BUNDESREPUBLIK DEUTSCHLAND
`
`Internat. KL:
`
`A61k
`
`DEUTSCHES
`
`PATENTAMT
`
`Deutsche Kl:
`
`30h-2/30
`
`AUSLEGESCHRIFT
`
`1182 388
`
`Nummer:
`
`1 182 388
`
`Aktenzeichen:
`
`F35258I1V a/30h
`
`Anmeldetag:
`Auslegetag:
`
`31, Oktober 1961
`26. November 1964
`
`
`
`Phenoxy-essigsdurealkylamide besttzen hypnotische
`und narketische Eigenschaften. Sie stellen insbeson-
`dere intravends anwendbare Narkotika dar, dic sich
`durch kurze Wirksamkeit und, gegeniiber den ftir
`diesen Zweck bisher ausschlicRlich verwendeten Barbi-
`tursiiurederivaten, durch einen sehr schnellen Wirkungs-
`abfall und durch das Fehlen des sogenannten »over-
`hang« auszeichnen.
`in
`Fs handelt sich um destillierbare, meist Slige,
`Wasser
`fast unlistiche Verbindungen. Von
`den
`bekannten, narkotisch wirksamen Phenoxy-essigsdure-
`amiden seien beispielsweise folgende genannt: 2-Meth-
`oxy- und 2-Athoxy-4-allylphenoxyessigsdure-N,N-di-
`dthylamid,
`2-Methoxy-4-n-propylphenoxyessigsdure-
`N,N-didthylamid,
`2-Methoxy-4-propenylphenoxy-
`essigsiure-N,N-diathylamid, 2-Athoxy-4-(1‘-hydroxy-
`n-propyl)-phenoxyessigsdure-N,N-diathylamid, 2-Ath-
`oxy - 4 - acetylphenoxyessigsaure - N, N - diiithylamid,
`2-Methoxy-4-41-*-buten-3’-onyl)-phenoxyessigsiure-
`N,N-didthylamid,
`3-Methoxy-4-N,N-difithyicarb-
`amidomethoxy-phenylessigsauredthyl-, -n-propyl- und
`-allylester, 3-Mcthoxy-4-N,N-diadthylcarbamidometh-
`oxy-benzoesiuredthyl- und -n-propyiester, 2-Methoxy-
`4 - allylphenoxyessigsiiure - N - athyl - N - dthoxyamid,
`3-Methoxy-4-(N-dthoxy- N-dthyl-carbamidomethoxy)-
`phenylessigsiure-n-propylester und -isopropylester.
`Die Herstellung waGriger, zur intravenésen Injek-
`lion geeigneter Lésungen diescr Stoffe, wie sie zur
`Anwendung als Narkotika bendétigt werden, gelingt
`nur unter Verwendung von Lésungsvermittlern, Als
`solche wurden bisher z. B. Propylenglykol, Butylen-
`glykol, Natriumsalicylat, Natriumbenzoat, Natrium-
`hippurat, Cyclohexylsalicylat, Kresotinate, wasser-
`lésliche Salze von Gallensduren, yon «-Naphthyi-
`essigsiure sowie Gemisch derartiger Salze verwendet
`(vel. deutsche Auslepeschriften 1 089 510 und 1 091 288).
`Die so hergestellten Loésungen reizen die Venenwand
`jedoch schr stark. Ein weiterer Nachteil besteht darin,
`daB der Wirkstoff beim Verdiinnen mit Wasser oder
`mit Sernm sofort in Form von Trépfchen ausgeschie-
`den wird.
`Man hat weiter versucht, an Stelle von Lésungen
`Emulsionen der genannten Phenoxyessigsdurcamide in
`Wasser anzuwenden. Derartige Emulsionen zeigen
`zwar cine pute Venenvertraglichkeit,
`ihre technische
`Herstellung ist jedoch nicht cinfach, da an eine intra-
`venGse injizierbare Emulsion sehr hohe Anforderungen
`in bezug auf die Haltbarkeit gestellt werden. Dic
`Emulsion muf sterilisierbar sein, und der Durchmesser
`der gréB8ten enthaltenen Teilechen darf nicht ttber 5 u
`liegen. Auch wahrend der gesamten Lagerzett darf
`diese TeifchengréBe nicht tiberschritten werden, da bei
`
`Verfahren zur Herstellung von sterilisierbaren
`waBrigen Lésungen von narkotisch wirkenden
`Phenoxyessigsdureamiden
`
`
`
`Anmelder:
`
`ia
`
`Farbenfabnken Bayer Aktiengesellschaft,
`Leverkusen
`
`
`Als Exfinder benannt:
`Dr. Werner Scholtan, Kd6ln-Stammhetm
`
`--
`
`2
`
`a0
`
`a5
`
`30
`
`Do on
`
`40
`
`45
`
`5a
`
`Injektion cine durch griBere Teilchen hervor-
`der
`gerufene Verstopfung der feinen Arteriolen zu Ol-
`embolien fithren kann.
`Es wurde nun gefunden, dafi man sterilisierbare,
`waBrige Lasungen von narkotisch wirkenden Phenoxy-
`essigsdureamiden, besonders 2-Methoxy-4-allylphen-
`oxyessigsdure-N,N-didthylamid, 3-Mcthoxy-4-N,N-di-
`Athylcarbamidomethoxy- phenylessigsiure - n - propyl-
`ester
`und
`2-Methoxy-4-allylphenoxyessigsdure-
`N-athyl-N-dthoxyamid, herstellen kann, wenn man
`als Lisungsvermittier oxydthyliertes Ricinusd! ver-
`wendet.
`Man erhalt solche Lésungen, wenn man den Wirk-
`stof mit der zwei- bis achtfachen Menge yon oxy-
`dthyliertem Ricinusdél vermischt und die Mischung
`anschlieBend mit Wasser verdiinnt oder wenn man den
`Wirkstoff in der konzentrierten Lésung des genannien
`Lésungsvermitilers auflést und die Lésung dann mit
`Wasser verdiinnt. Diese Ldsungen sind klar, sterilisier-
`bar und lassen sich mit Wasser in jedem Verhaltnis
`mischen. Sie zeigen bei intravendser Injektion eine sehr
`gute Venenvertréglichkeit. Zur Erhéhung der Léslich-
`keit k6nnen zusdtzlich noch andere bekannte J.dsunogs-
`yermittler verwendet werden.
`Die erfindungsgemd4f hergestellten Lésungen sind
`denen, die nach den obengenannten deutschen Aus-
`legeschriften
`1089510 und
`1091 288
`hergestellt
`werden, beziiglich allgemciner und Grtlicher Vertrag-
`lichkeit um ein Mehrlaches tiberlegen,
`
`;
`i
`Beispicl
` 2-Methoxy-4-allylphenoxyessigsiure-N,N-di-
`5 g
`dthylamid werden mit 20 g oxydthyliertem Ricinusél
`vermischt und die Lésung mit Wasser auf 100 com
`aufgefiilit.
`
`409 729/380
`
`

`

`1182 388
`
`3
`
`4
`
`Beispiel 6
`
`Beispiel 2
`2-Methoxy-4-allylphenoxyessigsdure-N,N-di-
`3 g
`athylamid werden mit 10 g oxythyliertem Ricinusél
`vermischt und die Lésung mit Wasser auf 100 ccm
`aufgeftillt.
`
`Beispicl 3
`3-Methoxy-4-N,N-didthylearbamidomethoxy-
`§ @
`phenylessigsiure-n-propylester werden mit 20 g oxy-
`thyliertem Ricinusii! vermischt und die Lésung mit
`Wasser auf 100 ccm aufgeftillt. Eine Steigerung der
`Wirkstoffkonzentration auf 8,3°/,
`ist méglich, wenn
`man den Emulgatorgehalt auf 254/, heraufsetzt.
`
`Beispiel 4
`
`3-Methoxy-4-N,N-diiithylcarbamidomethoxy-
`3 g
`phenylessigsdure-n-propylester werden mit 10 g oxy-
`dthyliertem Ricinusél vermischt und die Lésung mit
`Wasser auf 100 ecm aufgefilllt.
`
`Beispiel
`
`4
`
`2-Methoxy-4-allylphenoxyessigsdure-N-athyl-
`5 g
`N-athoxyamid werden mit 20 g oxydthyliertem Ricinus-
`él vermischt und die LOsung mit Wasser anf 100 com
`aufgeftillt.
`
` 3-Methoxy-4-[N-dthoxy-N-dthyl-carbamido-
`4 g
`methoxy}-phenylessigsdure-n-propylester werden mit
`20 g oxyathyliertem Ricinusél vermischt. Die erhaltene
`Lésung wird mit destilliertem Wasser auf 100 ml auf-
`pefiilit.
`
`7
`Beispie!l
` 3-Methoxy-4-[N-dthoxy-N-dthyl-carbamido-
`4 g
`methoxy]-phenylessigsdure-i-propylester werden mit
`20 g oxyathyliertem Ricinusél vermischt. Die erhaltene
`Lésung wird mit destilliertem Wasser aef 100 ml auf-
`gefiillt.
`
`Patentanspruch:
`Verfahren zur Herstellung von sterilisierbaren
`wibrigen Lésungen von narkotisch wirkenden
`Phenoxyessigsiurcamiden, besonders 2-Mcthoxy-
`4allylphenoxyessigsiure-N, N-didthylamid, 3-Meth-
`oxy-4-N, N-didthylcarbamidomethoxy-phenylessig-
`sdure-n-propylester und
`2-Methoxy-4-allylphen-
`oxyessigsiure-N-dthyl-N-dthoxyamid, dadurch
`gekennzeichnet, daf man als Lésungs-
`vermitiler oxyathyliertes Ricinusdl verwendet.
`
`In Betracht gezogene Drucksehriften:
`Deutsche Auslegeschriften Nr.
`1 091 288,
`1 O89 510.
`
`1o
`
`15
`
`20
`
`45
`
`499 729/380 14.64 3 Bundesdruckerei Berlin
`
`

`

`Pe Ta
`= i
`a a rd
`
`RESEAV:
`PATENT
`SPECIFICATION
`NO DRAWINGS
`
`
`
`94 L694
`Date of Application and filing Complete Specification Oct. 9, (962.
`No, 3820662.
`Application made in Germany (No. 35258 I¥a/30h) on Get.3! , 1961,
`Complete Specification Published Nov. 13, 1963,
`1963,
`© Crown Copyright
`
`Index at acceptance; —Class A5 B(2H, 21, 2N, 2S}
`International Classification: —A 61 k.
`
`COMPLETE SPECIFICATION
`Stable Solutions of Narcotically-active Phenoxyacetic Acid
`Amides
`
`SPECIFICATION NO, 941,994
`
`the Inventor of this invention in the sense of being the actual deviser therenf
`within the meaning of Section 14 of the Patents Act, 1949 ts Werner Scholten,
`Friedricn~Ebert-Strasse £292, Wuppertal-Elberfeld, Germany, of German nationality.
`THE PATENT OFFICE
`
`D 29903/1(8) /R. 109 200 40/85 PL
`
`15
`
`20
`
`25
`
`30
`
`Measaane roe uy
`AANFAMARTLALINTAR LRS OPP RA UALR UL
`:
`stituted phenoxyacetic acid amides,
`of gallic acid and of snaphthylacetic acid,
`possess
`Aryloxyacetic
`acid
`alkylamides
`as well as mixtures of salts of
`these types,
`hypnotic and narcotic properties. They arc,
`Hicwever,
`the
`solutions so
`produced con-
`in particular,
`intravenously administratable
`siderably irritate the venous walls.
`A further
`narcotics which are charactzrised by a short
`disadvantage is that the active material, upon
`period af effectiveness and,
`im comparison
`dilution with water or with scrium,
`immedi-
`with the barbituric acid derivatives previously
`ately scparates out
`in the form of droplets.
`exclusively used for
`this purpose, by a very
`Further attempts have been made io use,
`rapid decrease in effectiveness and by the
`instead of solutions, emulsions of the men-
`iack of the so-called “hangover”.
`toned aryloxyacetic acid amides
`in water.
`These alkylamides are distitiable, mostly
`Emulsions of
`this
`type admitiedly show a
`oily compounds which are aimost
`insoluble
`geod venous compatibility but their technical
`in water. Of the known, narcotically-effective
`production is, however, not simple since very
`aryloxyacetic acid amides, there may be men-
`high requirements with regard to stability are
`tioned, far example, 2-methoxy- and 2-ethoxy-
`placed on on intravenously injectable emulsion,
`4allgl-phenoxyacetic acid-N,N-diethylamide,
`The emulsion must be steriliscble and the
`2 - methoxy - 4 - 2 - propyl - phenoxyacttic
`diameter of
`the largest articles contained
`acid - N,N - diethylamide,
`2 - methoxy -
`therein must not
`fie above 4 ». During
`4 - propenyl - phenoxyacetic acid - N,N -
`the whole storage period,
`this particle size
`diethylamide, 2 - ethoxy - 4 - CP - hydroxy -
`must not be exceeded since, upon injection,
`n_- propyl) - phenoxyzeetic
`acid - N,N -
`a stoppage of the fine arterioles brought about
`diethylamide, 2-ethoxy-4-aceryl-phenoxyaceticL
`by larger particles can lead to oi! embolisms,
`We have now found that
`the use of well
`acid-N,N-diethylamide,
`2-methoxy-4-(Al-
`75
`water-soluble,
`non-ionic,
`surface - active
`
`buten - 3! - onyl} - phenoxyacetic—acid-
`materials, such as saccharose esters or ethylene
`N.N ~ diethyl - amide,
`3 - methoxy - 4-
`oxide derivatives of fatty acids, fatty alcohols,
`ENLN - diethylcarbamayl - methoxy} ~ phenyl-
`fatty oils or fatty acid esters of sorbitan, as
`solubilisers
`lead to generally well
`tolerated
`acetic
`acid
`ethyl,
`m ~ propyl
`and
`allyl
`esters,
`3 - methoxy -
`4 - (N,N - di-
`aqueous
`solutions
`of
`the
`mentioned
`wrice 43. 6d.]
`
`60
`
`vit)
`
`80
`
`

`

`PATENT
`
`SPECIFICATION
`NO DRAWINGS
`
`
`
`941.694
`Date of Application and filing Complete Specification Oct. ?, $962,
`No, 38266/62.
`Application nade in Germany (No. F35258 [¥a/30h) on Oct.3! , 1961.
`Complete Specification Published Nov, 13, 1963,
`(©) Crown Copyright 1963,
`
`Index at acceptance: —Class A5 B(2H, 21, 2N, 28)
`International Classification :—A. 61 k.
`
`COMPLETE SPECTFICA TION
`
`Stable Solutions of Narcotically-active Phenoxyacetic Acid
`Amides
`
`BayER AKTIEN-
`FARBENFARRIKEN
`We,
`GESELLSCHAFT, a bady corporate organised
`under the laws of Germany, af (22c}, Lever-
`kusen-Bayerwerk, Germany, do hereby declare
`the invention,
`for which we pray that
`a
`patent may be granted te us, and the method
`by which it is ta be performed, 10 be particu-
`larly described in and by the following state-
`ment: —
`
`invention 1s concerned with
`The present
`of narcotically-active,
`sub-
`stable
`solutions
`stituted phenoxyacetic acid amides.
`possess
`Aryloxyacetic
`acid
`alkylamides
`hypnotic and narcotic propertics. They are,
`i particular,
`intravenously administrarable
`narcotics which are characterised by a short
`period of cifectiveness and, m comparison
`with the barbituric acid dertvauves previously
`exclusively used for this purpusc, by a very
`rapid decrease i cffcctiveness and by the
`iack of
`the so-called “hangover”.
`These alkylamides are disifiahle, mostly
`oily compounds which are aumost
`insoluble
`in water. Of the known, narcorically-effective
`aryloxyacetic acid amides, there may be mer-
`tioned, for example, 2-methexy- and 2-cthoxy-
`4-2ilyl-phenoxyacctic
`acid-N,N-diethylamide,
`2 — methoxy - 4 - x» - propyl - phenoxyacttic
`acid - N,N - diethylamide,
`2 - merhoxy -
`4 - propenyl
`- phencxyaectic acid - NUN -
`diethylamide, 2 - ethoxy - 4 - (1' - hydroxy -
`a ~ propyl) - phenoxyacetic
`acid - N,N -
`diethylamide, 2-ethexy-4-acetyl-phenoxyacctic
`
`10
`
`i5
`
`20
`
`25
`
`30
`
`acid
`ethyl - carbamoyl - methoxy} - benzoic
`ethyl and x#-propyl esters and 2-methoxy-
`4 - allyl - phenoxyacetic
`acid - N - ethyl-
`N - ethoxyamide.
`of
`solutions
`The production of aqusous
`intravenous
`these
`compounds,
`suitable for
`injection as narcotics,
`is only successful with
`the use of solubilisers. Ag such,
`there were
`previously used, for example, propylene glycol,
`butylene glycol,
`sadium salicylate,
`sodium
`benzonte,
`sodium hippurate,
`cyclohexyl
`salicylate, homosalicylates, water-soluble salts
`of gailic acid and of +naphthylacetic acid,
`as well as mixtures of salts of these types,
`Hewever.
`the
`selutions so
`produced con-
`riderably irritate the venous walls, A further
`disadvantage is that the active material, upon
`dilution with water or with scrium, immedi-
`ately separatcs out
`in the form of droplets.
`Further sttempis have becn made tw use,
`insttad of solutions, emulsions of
`the men-
`uoned arylexyacetic acid amides
`in water.
`Emulsions of
`this
`type admittedly shew a
`good venous conmpatibility but their technical
`production 1s, however, not simple since very
`high requirements with regard te stability are
`placed on un intravenouslyinjectable emulsion,
`The emulsion must be sterilisable and the
`diarnetee of
`the largest particles contained
`therein must not He above 5 4. During
`the whole storage period,
`this particle size
`must not he exceeded since, upon injection,
`a stoppage of the fae artericles brought abont
`by larger particles can lead to vil embolisms.
`We have now found that
`the use of well
`75
`2-methoxy-4-(Al
`acid-N,N-diethylamide,
`water-soluble,
`non-ionic,
`surface - active
`35
`
`bute - - phenoxyacetic—acid-3° - onyl)
`
`
`materials, cuch ag saccharose esters or ethylene
`NN - diethyl
`- amide,
`3 - methoxy - 4
`oxide derivatives of fatty acids, fatty alcohols,
`(N.N - diethykcarbamayl - methoxy} - phenyl
`fatty oils or fatty acid esters of sorbitan, as
`solubilisers
`lead to generally well
`tolerared
`acetic
`acid
`ethyl,
`on
`- propyl
`and
`allyl
`esters,
`3 - methoxy -
`4 - (N,N ~ di-
`aqueous
`solutions
`of
`the
`mentioned
`
`40
`
`50
`
`55
`
`60
`
`65
`
`70
`
`80
`
`wPrice 4s. 6d]
`
`

`

`947,694 2
`
`phor” EL and the soluticn made up to 103
`ce. with water, An increase of the concentra-
`tion ol ective material to $3".
`is possible if
`the emulsifier content is increased to 25".
`
`60
`
`acid
`aryloxyacetic
`narcotically - effective
`amides, suitable for intravenous injection.
`Such solutions arc obtained when the active
`material
`ig mixed with preferably two to
`cight
`times the amount af a suriace-active
`EXAMPLE 8
`material as defined above und the mixture
`65
`3 = methoxy - 4 - (NN - diethyl-
`gs.
`4
`subsequenily diluted with water or, when
`
`the active material carbamoyl - methoxy, - vhenvlacetic—acidis dissolved in a concen-
`
`trated aqueous solution of the solubiliser, the
`#-prepyl ester are mixed with 10 ¢. oleyl
`solution is then dikited with water.
`These
`pslyelycol ether and the selutien made up to
`cohitions are cleur,
`sterilisable and can be
`100 cc. with water.
`mixed with water in any ratio. Upan intra-
`veneus injection,
`they
`show a
`very gusd
`venous compatibility.
`For increasing the
`solubility, other known solubilisers can also
`be used.
`The following Examples ate given, for the
`purporz of
`illustrating the present
`inven-
`tion: —
`
`70
`
`73
`
`80
`
`85
`
`90
`
`93
`
`5
`
`10
`
`15
`
`EXAMPLE 9
`3 - methoxy - 4 - (N.N - diethyl-
`=,
`5
`carbamoyl ~ methoxy; - phenylacetic
`acid
`w-prepyl ester arc mixed with 20 g. poly-
`ethylene oxide sorbitan <nonooteaie and the
`solution made up to 100 cc. with water.
`
`20
`
`95
`
`EXAMPLE 1
`2.~ methoxy ~ 4 - allyl - phenoxy-
`g,
`§
`acctic acid- NJN - diethylamide ar2 mixed
`with 20 g. “Cremophor” EL.
`fethoxylated
`castor oil) and the solution inade up te 100
`«cc. with water.
`(Cremophor™ is a Registered
`Trade Mark).
`
`EXAMPLH 10
`3 - methoxy - 4 - ON.N - diethyl-
`8,
`2.5
`carbamoyl! - methoxy,
`- phenylacetic
`acid
`a-prepyl ester are dissmlved in 10 g. of a
`40°..
`aqueous polyhydrosyethylene
`stearate
`solution and the solution subeegnently made
`up to 100 cc. with water.
`
`EXAMPLE 2
`4g. 2+ methoxy - 4 - allyl - phenoxy-
`acetic
`acid - NN - diethylamide are mixed
`30 with 10 ¢. oleyl polyelycol cther and the
`solution made up to 100 ce. with water.
`
`g,
`
`EXAMPLE 3
`2 - methoxy - 4 - allyl - phenoxy-
`5
`acid - ‘N,N - diethylamide are mixed
`acetic
`35 with 20 g. polyethylene oxide surbitan mono-
`oleate and the solution made up toe 100 cc.
`with water.
`
`40
`
`EXAMPLE 4
`g. 2- methoxy - 4 - ailyl - phenoxy-
`2.5
`acetic acid - N,N - diethylamide are dis-
`solved in 10 g. of a 40%,
`aqueous poly-
`hydroxyethylene
`stearate
`solution and the
`solution subsequently made up to 100 cc.
`with water.
`
`ExaMPLe 11
`3 - methoxy - 4 - OX.N - diethyl-
`g.
`2.5
`- methoxy) - phenylaceric
`acid
`carbamoyl
`#-propyl ester are dissolved in 10 g. of a
`AQ) agucaus saccharose monolaurate solu-
`tion and the solution subsequently made up
`ta 100 cc, with water.
`
`EXAMPLE 12
`3 - methoxy - 4 - “NIN - diethyl-
`3g.
`- methoxy;
`- phenylacetic
`acid
`carbamoyl!
`#-propyl ester are mixed with 10 g. “Cremo-
`phor” EL and the solution made up to 100
`ec. with water,
`
`EXAMPLE 13
`2 - methoxy - 4 - alfyl - phenoxy-
`Sg.
`acid - N - ethyl - N
` ethoxyamide
`acetic
`sie mixed with 20 g. “Cramaphor™ EL and
`the solution made up to 160 c.. with water.
`
`100
`
`WHAT WE CLAIM I8:—
`a nar-
`1. Statle,
`aqueous
`solutians of
` cctically-active, substituted phenoxyacctic acid
`amide
`suitable
`for
`intravenous
`injection,
`characterised by a content of a water-soluble,
`non-ionic, surface-active material.
`2. Solutions according to claim 1, wherein
`the surface-active material
`is
`a
`saccharose
`ester or an ethylene oxide derivative of a
`fatty acid,
`a
`fatty alcohol, a fatiy cil or a
`fatty acid ester of sorbitan.
`3. Seluiions according io claim 2, wherein
`the surface-active material
`is an ethoxylated
`castor oil, oleyl polygiycol ether. polyethylene
`EXAMPLE 7
`
`
`
`
`5g. 3-methoxy 4-(N,N - diethyl sorbitan=monooleate,oxide polyhydrexy- 115
`ethylene stearzte or saccharase imoncolaurate.
`carbamoyl - methoxy; - phenylacctic
`acid
`4, Solutions eceerding to any of the pre-
`#-propyl ester are mixed with 20 gs. “Cremo-
`
`45
`
`50
`
`55
`
`TixaMPin 5
`g, 2- methoxy - 4 - alist - phenoxy-
`2.5
`acid - N,N - diethylamide
`are
`dis-
`acetic
`colved in 10 g. of a 409% aqueous saccharose
`monolaurate solution and the sofutien sub-
`sequently made up to 100 ce. with water,
`
`EXAMPLE 6
`g. 2- methoxy - 4 ~ allyl ~ phenoxy-
`3
`acid - N,N - diethylamide
`are mixed
`acetic
`with 10 s. “Cremophor” EL and the solu-
`tion made up to 100 cc. with water.
`
`105
`
`110
`
`
`
`

`

`
`
`941,694 3
`
`
`
`7. Frecess for the production of solutions
`2-
`is
`amide
`ihe
`claims, wherein
`ceding
`according to claim 1, whercin the amide is
`acid-
`racthoxy - 4 - allyl - phenoxy - acetic
`NUN
`- diethyfamide,
`3
`-
`racthoxy - 4 dissolved in a concentrated ugucous solution
`(NUN - diethyl
`-
`carbamoyl
`- methoxy;
`of
`the surface-active matecial and the solu-
`lion chtained diluted with water.
`phenyl - acetic
`acid
`# - propyl
`ester
`or
`2 - methoxy - 4 - allyl - phenoxyacetic
`acid-
`8. Solutions according to claim 1, when-
`WN = ellyl - N - ethoxyamide.
`ever prepared by the process according to
`claim 6 or 7,
`5. Stable, aqueous solutions of a phenoxy-
`acelic acid amide accerding to claim 1, sub-
`stantially as hereinbefore described and with
`reference to any of the specific Examples.
`6. Process for the production of solutions
`according ta claim 1, wherein the amide js
`mixed with two to eight
`time.
`the amount
`of
`the surface-uctive material and the mix-
`ture then diluted with water.
`
`For the Applicants:
`CARPMAELS & RANSFORD,
`Chartered Patent Agents,
`24, Sourhampton Buildmegs,
`Chancery Lane,
`London, W.C.2.
`
`10
`
`i5
`
`20
`
`Leamington Spa: Printed fer Her Majesty's Stationery Office by the Courier Press.—1963.
`Published at The Patent Office, 25, Southampton Buildings, London, W.C.2, from which coptcs may be obtained.
`
`