CH527825A - Multi-activity salts - from antirheumatic pyrazolidines and analgesic bases - Google Patents
Multi-activity salts - from antirheumatic pyrazolidines and analgesic basesInfo
- Publication number
- CH527825A CH527825A CH932371A CH932371A CH527825A CH 527825 A CH527825 A CH 527825A CH 932371 A CH932371 A CH 932371A CH 932371 A CH932371 A CH 932371A CH 527825 A CH527825 A CH 527825A
- Authority
- CH
- Switzerland
- Prior art keywords
- pyrazolidine
- butyl
- derivative
- basic compound
- salt
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 16
- 230000000202 analgesic effect Effects 0.000 title claims abstract description 7
- 230000003356 anti-rheumatic effect Effects 0.000 title claims abstract description 6
- 150000003218 pyrazolidines Chemical class 0.000 title claims 2
- 239000003435 antirheumatic agent Substances 0.000 title abstract description 4
- 230000000694 effects Effects 0.000 title abstract 3
- 229910052751 metal Inorganic materials 0.000 claims abstract description 9
- 239000002184 metal Substances 0.000 claims abstract description 9
- 230000001754 anti-pyretic effect Effects 0.000 claims abstract description 6
- 239000002221 antipyretic Substances 0.000 claims abstract description 6
- 230000002378 acidificating effect Effects 0.000 claims abstract description 5
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 4
- XNRSKGIZSJZJNB-UHFFFAOYSA-N 1-(5-oxohexyl)pyrazolidine-3,5-dione Chemical compound C(C)(=O)CCCCN1NC(CC1=O)=O XNRSKGIZSJZJNB-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract 4
- 239000011707 mineral Substances 0.000 claims abstract 4
- 150000007524 organic acids Chemical class 0.000 claims abstract 2
- 150000007514 bases Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 230000001747 exhibiting effect Effects 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- -1 organic acid salt Chemical class 0.000 claims description 5
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- JHRGJMLMFWJXOG-UHFFFAOYSA-N 1-phenylpyrazolidine-3,5-dione Chemical compound N1C(=O)CC(=O)N1C1=CC=CC=C1 JHRGJMLMFWJXOG-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000001449 anionic compounds Chemical class 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 150000002891 organic anions Chemical class 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims 3
- 239000012736 aqueous medium Substances 0.000 claims 2
- 238000004821 distillation Methods 0.000 claims 2
- 238000001704 evaporation Methods 0.000 claims 2
- 230000008020 evaporation Effects 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- 239000002609 medium Substances 0.000 claims 2
- 238000000859 sublimation Methods 0.000 claims 2
- 230000008022 sublimation Effects 0.000 claims 2
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 239000003158 myorelaxant agent Substances 0.000 abstract description 5
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 abstract 2
- 230000002411 adverse Effects 0.000 abstract 1
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzydamine Chemical compound C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical compound O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 2
- 230000001670 myorelaxant effect Effects 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 239000002036 chloroform fraction Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/28—Two oxygen or sulfur atoms
- C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
- C07D231/32—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Salts having antirheumatic, anti-inflammatory, analgesic, antipyretic and muscle relaxant activity are prepd. by reacting a metal salt of an antirheumatic acidic pyrazolidine deriv. (pref. 4-butyl-1,2-diphenyl-, 4-butyl-1- phenyl-, 4-butyl-1,2-p-hydroxyphenyl- or 4-acetyl-butyl-3,5-pyrazolidinedione) with a mineral or organic salt of a basic cpd. having antipyretic, analgesic and muscle relaxant activity (pref. a 1-benzyl-3-(3-dimethylaminopropoxy)-1H-indazole) under conditions such that either the salt formed between the metal and the mineral or organic acid or the salt formed between the pyrazolidine and the basic cpd. separates out, the reaction being carried out under conditions of light, temp. and pH which do not adversely affect the stability of the prod. or its components.
Description
Procédé de fabrication de composés présentant une action thérapeutique
La présente invention a trait à un procédé de préparation de composés à action thérapeutique multiple (antirhumatismale, anti-mflammatoire, analgésique, antipyrétique et myo-relaxante). Particulièrement de dérivés pyrazolidiniques (4-butyl- 1 ,2-diphényl-3,5 pyrazolidne- dione, 4-butyl-l phényl-3,5 pyrazolidine-dione, 4-butyl1.2-p-hydroxyphényl-3,5 pyrazolidine-dione, 4-acétyl-butyl-3,5 pyrazolidine-dione) par salification de ces derniers avec un composé basique présentant un pouvoir anti-inflammatoire, antipyrétique, analgésique, et myorelaxant, tels que le l-benzyl-3-[3-diméthylamino3 propoxy) 1 H-indozole ou un autre composé basique.
Le procédé de fabrication d'un composé présentant une action thérapeutique à partir d'un dérivé pyrazolidinique acide présentant une action antirhumatismale et d'un composé basique présentant un pouvoir antipyrétique, analgésique et myo-relaxant, est caractérisé en ce qu'on fait réagir un sel métallique du dérivé pyrazolidinique acide avec un sel d'acide minéral ou organique du composé basique choisi, de manière que le sel métallique formé entre l'anion minéral ou organique séparé de ce composé basique et le métal séparé du dérivé pyrazolidinique acide reste en solution dans le milieu réactionnel ou bien précipité, tandis que le composé pyrazolidinque du composé basique choisi y est insolubilisé ou bien reste en solution, respectivement selon la polarité du milieu utilisé comme solvant, cette réaction étant effectuée dans des conditions de luminosité,
de température et de pH qui ne compromettent pas la stabilité du composé résultant ou de ses constituants et de façon à pouvoir isoler le composé obtenu du milieu de réaction.
Les exemples ci-dessous illustrent le procédé selon l'invention.
Exemple 1
A 150 cc d'eau distillée maintenue sous agitation vigoureuse, on ajoute simultanément 61,6g (0,2 mole) de 4-butyl-l-phényl-3,5 pyrazolidine-dione et 100cc de solution de soude caustique 2N (0,2 mole), Cette solution et celle obtenue en dissolvant 69,18 g (0,2 mole) de chlorhydrate de l-benzyl-3[3-(dilméthylamino) propoxy] 1 H-indozole dans 250 cc d'eau sont ajoutées goutte à goutte à la même vitesse à 400 cc d'eau distillée maintenue sous forte agitation mécanique.
Une fois cette addition terminée, on laisse reposer la solution avec le précipité formé pendant 48 h à 0O C.
La phase liquide est décantée et le résidu trituré et lavé avec un litre d'eau. Le résidu séché à 500 C et sous un vide de 10 mm de Hg pèse environ 120 g (rendement 98 à 99 %). Le sel de formule (C38H43N503) ainsi obtenu est un produit solide blanc, insoluble dans l'eau et dans l'éther de pétrole, soluble dans le méthanol,
I'éthanol, l'acétone, le chloroforme, le benzène et d'autres dissolvants organiques. La pureté de ce produit est de 99 à 100 % et son point de fusion de 1070 C.
Exemple 2
1,625 g (0,007 mole) de 4-butyl-1-phényl-3,5 pyrazolidine-dione sont mis en suspension dans 30 cc d'eau et on ajoute lentement à cette suspension 70 cc de solution de soude caustique 0,1N (0,007 mole) et on continue d'agiter jusqu'à dissolution complète.
2,42 g (0,007 mole) de chlorhydrate de l-benzyl 3-[3-(dimethylaminov propoxy] 1 H-indozole sont dissous dans 100 cc d'eau. Cette solution est ajoutée goutte à goutte, simultanément avec la précédente, à 50 cc d'eau maintenue sous agitation et à la fin de cette addition on laisse reposer le tout à 00 C pendant 24 h. La phase solide qui se sépare du liquide surnageant est alors lavée à l'eau et séchée sous un vide de 10 mm de Hg à 400 C.
On obtient ainsi 3,5 g d'un produit blanc de point de fusion de 100 à 1020 C et de formule Q2H59N5O3.
Exemple 3
Sur 12,33 g (0,04 mole) de 4-butyl- 1,2-diphényl-3,5 pyrazolidine-dione maintenue en suspension dans 50cc d'eau distillée sous forte agitation, on ajoute 40 cc de solution de soude caustique 1 N (0,04 mole) très exactement. Sur cette solution, on verse lentement et sous agitation, une solution de 13,83 g (0,04 mole) de chlorhydrate de 1 benzyl-3-[3-(diméthylamino)propoxy] i Hindozole dans 50cc d'eau.
Le résidu est extrait avec trois fractions de chloroforme d'un total de 120 cc. Les extraits chloroformiques réunis sont lavés avec 20 cc d'eau, sont séchés sur sulfate de soude anhydre et concentrés sous vide. On laisse ensuite reposer le liquide jusqu'à ce qu'il cristallise. Le produit obtenu est pulvérisé et séché à nouveau à 400 C sous vide de 10 mm de Hg.
Exemple 4
On dissout 6,16 g (0,02 mole) de 4-butyl-1,2-diphé- nyl-3,5 pyrazolidine-dione dans 50 cc d'acétone et on mélange cette solution avec une solution de 6,91 g (0,02 mole) de chlorhydrate de l-benzyl-3-[3-(diméthylami- no)propoxy] 1 H-indozole dans 40 cc de méthanol. Sur ce mélange maintenu sous forte agitation, on ajoute 10 cc d'une solution méthanolique de soude caustique 2N (0,02 mole) très exactement. On laisse reposer à l'abri de la lumière pendant 12h et on filtre; le résidu est lavé avec 30 cc d'acétone et on élimine le dissolvant à moins de 500 C sous vide de 15 mm de Hg jusqu'à siccité. Le produit ainsi obtenu est finement pulvérisé et séché à nouveau sous vide à 400 C.
Exemple 5
On laisse reposer la suspension aqueuse du sel de drate de l-benzyl-3-[3-(diméthylamino3propoxy] 1 Hobtenue aux exemples 1, 2 ou 3, on sépare la phase solide de la phase aqueuse et on lave le résidu à l'eau; on dissout ensuite ce résidu dans du méthanol, de l'alcool ou de l'acétone et on sèche cette solution sur du sulfate de soude anhydre. Après filtration, on évapore le solvant à une température inférieure à 500 C sous vide de 15 mm de Hg. Le résidu est ensuite pulvérisé et séché à nouveau à 400 C.
Exemple 6
Sur la solution aqueuse de sel sodique de 4-butyl-1,2diphényl-3,5 pyrazolidine-dione obtenue aux exemples 1, 2 ou 3, on verse une solution équimoléculaire de chlorhy drate de 1 benzyl - 3- - (diméthylamino)propoxy] 1H - indozole en milieu hydrométhanolique, hydroéthanolique ou hydroacétonique. On laisse reposer jusqu'à ce que le chlorure de sodium formé se sépare par sédimentation et on traite la solution de sel de l-benzyl-3-[3-(diméthyl-amino)propoxy] 1 H-indozole, comme indiqué dans les exemples précédents.
Exemple 7
Les sels de i -benzyl-3 - [3 -(diméthylamino)pro- poxy]lH-indozole obtenus selon les exemples 1 à 6 sont purifiés par dissolution dans de l'alcool, du méthanol ou de l'acétone et reprécipitation à l'eau.
Process for the production of compounds exhibiting therapeutic action
The present invention relates to a process for the preparation of compounds with multiple therapeutic action (antirheumatic, anti-inflammatory, analgesic, antipyretic and myo-relaxant). Particularly of pyrazolidinic derivatives (4-butyl-1, 2-diphenyl-3,5 pyrazolidne-dione, 4-butyl-l phenyl-3,5 pyrazolidine-dione, 4-butyl1.2-p-hydroxyphenyl-3,5 pyrazolidine -dione, 4-acetyl-butyl-3,5 pyrazolidine-dione) by salification of the latter with a basic compound exhibiting anti-inflammatory, antipyretic, analgesic and muscle relaxant power, such as 1-benzyl-3- [3 -dimethylamino3 propoxy) 1 H-indozole or another basic compound.
The process for the manufacture of a compound exhibiting a therapeutic action from an acid pyrazolidinic derivative exhibiting an antirheumatic action and a basic compound exhibiting an antipyretic, analgesic and myo-relaxant power, is characterized by reacting a metal salt of the acidic pyrazolidinic derivative with an inorganic or organic acid salt of the selected basic compound, so that the metal salt formed between the inorganic or organic anion separated from this basic compound and the metal separated from the acidic pyrazolidinic derivative remains in solution in the reaction medium or else precipitated, while the pyrazolidinque compound of the basic compound chosen is insolubilized therein or else remains in solution, respectively depending on the polarity of the medium used as solvent, this reaction being carried out under light conditions,
temperature and pH which do not compromise the stability of the resulting compound or its constituents and so as to be able to isolate the compound obtained from the reaction medium.
The examples below illustrate the process according to the invention.
Example 1
To 150 cc of distilled water kept under vigorous stirring, 61.6 g (0.2 mol) of 4-butyl-1-phenyl-3,5-pyrazolidine-dione and 100 cc of 2N caustic soda solution (0, 2 mol), This solution and that obtained by dissolving 69.18 g (0.2 mol) of 1-benzyl-3 [3- (dilmethylamino) propoxy] 1 H-indozole hydrochloride in 250 cc of water are added dropwise. drop at the same speed to 400 cc of distilled water maintained under strong mechanical stirring.
Once this addition is complete, the solution is left to stand with the precipitate formed for 48 h at 0O C.
The liquid phase is decanted and the residue triturated and washed with one liter of water. The residue, dried at 500 ° C. and under a vacuum of 10 mm Hg, weighs about 120 g (yield 98 to 99%). The salt of formula (C38H43N503) thus obtained is a white solid product, insoluble in water and in petroleum ether, soluble in methanol,
Ethanol, acetone, chloroform, benzene and other organic solvents. The purity of this product is 99-100% and its melting point is 1070 C.
Example 2
1.625 g (0.007 mole) of 4-butyl-1-phenyl-3,5 pyrazolidine-dione are suspended in 30 cc of water and slowly added to this suspension 70 cc of 0.1N caustic soda solution (0.007 mole) and stirring is continued until complete dissolution.
2.42 g (0.007 mole) of 1-benzyl 3- [3- (dimethylaminov propoxy] 1 H-indozole hydrochloride are dissolved in 100 cc of water. This solution is added dropwise, simultaneously with the previous one, to 50 cc of water maintained under stirring and at the end of this addition the whole is left to stand at 00 ° C. for 24 h. The solid phase which separates from the supernatant liquid is then washed with water and dried under a vacuum of 10 mm of Hg at 400 C.
3.5 g of a white product with a melting point of 100 to 1020 C and of formula Q2H59N5O3 are thus obtained.
Example 3
On 12.33 g (0.04 mole) of 4-butyl-1,2-diphenyl-3,5 pyrazolidine-dione kept in suspension in 50 cc of distilled water with vigorous stirring, 40 cc of caustic soda solution are added 1 N (0.04 mol) exactly. A solution of 13.83 g (0.04 mol) of 1 benzyl-3- [3- (dimethylamino) propoxy] i Hindozole hydrochloride in 50 cc of water is poured slowly and with stirring onto this solution.
The residue is extracted with three chloroform fractions totaling 120 cc. The combined chloroform extracts are washed with 20 cc of water, dried over anhydrous sodium sulfate and concentrated in vacuo. The liquid is then allowed to stand until it crystallizes. The product obtained is pulverized and dried again at 400 ° C. under a vacuum of 10 mm Hg.
Example 4
6.16 g (0.02 mol) of 4-butyl-1,2-diphenyl-3,5 pyrazolidine-dione are dissolved in 50 cc of acetone and this solution is mixed with a solution of 6.91 g (0.02 mole) of 1-benzyl-3- [3- (dimethylamine) propoxy] 1 H-indozole hydrochloride in 40 cc of methanol. To this mixture, kept under vigorous stirring, is added 10 cc of a methanolic solution of 2N caustic soda (0.02 mol) very precisely. Leave to stand in the dark for 12 hours and filter; the residue is washed with 30 cc of acetone and the solvent is removed at less than 500 ° C. under a vacuum of 15 mm Hg until dry. The product thus obtained is finely pulverized and dried again under vacuum at 400 C.
Example 5
The aqueous suspension of the 1-benzyl-3- [3- (dimethylamino3propoxy] drate salt is allowed to stand in Examples 1, 2 or 3, the solid phase is separated from the aqueous phase and the residue is washed with water. water; this residue is then dissolved in methanol, alcohol or acetone and this solution is dried over anhydrous sodium sulfate. After filtration, the solvent is evaporated off at a temperature below 500 ° C. under a vacuum of 15 ° C. mm Hg. The residue is then pulverized and dried again at 400 ° C.
Example 6
On the aqueous solution of sodium salt of 4-butyl-1,2-diphenyl-3,5-pyrazolidine-dione obtained in Examples 1, 2 or 3, an equimolecular solution of 1-benzyl - 3- - (dimethylamino) propoxy hydrochloride is poured. ] 1H - indozole in hydromethanolic, hydroethanolic or hydroacetonic medium. It is left to stand until the sodium chloride formed separates out by sedimentation and the solution of 1-benzyl-3- [3- (dimethyl-amino) propoxy] 1 H-indozole salt is treated as indicated in previous examples.
Example 7
The salts of i -benzyl-3 - [3 - (dimethylamino) propoxy] 1H-indozole obtained according to Examples 1 to 6 are purified by dissolving in alcohol, methanol or acetone and reprecipitation with l 'water.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES384735A ES384735A1 (en) | 1970-10-21 | 1970-10-21 | Procedure for obtaining piazolidinic derivatives with therapeutic action. (Machine-translation by Google Translate, not legally binding) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH527825A true CH527825A (en) | 1972-09-15 |
Family
ID=8457068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH932371A CH527825A (en) | 1970-10-21 | 1971-06-25 | Multi-activity salts - from antirheumatic pyrazolidines and analgesic bases |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH527825A (en) |
| ES (1) | ES384735A1 (en) |
-
1970
- 1970-10-21 ES ES384735A patent/ES384735A1/en not_active Expired
-
1971
- 1971-06-25 CH CH932371A patent/CH527825A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES384735A1 (en) | 1973-09-01 |
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