WO1994020466A1 - Novel 2-phenoxy ethylamine derivatives, their preparation and their therapeutical use - Google Patents
Novel 2-phenoxy ethylamine derivatives, their preparation and their therapeutical use Download PDFInfo
- Publication number
- WO1994020466A1 WO1994020466A1 PCT/FR1994/000202 FR9400202W WO9420466A1 WO 1994020466 A1 WO1994020466 A1 WO 1994020466A1 FR 9400202 W FR9400202 W FR 9400202W WO 9420466 A1 WO9420466 A1 WO 9420466A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- piperidine
- ethylaminomethyl
- phenoxy
- general formula
- phenoxyethylaminomethyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Definitions
- - X represents one or more substituents chosen from a halogen atom, a hydrogen atom, a C1-C4 alkyl group, or a C1-C4 alkoxy group:
- - R represents a C3-C10 cycloalkyl, monocyclic or polycyclic radical . or a phenyl group substituted or not by one or more substituents chosen from a halogen atom, a C-- -C4 alkyl group, or a C1-C4 alkoxy group.
- the invention also relates to the salts of the compounds of general formula 1 with pharmaceutically acceptable mineral or organic acids.
- the acid used can be, by way of nonlimiting example, hydrochloric acid, maleic acid, fumaric acid, or p-toluenesulfonic acid.
- the present invention relates more particularly to the compounds of general formula 1, chosen from: Benzoyl-1 (2-phenoxy-ethylaminomethyl) -4 piperidine Benzyl-1 (2-phenoxy-ethylaminomethyl) -4 piperidine (3-methyl benzoyl) - 1 (phenoxy -2 ethylaminomethyl) -4 piperidine (3-methyl benzyl) -l (2-phenoxy ethylaminomethyl) -4 piperidine (3-methoxy benzoyl) - 1 (2-phenoxy ethylaminomethyl) -4 piperidine (3-methoxy benzyl) -l ( 2-phenoxyethylaminomethyl) -4 piperidine (3-Chloro benzoyl) - 1 (2-phenoxy ethylaminomethyl) -4 piperidine (3-Chloro benzyl) -l (2-phenoxy ethylaminomethyl) -4 piperidine (3-Chloro benzy
- - Y represents a nucleofuge group such as methylsulfonyloxy, benzenesulfonyloxy, or p-toluenesulfonyloxy.
- n and R are defined as above.
- the displacement experiments are carried out as described by Sleight and Peroutka fNauvn-Schmiedebere Arch. Pharmaco 343. 106-116, 1991). All the dilutions of the products to be studied are made in the reaction buffer.
- the reaction tubes contain 0J ml of [ 3 H] 8-OH-DPAT (0.2 nM), 0J ml of product to be tested 6-7 concentrations (successive dilutions to 1/10) and 0.8 ml of tissue. If the alleged affinity of the products is in the nanomolar range, the lowest concentration tested is 10 " * M, if the product has a presumed low affinity, the highest concentration tested is ÎO " ⁇ M.
- reaction tubes are incubated at 23 ° C for 30 minutes then quickly filtered under vacuum on Whatman GF / B filters, the tubes are rinsed with 2 x 5 ml of Tris-HCl buffer (50 mM, pH 7.4 at 25 ° C).
- the radioactivity collected on the filter is analyzed in liquid scintillation by adding 4 ml of scintillating liquid (Emulsifier Safe, Packard). All the experiments are carried out in triplicate and repeated at least 3 times.
- SUBSTITUTE SHEET (RULE 26) The results of the tests show that the compounds of the invention have a high affinity for serotonergic receptors of the 5-HTJA type. Also, the compounds of the invention can be useful for the treatment of anxiety, depression, disorders. sleep, for the regulation of food intake, for the regulation of gastric secretion, and for the treatment of vascular, cardiovascular and cerebrovascular disorders such as hypertention or migraine.
- Pharmaceutical preparations containing these active ingredients can be shaped for oral, rectal or parenteral administration, for example in the form of capsules, tablets, granules, capsules, liquid solutions, syrups or oral suspensions, and contain the suitable excipients. It is also possible to combine it with other active pharmaceutical and therapeutically acceptable ingredients.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP94908368A EP0687252A1 (en) | 1993-03-04 | 1994-02-24 | 2-phenoxyethylamine derivatives, their preparation and their therapeutical use |
CA002152400A CA2152400A1 (en) | 1993-03-04 | 1994-02-24 | New 2-phenoxyethanamine derivatives; process for preparing them and their use as therapeutic agents |
JP6519644A JPH08507302A (en) | 1993-03-04 | 1994-02-24 | Novel 2-phenoxyethylamine derivatives, their preparation and their therapeutic use |
AU61435/94A AU6143594A (en) | 1993-03-04 | 1994-02-24 | Novel 2-phenoxy ethylamine derivatives, their preparation and their therapeutical use |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9302502A FR2702211B1 (en) | 1993-03-04 | 1993-03-04 | New derivatives of 2-phenoxyethylamine, their preparation and their therapeutic use. |
FR93/02502 | 1993-03-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1994020466A1 true WO1994020466A1 (en) | 1994-09-15 |
Family
ID=9444650
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR1994/000202 WO1994020466A1 (en) | 1993-03-04 | 1994-02-24 | Novel 2-phenoxy ethylamine derivatives, their preparation and their therapeutical use |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP0687252A1 (en) |
JP (1) | JPH08507302A (en) |
AU (1) | AU6143594A (en) |
CA (1) | CA2152400A1 (en) |
FR (1) | FR2702211B1 (en) |
WO (1) | WO1994020466A1 (en) |
ZA (1) | ZA941532B (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2769629A1 (en) * | 1997-10-09 | 1999-04-16 | Synthelabo | New azabicyclooctane-methanamine derivatives having affinity for dopaminergic and serotoninergic receptors, used e.g. for treating psychosis, anxiety or depression |
WO1999019325A1 (en) * | 1997-10-09 | 1999-04-22 | Sanofi-Synthelabo | 8-azabicyclo [3.2.1] octane-3-methanamine derivatives as ligands of d2 and d3 dopamine and 5ht1a and 5ht2 serotonin receptors |
WO2000058282A2 (en) * | 1999-03-29 | 2000-10-05 | Pierre Fabre Medicament | Novel [(2-substituted-5 -[3-thienyl) -benzyl]-[2- ([2-isopropoxy-5-fluoro] -phenoxy) -ethyl] -amine derivatives, method for the production and use thereof as medicaments |
CN109563073A (en) * | 2016-06-24 | 2019-04-02 | 诺罗利西斯公司 | For treating to 5-HT1AThe serotonergic of receptor control adjusts the compound of sensitive disease |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2786767B1 (en) * | 1998-12-02 | 2001-02-23 | Pf Medicament | NOVEL 3-ALKOXYBENZYLAMINE DERIVATIVES AND THEIR USE AS MEDICAMENTS FOR THE TREATMENT OF SCHIZOPHRENIA |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0445026A1 (en) * | 1990-02-27 | 1991-09-04 | Adir Et Compagnie | Aminomethylpiperidine derivatives, their process for preparation and the pharmaceutical compositions containing them |
EP0522914A1 (en) * | 1991-06-27 | 1993-01-13 | Synthelabo | 2-Piperidinylpyrimidin-4-carboxamide derivatives, their preparation and their application in therapy |
-
1993
- 1993-03-04 FR FR9302502A patent/FR2702211B1/en not_active Expired - Fee Related
-
1994
- 1994-02-24 CA CA002152400A patent/CA2152400A1/en not_active Abandoned
- 1994-02-24 AU AU61435/94A patent/AU6143594A/en not_active Abandoned
- 1994-02-24 EP EP94908368A patent/EP0687252A1/en not_active Withdrawn
- 1994-02-24 WO PCT/FR1994/000202 patent/WO1994020466A1/en not_active Application Discontinuation
- 1994-02-24 JP JP6519644A patent/JPH08507302A/en active Pending
- 1994-03-04 ZA ZA941532A patent/ZA941532B/en unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0445026A1 (en) * | 1990-02-27 | 1991-09-04 | Adir Et Compagnie | Aminomethylpiperidine derivatives, their process for preparation and the pharmaceutical compositions containing them |
EP0522914A1 (en) * | 1991-06-27 | 1993-01-13 | Synthelabo | 2-Piperidinylpyrimidin-4-carboxamide derivatives, their preparation and their application in therapy |
Non-Patent Citations (2)
Title |
---|
H. DABIRÉ ET AL.: "S14063: a new potent 5-HT1a receptor antagonist devoid of beta-adrenoceptor blocking properties", EUR. J. PHARMACOL., vol. 203, no. 2, 15 October 1991 (1991-10-15), (EJPHAZ,00142999); FAC. MED. BROUSSAIS HOTEL-DIEU, PARIS; 75270 FR., pages 323 - 324 * |
See also references of EP0687252A1 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2769629A1 (en) * | 1997-10-09 | 1999-04-16 | Synthelabo | New azabicyclooctane-methanamine derivatives having affinity for dopaminergic and serotoninergic receptors, used e.g. for treating psychosis, anxiety or depression |
WO1999019325A1 (en) * | 1997-10-09 | 1999-04-22 | Sanofi-Synthelabo | 8-azabicyclo [3.2.1] octane-3-methanamine derivatives as ligands of d2 and d3 dopamine and 5ht1a and 5ht2 serotonin receptors |
US6221879B1 (en) | 1997-10-09 | 2001-04-24 | Sanofi-Synthelabo | 8-azabicyclo[3.2.1] octane-3-methanamine derivatives as ligands of D2 and D3 dopamine and 5HT1A and 5HT2 serotonin receptors |
WO2000058282A2 (en) * | 1999-03-29 | 2000-10-05 | Pierre Fabre Medicament | Novel [(2-substituted-5 -[3-thienyl) -benzyl]-[2- ([2-isopropoxy-5-fluoro] -phenoxy) -ethyl] -amine derivatives, method for the production and use thereof as medicaments |
FR2791676A1 (en) * | 1999-03-29 | 2000-10-06 | Pf Medicament | NOVEL [(2-SUBSTITUTED-5- [THIENYL]) - BENZYL] - [2 - ([ISOPROPOXY-5-FLUORO] -PHENOXY) ETHYL] -AMINE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR USE AS MEDICAMENTS |
WO2000058282A3 (en) * | 1999-03-29 | 2002-01-03 | Pf Medicament | Novel [(2-substituted-5 -[3-thienyl) -benzyl]-[2- ([2-isopropoxy-5-fluoro] -phenoxy) -ethyl] -amine derivatives, method for the production and use thereof as medicaments |
US6417222B1 (en) * | 1999-03-29 | 2002-07-09 | Pierre Fabre Medicament | [2-substituted-5-[3-thienyl)-benzyl]-2- ([2-isopropoxy-5-fluoro]-phenyoxy)-ethyl]-amine derivatives, method for the production and use thereof as medicaments |
CN109563073A (en) * | 2016-06-24 | 2019-04-02 | 诺罗利西斯公司 | For treating to 5-HT1AThe serotonergic of receptor control adjusts the compound of sensitive disease |
Also Published As
Publication number | Publication date |
---|---|
AU6143594A (en) | 1994-09-26 |
EP0687252A1 (en) | 1995-12-20 |
JPH08507302A (en) | 1996-08-06 |
CA2152400A1 (en) | 1994-09-15 |
FR2702211A1 (en) | 1994-09-09 |
ZA941532B (en) | 1994-10-06 |
FR2702211B1 (en) | 1995-06-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0434561B1 (en) | 1-Naphthyl-piperazine derivatives, process for their preparation and pharmaceutical compositions containing them | |
FR2681325A1 (en) | DERIVATIVES OF AMINOMETHYL-4 PIPERIDINE, THEIR PREPARATION AND THEIR THERAPEUTIC USE. | |
EP0429341A2 (en) | Heterocyclic derivatives, their preparation and pharmaceuticals containing them | |
EP0307303A1 (en) | 1-[(2-Pyrimidinyl)-aminoalkyl] piperidines, their preparation and their use in therapy | |
EP0433149A2 (en) | Serotonin antagonists, their preparation and pharmaceuticals containing them | |
EP0332528A1 (en) | Isoindolinone derivatives, processes for their preparation and medicines containing them | |
FR2699918A1 (en) | Selective ligands of 5HY1D-5HT1B receptors derived from indole-piperazine useful as drugs. | |
FR2468601A1 (en) | NEW FLAVANNE DERIVATIVES USEFUL IN PARTICULAR AS ANTI-CONVULSANTS | |
EP0447292A1 (en) | 4-Aminomethyl-piperidine derivatives, their preparation and therapeutic application | |
EP0461986B1 (en) | Derivatives of hexahydroazepines, procedure for their preparation and pharmaceutical compositions containing same | |
EP0351255B1 (en) | Derivatives of 2-[(4-piperidinyl)methyl]-1,2,3,4-tetrahydroisoquinoline, their preparation and their use in therapy | |
WO1994020466A1 (en) | Novel 2-phenoxy ethylamine derivatives, their preparation and their therapeutical use | |
EP0683775A1 (en) | Heterocyclic 4-aminomethylpiperidine derivatives, their preparation and application in therapy | |
EP0632035B1 (en) | Aminoalkylchomones, process for their preparation and pharmaceutical compositions containing them | |
EP0577470B1 (en) | 2-Amino-N-[[[4-(aminocarbonyl)pyrimidin-2-yl]amino]alkyl]-pyrimidine-4-carboxamide derivates, their preparation and their use in therapeutics | |
EP0302787B1 (en) | 2-Methyl(4-piperidinyl)-benzofuro[2,3-c] pyridines, their preparation and therapeutical use | |
EP1023287B1 (en) | 3-oxo-2(h)-1,2,4-triazine derivatives as ligands of 5ht1a receptors | |
EP0520882B1 (en) | 2-Aminopyrimidin-4-carboxamide derivatives, their preparation and their application in therapy | |
EP0266246A1 (en) | Imidazo[4,5-b]pyridone-2 derivatives, their preparation and their therapeutical use | |
EP0461012B1 (en) | (1-Phenylpyrrolidin-2-yl)methylpiperazine derivatives, process for their preparation and their use in therapy | |
EP0351283A1 (en) | 2-[(4-Piperidinyl)methyl]-2,3-dihydro-1H-isoindole and 2,3,4,5-tetrahydro-1H-benzazepine derivatives, their preparation and therapeutical use | |
EP0522914A1 (en) | 2-Piperidinylpyrimidin-4-carboxamide derivatives, their preparation and their application in therapy | |
EP0017523B1 (en) | Dithiepinno (1,4)(2,3-c) pyrrol derivatives, their preparation and pharmaceutical compositions containing them | |
EP0106860B1 (en) | New carboxamidoguanidins, method for obtaining them and pharmaceutical compositions containing them | |
EP0157762B1 (en) | New substituted piperidinoguanidines, preparation process and pharmaceutical compositions containing them |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AU CA JP NZ US |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE |
|
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2152400 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1994908368 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 262129 Country of ref document: NZ |
|
ENP | Entry into the national phase |
Ref country code: US Ref document number: 1995 507406 Date of ref document: 19950828 Kind code of ref document: A Format of ref document f/p: F |
|
WWP | Wipo information: published in national office |
Ref document number: 1994908368 Country of ref document: EP |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: 1994908368 Country of ref document: EP |