WO2000045846A1 - Pharmaceutical compositions containing nicotine or a ligand of nicotine receptors and a monamine oxydase inhibitor and their use for treating tobacco withdrawal symptoms - Google Patents
Pharmaceutical compositions containing nicotine or a ligand of nicotine receptors and a monamine oxydase inhibitor and their use for treating tobacco withdrawal symptoms Download PDFInfo
- Publication number
- WO2000045846A1 WO2000045846A1 PCT/FR2000/000193 FR0000193W WO0045846A1 WO 2000045846 A1 WO2000045846 A1 WO 2000045846A1 FR 0000193 W FR0000193 W FR 0000193W WO 0045846 A1 WO0045846 A1 WO 0045846A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- azabicyclo
- nicotine
- monoamine oxidase
- pharmaceutical composition
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61K31/465—Nicotine; Derivatives thereof
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
Definitions
- the subject of the present invention is a new pharmaceutical composition comprising nicotine or a nicotinic receptor ligand intended for smoking cessation.
- Tobacco consumption is considered a real public health problem, since tobacco is the cause of several serious diseases such as cardiovascular, respiratory and certain types of cancer.
- taking this type of medication is not without side effects, in particular an increase in blood pressure, heart rate and gastrointestinal effects.
- the compounds available on the market such as (Nikoban 5 , Bantron ® , CigArrest ⁇ and Nic-Fit ⁇ ) for example are often administered with antacids to avoid undesirable gastrointestinal effects.
- Nicotine like other substances of various origins (alcohol, cocaine 7), causes addiction. These molecules act via separate primary mechanisms leading to the activation of a common mechanism responsible for the pleasure induced by their consumption.
- dopamine plays a major role linked to its involvement in hedonic behavior.
- MAOIs Monoamine oxidase inhibitors
- MAOIs of type B are potentially useful in this type of treatment (see Fowler et al., Neuropharmacological actions of cigarette smoke: brain monoamine oxidase B (MAOB) inhibition J. Add. Di sease (1998 ), 17, 23-34 and Fowler et al. Nature (1996), 379, 733-736)
- MAOB brain monoamine oxidase B
- patent application 095/28934 the use of monoamine oxidase A inhibitors for the control of Smoking consumption, and especially during cravings, is described. By increasing the amount of dopamine at the pleasure centers located in the limbic system, these compounds could reproduce the hedonic sensation associated with smoking and promote smoking cessation.
- US Patent 5,803,081 mentions the possibility of producing a chewing gum containing cut tobacco treated with propolis, as a reservoir for a prolonged release of nicotine, and possibly of a monoamine oxidase B inhibitor as found in tobacco smoke.
- the advantages cited for this chewing gum lie in the pretreatment of tobacco with propolis, making it possible to avoid peaks of nicotine release while prolonging the flavor of the chewing gum.
- a monoamine oxidase B inhibitor not described there as essential for achieving the above-mentioned advantages, but also no monoamine oxidase B inhibitor is specifically mentioned in its structure or even in its possible role in this chewing gum.
- the chewing gum itself is not illustrated by an example of a technical embodiment.
- the aim of the present invention is to provide a pharmaceutical composition comprising nicotine or a ligand for nicotmic receptors, useful in smoking cessation and whose cardiovascular side effects are reduced.
- the Applicant has indeed been able to demonstrate, surprisingly, that the side effects subsequent to the administration of nicotine or a ligand for nicotinic receptors can be considerably reduced by virtue of the co-administration of a monoamine oxidase inhibitor.
- the subject of the invention is therefore a pharmaceutical composition
- a pharmaceutical composition comprising nicotine or a ligand for nicotinic receptors and a monoamine oxidase inhibitor, useful for smoking cessation and whose cardiovascular side effects are reduced.
- nicotinic receptor ligand is understood to mean, in the context of the present invention, in particular agonists of nicotinic receptors such as cytisine, lobelin, ABT-418 (Abbott), epibatidine, GTS-21, AR -R17779 (AstraZeneca), ABT-594 (Abbott), ABT-089 (Abbott), but also other nicotinic receptor ligands such as: AN-072 (Elan), eperisone (Eisai), rapacuronium bromide (Akzo Nobel), altinicline (Sibia), conantokin-G (Cognetix), GW-280430 (Glaxo Wellcome), RJR-2403 (Targacept), galantamine, SIB 1553 A (Sibia) , A-85380 (Abbott), metanicotine, RJR-2531 (RJ Reynolds Tobacco), RJR-2557 (RJ Reynolds Tob
- one of the symbols X, Y and Z represents a nitrogen atom
- another represents a group of formula CR 3 and the third represents a nitrogen atom or a group of formula CR 4 , R 3 and R.
- each represent, independently of one another, a hydrogen or halogen atom or a trifluoromethyl, cyano, hydroxy, (C, -C 6 ) alkyl or (Ci-Cg) group alkoxy
- R x and R 2 each represent, independently of one another, a hydrogen or halogen atom or a trifluoromethyl, cyano, hydroxy group, alkyl, (Ci-Cg) - alkoxy, or phenyl optionally substituted by one or two halogen atoms, by one or two trifluoromethyl groups, by a cyano group, by a nitro group, by a hydroxy group, by a group (C x -C 6 ) alkyl, by one or two groups alkoxy, by
- R 3 and R 4 each represent , independently of one another, a hydrogen or halogen atom or a trifluoromethyl, cyano, hydroxy, (Ci-Cg) alkyl or (Ci-Cg) alkoxy group
- R and R 2 each represent, independently of one another, a hydrogen or halogen atom or a trifluoromethyl, cyano, hydroxy, (Cj-Cg) alkyl group, alkoxy, or phenyl optionally substituted by a halogen atom, by one or two trifluoromethyl groups, by a cyano group, by a nitro group, by a hydroxy group, by a group alkoxy, by an acetyl group, by a methylenedioxy group, by a trifluoromethoxy group, by
- agonists are preferred.
- composition according to the present invention the increase in blood pressure and heart rate is minimized.
- the composition provides greater safety and better tolerance and therefore better compliance of the treatment for the patient.
- a reversible monoamine oxidase A inhibitor or A reversible mixed A or B, reversible or irreversible B with nicotine or a nicotinic receptor ligand can have an amplifying effect on the beneficial effects of nicotine by example the feeling of pleasure, the improvement of the mood, the improvement of the psychomotor and cognitive performances while reducing the side effects, in particular cardiovascular.
- compositions comprising nicotine or a nicotinic receptor ligand and a reversible monoamine oxidase inhibitor.
- the monoamine oxidase inhibitor can be a reversible monoamine oxidase A inhibitor, a reversible or irreversible monoamine oxidase B inhibitor or an inhibitor of the reversible mixed monoamine oxidase A, B.
- Befloxatone and moclobemide are most particularly preferred as a reversible monoamine oxidase A inhibitor, as is (-) 3 - [2- (3, 3, 3 -trifluoropropyl) -
- the MAOIs will be preferred for the compositions according to the present invention.
- Another object of the present invention consists of a pharmaceutical composition comprising nicotine or nicotinic receptor ligand and a monoamine oxidase inhibitor as a combination product for simultaneous, separate or spread over time intended for smoking cessation.
- spontaneous use is understood to mean the administration of the compounds of the composition according to the invention included in one and the same pharmaceutical form.
- separate use is meant the administration, at the same time, of the two compounds of the composition according to the invention each included in a separate pharmaceutical form.
- use spread over time is understood to mean the successive administration of the first compound of the composition according to the invention, included in a pharmaceutical form, then of the second compound of the composition according to the invention, included in a pharmaceutical form separate.
- the period of time between the administration of the first compound of the composition according to the invention and the administration of the second compound of the same composition according to the invention does not exceed usually not 24 hours.
- the pharmaceutical forms comprising either only one of the constituent compounds of the composition according to the invention or the combination of the two compounds, which can be used in the different types of uses described above, can for example be suitable for oral, nasal, parenteral or transdermal administration.
- the two separate pharmaceutical forms can be intended for the same route of administration or for a different route of administration (oral and transdermal or oral and nasal or parenteral and transdermal etc).
- compositions suitable for oral administration mention may be made of tablets, capsules, pills and chewing gums with immediate or prolonged release.
- dosage forms such as suspensions or injectable solutions are suitable.
- composition according to the invention can then be administered in a single daily dose or in divided daily doses. In the latter case, the composition can be administered in 2 to 3 doses per day.
- transdermal patches or patches are for example suitable for transdermal administration.
- gels or emulsions are also suitable.
- transdermal patch or patch which allows slow and regular administration for at least one of the two compounds of the combination.
- the patient's autonomy vis-à-vis his treatment is thus favored.
- the patch makes it possible to obtain a release of the composition which can last between 8 and 72 hours.
- compositions suitable for use in a patch or patch can be in the form of a gel, ointment, solution, cream or emulsion. They can be prepared according to conventional methods for those skilled in the art.
- compositions can also be formulated as a nasal spray, pulmonary spray or suppository.
- At least one of the two components of the combination is administered transdermally, for example by patch or transdermal patch.
- compositions according to the The present invention is dosed to allow daily administration of 2 to 20 mg of nicotine or of nicotinic receptor ligand and from 1 to 20 mg of monoamine oxidase inhibitor.
- the present invention also relates to the use of nicotine or a ligand for nicotinic receptors and a monoamine oxidase inhibitor for the manufacture of a medicament intended for smoking cessation.
- Befloxatone or moclobemide is suspended in a vehicle (Tween 80 0.5% w / v, methylcellulose 0.5% w / v in water for injection). Nicotine is dissolved in water for an injectable preparation.
- the animals underwent, under general anesthesia by mtrapé ⁇ tonéale injection of ketamme (116 mg / kg ⁇ .p.), a cathtate ⁇ sme of the carotid and the jugular vein with exteriorization of the catheters in dorsoscapular region.
- ketamme 116 mg / kg ⁇ .p.
- a cathlus ⁇ sme of the carotid and the jugular vein with exteriorization of the catheters in dorsoscapular region.
- the day after implantation the animals were connected to measuring devices allowing the continuous recording of blood pressure and heart rate. After a stabilization period of approximately 30 minutes, the animals received the oral treatment, then 45 minutes later, three increasing doses of nicotine, administered intravenously at an interval of 5 minutes.
- Average blood pressure and heart rate were measured before treatment, before each administration of nicotine, and at the peak of the effect of these administrations.
- nicotine causes an increase in average blood pressure in the control animals and a slight increase in heart rate.
- Befloxatone 1 mg / kg po and moclobemide 10 mg / kg po reduce the increases in blood pressure and heart rate induced, between 45 min and 60 min after treatment, by intravenous administration of nicotine. (TAB.l to 4).
- TAB.l Average blood pressure (mm Hg), awake rat
- TAB .3 Average blood pressure (mm Hg), awake rat
- NS not significantly different from the vehicle group (P> 0.05, Dunnett test after two-factor analysis of variance with repeated measurements)
- Tablets containing 10 mg of befloxatone are manufactured according to the following composition
- the first five components are mel aged, granulated with water, dried and graded.
- the granules are then mixed with the magnesium stearate and compressed to form tablets of 200 mg by mass, using a rotary press.
- a transdermal patch with an area of 20 cm 2 capable of delivering 14 mg in 24 hours is prepared according to the following composition:
- the granules are prepared by wet granulation according to the following compositions:
- microcrystalline cellulose 15 microcrystalline cellulose 20% povidone 4% hydroxypropyl methylcellulose 25% magnesium stearate 1%
- bilayer tablets are prepared by compression using a press
- Manesty BL Each layer contains 100 mg of granules so that each tablet contains 5 mg of befloxatone and 5 mg of nicotine.
- the tablets containing 10 mg of befloxatone are prepared according to the following composition:
- magnesium stearate 0.50 colloidal silica 0.10 The first five components of each pellet are mixed, pelletized with water, dried and graded. The granules are then mixed with magnesium stearate and colloidal silica and then gelatin capsules of size 2 of 160 mg of the granules thus prepared are filled.
- a solution for nasal administration containing 50 mg of nicotine, 900 mg of sodium chloride, 10 mg of benzalkonium chloride, 100 mg of EDTA sodium and 100 mg of sterilized water is prepared. This solution is filtered and distributed in ampoules.
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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)
- Organic Chemistry (AREA)
- Addiction (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000596965A JP2002536342A (en) | 1999-02-02 | 2000-01-28 | Pharmaceutical compositions comprising nicotine or a nicotine receptor ligand and a monoamine oxidase inhibitor, and their use for treating tobacco withdrawal symptoms |
AU22988/00A AU2298800A (en) | 1999-02-02 | 2000-01-28 | Pharmaceutical compositions containing nicotine or a ligand of nicotine receptors and a monamine oxydase inhibitor and their use for treating tobacco withdrawalsymptoms |
CA002361437A CA2361437A1 (en) | 1999-02-02 | 2000-01-28 | Pharmaceutical compositions containing nicotine or a ligand of nicotine receptors and a monamine oxydase inhibitor and their use for treating tobacco withdrawal symptoms |
EP00901660A EP1150715A1 (en) | 1999-02-02 | 2000-01-28 | Pharmaceutical compositions containing nicotine or a ligand of nicotine receptors and a monamine oxydase inhibitor and their use for treating tobacco withdrawal symptoms |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR99/01144 | 1999-02-02 | ||
FR9901144A FR2788982B1 (en) | 1999-02-02 | 1999-02-02 | PHARMACEUTICAL COMPOSITIONS CONTAINING NICOTINE AND THEIR APPLICATION IN SMOKING WITHDRAWAL |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000045846A1 true WO2000045846A1 (en) | 2000-08-10 |
Family
ID=9541474
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2000/000193 WO2000045846A1 (en) | 1999-02-02 | 2000-01-28 | Pharmaceutical compositions containing nicotine or a ligand of nicotine receptors and a monamine oxydase inhibitor and their use for treating tobacco withdrawal symptoms |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP1150715A1 (en) |
JP (1) | JP2002536342A (en) |
AR (1) | AR028983A1 (en) |
AU (1) | AU2298800A (en) |
CA (1) | CA2361437A1 (en) |
FR (1) | FR2788982B1 (en) |
HU (1) | HUP0201279A2 (en) |
WO (1) | WO2000045846A1 (en) |
Cited By (27)
Publication number | Priority date | Publication date | Assignee | Title |
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KR20010050225A (en) * | 1999-08-27 | 2001-06-15 | 실버스타인 아써 에이. | A pharmaceutical composition for the prevention and treatment of nicotine addiction in a mammal |
WO2001062736A1 (en) * | 2000-02-25 | 2001-08-30 | Pfizer Products Inc. | Aryl fused azapolycyclic compounds |
WO2002030405A2 (en) * | 2000-10-13 | 2002-04-18 | Neurosearch A/S | Treatment of affective disorders by the combined action of a nicotinic receptor agonist and a monoaminergic substance |
US6410550B1 (en) * | 1997-12-31 | 2002-06-25 | Pfizer Inc | Aryl fused azapolycyclic compounds |
WO2003087104A1 (en) * | 2002-04-18 | 2003-10-23 | Astrazeneca Ab | Heterocyclic compounds |
WO2003087102A1 (en) * | 2002-04-18 | 2003-10-23 | Astrazeneca Ab | Furyl compounds |
EP1382605A2 (en) * | 1998-11-27 | 2004-01-21 | Neurosearch A/S | 8-azabicyclo(3.2.1)oct-2-ene derivatives and their use as nAChR ligands |
US7091372B2 (en) * | 2001-04-20 | 2006-08-15 | Pfizer Inc | Process for the preparation of 1,3-substituted indenes and aryl-fused azapolycyclic compounds |
US7186836B2 (en) | 2002-04-18 | 2007-03-06 | Astrazeneca Ab | Thienyl compounds |
WO2007100430A2 (en) * | 2006-01-27 | 2007-09-07 | Yale University | Cytisine and acetylcholine analogs and methods of treating mood disorders |
US7396833B2 (en) | 2003-12-22 | 2008-07-08 | Memory Pharmaceuticals Corporation | Indoles, 1H-indazoles, 1,2-benzisoxazoles, and 1,2-benzisothiazoles, and preparation and uses thereof |
WO2008091592A1 (en) * | 2007-01-22 | 2008-07-31 | Targacept, Inc. | Intranasal, buccal, and sublingual administration of metanicotine analogs |
US7429664B2 (en) | 2002-09-25 | 2008-09-30 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, and benzoisothiazoles, and preparation and uses thereof |
US7459469B2 (en) | 2004-11-10 | 2008-12-02 | Targacept, Inc. | Hydroxybenzoate salts of metanicotine compounds |
US7488737B2 (en) | 2004-04-22 | 2009-02-10 | Memory Pharmaceutical Corporation | Indoles, 1H-indazoles, 1,2-benzisoxazoles, 1,2-benzoisothiazoles, and preparation and uses thereof |
WO2009058120A1 (en) * | 2007-11-02 | 2009-05-07 | Sri International | Nicotinic acetylcholine receptor modulators |
US20090118326A1 (en) * | 2007-11-02 | 2009-05-07 | Faming Jiang | Nicotinic Acetylcholine Receptor Modulators |
US7625924B2 (en) | 2004-12-22 | 2009-12-01 | Memory Pharmaceuticals Corporation | Nicotinic alpha-7 receptor ligands and preparation and uses thereof |
US7632831B2 (en) | 2004-05-07 | 2009-12-15 | Memory Pharmaceuticals Corporation | 1H-indazoles, benzothiazoles, 1,2-benzoisoxazoles, 1,2-benzoisothiazoles, and chromones and preparation and uses thereof |
US8017785B2 (en) | 2006-05-09 | 2011-09-13 | Astrazeneca Ab | Salt forms of (2S)-(4E)-N-methyl-5-[3-(5-isopropoxypyridin)y1]-4-penten 2-amine |
US8093300B2 (en) | 2001-11-05 | 2012-01-10 | Krele Pharmaceuticals, Inc. | Compositions and methods for increasing compliance with therapies using aldehyde dehydrogenase inhibitors and treating alcoholism |
US8106066B2 (en) | 2005-09-23 | 2012-01-31 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof |
US8263619B2 (en) | 2004-03-25 | 2012-09-11 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, and preparation and uses thereof |
US8461344B2 (en) | 2006-05-09 | 2013-06-11 | Targacept, Inc. | Polymorph forms of (2S)-(4E)-N-methyl-5-[3-(5-isopropdxypyridin)yl]-4-penten-2-amine |
US8703802B2 (en) | 2010-05-20 | 2014-04-22 | Targacept, Inc. | Process for the preparation of aryl substituted olefinic amines |
US9062042B2 (en) | 2010-01-11 | 2015-06-23 | Astraea Therapeutics, Llc | Nicotinic acetylcholine receptor modulators |
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-
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- 2000-01-28 WO PCT/FR2000/000193 patent/WO2000045846A1/en not_active Application Discontinuation
- 2000-01-28 EP EP00901660A patent/EP1150715A1/en not_active Withdrawn
- 2000-01-28 JP JP2000596965A patent/JP2002536342A/en not_active Withdrawn
- 2000-01-28 AU AU22988/00A patent/AU2298800A/en not_active Abandoned
- 2000-01-28 CA CA002361437A patent/CA2361437A1/en not_active Abandoned
- 2000-01-31 AR ARP000100404A patent/AR028983A1/en not_active Application Discontinuation
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KR20010050225A (en) * | 1999-08-27 | 2001-06-15 | 실버스타인 아써 에이. | A pharmaceutical composition for the prevention and treatment of nicotine addiction in a mammal |
WO2001062736A1 (en) * | 2000-02-25 | 2001-08-30 | Pfizer Products Inc. | Aryl fused azapolycyclic compounds |
CZ303203B6 (en) * | 2000-02-25 | 2012-05-23 | Pfizer Products Inc. | Azapolycyclic compound with annellated aryl group and medicament containing thereof |
US7307087B2 (en) | 2000-10-13 | 2007-12-11 | Neurosearch A/S | Treatment of affective disorders by the combined action of a nicotinic receptor agonist and a monoaminergic substance |
WO2002030405A3 (en) * | 2000-10-13 | 2002-09-06 | Neurosearch As | Treatment of affective disorders by the combined action of a nicotinic receptor agonist and a monoaminergic substance |
WO2002030405A2 (en) * | 2000-10-13 | 2002-04-18 | Neurosearch A/S | Treatment of affective disorders by the combined action of a nicotinic receptor agonist and a monoaminergic substance |
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US7091372B2 (en) * | 2001-04-20 | 2006-08-15 | Pfizer Inc | Process for the preparation of 1,3-substituted indenes and aryl-fused azapolycyclic compounds |
US7186870B2 (en) * | 2001-04-20 | 2007-03-06 | Pfizer Inc | Process for the preparation of 1,3-substituted indenes and aryl-fused azapolycyclic compounds |
US8481599B2 (en) | 2001-11-05 | 2013-07-09 | Tonix Pharmaceuticals Inc. | Compositions and methods for increasing compliance with therapies using aldehyde dehydrogenase inhibitors and treating alcoholism |
US8093300B2 (en) | 2001-11-05 | 2012-01-10 | Krele Pharmaceuticals, Inc. | Compositions and methods for increasing compliance with therapies using aldehyde dehydrogenase inhibitors and treating alcoholism |
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AU2298800A (en) | 2000-08-25 |
FR2788982B1 (en) | 2002-08-02 |
EP1150715A1 (en) | 2001-11-07 |
JP2002536342A (en) | 2002-10-29 |
CA2361437A1 (en) | 2000-08-10 |
FR2788982A1 (en) | 2000-08-04 |
HUP0201279A2 (en) | 2002-09-28 |
AR028983A1 (en) | 2003-06-04 |
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