PL211669B1 - New ionic pairs containing penicilin anion and 1-alkyl-3-carbamoilopyridine cation and methods of obtaining it - Google Patents
New ionic pairs containing penicilin anion and 1-alkyl-3-carbamoilopyridine cation and methods of obtaining itInfo
- Publication number
- PL211669B1 PL211669B1 PL384003A PL38400307A PL211669B1 PL 211669 B1 PL211669 B1 PL 211669B1 PL 384003 A PL384003 A PL 384003A PL 38400307 A PL38400307 A PL 38400307A PL 211669 B1 PL211669 B1 PL 211669B1
- Authority
- PL
- Poland
- Prior art keywords
- penicillin
- anion
- alkyl
- carbamoylpyridinium
- cation
- Prior art date
Links
- 150000001450 anions Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 150000001768 cations Chemical class 0.000 title description 3
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Natural products N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 150000002500 ions Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- -1 penicillin G anion Chemical class 0.000 claims description 9
- MIFYHUACUWQUKT-UHFFFAOYSA-N Isopenicillin N Natural products OC(=O)C1C(C)(C)SC2C(NC(=O)CCCC(N)C(O)=O)C(=O)N21 MIFYHUACUWQUKT-UHFFFAOYSA-N 0.000 claims description 5
- 229930195708 Penicillin V Natural products 0.000 claims description 5
- 229950008644 adicillin Drugs 0.000 claims description 5
- 229950008560 almecillin Drugs 0.000 claims description 5
- MIFYHUACUWQUKT-GPUHXXMPSA-N penicillin N Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2[C@H](NC(=O)CCC[C@@H](N)C(O)=O)C(=O)N21 MIFYHUACUWQUKT-GPUHXXMPSA-N 0.000 claims description 5
- QULKGELYPOJSLP-WCABBAIRSA-N penicillin O Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2[C@H](NC(=O)CSCC=C)C(=O)N21 QULKGELYPOJSLP-WCABBAIRSA-N 0.000 claims description 5
- 229940056360 penicillin g Drugs 0.000 claims description 5
- 229940056367 penicillin v Drugs 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- 238000005349 anion exchange Methods 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 229910003002 lithium salt Inorganic materials 0.000 claims description 2
- 159000000002 lithium salts Chemical class 0.000 claims description 2
- 239000003495 polar organic solvent Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229930182555 Penicillin Natural products 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 229940049954 penicillin Drugs 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LDHMAVIPBRSVRG-UHFFFAOYSA-O 1-methylnicotinamide Chemical class C[N+]1=CC=CC(C(N)=O)=C1 LDHMAVIPBRSVRG-UHFFFAOYSA-O 0.000 description 4
- 238000000160 carbon, hydrogen and nitrogen elemental analysis Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- CWRHELPIDSWOHU-UHFFFAOYSA-N 1-methylpyridin-1-ium-3-carboxamide;bromide Chemical compound [Br-].C[N+]1=CC=CC(C(N)=O)=C1 CWRHELPIDSWOHU-UHFFFAOYSA-N 0.000 description 1
- IWEIZMCTGMHCRE-UHFFFAOYSA-N 1-methylpyridin-1-ium-3-carboxamide;iodide Chemical compound [I-].C[N+]1=CC=CC(C(N)=O)=C1 IWEIZMCTGMHCRE-UHFFFAOYSA-N 0.000 description 1
- BWVDQVQUNNBTLK-UHFFFAOYSA-N 1-methylpyridin-1-ium-3-carboximidate;hydrochloride Chemical compound [Cl-].C[N+]1=CC=CC(C(N)=O)=C1 BWVDQVQUNNBTLK-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 108020004256 Beta-lactamase Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- IYNDLOXRXUOGIU-LQDWTQKMSA-M benzylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 IYNDLOXRXUOGIU-LQDWTQKMSA-M 0.000 description 1
- FCPVYOBCFFNJFS-LQDWTQKMSA-M benzylpenicillin sodium Chemical compound [Na+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 FCPVYOBCFFNJFS-LQDWTQKMSA-M 0.000 description 1
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 1
- 102000006635 beta-lactamase Human genes 0.000 description 1
- 125000003460 beta-lactamyl group Chemical group 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 210000003989 endothelium vascular Anatomy 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000002894 organic compounds Chemical group 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- ONYTXCTVWDZLFD-GITWGATASA-M potassium;(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2-prop-2-enylsulfanylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound [K+].[O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H](NC(=O)CSCC=C)C(=O)N21 ONYTXCTVWDZLFD-GITWGATASA-M 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- LFBBSWBQNQXKPF-LQDWTQKMSA-M sodium;(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound [Na+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 LFBBSWBQNQXKPF-LQDWTQKMSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000155 toxicity by organ Toxicity 0.000 description 1
- 230000007675 toxicity by organ Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000011708 vitamin B3 Substances 0.000 description 1
- 235000019160 vitamin B3 Nutrition 0.000 description 1
- 239000002132 β-lactam antibiotic Substances 0.000 description 1
- 229940124586 β-lactam antibiotics Drugs 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku są nowe pary jonowe 1-alkilo-3-karbamoilopirydyniowe z anionem penicyliny oraz sposoby ich otrzymywaniaThe subject of the invention is new 1-alkyl-3-carbamoylpyridinium ion pairs with a penicillin anion and methods of their preparation
Penicylina to antybiotyk β-laktamowy zawierający pierścień tiozolidynowy sprzężony z pierścieniem beta laktamowym. Od roku 1938, za sprawą A. Fleming'a, H. W. Florey'a i E. B. Chain'a, jest znana struktura penicyliny. Na rynku jako lek jest od 1939 roku. Podstawowymi zaletami penicyliny są niska toksyczność narządowa, szerokie spektrum działania wobec bakterii przy wysokiej skuteczności działania, dobra penetracja do narządów i tkanek również w stanie zapalnym. Natomiast wadami jest znaczna wrażliwość na β-laktamazy, szybka eliminacja z ustroju, dlatego konieczne jest częste dawkowanie a także możliwość wystąpienia alergii. Mechanizm bakteriobójczego działania jest dobrze rozpoznany.Penicillin is a β-lactam antibiotic that contains a thiozolidine ring fused to the beta lactam ring. Since 1938, the structure of penicillin is known thanks to A. Fleming, H. W. Florey and E. B. Chain. It has been on the market as a medicine since 1939. The main advantages of penicillin are low organ toxicity, a wide spectrum of activity against bacteria with high effectiveness, good penetration into organs and tissues, also in inflammation. On the other hand, the disadvantages are high sensitivity to β-lactamases, quick elimination from the body, therefore frequent dosing is necessary and the possibility of allergies. The mechanism of the bactericidal action is well recognized.
Sole 1-alkilo-3-karbamoilopirydyniowe są opisane w literaturze. Wielkość grupy alkilowej decyduje o właściwościach tej grupy związków. Aktywność powierzchniową i bakteriobójczą wykazują sole z grupą alkilową zawierającą od 8 do 16 atomów węgla. Obecność grupy karbamoilowej w pozycji trzy wskazuje, że są to analogi witaminy PP. Pierwszym kationem szeregu homologicznego jest kation 3-karbamoilo-1-metylopirydyniowy. Opisanym przeciw jonem może być anion chlorkowy, bromkowy, jodkowy czy OH-. W literaturze są doniesienia o działaniu przeciwzapalnym soli 3-karbamoilo-1-metylopirydyniowej w połączeniu z oddziaływaniem na śródbłonek naczyniowy. Sam kation 3-karbamoilo-1-metylopirydyniowy jest całkowicie nietoksyczny, jest jednym ze składników moczu ssaków.1-Alkyl-3-carbamoylpyridinium salts are described in the literature. The size of the alkyl group determines the properties of this group of compounds. The surface and bactericidal activity are shown by salts with an alkyl group containing 8 to 16 carbon atoms. The presence of a carbamoyl group in position three indicates that they are analogs of vitamin PP. The first cation of the homologous series is the 3-carbamoyl-1-methylpyridinium cation. The described counter ion may be chloride, bromide, iodide or OH - anions. There are reports in the literature about the anti-inflammatory effect of the 3-carbamoyl-1-methylpyridinium salt in combination with the effect on the vascular endothelium. The 3-carbamoyl-1-methylpyridinium cation itself is completely non-toxic and is one of the components of mammalian urine.
Istotą wynalazku są nowe pary jonowe 1-alkilo-3-karbamoilopirydyniowe zawierające anion penicyliny G o wzorze ogólnym 1, w którym R oznacza grupę alkilową prostołańcuchową zawierającą od 1 do 18 atomów węgla lub anion penicyliny V o wzorze ogólnym 2, w którym R oznacza grupę alkilową prostołańcuchową zawierającą od 1 do 18 atomów węgla lub anion penicyliny O o wzorze ogólnym 3, w którym R oznacza grupę alkilową prostołańcuchową zawierającą od 1 do 18 atomów węgla lub anion penicyliny N o wzorze ogólnym 4, w którym R oznacza grupę alkilową prostołańcuchową zawierającą od 1 do 18 atomów węgla oraz sposób ich otrzymywania, który polega na tym, że w środowisku wodnym lub rozpuszczalniku organicznym polarnym lub niepolarnym dokonuje się reakcji wymiany anionów pomiędzy chlorkiem 1-alkilo-3-karbamoilopirydyniowym lub bromkiem 1-alkilo-3-karbamoilopirydyniowym lub jodkiem 1-alkilo-3-karbamoilopirydyniowym lub wodorotlenkiem 1-alkilo-3-karbamoilopirydyniowym a solą sodową lub potasową lub litową penicyliny G lub penicyliny V lub penicyliny O lub penicyliny N.The subject of the invention are new 1-alkyl-3-carbamoylpyridinium ion pairs containing the penicillin G anion of the general formula 1, in which R is a straight-chain alkyl group containing from 1 to 18 carbon atoms, or the penicillin V anion of the general formula 2, in which R is the group a straight chain alkyl group containing from 1 to 18 carbon atoms or an anion of penicillin O of general formula 3 in which R is a straight chain alkyl group containing from 1 to 18 carbon atoms or an anion of penicillin N of general formula 4 in which R is a straight chain alkyl group containing from 1 to 18 carbon atoms and the method of their preparation, which consists in an anion exchange reaction between 1-alkyl-3-carbamoylpyridinium chloride or 1-alkyl-3-carbamoylpyridinium bromide or iodide in an aqueous medium or in a polar or non-polar organic solvent 1-alkyl-3-carbamoylpyridinium or 1-alkyl-3-carbamoylpyridinium hydroxide and sodium or potassium or lithium salt penicillin G or penicillin V or penicillin O or penicillin N.
Dzięki zastosowaniu rozwiązania według wynalazku uzyskano następujące efekty technicznoekonomiczne:Thanks to the solution according to the invention, the following technical and economic effects were obtained:
• syntezowano nowe pary jonowe zawierające kation 1-alkilo-3-karbamoilopirydyniowy i anion penicyliny, • są to potencjalne leki o spodziewanej niskiej interakcji z innymi lekami, że względu na swoją budowę. Jest to związek organiczny o budowie jonowej.• new ion pairs containing the 1-alkyl-3-carbamoylpyridinium cation and penicillin anion were synthesized, • these are potential drugs with the expected low interaction with other drugs due to their structure. It is an organic compound with an ionic structure.
• otrzymane pary jonowe będą bezpieczne w użyciu. Zarówno kation jak i anion jest analogiem związków występujących w środowisku naturalnym.• the resulting ion pairs will be safe to use. Both cation and anion are analogs of compounds found in the natural environment.
Sposób otrzymywania nowych par jonowych ilustrują poniższe przykłady:The method of obtaining new ion pairs is illustrated by the following examples:
P r z y k ł a d 1P r z k ł a d 1
Para jonowa - [penicylina G][3-karbamoilo-1-metylopirydyniowajIon pair - [penicillin G] [3-carbamoyl-1-methylpyridinate
0,05 mola soli potasowej penicyliny G oraz 0,052 mola chlorku 3-karbamoilo-1-metylopirydyniowego umieszczono w naczyniu reakcyjnym i rozpuszczono substraty w wodzie destylowanej. Mieszaninę reakcyjną mieszano intensywnie. Następnie odparowano wodę, a pozostałość krystalizowano z etanolu. Otrzymano kryształy o temperaturze topnienia 470-472K. Strukturę otrzymanej soli potwierdza protonowe i węglowe widmo magnetycznego rezonansu jądrowego, których opisy zamieszczono poniżej: 1H NMR (DMSO-d6) δ w ppm 9,68 (s, 1H), 9,18 (d, J = 6 Hz, 1H), 9,09 (s, 1H), 9,06 (d, J = 8 Hz, 1H), 8,79 (m, 1H), 8,24 (m, 2H), 7,30 (m, 4H), 5,35 (m, 2H), 4,42 (s, 3H), 3,90 (s, 1H); 3,55 (d, J = 5 Hz, 2H), 1,58 (s, 3H), 1,45 (s, 3H);0.05 mole of potassium penicillin G and 0.052 mole of 3-carbamoyl-1-methylpyridinium chloride were placed in a reaction vessel and the starting materials were dissolved in distilled water. The reaction mixture was stirred vigorously. The water was then evaporated and the residue was crystallized from ethanol. Crystals melting at 470-472K were obtained. The structure of the obtained salt confirms the proton and carbon nuclear magnetic resonance spectrum, the description of which is given below: 1 H NMR (DMSO-d 6) δ ppm 9.68 (s, 1H), 9.18 (d, J = 6 Hz, 1H) , 9.09 (s, 1H), 9.06 (d, J = 8Hz, 1H), 8.79 (m, 1H), 8.24 (m, 2H), 7.30 (m, 4H) , 5.35 (m, 2H), 4.42 (s, 3H), 3.90 (s, 1H); 3.55 (d, J = 5 Hz, 2H), 1.58 (s, 3H), 1.45 (s, 3H);
13C NMR (DMSO-d6) δ w ppm 173,2; 170,3; 169,9; 162,7; 147,1; 145,7; 143,1; 135,9; 133,1; 13 C NMR (DMSO-d6) δ in ppm 173.2; 170.3; 169.9; 162.7; 147.1; 145.7; 143.1; 135.9; 133.1;
128,9; 128,1; 127,3; 126,3; 74,0; 66,8; 64,3; 57,6; 48,1; 41,5; 31,2, 27,6.128.9; 128.1; 127.3; 126.3; 74.0; 66.8; 64.3; 57.6; 48.1; 41.5; 31.2, 27.6.
Czystość syntezowanej soli potwierdza wykona analiza elementarna CHN. Dla C23H26N4O5S o M = 470,54 wyliczone wartości w % C = 58,71, H = 5,57 i N = 11,91 a zmierzone C = 58,96, H =The purity of the synthesized salt is confirmed by an elemental CHN analysis. For C23H26N4O5S with M = 470.54 the calculated values in% C = 58.71, H = 5.57 and N = 11.91 and the measured C = 58.96, H =
5,69 i N = 11,88.5.69 and N = 11.88.
PL 211 669 B1PL 211 669 B1
P r z y k ł a d 2P r z k ł a d 2
Para jonowa - [penicylina V][3-karbamoilo-1-metylopirydyniowa]Ion pair - [penicillin V] [3-carbamoyl-1-methylpyridinium]
W kolbie szklanej rozpuszczono w etanolu 0,009 mola soli sodowej penicyliny V i 0,01 jodku 3-karbamoilo-1-metylopirydyniowego. Reakcję wymiany anionów prowadzono w temperaturze wrzenia rozpuszczalnika. Etanol oddestylowano, a pozostałość suszono w suszami próżniowej pod zmniejszonym ciśnieniem.In a glass flask, 0.009 mol of penicillin V sodium and 0.01 of 3-carbamoyl-1-methylpyridinium iodide were dissolved in ethanol. The anion exchange reaction was carried out at the reflux temperature of the solvent. Ethanol was distilled off and the residue was dried in vacuo under reduced pressure.
Czystość otrzymanego produktu potwierdza wykona analiza elementarna CHN. Dla C23H26N4O6S o M = 486,54 wyliczone wartości w % C = 56,78, H = 5,39 i N = 11,52 a zmierzone C = 56,99, H = 5,69 i N = 11,46.The purity of the product obtained is confirmed by an elemental CHN analysis. For C23H26N4O6S with M = 486.54, the calculated values in% C = 56.78, H = 5.39 and N = 11.52 and the measured C = 56.99, H = 5.69 and N = 11.46.
P r z y k ł a d 3P r z k ł a d 3
Para jonowa - [penicylina O][3-karbamoilo-1-metylopirydyniowa]Ion pair - [penicillin O] [3-carbamoyl-1-methylpyridinium]
W kolbie okrą g ł odennej rozpuszczono w wodzie destylowanej 0,006 mola soli potasowej penicyliny O i 0,0065 mola bromku 3-karbamoilo-1-metylopirydyniowego. Mieszaninę reakcyjną mieszano intensywnie w temperaturze 323K. Następnie wodę oddestylowano, a pozostałość suszono w suszarce próżniowej.0.006 mol of penicillin O potassium salt and 0.0065 mol of 3-carbamoyl-1-methylpyridinium bromide were dissolved in distilled water in a bottom round flask. The reaction mixture was stirred vigorously at the temperature of 323K. The water was then distilled off and the residue was dried in a vacuum oven.
Wykonana analiza elementarna CHN dla produktu C20H26N4O5S2 o M = 466,57: wartości wyliczone w % C = 51,49, H = 5,62 i N = 12,01 a zmierzone C = 51,73, H = 5,90 i N = 12,35 potwierdza czystość otrzymanego związku.Elemental CHN analysis performed for the product C20H26N4O5S2 with M = 466.57: values calculated in% C = 51.49, H = 5.62 and N = 12.01 and measured C = 51.73, H = 5.90 and N = 12.35 confirms the purity of the compound obtained.
P r z y k ł a d 4P r z k ł a d 4
Para jonowa - [penicylina N][3-karbamoilo-1-metylopirydyniowa]Ion pair - [penicillin N] [3-carbamoyl-1-methylpyridinium]
Zmieszano 0,02 mola wodorotlenku 3-karbamoilo-1-metylopirydyniowego i 0,01 mola soli sodowej penicyliny w reaktorze szklanym. Następnie dodano chloroform. Po intensywnym wymieszaniu warstwę chloroformową płukano wodą destylowaną. Chloroform oddestylowano a pozostałość suszono pod próżnią. O czystości otrzymanego produktu świadczy wykona analiza elementarna CHN. Dla C28H37N7O8S o M = 631,70, wyliczone wartości w % C = 53,24, H = 5,90 i N = 15,52 a zmierzone C = 53,60, H = 6,12 i N = 15,28.0.02 mol of 3-carbamoyl-1-methylpyridinium hydroxide and 0.01 mol of penicillin sodium were mixed in a glass reactor. Then chloroform was added. After vigorous mixing, the chloroform layer was rinsed with distilled water. Chloroform was distilled off and the residue was dried in vacuo. The purity of the obtained product is confirmed by the CHN elemental analysis. For C28H37N7O8S with M = 631.70, the calculated values in% C = 53.24, H = 5.90 and N = 15.52 and the measured C = 53.60, H = 6.12 and N = 15.28.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL384003A PL211669B1 (en) | 2007-12-10 | 2007-12-10 | New ionic pairs containing penicilin anion and 1-alkyl-3-carbamoilopyridine cation and methods of obtaining it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL384003A PL211669B1 (en) | 2007-12-10 | 2007-12-10 | New ionic pairs containing penicilin anion and 1-alkyl-3-carbamoilopyridine cation and methods of obtaining it |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL384003A1 PL384003A1 (en) | 2009-06-22 |
| PL211669B1 true PL211669B1 (en) | 2012-06-29 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL384003A PL211669B1 (en) | 2007-12-10 | 2007-12-10 | New ionic pairs containing penicilin anion and 1-alkyl-3-carbamoilopyridine cation and methods of obtaining it |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL211669B1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL233296B1 (en) * | 2017-09-18 | 2019-09-30 | Politechnika Poznanska | Phenoxy carboxylates with 1-dodecyl-3-carbamoylpyridinium cation, methods for obtaining them and application as herbicides |
-
2007
- 2007-12-10 PL PL384003A patent/PL211669B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PL384003A1 (en) | 2009-06-22 |
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| Date | Code | Title | Description |
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| LAPS | Decisions on the lapse of the protection rights |
Effective date: 20101210 |