AU593562B2 - N-oxide of NN-dimethyl ethylamine, a process for its production and the pharmaceutical compositions containing it - Google Patents
N-oxide of NN-dimethyl ethylamine, a process for its production and the pharmaceutical compositions containing it Download PDFInfo
- Publication number
- AU593562B2 AU593562B2 AU60385/86A AU6038586A AU593562B2 AU 593562 B2 AU593562 B2 AU 593562B2 AU 60385/86 A AU60385/86 A AU 60385/86A AU 6038586 A AU6038586 A AU 6038586A AU 593562 B2 AU593562 B2 AU 593562B2
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- AU
- Australia
- Prior art keywords
- oxide
- dimethyl
- compound according
- pharmaceutical compositions
- mineral
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
- C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
- C07C291/04—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
j I I COMMONWEALTH OF AUSTRA 93 6 2 1 PATENTS ACT 1952.69 COMPLETE SPECIFICATION
(ORIGINAL)
Class I t. Class Application Number:, Lodged: 6o3'8'/8 Complete Speclfiratlon Lodged,.
Accepted: Published: 1.
:Rr1orwv: pled Art: V4itt 41eu1an~nmcift nujde uzaee Seftdvl 49, end Is cratmt for pai'ktilg.
*Npme of Applicant: Address of Applicant,, Actual I Aventor: ALBERT ROLLAND S.A.
49, rue Saint Andre des Arts, 75006 Paris, France JEAN-PIERRE LABAUNE 4 dd~ess for Service:i EDWD, WATERS SONSO 60 QUE 8N STREET, MELBOURNE, AUSTRALIA, 3000, Complete Specification for the Invention entitled,.
-t6ML N-OXIDE OF NN-DI1ETR-YL ETHYLAMINE, A PROCESS FOR~ ITS PRODUCTION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING IT The following statement Is a full description of this Invention, Including the best method of performing It known to~: US X1I4 t4 -lamrn N-OXIDE OF NN-DIMETHYL ETWYLAMINE, A PROCESS FOR ITS PRODUCTION AND THE PHARMACEUTICAL COMPOSI- TIONS CONTAINING IT.
This invention relates to a novel derivative of NNdimethyl ethylamine and more particularly to a N-oxide.
This invention specifically provides the N-oxide of 2,2-bis phenoxy NN-dimethyl ethylamine having the formula
CH
0 S CH CH N 2 99 0 This invention also relates to the salts of N-oxide with a mineral or organic acid and more precisely with a strong •acid as hydrochloric acid, hydrobromic acid or sulphuric acid.
The N-oxide of 2,2-bis phenoxy NN-dimethyl ethylamine is a weak base and leads to acid addition salts only with nonreducing strong acids.
4 ethylamine or a salt thereof with a mineral or organic peroxide may also be a hydroperoxide from an alkanol such as tert-butyl peroxide; a hydroperoxide from a ketone such as hexafluoro acetone peroxide; a peracid such as p.nitroperbenzoic acid or 4 choloroperbenzoic acid.
such as methanol, ethanol or an aromatic hydrocarbon such as toluene or xylol or a NN-disubstituted lower alkylamide such as dimethyl for e ormamide or dimethyl acetamide.
l _t i -2- The N-oxide of 2,2- bis phenoxy NN-dimethyl ethylamine and the salts thereof have classical properties of the antidepressive agents in the usual pharmacological tests.
They inhibit the hypothermising action of reserpine and of Apomorphine. They increase the group toxicity induced by injection of yohimbine and they antagonize the despear test in the mice.
Due to their anti-depressive properties, they found a use in human or veterinary medicine in the treatment of the depressive conditions, the psychosis of involution, the maniaco-depressive conditions, the reactional or behavioural depressions. These compounds being very little toxic, the therapeutic margin is very extensive and they may be given *n :4 without any -ear of noxious side-effects (dryness of the 15 mouth or extra-pyramidal effects) which appear often with the antidepressive medicines such as the tricyclic derivatives.
,e The usual dosology of the N-oxide of 2,2-bis phenoxy NN-dimethyl ethylamine may extensively vary depending on the weight and the age of the patient, on the therapeutic use, the oldness of the illness and the route of administration.
It ranges from 0.05 to 0.5 g per unit dosage and from a 0.1 g to 0.5 g per day in the adult man.
In view of the therapeutic use, the N-oxide of 2,2- S 25 bis phenoxy NN-dimethyl amine or the acid addition salts 9 thereof are utilized in the form of pharmaceutical compositions. These contain the said N-oxide or an acid addition salt thereof in combination or in admixture with an inert non-toxic pha-rmaceutically-acceptable carrier or 0 30 vehicle.
The inert carrier or vehicle is one of those suitable for administration by the parenteral, oral, rectal or percutaneous routes of administration. It may in this respect be cited: the untreated or chemically modified starches, the celluloses,the alkyl celluloses, calcium carbonate, magnesium stearate, talc, water or salines, cacao butter or the polyethylene glycol stearates, the polar solvents such as benzyl alcohol or dimethylsulfoxide.
AN
0. Yl-' 3 i e Pi o qe
C,
C*
Ci
OC
Cs
'C
CC
The production of these pharmaceutical compositions is carried out according to the known methods of pharmacotechnology, namely to produce tablets, coated tablets, dragees, soft gelatine capsules, capsules, drops injectible or drinkable solutions, preparations for percutaneous applications.
The following examples are merely intended for illustrating the invention. They do not limit it in any manner.
EXAMPLE I Preparation of the N-oxide of 2,2-bis phenoxy NN-dimethyl ethylamine.
In a three-neck flask of 100 ml fitted with a decantation funnel, a thermometer, a cooling device, 5,15 g (0.02M) of NN-dimethyl-2,2-bis phenoxy ethylamine previously dissolved in 50 ml methanol are introduced to which 6 ml 30% perhydrol are dropwise added. After completion of the addition, stirring at room temperature is kept for 30 mn then the mixture is heated at about 350 for 12 hours.
20 Finally methanol is distilled off and water is discarded by azeotropic distillation with ethanol. The residual oily residue is taken up in either; a white solid matter appears. After filtration and drying 3.08 g N-oxide of NN-dimethyl which melts at 1040C. The yield amounts to 56.5% TLC Rf 0.14 (solvent CHcl 3 -methanol 9 1 RIN spectum in CDC1 3 H m 6,8 7,3) 1 H (t 6,7) 2 H d 3,7 6 H s 3,2 The R.M.N. spectum differs from that of medifoxamine in the shift of I H to t 5,8, 2 H to d: 2,8 and 6 H (s 2,32) PXAMPLE II Study of the pharmacological characteristics of the N-oxide of 2,2 bis phenoxy NN-dimethyl ethylamine, see Table 1 I certfy tht this~d the tk4r pges a0r end ex act copy of pages 2 3 specification origlnl-j lodged 0" 'hr I 919.L 01/1 co0 0H o I/ L L-0 +il 0 os00 01/S 009 01/s 6.0* 1.i 01/0 009 2zDIW N iJs-,jl aRIMIHOA 01 aLN1lddO)Mdv ILIMI -a I v9d q, 2z(a go AJ.TZtXQ-L
VIMMJIUJMAII
T
aINldtl:JSET.1 0Od azrw aNO 7Z.IDIXOjj -"unzv DIMUfJ)lLS aJZO)aoud *0 S *55 S 0 0
S
S *0 S SO S SOS 0
L
Claims (4)
1. The N-oxide of 2,2-bis phenoxy NN-dimethyl ethylamine of the formula CH- CH- N 0 CH 3 3^ so @0 00 *4 4 I 4400 4 *r 4 *4I @440 0 4* 44 4 @0 *r 4 44
2. The acid addition salts of the N-oxide of claim 1, with a mineral or organic acid.
3. A process for producing the N-oxide of claim 1 in which a 2,2-bis phenoxy NN-dimethyl e.hylamine or an acid addition salt thereof is reacted with a mineral or organic peroxide in an inert solvent.
4. A pharmacutical compoition having as atej ingredient, a compound according toc or 2, in combination or dwi-wreith an inert non-toxic pharmaceut- j y'acept-1o carrier or vhi c 4o. Pharmaceutical compositions having as active ingredient a compound according to any of claims 1 and 2 in combination or admixture with an inert non-toxic pharmaceutically-acceptable carrier or vehicle suitable for the parenteral, oral, rectal or percutaneous ways of administration. S A method for treating depressive conditions without irducing noxious side-effects which comprises administering to humans or animals in need of such treatment a safe but effective antidepressive amount of a compound according to claim 1 or claim 2, or a composition according to claim 4 II 4 I i 44 0 0 II 4 4 I t DATED this 9th day of November, 1989. ALBERT'ROLLAND'S.A. WATERMARK PATENT TRADEMARK ATTORNEYS Queen Street, MELBOURNE. VIC. 3000. AUSTRALIA. IAS:KJS:JZ (9.37) Ai -4
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8511152 | 1985-07-22 | ||
| FR8511152 | 1985-07-22 | ||
| FR8515448A FR2588552B3 (en) | 1985-10-16 | 1985-10-16 | NOVEL OXIDE DERIVATIVE OF NN-DIMETHYL ETHYLAMINE, PROCESS FOR PREPARING THE SAME AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME |
| FR8515448 | 1985-10-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU6038586A AU6038586A (en) | 1987-01-29 |
| AU593562B2 true AU593562B2 (en) | 1990-02-15 |
Family
ID=26224627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU60385/86A Ceased AU593562B2 (en) | 1985-07-22 | 1986-07-21 | N-oxide of NN-dimethyl ethylamine, a process for its production and the pharmaceutical compositions containing it |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0216646B1 (en) |
| KR (1) | KR940011528B1 (en) |
| AU (1) | AU593562B2 (en) |
| DE (1) | DE3674873D1 (en) |
| IE (1) | IE58999B1 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2583639B3 (en) * | 1985-06-24 | 1987-09-25 | Rolland Sa A | NOVEL PHARMACEUTICAL COMPOSITIONS IMPROVING PSYCHOMOTOR PERFORMANCE AND PROCESS FOR OBTAINING SAME |
| AU592358B2 (en) * | 1985-07-22 | 1990-01-11 | Lipha | Derivatives of diphenoxyethylamine, a process for their production and the pharmaceutical compositions containing the same |
| FR2589357B3 (en) * | 1985-11-05 | 1988-01-29 | Rolland Sa A | NOVEL PHARMACEUTICAL COMPOSITIONS IMPROVING CEREBRAL OXYGENATION BASED ON DIPHENOXY DIMETHYLAMINOETHANE AND PROCESS FOR OBTAINING SAME |
| CA2014201A1 (en) * | 1989-04-26 | 1990-10-26 | Albemarle Corporation | Solid non-hygroscopic trialkylamine oxides |
| US5866718A (en) * | 1997-03-20 | 1999-02-02 | General Electric Company | Synthesis of tertiary amine oxides |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU6043686A (en) * | 1985-07-22 | 1987-01-29 | Lipha | Derivatives of diphenoxyethylamine, a process for their production and the pharmaceutical compositions containing the same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR5498M (en) * | 1966-05-18 | 1967-10-30 | ||
| DE2749214A1 (en) * | 1976-11-30 | 1978-06-01 | Upjohn Co | N- (2-AMINOCYCLOPENTYL) -N-ALKANOYLANILIDE OR THE 2-N-OXIDES THEREOF, METHOD FOR THEIR PREPARATION AND USE OF THE SAME IN THE TREATMENT OF DEPRESSIVE CONDITIONS |
-
1986
- 1986-07-21 IE IE192586A patent/IE58999B1/en not_active IP Right Cessation
- 1986-07-21 AU AU60385/86A patent/AU593562B2/en not_active Ceased
- 1986-07-22 EP EP86401630A patent/EP0216646B1/en not_active Expired - Lifetime
- 1986-07-22 DE DE8686401630T patent/DE3674873D1/en not_active Expired - Fee Related
- 1986-07-22 KR KR1019860005928A patent/KR940011528B1/en not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU6043686A (en) * | 1985-07-22 | 1987-01-29 | Lipha | Derivatives of diphenoxyethylamine, a process for their production and the pharmaceutical compositions containing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0216646A3 (en) | 1987-11-04 |
| IE58999B1 (en) | 1993-12-15 |
| EP0216646A2 (en) | 1987-04-01 |
| KR940011528B1 (en) | 1994-12-20 |
| EP0216646B1 (en) | 1990-10-10 |
| IE861925L (en) | 1987-01-22 |
| AU6038586A (en) | 1987-01-29 |
| KR870001144A (en) | 1987-03-11 |
| DE3674873D1 (en) | 1990-11-15 |
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