EP3758675A1 - Orale darreichungsform mit theobrominfreiem kakao - Google Patents
Orale darreichungsform mit theobrominfreiem kakaoInfo
- Publication number
- EP3758675A1 EP3758675A1 EP18709516.1A EP18709516A EP3758675A1 EP 3758675 A1 EP3758675 A1 EP 3758675A1 EP 18709516 A EP18709516 A EP 18709516A EP 3758675 A1 EP3758675 A1 EP 3758675A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- cocoa
- dosage form
- theobromine
- oral
- oral dosage
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 235000009470 Theobroma cacao Nutrition 0.000 title claims abstract description 89
- 239000006186 oral dosage form Substances 0.000 title claims description 16
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- 235000019613 sensory perceptions of taste Nutrition 0.000 claims abstract description 11
- 230000035923 taste sensation Effects 0.000 claims abstract description 11
- 244000299461 Theobroma cacao Species 0.000 claims description 91
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 claims description 48
- 239000004480 active ingredient Substances 0.000 claims description 25
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- 235000019658 bitter taste Nutrition 0.000 description 5
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- 229960002715 nicotine Drugs 0.000 description 4
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- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 3
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 235000019219 chocolate Nutrition 0.000 description 3
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 3
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- 229940110456 cocoa butter Drugs 0.000 description 3
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- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
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- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
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- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
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- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 description 1
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- 235000019157 thiamine Nutrition 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
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- TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 description 1
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- IRYJRGCIQBGHIV-UHFFFAOYSA-N trimethadione Chemical compound CN1C(=O)OC(C)(C)C1=O IRYJRGCIQBGHIV-UHFFFAOYSA-N 0.000 description 1
- 229960004453 trimethadione Drugs 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- 235000019583 umami taste Nutrition 0.000 description 1
- OMOMUFTZPTXCHP-UHFFFAOYSA-N valpromide Chemical compound CCCC(C(N)=O)CCC OMOMUFTZPTXCHP-UHFFFAOYSA-N 0.000 description 1
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- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
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- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
- A23G4/12—Chewing gum characterised by the composition containing organic or inorganic compounds containing microorganisms or enzymes; containing paramedical or dietetical agents, e.g. vitamins
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- 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
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- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
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- 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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Definitions
- the present invention relates to dosage forms for oral administration of pharmaceutical agents in which an unpleasant taste sensation is masked by the addition of theobromine-free cocoa.
- the dosage forms mentioned are dosage forms which release the active substance in the oropharynx.
- the taste sensations to be covered are attributable to one or more active pharmaceutical ingredients, one or more excipients, or a combination of pharmaceutical / active substance (s) with adjuvant (s).
- dosage forms are used in particular in patients who have difficulty swallowing dosage forms such as tablets or capsules, including geriatric and pediatric patients.
- Dosage forms in which the active substance is already taken up by the oral mucous membranes have the further advantage that the liver passage and there taking place metabolism of the drug can be avoided. An associated reduced therapeutic effect and increased side effects are thus prevented.
- absorption through the oral mucous membranes leads to a faster onset of action compared to administration forms in which the active substance is only taken up in the gastrointestinal tract.
- dosage forms for the suppression of attacks of vomiting during chemotherapy, as well as smoking cessation are therefore used such dosage forms, as there is a rapid onset of action is particularly desirable.
- the products SetoFilm®, Breakyl® and NiQuitin Strips® may be mentioned at this point, which have the abovementioned advantages.
- Breakyl® a buccal film containing the opioid fentanyl, dissolves in the oral cavity within 15 to 30 minutes after application, during which time the active ingredient can resorb into the oral mucosa.
- the oral film SetoFilm® is placed on the tongue and dissolves within seconds.
- the drug is swallowed together with the saliva and absorbed in the gastrointestinal tract.
- NiQuitin Strips®, orally administered films dissolve in the mouth within three minutes.
- the active ingredient, nicotine is sometimes taken up via the mucous membranes, sometimes after swallowing also gastrointestinal.
- Previously known measures to improve the taste of oral pharmaceutical preparations can be subdivided into the following three groups: a) masking by cognitive deception: addition of sweetener and flavorings; b) Masking by reducing the concentration of free drug molecules: Formation of molecular complexes (including cyclodextrin inclusion compounds), formation of ion exchange complexes, use of another counterion, formation of nonionic forms of the drug, Befilmung the particles in one Suspension; c) Masking by lowering the receptor contact time: increase in viscosity, use of a lipophilic vehicle, formation of particulate solutions (for example, suspension). A combination of these measures can also be used.
- DE 69505361 discloses chewable tablets with the active ingredients troxerutin, calcium carbonate, calcium phosphate, arginine aspartate, arginine glutamate, amoxicillin and combinations thereof.
- cocoa powder is added to the chewable tablets. This also comes next to the taste masking the function of a binder.
- the proportion of the cocoa powder relative to the total mass of the tablet is given as a range from 1 to 50% by weight, preferably from 14 to 30% by weight. In the embodiments, the proportion is finally from 25 to 46 wt .-%.
- the formulations include one or more sweeteners (aspartame, mannitol, sorbitol) and various flavorings.
- US 2003/0087937 A1 describes pharmaceutical preparations for oral administration, including nicotine.
- the preparations release the active substance in the oral cavity, where it is absorbed through the oral mucosa.
- the bitter taste of the active ingredient is masked by a preferred amount of cocoa powder of 17-50% by weight.
- the formulations for oral administration disclosed therein have a proportion of cocoa powder of at least 17% by weight and the cocoa powder functions not only as a taste masking agent but also as a binding agent.
- this high proportion of at least 17% by weight of cocoa powder limits the formulation development to a high degree.
- the formulation developer has little creative freedom for other auxiliaries in order to be able to sufficiently control other properties of the dosage form, in particular the release profile and the stability.
- film formulations containing more than 15% by weight of cocoa powder for example, increased brittleness of the films occurs, which thus does not fulfill regulatory requirements and can not be used as medicaments.
- smaller amounts of cocoa powder are insufficient to sufficiently mask a negative taste sensation.
- the object of the present invention was to provide stable dosage forms for oral administration of pharmaceutical active substances in which an unpleasant taste sensation, caused by release of the pharmaceutical active substance and / or the excipients in the mouth and throat of the patient covered by taste masking.
- the object has been achieved by the use of theobromine-free cocoa, which covers the unpleasant taste from the active ingredient (s), excipient (s) or combinations thereof.
- the taste masking takes place already at a proportion of less than 15 wt .-%, so that the formulation development is not affected.
- dosage forms which, in addition to the theobromine-free cocoa, contain less than 5% by weight of another taste corrigant.
- the present invention relates to the recovery of theobromine-free cocoa which can be used to reduce unpleasant taste sensations in pharmaceutical products.
- Dosage forms consist of a mixture of pharmaceutical active substance (s) and excipients that has been processed in a particular way. The different forms of administration can be classified according to the place of administration.
- Oral dosage forms are taken by mouth, such as tablets or capsules. These are swallowed and the pharmaceutical active substance contained is released in the gastrointestinal tract and absorbed.
- Other oral dosage forms release the active pharmaceutical ingredient already in the mouth and throat, where it is either swallowed together with the saliva and taken up in the gastrointestinal tract, or is already absorbed through the mucous membranes in the oral and pharyngeal area - transmucosal.
- oral dosage forms are known which lead to an active ingredient intake in both places.
- the solid dosage forms that deliver the active pharmaceutical ingredient in the oropharynx include chewable tablets, conventional sublingual and buccal tablets, mucoadhesive sublingual and buccal tablets, orodispersible tablets, oral lyophilisates, oral films, lozenges and tablets, oral therapeutic systems and chewing gum.
- Chewable tablets are tablets that are bitten in the mouth, chewed and then swallowed. They are especially suitable for children and patients who can not or will not swallow ordinary tablets.
- Orodispersible tablets differ from conventional tablets in their very short disintegration time in saliva. According to the Ph. Eur., These should disintegrate in up to three minutes in 8 minutes, according to the FDA, in up to 30 seconds. In contrast to oral lyophilisates and films, the orodispersible tablets have a high mechanical stability. Oral lyophilisates, also commonly referred to as orodispersible tablets, are prepared by freeze-drying of drug / excipient dispersions as platelets for oral use. These break down on contact with small amounts of saliva within a few seconds and thereby release the pharmaceutical active ingredient. The pharmaceutical active substance contained is generally not intended for absorption via the oral mucosa, but is taken up in the gastrointestinal tract. However, some amount of active ingredient can also be absorbed through the oral mucosa. As a rule, the lyophilisates are administered under the tongue (sublingually) or on the tongue (lingually).
- orodispersible films melt films, thin strips, wafers
- mucoadhesive films are thin, flexible dosage forms that rapidly disintegrate on contact with saliva in the oral cavity.
- Mucoadhesive films adhere to the oral mucosa and release the pharmaceutical agent at the desired site of application. Furthermore, they do not dissolve immediately, but retain their shape and mechanical strength for a while.
- an oral therapeutic system is the product Actiq®.
- the active ingredient fentanyl citrate is incorporated in a water-soluble powder compact which is fixed to the end of a rod-shaped plastic applicator. The patient moves the compact back and forth with the applicator on the inside of the cheek. This dissolves and releases the fentanyl rapidly, which is absorbed through the oral mucosa.
- solid or semi-solid dosage forms such as e.g. medicated gels that are taken orally and release the pharmaceutical agent in the oropharynx.
- the pharmaceutical active substance contained is released by chewing and then absorbed through the oral mucous membranes.
- a pharmaceutically active substance is the pharmacologically active substance in a dosage form which is responsible for its therapeutic effect.
- Excipients have no therapeutic effect and are required for a drug to be processed into a drug form, administered and absorbed by the body.
- the various pharmaceutically used excipients are classified according to their function; Examples of such classes of excipients are: disintegrants, binders, solvents, fillers, emulsifiers, solubilizers, buffers, antioxidants, preservatives, flavoring agents, absorption accelerators, film formers.
- taste correctors or, synonymously used taste masking agents are referred to auxiliaries which improve the taste of a dosage form by masking or covering an unpleasant taste. These include, for example, sweeteners and flavorings.
- the sweeteners are subdivided into sugars, sugar substitutes and sweeteners.
- the sugar substitutes include, for example, the sugar alcohols glucitol, mannitol, maltitol and xylitol and fructose.
- Sweeteners include sucrose, acesulfame-K, matrium cyclamate, glycyrrhizin, aspartame, dulcine, saccharin, stevioside, naringin dihydrochalcone, aspartame acesulfame salt, sucralose, monellin, thaumatin, neohesperidine dihydrochalcone, and neotame.
- essential oils are used as generallyskorrigens.
- the essential oils include lipophilic, volatile plant ingredients such as u.a. Peppermint oil, lavender oil and chamomile oil. Menthol, the ingredient of peppermint oil, is also used as a flavoring agent.
- flavorings are natural or synthetically produced flavors and essences with the taste of: mint, lemon, orange, peppermint, eucalyptus, apple, cherry, strawberry, pineapple, caramel, tutti-frutti, honey, fruit salad, orange, tangerine, raspberry, coconut, cocoa, vanilla, anise, geraniol, almond, honey, liquorice or mixtures thereof.
- Taste sensations are individually different. In principle, a distinction is made between five basic flavors: sweet, salty, umami, sour and bitter. While the last two are generally perceived as being unpleasant, the others can also appear to an extent that is perceived as unpleasant and should therefore be avoided.
- Cocoa is the name given to the finely ground product obtained from the processed seeds of the cocoa tree and used as a raw material for the production of chocolate and chocolate products, as well as cocoa drinks.
- the solid tires are cut fruit from the tree.
- the cocoa seeds are dissolved together with the fruit pulp from the shell and subjected to a fermentation lasting several days. Fermentation involves various hydrolytic and enzymatic reactions, which are important for the quality of the cocoa beans, especially for the cocoa flavor.
- the occurring polyphenols are oxidized and polymerized, resulting in condensed tannins and the Phlobaphene responsible for the brown coloration of the cocoa.
- the fermented beans are dried in the sun or in dryers to a water content of ⁇ 8% and freed of foreign substances. During subsequent roasting, the water content drops to 2.5-3%. Acetic acid, acetic acid ester and other undesirable flavors are removed and microbial load is reduced. After cooling, the roasted beans are broken into cocoa fruit and the peel and sprouts are removed. Subsequently, the cocoa grains are crushed and ground, forming the homogeneous, flowable cocoa mass. The cocoa break can then be digested alkaline. The digestion causes the swelling of the starch, the acidic parts are neutralized and the cell structure is loosened. The cocoa mass thus obtained contains, like normal cocoa mass, 52-58% cocoa butter.
- cocoa powder with at least 20% cocoa butter content and highly deoiled or low-fat cocoa powder with less than 20% cocoa butter content in relation to the dry matter, depending on the fat content.
- Theobromine is the chemical compound 3,7-dimethylxanthine-3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione and the main alkaloid of cocoa. Together with the polyphenols contained in cocoa and the piperazinediones formed during the roasting process, theobromine is blamed for the typically bitter taste of cocoa. In cocoa beans, theobromine is present at 1.0-2.5% by weight, in cocoa powder at 1.4-3.0% by weight and in cocoa shells at 1.3-2.1% by weight.
- cocoa Compared to pure theobromine cocoa produces only an entertaining bitter taste sensation. This is because other cocoa ingredients mask the bitter taste of the theobromine.
- cocoa-free cocoa cocoa to which by extraction at least 80%, preferably at least 90%, most preferably at least 95% of the naturally contained theobromine has been withdrawn.
- the result is a theobromine content of at most 0.6% by weight, preferably at most 0.3% by weight, most preferably at most 0.15% by weight of the theobromine-free cocoa.
- the extraction of the theobromine from cocoa powder, beans or peels can be done with lime milk.
- the extraction of the theobromine from the said starting materials can also be carried out with supercritical carbon dioxide (C0 2 ).
- the theobromine-free cocoa contains theobromine in a proportion of less than 0.6 wt .-%, preferably less than 0.3 wt .-%, more preferably less than 0.15 wt .-%.
- the cocoa contains theobromine in a proportion of less than 0.6 wt .-%, preferably less than 0.3 wt .-%, more preferably less than 0.15 wt .-%.
- the oral dosage forms are characterized in that the theobromine-free cocoa has a content of less than 0.6% by weight of theobromine, preferably less than 0.3% by weight of theobromine, more preferably less than 0, Contains 15 wt .-% of theobromine.
- nozzles with an internal volume of approx. 6 l are each charged with approx. 1 kg of cocoa beans (alternatively, cocoa powder or shells can also be used).
- cocoa powder or shells can also be used.
- To the beans in the first two nozzles is poured 3.5 liter of drinking water and milk of lime per 100 g of quicklime per nozzle, stirred well with a glass rod and filtered after 12 hours of service life.
- the filtrates are combined in a 50 l round bottom flask.
- the residues are returned to ports 1 and 2, where they are again mixed with 3.5 1 of water, but reduced lime to 10 g of quicklime per nozzle. It is stirred well again with a glass rod and filtered after 12 hours of service life.
- the filtrate is added to the 50 1 flask.
- cocoa peel Fa. Caelo, Ch.-B .: 14096914 (alternatively, cocoa beans or cocoa powder can be used) were slurried in 310 g l0% calcium oxide suspension and 300 g of water and allowed to stand overnight.
- the residue was slurried in 100 g of 10% strength calcium oxide suspension and 600 g of water and allowed to stand overnight. It was again filtered off with suction and the residue slurried in 500 g of water. After suction, the residue had a clear white coating of calcium oxide or calcium hydroxide. Therefore, the residue was concentrated in 100 g.
- theobromine was detected by thin-layer chromatography (eluent: methylene chloride: ethanol: acetic acid 88: 10: 2, plate: silica gel 60F254; detection: UV).
- titanium dioxide, glycerol, cocoa, acesulfame-K, menthol and polyoxyethylene sorbitan monooleate be added and stirred until homogeneous.
- a taste test in a small panel of volunteers showed that a taste-masking effect of the cocoa is present only in formulation 3.3, which contains a cocoa content of 15 wt .-%.
- the production of films with higher cocoa content caused breaks in the film.
- Example 4 formulations according to the invention with the active ingredient ondansetron
- Formulations of oral films containing ondansetron were prepared.
- the formulations correspond to the formulation of the commercial product Setofilm® with the exception that instead of the sweetener acesulfame K and the flavoring agent menthol theobromine-free cocoa is included.
- Table 2 Film formulations containing ondansetron and theobromine-free cocoa powder.
- Formulation 4.1 which has a content of 5% by weight of theobromine-free cocoa, there is a masking of the unpleasant, bitter taste of the active substance ondansetron.
- the mass is spread as a thin film on a process film and dried at 50 ° C for 15 minutes. The dry film is then separated.
- Example 6 (formulations with the active ingredient Rizatrip tan)
- the mass is spread as a thin film on a process film and dried at 50 ° C for 15 minutes. The dry film is then separated.
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Abstract
Description
Claims
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Application Number | Priority Date | Filing Date | Title |
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PCT/EP2018/055105 WO2019166098A1 (de) | 2018-03-01 | 2018-03-01 | Orale darreichungsform mit theobrominfreiem kakao |
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EP3758675A1 true EP3758675A1 (de) | 2021-01-06 |
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EP18709516.1A Withdrawn EP3758675A1 (de) | 2018-03-01 | 2018-03-01 | Orale darreichungsform mit theobrominfreiem kakao |
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US (1) | US20210000963A1 (de) |
EP (1) | EP3758675A1 (de) |
JP (1) | JP7182639B2 (de) |
CN (1) | CN111787906A (de) |
BR (1) | BR112020017468A2 (de) |
CA (1) | CA3092458C (de) |
WO (1) | WO2019166098A1 (de) |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1851872A (en) * | 1926-04-12 | 1932-03-29 | Firm C H Boehringer Sohn | Method for obtaining theobromine |
US1947717A (en) * | 1929-11-13 | 1934-02-20 | Battle Creek Food Company | Cocoa product and process of making same |
US2118129A (en) * | 1936-04-06 | 1938-05-24 | Rockwood & Co | Treatment of cocoa products |
US4390698A (en) * | 1981-05-21 | 1983-06-28 | Societe D'assistance Technique Pour Produits Nestle S.A. | Detheobromination of cocoa |
FR2717387B1 (fr) | 1994-03-17 | 1996-10-18 | Hi Pharmtech | Procédé de fabrication de comprimés à croquer à base de troxérutine, de carbonate de calcium, de phosphate de calcium, d'aspartate d'arginine, de glutamate d'arginine d'amoxicilline. |
US20030087937A1 (en) | 2001-10-15 | 2003-05-08 | Nils-Olof Lindberg | Nicotine and cocoa powder compositions |
SE0202365D0 (sv) | 2002-08-05 | 2002-08-05 | Pharmacia Ab | New formulation and use thereof |
SE0300831D0 (sv) | 2003-03-26 | 2003-03-26 | Pharmacia Ab | New formulations and use therof |
US8580830B2 (en) | 2006-10-02 | 2013-11-12 | Labtec Gmbh | Non-mucoadhesive film dosage forms |
US20080286340A1 (en) * | 2007-05-16 | 2008-11-20 | Sven-Borje Andersson | Buffered nicotine containing products |
CN103583781B (zh) * | 2013-11-01 | 2015-11-25 | 阳波 | 咖啡味甲硝唑口香糖 |
-
2018
- 2018-03-01 JP JP2020545561A patent/JP7182639B2/ja active Active
- 2018-03-01 CN CN201880090587.6A patent/CN111787906A/zh active Pending
- 2018-03-01 CA CA3092458A patent/CA3092458C/en active Active
- 2018-03-01 EP EP18709516.1A patent/EP3758675A1/de not_active Withdrawn
- 2018-03-01 WO PCT/EP2018/055105 patent/WO2019166098A1/de active Application Filing
- 2018-03-01 BR BR112020017468-8A patent/BR112020017468A2/pt unknown
- 2018-03-01 US US16/977,018 patent/US20210000963A1/en active Pending
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CA3092458C (en) | 2024-01-30 |
WO2019166098A1 (de) | 2019-09-06 |
US20210000963A1 (en) | 2021-01-07 |
JP7182639B2 (ja) | 2022-12-02 |
BR112020017468A2 (pt) | 2020-12-22 |
JP2021515008A (ja) | 2021-06-17 |
CA3092458A1 (en) | 2019-09-06 |
CN111787906A (zh) | 2020-10-16 |
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