EP0445116A1 - [(aryl-4-piperazinyl-1)-2-ethoxy]-3p-cymole, die ortho-, meta-, para-monosubstituierten oder disubstituierten derivate, das verfahren zu deren herstellung und die diese verbindungen als aktives prinzip enthaltenden arzneimittel - Google Patents

[(aryl-4-piperazinyl-1)-2-ethoxy]-3p-cymole, die ortho-, meta-, para-monosubstituierten oder disubstituierten derivate, das verfahren zu deren herstellung und die diese verbindungen als aktives prinzip enthaltenden arzneimittel

Info

Publication number
EP0445116A1
EP0445116A1 EP89907194A EP89907194A EP0445116A1 EP 0445116 A1 EP0445116 A1 EP 0445116A1 EP 89907194 A EP89907194 A EP 89907194A EP 89907194 A EP89907194 A EP 89907194A EP 0445116 A1 EP0445116 A1 EP 0445116A1
Authority
EP
European Patent Office
Prior art keywords
product
cymene
ethoxy
piperazinyl
mole
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.)
Pending
Application number
EP89907194A
Other languages
English (en)
French (fr)
Inventor
Patrick Houziaux
Jean-Pierre Riffaud
Jean-Yves Lacolle
Bernard Danree
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Institut de Recherches Chimiques et Biologiques Appliquees SARL IRCEBA
Original Assignee
Institut de Recherches Chimiques et Biologiques Appliquees SARL IRCEBA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Institut de Recherches Chimiques et Biologiques Appliquees SARL IRCEBA filed Critical Institut de Recherches Chimiques et Biologiques Appliquees SARL IRCEBA
Publication of EP0445116A1 publication Critical patent/EP0445116A1/de
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/112—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

Definitions

  • the present invention relates, as new products to [(phenyl-4-piperazinyl-1) -2 ethoxy] -3 p-cymene and its ortho meta derivatives, para monosubstituted or disubstituted on the phenyl nucleus, a process for the preparation of these derivatives; it also relates to medicaments containing, as active principle, at least one of said compounds.
  • R 1 , R 2 identical or different, being chosen from a hydrogen atom, a halogen atom or a hydroxyl radical, alkyl having from 1 to 4 carbon atoms, alkoxy having from 1 to 5 carbon atoms, phenoxy , benzyloxy, trifluoromethyl, acetyl.
  • the alkyl or alkoxy groups may be straight or branched chain groups.
  • alkyl group having from 1 to 5 carbon atoms is for example a methyl, ethyl, propyl, isopropyl, butyl, sec-butyl or tert-butyl group, preferably methyl.
  • An alkoxy group having from 1 to 5 carbon atoms is for example a methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, neopentoxy, pentoxy, isopentoxy group, preferably ethoxy or is
  • a halogen atom is preferably an atom of chlorine.
  • the products according to the invention can also be in the form of the salts of the products of formula (I) with a pharmaceutically acceptable, mineral acid such as for example hydrochloric acid or sulfuric or organic acid such as for example citric acid, tartaric, malic, maleic, fumaric, or sulphonic methane.
  • p-cymene is substituted only at 3 by an alkoxy. It is therefore a derivative of thymol and therefore the compound is original.
  • the products of the invention are made from (2-chloroethoxy) 3-p-cymene of formula (II) and (substituted phenyl) -1 piperazine of formula (III) according to the following general reaction scheme:
  • R 1 and R 2 being defined above.
  • the number of moles of compound (III) is approximately double the number of moles of compound (II).
  • the pharmaceutically acceptable salts for example hydrochlorides, are obtained in a known manner by bringing a solution of the product of formula (I) into contact with the acid in question (for example by bubbling hydrochloric acid in a solution of the product of formula (I)).
  • these salts may contain one or two moles of salifying acid per mole of product of formula (I).
  • the present invention also relates to the medicaments characterized in that they contain, as active product, at least one product of formula (I); said drugs can be useful especially in the field of urology.
  • Said crystals have a melting point F BK of
  • Said crystals have a melting point F BK of
  • thermometer 100 ml three-necked flask, equipped with a condenser, a magnetic stirrer and a thermometer:
  • the mixture is heated at 140 ° C for 5 hours.
  • reaction medium After cooling to room temperature, the reaction medium is poured onto a 10% sodium bicarbonate solution. The aqueous phase obtained is extracted with 2 times 100 ml of methylene chloride. The combined organic phases are washed with water saturated with sodium chloride. They are then dried over sodium sulfate. After filtration, the solvent is removed under vacuum. 56.46 g of crude product are obtained. This is purified by fractional distillation under vacuum (under nitrogen).
  • R 1 acetyl-4 in the form of the hydrochloride.
  • thermometer 100 ml three-necked flask, equipped with a condenser, a magnetic stirrer and a thermometer:
  • the mixture is heated to 145 ° C for 1 hour.
  • reaction medium After cooling to room temperature, the reaction medium is poured onto a 10% sodium bicarbonate solution.
  • the aqueous phase obtained is extracted twice with 100 ml of methylene chloride.
  • the combined organic phases are washed with water saturated with sodium chloride. They are then dried over sodium sulfate.
  • reaction medium is poured onto a solution of sodium bicarbonate
  • the aqueous phase obtained is extracted twice with 100 ml of methylene chloride, the combined organic phases are washed with water saturated with sodium chloride and then dried over sodium sulfate. solvent is removed in vacuo to obtain 44.60 g of crude product. This is purified by fractional distillation under vacuum (under nitrogen).
  • Said crystals have a melting point F BK of
  • reaction medium After cooling to room temperature, the reaction medium is poured onto a 10% sodium bicarbonate solution. The aqueous phase obtained is extracted twice with 100 ml of methylene chloride. The combined organic phases are washed with water saturated with sodium chloride. They are then dried over sodium sulfate. After filtration, the solvent is removed under vacuum. 40.40 g of crude product are obtained.
  • Said crystals have a melting point F BK of 145-150 ° C, IR and NMR spectra in accordance with the proposed structure, an AgNO 3 titer of 97.6%.
  • the aqueous phase obtained is extracted twice with 100 ml of methylene chloride.
  • the combined organic phases are washed with water saturated with sodium chloride. They are then dried over sodium sulfate. After filtration, the solvent is removed under vacuum. 40.61 g of crude product are obtained.
  • Said crystals have a melting point F BK of
  • reaction medium After cooling to room temperature, the reaction medium is poured onto a 10% sodium bicarbonate solution. The aqueous phase obtained is extracted twice with 100 ml of methylene chloride. The combined organic phases are washed with water saturated with sodium chloride. We dry them then on sodium sulfate. After filtration, the solvent is removed under vacuum. 38.40 g of crude product are obtained.
  • Said crystals have a melting point F of 190-192 ° C, IR and NMR spectra in accordance with the proposed structure, an AgNO titer of 99.6%.
  • thermometer 100 ml three-necked flask, equipped with a condenser, a magnetic stirrer and a thermometer:
  • Acute toxicity in mice a) Principle The products were administered orally at a single dose in mice. After a 14-day observation period, mortality was recorded.
  • the stimulation of postsynaptic alpha-adrenergic receptors by norepinephrine causes the isolated vas deferens to contract.
  • the concentration of product is sought in the presence of which the concentration of norepinephrine must be multiplied by two to obtain the same effect as in the absence of said product.
  • the concentration of product is sought in the presence of which the contracting effect of a given concentration of norepinephrine is halved, compared to the contraction induced before the addition of said product.
  • noradrenaline 0.4 mg. Kg -1
  • the prior administration of a substance with an alpha-blocking property makes it possible to reduce this toxicity.
  • ED 50 effective dose 50
  • Neighboring molecules have already been described. They had blocking properties of the ⁇ -1 and ⁇ -adrenergic receptors in the heart and, therefore, had antihypertensive properties.
  • the molecules of the present invention also have blocking properties of the ⁇ -1 receptors but they are especially active at the level of the lower urinary tract and only retain a weak residual action at the cardiac level.
  • the products in accordance with the present invention therefore have very advantageous pharmacological properties and their toxicity is sufficiently low to allow their use in therapy.
  • the products of the invention can therefore be used in human or veterinary medicine, in particular in the treatment of dysurias linked to uretral hypertonia.
  • the products can be administered by the general route (parenteral, oral, rectal) or by topical route.
  • the pharmaceutical compositions containing, as active ingredient, at least one product according to the invention in combination with a pharmaceutically acceptable vehicle can be solid or liquid and can be presented, for example, in the form of injectable preparations, tablets, capsules, granules.
  • the dosage can vary within wide limits, in particular according to the type and severity of the condition to be treated and according to the mode of administration.
  • Such pharmaceutical compositions constitute an object of the invention. Their preparation process is another.
  • the invention relates to the use of the compounds of formula (I) for the preparation of medicaments useful for the treatment of dysurias linked to uretral hypertonia.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Urology & Nephrology (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP89907194A 1988-06-13 1989-06-13 [(aryl-4-piperazinyl-1)-2-ethoxy]-3p-cymole, die ortho-, meta-, para-monosubstituierten oder disubstituierten derivate, das verfahren zu deren herstellung und die diese verbindungen als aktives prinzip enthaltenden arzneimittel Pending EP0445116A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8807864 1988-06-13
FR8807864A FR2632641B1 (fr) 1988-06-13 1988-06-13 ((aryl-4-piperazinyl-1)-2 ethoxy)-3 p-cymene, les derives ortho, meta, para monosubstitues ou disubstitues sur le noyau phenyle dudit produit, le procede de preparation desdits derives, et les medicaments contenant lesdits composes comme principe actif

Publications (1)

Publication Number Publication Date
EP0445116A1 true EP0445116A1 (de) 1991-09-11

Family

ID=9367221

Family Applications (2)

Application Number Title Priority Date Filing Date
EP89907194A Pending EP0445116A1 (de) 1988-06-13 1989-06-13 [(aryl-4-piperazinyl-1)-2-ethoxy]-3p-cymole, die ortho-, meta-, para-monosubstituierten oder disubstituierten derivate, das verfahren zu deren herstellung und die diese verbindungen als aktives prinzip enthaltenden arzneimittel
EP89401640A Expired - Lifetime EP0347305B1 (de) 1988-06-13 1989-06-13 [(Aryl-4-piperazinyl-1)-2-ethoxy]-3p-cymole, die ortho-, meta-, para-monosubstituierten oder disubstituierten Derivate, das Verfahren zu deren Herstellung und die als aktives Prinzip diese Verbindungen enthaltenden Arzneimittel

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP89401640A Expired - Lifetime EP0347305B1 (de) 1988-06-13 1989-06-13 [(Aryl-4-piperazinyl-1)-2-ethoxy]-3p-cymole, die ortho-, meta-, para-monosubstituierten oder disubstituierten Derivate, das Verfahren zu deren Herstellung und die als aktives Prinzip diese Verbindungen enthaltenden Arzneimittel

Country Status (8)

Country Link
US (1) US5110816A (de)
EP (2) EP0445116A1 (de)
JP (1) JPH03505456A (de)
AT (1) ATE89276T1 (de)
DE (1) DE68906466T2 (de)
DK (1) DK168071B1 (de)
FR (1) FR2632641B1 (de)
WO (1) WO1989012634A1 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4410822A1 (de) * 1994-03-24 1995-09-28 Schering Ag Neue Piperidin-Derivate
CN1067985C (zh) 1994-03-30 2001-07-04 泽里新药工业株式会社 吲哚衍生物及含它们的药物
ES2239766T3 (es) * 1995-01-23 2005-10-01 Daiichi Suntory Pharma Co., Ltd. Alivio o remedio para sintomas causados por enfermedades isquemicas y compuestos de fenilpiperidina utilizados para ello.

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1349636A (fr) * 1962-02-26 1964-01-17 Soc Ind Fab Antibiotiques Sifa Nouveaux dérivés de la pipérazine, et procédé de préparation
CA967965A (en) * 1968-12-24 1975-05-20 Hoffmann-La Roche Limited Aromatic ethers and process for the manufacture thereof
FR2515648A1 (fr) * 1981-11-03 1983-05-06 Cortial Nouvelles (phenyl-4 piperazinylethyl)-2 anilines, leur methode de preparation et leur application therapeutique
FR2515647A1 (fr) * 1981-11-03 1983-05-06 Cortial Nouvelles imines derivees de (phenyl-4 piperazinylethyl)-2 anilines, leur methode de preparation et leur application therapeutique
FR2568878B1 (fr) * 1984-08-07 1986-11-21 Cortial Nouveaux derives de (phenylpiperazinylethylamine ethoxy)-4 phenol, leur methode de preparation et leur application therapeutique
EP0173634B1 (de) * 1984-08-07 1988-08-31 Cortial S.A. 4-(Arylpiperazinylethylaminoethoxy)-phenolderivate, Verfahren zu deren Herstellung und deren therapeutische Verwendung
EP0179009A1 (de) * 1984-09-19 1986-04-23 Cortial S.A. N-1(Aminoalcoxy)-4-isopropyl-5 phenoxy)-2 ethyl-N-4-phenylpiperazine, Verfahren zu ihrer Herstellung und ihre therapeutische Verwendung
DE3604941A1 (de) * 1986-02-17 1987-08-20 Heumann Pharma Gmbh & Co Phenylpiperazinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
FR2595357B1 (fr) * 1986-03-04 1988-07-08 Irceba (piperidino-3 propoxy)-5 p.cymene, les derives acetyl, acetoxy et hydroxy dudit produit, les sels de ces produits, un procede de preparation desdits produits et les medicaments contenant au moins un de ces produits comme principe actif

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8912634A1 *

Also Published As

Publication number Publication date
FR2632641B1 (fr) 1990-10-12
EP0347305B1 (de) 1993-05-12
EP0347305A1 (de) 1989-12-20
DK168071B1 (da) 1994-01-31
WO1989012634A1 (fr) 1989-12-28
US5110816A (en) 1992-05-05
FR2632641A1 (fr) 1989-12-15
DK293890D0 (da) 1990-12-11
DK293890A (da) 1990-12-11
DE68906466D1 (de) 1993-06-17
DE68906466T2 (de) 1993-09-09
JPH03505456A (ja) 1991-11-28
ATE89276T1 (de) 1993-05-15

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Free format text: ??(ARYL-4-PIPERAZINYL-1)-2 ETHOXY -3 P-CYMENE, THE ORTHO, META AND PARA DERIVATIVES MONO- OR DISUBSTITUTED ON THE PHENYL NUCLEUS OF SAID PRODUCT, PROCESS FOR PREPARING SAID DERIV