CS269281B1 - Method of 2-/(benzyl-anilino)/-2-imidazoline,2-(naphthyl-methyl)-2-imidazoline and 2-(tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-2-imidazoline in medicamentous forms - Google Patents
Method of 2-/(benzyl-anilino)/-2-imidazoline,2-(naphthyl-methyl)-2-imidazoline and 2-(tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-2-imidazoline in medicamentous forms Download PDFInfo
- Publication number
- CS269281B1 CS269281B1 CS883823A CS382388A CS269281B1 CS 269281 B1 CS269281 B1 CS 269281B1 CS 883823 A CS883823 A CS 883823A CS 382388 A CS382388 A CS 382388A CS 269281 B1 CS269281 B1 CS 269281B1
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- CS
- Czechoslovakia
- Prior art keywords
- imidazoline
- mobile phase
- mol
- oxymetazoline
- tert
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 8
- -1 benzyl-anilino Chemical group 0.000 title claims abstract 3
- YPQYLRODFOZPBW-UHFFFAOYSA-N 3-[1-(4,5-dihydro-1H-imidazol-2-yl)-2,2-dimethylpropyl]-2,4-dimethylphenol Chemical compound C(C)(C)(C)C(C1=C(C(=CC=C1C)O)C)C=1NCCN1 YPQYLRODFOZPBW-UHFFFAOYSA-N 0.000 title claims 2
- CNIIGCLFLJGOGP-UHFFFAOYSA-N 2-(1-naphthalenylmethyl)-4,5-dihydro-1H-imidazole Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 CNIIGCLFLJGOGP-UHFFFAOYSA-N 0.000 claims abstract description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 18
- WYWIFABBXFUGLM-UHFFFAOYSA-N oxymetazoline Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CC1=NCCN1 WYWIFABBXFUGLM-UHFFFAOYSA-N 0.000 claims abstract description 14
- REYFJDPCWQRWAA-UHFFFAOYSA-N antazoline Chemical compound N=1CCNC=1CN(C=1C=CC=CC=1)CC1=CC=CC=C1 REYFJDPCWQRWAA-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229960005016 naphazoline Drugs 0.000 claims abstract description 9
- 229960002469 antazoline Drugs 0.000 claims abstract description 8
- 229960001528 oxymetazoline Drugs 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 239000002594 sorbent Substances 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims abstract description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000004811 liquid chromatography Methods 0.000 claims abstract description 4
- 239000000741 silica gel Substances 0.000 claims abstract description 4
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 239000012153 distilled water Substances 0.000 claims description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 4
- 239000001632 sodium acetate Substances 0.000 claims description 4
- 235000017281 sodium acetate Nutrition 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 238000001514 detection method Methods 0.000 claims description 2
- 230000014759 maintenance of location Effects 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- 238000004587 chromatography analysis Methods 0.000 claims 1
- OPGYRRGJRBEUFK-UHFFFAOYSA-L disodium;diacetate Chemical compound [Na+].[Na+].CC([O-])=O.CC([O-])=O OPGYRRGJRBEUFK-UHFFFAOYSA-L 0.000 claims 1
- 238000010828 elution Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000008351 acetate buffer Substances 0.000 abstract 1
- 238000004190 ion pair chromatography Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000010812 external standard method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
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- Investigating Or Analysing Biological Materials (AREA)
Abstract
Stanovení 2-[(N-benzylanilino)- aethyl] -2-iaidazolinu, antazolinu, 2- -(1-naítylmethyl)-2-iinidazolinu, nafazolinu a 2-(tert-butyl-3-hydroxy-2,6- -diiaethyIbenzyl)-2-iaidazolinu, oxýmetazolinu ve vzorcích farmaceutických přípravků Je prováděno kapalinovou chromatografií. K separaci se používá sorbent silikagelového typu a kovalentně vázanými kyanoethylovými skupina·!. Jako mobilní fáze se používá octanový pufr ve směsi acetonitrllu s vodou. Navržená metoda je výhodná pro kvantitativní stanovení a plně nahrazuje dříve používanou iontopárovou chromatografii.Determination of 2 - [(N-benzylanilino) - ethyl] -2-iaidazoline, antazoline, 2- - (1-naphthylmethyl) -2-imidazoline, naphazoline and 2- (tert-butyl-3-hydroxy-2,6- di-diethylbenzyl) -2-iaidazoline, oxymetazoline in pharmaceutical samples of preparations is carried out by liquid chromatography. It is used for separation silica gel type sorbent and covalently bound by cyanoethyl groups. It is used as a mobile phase acetate buffer in acetonitrile with water. The proposed method is advantageous for quantitative determination and fully replaces the previously used ion-pair chromatography.
Description
1 CS 269 281 B11 EN 269 281 B1
Vynález se týká stanovení 2-[(N-benzylanilino)methyl]-2-imidazolinu, dále Jen anta-zolinu, 2-(1-naftylmethyl)-2-imidazolinu, dále Jen nafazolinu, a 2-(tert-butyl-3-hydroxy--2,6-dimethylbenzyl)-2-imidazolinu, dále Jen oxymetazolinu, zvláště ve farmaceutickýchpřípravcích, zejména v tekutých lékových formách.The present invention relates to the determination of 2 - [(N-benzylanilino) methyl] -2-imidazoline, hereinafter referred to as anaprazoline, 2- (1-naphthylmethyl) -2-imidazoline, hereinafter naphazoline, and 2- (tert-butyl-3). -hydroxy-2,6-dimethylbenzyl) -2-imidazoline, further only oxymetazoline, especially in pharmaceutical formulations, especially in liquid dosage forms.
Nejčastěji Jsou tyto látky stanovovány kolorimetricky na základě barevných reakcíimidazolových derivátů. Bohužel nelze tímto způsobem postihnout stabilitu uvedených lá-tek, protože nelze postihnout degradaění produkty, která mají zachován imidazolový ske-let. K novějším metodám stanovení antazolinu, nafazolinu a oxymetazolinu patří stanovenípomocí kapalinové chromatografie. Původně byl Jako sorbent použit , silný katex (J. A.Mollica, et al.: Anal. Chem. 45, 1859 (1973))· Další práce Již využívají reverzní sor-bent (T. R. Koziol, et al.: J. Pharm. Sci. 68, 1135 (1979)} J. Bauer, S. Krogh: J. Pharm.Sci. 72, 1347: (1983)} G. Andermann, A. Richard: J. Chromatogr. 298, 189 (1984)} G. Pugli-si, et al.: J. Chromatogr. 369, 165 (1986)} J. A. de Schutter, et al.: J. Chromatogr. 391, 303 (1987), přiěemž mobilní fáze vždy obsahuje iontopárovací složku, pufr a směs vo-dy s methanolem nebo acetonitrilem. Tyto metody poskytuji kvalitativně dobrá výsledky,ale v případě analýz vzorků, obsahujících tenzidy, Je kvantitativní reprodukovatelnostmalá vzhledem k ovlivnění tvorby iontových párů. Navíc Je celá metoda zatížena časovědlouhou přípravou chromatografických podmínek.Most commonly, these substances are determined colorimetrically on the basis of colored reaction imidazole derivatives. Unfortunately, the stability of these substances cannot be affected in this way, as degradation products that retain the imidazole skeleton cannot be affected. More recent methods for the determination of antazoline, naphazoline and oxymetazoline include liquid chromatography. Initially, a strong cation exchanger (JAMollica, et al .: Anal. Chem. 45, 1859 (1973)) was used as a sorbent. · Further Works Already used reverse sorbent (TR Koziol, et al .: J. Pharm. Sci. J. Bauer, S. Krogh, J. Pharm. Sci., 72, 1347: (1983) G. Andermann, A. Richard: J. Chromatogr., 298, 189 (1984), G. Pugliam, et al., J. Chromatogr., 369, 165 (1986); JA de Schutter, et al., J. Chromatogr., 391, 303 (1987), wherein the mobile phase always contains an ion exchange component, a buffer and a mixture in with methanol or acetonitrile, these methods provide qualitatively good results, but in the case of samples containing surfactants, it is quantitatively reproducible small in terms of affecting the formation of ion pairs.
Uvedená nevýhody odstraňuje způsob stanovení antazolinu, nafazolinu a oxymetazolinupodle vynálezu, Jehož podstata spočívá ve stanovení kapalinovou chromatografií na koloněnaplněné sorbentem silikagelového typu s kovalentně vázanými kyanoethylovými skupinamio velikosti částic 5 až 10/im metodou vnějšího standardu. Mobilní fáze Je tvořena rozto-kem octanu sodného o koncentraci 5 až 100 mol/nP a kyseliny octová o koncentraci 5 až 100mol/m^ ve směsi 40 až 85 % obj. acetonitrilu a 15 až 60 % obj. destilované vody. Průtokmobilní fáze Je v rozmezí 0,4 až 2 ml/min, přičemž Jsou všechny vzorky včetně roztokůstandardu ředěny mobilní fází.The above-mentioned disadvantages are eliminated by the method of determination of antazoline, naphazoline and oxymetazolin according to the invention, which is based on determination by liquid chromatography on a column filled with a silica gel type sorbent with covalently bonded cyanoethyl groups having a particle size of 5 to 10 .mu.m by an external standard method. The mobile phase consists of a solution of 5 to 100 mol / nP sodium acetate and 5 to 100 mol / ml acetic acid in a mixture of 40 to 85 vol% acetonitrile and 15 to 60 vol% distilled water. The mobile phase flow is in the range of 0.4 to 2 ml / min, with all samples including the standard solution being diluted with the mobile phase.
Způsob stanovení podle vynálezu Je vhodný pro svoji Jejlnoduchost, rychlost a spo-lehlivost. Umožňuje stanovení antazolinu, nafazolinu a oxymetazolinu v komplikovaných lé-kových formách, což nebylo dosavadními metodami zaručeno. V neposlední řadě navrhovanéstanoveni zrychluje a usnadňuje kontrolu léčiv, a tím do značné míry příznivě ovlivňujeekonomiku výroby. Následující příklady způsob podle vynálezu pouze dokládají, ale neomezují. Příklad 1The assay method of the invention is suitable for its smoothness, speed and reliability. It allows the determination of antazoline, naphazoline and oxymetazoline in complicated drug forms, which has not been guaranteed by the prior art. Last but not least, the proposed provision accelerates and facilitates drug control and thus largely influences production economics. The following examples illustrate, but do not limit, the process of the invention. Example 1
Chemikálie: octan sodný p. a. kyselina octová p. a.acetonitril pro UVdestilovaná voda Přístroje: kapalinový chromatograf ve spojení s počítačem integrátoremspektrofotometrický detektor kolona skleněná, 150 x 3 mm, naplněná sorbentem silikagelového typu s kova-lentně .vázanými kyanoethylovými skupinami o změní 5 jumChemicals: sodium acetate p.a. acetic acid p.a.acetonitrile for UV distilled water Apparatus: liquid chromatograph in conjunction with a computer integratorspectrophotometric detector glass column 150 x 3 mm filled with silica gel type sorbent with covalently bound cyanoethyl groups of 5 µm
Chromatografické podmínky:Chromatographic conditions:
Mobilní fáze: 60 % obj. acetonitril, 40 % obj. destilovaná voda, octan sodnýo koncentraci 20 mol/«P, kyselina octová o koncentraci 20 mol/m\Mobile phase: 60% v / v acetonitrile, 40% v / v distilled water, 20 mol / mol sodium acetate, 20 mol / m acetic acid \ t
Průtok: 0,5 ml/minFlow rate: 0.5 ml / min
Detekce: UV, 235 nm, rozsah 0,16 abs. J.Detection: UV, 235 nm, 0.16 abs range. J.
Retenční časy: nafazolin 8,1 min antazolin 10,9 min Příprava standardu: 53 mg antazolinu a 21 mg nafazolinu se rozpustilo ve 100 al mobilnífázeRetention times: naphazoline 8.1 min antazoline 10.9 min Standard preparation: 53 mg antazoline and 21 mg naphazoline were dissolved in 100 µl of mobile phase
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS883823A CS269281B1 (en) | 1988-06-03 | 1988-06-03 | Method of 2-/(benzyl-anilino)/-2-imidazoline,2-(naphthyl-methyl)-2-imidazoline and 2-(tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-2-imidazoline in medicamentous forms |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS883823A CS269281B1 (en) | 1988-06-03 | 1988-06-03 | Method of 2-/(benzyl-anilino)/-2-imidazoline,2-(naphthyl-methyl)-2-imidazoline and 2-(tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-2-imidazoline in medicamentous forms |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS382388A1 CS382388A1 (en) | 1989-09-12 |
| CS269281B1 true CS269281B1 (en) | 1990-04-11 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS883823A CS269281B1 (en) | 1988-06-03 | 1988-06-03 | Method of 2-/(benzyl-anilino)/-2-imidazoline,2-(naphthyl-methyl)-2-imidazoline and 2-(tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-2-imidazoline in medicamentous forms |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS269281B1 (en) |
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1988
- 1988-06-03 CS CS883823A patent/CS269281B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS382388A1 (en) | 1989-09-12 |
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