WO2003053427A1 - Utilisation de (+)-(1s,2s)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)phenol en tant qu'anti-emetique - Google Patents
Utilisation de (+)-(1s,2s)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)phenol en tant qu'anti-emetique Download PDFInfo
- Publication number
- WO2003053427A1 WO2003053427A1 PCT/EP2002/014636 EP0214636W WO03053427A1 WO 2003053427 A1 WO2003053427 A1 WO 2003053427A1 EP 0214636 W EP0214636 W EP 0214636W WO 03053427 A1 WO03053427 A1 WO 03053427A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- active ingredient
- dimethylamino
- ethyl
- phenol
- methyl
- Prior art date
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Classifications
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/485—Morphinan derivatives, e.g. morphine, codeine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
Definitions
- This object is achieved by using (+) - (1 S, 2S) -3- (3-dimethylamino-1-ethyl-2-methyl-propyl) phenol in the form of its base or in the form of one of its physiologically tolerable salts and / or Solvate for the manufacture of a medicament for the prevention and / or therapy of nausea and / or vomiting.
- (+) - (1S, 2S) -3- (3-dimethylamino-1-ethyl-2-methyl-propyl) phenol is also referred to as "active ingredient (I)", which does not only refer to the free base, but also relates to one of its physiologically tolerable salts and / or solvates.
- dimethylamino-1-ethyl-2-methyl-propyl phenol In contrast to morphine (and many other opioid analgesics), dimethylamino-1-ethyl-2-methyl-propyl) phenol not only does not have an emetic effect, ie does not cause nausea or vomiting, but also has an antiemetic effect, ie the emetic effect of known emesis Triggers like morphine or emetin (Ipecacuanha extract) cancels out. This antiemetic effect is not only found at relatively high doses, but also over the entire dose range examined, i.e. also when small doses are administered. These results are confirmed by tests on ferrets, a standard model for the detection of emetic and antiemetic active properties (see, for example, C.
- the further antiemetic active ingredient is, in particular, metoclopramide, domperidone, haloperidol, fluphenazine, sulpiride, tiapride, benzoquinamide, diazepam, betamethasone, dexamethasone, prednisolone, cyclizine, hydroxyzine, diphenhydramine, scopolamine, chlorpromazine, promethidolperperol, perphenol Bemesetron and particularly preferably ondansetron, bemesetron, benzapride, zacoprid, dazoprid, p-chlorophenylalanine, granisetron, tropisetron or dolasetron. Most preferred as another antiemetic agent is ondansetron.
- Another advantage of the present invention is that the active ingredient (I) exhibits its anti-emetic effect even when a cytostatic active ingredient is administered simultaneously, previously or subsequently.
- a cytostatic active ingredient is administered simultaneously, previously or subsequently.
- emesis model i.v. of 10 mg / kg cisplatin - agent of choice for the chemotherapy of many cancers - to ferrets by administering (+) - (1 S, 2S) -3- (3-dimethylamino-1-ethyl-2-methyl-propyl) phenol (as hydrochloride) suppresses the vomiting usually caused by cisplatin.
- (+) - (1 S, 2S) -3- (3-dimethylamino-1-ethyl-2-methyl-propyl) phenol suitable for the prophylaxis and therapy of nausea and emesis accompanying cancer treatment with cytostatics (chemotherapy).
- the active ingredient (I) is used as an antiemetic in addition to at least one cytostatic agent.
- the cytostatic is preferably carboplatin,
- Doxorubicin, cyclophosphamide, taxol or especially cisplatin Doxorubicin, cyclophosphamide, taxol or especially cisplatin.
- compositions for the prophylaxis and / or therapy of nausea and / or vomiting containing (+) - (1 S, 2S) -3- (3-dimethylamino-1-ethyl-2-methyl-propyl) ) phenol in the form of its base or in the form of one of its physiologically acceptable salts and / or solvates and one or more pharmaceutical adjuvants.
- compositions preferably comprise at least one further active ingredient for the prevention and / or therapy of nausea and / or vomiting.
- a suitable further antiemetic active ingredient is preferably selected from the following active ingredient groups: dopamine antagonists, benzodiazepines, corticosteroids, antihistamines, anticholinergics, phenothiazines, butyrophenones, benzamides and in particular 5-HT 3 antagonists.
- dopamine antagonists preferably selected from the following active ingredient groups: dopamine antagonists, benzodiazepines, corticosteroids, antihistamines, anticholinergics, phenothiazines, butyrophenones, benzamides and in particular 5-HT 3 antagonists.
- dopamine antagonists preferably selected from the following active ingredient groups: dopamine antagonists, benzodiazepines, corticosteroids, antihistamines, anticholinergics, phenothiazines, butyrophenones, benzamides and in particular
- the active substance is in particular metoclopramide, domperidone, haloperidol, fluphenazine, sulpiride, tiapride, benzoquinamide, diazepam, betamethasone, dexamethasone, prednisolone, cyclizine, hydroxyzine, diphenhydramine, scopolamine, chlorpromazine, promethazine, perphenazine, prochlorperazine, particularly preferred, drochloronazine, prochlorperazine around ondansetron, bemesetron, benzapride, zacoprid, dazopride, p-chlorophenylalanine, granisetron, tropisetron or dolasetron. Most preferred as another antiemetic agent is ondansetron.
- this additionally comprises an opioid.
- This additional opioid active ingredient is preferably selected from the group comprising morphine, hydromorphone, fentanyl, buprenorphine, tilidine and tramadol.
- Pharmaceutically acceptable salts or physiologically acceptable salts in the sense of this invention are such salts of the active ingredient (+) - (1S, 2S) -3- (3-dimethylamino-1-ethyl-2-methyl-propyl) phenol, which are used in pharmaceutical applications physiologically - especially when used on mammals and / or humans - are compatible.
- Such pharmaceutically acceptable salts can be formed, for example, with inorganic or organic acids.
- Hydrochloride formation is particularly preferred, which can be brought about, for example, by adding trimethylsilyl chloride (TMSCI) to the active ingredient base (I) dissolved in a suitable organic solvent.
- TMSCI trimethylsilyl chloride
- the active ingredient (I) and its physiologically acceptable salts can also be present as solvates, in particular hydrates; the hydrates can be obtained, for example, by crystallization from an aqueous solution.
- auxiliaries such as carrier materials, fillers, solvents, diluents, surface-active substances, dyes, preservatives, disintegrants, lubricants, lubricants, flavors and / or binders.
- auxiliaries can be, for example: water, ethanol, 2-propanol, glycerol, ethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, glucose, fructose, lactose, sucrose, dextrose, molasses, starch, modified starch, gelatin, Sorbitol, inositol, mannitol, microcrystalline cellulose, methyl cellulose, carboxymethyl cellulose, cellulose acetate, shellac, cetyl alcohol, polyvinyl pyrrolidone, paraffins, waxes, natural and synthetic gums, acacia gum, alginates, dextran, saturated and unsaturated fatty acids, stearate, stearate,
- Silicon dioxide titanium oxide, titanium dioxide, magnesium sulfate, zinc sulfate, calcium sulfate, potash, calcium phosphate, dicalcium phosphate, potassium bromide, potassium iodide, talc, kaolin, pectin, crospovidone, agar and bentonite.
- excipients and the amounts to be used depends on whether the medicament is to be administered orally, subcutaneously, parenterally, intravenously, pulmonally, intraperitoneally, transdermally, intramuscularly, nasally, buccally, rectally or in another suitable manner.
- the following are suitable for oral application: Preparations in the form of tablets, dragees, capsules, granules, drops, juices and syrups, for parenteral, topical and inhalation application solutions, suspensions, easily reconstitutable powders for inhalation and sprays.
- the active ingredient (I) is e.g. in a depot in dissolved form or in a plaster, optionally with the addition of agents which promote skin penetration.
- compositions according to the invention which, in addition to (+) - (1 S, 2S) -3- (3-dimethylamino-1-ethyl-2-methyl-propyl) phenol, in The form of its base or in the form of one of its physiologically tolerable salts and / or solvates, a further antiemetic or an additional opioid or an additional cytostatic agent, can be designed in such a way that these combination preparations release the active compounds present at the same time or almost simultaneously, or control the release in such a way that one of the active ingredients, for example the additional opioid or the additional cytostatic agent, is released and the release of the other active ingredient, for example the active ingredient (I), is delayed, ie occurs later, in order to achieve the desired effect of all active ingredients contained in the composition
- the medicaments and pharmaceutical compositions according to the invention are produced with the aid of means, devices, methods and processes which are well known in the art of pharmaceutical formulation, as described, for example, in "Remington 's Pharmaceutical Sciences", published by AR Gennaro, 17th Ed., Mack Publishing Company, Easton, Pa. (1985), in particular in Part 8, Chapters 76 to 93.
- a solid formulation such as a tablet
- the active ingredient of the drug ie (+) - (1 S, 2S) -3- (3-dimethylamino-1-ethyl-2-methyl-propyl) phenol or one of its physiologically acceptable salts and / or solvates
- a pharmaceutical carrier for example conventional tablet ingredients, such as corn starch, lactose, sucrose, sorbitol, talc, magnesium stearate, dicalcium phosphate or pharmaceutically acceptable gums
- pharmaceutical diluents such as water, for example, granulated to give a solid Form composition comprising a compound of the invention or a pharmaceutically acceptable Contains salt in a homogeneous distribution.
- a homogeneous distribution is understood here to mean that the active ingredient is uniformly distributed over the entire composition, so that it can be easily divided into equally effective unit dose forms, such as tablets, pills or capsules.
- the solid composition is then divided into unit dose forms.
- the tablets or pills of the medicament according to the invention or of the compositions according to the invention can also be coated or compounded in some other way in order to provide a dosage form with delayed release.
- Suitable coating agents include polymeric acids and mixtures of polymeric acids with materials such as shellac, cetyl alcohol and / or cellulose acetate.
- Another object of the invention relates to a method for the treatment of emesis and / or nausea in a mammal and / or human, which is characterized in that a therapeutically effective amount of the active ingredient (I) in the form of its base or in the form of one of its physiologically tolerable Salts and / or solvates, optionally in combination with a further antiemetic or an additional opioid or an additional cytostatic agent, is administered.
- the amount of active ingredient to be administered to the patient varies and depends on the weight, age and history of the patient, as well as on the type of application, the indication and the severity of the disease. Usually 0.1 to 1000 mg, in particular 1 to 100 mg, preferably 2 to 50 mg of the active ingredient (I) are applied.
- Morphin HCI (RBI Batch 2883/6) in a dose of 0.1 mg / kg i.v. or Ipecacuanha fluid extract, DAC 98 (adjusted to 2% emetin) from Synpharm (batch 9906B067) orally administered according to a dose of 2 mg / kg emetin.
- test result is shown as the group mean (x ⁇ sx) of the events in the reacting animals.
- percentage of animals with retches and vomits is also calculated.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Abstract
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2002361185A AU2002361185A1 (en) | 2001-12-21 | 2002-12-20 | Use of (+)-(1s,2s)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)phenol as anti-emetic agent |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10163421A DE10163421A1 (de) | 2001-12-21 | 2001-12-21 | Verwendung von (+)-(1S,2S)-3-(3-Dimethylamino-1-ethyl-2-methyl-propyl)phenol als Antiemetikum |
DE10163421.8 | 2001-12-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2003053427A1 true WO2003053427A1 (fr) | 2003-07-03 |
Family
ID=7710471
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2002/014636 WO2003053427A1 (fr) | 2001-12-21 | 2002-12-20 | Utilisation de (+)-(1s,2s)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)phenol en tant qu'anti-emetique |
Country Status (3)
Country | Link |
---|---|
AU (1) | AU2002361185A1 (fr) |
DE (1) | DE10163421A1 (fr) |
WO (1) | WO2003053427A1 (fr) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102005013726A1 (de) * | 2005-03-22 | 2006-09-28 | Grünenthal GmbH | Transdermale therapeutische Systeme mit verbesserter Verträglichkeit |
WO2011157391A1 (fr) * | 2010-06-15 | 2011-12-22 | Grünenthal GmbH | Combinaison pharmaceutique pour le traitement de la douleur |
WO2013017233A1 (fr) * | 2011-07-29 | 2013-02-07 | Grünenthal GmbH | Administration intrathécale ou épidurale de 3-[(1s,2s)-3-(diméthylamino)-1-éthyl-2-méthyl-propyl]-phénol |
EP2796171A1 (fr) * | 2010-03-11 | 2014-10-29 | Acacia Pharma Limited | Utilisation de l'amisulpride pour le traitement des nausées et vomissements induits par les opiacés |
AU2014202535B2 (en) * | 2010-03-11 | 2016-05-26 | Acacia Pharma Limited | The use of amisulpride as an anti-emetic |
AU2016216578B2 (en) * | 2010-03-11 | 2017-11-23 | Acacia Pharma Limited | The use of amisulpride as an anti-emetic |
US12005042B2 (en) | 2017-02-10 | 2024-06-11 | Acacia Pharma Ltd. | Rescue treatment of post operative nausea and vomiting |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0693475A1 (fr) * | 1994-07-23 | 1996-01-24 | Grünenthal GmbH | Dérivés propane 1-phényl-3-diméthylamino à activité pharmocologique |
WO2002067916A2 (fr) * | 2001-02-28 | 2002-09-06 | Grünenthal GmbH | Sels pharmaceutiques |
-
2001
- 2001-12-21 DE DE10163421A patent/DE10163421A1/de not_active Withdrawn
-
2002
- 2002-12-20 AU AU2002361185A patent/AU2002361185A1/en not_active Abandoned
- 2002-12-20 WO PCT/EP2002/014636 patent/WO2003053427A1/fr not_active Application Discontinuation
Patent Citations (3)
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EP0693475A1 (fr) * | 1994-07-23 | 1996-01-24 | Grünenthal GmbH | Dérivés propane 1-phényl-3-diméthylamino à activité pharmocologique |
WO2002067916A2 (fr) * | 2001-02-28 | 2002-09-06 | Grünenthal GmbH | Sels pharmaceutiques |
WO2002067651A2 (fr) * | 2001-02-28 | 2002-09-06 | Grünenthal GmbH | Sels pharmaceutiques |
Non-Patent Citations (3)
Title |
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HERRSTEDT J: "Potential new agents in the prophylaxis and treatment of chemotherapy-induced emesis", EUROPEAN JOURNAL OF CANCER, PERGAMON PRESS, OXFORD, GB, vol. 37, no. 7, May 2001 (2001-05-01), pages 823 - 825, XP004233940, ISSN: 0959-8049 * |
OETTLE HELMUT ET AL: "Treatment of chemotherapy-induced nausea and vomiting.", JOURNAL OF CANCER RESEARCH AND CLINICAL ONCOLOGY, vol. 127, no. 6, 2001, pages 340 - 345, XP001146210, ISSN: 0171-5216 * |
TRAMER M R: "A rational approach to the control of postoperative nausea and vomiting: Evidence from systematic reviews. Part II. Recommendations for prevention and treatment, and research agenda.", ACTA ANAESTHESIOLOGICA SCANDINAVICA, vol. 45, no. 1, January 2001 (2001-01-01), pages 14 - 19, XP001146209, ISSN: 0001-5172 * |
Cited By (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102005013726A1 (de) * | 2005-03-22 | 2006-09-28 | Grünenthal GmbH | Transdermale therapeutische Systeme mit verbesserter Verträglichkeit |
US9119836B2 (en) | 2010-03-11 | 2015-09-01 | Acacia Pharma Limited | Use of amisulpride as an anti-emetic |
US10525033B2 (en) | 2010-03-11 | 2020-01-07 | Acacia Pharma Limited | Use of amisulpride as an anti-emetic |
US10085970B2 (en) | 2010-03-11 | 2018-10-02 | Acacia Pharma Limited | Use of amisulpride as an anti-emetic |
US9889118B2 (en) | 2010-03-11 | 2018-02-13 | Acacia Pharma Limited | Use of amisulpride as an anti-emetic |
AU2016216578B2 (en) * | 2010-03-11 | 2017-11-23 | Acacia Pharma Limited | The use of amisulpride as an anti-emetic |
US9545426B2 (en) | 2010-03-11 | 2017-01-17 | Acacia Pharma Limited | Use of amisulpride as an anti-emetic |
AU2014202535B2 (en) * | 2010-03-11 | 2016-05-26 | Acacia Pharma Limited | The use of amisulpride as an anti-emetic |
EP2796171A1 (fr) * | 2010-03-11 | 2014-10-29 | Acacia Pharma Limited | Utilisation de l'amisulpride pour le traitement des nausées et vomissements induits par les opiacés |
US9084765B2 (en) | 2010-03-11 | 2015-07-21 | Acacia Pharma Limited | Use of amisulpride as an anti-emetic |
EP2992877A1 (fr) * | 2010-06-15 | 2016-03-09 | Grünenthal GmbH | Combinaison pharmaceutique pour le traitement de la douleur |
CN103108631A (zh) * | 2010-06-15 | 2013-05-15 | 格吕伦塔尔有限公司 | 用于治疗疼痛的联合药物 |
US10813890B2 (en) | 2010-06-15 | 2020-10-27 | Grünenthal GmbH | Pharmaceutical combination |
AU2011267474B2 (en) * | 2010-06-15 | 2016-05-26 | Grünenthal GmbH | Pharmaceutical combination for the treatment of pain |
US8846765B2 (en) | 2010-06-15 | 2014-09-30 | Gruenenthal Gmbh | Pharmaceutical combination |
WO2011157391A1 (fr) * | 2010-06-15 | 2011-12-22 | Grünenthal GmbH | Combinaison pharmaceutique pour le traitement de la douleur |
JP2013528629A (ja) * | 2010-06-15 | 2013-07-11 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 痛み治療用の医薬配合物 |
CN103108631B (zh) * | 2010-06-15 | 2015-08-26 | 格吕伦塔尔有限公司 | 用于治疗疼痛的联合药物 |
RU2675261C2 (ru) * | 2010-06-15 | 2018-12-18 | Грюненталь Гмбх | Фармацевтическая комбинация для лечения от боли |
AU2016219643B2 (en) * | 2010-06-15 | 2018-04-12 | Grünenthal GmbH | Pharmaceutical combination for the treatment of pain |
WO2013017233A1 (fr) * | 2011-07-29 | 2013-02-07 | Grünenthal GmbH | Administration intrathécale ou épidurale de 3-[(1s,2s)-3-(diméthylamino)-1-éthyl-2-méthyl-propyl]-phénol |
EP3300726A1 (fr) * | 2011-07-29 | 2018-04-04 | Grünenthal GmbH | Administration intrathécale ou épidurale de 3-[(1s, 2s)-3- (diméthylamino)-1-éthyl-2-méthylpropyl] phénol |
JP2014524924A (ja) * | 2011-07-29 | 2014-09-25 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 3−[(1s,2s)−3−(ジメチルアミノ)−1−エチル−2−メチルプロピル]フェノールのくも膜下投与または硬膜外投与 |
US8895623B2 (en) | 2011-07-29 | 2014-11-25 | Gruenenthal Gmbh | Intrathecal or epidural administration of 3-[(1S,25)-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol |
US12005042B2 (en) | 2017-02-10 | 2024-06-11 | Acacia Pharma Ltd. | Rescue treatment of post operative nausea and vomiting |
Also Published As
Publication number | Publication date |
---|---|
AU2002361185A1 (en) | 2003-07-09 |
DE10163421A1 (de) | 2003-07-31 |
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