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1.
Pol J Pharmacol Pharm ; 43(5): 369-79, 1991.
Article in English | MEDLINE | ID: mdl-1688093

ABSTRACT

In reactions of 1-phenyl-7-methyl-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimido[ 4,5-d]pyrimidin e (1) with 1-(3-chloropropyl)-4-methyl(phenyl, 3-chlorophenyl, 2-pyrimidynyl, 2-thiazolyl)piperazines (5), mixtures of isomeric N- and S-substituted derivatives of compound 1 (3 and 4) were obtained. Isomers were separated by fractional crystallization. The structure of novel compounds 3 and 4 was confirmed by elemental and spectral analyses. In pharmacological screening compounds 3b and 4b displayed rather strong analgesic action, inhibited amphetamine hyperactivity and abolished apomorphine stereotypy. Compounds 3e,3d and 4e attenuated m-chlorophenylpiperazine-induced hypothermia.


Subject(s)
Piperazines/chemical synthesis , Psychotropic Drugs/chemical synthesis , Pyrimidinones/chemical synthesis , Analgesics/pharmacology , Animals , Anticonvulsants/pharmacology , Antidepressive Agents/pharmacology , Antiparkinson Agents/chemical synthesis , Antiparkinson Agents/pharmacology , Antipsychotic Agents/chemical synthesis , Antipsychotic Agents/pharmacology , Apomorphine/pharmacology , Body Temperature/drug effects , Dextroamphetamine/antagonists & inhibitors , Electroshock , Female , Isomerism , Lethal Dose 50 , Male , Mice , Motor Activity/drug effects , Piperazines/pharmacology , Piperazines/toxicity , Psychotropic Drugs/pharmacology , Psychotropic Drugs/toxicity , Pyrimidinones/pharmacology , Pyrimidinones/toxicity , Rats , Rats, Inbred Strains , Stereotyped Behavior/drug effects
2.
Farmaco ; 45(1): 101-10, 1990 Jan.
Article in English | MEDLINE | ID: mdl-2337441

ABSTRACT

Condensation of diethyl 2-amino-6-methylpyridine-3,4-dicarboxylate with phenyl or cyclohexyl isocyanates gave the corresponding derivatives of ethyl 7-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrido [2,3-d]pyrimidine- 5-carboxylate[(V), (VI)]. Alkylation of (V) and (VI) afforded the corresponding N-1 substituted derivatives (XI-XIX).


Subject(s)
Pyridines/chemical synthesis , Pyrimidinones/chemical synthesis , Aggression/drug effects , Analgesics/chemical synthesis , Animals , Anti-Inflammatory Agents, Non-Steroidal/chemical synthesis , Anticonvulsants/chemical synthesis , Blood Pressure/drug effects , Lethal Dose 50 , Mice , Motor Activity/drug effects , Pyridines/pharmacology , Pyridines/toxicity , Pyrimidinones/pharmacology , Pyrimidinones/toxicity , Rats
3.
Farmaco ; 45(1): 111-21, 1990 Jan.
Article in English | MEDLINE | ID: mdl-2337442

ABSTRACT

Condensation of diethyl 2-amino-6-methylpyridine-3,4-dicarboxylate (I) with the corresponding isothiocyanates afforded derivatives of ethyl 4-oxo-2-thioxo-1,2,3,4-tetrahydropyrido [2,3-d]pyrimidine-5-carboxylate (V-VII). Alkylation of (V), (VI) and (XI) gave the corresponding derivatives of ethyl 2-alkylthio-4-oxo-3,4-(and 1,4)-dihydropyrido[2,3-d]pyrimidine-5- and -6- carboxylate [(XII-XVI), (XX-XXII)]. Some of the obtained compounds were active pharmacologically.


Subject(s)
Pyridines/chemical synthesis , Pyrimidinones/chemical synthesis , Aggression/drug effects , Analgesics , Animals , Anticonvulsants , Lethal Dose 50 , Magnetic Resonance Spectroscopy , Mice , Motor Activity/drug effects , Pyridines/pharmacology , Pyridines/toxicity , Pyrimidinones/pharmacology , Pyrimidinones/toxicity , Rats
4.
Arch Immunol Ther Exp (Warsz) ; 37(3-4): 487-97, 1989.
Article in English | MEDLINE | ID: mdl-2517913

ABSTRACT

In the reactions of ethyl 4-chloro/tosyloxy/-2-methylpyrimidine-5-carboxylate with differently substituted thioureas, new derivatives of 2,3-dihydro-7-methylpyrimido-[5,4-e]-1,3-thiazine (5-9) and of 7-methyl-1,2,3,4-tetrahydropyrimido[4,5-d]pyrimidine (12, 13) were obtained. Besides, some derivatives of 4-phenylamino-2-methylpyrimidine-5-carboxylic acid (15-20) were also synthesized. Structure of the compounds was confirmed by spectral analysis (IR, H-NMR) and chemical transformations. In the screening pharmacological examinations some of the compounds revealed analgesic, antiinflammatory and immunosuppressive activity.


Subject(s)
Pyrimidines/chemical synthesis , Thiazines/chemical synthesis , Chemical Phenomena , Chemistry , Thiourea
6.
Farmaco Sci ; 41(12): 954-63, 1986 Dec.
Article in English | MEDLINE | ID: mdl-3556569

ABSTRACT

Amides of 1-benzyl-3,7-dimethyl-4-oxo-2-thioxo-1,2,3,4- tetrahydropyrido[2,3]pyrimidine-6-carboxylic acid were obtained by the condensation of ammonia, primary and secondary cyclic amines with the corresponding acid chloride. As by - products amides of 1-benzyl-3,7-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrido[2,3-d]pyr imidine-6- carboxylic acid were isolated as a result of desulfuration. The same reaction performed with chloride of 1-butyl-7-methyl-3-phenyl-4-oxo-2-thioxo-1,2,3,4-tetrahydropyri do[2,3- d]pyrimidine-6-carboxylic acid gave mainly the corresponding 2,4-dioxo-amides.


Subject(s)
Analgesics/chemical synthesis , Pyridines/chemical synthesis , Pyrimidines/chemical synthesis , Animals , Chemical Phenomena , Chemistry , Mice , Pyridines/toxicity , Pyrimidines/toxicity
7.
Farmaco Sci ; 41(12): 964-9, 1986 Dec.
Article in English | MEDLINE | ID: mdl-3556570

ABSTRACT

It was stated that esters of 3H-2-imino-7-methyl-4-oxopyrido[3,2-e]-1,3-thiazine-5- and -6-carboxylic acids react with acyl anhydrides and chlorides giving 3-acyl derivatives. Reaction of the above mentioned esters with isocyanates affords the corresponding 3-carbamoyl derivatives.


Subject(s)
Analgesics/chemical synthesis , Pyridines/chemical synthesis , Thiazines/chemical synthesis , Animals , Chemical Phenomena , Chemistry , Lethal Dose 50 , Mice , Pyridines/pharmacology , Pyridines/toxicity , Thiazines/pharmacology , Thiazines/toxicity
8.
Farmaco Sci ; 41(10): 819-26, 1986 Oct.
Article in English | MEDLINE | ID: mdl-3792541

ABSTRACT

A rearrangement of 2H-2-acetonyl(phenacyl)-4,6-dimethyl- pyrido[3,2-d]isothiazoline-3-one-1,1-dioxides (I), (II) to derivatives of the unknown system of 2H-pyrido[3,2-e]-1,2-thiazine-1,1-dioxide (V), (XIII) is described; the synthesis of 2-N-substituted derivatives (VI - XII), (XIV - XVI) is also given. The structures of the new compounds were confirmed with elemental analyses and spectral data (I.R., N.M.R., MS). Some of the newly obtained compounds showed strong analgesic activity upon pharmacological screening.


Subject(s)
Analgesics/chemical synthesis , Pyridines/chemical synthesis , Thiazines/chemical synthesis , Analgesics/toxicity , Animals , Chemical Phenomena , Chemistry , Cyclic S-Oxides/chemical synthesis , Cyclic S-Oxides/pharmacology , Cyclic S-Oxides/toxicity , Mice , Pyridines/pharmacology , Pyridines/toxicity , Rats , Thiazines/pharmacology , Thiazines/toxicity
9.
Farmaco Sci ; 41(9): 676-83, 1986 Sep.
Article in English | MEDLINE | ID: mdl-3491004

ABSTRACT

The synthesis of 2H-4,6-dimethylpyrido[3,2-d]isothiazolin-3-one-1,1-dioxide and its 2-N-substituted derivatives are described. Structures of the obtained compounds were determined on the basis of elemental analyses and spectral data I.R., N.M.R., MS. Preliminary information on the pharmacological properties of the obtained compounds also given.


Subject(s)
Pyridines/chemical synthesis , Thiazoles/chemical synthesis , Animals , Anti-Inflammatory Agents, Non-Steroidal , Blood Pressure/drug effects , Chemical Phenomena , Chemistry , Lethal Dose 50 , Mice , Motor Activity/drug effects , Pyridines/pharmacology , Pyridines/toxicity , Rats , Thiazoles/pharmacology , Thiazoles/toxicity
11.
Farmaco Sci ; 40(1): 58-64, 1985 Jan.
Article in English | MEDLINE | ID: mdl-3979546

ABSTRACT

It was stated that esters of 3H-2-imino-7-methyl-4-oxopyrido [3,2-e]-1,3-thiazine-5- and -6-carboxylic acids (I, II) undergo the Mannich reaction giving the corresponding 3-aminomethyl derivatives (III-XIV). Derivatives of ester II [(XII) and (XIV)] showed distinct analgesic and antiserotonic activities.


Subject(s)
Analgesics/chemical synthesis , Pyridines/chemical synthesis , Serotonin Antagonists/chemical synthesis , Thiazines/chemical synthesis , Animals , Anti-Inflammatory Agents/chemical synthesis , Anticonvulsants/chemical synthesis , Carboxylic Acids/chemical synthesis , Carboxylic Acids/pharmacology , Hexobarbital/pharmacology , Magnetic Resonance Spectroscopy , Mice , Motor Activity/drug effects , Pyridines/pharmacology , Rats , Reserpine/antagonists & inhibitors , Thiazines/pharmacology
12.
Farmaco Sci ; 40(1): 65-72, 1985 Jan.
Article in English | MEDLINE | ID: mdl-3979547

ABSTRACT

It has been found that the condensation of esters of 3H-2-imino-7-methyl-4-oxopyrido[3,2-e]-1,3-thiazine-5- and -6-carboxylic acids (I, II) with formaldehyde and primary amines affords the corresponding derivatives of a new heterocyclic system pyrido[3,2-e]-1,3-thiazino [3,2-a]-s-triazine (IX-XXIV).


Subject(s)
Analgesics/chemical synthesis , Thiazines/chemical synthesis , Triazines/chemical synthesis , Animals , Anticonvulsants/chemical synthesis , Blood Pressure/drug effects , Mice , Pyridines/chemical synthesis , Pyridines/pharmacology , Rats , Reserpine/antagonists & inhibitors , Serotonin Antagonists/chemical synthesis , Thiazines/pharmacology , Triazines/pharmacology
13.
Farmaco Sci ; 37(4): 247-58, 1982 Apr.
Article in English | MEDLINE | ID: mdl-7084447

ABSTRACT

Condensation of diethyl 2-chloro-6-methylpyridine-3,5-dicarboxylate (IV) with thiourea and alkyl or alkenyl N-mono- and N,N'-disubstituted thioureas gives mainly the corresponding derivatives of ethyl 3H-2-imino-7-methyl-4-oxopyrido [3,2-e]-1,3-thiazine-6-carboxylate (VI-XII). As by-products isomeric derivatives of ethyl 7-methyl-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrido [2,3-d) pyrimidine-6-carboxylate (XIII-XVIII) are formed.


Subject(s)
Serotonin Antagonists/chemical synthesis , Thiazines/chemical synthesis , Animals , Anti-Inflammatory Agents/chemical synthesis , Anticonvulsants/chemical synthesis , Chemical Phenomena , Chemistry , Hexobarbital/pharmacology , Lethal Dose 50 , Mice , Rats , Reserpine/antagonists & inhibitors , Sleep/drug effects , Thiazines/pharmacology
14.
Farmaco Sci ; 37(4): 266-74, 1982 Apr.
Article in English | MEDLINE | ID: mdl-7084448

ABSTRACT

Condensation of dimethyl 2-chloro-6-methylpyridine-3,4-dicarboxylate with thiourea and its N-substituted derivatives is described. It has been found that depending on the kind of substituents in the starting thiourea derivatives, pyrido [3,2-e]-1,3-thiazine or pyrido [2,3-d] pyrimidine derivatives were formed.


Subject(s)
Serotonin Antagonists/chemical synthesis , Thiazines/chemical synthesis , Animals , Anti-Inflammatory Agents/chemical synthesis , Anticonvulsants/chemical synthesis , Chemical Phenomena , Chemistry , Hexobarbital/pharmacology , Lethal Dose 50 , Mice , Rats , Reserpine/antagonists & inhibitors , Sleep/drug effects , Thiazines/pharmacology
15.
Pol J Pharmacol Pharm ; 34(4): 239-46, 1982.
Article in English | MEDLINE | ID: mdl-7182845

ABSTRACT

Several new derivatives of beta-aminomethyl-gamma-(p-chlorophenyl)-gamma-hydroxybutyric acids have been obtained. The substrates, beta-aminomethyl derivatives of gamma-(p-chlorophenyl)-tetrahydrofuranone-2 1-4, were converted by the reactions of ammonolysis, aminolysis and hydrazinolysis into appropriate amides and hydrazides of beta-aminomethyl-gamma-(p-chlorophenyl)-gamma-hydroxybutyric acid. Compounds 10, 11, 16, 18, 19 and 20 show depressant activity on CNS, while compounds 6 and 8 demonstrate antiinflammatory action.


Subject(s)
Anti-Inflammatory Agents/chemical synthesis , Central Nervous System Depressants/chemical synthesis , Hydroxybutyrates/chemical synthesis , Sodium Oxybate/chemical synthesis , Animals , Chemical Phenomena , Chemistry , Mice , Sodium Oxybate/analogs & derivatives , Sodium Oxybate/pharmacology
17.
Pol J Pharmacol Pharm ; 34(4): 247-55, 1982.
Article in English | MEDLINE | ID: mdl-6820691

ABSTRACT

Several new D,L beta-aminomethyl derivatives of gamma-(p-chlorophenyl)-tetrahydrofuran-2-one have been synthesized. The derivatives of D,L beta-aminomethyl-beta-(p-chlorobenzoyl)-propionic acid 2-6 were used as the substrates. These compounds were obtained by the Mannich reaction from acid 1, cyclic secondary amines and formaldehyde. After the reduction with NaBH4, and cyclization, derivatives 2-6 were converted into the appropriate derivatives of tetrahydrofuran-2-one 9-13. Some of the obtained compounds (5, 6, 8, 11 and 12) showed depressant activity against the central nervous system.


Subject(s)
Central Nervous System Depressants/chemical synthesis , Furans/chemical synthesis , Animals , Chemical Phenomena , Chemistry , Dihydroxyphenylalanine/pharmacology , Drug Interactions , Furans/pharmacology , Furans/toxicity , Lethal Dose 50 , Mice , Motor Activity/drug effects , Pentylenetetrazole/antagonists & inhibitors
18.
Arch Immunol Ther Exp (Warsz) ; 29(6): 827-33, 1981.
Article in English | MEDLINE | ID: mdl-7349104

ABSTRACT

In the course of studies on compounds with expected antiinflammatory and immunosuppressive activity a series of new derivatives of 2-amino-4-p-chlorophenylthiazole-5-acetic acid have been synthesized. Several new and unexpected details of the chemical properties of these compounds were revealed. The chemical structure of the new compounds was confirmed by degradation and identification of the decomposition products and by spectral analysis.


Subject(s)
Anti-Inflammatory Agents , Immunosuppressive Agents , Thiazoles/chemical synthesis , Amino Acids , Anti-Inflammatory Agents/chemical synthesis , Immunosuppressive Agents/chemical synthesis
19.
Arch Immunol Ther Exp (Warsz) ; 29(6): 835-44, 1981.
Article in English | MEDLINE | ID: mdl-7349105

ABSTRACT

A number of new N-aralkylidene and N-aralkyl derivatives of amides and hydrazides of 2-amino-4-p-chlorophenylthiazole-5-acetic acid (III-XXIX) have been synthesized. These compounds were obtained in two various ways depending on the character of substituents in the carboxyl group. The chemical structure of the newly obtained compounds was determined on the basis of the data of elementary and spectral analyses.


Subject(s)
Anti-Inflammatory Agents/chemical synthesis , Thiazoles/chemical synthesis , Amino Acids , Chemical Phenomena , Chemistry , Solubility
20.
Arch Immunol Ther Exp (Warsz) ; 29(6): 845-50, 1981.
Article in English | MEDLINE | ID: mdl-7349106

ABSTRACT

In the course of the studies on compounds with expected antiinflammatory and immunosuppressive activity several new tert-amides derivatives of 2-N-aralkylamino-alpha-sulpho-2-amino-4-p-chlorophenylthiazole-5-acetic acid were synthesized. Some of the previously described Schiff bases reacted with aqueous alcoholic solution of sodium bisulphite and as a result several (III-VIII) alpha-sulphoderivatives were obtained. The course of the reactions was studied and the structure of the new compounds was confirmed.


Subject(s)
Anti-Inflammatory Agents/chemical synthesis , Immunosuppressive Agents/chemical synthesis , Thiazoles/chemical synthesis , Amides , Chemical Phenomena , Chemistry , Structure-Activity Relationship
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