SK284216B6 - Substituted 4-oxo-4H-1-benzopyran-2-carboxylic acid amides as ACAT inhibitors and method for their preparation - Google Patents
Substituted 4-oxo-4H-1-benzopyran-2-carboxylic acid amides as ACAT inhibitors and method for their preparation Download PDFInfo
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Abstract
Description
Vynález sa týka nových substituovaných amidov kyseliny 4-oxo-4H-l-benzopyrán-2-karboxylovej všeobecného vzorca (I), kde R1 a R2 je alkyl, resp. aryl, spôsobu ich prípravy, ako aj použitia týchto zlúčenín na inhibíciu esterifikácie a absorpcie cholesterolu pri hypercholesterolémii.The present invention relates to novel substituted 4-oxo-4H-1-benzopyran-2-carboxylic acid amides of formula (I) wherein R 1 and R 2 are alkyl, respectively. aryl, a process for their preparation, as well as the use of these compounds to inhibit esterification and cholesterol absorption in hypercholesterolemia.
(I)(I)
Doterajší stav technikyBACKGROUND OF THE INVENTION
V literatúre neboli opísané zhodné zlúčeniny. Vo všeobecnosti je príprave amidov karboxylových kyselin venovaná veľká pozornosť, pre prehľadnosť spomenieme dva zdroje, z ktorých sme čerpali informácie o spôsoboch prípravy amidov karboxylových kyselín, S. Patai: The chemistry of amides, edit. J. Žabičky, Interscience publishers, John Wiley & Sons (1970), D. Dopp, H. Dopp, Carbonsäure-amide und deren N-Derivate in Carbonsäuren and Carbonsäuren- Deriváte, edit. Houben-Weyl Methoden der organischen Chemie str. 934-1197, E5/Teil 2, Georg Thieme Verlag (1985).No matching compounds have been described in the literature. In general, the preparation of carboxylic acid amides is given great attention, for the sake of clarity, we will mention two sources from which we have drawn information on methods for the preparation of carboxylic acid amides, S. Patai: The chemistry of amides, edit. J. Žabičky, Interscience Publishers, John Wiley & Sons (1970), D. Dopp, H. Dopp, Carbons-amide and Derivatives of N-Derivate in Carbons-and-Carbons-Derivatives, edit. Houben-Weyl Methoden der Organischen Chemie p. 934-1197, E5 / Teil 2, Georg Thieme Verlag (1985).
Podstata vynálezuSUMMARY OF THE INVENTION
Nové substituované amidy kyseliny 4-oxo-4H-l-benzopyrán-2-karboxylovej všeobecného vzorca (I),The novel substituted 4-oxo-4H-1-benzopyran-2-carboxylic acid amides of formula (I),
kde R1 a R2 je: oktyl a vodík, nonyl a vodík, decyl a vodík, undecyl a vodík, dodecyl a vodík, tridecyl a vodík, tetradecyl a vodík, hexadecyl a vodík, oktadecyl a vodík, 4-aminobutyl a vodík, 3-(N,N-dimetylamino)-2,2-dimetylprop-l-yl a vodík, (3-aminocyklohexyl)-prop-l-yl a vodík, 2-((4-amino-4-metyl)-cyklohexyl)-prop-2-yl a vodík, cykloheptyl a vodík, cyklooktyl a vodík, (3R)-hexahydro-2H-azepin-2-one-3-yl a vodík, (3S)-hexahydro-2H-azepin-2-one-3-yl a vodík, 1 -adamantyl a vodík, hexametyléniminyl a vodík, 1 -metylprop-2-yl a l-metylprop-2-yl, 2-metylprop-l-yl a 2-metylprop-l-yl, pentyl a pentyl, hexyl a hexyl, oktyl a oktyl, decyl a decyl, oktyl a 2,2-dimetylundecyl-l-yl, 1-metyletyl a 2-metylprop-2-yl, cyklohexyl a 1-metyletyl, cyklohexyl a 2-metylprop-2-yl, cyklohexyl a cyklohexyl, trifenylmetyl a vodík, (l,3-benzodioxol-5-yl)-methyl a vodík, benzyl a benzyl, 2,4-dimetoxybenzyl a 2,4-dimetoxybenzyl, cyklohexyl a fenyl, (4-cyklohexyl)fenyl a vodík, 2,4-dichlórfenyl a vodík, 2,6-dichlórfenyl a vodík, 2,4-difluórfenyl a vodík, 2,6-difluórfenyl a vodík, 2,6-dimetylfenyl a vodík, 2-trifluórmetylfenyl a vodík, 4-trifluórmetylfenyl a vodík, 2,6-di-(l-metyletyl)fenyl a vodík, 2,5wherein R 1 and R 2 are: octyl and hydrogen, nonyl and hydrogen, decyl and hydrogen, undecyl and hydrogen, dodecyl and hydrogen, tridecyl and hydrogen, tetradecyl and hydrogen, hexadecyl and hydrogen, octadecyl and hydrogen, 4-aminobutyl and hydrogen, 3- (N, N-dimethylamino) -2,2-dimethylprop-1-yl and hydrogen, (3-aminocyclohexyl) -prop-1-yl and hydrogen, 2 - ((4-amino-4-methyl) -cyclohexyl) -prop-2-yl and hydrogen, cycloheptyl and hydrogen, cyclooctyl and hydrogen, (3R) -hexahydro-2H-azepin-2-one-3-yl and hydrogen, (3S) -hexahydro-2H-azepin-2- one-3-yl and hydrogen, 1-adamantyl and hydrogen, hexamethyleniminyl and hydrogen, 1-methylprop-2-yl and 1-methylprop-2-yl, 2-methylprop-1-yl and 2-methylprop-1-yl, pentyl and pentyl, hexyl and hexyl, octyl and octyl, decyl and decyl, octyl and 2,2-dimethylundecyl-1-yl, 1-methylethyl and 2-methylprop-2-yl, cyclohexyl and 1-methylethyl, cyclohexyl and 2- methylprop-2-yl, cyclohexyl and cyclohexyl, triphenylmethyl and hydrogen, (1,3-benzodioxol-5-yl) -methyl and hydrogen, benzyl and benzyl, 2,4-dimethoxybenzyl and 2,4-dimethoxybenzyl, cyclohexyl and phenyl, (4-cyclohexyl) phenyl and hydrogen, 2,4-dic chlorophenyl and hydrogen, 2,6-dichlorophenyl and hydrogen, 2,4-difluorophenyl and hydrogen, 2,6-difluorophenyl and hydrogen, 2,6-dimethylphenyl and hydrogen, 2-trifluoromethylphenyl and hydrogen, 4-trifluoromethylphenyl and hydrogen, 2, 6-di- (1-methylethyl) phenyl and hydrogen, 2.5
-di-(2-metylprop-2-yl)fenyl a vodík, 2-fenyl-fen-l-yl a vodík, 2,4,6-trimetoxyfenyl a vodík, 2,4,6-tri-(2-metylprop-2-yl)-fenyl a vodík, 2-pyridyl a vodík, 3-pyridyl a vodík, 4-pyridyl a vodík, 1-naftyl a vodík, 2-naftyl a vodík, 4'-nitro-4-fenoxy-fenyl a vodík, 4'-amino-4-fenoxy-fenyl a vodík, fenyl a fenyl.-di- (2-methylprop-2-yl) phenyl and hydrogen, 2-phenyl-phen-1-yl and hydrogen, 2,4,6-trimethoxyphenyl and hydrogen, 2,4,6-tri- (2-methylprop -2-yl) -phenyl and hydrogen, 2-pyridyl and hydrogen, 3-pyridyl and hydrogen, 4-pyridyl and hydrogen, 1-naphthyl and hydrogen, 2-naphthyl and hydrogen, 4'-nitro-4-phenoxy-phenyl and hydrogen, 4'-amino-4-phenoxyphenyl and hydrogen, phenyl and phenyl.
Vynález ďalej rieši spôsob prípravy týchto amidov, ktorého podstata je v tom, že na kyselinu 4-oxo-4H-l-benzopyrán-2-karboxylovú sa pôsobí tionylchloridom a pripraví sa chlorid, ktorý reakciou s rôznymi amínmi poskytne amidy, ktoré majú inhibičný účinok na enzým acyl-koenzým A: cholesterol acyltransferázu (ACAT).The invention further provides a process for the preparation of these amides, which comprises treating 4-oxo-4H-1-benzopyran-2-carboxylic acid with thionyl chloride and preparing a chloride which, by reaction with various amines, provides amides which have an inhibitory effect. to the enzyme acyl-coenzyme A: cholesterol acyltransferase (ACAT).
Bližšie je celý postup objasnený na príkladoch uskutočnenia.The process is illustrated in more detail by way of examples.
Príklady uskutočnenia vynálezuDETAILED DESCRIPTION OF THE INVENTION
Príklad 1Example 1
N-Oktyl-4-oxo-4H-1 -benzopyrán-2-karboxamidN-octyl-4-oxo-4H-1-benzopyran-2-carboxamide
Kyselina 4-oxo-4H-1 -benzopyrán-2-karboxylová (1,90 g, 0,01mol), sa mieša v tionylchloride (25 ml) s prídavkom kvapky dimetylformamidu ako katalyzátora, cez noc. Potom sa reakčná zmes zahustí do sucha, a následne rozpustí v 25 ml bezvodého dietyléteru. K takto vzniknutému roztoku sa prikvapká zmes oktylamínu (2,50 ml, 0,015 mol) a trietylamínu(2,10 ml, 0,015 mol) pri teplote 0 až 5 °C. Reakčná zmes sa potom zohrieva pod refluxom 2 hodiny. Potom sa reakčná zmes zahustí a produkt sa získa chromatografiou na stĺpci silikagélu s eluentom zmesou etylacetát a hexán.4-Oxo-4H-1-benzopyran-2-carboxylic acid (1.90 g, 0.01mol) was stirred in thionyl chloride (25 mL) with the addition of a drop of dimethylformamide catalyst overnight. The reaction mixture was then concentrated to dryness and subsequently dissolved in 25 ml of anhydrous diethyl ether. A solution of octylamine (2.50 mL, 0.015 mol) and triethylamine (2.10 mL, 0.015 mol) was added dropwise at 0-5 ° C. The reaction mixture was then heated under reflux for 2 hours. Thereafter, the reaction mixture was concentrated and the product was obtained by chromatography on a silica gel column eluting with a mixture of ethyl acetate and hexane.
‘H-NMR (CDClj): 0,90 (t, 3H, CH3); 1,06-1,41 (m, 10H, 5xCH2); 1,54-1,70 (m, 2H, CH2); 3,53 (q, 2H, CH2); 7,18 (s, IH, H-3); 7,26-7,60 (m, 2H, H-arom.); 7,76- 7,85 (m, IH, H-arom.); 8,17-8,24 (m, IH, H-arom.). 13C-NMR (CDClj): 14,14 (CH3); 22,54, 26,87, 29,27, 29,45, 31,79, 40,12(CH2); 112,11 (C-3); 117,85, 125,91, 126,16, 134,50(CH-arom.); 124,35, 154,76, 155.67 (C-arom.);1 H-NMR (CDCl 3): 0.90 (t, 3H, CH 3 ); 1.06 to 1.41 (m, 10 H, 5xCH 2); 1.54-1.70 (m, 2H, CH2); 3.53 (q, 2H, CH2); 7.18 (s, 1H, H-3); 7.26-7.60 (m, 2H, H-arom.); 7.76-7.85 (m, 1H, H-arom.); 8.17-8.24 (m, 1H, H-arom.). 13 C-NMR (CDCl 3): 14.14 (CH 3 ); 22.54, 26.87, 29.27, 29.45, 31.79, 40.12 (CH2); 112.11 (C-3); 117.85, 125.91, 126.16, 134.50 (CH-arom.); 124.35, 154.76, 155.67 (C-arom.);
159,21 (C=O); 178,18 (C=O).159.21 (C = O); 178.18 (C = O).
Výťažok: 69 %. T. t.: 93-96 °C.Yield: 69%. Mp: 93-96 ° C.
Príklad 2Example 2
N-N onyl-4-oxo-4H-1 -benzopyrán-2-karboxamidN-N-yl-4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z nonylamínu.It was prepared in a manner analogous to Example 1 from nonylamine.
‘H-NMR (CDClj): 0,89 (t, 3H, CH3); 1,08-1,40 (m, 12H, 6xCH2); 1,58-1,72 (m, 2H, CH2); 3,48 (q, 2H, CH2); 7,15 (s, IH, H-3); 7,20-7,52 (m, 2H, H-arom.); 7,71- 7,80 (m, IH, H-arom.); 8,19-8,25 (m, IH, H-arom.). 13C-NMR (CDClj): 14,11 (CH3); 22,56, 26,89, 29,35, 29,44, 31,85, 40,12 (CH2); 112,07 (C-3); 117,86, 125,93, 126,14, 134,46 (CH-arom.); 124,34, 154,81, 155,26 (C-arom.); 159,18 (C=O); 178,09 (C=O).1 H-NMR (CDCl 3): 0.89 (t, 3H, CH 3 ); 1.08-1.40 (m, 12 H, 6xCH 2); 1.58-1.72 (m, 2H, CH2); 3.48 (q, 2H, CH2); 7.15 (s, 1H, H-3); 7.20-7.52 (m, 2H, H-arom.); 7.71-7.80 (m, 1H, H-arom.); 8.19-8.25 (m, 1H, H-arom.). 13 C-NMR (CDCl 3): 14.11 (CH 3 ); 22.56, 26.89, 29.35, 29.44, 31.85, 40.12 (CH2); 112.07 (C-3); 117.86, 125.93, 126.14, 134.46 (CH-aromatics); 124.34, 154.81, 155.26 (C-arom.); 159.18 (C = O); 178.09 (C = O).
Výťažok: 65 %. T. t.: 101-104 °C.Yield: 65%. Mp: 101-104 ° C.
Príklad 3Example 3
Bol pripravený analogickým postupom ako v príklade 1 z decylamínu.It was prepared in a manner analogous to Example 1 from decylamine.
N-Decyl-4-oxo-4H-1 -benzopyrán-2-karboxamid ‘H-NMR (CDClj): 0,88 (t, 3H, CHj); 1,10-1,42 (m, 14H, 7xCH2); 1,57-1,71 (m, 2H, CH2); 3,49 (q, 2H, CH2); 7,17 (s, IH, H-3); 7,20-7,54 (m, 2H, H-arom.); 7,68- 7,78 (m, IH, H-arom.); 8,19-8,25 (m, IH, H-arom.). 13C-NMR (CDClj): 14,09 (CHj); 22,66, 26,94, 29,26, 29,46, 29,51, 31,88,40,08 (CH2); 112,11 (C-3); 117,98, 125,94, 126,18, 134,45 (CH-arom.); 124,37, 154,80, 155,25(C-arom.); 159,16 (C=O); 178,14 (C=O).N-Decyl-4-oxo-4H-1-benzopyran-2-carboxamide 1 H-NMR (CDCl 3): 0.88 (t, 3H, CH 3); 1.10-1.42 (m, 14 H, 7xCH 2); 1.57-1.71 (m, 2H, CH2); 3.49 (q, 2H, CH2); 7.17 (s, 1H, H-3); 7.20-7.54 (m, 2H, H-arom.); 7.68-7.78 (m, 1H, H-arom.); 8.19-8.25 (m, 1H, H-arom.). 13 C-NMR (CDCl 3): 14.09 (CH 3); 22.66, 26.94, 29.26, 29.46, 29.51, 31,88,40,08 (CH2); 112.11 (C-3); 117.98, 125.94, 126.18, 134.45 (CH-arom.); 124.37, 154.80, 155.25 (C-arom.); 159.16 (C = O); 178.14 (C = O).
Výťažok: 56 %. T. t.: 95-97 °C.Yield: 56%. Mp: 95-97 ° C.
Príklad 4Example 4
N-Undecyl-4-oxo-4H-1 -benzopyrán-2-karboxamidN-Undecyl-4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z undecylamínu.It was prepared in analogy to Example 1 from undecylamine.
'H-NMR (CDCIj): 0,88 (t, 3H, CHj); 1,18-1,40 (m, 16H, 8xCH2); 1,58-1,72 (m, 2H, CH2); 3,49 (q, 2H, CH2); 7,12 (s, IH, H-3); 7,24-7,57 (m, 2H, H-arom.); 7,66- 7,78 (m, IH, H-arom.); 8,14-8,22 (m, IH, H-arom.). 13C-NMR (CDCIj): 13,97 (CH3); 22,53, 26,83, 29,14, 29,19, 29,30, 29,38, 29,48, 31,76, 40,00 (CH2); 111,72 (C-3); 118,03, 125,78, 125,78, 134,41 (CH-arom.); 124,12, 154,94, 155,15 (C-arom.); 159,09 (C=O); 178,11 (C=O).1 H-NMR (CDCl 3): 0.88 (t, 3H, CH 3); 1.18-1.40 (m, 16 H, 8xCH 2); 1.58-1.72 (m, 2H, CH2); 3.49 (q, 2H, CH2); 7.12 (s, 1H, H-3); 7.24-7.57 (m, 2H, H-arom.); 7.66-7.78 (m, 1H, H-arom.); 8.14-8.22 (m, 1H, H-arom.). 13 C-NMR (CDCl 3): 13.97 (CH 3 ); 22.53, 26.83, 29.14, 29.19, 29.30, 29.38, 29.48, 31.76, 40.00 (CH 2 ); 111.72 (C-3); 118.03, 125.78, 125.78, 134.41 (CH-arom.); 124.12, 154.94, 155.15 (C-arom.); 159.09 (C = O); 178.11 (C = O).
Výťažok: 87 %. T. t.: 104-106 °C.Yield: 87%. Mp: 104-106 ° C.
Príklad 5Example 5
N-Dodecyl-4-oxo-4H-1 -benzopyrán-2-karboxamidN-Dodecyl-4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z dodecylamínu.It was prepared in analogy to Example 1 from dodecylamine.
'H-NMR (CDCIj): 0,88 (t, 3H, CH3); 1,18-1,45 (m, 18H, 9xCH2); 1,60-1,74 (m, 2H, CH2); 3,48 (q, 2H, CH2); 6,97 (br. s., IH, NH); 7,15 (s, IH, H-3); 7,39-7,55 (m, 2H, H-arom.); 7,68- 7,78 (m, IH, H-arom.); 8,17-8,25 (m, IH, H-arom.). ’3C-NMR (CDCIj): 14,06 (CHj); 22,63, 26,91,1 H-NMR (CDCl 3): 0.88 (t, 3H, CH 3 ); 1.18 to 1.45 (m, 18 H, 9xCH 2); 1.60-1.74 (m, 2H, CH2); 3.48 (q, 2H, CH2); 6.97 (br. S, 1H, NH); 7.15 (s, 1H, H-3); 7.39-7.55 (m, 2H, H-arom.); 7.68-7.78 (m, 1H, H-arom.); 8.17-8.25 (m, 1H, H-arom.). '3 C-NMR (CDCl): 14.06 (CH); 22.63, 26.91,
29.22, 29,28, 29,41, 29,47, 29,54, 31,85, 40,05 (CH2); 112,01 (C-3); 117,99, 125,89, 126,08, 134,44 (CH-arom.); 124,29, 154,81, 155,21 (C-arom.); 159,13 (C=O); 178,13 (C=O).29.22, 29.28, 29.41, 29.47, 29.54, 31.85, 40.05 (CH2); 112.01 (C-3); 117.99, 125.89, 126.08, 134.44 (CH-arom.); 124.29, 154.81, 155.21 (C-arom.); 159.13 (C = O); 178.13 (C = O).
Výťažok: 81 %. T. t.: 110-115 °C.Yield: 81%. Mp: 110-115 ° C.
Príklad 6Example 6
N-Tridecyl-4-oxo-4H-1 -benzopyrán-2-karboxamidN-Tridecyl-4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z tridecylamínu.Prepared in analogy to Example 1 from tridecylamine.
'H-NMR (CDCIj): 0,88 (t, 3H, CHj); 1,16-1,45 (m, 22H, 1 1xCH2); 1,60-1,72 (m, 2H, CH2); 3,49 (q, 2H, CH2); 6,98 (br. s., IH, NH); 7,17 (s, IH, H-3); 7,40-7,58 (m, 2H, H-arom.); 7,68- 7,78 (m, IH, H-arom.); 8,18-8,24 (m, IH, H-arom.). 13C-NMR (CDCIj): 14,07 (CH3); 22,65, 26,92,1 H-NMR (CDCl 3): 0.88 (t, 3H, CH 3); 1.16 to 1.45 (m, 22 H, 1 1xCH 2); 1.60-1.72 (m, 2H, CH2); 3.49 (q, 2H, CH2); 6.98 (br. S, 1H, NH); 7.17 (s, 1H, H-3); 7.40-7.58 (m, 2H, H-arom.); 7.68-7.78 (m, 1H, H-arom.); 8.18-8.24 (m, 1H, H-arom.). 13 C-NMR (CDCl 3): 14.07 (CH 3 ); 22.65, 26.92,
29.23, 29,31, 29,41, 29,48, 29,54, 29,60, 31,87, 40,05 (CH2); 112,01 (C-3); 117,99, 125,90, 126,08, 134,44 (CH-arom.); 124,30, 154,82, 155,22 (C-arom.); 159,13 (C=O); 178,13 (C=O).29.23, 29.31, 29.41, 29.48, 29.54, 29.60, 31.87, 40.05 (CH2); 112.01 (C-3); 117.99, 125.90, 126.08, 134.44 (CH-arom.); 124.30, 154.82, 155.22 (C-arom.); 159.13 (C = O); 178.13 (C = O).
Výťažok: 84 %. T. t.:98-99 °C.Yield: 84%. Mp: 98-99 ° C.
Príklad 7Example 7
N-Tetradecyl-4-oxo-4H-1 -benzopyrán-2-karboxamidN-Tetradecyl-4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z tetradecylaminu.Prepared in analogy to Example 1 from tetradecylamine.
‘H-NMR (CDCIj): 0,88 (t, 3H, CHj); 1,15-1,48 (m, 24H, 12xCH2); 1,58-1,71 (m, 2H, CH2); 3,49 (q, 2H, CH2); 6.89 (br. s., IH, NH); 7,14 (s, IH, H-3); 7,41-7,56 (m, 2H, H-arom.); 7,68- 7,78 (m, IH, H-arom.); 8,17-8,24 (m, IH, H-arom.). 13C-NMR (CDCIj): 14,05 (CH,); 22,64, 26,94, 29,25, 29,34, 29,40, 29,48, 29,54, 29,60, 31,77, 40,07 (CH2); 112,03 (C-3); 117,96, 125,91, 126,11, 134,43 (CH-arom.); 124,30, 154,81, 155,22 (C-arom.); 159,12 (C=O);1 H-NMR (CDCl 3): 0.88 (t, 3H, CH 3); 1.15-1.48 (m, 24H, 12xCH 2); 1.58-1.71 (m, 2H, CH2); 3.49 (q, 2H, CH2); 6.89 (br. S, 1H, NH); 7.14 (s, 1H, H-3); 7.41-7.56 (m, 2H, H-arom.); 7.68-7.78 (m, 1H, H-arom.); 8.17-8.24 (m, 1H, H-arom.). 13 C-NMR (CDCl 3): 14.05 (CH 2); 22.64, 26.94, 29.25, 29.34, 29.40, 29.48, 29.54, 29.60, 31.77, 40.07 (CH 2 ); 112.03 (C-3); 117.96, 125.91, 126.11, 134.43 (CH-aromatic); 124.30, 154.81, 155.22 (C-arom.); 159.12 (C = O);
178,21 (C=O).178.21 (C = O).
Výťažok: 89 %. T. t.:85-89 °C.Yield: 89%. Mp: 85-89 ° C.
Príklad 8Example 8
N-Hexadecyl-4-oxo-4H-1 -benzopyrán-2-karboxamidN-Hexadecyl-4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z hexadecylamínu.Prepared in analogy to Example 1 from hexadecylamine.
'H-NMR (CDCIj): 0,88 (t, 3H, CH3); 1,14-1,45 (m, 28H, 14xCH2); 1,58-1,73 (m, 2H, CH2); 3.,1 (q, 2H, CH2); 6,89 (br. s., IH, NH); 7,14 (s, IH, H-3); 7,39-7,53 (m, 2H, H-arom.); 7,68- 7,79 (m, IH, H-arom.); 8,18-8,23 (m, IH, H-arom.). 13C-NMR (CDCIj): 14,08 (CH,); 22,68, 26,94, 29,06, 29,26, 29,35, 29,44, 29.51, 29,58, 29,68, 31,91, 40,08 (CH2); 112,21 (C-3); 117,96, 125,99, 126,14, 134,47 (CH-arom.); 124,34, 154,81, 155,27 (C-arom.); 159,17 (C=O); 178,08 (C=O).1 H-NMR (CDCl 3): 0.88 (t, 3H, CH 3 ); 1.14 to 1.45 (m, 28H, 14xCH 2); 1.58-1.73 (m, 2H, CH2); 3, 1 (q, 2H, CH2); 6.89 (br. S, 1H, NH); 7.14 (s, 1H, H-3); 7.39-7.53 (m, 2H, H-arom.); 7.68-7.79 (m, 1H, H-arom.); 8.18-8.23 (m, 1H, H-arom.). 13 C-NMR (CDCl 3): 14.08 (CH 2); 22.68, 26.94, 29.06, 29.26, 29.35, 29.44, 29.51, 29.58, 29.68, 31.91, 40.08 (CH 2 ); 112.21 (C-3); 117.96, 125.99, 126.14, 134.47 (CH-arom.); 124.34, 154.81, 155.27 (C-arom.); 159.17 (C = O); 178.08 (C = O).
Výťažok: 88 %. T. t.: 77-81 °C.Yield: 88%. Mp: 77-81 ° C.
Príklad 9Example 9
N-Oktadecyl-4-oxo-4H-1 -benzopyrán-2-karboxamidN-Octadecyl-4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z oktadecylamínu.It was prepared in analogy to Example 1 from octadecylamine.
'H-NMR (CDCIj): 0,86 (t, 3H, CH3); 1,15-1,45 (m, 32H, 16xCH2); 1,58-1,71 (m, 2H, CH2); 3.48 (q, 2H, CH2); 6.90 (br. s., IH, NH); 7,17 (s, IH, H-3); 7,38-7,54 (m, 2H, Harom.); 7,68- 7,79 (m, IH, H-arom.); 8.18-8.24 (m, IH, Harom.). 13C-NMR (CDCIj): 14,10 (CH3);.22,68, 26,97, 29,13, 29,26, 29,35, 29,41, 29,44, 29,51, 29,55, 29,58, 29,68, 31,91, 40,11 (CH2); 112,08(C-3); 117,99, 125,94,1 H-NMR (CDCl 3): 0.86 (t, 3H, CH 3 ); 1.15-1.45 (m, 32H, 16xCH 2); 1.58-1.71 (m, 2H, CH2); 3:48 (q, 2H, CH2); 6.90 (br. S, 1H, NH); 7.17 (s, 1H, H-3); 7.38-7.54 (m, 2H, Harom); 7.68-7.79 (m, 1H, H-arom.); 8.18-8.24 (m, 1H, Harom). 13 C-NMR (CDCl 3): 14.10 (CH 3 ); 22.68, 26.97, 29.13, 29.26, 29.35, 29.41, 29.44, 29.51, 29 , 55, 29.58, 29.68, 31.91, 40.11 (CH2); 112.08 (C-3); 117.99, 125.94,
126,16, 134,46 (CH-arom); 124,35, 154,81, 155,24 (C-arom.); 159,15 (C=O); 178,16 (C=O).126.16, 134.46 (CH-arom); 124.35, 154.81, 155.24 (C-arom.); 159.15 (C = O); 178.16 (C = O).
Výťažok: 68%. T.t.:85-86°C.Yield: 68%. T.t.:85-86°C.
Príklad 10Example 10
N-l-(4-Amir>obutyl)-4-oxo-4H-l-benzopyrán-2-karboxamidN-l- (4-Amir> obutyl) -4-oxo-4H-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 1,4-diaminobutánu.Prepared in analogy to Example 1 from 1,4-diaminobutane.
'H-NMR (CDCIj): 1,15-2,45 (m, 8H, CH2); 1,58-1,71 (m, 2H, CH2); 7,21 (s, IH, H-3); 7,36-7,54 (m, 2H, H-arom.);1 H-NMR (CDCl 3): 1.15-2.45 (m, 8H, CH 2 ); 1.58-1.71 (m, 2H, CH2); 7.21 (s, 1H, H-3); 7.36-7.54 (m, 2H, H-arom.);
7,68- 7,81 (m, IH, H-arom.); 8,18-8,24 (m, IH, H-arom.). 13C-NMR (CDCIj): 26,97, 29,35, 31,98, 40,07 (CH2);7.68-7.81 (m, 1H, H-arom.); 8.18-8.24 (m, 1H, H-arom.). 13 C-NMR (CDCl 3): 26.97, 29.35, 31.98, 40.07 (CH 2 );
112,21 (C-3); 117,96, 125,94, 126,16, 134,50 (CH-arom.); 124,33, 154,99, 155,26 (C-arom.); 159,21 (C=O); 178,19 (C=O).112.21 (C-3); 117.96, 125.94, 126.16, 134.50 (CH-arom.); 124.33, 154.99, 155.26 (C-arom.); 159.21 (C = O); 178.19 (C = O).
Výťažok: 64 %. T. t.: olejYield: 64%. T.I.: oil
Príklad 11Example 11
N-(3-(N,N-Dimetylamino)-2,2-dimetylprop-l-yl))-4-oxo-4H-1 -benzopyrán-2-karboxamidN- (3- (N, N-Dimethylamino) -2,2-dimethylprop-1-yl)) - 4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 'H-NMR (CDCIj): 1,02 (s, 6H, 2xCH3); 2,47 (s, 6H, 2x CH3); 2,47 (s, 2H, CH2); 3.40(s, 2H, CH2); 7,14 (s, IH, H-3); 7,38-7,50 (m, 2H, H-arom.); 7,65-7,78 (m, IH, H-arom.); 8,18-8,26 (m, IH, H-arom.). I3C-NMR (CDCI,):Prepared in analogy to Example 1 from 1 H-NMR (CDCl 3): 1.02 (s, 6H, 2xCH 3 ); 2.47 (s, 6H, 2 CH3); 2.47 (s, 2H, CH2); 3:40 (s, 2H, CH2); 7.14 (s, 1H, H-3); 7.38-7.50 (m, 2H, H-arom.); 7.65-7.78 (m, 1H, H-arom.); 8.18-8.26 (m, 1H, H-arom.). 13 C-NMR (CDCl 3):
25,23, 48,38 (CHj); 34,31, 51,72(CH2); 71,39 (C); 111,73 (C-3); 117,77, 125,71, 126,14, 134,36 (CH-arom.); 124,41, 154,90,155,43 (C-arom.); 159,32(C=O); 178,35 (C=O). Výťažok: 59 %. T. t.: 105-107 °C.25.23, 48.38 (CH 3); 34.31, 51.72 (CH2); 71.39 (C); 111.73 (C-3); 117.77, 125.71, 126.14, 134.36 (CH-arom.); 124.41, 154.90, 155.43 (C-arom.); 159.32 (C = O); 178.35 (C = O). Yield: 59%. Mp: 105-107 ° C.
Príklad 12Example 12
N-(3 -(Aminocyklohcxyljprop-1 -yl))-4-oxo-4H-1 -benzopyrán-2-karboxamidN- (3- (Aminocyclohexyl) prop-1-yl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 'H-NMR (CDCIj): 0,85-2,10 (m, 12H); 3,45-3,65,(m, 5H); 7,17(s, IH, H-3); 7,35-7,75 (m, 3H, H-arom.); 8,12-8,28, (m, IH, H-arom.). 13C-NMR (CDCIj): 24,81, 25,33, 25,52, 29.38, 32,03, 37,27, 39.07(CH2); 59.68 (CH); 110,96, 111,62 (C-3); 117,94, 118,39, 125,69, 125,97, 134,45, 134,51 (CH-arom.); 124,12, 124,21, 154,90, 158,91, 159.50 (C-arom.); 163,24 (CO); 177,37 (C=O).Prepared in analogy to Example 1 from 1 H-NMR (CDCl 3): 0.85-2.10 (m, 12H); 3.45-3.65 (m, 5H); 7.17 (s, 1H, H-3); 7.35-7.75 (m, 3H, H-arom.); 8.12-8.28, (m, 1H, H-arom.). 13 C-NMR (CDCl 3): 24.81, 25.33, 25.52, 29.38, 32.03, 37.27, 39.07 (CH 2 ); 59.68 (CH); 110.96, 111.62 (C-3); 117.94, 118.39, 125.69, 125.97, 134.45, 134.51 (CH-arom.); 124.12, 124.21, 154.90, 158.91, 159.50 (C-arom.); 163.24 (CO); 177.37 (C = O).
Výťažok: 64 %. T. t.: 83-85 °C.Yield: 64%. Mp: 83-85 ° C.
Príklad 13Example 13
N-(2-((4-Amíno-4-metyl)-cyklohexyl)-prop-2-yl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN- (2 - ((4-Amino-4-methyl) -cyclohexyl) -prop-2-yl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z ‘H-NMR (CDClj): 1,20-2,55 (m, 18H); 7,06-7,08 (IH, H-3); 7,35-7,55 (m, 2H, H-arom.); 7,60- 7,79 (m, IH, H-arom.); 8,12-8,23 (m, IH, H-arom.). 13C-NMR (CDClj): 24,54, 27,23(CHj); 22,89, 36,34, 53,99, 57,57(CH2); 43,78 (CH); 111,50, 111,59 (C-3); 117,99, 118,12, 125,96, 134,48, 134,55 (CH-arom.); 124,11, 124,15, 155,05, 155,09, 155,26, 155,36 (C-arom.); 158,11, 158,27 (C=O); 178,11 (C=O).Prepared in analogy to Example 1 from 1 H-NMR (CDCl 3): 1.20-2.55 (m, 18H); 7.06-7.08 (1H, H-3); 7.35-7.55 (m, 2H, H-arom.); 7.60-7.79 (m, 1H, H-arom.); 8.12-8.23 (m, 1H, H-arom.). 13 C-NMR (CDCl 3): 24.54, 27.23 (CH 3); 22.89, 36.34, 53.99, 57.57 (CH2); 43.78 (CH); 111.50, 111.59 (C-3); 117.99, 118.12, 125.96, 134.48, 134.55 (CH-arom.); 124.11, 124.15, 155.05, 155.09, 155.26, 155.36 (C-arom.); 158.11, 158.27 (C = O); 178.11 (C = O).
Výťažok: 67 %. T. t.: olejYield: 67%. T.I.: oil
Príklad 14Example 14
N-(Cykloheptyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN- (Cycloheptyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z cykloheptylamínu.It was prepared in a manner analogous to Example 1 from cycloheptylamine.
' H-NMR (CDClj): 1,40-2,15 (m, 12H, 6xCH2); 4,05-4,20 (m, IH, CH); 7,14 (s, IH, H-3); 7,19 (d, IH, NH); 7,39-7,60 (m, 2H, H-arom.); 7,65-7,78 (m, IH, H-arom.); 8,15-8,22 (m, IH, H-arom.). I3C-NMR (CDClj): 23,96, 27,65, 34,61 (CH2); 51,19 (CH); 111,56 (C-3); 118,00, 125,63, 134,27 (CH-arom.); 123,98, 155,04 (C-arom.); 157,82 (C=O); 178,01 (C=O).1 H-NMR (CDCl 3): 1.40-2.15 (m, 12H, 6xCH 2 ); 4.05-4.20 (m, 1H, CH); 7.14 (s, 1H, H-3); 7.19 (d, 1H, NH); 7.39-7.60 (m, 2H, H-arom.); 7.65-7.78 (m, 1H, H-arom.); 8.15-8.22 (m, 1H, H-arom.). 13 C-NMR (CDCl 3): 23.96, 27.65, 34.61 (CH 2 ); 51.19 (CH); 111.56 (C-3); 118.00, 125.63, 134.27 (CH-arom.); 123.98, 155.04 (C-arom.); 157.82 (C = O); 178.01 (C = O).
Výťažok: 65%. T. t.: 109-114 “C.Yield: 65%. T.: 109-114 “C.
Príklad 15Example 15
N-(Cyklooktyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN- (Cyclooctyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z cyklooktylamínu.It was prepared in a manner analogous to Example 1 from cyclooctylamine.
'H-NMR (CDClj): 1,20-2,20 (m, 14H, 7xCH2); 4,05-4,26 (m, IH, CH); 7,16 (s, IH, H-3); 7,36-7,55 (m, 2H, H-arom.); 7.66-7.78 (m, IH, H-arom.); 8,18-8,22 (m, IH, H-arom.). 13C-NMR (CDClj): 23,95, 24,22, 27,59, 34,34 (CH2); 51,65 (CH); 111,67 (C-3); 118,01, 125,65, 134,28 (CH-arom.); 124,08, 155,16 (C-arom.); 157,92 (C=O); 178,02 (C=O).1 H-NMR (CDCl 3): 1.20-2.20 (m, 14H, 7xCH 2 ); 4.05-4.26 (m, 1H, CH); 7.16 (s, 1H, H-3); 7.36-7.55 (m, 2H, H-arom.); 7.66-7.78 (m, 1H, H-arom.); 8.18-8.22 (m, 1H, H-arom.). 13 C-NMR (CDCl 3): 23.95, 24.22, 27.59, 34.34 (CH 2 ); 51.65 (CH); 111.67 (C-3); 118.01, 125.65, 134.28 (CH-arom.); 124.08, 155.16 (C-arom.); 157.92 (C = O); 178.02 (C = O).
Výťažok: 60 %. T. t.: 99-104 °C.Yield: 60%. Mp: 99-104 ° C.
Príklad 16Example 16
N-((3R)-Hexahydro-2H-azepin-2-one-3-yl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN - ((3R) -Hexahydro-2H-azepin-2-one-3-yl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 'H-NMR (CDClj): 1,40-2,34 (m, 6H, 3xCH2); 3,30-3,42 (m, 2H, CH2); 4,64-4,77 (m, IH, CH); 6,20-6,32 (br. s., IH, NH); 7,16 (s, IH, H-3); 7,40-7,80 (m, 3H, H-arom.); 8,18-8.24 (m, IH, H-arom.); 8,32-8,40 (br. s., IH, NH). I3C-NMR (CDClj): 27,93, 28,82, 31,14, 42,24 (4xCH2); 52,78 (CH); 112,02 (C-3); 118,39, 125,89, 125,95, 134,52 (CH-arom.); 124,33, 154,74, 155,34 (C-arom.); 158,32 (C=O); 174,62 (C=O); 178,23 (C=O).Prepared in analogy to Example 1 from 1 H-NMR (CDCl 3): 1.40-2.34 (m, 6H, 3xCH 2 ); 3.30-3.42 (m, 2H, CH2); 4.64-4.77 (m, 1H, CH); 6.20-6.32 (br. S, 1H, NH); 7.16 (s, 1H, H-3); 7.40-7.80 (m, 3H, H-arom.); 8.18-8.24 (m, 1H, H-arom.); 8.32-8.40 (br. S, 1H, NH). 13 C-NMR (CDCl 3): 27.93, 28.82, 31.14, 42.24 (4xCH 2 ); 52.78 (CH); 112.02 (C-3); 118.39, 125.89, 125.95, 134.52 (CH-arom.); 124.33, 154.74, 155.34 (C-arom.); 158.32 (C = O); 174.62 (C = O); 178.23 (C = O).
Výťažok: 55 %. T. t. : 269-270 °C.Yield: 55%. T. t. : 269-270 ° C.
Príklad 17Example 17
N-((3S)-Hexahydro-2H-azepin-2-one-3-yl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN - ((3S) -Hexahydro-2H-azepin-2-one-3-yl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 'H-NMR (CDClj): 1,30-2,34 (m, 6H, 3xCH2); 3,25-3,40 (m, 2H, CH2); 4,63-4,77 (m, IH, CH); 6,20-6,35 (br. s., IH, NH); 7,16 (s, IH, H-3); 7,40-7,80 (m, 3H, H-arom.); 8,18-8,25 (m, IH, H-arom.); 8,32-8,40 (br. s., IH, NH). 13C-NMR (CDClj): 27,93, 28,83, 31,14, 42,23 (4xCHä);Prepared in analogy to Example 1 from 1 H-NMR (CDCl 3): 1.30-2.34 (m, 6H, 3xCH 2 ); 3.25-3.40 (m, 2H, CH2); 4.63-4.77 (m, 1H, CH); 6.20-6.35 (br. S, 1H, NH); 7.16 (s, 1H, H-3); 7.40-7.80 (m, 3H, H-arom.); 8.18-8.25 (m, 1H, H-arom.); 8.32-8.40 (br. S, 1H, NH). 13 C-NMR (CDCl): 27.93, 28.83, 31.14, 42.23 (4xCH A);
52,78 (CH); 112,02 (C-3); 118,38, 125,88, 125,95, 134,50 (CH-arom.); 124,33, 154,73, 155,33 (C-arom.); 158,31 (C=O); 174,59 (C=O); 178,22 (C=O).52.78 (CH); 112.02 (C-3); 118.38, 125.88, 125.95, 134.50 (CH-arom.); 124.33, 154.73, 155.33 (C-arom.); 158.31 (C = O); 174.59 (C = O); 178.22 (C = O).
Výťažok: 61%. T. t.: 270-272 °C.Yield: 61%. Mp: 270-272 ° C.
Príklad 18Example 18
N-( 1 - Adamantyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN- (1-Adamanthyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 1-aminoadamantánu.Prepared in analogy to Example 1 from 1-aminoadamantane.
'H-NMR (CDClj): 1,65-2,22 (m, 15H, H-alif.); 3,86 (s, IH, CH); 6,59 (br. s., IH, NH); 7,40- 8,25 (m, 4H, H-arom). 13C-NMR (CDClj): 29,23, 29,37 (CH); 36,08, 36,15, 40,87, 41,29, 52,90 (CH2); 111,51, 118,00, 125,80, 126,01, 134,34 (CH); 124,20,155,12, 155,43, 157,68 (C); 178,21 (C=O). Výťažok: 83 %. T. t.: 195-197 °C.1 H-NMR (CDCl 3): 1.65-2.22 (m, 15H, H-aliph.); 3.86 (s, 1H, CH); 6.59 (br. S, 1H, NH); 7.40-8.25 (m, 4H, H-aroma). 13 C-NMR (CDCl 3): 29.23, 29.37 (CH); 36.08, 36.15, 40.87, 41.29, 52.90 (CH 2 ); 111.51, 118.00, 125.80, 126.01, 134.34 (CH); 124.20, 155.12, 155.43, 157.68 (C); 178.21 (C = O). Yield: 83%. Mp: 195-197 ° C.
Príklad 19Example 19
N -1 -(Hexametyléniminyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN -1- (Hexamethyleniminyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 'H-NMR (CDClj): 1,60-1,85 (m, 8H, 4xCH2); 3,15-3,28 (m, 4H, 2xCH2); 7,14 (s, IH, H-3); 7,38-7,56 (m, 2H, H-arom.); 7,66-7,77 (m, IH, H-arom.); 8,14-8,20 (m, IH, H-arom.); 8,20-8,45 (br. s.. IH, NH). ,3C-NMR (CDClj):Prepared in analogy to Example 1 from 1 H-NMR (CDCl 3): 1.60-1.85 (m, 8H, 4xCH 2 ); 3.15-3.28 (m, 4H, 2 * CH2); 7.14 (s, 1H, H-3); 7.38-7.56 (m, 2H, H-arom.); 7.66-7.77 (m, 1H, H-arom.); 8.14-8.20 (m, 1H, H-arom.); 8.20-8.45 (br. S, 1H, NH). 13 C-NMR (CDCl 3):
26,24, 26,78, 57,91 (CH2j; 112,04 (C-3); 118,06, 125,80, 134,40 (CH-arom.); 124,20, 155,14, 177,86 (C-arom., C=O).26.24, 26.78, 57.91 (CH2 ) ; 112.04 (C-3); 118.06, 125.80, 134.40 (CH-arom.); 124.20, 155.14 , 177.86 (C-arom., C = O).
Výťažok: 73 %. T. t.: 188-189 °C.Yield: 73%. Mp: 188-189 ° C.
Príklad 20Example 20
N,N-(Di-(l -metylprop-1 -yl))-4-oxo-4H-1 -benzopyrán-2-karboxamidN, N- (Di- (1-methylprop-1-yl)) - 4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 'H-NMR (CDClj): 1,05-2,69 (m, 14H, 2xCH, 4xCH3); 3,14-3,23 (d, 2H, CH2); 3,23-3,35 (d, 2H, CH2); 7,13 (s, IH, H-3); 7,42-7,53 (m, 2H, H-arom); 7,68-7,74 (m, IH, H-arom.); 8,20-8,28 (m, IH, H-arom.). ,3C-NMR (CDClj): 21,56, 21,67, 23,08, 23,14 (CH3); 45,78, 45,98 (CH2); 31,45, 31,88 (CH); 111,44 (C-3); 117,67, 125,65, 125,74, 134,08 (CH); 124,22, 155,47, 158,78 (C); 160,23, 177,98 (C=O).Prepared in analogy to Example 1 from 1 H-NMR (CDCl 3): 1.05-2.69 (m, 14H, 2xCH, 4xCH 3 ); 3.14-3.23 (d, 2H, CH2); 3.23-3.35 (d, 2H, CH2); 7.13 (s, 1H, H-3); 7.42-7.53 (m, 2H, H-aroma); 7.68-7.74 (m, 1H, H-arom.); 8.20-8.28 (m, 1H, H-arom.). 13 C-NMR (CDCl 3): 21.56, 21.67, 23.08, 23.14 (CH 3 ); 45.78, 45.98 (CH2); 31.45, 31.88 (CH); 111.44 (C-3); 117.67, 125.65, 125.74, 134.08 (CH); 124.22, 155.47, 158.78 (C); 160.23, 177.98 (C = O).
Výťažok: 69 %. T. t.: olej.Yield: 69%. T.I.: oil.
Príklad 21Example 21
N,N-(Di-(2-metylprop-1 -yl))-4-oxo-4H-l -benzopyrán-2-karboxamidN, N- (Di- (2-methylprop-1-yl)) - 4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z di-(2-metylprop-l-yl)amínu.Prepared in analogy to Example 1 from di- (2-methylprop-1-yl) amine.
'H-NMR (CDClj): 1,05-2,69 (m, 14H, 2xCH, 4xCH3); 3,14-3,23 (d, 2H, CH2); 3,23-3,35 (d, 2H, CH2); 7,13 (s, IH, H-3); 7,42-7,53 (m, 2H, H-arom); 7,68-7,74 (m, IH, H-arom.); 8,20-8,28 (m, IH, H-arom.). 13C-NMR (CDClj): 21,56, 21,67, 23,08, 23,14 (CHj); 45,78, 45,98 (CH2); 31,45, 31,88 (CH); 111,44 (C-3); 117,67, 125,65, 125,74, 134,08 (CH); 124,22, 155,47, 158,78 (C); 160,23, 177,98 (C=O).1 H-NMR (CDCl 3): 1.05-2.69 (m, 14H, 2xCH, 4xCH 3 ); 3.14-3.23 (d, 2H, CH2); 3.23-3.35 (d, 2H, CH2); 7.13 (s, 1H, H-3); 7.42-7.53 (m, 2H, H-aroma); 7.68-7.74 (m, 1H, H-arom.); 8.20-8.28 (m, 1H, H-arom.). 13 C-NMR (CDCl 3): 21.56, 21.67, 23.08, 23.14 (CH 3); 45.78, 45.98 (CH2); 31.45, 31.88 (CH); 111.44 (C-3); 117.67, 125.65, 125.74, 134.08 (CH); 124.22, 155.47, 158.78 (C); 160.23, 177.98 (C = O).
Výťažok: 72 %. T. t.: olej.Yield: 72%. T.T.: oil.
Príklad 22 N,N-(Dipentyl)-4-oxo-4H-l-benzopyrán-2-karboxamidExample 22 N, N- (Dipentyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z dipcntylamínu.It was prepared in an analogous manner to that in Example 1 from diphtylamine.
'H-NMR (CDClj): 0,80-0,95 (m, 6H, 2xCH}); 1,10-1,69 (m, 12H, 6x CH2); 3,30-3,41 (t, 2H, CH2); 3,42-3,55 (t, 2H, CH2); 6,59 (s, IH, H-3); 7,42-7,53 (m, 2H, H-arom); 7,66H-NMR (CDCl): 0.80-0.95 (m, 6H, 2 x CH}); 1.10 to 1.69 (m, 12 H, 6 x CH2); 3.30-3.41 (t, 2H, CH2); 3.42-3.55 (t, 2H, CH2); 6.59 (s, 1H, H-3); 7.42-7.53 (m, 2H, H-aroma); 7.66
-7,76 (m, IH, H-arom.); 8,19-8,27 (m, IH, H-arom.). 13C-NMR (CDClj): 13,99, 14,08 (CH3); 22,39, 22,49, 26,31, 26,74, 27,04, 28,76, 29,06, 29,20, 31,45, 31,87,-7.76 (m, 1H, H-arom.); 8.19-8.27 (m, 1H, H-arom.). 13 C-NMR (CDCl 3): 13.99, 14.08 (CH 3 ); 22.39, 22.49, 26.31, 26.74, 27.04, 28.76, 29.06, 29.20, 31.45, 31.87,
47.67, 48,98 (CH2); 110,94 (C-3); 117,97, 125,63, 125,71, 134,13 (CH); 124,19, 155,67, 159,08 (C); 162,03, 178,23 (C=O).47.67, 48.98 (CH2); 110.94 (C-3); 117.97, 125.63, 125.71, 134.13 (CH); 124.19, 155.67, 159.08 (C); 162.03, 178.23 (C = O).
Výťažok: 71 %. T. t.: olej.Yield: 71%. T.T.: oil.
Príklad 23 N,N-(Dihexyl)-4-oxo-4H-l-benzopyrán-2-karboxamidExample 23 N, N- (Dihexyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z dihexylamínu.It was prepared in a manner analogous to Example 1 from dihexylamine.
'H-NMR (CDClj): 0,80-0,95 (m, 6H, 2xCH3); 1,10-1,39 (m, 12H, 6x CH2); 1,55-1,75 (m, 4H, 2x CH2); 3,30-3,41 (t, 2H, CH2); 3,42-3,55 (t, 2H, CH2); 6,59 (s, IH, H-3); 7,42-7,53 (m, 2H, H-arom); 7,66-7,76 (m, IH, H-arom.);1 H-NMR (CDCl 3): 0.80-0.95 (m, 6H, 2xCH 3 ); 1.10-1.39 (m, 12 H, 6 x CH2); 1.55-1.75 (m, 4H, 2 CH2); 3.30-3.41 (t, 2H, CH2); 3.42-3.55 (t, 2H, CH2); 6.59 (s, 1H, H-3); 7.42-7.53 (m, 2H, H-aroma); 7.66-7.76 (m, 1H, H-arom.);
8,19-8,27 (m, IH, H-arom.). ,3C-NMR (CDClj): 13,99, 14,08 (CHj); 22,39, 22,49, 26,31, 26,74, 27,04, 28,76, 29,06, 29,20, 31,45, 31,87, 47,67, 48,98 (CH2); 110,94 (C-3); 117,97, 125,63, 125,71, 134,13 (CH); 124,19,8.19-8.27 (m, 1H, H-arom.). 13 C-NMR (CDCl 3): 13.99, 14.08 (CH 3); 22.39, 22.49, 26.31, 26.74, 27.04, 28.76, 29.06, 29.20, 31.45, 31.87, 47.67, 48.98 (CH 2) ); 110.94 (C-3); 117.97, 125.63, 125.71, 134.13 (CH); 124.19.
155.67, 159,08 (C); 162,03, 178,23 (C=O).155.67, 159.08 (C); 162.03, 178.23 (C = O).
Výťažok: 85 %. T. t.: olej.Yield: 85%. T.T.: oil.
Príklad 24Example 24
N,N-(Dioktyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN, N- (Dioctyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z dioktylamínu.It was prepared in analogy to Example 1 from dioctylamine.
'H-NMR (CDClj): 0,80-0,95 (m, 6H, 2xCH3); 1,15-1,40 (m, 20H, lOx CHj); 1,55-1,75 (m, 4H, 2x CHj); 3,25-3,36 (t, 2H, CH2); 3,42-3,54 (t, 2H, CH2); 6,50 (s, IH, H-3); 7,40-7,52 (m, 2H, H-arom); 7,65-7,76 (m, IH, H-arom.); 8,18-8,25 (m, IH, H-arom.). I3C-NMR (CDClj): 13,90, 13,94 (CHj); 22,39, 22,49, 26,51, 26,84, 27,08, 28,76, 28,95, 29,01, 29,07, 29,16, 31,52, 31,64, 45,46, 48,78 (CH2); 110,94 (C-3); 117,97, 125,63, 125,71, 134,12 (CH);1 H-NMR (CDCl 3): 0.80-0.95 (m, 6H, 2xCH 3 ); 1.15-1.40 (m, 20H, 10x CH3); 1.55-1.75 (m, 4H, 2 * CH3); 3.25-3.36 (t, 2H, CH2); 3.42-3.54 (t, 2H, CH2); 6.50 (s, 1H, H-3); 7.40-7.52 (m, 2H, H-aroma); 7.65-7.76 (m, 1H, H-arom.); 8.18-8.25 (m, 1H, H-arom.). 13 C-NMR (CDCl 3): 13.90, 13.94 (CH 3); 22.39, 22.49, 26.51, 26.84, 27.08, 28.76, 28.95, 29.01, 29.07, 29.16, 31.52, 31.64, 45, 46, 48.78 (CH2); 110.94 (C-3); 117.97, 125.63, 125.71, 134.12 (CH);
124,17, 155,57, 159,06 (C); 162,04, 178,21 (C-O). Výťažok: 81 %. T. t.: olej.124.17, 155.57, 159.06 (C); 162.04, 178.21 (C-O). Yield: 81%. Mp: oil.
Príklad 25Example 25
N,N-(Didecyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN, N- (Didecyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z didecylamínu.It was prepared analogously to Example 1 from didecylamine.
'H-NMR (CDClj): 0,75-0,88 (m, 6H, 2xCH3); 1,10-1,40 (m, 28H, 12x CH2); 1,65-1,85 (m, 4H, 2x CH2); 2,95-3,12 (m, 4H, 2xCHj); 7,12 (s, IH, H-3); 7,38-7,65 (m, 2H, H-arom); 7,65-7,80 (m, IH, H-arom.); 8,15-8,20 (m, IH, H-arom.). 13C-NMR (CDClj): 14,09 (CH3); 22,66, 25,73, 26,78, 29,21, 29,30, 29,55, 31,87, 47,80 (CH2); 112,64 (C-3); 118,55, 125,91, 126,24, 135,03 (CH); 124,21, 153,94, 155,32 (C); 158,43,178,02 (C=O).1 H-NMR (CDCl 3): 0.75-0.88 (m, 6H, 2xCH 3 ); 1.10-1.40 (m, 28H, 12x CH2); 1.65-1.85 (m, 4H, 2 CH2); 2.95-3.12 (m, 4H, 2xCH3); 7.12 (s, 1H, H-3); 7.38-7.65 (m, 2H, H-aroma); 7.65-7.80 (m, 1H, H-arom.); 8.15-8.20 (m, 1H, H-arom.). 13 C-NMR (CDCl 3): 14.09 (CH 3 ); 22.66, 25.73, 26.78, 29.21, 29.30, 29.55, 31.87, 47.80 (CH2); 112.64 (C-3); 118.55, 125.91, 126.24, 135.03 (CH); 124.21, 153.94, 155.32 (C); 158.43, 178.02 (C = O).
Výťažok: 78 %. T. t.: 133-134 °C.Yield: 78%. Mp: 133-134 ° C.
Príklad 26Example 26
N-Oktyl-N-(2,2-dimetylundec-1 -yl)-4-oxo-4H-1 benzopyrán-2-karboxamidN-Octyl-N- (2,2-dimethylundec-1-yl) -4-oxo-4H-1 benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z n-oktyl-(2,2-dimetylundec-1 -yl)amínu.Prepared in analogy to Example 1 from n-octyl- (2,2-dimethylundec-1-yl) amine.
'H-NMR (CDClj): 0,80-0,95 (m, 6H, 2xCH3); 1,10-1,40 (m, 32H, 2xCHj, 13x CHj); 1,50-1,75 (m, 4H, 2x CH2); 3,35-3,50 (m, 2H, CH2); 3,37 (s, 2H, CH2); 6,49 (s, IH, H-3); 7,40-7,55 (m, 2H, H-arom); 7,65-7,77 (m, IH, H-arom.); 8,20-8,26 (m, IH, H-arom.). I3C-NMR (CDClj): 14,02, 14,10 (CHj); 22,52, 22,68, 25,70, 25,96, 26,58, 29,04, 29,22, 29,34, 29,58, 29,64, 29,69, 30,58, 31,64, 31,91, 37,03, 41,25, 50,84, 54,03 (CHj CHj); 59,05 (C); 111,00 (C-3); 118,24, 125,78, 125,86, 134,24 (CH); 124,30, 155,85, 159,43 (C); 163,72, 177,57 (C=O).1 H-NMR (CDCl 3): 0.80-0.95 (m, 6H, 2xCH 3 ); 1.10-1.40 (m, 32H, 2xCH3, 13xCH3); 1.50-1.75 (m, 4H, 2 CH2); 3.35-3.50 (m, 2H, CH2); 3.37 (s, 2H, CH2); 6.49 (s, 1H, H-3); 7.40-7.55 (m, 2H, H-aroma); 7.65-7.77 (m, 1H, H-arom.); 8.20-8.26 (m, 1H, H-arom.). 13 C-NMR (CDCl 3): 14.02, 14.10 (CH 3); 22.52, 22.68, 25.70, 25.96, 26.58, 29.04, 29.22, 29.34, 29.58, 29.64, 29.69, 30.58, 31, 64, 31.91, 37.03, 41.25, 50.84, 54.03 (CH 2 CH 3); 59.05 (C); 111.00 (C-3); 118.24, 125.78, 125.86, 134.24 (CH); 124.30, 155.85, 159.43 (C); 163.72, 177.57 (C = O).
Výťažok: 75%. T. t.: olejYield: 75%. T.I.: oil
Príklad 27Example 27
N-( 1 -Metyletyl)-N-(2-metylprop-2-yl)-4-oxo-4H-1 benzopyrán-2-karboxamidN- (1-Methyl-ethyl) -N- (2-methyl-prop-2-yl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z (1 -metyletyl)-(2-metylprop-2-yl)amínu.Prepared in analogy to Example 1 from (1-methylethyl) - (2-methylprop-2-yl) amine.
'H-NMR (CDClj): 1,45 (d, 6H, 2xCH3); 1,49 (s, 9H, 3xCHj); 3,92 (hept., IH, CH); 6,45 (s, IH, H-3); 7,37-7,54 (m, 2H, H-arom); 7,65-7,76 (m, IH, H-arom.); 8,18-8,24 (m, IH, H-arom). 13C-NMR (CDClj): 22,53 (2xCH3); 29,34 (3xCHj); 50,50 (CH), 59,08 (C); 110,10, 118,26, 125,66, 125,79, 134,18 (CH-arom.); 124,35, 155,59, 161,38, 164,24,177,92 (C-arom., C=O).1 H-NMR (CDCl 3): 1.45 (d, 6H, 2xCH 3 ); 1.49 (s, 9H, 3xCH3); 3.92 (hept., 1H, CH); 6.45 (s, 1H, H-3); 7.37-7.54 (m, 2H, H-aroma); 7.65-7.76 (m, 1H, H-arom.); 8.18-8.24 (m, 1H, H-aroma). 13 C-NMR (CDCl 3): 22.53 (2xCH 3 ); 29.34 (3xCH3); 50.50 (CH), 59.08 (C); 110.10, 118.26, 125.66, 125.79, 134.18 (CH-arom.); 124.35, 155.59, 161.38, 164.24.177.92 (C-arom., C = O).
Výťažok: 78 %. T. t.: 81-83 °C.Yield: 78%. Mp: 81-83 ° C.
Príklad 28Example 28
N-(Cyklohexyl)-N-( 1 -metyletyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN- (Cyclohexyl) -N- (1-methylethyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z cyklohexyl-(l-metyletyl)amínu.Prepared in analogy to Example 1 from cyclohexyl- (1-methylethyl) amine.
'H-NMR (CDClj): 1,00-1,40 (m, 10H, 5xCH2); 1,46 (d, 6H, 2xCH3); 1,95-2,15 (m, IH, CH); 3,89 (hept., IH, CH); 6,49 (s, IH, H-3); 7,35-7,58 (m, 2H, H-arom); 7,63-7,76 (m, IH, H-arom.); 8,18-8,23 (m, IH, H-arom). I3C-NMR (CDClj): 22,41 (2xCH3); 21,74, 25,90, 26,22, 33,13, 33,36 (5xCH2); 49,55 (CH); 50,78 (CH), 111,07, 118,27, 125,76, 125,81, 134,16 (CH-arom.); 124,38, 155,72, 161,40, 164,32,177,86 (C-arom„ C=O).1 H-NMR (CDCl 3): 1.00-1.40 (m, 10H, 5xCH 2 ); 1.46 (d, 6 H, 2 x CH 3); 1.95-2.15 (m, 1H, CH); 3.89 (hept., 1H, CH); 6.49 (s, 1H, H-3); 7.35-7.58 (m, 2H, H-aroma); 7.63-7.76 (m, 1H, H-arom.); 8.18-8.23 (m, 1H, H-aroma). 13 C-NMR (CDCl 3): 22.41 (2xCH 3 ); 21.74, 25.90, 26.22, 33.13, 33.36 (5xCH 2 ); 49.55 (CH); 50.78 (CH), 111.07, 118.27, 125.76, 125.81, 134.16 (CH-arom.); 124.38, 155.72, 161.40, 164.32,177.86 (C-arom. C = O).
Výťažok: 84 %. T. t.: 86-90 °C.Yield: 84%. Mp: 86-90 ° C.
Príklad 29Example 29
N-(Cyklohexyl)-N-(2-metylprop-2-yl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN- (Cyclohexyl) -N- (2-methylprop-2-yl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z cyklohexyl-(2-metylprop-2-yl)amínu.Prepared in analogy to Example 1 from cyclohexyl- (2-methylprop-2-yl) amine.
'H-NMR (CDClj): 0,90 (s, 9H, 3xCH3); 1,00-1,40 (m, 10H, 5xCHj); 2,00-2,15 (m, IH, CH); 7,18-7,80 (m, 4H, H-arom); 8,19-8,28 (m, IH, H-arom). I3C-NMR (CDClj): 27,55 (3xCHj); 21,84, 26,01, 26,08, 33,10, 33,39 (5xCH2); 49,50 (CH); 112,11, 118,01, 125,90, 126,16, 134,39 (CH-arom.); 124,34, 155,73, 159,05, 160,09, 177,71 (C-arom., C=O).1 H-NMR (CDCl 3): 0.90 (s, 9H, 3xCH 3 ); 1.00-1.40 (m, 10H, 5 * CH2); 2.00-2.15 (m, 1H, CH); 7.18-7.80 (m, 4H, H-aroma); 8.19-8.28 (m, 1H, H-aroma). 13 C-NMR (CDCl 3): 27.55 (3xCH 3); 21.84, 26.01, 26.08, 33.10, 33.39 (5xCH 2); 49.50 (CH); 112.11, 118.01, 125.90, 126.16, 134.39 (CH-arom.); 124.34, 155.73, 159.05, 160.09, 177.71 (C-arom., C = O).
Výťažok: 69 %. T. t.: 192-194 °C.Yield: 69%. Mp: 192-194 ° C.
Príklad 30Example 30
N,N-(Dicyklohexyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN, N- (Dicyclohexyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z dicyklohexylamínu.Prepared in analogy to Example 1 from dicyclohexylamine.
'H-NMR (CDClj): 1,00-2,00 (m, 20H, 10xCH2); 2,40-2,65 (m, IH, CH); 3,10-3,40 (m, IH, CH); 6,42 (s, IH, H-3); 7,38-7,50 (m, 2H, H-arom); 7,65-7,77 (m, IH, H-arom);1 H-NMR (CDCl 3): 1.00-2.00 (m, 20H, 10xCH 2 ); 2.40-2.65 (m, 1H, CH); 3.10-3.40 (m, 1H, CH); 6.42 (s, 1H, H-3); 7.38-7.50 (m, 2H, H-aroma); 7.65-7.77 (m, 1H, H-aroma);
8,19-8,25 (m, IH, H-arom). I3C-NMR (CDClj): 25,00-31,40 (10xCH2); 55,38 (CH); 59,33 (CH); 109,81, 118,01, 125,61, 125,76, 134,14 (CH-arom.); 124,28, 155,63, 160,15, 161,79, 177,71 (C-arom., C=O).8.19-8.25 (m, 1H, H-aroma). 13 C-NMR (CDCl 3): 25.00-31.40 (10xCH 2 ); 55.38 (CH); 59.33 (CH); 109.81, 118.01, 125.61, 125.76, 134.14 (CH-arom.); 124.28, 155.63, 160.15, 161.79, 177.71 (C-arom., C = O).
Analýza pre C22H27NOjAnalysis for C 22 H 27 NO 3
Výťažok: 78 %. T. t.: 174-177 °C.Yield: 78%. Mp: 174-177 ° C.
Príklad 31 N-(Trifenylmetyl)-4-oxo-4H-l-benzopyrán-2-karboxamid Bol pripravený analogickým postupom ako v príklade 1 z trifenylmetylamínu.Example 31 N- (Triphenylmethyl) -4-oxo-4H-1-benzopyran-2-carboxamide Prepared in analogy to Example 1 from triphenylmethylamine.
'H-NMR (CDClj): 7,08-7,38 (m, 16Η, H-arom.); 7,40-7,54 (m, 2Η, H-arom); 7,66-7,78 (m, IH, H-arom.); 8,10-8,24 (m, IH, H-arom.). 13C-NMR (CDClj): 71.04 (C); 112.18,1 H-NMR (CDCl 3): 7.08-7.38 (m, 16Η, H-arom.); 7.40-7.54 (m, 2Η, H-aroma); 7.66-7.78 (m, 1H, H-arom.); 8.10-8.24 (m, 1H, H-arom.). 13 C-NMR (CDCl 3): 71.04 (C); 112.18.
SK 284216 Β6SK 284216-6
118,04, 125,96, 126,04, 127,04, 128,20, 128,51, 134,43 (CH-arom.); 124,22, 143,77, 154,80, 155,02, 158,01, 177,90 (C-arom.).118.04, 125.96, 126.04, 127.04, 128.20, 128.51, 134.43 (CH-arom.); 124.22, 143.77, 154.80, 155.02, 158.01, 177.90 (C-arom.).
Výťažok: 86 %. T. t.: 225-226 °C.Yield: 86%. Mp: 225-226 ° C.
Príklad 32Example 32
N-(( 1,3 -Benzodioxol-5 -yl)-metyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN - ((1,3-Benzodioxol-5-yl) methyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z pipcronylamínu.It was prepared in an analogous manner to that of Example 1 from pipcronylamine.
‘H-NMR (CDClj): 4,58 (d, 2H, CH2); 5,97 (s, 2H, CH2); 6,80-6,90 (m, 3H, H-arom.); 7,19 (s, IH, H-arom); 7,40-8,26 (m, 4H, H-arom.). 13C-NMR (CDClj): 43,87, 77,03 (CHJ; 101,24, 108,52, 108,63, 112,41, 117,99, 121,54, 125,96, 126,18, 134,45 (C-arom.).1 H-NMR (CDCl 3): 4.58 (d, 2H, CH 2 ); 5.97 (s, 2H, CH2); 6.80-6.90 (m, 3H, H-arom.); 7.19 (s, 1H, H-aroma); 7.40-8.26 (m, 4H, H-arom.). 13 C-NMR (CDCl 3): 43.87, 77.03 (CHJ; 101.24, 108.52, 108.63, 112.41, 117.99, 121.54, 125.96, 126.18, 134.45 (C-arom.).
Výťažok: 74 %. T. t.; 221-223 °C.Yield: 74%. T. t .; Mp 221-223 ° C.
Príklad 33Example 33
N,N-Di-(fcnylmetyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN, N-Di- (phenylmethyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z dibenzylamínu.It was prepared in a manner analogous to Example 1 from dibenzylamine.
'H-NMR (CDClj): 4,50 (s, 2H, CHJ; 4,67 (s, 2H, CHJ; 6,68 (s, IH, H-3); 7,15-7,42 (m, 12H, H-arom); 7,55-7,67 (m, IH, H-arom.); 8,11-8,18 (m, IH, H-arom.). 13C-NMR (CDClj: 47,76, 50,95 (CHJ; 111,89, 117,99, 125,64, 125,71, 127,50, 127,88, 128,01, 128,47, 128,77, 128,84,1 H-NMR (CDCl 3): 4.50 (s, 2H, CHJ; 4.67 (s, 2H, CHJ); 6.68 (s, 1H, H-3); 7.15-7.42 (m 12H, H-arom., 7.55-7.67 (m, 1H, H-arom.), 8.11-8.18 (m, 1H, H-arom.) 13 C-NMR (CDCl 3). : 47.76, 50.95 (CHJ; 111.89, 117.99, 125.64, 125.71, 127.50, 127.88, 128.01, 128.47, 128.77, 128.84) .
134,21 (CH-arom.); 124,13, 135,10, 135,55, 155,37,134.21 (CH-arom.); 124.13, 135.10, 135.55, 155.37,
158,17, 162,89, 177,24 (C-arom.).158.17, 162.89, 177.24 (C-arom.).
Výťažok: 85 %. T. t.: 75-78 °C.Yield: 85%. Mp: 75-78 ° C.
Príklad 34Example 34
N,N-bis((Di-2,4-dimetoxyfenyl)-metyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN, N-bis ((Di-2,4-dimethoxyphenyl) methyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z di-2,4-dimetoxybenzylamínu.Prepared in analogy to Example 1 from di-2,4-dimethoxybenzylamine.
‘H-NMR (CDClj): 3,67 (s, 3H, CH,); 3,80 (s, 6H, 2xCHJ; 3,82 (s, 3H, CHj); 4,51 (s, 2H, CHJ; 4,61 (s, 2H, CHJ; 6,32-6,55 (m, 4H, H-arom); 7,00-8,22 (m, 7H, H-arom.). 13C-NMR (CDClj): 42,72, 47,23 (CHJ; 55,01, 55,18, 55,30 (CHJ; 98,34, 103,78, 104,13, 111,19, 118,15, 125,48, 125,63, 129,66, 130,86, 134,04 (CH-arom.); 116,11, 116,57, 124,20, 155,80, 158,85, 160,53, 160,70, 163,10, 177,66 (C-arom.).1 H-NMR (CDCl 3): 3.67 (s, 3H, CH 3); 3.80 (s, 6H, 2xCHJ; 3.82 (s, 3H, CH3); 4.51 (s, 2H, CHJ; 4.61 (s, 2H, CHJ); 6.32-6.55 (m) 7.00-8.22 (m, 7H, H-arom.) 13 C-NMR (CDCl 3): 42.72, 47.23 (CH 3; 55.01, 55, 18, 55.30 (CHJ; 98.34, 103.78, 104.13, 111.19, 118.15, 125.48, 125.63, 129.66, 130.86, 134.04 (CH-) 116.11, 116.57, 124.20, 155.80, 158.85, 160.53, 160.70, 163.10, 177.66 (C-arom.).
Výťažok: 88 %. T. t.: 115-118 °C.Yield: 88%. Mp: 115-118 ° C.
Príklad 35Example 35
N-Cyklohexyl-N-fenyl-4-oxo-4H-1 -benzopyrán-2-karboxamidN-Cyclohexyl-N-phenyl-4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z cyklohexylfenylamínu.Prepared in a manner analogous to Example 1 from cyclohexylphenylamine.
'H-NMR (CDClj): 1,15- 2,32 (m, 10H, 5xCHJ; 4,80-5,00 (m, IH, CH); 6,79 (s, IH, H-3); 7,28-7,65 (m, 7H, H-arom); 7,75-7,87 (m, IH, H-arom.); 8,25-8,35 (m, IH, H-arom.). 13C-NMR (CDClj): 24,94, 25,43, 30,85 (CHJ; 55,98 (CH); 112,34, 117,50, 125,14, 128,32, 128,87, 129,50, 133,73 (CH-arom.); 123,51, 137,64, 154,90, 158,39, 161,15, 177,32 (C-arom.).1 H-NMR (CDCl 3): 1.15-2.32 (m, 10H, 5xCH 3; 4.80-5.00 (m, 1H, CH); 6.79 (s, 1H, H-3); 7.28-7.65 (m, 1H, H-aroma) 7.75-7.87 (m, 1H, H-aroma) 8.25-8.35 (m, 1H, H-aroma) @ 13 C-NMR (CDCl3): .delta. 87, 129.50, 133.73 (CH-arom.); 123.51, 137.64, 154.90, 158.39, 161.15, 177.32 (C-arom.).
Výťažok: 69 %. T. t.: 135-136 °C.Yield: 69%. Mp: 135-136 ° C.
Príklad 36Example 36
N-(4-Cyklohexylfenyl)-4-oxo-4H-l-benzopyrán-2-karboxamidN- (4-cyclohexylphenyl) -4-oxo-4H-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z (4-cyklohexyl)-fenylamínu.Prepared in analogy to Example 1 from (4-cyclohexyl) -phenylamine.
'H-NMR (CDClj): 1,25-1,60 (m, 6H, 3xCHJ; 1,70-1,95 (m, 4H, 2xCHJ; 2,45-2,60 (m, IH, CH); 7,20-8,50 (m, 9H,1 H-NMR (CDCl 3): 1.25-1.60 (m, 6H, 3xCH 3; 1.70-1.95 (m, 4H, 2xCH 3; 2.45-2.60 (m, 1H, CH)) 7.20-8.50 (m, 9H,
H-arom). 13C-NMR (CDClj: 26,10, 26,84, 34,44 (CHJ; 44,11 (CH); 112,60, 118,02, 120,53, 126,13, 126,26, 127,60, 134,61 (CH-arom.); 120,43, 124,38, 133,97, 145,86,154,66, 155,34,156,77, 177,97 (C-arom., C=O). Výťažok: 73 %. T. t: 214-216 °CH arom). 13 C-NMR (CDCl 3): 26.10, 26.84, 34.44 (CH 3; 44.11 (CH); 112.60, 118.02, 120.53, 126.13, 126.26, 127, 60, 134.61 (CH-arom.); 120.43, 124.38, 133.97, 145.86, 154.66, 155.34.156.77, 177.97 (C-arom., C = O). Yield: 73%, mp 214-216 ° C
Príklad 37Example 37
N-(2,4-Dichlorfenyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN- (2,4-Dichlorophenyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 2,4-dichlórfenylamínu.Prepared in analogy to Example 1 from 2,4-dichlorophenylamine.
'H-NMR (CDClj): 6,79-6,97 (m, 2H, H-arom.); 7,12 (s, IH, H-3); 7,38-7,49 (m, 2H, H-arom); 7,67-7,79 (m, IH, H-arom.); 7,98-8,14 (m, IH, H-arom ); 8,18-8,26 (m, IH, H-arom.).1 H-NMR (CDCl 3): 6.79-6.97 (m, 2H, H-arom.); 7.12 (s, 1H, H-3); 7.38-7.49 (m, 2H, H-aroma); 7.67-7.79 (m, 1H, H-arom.); 7.98-8.14 (m, 1H, H-aroma); 8.18-8.26 (m, 1H, H-arom.).
Analýza pre C16H;C12NOjAnalysis for C 16 H 12 Cl 2 NO 3
Výťažok: 57 %. T. t.: 156-160 °C.Yield: 57%. Mp: 156-160 ° C.
Príklad 38Example 38
N-(2,6-Dichlorfenyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN- (2,6-Dichlorophenyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 2,6-dichlórfenylamínu.Prepared in analogy to Example 1 from 2,6-dichlorophenylamine.
’H-NMR (CDClj): 6,81-7,05 (m, 2H, H-arom.); 7,15 (s, IH, H-3); 7,22-7,77 (m, 3H, H-arom); 7,84-8,10 (m, IH, H-arom.); 8,16-8,26 (m, IH, H-arom.).1 H-NMR (CDCl 3): 6.81-7.05 (m, 2H, H-arom.); 7.15 (s, 1H, H-3); 7.22-7.77 (m, 3H, H-aroma); 7.84-8.10 (m, 1H, H-arom.); 8.16-8.26 (m, 1H, H-arom.).
Analýza pre C16H9C12NO3 Analysis for C 16 H 9 Cl 2 NO 3
Výťažok: 59 %. T. t.: 134-136 °C.Yield: 59%. Mp: 134-136 ° C.
Príklad 39Example 39
N-(2,4-Difluorfenyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN- (2,4-Difluorophenyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 2,4-difluórfenylamínu.Prepared in analogy to Example 1 from 2,4-difluorophenylamine.
'H-NMR (CDClj): 6,45 (br.s., IH, NH); 6,59-6,88 (m, 2H, H-arom.); 7,13 (s, IH, H-3); 7,42-7.53 (m, 2H, H-arom);1 H-NMR (CDCl 3): 6.45 (br.s., 1H, NH); 6.59-6.88 (m, 2H, H-arom.); 7.13 (s, 1H, H-3); 7.42-7.53 (m, 2H, H-aroma);
7,68-7,74 (m, IH, H-arom.); 8,01-8,07 (m, IH, H-arom.);7.68-7.74 (m, 1H, H-arom.); 8.01-8.07 (m, 1H, H-arom.);
8,20-8,28 (m, IH, H-arom.).8.20-8.28 (m, 1H, H-arom.).
Analýza pre C1ďH9F2NOjAnalysis for C 9 H 1 d 2 F NOJ
Výťažok: 75 %. T. t.: nad 300 °C.Yield: 75%. Mp: above 300 ° C.
Príklad 40Example 40
N-(2,6-Difluorfenyl)-4-oxo-4H-l-benzopyrán-2-karboxamidN- (2,6-difluorophenyl) -4-oxo-4H-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 2,6-difluórfenylaminu.Prepared in analogy to Example 1 from 2,6-difluorophenylamine.
'H-NMR (CDClj): 7,12 (s, IH, H-3); 6,90-8,25 (m, 8H, H-arom); 10,27 (br.s., IH, NH). I3C-NMR (CDClj: 116,77 (C-3); (CH); (C); 154,67, 161,63 (C=O).1 H-NMR (CDCl 3): 7.12 (s, 1H, H-3); 6.90-8.25 (m, 8H, H-aroma); 10.27 (br.s., 1H, NH). 13 C-NMR (CDCl 3): 116.77 (C-3); (CH); (C); 154.67, 161.63 (C = O).
Analýza pre C16H9F2NO3 Analysis for C 16 H 9 F 2 NO 3
Výťažok: 67 %. T. t: nad 300 °C.Yield: 67%. Mp: above 300 ° C.
SK 284216 Β6SK 284216-6
Príklad 41Example 41
N-(2,6-Dimetylfenyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN- (2,6-Dimethylphenyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 2,6-dimetylfenylamínu.Prepared in analogy to Example 1 from 2,6-dimethylphenylamine.
'H-NMR (CDClj): 2,39 (s, 6H, 2xCH3); 6,99-7,13 (m, 3H, H-arom.); 7,21 (s, IH, H-3); 7,47-7,58 (m, 2H, H-arom);1 H-NMR (CDCl 3): 2.39 (s, 6H, 2xCH 3 ); 6.99-7.13 (m, 3H, H-arom.); 7.21 (s, 1H, H-3); 7.47-7.58 (m, 2H, H-aroma);
7,69-7,72 (m, IH, H-arom.); 8,19-8,27 (m, IH, H-arom.).7.69-7.72 (m, 1H, H-arom.); 8.19-8.27 (m, 1H, H-arom.).
Analýza pre Ci8H|5NO3 Analysis for C 8 H | 5 NO 3
Výťažok: 67 %. T. t.: 166-168 °C.Yield: 67%. Mp: 166-168 ° C.
Príklad 42Example 42
N-(2-Trifluormetylfenyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN- (2-Trifluoromethylphenyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 2-trifluórmetylfenyl-amínu.Prepared in analogy to Example 1 from 2-trifluoromethylphenylamine.
'H-NMR (CDClj): 6,99-7,66 (m, 7H, H-arom.); 7,69-7,72 (m, IH, H-arom.); 8,19-8,27 (m, IH, H-arom.).1 H-NMR (CDCl 3): 6.99-7.66 (m, 7H, H-arom.); 7.69-7.72 (m, 1H, H-arom.); 8.19-8.27 (m, 1H, H-arom.).
Analýza pre C17H10FjNOjAnalysis for C 17 H 10 F 3 NO 3
Výťažok: 65%. T. t.: 121-123 °C.Yield: 65%. Mp: 121-123 ° C.
Príklad 43Example 43
N-(4-Trifluormetylfenyl)-4-oxo-4H-l-benzopyrán-2-karboxamidN- (4-trifluoromethylphenyl) -4-oxo-4H-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 4-trifluórmetylfenyl-amínu.Prepared in analogy to Example 1 from 4-trifluoromethylphenylamine.
‘H-NMR (CDClj): 6,93-7,67 (m, 7H, H-arom.); 7,72-7,78 (m, IH, H-arom.); 8,14-8,22 (m, IH, H-arom.).1 H-NMR (CDCl 3): 6.93-7.67 (m, 7H, H-arom.); 7.72-7.78 (m, 1H, H-arom.); 8.14-8.22 (m, 1H, H-arom.).
Analýza pre C|7H10FjNOjAnalysis for C 17 H 10 F 3 NO 3
Výťažok: 56 %. T. t.: 129-133 °C.Yield: 56%. Mp: 129-133 ° C.
Príklad 44Example 44
N-(2,6-Di-(l-mctylctyl)-fenyl)-4-oxo-4H-l-benzopyrán-2-karboxamidN- (2,6-di (l-mctylctyl) phenyl) -4-oxo-4H-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 2,6-di-(l-metyletyl)fenylamínu.Prepared in analogy to Example 1 from 2,6-di- (1-methylethyl) phenylamine.
'H-NMR (CDClj): 1,24 (d, 12H, 4xCHj); 3,10 (hept., 2H, 2xCH); 7,20-8,27 (m, 8H, H-arom). 13C-NMR (CDClj): 23,63 (CHj); 29,03 (CH); 112,69, 118,16, 123,78, 126,08,1 H-NMR (CDCl 3): 1.24 (d, 12H, 4xCH 3); 3.10 (hept., 2H, 2xCH); 7.20-8.27 (m, 8H, H-aroma). 13 C-NMR (CDCl 3): 23.63 (CH 3); 29.03 (CH); 112.69, 118.16, 123.78, 126.08,
126,18, 129,08, 134,58 (CH-arom.); 124,45, 129,46, 146,10, 154,80, 155,35, 158,72, 178,00 (C-arom., C=O).126.18, 129.08, 134.58 (CH-arom.); 124.45, 129.46, 146.10, 154.80, 155.35, 158.72, 178.00 (C-arom., C = O).
Analýza pre C22H23NO3 Analysis for C 22 H 23 NO 3
Výťažok: 64 %. T. t.: 200-202 °C.Yield: 64%. Mp: 200-202 ° C.
Príklad 45Example 45
N-(2,5-Di-(2-metylprop-2-yl)-fenyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN- (2,5-Di- (2-methylprop-2-yl) phenyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z2,5-di-(2-metylprop-2-yl)-fenylamínu.Prepared in a manner analogous to Example 1 from 2,5-di- (2-methylprop-2-yl) -phenylamine.
'H-NMR (CDClj): 1,30 (s, 9H, 3xCH3); 1,51 (s, 9H, 3xCHj); 7,15-8,27 (m, 8H, H-arom). I3C-NMR (CDClj): 30,33, 30,66 (2x3xCH3); 111,79, 117,60, 123,23, 123,51, 125,55, 126,10, 134,20 (CH-arom.); 123,87, 133,40,1 H-NMR (CDCl 3): 1.30 (s, 9H, 3xCH 3 ); 1.51 (s, 9H, 3xCH3); 7.15-8.27 (m, 8H, H-aroma). 13 C-NMR (CDCl 3): 30.33, 30.66 (2x3xCH 3 ); 111.79, 117.60, 123.23, 123.51, 125.55, 126.10, 134.20 (CH-arom.); 123.87, 133.40,
139,06, 149,49, 154,70, 154,87, 156,86, 170,28, 170,39, 177,34 (C-arom, C=O).139.06, 149.49, 154.70, 154.87, 156.86, 170.28, 170.39, 177.34 (C-arom, C = O).
Analýza pre C24H27NOJAnalysis for C24H27NOJ
Výťažok: 71 %. T. t.: 176-179 °C.Yield: 71%. Mp: 176-179 ° C.
Príklad 46Example 46
N-((2-Fenyl)-fenyl)-4-oxo-4H-l-benzopyrán-2-karboxamidN - ((2-phenyl) phenyl) -4-oxo-4H-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 2-aminobifenylu.Prepared in analogy to Example 1 from 2-aminobiphenyl.
‘H-NMR (CDClj): 7,00-7,76 (m, 12H, H-arom.); 8,16-8,25 (m, IH, H-arom); 8,62-8,68 (m, IH, H-arom.); 8,97 (br.s, IH, NH). 13C-NMR (CDClj): 112,24 (C-3); 117,65, 120,22, 125,14, 125,97, 128,33, 128,86, 129,12, 129,36, 129,55, 134,52 (CH-arom.); 124,13, 132,26, 133,71, 154,42, 154,88,156,26, 177,89 (C-arom., C=O).1 H-NMR (CDCl 3): 7.00-7.76 (m, 12H, H-arom.); 8.16-8.25 (m, 1H, H-aroma); 8.62-8.68 (m, 1H, H-arom.); 8.97 (br. S, 1H, NH). 13 C-NMR (CDCl 3): 112.24 (C-3); 117.65, 120.22, 125.14, 125.97, 128.33, 128.86, 129.12, 129.36, 129.55, 134.52 (CH-arom.); 124.13, 132.26, 133.71, 154.42, 154.88, 156.26, 177.89 (C-arom., C = O).
Anal^zajrreCjjHjjNOj.Anal ^ zajrreCjjHjjNOj.
Výťažok: 77 %. T. t.: 156-157 °C.Yield: 77%. Mp: 156-157 ° C.
Príklad 47Example 47
N-(2,4,6-Trimetoxyfenyl)-4-oxo-4H-l-benzopyrán-2-karboxamidN- (2,4,6-trimethoxyphenyl) -4-oxo-4H-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 2,4,6-trimetoxyfenyl-amínu.Prepared in analogy to Example 1 from 2,4,6-trimethoxyphenylamine.
'H-NMR (CDClj): 3,56 (s, 9H, 3xCH3); 6,15-6,28 (s, 2H, H-arom.); 7,18 (s, IH, H-3); 7,45-7,57 (m, 2H, H-arom);1 H-NMR (CDCl 3): 3.56 (s, 9H, 3xCH 3 ); 6.15-6.28 (s, 2H, H-arom.); 7.18 (s, 1H, H-3); 7.45-7.57 (m, 2H, H-aroma);
7,69-7,75 (m, IH, H-arom.); 8,22-8,28 (m, IH, H-arom.).7.69-7.75 (m, 1H, H-arom.); 8.22-8.28 (m, 1H, H-arom.).
Analýza pre CiqH|7NO3 Anal 7 NO 3
Výťažok: 69 %. T. t.: 227-231 °C.Yield: 69%. Mp: 227-231 ° C.
Príklad 48Example 48
N-(2,4,6-Tri-(2-metylprop-2-yl)-fenyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN- (2,4,6-Tri- (2-methylprop-2-yl) phenyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 2,4,6-tri(2-metylprop-2-yl)-fenylamínu.Prepared in analogy to Example 1 from 2,4,6-tri (2-methylprop-2-yl) -phenylamine.
'H-NMR (CDClj): 1,56 (d, 3H, CHj); 1,98 (d, 6H, 2xCH3); 3,61-3,90 (m, 3H, 3xCH); 7,08 (s, IH, H-3); 7,22 (s, 2H, H-arom.); 7,43-7,55 (m, 2H, H-arom); 7,67-7,76 (m, IH, H-arom.); 8,19-8,26 (m, IH, H-arom.).1 H-NMR (CDCl 3): 1.56 (d, 3H, CH 3); 1.98 (d, 6 H, 2 x CH 3); 3.61-3.90 (m, 3H, 3 * CH); 7.08 (s, 1H, H-3); 7.22 (s, 2H, H-arom.); 7.43-7.55 (m, 2H, H-aroma); 7.67-7.76 (m, 1H, H-arom.); 8.19-8.26 (m, 1H, H-arom.).
Analýza pre C28H35NOjAnalysis for C 28 H 35 NO 3
Výťažok: 78%. T. t.: 108-111 °C.Yield: 78%. Mp: 108-111 ° C.
Príklad 49Example 49
N-(2-Pyridyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN- (2-Pyridyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 2-aminopyridínu.Prepared in analogy to Example 1 from 2-aminopyridine.
'H-NMR (CDClj): 7,21 (s, IH, H-3); 7,45-8,11 (m, 7H, H-arom.); 8,19-8,27 (m, IH, H-arom.).1 H-NMR (CDCl 3): 7.21 (s, 1H, H-3); 7.45-8.11 (m, 7H, H-arom.); 8.19-8.27 (m, 1H, H-arom.).
Analýza pre CnHQN2O'Analysis for C 11 H 12 N 2 O '
Výťažok: 73 %. T. t.: 234-235 °C.Yield: 73%. Mp: 234-235 ° C.
Príklad 50Example 50
N-(3-Pyridyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN- (3-Pyridyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 3-aminopyridínu.Prepared in analogy to Example 1 from 3-aminopyridine.
‘H-NMR (CDCIj): 7,16 (s, 1H, H-3); 7,30-8,20 (m, 8H, Harom.).1 H-NMR (CDCl 3): 7.16 (s, 1H, H-3); 7.30-8.20 (m, 8H, Harom).
Analýza pre C15H9N2O3Analysis for C15H9N2O3
Výťažok: 80 %. T. t.: 230-232 °C.Yield: 80%. Mp: 230-232 ° C.
Príklad 51Example 51
N-(4-Pyridyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN- (4-Pyridyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 4-aminopyridínu.Prepared in analogy to Example 1 from 4-aminopyridine.
'H-NMR (CDCIj): 7,09 (s, 1H, H-3); 7,37-8,00 (m, 7H, H-arom.); 8,19-8,27 (m, 1H, H-arom.).1 H-NMR (CDCl 3): 7.09 (s, 1H, H-3); 7.37-8.00 (m, 7H, H-arom.); 8.19-8.27 (m, 1H, H-arom.).
Analýza pre C15H9N20jAnalysis for C 15 H 9 N 2 O 3
Výťažok: 65 %. T. t.: 251-252 °C.Yield: 65%. Mp: 251-252 ° C.
Príklad 52Example 52
N-( 1 -N aftyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN- (1-N-ethyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 1-aminonaftalénu.Prepared in analogy to Example 1 from 1-aminonaphthalene.
'H-NMR (CDCIj): 7,05-8,05 (m, 11H, H-arom.); 8,17-8,25 (m, 1H, H-arom ).1 H-NMR (CDCl 3): 7.05-8.05 (m, 11H, H-arom.); 8.17-8.25 (m, 1H, H-aroma).
Anal^za^re CzqH.jNOjAnal
Výťažok: 57 %. T. t.: 146-148 °C.Yield: 57%. Mp: 146-148 ° C.
Príklad 53Example 53
N-(2-Naftyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN- (2-Naphthyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 2-aminonaftalénu.Prepared in a manner analogous to Example 1 from 2-aminonaphthalene.
'H-NMR (CDCIj): 6,95-8,03 (m, 10H, H-arom.); 8,03-8,25 (m, 2H, H-arom ).1 H-NMR (CDCl 3): 6.95-8.03 (m, 10H, H-arom.); 8.03-8.25 (m, 2H, H-aroma).
Analýza pre C^HuNOjAnalysis for C ^ HuHNONO
Výťažok: 61 %. T. t.: 137-139 °C.Yield: 61%. Mp: 137-139 ° C.
Príklad 54Example 54
N-((4 ’-N itro)-4-fenoxy-fenyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN - ((4'-Itro) -4-phenoxy-phenyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z 4’-nitrofenoxy-4-fenylamínu.It was prepared in a manner analogous to Example 1 from 4 ' -nitrophenoxy-4-phenylamine.
'H-NMR (DMSO-d6): 6,99 (s, 1H, H-3); 7,04-8,30 (m, 12H, H-arom.). 13C-NMR (DMSO-d6): 111,04, 116,88, 117,17, 118,94, 120,74, 121,35, 122,96, 123,59, 124,81, 126,06, 134,82, 134,91, 142,16, 150,76, 155,06, 155,47, 157,64, 162,85, 177,14 (C-arom., C=O).1 H-NMR (DMSO-d 6 ): 6.99 (s, 1H, H-3); 7.04-8.30 (m, 12H, H-arom.). 13 C-NMR (DMSO-d 6 ): 111.04, 116.88, 117.17, 118.94, 120.74, 121.35, 122.96, 123.59, 124.81, 126.06 , 134.82, 134.91, 142.16, 150.76, 155.06, 155.47, 157.64, 162.85, 177.14 (C-arom., C = O).
Príklad 55Example 55
N-((4'-Amino)-4-fenoxy-fenyl)-4-oxo-4H-1 -benzopyrán-2-karboxamidN - ((4'-Amino) -4-phenoxyphenyl) -4-oxo-4H-1-benzopyran-2-carboxamide
Suspenzia zlúčeniny 54 (lg) a paládium na aktívnom uhlí (0.1 g 10%) sa mieša v 20 ml metanolu pod atmosférou vodíka (atmosférický tlak) 12 hodín pri laboratórnej teplote. K reakčnej zmesi sa potom pridá etylacetát na rozpustenie produktu, a katalyzátor sa odfiltruje a roztok sa zahustí. Produkt sa získa chromatografiou na stĺpci silikagélu s eluentom zmesou etylacetát a hexán.A suspension of compound 54 (1g) and palladium on activated carbon (0.1 g 10%) was stirred in 20 mL of methanol under an atmosphere of hydrogen (atmospheric pressure) for 12 hours at room temperature. Ethyl acetate was then added to the reaction mixture to dissolve the product, and the catalyst was filtered off and the solution was concentrated. The product was obtained by column chromatography on silica gel with ethyl acetate / hexane.
'H-NMR (DMSO-d6): 7,02 (s, 1H, H-3); 7,05-8,27 (m, 12H, H-arom.). I3C-NMR (DMSO-d6): 115,08, 116,98, 117,10, 118,87, 120,56, 123,00, 123,57, 124,67, 126,05, 134,89, 142,09, 150,68, 155,03, 155,35, 157,59, 162,09, 177,35 (C-arom., C=O).1 H-NMR (DMSO-d 6 ): 7.02 (s, 1H, H-3); 7.05-8.27 (m, 12H, H-arom.). 13 C-NMR (DMSO-d 6 ): 115.08, 116.98, 117.10, 118.87, 120.56, 123.00, 123.57, 124.67, 126.05, 134.89 , 142.09, 150.68, 155.03, 155.35, 157.59, 162.09, 177.35 (C-arom., C = O).
Analýza pre C22Hi6N2O4 Analysis for C 22 H 6 N 2 O 4
Výťažok: 85 %. T. t.: 109-113 °C.Yield: 85%. Mp: 109-113 ° C.
Príklad 56Example 56
N,N-Difenyl-4-oxo-4H-1 -benzopyrán-2-karboxamidN, N-Diphenyl-4-oxo-4H-1-benzopyran-2-carboxamide
Bol pripravený analogickým postupom ako v príklade 1 z difenylamínu.It was prepared in analogy to Example 1 from diphenylamine.
'H-NMR (CDCIj): 7,18 (s, 1H, H-3); 7,22-7,70 (m, 13H, H-arom); 8,19-8,27 (m, 1H, H-arom.).1 H-NMR (CDCl 3): 7.18 (s, 1H, H-3); 7.22-7.70 (m, 13H, H-aroma); 8.19-8.27 (m, 1H, H-arom.).
Analýza pre C22HI5NOjAnalysis for C 22 H 15 NO 3
Výťažok: 87 %. T. t.: 215-217 °C.Yield: 87%. Mp: 215-217 ° C.
Biologická účinnosť látok sa hodnotí inhibíciou špecifickej aktivity acyl CoA: cholesterol acyltransferázy (ACAT) in vitro. Zdrojom enzýmu bola mikrozomálna frakcia buniek pečene potkanov a mukózy tenkého čreva králikov, ktoré boli kŕmené cholesterolom. Enzýmová reakcia prebiehala so substrátmi exogénnym oleoyl koenzýmom A a endogénnym cholesterolom. Sledovala sa konverzia 14C-oleoyl koenzýmu A na l4C-cholesteryl oleát. Cholesteryl oleát bol zo zmesi extrahovaných lipidov separovaný tenkovrstvovou chromatografiou a kvantifikovaný rádiometricky. Špecifická aktivita ACAT bola vyjadrená množstvom cholesteryl oleátu za minútu na mg mikrozomálnych bielkovín.The biological activity of the compounds is evaluated by inhibiting the specific activity of acyl CoA: cholesterol acyltransferase (ACAT) in vitro. The enzyme source was the microsomal fraction of rat liver cells and small intestine mucosa of rabbits that were fed with cholesterol. The enzyme reaction was carried out with substrates exogenous oleoyl coenzyme A and endogenous cholesterol. The conversion of 14 C-oleoyl coenzyme A to 14 C-cholesteryl oleate was monitored. Cholesteryl oleate was separated from the extracted lipid mixture by thin layer chromatography and quantified by radiometric analysis. The specific activity of ACAT was expressed as the amount of cholesteryl oleate per minute per mg of microsomal proteins.
V tabuľke 1 sú uvedené percentá inhibície aktivity ACAT v pečeni potkana a mukóze tenkého čreva králika pri určitej koncentrácii testovaných látok. Účinnosť je vypočítaná oproti hodnote aktivity enzýmu nameranej v prítomnosti 1% dimetylsulfoxidu, ktorý bol použitý ako rozpúšťadlo látok.Table 1 shows the percent inhibition of ACAT activity in rat liver and rabbit small intestine mucosa at a certain concentration of test substances. The potency is calculated against the value of enzyme activity measured in the presence of 1% dimethylsulfoxide, which was used as the solvent of the substances.
Analýza pre €^2Η|4Ν2Ο6 Analysis for € ^ 2 Η | 4 Ν 2 Ο 5
Výťažok: 72 %. T. t.: 114-115 °C.Yield: 72%. Mp: 114-115 ° C.
Tabuľka 1Table 1
Inhibičný účinok na ACAT v pečeni potkana a mukóze tenkého čreva králika.ACAT inhibitory effect in rat liver and rabbit small intestine mucosa.
Priemyselná využiteľnosťIndustrial usability
Zlúčeniny podľa vynálezu, spôsob ich prípravy je využiteľný vo farmaceutickej výrobe pri výrobe prípravkov s inhibičným účinkom na enzým acylkoenzým A a absorciu cholersterolu pri hypercholesterolémii.The compounds of the invention, a process for their preparation, are useful in pharmaceutical manufacture in the manufacture of preparations having acyl coenzyme A inhibitory activity and cholersterol absorption in hypercholesterolemia.
Claims (3)
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WO2006094601A1 (en) * | 2005-03-10 | 2006-09-14 | Merck Patent Gmbh | Chromen-4-one derivatives |
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WO2006094601A1 (en) * | 2005-03-10 | 2006-09-14 | Merck Patent Gmbh | Chromen-4-one derivatives |
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