EP0828484A1 - Utilisation de cyclobutylalkylamines substituees par aryle pour le traitement de l'obesite - Google Patents
Utilisation de cyclobutylalkylamines substituees par aryle pour le traitement de l'obesiteInfo
- Publication number
- EP0828484A1 EP0828484A1 EP96916161A EP96916161A EP0828484A1 EP 0828484 A1 EP0828484 A1 EP 0828484A1 EP 96916161 A EP96916161 A EP 96916161A EP 96916161 A EP96916161 A EP 96916161A EP 0828484 A1 EP0828484 A1 EP 0828484A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- carbon atoms
- hydrogen atom
- general formula
- compounds
- 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- Withdrawn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
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
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
Definitions
- the invention relates to the use of aryl-substituted cyclobutylalkylamines for the treatment of obesity.
- Aryl-substituted cyclobutylalkylamines are known from DE 32 12 682 C2. The compounds disclosed there are used as antidepressants.
- Index n has the value 0 or 1
- R 1 in the case where the index n has the value 0, a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a cycloalkylalkyl group in which the cycloalkyl group has 3 to 6 carbon atoms and the alkyl group Contains 1 to 3 carbon atoms, means an alkenyl or an alkynyl group with 2 to 6 carbon atoms, it being possible for the alkyl group, the cycloalkyl group, the cycloalkylalkyl group, the alkenyl or alkynyl group to contain at least one substituent selected from the group consisting of hydroxyl and acylated derivatives thereof, alkoxy groups, optionally substituted by hydroxyl, oxo, alkoxy, carbamoyl, carbocyclic or heterocyclic groups, cycloalkyloxy groups with 3 to 6 carbon atoms, Al-
- R 9 and R 10 which may be the same or different, represent a hydrogen atom, a halogen atom or an alkoxy group having 1 to 3 carbon atoms,
- n 1
- n 1
- R 2 represents a hydrogen atom or an alkyl group with 1 to 3 carbon atoms
- R 3 represents a hydrogen atom
- R 4 represents a hydrogen atom, a straight-chain or branched-chain alkyl group with 1 to 4 carbon atoms, an alkenyl group with 3 to 6 carbon atoms, an alkynyl group with 3 to 6 carbon atoms, or a cycloalkyl group in which the ring contains 3 to 7 carbon atoms,
- R 4 means CHO
- R 5 and R 6 which may be the same or different, represent a hydrogen atom, a halogen atom, a trifluoromethyl group, an alkyl group with 1 to 3 carbon atoms, an alkoxy or alkylthio group with 1 to 3 carbon atoms or a phenyl group, or together with the carbon atoms to which they are attached form a second benzene ring, which may be substituted by one or more halogen atoms, an alkyl or alkoxy group having 1 to 4 carbon atoms, or the substituents of the second Benzene rings together with the two carbon atoms to which they are attached form another benzene ring, and
- R 7 and R 8 which may be the same or different, are a hydrogen atom or an alkyl group having 1 to 3 carbon atoms,
- X represents a hydrogen atom or a hydroxy group
- the compounds used according to the invention have the advantage of very good bioavailability and show a more favorable spectrum of side effects.
- R 1 is a straight-chain or branched-chain alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a cycloalkylmethyl group in which the cycloalkyl ring contains 3 to 6 carbon atoms, or a group of the general formula II in which R 9 and / or R 10 represent a hydrogen atom, a fluorine atom or ethoxy, and R 2 represents a hydrogen atom or methyl.
- Examples of particularly preferred compounds of the general formula I are those in which R 1 is methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl , Cyclohexylmethyl and phenyl if the index n is 0 and R 2 is a hydrogen atom.
- R 1 is a hydrogen atom or methyl
- R 2 is a hydrogen atom.
- both R 1 and R 2 are each a hydrogen atom.
- R 4 is a hydrogen atom, methyl, ethyl or formyl.
- R 5 and / or R 6 are a hydrogen, fluorine, chlorine, bromine or iodine atom, trifluoromethyl, methyl, methoxy or phenyl, or R 5 and R 6 together with the carbon atoms form , to which they are bound, a second benzene ring, which may optionally be substituted by halogen.
- a first group of preferred compounds is represented by the general formula III
- R 5 and R 6 which may be the same or different, are a hydrogen, fluorine, chlorine, bromine or iodine atom, trifluoromethyl, methyl, methoxy or phenyl, or they form R 5 and R 6 together with the carbon atoms to which they are attached form a second one Benzene ring, which may optionally be substituted by a chlorine atom.
- R 5 and / or R 6 are a hydrogen, fluorine, chlorine or iodine atom, trifluoromethyl, methyl or phenyl, or R 5 and R 6 form together with the carbon atoms to which they are attached are bound, a second benzene ring, which may optionally be substituted by a chlorine atom.
- R 5 can be a hydrogen, fluorine, chlorine, bromine or iodine atom, trifluoromethyl, methyl, methoxy or phenyl, and in which R 6 is a fluorine atom or methyl.
- R 5 is a hydrogen or chlorine atom.
- R 7 is a hydrogen atom, methyl or ethyl
- R 8 is a hydrogen atom
- R 7 is a Hydrogen atom or ethyl
- R 8 is a hydrogen atom
- R 1 is a C -alkyl radical, in particular isobutyl
- R 2 is a hydrogen
- n 0,
- R 4 is a Ci- or C 2 -alkyl radical
- R 5 is a chlorine atom and R 6 is a water material.
- X is a hydrogen atom
- Compounds of the general formula I can exist as salts with pharmaceutically acceptable acids. Salts of inorganic and organic acids are suitable.
- salts examples include sulfates, hydrochlorides, hydrobromides, nitrates, phosphates, maleates, acetates, citrates, lactates, benzoates, aryl sulfonates, alkyl sulfonates, in particular methane, ethane, propane and butanesulfonates, fumarates, gluconates, tartrates, succinates, tosylates and salts with acidic amino acids, such as aspartic acid and glutamic acid. Hydrochlorides, acetates, phosphates and tosylates are preferred.
- the compounds of the general formula I contain two chiral centers and the compounds exist in four diastereoisomeric forms.
- the present invention includes each of these diastereoisomeric forms and mixtures thereof.
- the compounds of general formula I are used in pharmaceutical preparations which contain a therapeutically effective amount of a compound of general formula I, together with a pharmaceutically acceptable diluent or carrier.
- the active compound can be administered orally, rectally, parenterally or topically, preferably orally.
- the therapeutic preparations of the present invention can take the form of any
- compositions of the invention can range from 0.1 to
- the preparations according to the invention are usually produced in unit dose form.
- Preparations for oral administration are the preferred preparations of the invention and these are the known pharmaceutical forms for such administration, for example tablets, capsules, syrups and aqueous or oily suspensions with an acute or delayed release profile.
- the carriers used to produce these preparations are those which are known to the person skilled in the pharmaceutical field.
- Tablets can be prepared by mixing the active compound with an inert diluent such as calcium phosphate in the presence of luminescent or dissolving agents, for example corn starch and lubricants, for example magnesium stearate, and tableting the mixture by known methods.
- the tablets can be formulated in a manner known to the person skilled in the art in order to ensure a uniform release of the compounds of the present invention.
- tablets of this type can be provided with coatings which are only soluble in the intestine using known methods, for example by using cellulose acetate phthalate.
- capsules for example hard or soft gelatin capsules, which contain the active compound with or without added carriers, can be produced by conventional methods. which, and, if desired, are provided in a known manner with coatings which are only soluble in the intestine.
- the tablets and capsules can suitably contain each 1 to 500 mg of active compound.
- the tablets can also be produced by extrusion processes, if appropriate with subsequent shaping. Such extrusion processes are known from the prior art (for example EP 240 904, EP 240 906 and EP 358 105).
- compositions for oral administration include, for example, aqueous suspensions which contain the active compound in an aqueous medium in the presence of a non-toxic suspending agent, such as sodium carboxymethyl cellulose, and oily suspensions which contain a compound of the present invention in a suitable vegetable oil, for example in Contain peanut oil.
- a non-toxic suspending agent such as sodium carboxymethyl cellulose
- oily suspensions which contain a compound of the present invention in a suitable vegetable oil, for example in Contain peanut oil.
- Preparations of the present invention which are suitable for rectal administration are the known pharmaceutical forms for such administration, for example suppositories with cocoa butter or polyethylene glycol bases.
- Preparations with compounds of general formula I which are suitable for parenteral administration are the known pharmaceutical forms for such administration, for example sterile suspensions in aqueous or oily media, or sterile solutions in a suitable solvent.
- Preparations for topical administration may contain a base in which the pharmacologically active compounds of the present invention are dispersed so that the compounds are kept in contact with the skin to administer the compounds transdermally.
- the active compounds can be dispersed in a pharmaceutically acceptable cream or ointment base.
- the active compound can, if desired, be combined with other compatible pharmacologically active ingredients.
- the pharmaceutical preparations which contain a therapeutically effective amount of a compound of general formula I can be used for the treatment of obesity in humans.
- the amount of the compound of general formula I administered per day is dependent on various factors such as e.g. depending on the age, and is usually in the range from 0.1 to 500 mg, preferably in the range from 1 to 100 mg, administered in one or more doses.
- the compounds of formula I can be prepared in various ways.
- Compounds of the general formula I in which R 4 is a hydrogen atom can also be prepared by decarboxylative rearrangement of acylazides in the Curtius reaction.
- the acyl azides can be formed, for example, by reacting corresponding acid chlorides with sodium azide.
- Compounds of the general formula I in which R 4 is a hydrogen atom can also be prepared by a Schmidt reaction in which a corresponding carboxylic acid reacts with hydrochloric acid.
- Compounds of the general formula I in which R 4 is a hydrogen atom can also be prepared by hydrolysis of compounds of the general formula I in which R 4 is CHO, for example by acid hydrolysis.
- Compounds of the general formula I in which R 4 is methyl can be prepared by reducing compounds of the general formula I in which R 4 is CHO, for example with lithium aluminum hydride or with sodium bis (2-methoxyethoxy) aluminum hydride.
- Compounds of the general formula I, in which R 4 is not a hydrogen atom can be prepared from compounds of the general formula I, in which R 4 is hydrogen, by methods which are known to the person skilled in the art for converting primary to secondary Amines are known. Examples of suitable processes are given in detail in DE 32 12 682, to which reference is hereby made.
- Hydroxy group can be obtained by a tandem Grignard reaction of a 3-hydroxycyclobutane-1-phenyl-1-carbonitrile with isobutyl magnesium bromide, and optionally those compounds can also be used which carry a protective group on the oxygen atom.
- the individual enantiomers can be prepared from optically active precursors by enantiomer-selective synthesis, or by resolving the racemate, which can be prepared as described above.
- Enantiomers of secondary amines of the formula I can also be prepared by preparing the racemate of the corresponding primary, separating it into the individual enantiomers and then converting the optically pure primary amine enantiomer into the desired secondary amine.
- Example 1 of DE 32 12 682 describes the production of
- Tablets are made from the following ingredients:
- the active ingredient, the lactose and part of the starch are mixed and granulated with a solution of the polyvinylpyrrolidone in ethanol.
- the granules are mixed with the stearic acid and the rest of the starch and the mixture is compressed in a tablet machine to tablets which contain 50.0 mg of the active ingredient.
- Capsules are produced in the following way: A mixture of the active ingredient (45 parts by weight) and lactose powder (205 parts by weight) is filled into capsules made of hard gelatin, each capsule containing 45 mg of the active ingredient.
- the tablets are coated with a thin layer of shellac lacquer, followed by 20 coatings of cellulose acetate phthalate, in a manner known to those skilled in the art.
- the capsules can be provided with a coating that is only soluble in the intestine.
- Ampoules which contain a solution of water-soluble compounds of the present invention which are suitable for injection are produced from the following constituents:
- suppositories 100 parts by weight of the finely ground active ingredient are incorporated in 1214 parts by weight of triglyceride suppository base and the mixture is shaped into suppositories, each of which contains 100 mg of the active ingredient.
- the compounds of formula I are suitable for the treatment of obesity and its concomitant diseases.
- the accompanying diseases of obesity include: diabetes, hypertension and hypercholesterolemia.
- R i for isobutyl, R 2 for H, R 3 for methyl, R 4 for H, R ⁇ for 4-chlorine, R 6 for H and X for H, and
- R i is isobutyl
- R 2 is H
- R 3 is H
- R 4 is H
- R 5 is 4-chlorine
- R6 is H
- X is H
- Concentric dialysis probes were constructed with tubes made of stainless steel and silica hollow fibers. The total length of the probe was adjusted so that the tip was in the hypothalamus (target point for the probe tip: DV 9.7 under the skull).
- the exchange surface of the probes was a 2.5 mm long nitrocellulose hollow fiber (0.2 mm outside diameter, molecular weight cutoff 6000; Spectrum Medical Industries, Los Angeles, CA).
- the probe was cemented into the guide cannula and also protected by a cylindrical plastic sleeve.
- the animals were placed in a test chamber and attached to a liquid tipping device so that they could move freely.
- the probes were continuously treated with artificial CSF (aCSF; 147 mM NaCl, 4.0 ⁇ iM KC1, 1.8 mM CaCl 2 , pH 6.3 not set) at a rate of 1.0 ⁇ l / min. perfused using a microinjection pump (CMA / 100), Carnegie-Medicin, Sweden). From the next morning, samples were collected during the dark phase.
- CSF artificial CSF
- the samples were analyzed by HPLC.
- the detection was carried out electrochemically.
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Child & Adolescent Psychology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Utilisation de cyclobutylalkylamines substituées par aryle et de leurs sels pharmaco-compatibles pour le traitement de l'obésité et de ses maladies associées.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19518988A DE19518988A1 (de) | 1995-05-29 | 1995-05-29 | Verwendung arylsubstituierter Cyclobutylalkylamine zur Behandlung der Fettleibigkeit |
DE19518988 | 1995-05-29 | ||
PCT/EP1996/002239 WO1996038134A1 (fr) | 1995-05-29 | 1996-05-24 | Utilisation de cyclobutylalkylamines substituees par aryle pour le traitement de l'obesite |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0828484A1 true EP0828484A1 (fr) | 1998-03-18 |
Family
ID=7762715
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP96916161A Withdrawn EP0828484A1 (fr) | 1995-05-29 | 1996-05-24 | Utilisation de cyclobutylalkylamines substituees par aryle pour le traitement de l'obesite |
Country Status (8)
Country | Link |
---|---|
US (1) | US6127424A (fr) |
EP (1) | EP0828484A1 (fr) |
JP (1) | JPH11506439A (fr) |
AU (1) | AU702776B2 (fr) |
CA (1) | CA2218918A1 (fr) |
DE (1) | DE19518988A1 (fr) |
WO (1) | WO1996038134A1 (fr) |
ZA (1) | ZA964298B (fr) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6046242A (en) * | 1998-11-27 | 2000-04-04 | Basf Aktiengesellschaft | Use of aryl-substituted cyclobutylalkylamines for treating urinary incontinence |
AU4172900A (en) * | 1999-03-19 | 2000-10-09 | Abbott Gmbh & Co. Kg | Weight loss after pregnancy |
EP1165060A4 (fr) * | 1999-03-19 | 2002-06-12 | Knoll Gmbh | Traitement des calculs biliaires |
JP2005506042A (ja) | 2000-12-12 | 2005-03-03 | ユニヴァーシティー オブ コネティカット | 細胞トランスポーターをコードするポリヌクレオチド、およびその使用方法 |
US20030082647A1 (en) * | 2000-12-12 | 2003-05-01 | Reenan Robert A. | Transporter protein |
US6982251B2 (en) * | 2000-12-20 | 2006-01-03 | Schering Corporation | Substituted 2-azetidinones useful as hypocholesterolemic agents |
US7456184B2 (en) * | 2003-05-01 | 2008-11-25 | Palatin Technologies Inc. | Melanocortin receptor-specific compounds |
US7655658B2 (en) | 2001-08-10 | 2010-02-02 | Palatin Technologies, Inc. | Thieno [2,3-D]pyrimidine-2,4-dione melanocortin-specific compounds |
US7718802B2 (en) | 2001-08-10 | 2010-05-18 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific piperazine compounds |
CA2462200A1 (fr) | 2001-08-10 | 2003-02-20 | Palatin Technologies, Inc. | Peptidomimetiques de metallopeptides biologiquement actifs |
US7732451B2 (en) | 2001-08-10 | 2010-06-08 | Palatin Technologies, Inc. | Naphthalene-containing melanocortin receptor-specific small molecule |
US7354923B2 (en) * | 2001-08-10 | 2008-04-08 | Palatin Technologies, Inc. | Piperazine melanocortin-specific compounds |
US7208486B2 (en) | 2003-03-07 | 2007-04-24 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof |
US7235543B2 (en) | 2003-03-07 | 2007-06-26 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof |
US7727991B2 (en) | 2003-05-01 | 2010-06-01 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific single acyl piperazine compounds |
US7968548B2 (en) | 2003-05-01 | 2011-06-28 | Palatin Technologies, Inc. | Melanocortin receptor-specific piperazine compounds with diamine groups |
US7727990B2 (en) | 2003-05-01 | 2010-06-01 | Palatin Technologies, Inc. | Melanocortin receptor-specific piperazine and keto-piperazine compounds |
US7709484B1 (en) | 2004-04-19 | 2010-05-04 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific piperazine compounds |
US7834017B2 (en) | 2006-08-11 | 2010-11-16 | Palatin Technologies, Inc. | Diamine-containing, tetra-substituted piperazine compounds having identical 1- and 4-substituents |
CN101555214B (zh) * | 2008-04-08 | 2012-07-11 | 北京嘉事联博医药科技有限公司 | 苯基环丁基酰胺衍生物及其光学异构体、制备方法和用途 |
CN101514163B (zh) * | 2009-04-02 | 2013-04-24 | 广州市金匮贸易有限公司 | 光学纯西布曲明及其衍生盐的制备工艺 |
WO2018115984A1 (fr) | 2016-12-19 | 2018-06-28 | Cellix Bio Private Limited | Compositions et méthodes pour le traitement d'une inflammation |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE7703427L (sv) * | 1977-03-25 | 1978-09-26 | Astra Laekemedel Ab | Nya cykloalkylaminer |
IE52768B1 (en) * | 1981-04-06 | 1988-02-17 | Boots Co Ltd | 1-arylcyclobutylalkylamine compounds useful as therapeutic agents |
GB8704777D0 (en) * | 1987-02-28 | 1987-04-01 | Boots Co Plc | Medical treatment |
IE61928B1 (en) * | 1988-11-29 | 1994-11-30 | Boots Co Plc | Treatment of obesity |
WO1994000114A1 (fr) * | 1992-06-23 | 1994-01-06 | Sepracor Inc. | Procedes et compositions utilises pour traiter la depression et d'autres affections avec de la sibutramine (-) optiquement pure |
JPH07508281A (ja) * | 1992-06-23 | 1995-09-14 | セプラコア インコーポレーテッド | 光学的に純粋な(+)シブトラミンを用いるうつ病およびその他の障害を治療する方法ならびに組成物 |
GB9309749D0 (en) * | 1993-05-12 | 1993-06-23 | Boots Co Plc | Therapeutic agents |
-
1995
- 1995-05-29 DE DE19518988A patent/DE19518988A1/de not_active Ceased
-
1996
- 1996-05-24 US US08/952,285 patent/US6127424A/en not_active Expired - Fee Related
- 1996-05-24 AU AU59018/96A patent/AU702776B2/en not_active Ceased
- 1996-05-24 JP JP8536164A patent/JPH11506439A/ja active Pending
- 1996-05-24 CA CA002218918A patent/CA2218918A1/fr not_active Abandoned
- 1996-05-24 WO PCT/EP1996/002239 patent/WO1996038134A1/fr not_active Application Discontinuation
- 1996-05-24 EP EP96916161A patent/EP0828484A1/fr not_active Withdrawn
- 1996-05-28 ZA ZA9604298A patent/ZA964298B/xx unknown
Non-Patent Citations (1)
Title |
---|
See references of WO9638134A1 * |
Also Published As
Publication number | Publication date |
---|---|
ZA964298B (en) | 1997-11-28 |
AU702776B2 (en) | 1999-03-04 |
AU5901896A (en) | 1996-12-18 |
CA2218918A1 (fr) | 1996-12-05 |
DE19518988A1 (de) | 1996-12-05 |
US6127424A (en) | 2000-10-03 |
WO1996038134A1 (fr) | 1996-12-05 |
JPH11506439A (ja) | 1999-06-08 |
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