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
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- 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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- Australia
- Prior art keywords
- oxide
- dimethyl
- compound according
- pharmaceutical compositions
- mineral
- Prior art date
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- Ceased
Links
- 150000001204 N-oxides Chemical class 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000002253 acid Substances 0.000 claims description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 230000001430 anti-depressive effect Effects 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 239000003981 vehicle Substances 0.000 claims description 3
- 230000003001 depressive effect Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 230000001473 noxious effect Effects 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 150000001451 organic peroxides Chemical class 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 235000002639 sodium chloride Nutrition 0.000 description 7
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- IMLAIXAZMVDRGA-UHFFFAOYSA-N 2-phenoxyethanamine Chemical compound NCCOC1=CC=CC=C1 IMLAIXAZMVDRGA-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 101150058514 PTGES gene Proteins 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
- BLGXFZZNTVWLAY-CCZXDCJGSA-N Yohimbine Natural products C1=CC=C2C(CCN3C[C@@H]4CC[C@@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-CCZXDCJGSA-N 0.000 description 1
- LUTSRLYCMSCGCS-BWOMAWGNSA-N [(3s,8r,9s,10r,13s)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,16-decahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC=C3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 LUTSRLYCMSCGCS-BWOMAWGNSA-N 0.000 description 1
- 235000019401 acetone peroxide Nutrition 0.000 description 1
- 239000000011 acetone peroxide Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229920013820 alkyl cellulose Polymers 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229960004046 apomorphine Drugs 0.000 description 1
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 235000001046 cacaotero Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- QNMGHBMGNRQPNL-UHFFFAOYSA-N medifoxamine Chemical compound C=1C=CC=CC=1OC(CN(C)C)OC1=CC=CC=C1 QNMGHBMGNRQPNL-UHFFFAOYSA-N 0.000 description 1
- 229960003123 medifoxamine Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229960000317 yohimbine Drugs 0.000 description 1
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 1
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
Landscapes
- 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 |
| KR870001153A (en) * | 1985-07-22 | 1987-03-11 | 데. 롤랑 | Pharmaceutical composition containing diphenoxyethylamine derivative and its production method |
| 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 AU AU60385/86A patent/AU593562B2/en not_active Ceased
- 1986-07-21 IE IE192586A patent/IE58999B1/en not_active IP Right Cessation
- 1986-07-22 KR KR1019860005928A patent/KR940011528B1/en not_active Expired - Fee Related
- 1986-07-22 DE DE8686401630T patent/DE3674873D1/en not_active Expired - Fee Related
- 1986-07-22 EP EP86401630A patent/EP0216646B1/en not_active Expired - Lifetime
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 |
|---|---|
| IE58999B1 (en) | 1993-12-15 |
| AU6038586A (en) | 1987-01-29 |
| KR940011528B1 (en) | 1994-12-20 |
| KR870001144A (en) | 1987-03-11 |
| DE3674873D1 (en) | 1990-11-15 |
| IE861925L (en) | 1987-01-22 |
| EP0216646A3 (en) | 1987-11-04 |
| EP0216646B1 (en) | 1990-10-10 |
| EP0216646A2 (en) | 1987-04-01 |
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