PL144111B2 - Method of obtaining novel 2-hydroxy-4-beta-hydroxyethylamino-6-methyl-5-pyrimidylocarkoxylamides - Google Patents
Method of obtaining novel 2-hydroxy-4-beta-hydroxyethylamino-6-methyl-5-pyrimidylocarkoxylamides Download PDFInfo
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- PL144111B2 PL144111B2 PL25374685A PL25374685A PL144111B2 PL 144111 B2 PL144111 B2 PL 144111B2 PL 25374685 A PL25374685 A PL 25374685A PL 25374685 A PL25374685 A PL 25374685A PL 144111 B2 PL144111 B2 PL 144111B2
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- Prior art keywords
- hydroxy
- methyl
- hydroxyethylamino
- conhr
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 12
- -1 p-ethoxyphenyl Chemical group 0.000 claims description 11
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- GWBXDNMRCWPFHJ-UHFFFAOYSA-N CC1=C(C(N)=O)C(S)=NC(O)=N1 Chemical class CC1=C(C(N)=O)C(S)=NC(O)=N1 GWBXDNMRCWPFHJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 11
- 206010030113 Oedema Diseases 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 2
- 229960004801 imipramine Drugs 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- JGDOXDTVWVBTIO-UHFFFAOYSA-N CCOC(C=C1)=CC=C1NC(C(C(S)=N1)=C(C)N=C1O)=O Chemical compound CCOC(C=C1)=CC=C1NC(C(C(S)=N1)=C(C)N=C1O)=O JGDOXDTVWVBTIO-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 1
- BTMARYYJICQXGS-UHFFFAOYSA-N N-cyclohexyl-6-methyl-2-oxo-4-sulfanylidene-1H-pyrimidine-5-carboxamide Chemical compound N1C(=O)NC(=S)C(C(=O)NC2CCCCC2)=C1C BTMARYYJICQXGS-UHFFFAOYSA-N 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000000794 anti-serotonin Effects 0.000 description 1
- 239000003420 antiserotonin agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 229960000482 pethidine Drugs 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
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- Pyridine Compounds (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarzania nowych amidów kwasu 2-hydroksy-4-/$- hydroksyetyloamino-6-metylo-5-pirymidynokarboksylowego o wzorze ogólnym 1, w którym R oznacza reszte p-chlorofenylowa, p-etoksyfenylowa lub cykloheksylowa. Zwiazek wytworzony sposobem wedlug wynalazku jest pólproduktem do wytwarzania zwiazków wykazujacych dziala¬ nie biologiczne.Wedlug wynalazku sposób wytwarzania nowych amidów kwasu 2-hydroksy-4- /3-hydroksy- etyloamino-6-metylo-5-pirymidynokarboksylowego o wzorze ogólnym 1, w którym R oznacza reszte p-chlorofenylowa lub cykloheksylowa lub p-etoksyfenylowa, polega na tym, ze amidy kwasu 2-hydroksy-4-merkapto -6-metylo-5-pirymidynokarboksylowego o wzorze ogólnym 2, w którym R ma wyzej podane znaczenie, ogrzewa sie z etanoloamina w bezwodnej pirydynie.Zwiazek wytworzony sposobem wedlug wynalazku ogrzewany z chlorkiem tionylu w chloro¬ formie prowadzi do otrzymania amidów kwasu 2-hydroksy-4-/3-chloroetyloamino -6-metylo-5- pirymidyno-karboksylowego o wzorze ogólnym 3, w którym R oznacza reszte p-chlorofenylowa, p-etoksyfenylowa lub cykloheksylowa, które nastepnie ogrzewane w tetrahydrofuranie lub pirydy¬ nie daja nowe chlorowodorki kwasu l-H-7-metylo-5- okso-2,3-dihydroimidazo (1,2-c) pirymi- dyno-8-karboksylowego o wzorze ogólnym 4, w którym R ma wyzej podane znaczenie.Zwiazki finalne wykazuja dzialanie przeciwzapalne i przeciwbólowe. Zwiazek o wzorze 4, w którym R jest reszta cykloheksylowa badany byl w szeregu testach na osrodkowyuklad nerwowy i aktywnosc przeciwbólowa na myszach. Oznaczona toksycznosc dootrzewnowa i doustna wynosila odpowiednio 865 i 1294 mg/kg. W tescie na dzialanie przeciwserotoninowe wykazywal aktywnosc jak imipramina, w tescie na antagonizm z rezerpina wykazal 60% dzialania imipraminy, a w tescie na dzialanie przeciwagresyjne znosil agresje u 80% myszy. W tescie goracej plytki i w tescie czolgania wykazal statystycznie istotne dzialanie przeciwbólowe, porównywalne z petydyna, podawany w dawce 0,lLDso.Zwiazki o wzorze 4, w których R jest reszta p-chlorofenylowa i p-etoksyfenylowa badano na aktywnosc przeciwzapalna na modelu ostrego stanu zapalnego u szczura w tescie karageninowym.2 144 111 Preparaty podawano dozoladkowo w dawce 100 mg/kg w zawiesinach w 5% roztworze gumy arabskiej. Jako lek standardowy zastosowano aspiryne w dawce 75 mg/kg. Zwiazek o wzorze 4, gdzie R jest reszta p-chlorofenylowa w czasie czterogodzinnej obserwacji hamowal obrzek w 52,2-56,7%, a zwiazek o wzorze 4, gdzie R jest reszta p-etoksyfenylowa hamowal obrzek w 38,5-43%. Wzorcowa aspiryna hamowala obrzek w 64,2-69,5%.Przedmiot wynalazku jest przedstawiony w trzech przykladach wykonania.Przyklad I. 2g p-chlorofenyloamidu kwasu 2-hydroksy-4- merkapto -6-metylo -5-piry- midynokarboksylowego i 2,1 g etanoloaminy ogrzewa sie w 15 ml suchej pirydyny przez 4 godziny w temperaturze wrzenia. Odsacza sie na goraco 1,2g p-chlorofenyloamidu kwasu 2-hydroksy-4-/3- hydroksyetyloamino-6 -metylo-5-pirymidynokarboksylowego. Zwiazek ma temperature topnienia 338 K i otrzymuje sie go z wydajnoscia równa 52% wydajnosci teoretycznej.Przykladll. 10g p-etoksyfenyloamidu kwasu 2-hydroksy-6- metylo -4-merkapto -5- pirymidynokarboksylowego i 10 g etanoloaminy ogrzewa sie w 100 ml pirydyny przez 6 godzin w temperaturze wrzenia. Odsacza sie na goraco 6g p-etoksyfenyloamidu kwasu 2-hydroksy-4-/J -hydroksyetyloamino-6-metylo-5-pirymidynokarboksylowego. Zwiazek ma temperature topnie¬ nia 338-340 K i jest otrzymywany z wydajnoscia równa 55% wydajnosci teoretycznej.Przyklad III. 2,6g cykloheksyloamidu kwasu 2-hydroksy-4-merkapto -6-metylo-5-piry- midynokarboksylowego ogrzewa sie z 3 g etanoloaminy w 26 ml suchej pirydyny przez 6 godzin.Mieszanine przesacza sie i pozostawia do krystalizacji. Odsacza sie 2,5 g cykloheksyloamidu kwasu 2-hydroksy-4-/3-hydroksyetyloamino-6-metylo -5-pirymidynokarboksylowego. Zwiazek ma tem¬ perature topnienia 504-506 K i jest otrzymywany z wydajnoscia 68% wydajnosci teoretycznej.Zastrzezenie patentowe Sposób wytwarzania nowych amidów kwasu 2-hydroksy-4-/J- hydroksyetyloamino-6-metylo- 5-pirymidynokarboksylowego o wzorze ogólnym 1, w którym R oznacza reszte p-chlorofenylowa, p-etoksyfenylowa lub cykloheksylowa, znamienny tym, ze amidy kwasu 2-hydroksy-4-merkapto -6-metylo-5-pirymidynokarboksylowego o wzorze ogólnym 2, w którym R ma wyzej podane znaczenie, ogrzewa sie z etanoloamina w bezwodnej pirydynie.144111 HN(CH2)20H N<*s!\^C0NHR HO ^ N^ CH3 WZOR1 SH I N-,' ^ CONHR Jk HO/ TT^CHj WZÓR 2144111 N hn(ch4ci ^s^CONHR kJ H0^N/XCH5 WZiDR 3 IJJH HCl CONHR WZÓR 4 Pracownia Poligraficzna UP PRL. Naklad 100 egz.Cena 220 zl PLThe present invention relates to a process for the preparation of new 2-hydroxy-4 - [beta] -hydroxyethylamino-6-methyl-5-pyrimidinecarboxylic acid amides of the general formula I, in which R is a p-chlorophenyl, p-ethoxyphenyl or cyclohexyl residue. The compound according to the invention is an intermediate for the preparation of compounds exhibiting biological activity. According to the invention, a method for the preparation of new 2-hydroxy-4- (3-hydroxy-ethylamino-6-methyl-5-pyrimidine carboxylic acid amides of general formula I) R is a p-chlorophenyl or cyclohexyl or p-ethoxyphenyl residue, it consists in the fact that 2-hydroxy-4-mercapto -6-methyl-5-pyrimidinecarboxylic acid amides of the general formula 2, in which R is as defined above, are heated with ethanolamine in anhydrous pyridine. The compound according to the invention, heated with thionyl chloride in chloroform, gives the 2-hydroxy-4- (3-chloroethylamino-6-methyl-5-pyrimidine-carboxylic acid amides of general formula 3) wherein R is a p-chlorophenyl, p-ethoxyphenyl or cyclohexyl residue which is then heated in tetrahydrofuran or pyridine to give new hydrochlorides of 1H-7-methyl-5-oxo-2,3-dihydroimidazo (1,2-c) pyrim iDine-8-carboxylic acid of general formula IV, wherein R is as defined above. The final compounds have anti-inflammatory and analgesic activity. The compound of formula IV, wherein R is a cyclohexyl residue, has been tested in a series of tests for the CNS and analgesic activity in mice. The determined intraperitoneal and oral toxicity were 865 and 1294 mg / kg, respectively. In the anti-serotonin test, it showed activity like imipramine, in the reserpine antagonism test it showed 60% of imipramine, and in the anti-aggression test it was aggressive in 80% of mice. In the hot plate test and in the traversing test, it showed a statistically significant analgesic effect, comparable to pethidine, administered at a dose of 0.1LD50. Compounds of formula 4 in which R is a p-chlorophenyl and p-ethoxyphenyl residue were tested for anti-inflammatory activity in an acute inflammatory model in rats in the carrageenan test.2 144 111 The preparations were administered per dose at a dose of 100 mg / kg in suspensions in a 5% gum arabic solution. The standard drug used was aspirin at a dose of 75 mg / kg. The compound of formula 4, where R is a p-chlorophenyl residue, inhibited edema in 52.2-56.7% during the four-hour observation, and the compound of formula 4, where R is a p-ethoxyphenyl residue, inhibited edema in 38.5-43% . Standard aspirin inhibited edema in 64.2-69.5%. The subject of the invention is presented in three working examples. Example I. 2 g of p-chlorophenylamide 2-hydroxy-4-mercapto -6-methyl -5-pyrimidinecarboxylic acid and 2 1 g of ethanolamine is heated in 15 ml of dry pyridine for 4 hours under reflux. 1.2 g of 2-hydroxy-4- (3-hydroxyethylamino-6-methyl-5-pyrimidinecarboxylic acid) p-chlorophenylamide is filtered hot. The compound has a melting point of 338 K and is obtained in 52% of the theoretical yield. 10 g of 2-hydroxy-6-methyl-4-mercapto -5-pyrimidinecarboxylic acid p-ethoxyphenylamide and 10 g of ethanolamine are heated in 100 ml of pyridine for 6 hours under reflux. 6 g of 2-hydroxy-4- (J-hydroxyethylamino-6-methyl-5-pyrimidinecarboxylic acid p-ethoxyphenylamide) are filtered hot. The compound has a melting point of 338-340 K and is obtained in 55% of theoretical yield. 2.6 g of 2-hydroxy-4-mercapto -6-methyl-5-pyrimidinecarboxylic acid cyclohexylamide are heated with 3 g of ethanolamine in 26 ml of dry pyridine for 6 hours. The mixture is filtered and left to crystallize. 2.5 g of 2-hydroxy-4- (3-hydroxyethylamino-6-methyl -5-pyrimidinecarboxylic acid cyclohexylamide) are filtered off. The compound has a melting point of 504-506 K and is obtained with a yield of 68% of theoretical yield. Patent claim Method for the preparation of the new 2-hydroxy-4- (J-hydroxyethylamino-6-methyl-5-pyrimidine carboxylic acid amides of the general formula 1) in which R is a p-chlorophenyl, p-ethoxyphenyl or cyclohexyl residue, characterized in that 2-hydroxy-4-mercapto -6-methyl-5-pyrimidinecarboxylic acid amides of the general formula 2, in which R is as defined above, is heated with ethanolamine in anhydrous pyridine. 144 111 HN (CH2) 20H N <* s! \ ^ C0NHR HO ^ N ^ CH3 FORMULA SH I N-, '^ CONHR Jk HO / TT ^ CHj FORM 2144 111 N hn (ch4ch ^ s ^ CONHR kJ H0 ^ N / XCH5 WZiDR 3 IJJH HCl CONHR MODEL 4 Printing workshop of the Polish People's Republic. Circulation 100 copies Price PLN 220 PL
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL25374685A PL144111B2 (en) | 1985-05-30 | 1985-05-30 | Method of obtaining novel 2-hydroxy-4-beta-hydroxyethylamino-6-methyl-5-pyrimidylocarkoxylamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL25374685A PL144111B2 (en) | 1985-05-30 | 1985-05-30 | Method of obtaining novel 2-hydroxy-4-beta-hydroxyethylamino-6-methyl-5-pyrimidylocarkoxylamides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL253746A2 PL253746A2 (en) | 1987-02-23 |
| PL144111B2 true PL144111B2 (en) | 1988-04-30 |
Family
ID=20026907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL25374685A PL144111B2 (en) | 1985-05-30 | 1985-05-30 | Method of obtaining novel 2-hydroxy-4-beta-hydroxyethylamino-6-methyl-5-pyrimidylocarkoxylamides |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL144111B2 (en) |
-
1985
- 1985-05-30 PL PL25374685A patent/PL144111B2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL253746A2 (en) | 1987-02-23 |
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