CA1100504A - S-triazolo [1,5-a] pyridine derivatives - Google Patents
S-triazolo [1,5-a] pyridine derivativesInfo
- Publication number
- CA1100504A CA1100504A CA322,196A CA322196A CA1100504A CA 1100504 A CA1100504 A CA 1100504A CA 322196 A CA322196 A CA 322196A CA 1100504 A CA1100504 A CA 1100504A
- Authority
- CA
- Canada
- Prior art keywords
- triazolo
- pyridine
- compound
- propyl
- prepared
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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Abstract
ABSTRACT
Compounds of the formula wherein R is -CH-N-N-(CH3)2 or
Compounds of the formula wherein R is -CH-N-N-(CH3)2 or
Description
-`" 11C3~5~
This invention relates to new compounds of value as antihypertensives and more particularly to new s-triazolo~1,5-a~pyridine derivatives and their pharmacologically acceptable acid addition salts.
The novel s-triazolo[1,5-a~pyridine derivatives of the present invention can be represented by the general formula (I), (I) N ~N
N~``R
wherein R represents -CH=N-N-(CH3)2 or -(CH2) -N N-R , wherein R represents phenyl, 2-methoxyphenyl, benzyl, 2-chlorobenzyl or 2-pyridyl, and n represents 3 or 5.
The novel compounds of the present invention can be prepared by the following procedures.
The compound represented by the general formula (I), wherein R represents -CH=N-N-(CH3)2, can be prepared by reacting 2-dihalogenomethyl-s-triazolo ll,5-a~Pyridine ("halogeno" being chlorine, bromine or iodine) with the corresponding substituted hydra~ine in a solvent as, for example, dimethyl-formamide, and preferably in the presence of a base as, for example, potassium carbonate.
The 2-dihalogenomethyl-s-triazolo a,5-aJpyridine starting compounds can be prepared by reacting 1,2-diaminopyridinium iodide with methyl dihalogeno-acetate.
20The compounds represented by the general formula (I), wherein R
represents -(C112)n-N~___N-R , in which -R and n are as already defined, can be prepared by reacting a compound having the general formula (II), .~, . --1-- `
.: ' -.
` 11(~C~5~4 ~'~
IN (II) N
(CH2) n~X
wherein X represents halogen (chlorine, bromine or iodine) and n is as already defined with a compound having the general formula (III), (III) wherein R is as already defined, in a solvent as, for example, ethanol, dimethylformamide or toluene, and preferably in the presence of an equimolar or greater amount of a base as, for example, potassium carbonate or triethyl-amine at a temperature near the boiling point of the solvent used.
The fol:Lowing examples serve to illustrate the invention.
Reference examples:
1) 2-Dichloromethyl-s-triazolo~L,~-37pyridine A solution of 24 g of 1,2-diaminopyridinium iodide and 6.6g of sodium hydroxide in 200 ml of ethanol was stirred at 50-60C for 1 hour. To the reaction mixture was added 17.2g of methyl dichloroacetate and the mixture was refluxed with stirring for 4 hours. The mixture was concentrated under reduced pressure, water was added followed by extraction with chloroform.
The chloroform layer was evaporated to give crude crystalline product, which was recrystallized from 60 ml of benzene. Colorless needles, mp 133-134 C, in the amount of ~6.8g were obtained.
Analysis:
Calcd. for C7115N3C12 : C, 41.61; H, 2.49; N, 20-80-110~?50~
Found:
C, 41.91; H, 2.55; N, 20.83.
This invention relates to new compounds of value as antihypertensives and more particularly to new s-triazolo~1,5-a~pyridine derivatives and their pharmacologically acceptable acid addition salts.
The novel s-triazolo[1,5-a~pyridine derivatives of the present invention can be represented by the general formula (I), (I) N ~N
N~``R
wherein R represents -CH=N-N-(CH3)2 or -(CH2) -N N-R , wherein R represents phenyl, 2-methoxyphenyl, benzyl, 2-chlorobenzyl or 2-pyridyl, and n represents 3 or 5.
The novel compounds of the present invention can be prepared by the following procedures.
The compound represented by the general formula (I), wherein R represents -CH=N-N-(CH3)2, can be prepared by reacting 2-dihalogenomethyl-s-triazolo ll,5-a~Pyridine ("halogeno" being chlorine, bromine or iodine) with the corresponding substituted hydra~ine in a solvent as, for example, dimethyl-formamide, and preferably in the presence of a base as, for example, potassium carbonate.
The 2-dihalogenomethyl-s-triazolo a,5-aJpyridine starting compounds can be prepared by reacting 1,2-diaminopyridinium iodide with methyl dihalogeno-acetate.
20The compounds represented by the general formula (I), wherein R
represents -(C112)n-N~___N-R , in which -R and n are as already defined, can be prepared by reacting a compound having the general formula (II), .~, . --1-- `
.: ' -.
` 11(~C~5~4 ~'~
IN (II) N
(CH2) n~X
wherein X represents halogen (chlorine, bromine or iodine) and n is as already defined with a compound having the general formula (III), (III) wherein R is as already defined, in a solvent as, for example, ethanol, dimethylformamide or toluene, and preferably in the presence of an equimolar or greater amount of a base as, for example, potassium carbonate or triethyl-amine at a temperature near the boiling point of the solvent used.
The fol:Lowing examples serve to illustrate the invention.
Reference examples:
1) 2-Dichloromethyl-s-triazolo~L,~-37pyridine A solution of 24 g of 1,2-diaminopyridinium iodide and 6.6g of sodium hydroxide in 200 ml of ethanol was stirred at 50-60C for 1 hour. To the reaction mixture was added 17.2g of methyl dichloroacetate and the mixture was refluxed with stirring for 4 hours. The mixture was concentrated under reduced pressure, water was added followed by extraction with chloroform.
The chloroform layer was evaporated to give crude crystalline product, which was recrystallized from 60 ml of benzene. Colorless needles, mp 133-134 C, in the amount of ~6.8g were obtained.
Analysis:
Calcd. for C7115N3C12 : C, 41.61; H, 2.49; N, 20-80-110~?50~
Found:
C, 41.91; H, 2.55; N, 20.83.
2) 2-(3-Chloropropyl)-s-triazolo~1,5-a7pyridine A) A mixture of 24g of 1,2-diaminopyridinium iodide, 17.2g of ~-butyro-lactone and 57g of potassium carbonate in 100 ml of diethy]cellosolve was refluxed with stirring for 8 hours. The mixture was evaporated under reduced pressure and the residue, extracted with hot dichloromethane. The solvent was removed to give crude 2-(3-hydroxypropyl)-s-triazolo~i,5-a~pyridine, which was recrystallized from ethyl acetate as colorless needles (16g, 90~=), mp 71.5-73C.
Analysis:
Calcd. for CgHllON3 : C, 61.00; H, 6.24; N, 23-72-Found:
C, 60.82; H, 6.14; N, 23.48.
B) To 50 ml of phosphorus oxychloride was added gradually 34.5g of 2-(3-hydroxypropyl)-s-triazolo~1,5-a~pyridine. After the addition was complete, the mixture was warmed on a water bath at 90-95C for 30 min., cooled and poured onto cracked ice. The mixture was neutralized with potassium carbonate and extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate and evaporated to give the crude product, which was recrystal-lized from cyclohexane as colorless needles (22.5g, mp 56.5-57 C).
Analysis:
Calcd. for CgHloN3Cl : C, 55.25; H, 5-15; N~ 21-48-Found:
C, 55.2]; H, 5.20; N, 21.55.
Analysis:
Calcd. for CgHllON3 : C, 61.00; H, 6.24; N, 23-72-Found:
C, 60.82; H, 6.14; N, 23.48.
B) To 50 ml of phosphorus oxychloride was added gradually 34.5g of 2-(3-hydroxypropyl)-s-triazolo~1,5-a~pyridine. After the addition was complete, the mixture was warmed on a water bath at 90-95C for 30 min., cooled and poured onto cracked ice. The mixture was neutralized with potassium carbonate and extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate and evaporated to give the crude product, which was recrystal-lized from cyclohexane as colorless needles (22.5g, mp 56.5-57 C).
Analysis:
Calcd. for CgHloN3Cl : C, 55.25; H, 5-15; N~ 21-48-Found:
C, 55.2]; H, 5.20; N, 21.55.
3) 2-(5-Chloropentyl)-s-triazoloLl,5-a7pyridine In the same manner as described in Example for Reference Example 2, 110~5~4 parts A and B, the title compound was prepared by using ~-caprolactone in 45%
total yield and was obtained as an oil, of which the picrate melts at 136-137C.Analysis:
11 14N3Cl.C6H307N3 : C, 45.09; H, 3-78; N~ 18 56 Found:
C, 43.39; H, 3.36; N, 18.75.
Example 1. 2-(N,N-Dimethylhydrazonomethyl):s-triazoloLl,5-a~pyridine A mixture of ll.Og of 2-dichloromethyl-s-triazoloC1,5-a~pyridine, 7.6g of potassium carbonate, 300 mg of sodium iodide and 12g of N,N-dimethylhydrazinein 160 ml of dimethylformamide was refluxed with stirring for 12 hours. rhe solvent was removed under reduced pressure and to the residue was added 200 ml of water saturated with sodium chloride. The mixture was extracted with chloroform. The extracts were evaporated and the residue was recrystallized from benzene-n-hexane to give colorless crystals (5.6g, mp 132-133C).
Analysis:
Calcd. for CgllllN5 : C, 57.12; H- 5.86; N, 37.02.
Found:
C, 57.18; H, 5.97; N, 37.19.
Example 2. 2-~3-(4-Phenylpiperazino)propyl7-s-triazoloLl,5-a~pyridine A solution of 5.7g of 2-(3-chloropropyl)-s-triazolo~1,5-a7pyridine, 5.2g of ]-phenylpiperazine and 10 ml of triethylamine in 140 ml of dimethyl-formamide was refluxed for 10 hours. rhe reaction mixture was evaporated under reduced pressure and lN-aqueous sodium hydroxide (50 ml) was added to the residue. rne mixture was extracted with chloroform and the extracts were evaporated to give the crude product, which was purified by alumina column chromatography to obtain 7.1g of oily product. The oily product was converted to a salt with maleic acid in the conventional way. llle maleate was re-crystallized from ethanol-petroleum ether (10:4) to yield colorless prisms, )S~
mp 167.5-168.5 C. The yield was 50%.
Analysis:
Calcd. for ClgH23N3.C4H4O4 : C, 63.14; H, 6.22; N, 16-01-Found:
C, 63.03; H, 6.22; N, 16.14.
Example 3. 2-~3-(4-o-Methoxyphenylpiperazino)propyl~-s-triazoloLL,5-a~pyridine A solution of 3.9g of 2-(3-chloropropyl)-s-triazoloLl,5-a~pyridine, 3.8g of l-o-methoxyphenylpiperazine and 2.8g of potassium carbonate in 150 ml of dimethylformamide was refluxed from 8 hours. Then the reaction mixture was processed in the same manner as described in Example 2. The product compound was recrystallized from cyclohexane to give colorless prisms, mp 55-55.5 C, yield 60%.
Analysis:
Calcd. for C20H250N5 : C, 68.35; H, 7.:L7; N, 19-53-Found:
C, 68.20; H, 6.94; N, 20.21.
The compounds of Examples 4 to 8 were prepared in a manner analogous to that described in Example 3.
I N
N ~ (CH2) -N N-R
n llQ~5~4 . .
.
Analysis Example n R2 Yield mp Recryst. alcd. C H N
t%) ( C) solvent Found. C H N
.
total yield and was obtained as an oil, of which the picrate melts at 136-137C.Analysis:
11 14N3Cl.C6H307N3 : C, 45.09; H, 3-78; N~ 18 56 Found:
C, 43.39; H, 3.36; N, 18.75.
Example 1. 2-(N,N-Dimethylhydrazonomethyl):s-triazoloLl,5-a~pyridine A mixture of ll.Og of 2-dichloromethyl-s-triazoloC1,5-a~pyridine, 7.6g of potassium carbonate, 300 mg of sodium iodide and 12g of N,N-dimethylhydrazinein 160 ml of dimethylformamide was refluxed with stirring for 12 hours. rhe solvent was removed under reduced pressure and to the residue was added 200 ml of water saturated with sodium chloride. The mixture was extracted with chloroform. The extracts were evaporated and the residue was recrystallized from benzene-n-hexane to give colorless crystals (5.6g, mp 132-133C).
Analysis:
Calcd. for CgllllN5 : C, 57.12; H- 5.86; N, 37.02.
Found:
C, 57.18; H, 5.97; N, 37.19.
Example 2. 2-~3-(4-Phenylpiperazino)propyl7-s-triazoloLl,5-a~pyridine A solution of 5.7g of 2-(3-chloropropyl)-s-triazolo~1,5-a7pyridine, 5.2g of ]-phenylpiperazine and 10 ml of triethylamine in 140 ml of dimethyl-formamide was refluxed for 10 hours. rhe reaction mixture was evaporated under reduced pressure and lN-aqueous sodium hydroxide (50 ml) was added to the residue. rne mixture was extracted with chloroform and the extracts were evaporated to give the crude product, which was purified by alumina column chromatography to obtain 7.1g of oily product. The oily product was converted to a salt with maleic acid in the conventional way. llle maleate was re-crystallized from ethanol-petroleum ether (10:4) to yield colorless prisms, )S~
mp 167.5-168.5 C. The yield was 50%.
Analysis:
Calcd. for ClgH23N3.C4H4O4 : C, 63.14; H, 6.22; N, 16-01-Found:
C, 63.03; H, 6.22; N, 16.14.
Example 3. 2-~3-(4-o-Methoxyphenylpiperazino)propyl~-s-triazoloLL,5-a~pyridine A solution of 3.9g of 2-(3-chloropropyl)-s-triazoloLl,5-a~pyridine, 3.8g of l-o-methoxyphenylpiperazine and 2.8g of potassium carbonate in 150 ml of dimethylformamide was refluxed from 8 hours. Then the reaction mixture was processed in the same manner as described in Example 2. The product compound was recrystallized from cyclohexane to give colorless prisms, mp 55-55.5 C, yield 60%.
Analysis:
Calcd. for C20H250N5 : C, 68.35; H, 7.:L7; N, 19-53-Found:
C, 68.20; H, 6.94; N, 20.21.
The compounds of Examples 4 to 8 were prepared in a manner analogous to that described in Example 3.
I N
N ~ (CH2) -N N-R
n llQ~5~4 . .
.
Analysis Example n R2 Yield mp Recryst. alcd. C H N
t%) ( C) solvent Found. C H N
.
4 3-CH ~ 40 picrate E 48.43 3.94 19.41 2 234-236 48.37 4.10 19.39 3-CH2 ~ 57 maleate E 55.85 5.36 11.63 Cl ~ 172-173 55.85 5.56 11.~2 6 3 ~ 42 77.5 c*2 67.05 6.88 26.07 67.09 6.84 25.99 7 5 ~ 56 oil*3 8 5 ~ 60 oil 4 CH30~--1 E : ethanol 2 C : cyclohexane 3 Structure confirmed by mass spectral analysis, m/e 349 (M ).
4 Structure confirmed by mass spectral analysis, m/e 379 (M ).
The antihypertensive effect of the compounds of this invention is shown given in Table 1 to follow.
Blood pressure was determined under unanesthetized and unrestrained conditions in spontaneously hypertensive rats (SH rat) which had been implanted chronically with a cannula into the femoral vein. The results are presented as the mean decreased percent in blood pressure determined at 15, 30, 60, 120 and 180 minutes after intraperitoneal (i.p.) or oral (p.o.) administration of the test compounds.
The compounds of this invention showed more potent antihypertensive effect in SH rats than the reference drugs, and are thus promising as antihypertensive drugs.
S~4 Table 1. Antihypertensive effect in SH rats .
.
-Example Decreased % in blood pressure ~o .
i.p. : p.o.
30 mg/kg 10 mg/kg ::. 30 mg/kg. 100 mg/kg 2 30 ` 7 26 Hexamethonium 11 Guanethidine 12 _ . _ . .
. --7--
4 Structure confirmed by mass spectral analysis, m/e 379 (M ).
The antihypertensive effect of the compounds of this invention is shown given in Table 1 to follow.
Blood pressure was determined under unanesthetized and unrestrained conditions in spontaneously hypertensive rats (SH rat) which had been implanted chronically with a cannula into the femoral vein. The results are presented as the mean decreased percent in blood pressure determined at 15, 30, 60, 120 and 180 minutes after intraperitoneal (i.p.) or oral (p.o.) administration of the test compounds.
The compounds of this invention showed more potent antihypertensive effect in SH rats than the reference drugs, and are thus promising as antihypertensive drugs.
S~4 Table 1. Antihypertensive effect in SH rats .
.
-Example Decreased % in blood pressure ~o .
i.p. : p.o.
30 mg/kg 10 mg/kg ::. 30 mg/kg. 100 mg/kg 2 30 ` 7 26 Hexamethonium 11 Guanethidine 12 _ . _ . .
. --7--
Claims (22)
IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A process for the preparation of a compound of formula (I) where R represents -CH=N-N-(CH3)2 or wherein R2 is phenyl, 2-methoxyphenyl, benzyl, 2-chlorobenzyl or 2-pyridyl and n is 3 or 5, which comprises (i) when R is -CH=N-N-(CH3)2, reacting N,N- dimethylhydrazine with 2-dihalogenomethyl-s-triazolo[1,5-a]pyridine wherein "halogeno" is chloro, bromo or iodo, or (ii) when R is reacting a compound of the formula (II) wherein n is 3 or 5 and X is chlorine, bromine or iodine, with a compound of the general formula wherein R2 is as already defined, and recovering the compound of formula (I) and, where required preparing a pharmaceutically acceptable acid addition salt thereof.
2. A compound of the formula (I
or its pharmaceutically acceptable acid addition salts when prepared by the process of claim 1 or an obvious chemical equivalent.
or its pharmaceutically acceptable acid addition salts when prepared by the process of claim 1 or an obvious chemical equivalent.
3. A process for the preparation of the compound 2(N,N-dimethyl-hydrazonomethyl)-s-triazolo[1,5-a]pyridine which comprises reacting 2-dichloromethyl-s-triazolo[1,5-a]pyridine with N,N-dimethylhydrazine in the presence of a solvent and a base and recovering the required compound.
4. 2(N,N-dimethylhydrazonomethyl)-s-triazolo[1,5-a]pyridine when prepared by the process of claim 1 or an obvious chemical equivalent.
5. A process for the preparation of the compound 2-[3-(4-phenyl-piperazino)propyl]-s-triazolo[1,5-a]pyridine which comprises reacting 2-(3-chloropropyl)-s-triazolo[1,5-a]pyridine with 1-phenyl piperazine in the presence of a solvent and a base and recovering the required compound.
6. The process of claim 5 wherein crude 2-[3-(4-phenylpiperazino)propyl]-s-triazolo[1,5-a]pyridine is converted to the maleate salt and said salt recovered.
7. 2-[3-(4-Phenylpiperazino)propyl]-s-triazolo[1,5-a]pyridine when prepared by the process of claim 5 or an obvious chemical equivalent.
8. 2-[3-(4-Phenylpiperazino)propyl]-s-triazolo[1,5-a]pyridine maleate when prepared by the process of claim 6 or an obvious chemical equivalent.
9. A process for the preparation of the compound 2-[3-(4-benzylpiperaz-ino)propyl]-s-triazolo[1,5-a]pyridine which comprises reacting 2-(3-chloro-propyl)-s-triazolo[1,5-a]pyridine with 1-benzylpiperazine in the presence of a solvent and a base and recovering the required compound.
10. The process of claim 9 wherein crude 2-[3-(4-benzylpiperazino) propyl]-s-triazolo[1,5-a]pyridine is converted to the picrate salt and said salt recovered.
11. 2-[3-(4-Benzylpiperazino)propyl]-s-triazolo[1,5-a]pyridine when prepared by the process of claim 9 or an obvious chemical equivalent.
12. 2-[3-(4-benzylpiperazino)propyl]-s-triazolo[1,5-a]pyridine picrate when prepared by the process of claim 10 or an obvious chemical equivalent.
13. A process for the preparation of the compound 2-[3-(4-o-chloro-benzylpiperazino)propyl]-s-triazolo[1,5-a]pyridine which comprises reacting 2-(3-chloropropyl)-s-triazolo[1,5-a]pyridine with 1-(o-chlorobenzyl) piperazine in the presence of a solvent and a base and recovering the required compound.
14. The process of claim 13 wherein crude 2-[3-(4-o-chlorobenzyl-piperazino)propyl]-s-triazolo[1,5-a]pyridine is converted to the maleate salt and said salt recovered.
15. 2-[3-(4-o-Chlorobenzylpiperazino)propyl]-s-triazolo[1,5-a]pyridine when prepared by the process of claim 13 or an obvious chemical equivalent.
16. 2-[3-(4-o-Chlorobenzylpiperazino)propyl]-s-triazolo[1,5-a]pyridine maleate when prepared by the process of claim 14 or an obvious chemical equivalent.
17. A process for the preparation of the compound 2-[3-(4-pyridin-2-ylpiperazino)propyl]-s-triazolo[1,5-a]pyridine which comprises reacting 2-(3-chloropropyl)-s-triazolo[1,5-a]pyridine with 1-(2-pyridyl)piperazine in the presence of a solvent and a base and recovering the required compound.
18. 2-[3-(4-Pyridin-2-ylpiperazino)propyl]-s-triazolo[1,5-a]pyridine when prepared by the process of claim 17 or an obvious chemical equivalent.
19. A process for the preparation of the compound 2-[5-(4-phenyl-piperazino)pentyl]-s-triazolo[1,5-a]pyridine which comprises reacting 2-(5-chloropentyl)-s-triazolo[1,5-a]pyridine with 1-phenylpiperazine in the presence of a solvent and a base and recovering the required compound.
20. 2-[5-(4-Phenylpiperazino)pentyl]-s-triazolo[1,5-a]pyridine when prepared by the process of claim 19 or an obvious chemical equivalent.
21. A process for the preparation of the compound 2-[5-(4-o-methoxy-phenylpiperazino)pentyl]-s-triazolo[1,5-a]pyridine which comprises reacting 2-(5-chloropentyl)-s-triazolo[1,5-a]pyridine with 1-o-methoxyphenylpiperazine in the presence of a solvent and a base and recovering the required compound.
22. 2-[5-(4-o-Methoxyphenylpiperazino)pentyl]-s-triazolo[1,5-a]
pyridine when prepared by the process of claim 21 or an obvious chemical equivalent.
pyridine when prepared by the process of claim 21 or an obvious chemical equivalent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA322,196A CA1100504A (en) | 1979-02-23 | 1979-02-23 | S-triazolo [1,5-a] pyridine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA322,196A CA1100504A (en) | 1979-02-23 | 1979-02-23 | S-triazolo [1,5-a] pyridine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1100504A true CA1100504A (en) | 1981-05-05 |
Family
ID=4113620
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA322,196A Expired CA1100504A (en) | 1979-02-23 | 1979-02-23 | S-triazolo [1,5-a] pyridine derivatives |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1100504A (en) |
-
1979
- 1979-02-23 CA CA322,196A patent/CA1100504A/en not_active Expired
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