery system applies a dose of the active agent of about 0,3 mg/ml to 4,5 mg/ml per unit dose.
  • 1,5 mg/ml to 3,0 mg/ml is applied.
  • the applied concentration of (S)-3-[1-Methylpyrrolidin-2-yl]pyridine is not toxic.
  • a cytotoxic compound can result in a variety of cell fates. The appearance of cytotoxic concentrations can result in necrosis (loss of membrane integrity) and thereby cell lysis, stopping cell growth and dividing or even apoptosis.
  • necrosis loss of membrane integrity
  • cytotoxicity assays are widely used in the pharmaceutical industry. Further indicators being investigated in order to determine the level of cytotoxicity are for example TNFa (tumor necrosis factor alpha), IFNy (Interferon gamma) or IL-6 (interleukin).
  • TNFa is a cell signaling protein mainly involved in systemic inflammation.
  • Cells that produce TNFa are mainly macrophages, lymphocytes, mast cells, or neurons.
  • IFNy is a soluble cytokine.
  • IFNy is a cytokine that is critical for immunity against viral, bacterial and protozoal infections. Thereby it is an important activator of macrophages and inducer of MHC (major histocompatibility complex) expression. IFNy has antiviral, immunoregulatory and anti-tumor properties.
  • IL-6 is an interleukin that acts as both a pro-inflammatory cytokine and an anti-inflammatory myokine. In mammalian IL-6 is secreted by T-cells and macrophages to stimulate an immune response.
  • (S)-3-[1-Methylpyrrolidin-2-yl]pyridine, analogues thereof, precursors thereof or its derivatives triggers stimulation of cholinergic receptors, particularly nicotinic receptors.
  • Nicotine acetylcholine receptors nAChR
  • the cholinergic receptors are forming ligand gated ion channels in the plasma membrane of the certain neuron. They are expressed on the presynaptic and postsynaptic side of the neuro muscular junctions. As neurotropic receptors they are directly linked to ion channels and thereby are not dependent on second messengers.
  • Neuron receptors are found in the central nervous system as well as in the peripheral nervous system of mammalians. Generally, ligand gated ion channels require the binding of a chemical messenger for opening.
  • the endogenous agonist is acetylcholine wherein they are also triggered by (S)-3-[1-Methylpyrrolidin-2-yl]pyridine, analogues thereof, precursors thereof or its derivatives.
  • (S)-3-[1-Methylpyrrolidin-2-yl]pyridine binds to nicotine cholinergic receptors can be regarded as a key energy source of the cell, as this is responsible for upregulating of energy. All nicotine cholinergic receptors produce excitatory postsynaptic effects.
  • (S)-3-[1-Methylpyrrolidin-2-yl]pyridine upregulates the release of endogenous alpha-MSH.
  • the melanocytes stimulating hormone (MSH) belong to peptide hormones that are produced in the central nervous system. These hormones stimulate the production inducing melanin by melanocytes in the skin and in the hair.
  • MSH melanocytes stimulating hormone
  • Alpha-MSH induces multiple responses in nearly all cells of mammalians, thereby significantly improving and also maintaining good health conditions.
  • Alpha-MSH is further related to chemical energy levels within the mammalian body and thereby fundamental for an optimal body performance.
  • the invention is (S)-3-[1-Methylpyrrolidin-2-yl]pyridine, analogues thereof, precursors thereof or its derivatives is used for the treatment of diseases related to pain. Further, these substances also modulate many disease pathologies like skin physiology, melanocytes function, nerve regeneration, behavior and learning as well as memory, obesity and energy metabolism, brain inflammation, autoimmune diseases, septic shock, endotoxemia, renal ischemic occlusion and reperfusion, mesenteric occlusion and reperfusion, diabetes, viral related diseases like H1N1 intoxications, viral related intoxications like Ebola, congenital mal formations and cancer as well as inflammatory diseases. Particularly, the substance is related to diseases as joint pain and further to diseases related to nerves as well as to skin. Mainly, these diseases can be treated in mammalians preferably in humans and/or animals.
  • (S)-3-[1-Methylpyrrolidin-2-yl]pyridine, analogues thereof, precursors thereof or its derivatives are administered every 24 hours.
  • the substance is administered every 12 hours, preferably every 6 hours.
  • the frequency of administration depends upon the variety of disease. In administration every 2 to 3 hours is likewise possible.
  • the frequency of application depends on the severity of the disease. An application every two or three hours can be an advantage.
  • the present invention further relates to a topical medication with a substrate which is applied on the skin of a human and/or animal body, wherein the substrate comprises (S)-3-[1- Methylpyrrolidin-2-yl]pyridine analogues thereof, precursors thereof, or its derivatives.
  • the topical medication is appropriate for transdermal delivery of an active substance, preferably (S)-3-[1-Methylpyrrolidin-2-yl]pyridine to an area of skin.
  • the topical medication administeres the pharmacological relevant substance, particularly (S)-3-[1-Methylpyrrolidin- 2-yl]pyridine in single dosages.
  • the application occurs over a certain area, particularly of skin and/or mucosa of at least 5 m 2 , preferably no more than about 100 m 2 .
  • the dose will be applied of an area of skin of approximately 20 cm 2 , depending on the area which is suffering from a disease.
  • a homogeneous mixture is obtained.
  • the topical medication should be protected from light, moisture, and damage due to handling and transportation.
  • the topical medication is stored in flexible tubes of suitable metal or plastic.
  • As an advantage preparations for nasal, aural, vaginal, or rectal use are supplied in containers adapted for appropriate delivery of the product to the site of application or are supplied with a suitable applicator.
  • a treatment with (S)-3-[1-Methylpyrrolidin-2-yl]pyridine of viral diseases like for example H1N1 was tested on chicken, infected with the H1N1 virus. Therefore, 30000 diseased chicken were divided into two groups of 15000.
  • One group was treated with (S)-3- [1-Methylpyrrolidin-2-yl]pyridine at doses of 0,002 mg/kg each 24 hours.
  • the other group represented the control group. 24 hours after treatment the treated group began to lay off eggs in contrary to the control group, which turned down the production of eggs.
  • the treatment against intoxication was tested related to mercury, CN, cadmium, arsenic, herbicides, pesticides.
  • mercury poisoning induces a generalized failure, typical to low levels of energy, so that the mortality level is high.
  • 6 in 8 rats died at the dose of 4,5 mg/kg of mercury (HgHCI).
  • HgHCI mercury
  • any of the organs edema and hemorrhage was examined.
  • Fig. 2a a diagram showing a cytotoxicity test with WI-38 cells treated with (S)-3-[1- Methylpyrrolidin-2-yl]pyridine
  • Fig. 2b a diagram showing a cytotoxicity test with A549 cells treated with (S)-3-[1- Methylpyrrolidin-2-yl]pyridine
  • Fig. 2c a diagram showing a cytotoxicity test with HS683 cells treated with (S)-3-[1-
  • Fig. 3 a diagram showing a cytotoxicity test of human PBLs treated with (S)-3-[1-
  • Fig. 4a a diagram showing the influence of (S)-3-[1-Methylpyrrolidin-2-yl]pyridine on the proliferation of WI-38 cells
  • Fig. 4b a diagram showing the influence of (S)-3-[1-Methylpyrrolidin-2-yl]pyridine on the proliferation of A549 cells
  • Fig. 4c a diagram showing the influence of (S)-3-[1-Methylpyrrolidin-2-yl]pyridine on the proliferation of HS683 cells
  • Fig. 5a a diagram showing the effect of (S)-3-[1-Methylpyrrolidin-2-yl]pyridine on
  • Fig. 5b a diagram showing the effect of (S)-3-[1-Methylpyrrolidin-2-yl]pyridine on
  • cytotoxicity tests were performed with three different cell lines (Fig. 2a, 2b, 2c):
  • HS683 human neuronal glioma cell line
  • MTT 3-[4,5-dimethyltiazol 2yl]-2,5-diphenyltetrazolium bromide
  • Cell lines (2x10 5 cell/ml) as well as leukocytes (2x10 6 cells/ml) were cultured in 96-well plates for 48 hours in the presence of various concentrations of (S)-3-[1-Methylpyrrolidin-2-yl]pyridine (5- 0,05 mg/ml). Next cells were treated with 20 pi of MTT.
  • LC50 LCso-lethal concentration, 50%-dose required to kill half of the cells after a specified test duration
  • PBLs peripheral blood
  • LCio and LCs were calculated.
  • three different concentrations of (S)-3-[1-Methylpyrrolidin- 2-yl]pyridine were selected for evaluation of the effect of cytokine production.
  • a proliferation test was prepared for the same three cell lines: WI-38, A549 and HS 683. 3x10 4 WI-38 cells and 2x10 4 A549 and HS 683. Cells were seeded into each wells in 96-well culture plates in appropriate culture medium with 10% FBS (fetal bovine serum). After 24 h incubation in 37°C/5%C0 2 medium were removed and replaced with tested concentrations of (S)-3-[1-Methylpyrrolidin-2-yl]pyridine in culture medium. After 96 hours incubation in 37°C/5%CC> 2 MTT assay was performed for establishing the cell viability.
  • FBS fetal bovine serum
  • Cytokine levels were determined using ELISA kits (BD Biosciences, USA) for human IFNy, TNF-a and IL-6 and DuoSet for human IL-3 (R&D Systems, USA) according to the producers’ instructions. The optical density was measured at 450 nm using a Multiskan RC spectrophotometric reader (Thermo Labsystems, USA), Cytokine concentrations were expressed in pg/ml.
  • the LC50 of (S)-3-[1-Methylpyrrolidin-2-yl]pyridine for a cell line WI-38 is 3,0 mg/ml
  • for the cell line A549 is 4,5 mg/ml
  • for the cell line HS-683 is 3,5 mg/ml.
  • the LC50 is a concentration of 7 mg/ml (S)-3-[1-Methylpyrrolidin-2-yl]pyridine.
  • the LC10 is in a concentration of 1 mg/ml and LC5 is in a concentration of 0,5 mg/ml (S)-3-[1- Methylpyrrolidin-2-yl]pyridine.
  • Figures 4a to 4c the influence of (S)-3-[1-Methylpyrrolidin-2-yl]pyridine on the proliferation of divers cell lines was investigated.
  • Figure 3a shows the effect on WI-38 cells.
  • WI-38 1,0 mg/ml of (S)-3-[1-Methylpyrrolidin-2-yl]pyridine inhibits 50% of the proliferation of these cells, whereby 4,5 mg/ml inhibits a proliferation of 99%.
  • For the cell line A549 a concentration of 2,0 mg/ml (S)-3-[1-Methylpyrrolidin-2-yl]pyridine inhibits 50% of the proliferation whereas the concentration of 5,5 mg/ml inhibits 99% of the proliferation.
  • the cytokine production is evaluated utilizing the effect of (S)-3-[1- Methylpyrrolidin-2-yl]pyridine on TNF-a production.
  • the preparation increases the level of cytokines in a dose-dependent manner. The effect was observed only for unstimulated human PBLs.

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  • Pharmacology & Pharmacy (AREA)
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  • Veterinary Medicine (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Abstract

L'invention se rapporte à la (S)-3-[1-méthylpyrrolidin-2-yl]pyridine, ses analogues, ses précurseurs ou ses dérivés, destinés à être utilisés en tant que produit pharmaceutique. Selon l'invention, la substance est un colloïde de fines particules solides et/ou liquides dans un fluide.
PCT/IB2020/061400 2019-12-02 2020-12-02 (s)-3-[1-méthylpyrrolidin-2-yl]pyridine, ses analogues, ses précurseurs ou ses dérivés, destinés à être utilisés en tant que produit pharmaceutique sous forme de médicament topique semi-solide, visqueux et homogène, et médicament topique Ceased WO2021111339A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP20820563.3A EP4069191A1 (fr) 2019-12-02 2020-12-02 (s)-3-[1-méthylpyrrolidin-2-yl]pyridine, ses analogues, ses précurseurs ou ses dérivés, destinés à être utilisés en tant que produit pharmaceutique sous forme de médicament topique semi-solide, visqueux et homogène, et médicament topique

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LULU101520 2019-12-02
LU101520A LU101520B1 (en) 2019-12-02 2019-12-02 (S)-3-[1-Methylpyrrolidin-2-yl]pyridine, analogues thereof, precursors thereof, or its derivatives, for the use as a pharmaceutical in form of a homogeneous, viscous, semi-solid topical medication and topical medication

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999015171A1 (fr) * 1997-09-25 1999-04-01 Pharmacia & Upjohn Ab Compositions de nicotine et leur procede de formulation
EP1222923A1 (fr) * 2001-01-12 2002-07-17 Izhak Blank Forme galenique transdermique contenant de la nicotine pour la desintoxication des fumeurs
EP2027860A1 (fr) * 2006-05-08 2009-02-25 Arturo Solis Herrera Utilisation de la nicotine, de ses analogues, précurseurs ou dérivés dans le traitement de différentes maladies susceptibles d'être enrayées avec l'administration de alpha-msh sou forme préventive ou thérapeutique

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999015171A1 (fr) * 1997-09-25 1999-04-01 Pharmacia & Upjohn Ab Compositions de nicotine et leur procede de formulation
EP1222923A1 (fr) * 2001-01-12 2002-07-17 Izhak Blank Forme galenique transdermique contenant de la nicotine pour la desintoxication des fumeurs
US6479076B2 (en) 2001-01-12 2002-11-12 Izhak Blank Nicotine delivery compositions
EP2027860A1 (fr) * 2006-05-08 2009-02-25 Arturo Solis Herrera Utilisation de la nicotine, de ses analogues, précurseurs ou dérivés dans le traitement de différentes maladies susceptibles d'être enrayées avec l'administration de alpha-msh sou forme préventive ou thérapeutique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
FLOOD PAMELA ET AL: "Intranasal nicotine for postoperative pain treatment", ANESTHESIOLOGY, AMERICAN SOCIETY OF ANESTHESIOLOGISTS, US, vol. 101, no. 6, 1 December 2004 (2004-12-01), pages 1417 - 1421, XP009116941, ISSN: 0003-3022, DOI: 10.1097/00000542-200412000-00023 *

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EP4069191A1 (fr) 2022-10-12

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