GB1117068A - S-triazole-[4,3-a]-pyridine derivatives and processes for their preparation - Google Patents
S-triazole-[4,3-a]-pyridine derivatives and processes for their preparationInfo
- Publication number
- GB1117068A GB1117068A GB5073866A GB5073866A GB1117068A GB 1117068 A GB1117068 A GB 1117068A GB 5073866 A GB5073866 A GB 5073866A GB 5073866 A GB5073866 A GB 5073866A GB 1117068 A GB1117068 A GB 1117068A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyridine
- triazolo
- general formula
- prepared
- chloropropyl
- 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
Links
- LJRXNXBFJXXRNQ-UHFFFAOYSA-N 2h-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC=CN2C(=O)NN=C21 LJRXNXBFJXXRNQ-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- GHYVTQQUEXIUIT-UHFFFAOYSA-N 1-(2,2-dichloroethyl)cyclohexa-2,4-dien-1-amine Chemical compound ClC(CC1(N)CC=CC=C1)Cl GHYVTQQUEXIUIT-UHFFFAOYSA-N 0.000 abstract 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 208000001953 Hypotension Diseases 0.000 abstract 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 235000011114 ammonium hydroxide Nutrition 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Novel compounds having tranquilizing, hypotensive and analgesic action of the general formula <FORM:1117068/C2/1> wherein R is H or CH3 and R1 is alkyl containing 1-4 carbon atoms, alkoxy containing 1-4 carbon atoms or halogen, and the non-toxic salts thereof with organic or inorganic acids are prepared by reacting an s-triazolo(4,3-a)-pyridine-3-one of the general formula <FORM:1117068/C2/2> or its sodium salt with an N-aryl-N1-o -halo-propyl -piperazine of the general formula <FORM:1117068/C2/3> or treating a 2-o -halopropyl-s-triazolo-(4,-3-a) -pyridine - 3 - one of the general formula <FORM:1117068/C2/4> with a suitable N-aryl-piperazine; or reacting a 2-o -morpholinopropyl-s-triazolo-(4,3-a)-pyridine-3-one of the general formula <FORM:1117068/C2/5> with a suitably substituted aniline; or reacting a b ,b 1-dichloroethyl-aniline of the general formula <FORM:1117068/C2/6> with a 2-o -aminopropyl-s-triazolo-(4,3-a)-pyridine-3-one of the general formula <FORM:1117068/C2/7> The starting material 2-o -chloropropyl-s-triazolo - (4,3-a) - pyridine - 3 - one is prepared by treating s-triazolo(4,3-a)-pyridine-3-one with sodium hydride in dioxan solution and then adding 1-bromo-3-chloropropane. 2-o -morpholinopropyl -s-triazolo(4,3-a)-pyridine-3-one hydrochloride is prepared by refluxing s-triazolo-(4,3 - a) - pyridine - 3 - one, sodamide and N - a - chloropropyl - morpholine, basifying, extracting, and precipitating the product with ethereal hydrochloric acid. 2-o -aminopropyl-s-triazolo(4,3-a) -pyridine-3-one is prepared by heating 2-a -chloropropyl-s-triazolo(4,3-a)-pyridine-3-one and saturated alcoholic ammonia solution in a sealed tube.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT27806/65A IT1066857B (en) | 1965-12-15 | 1965-12-15 | DERIVATIVES OF S IPIAZOLE 4.3 A PYRIDIN AND PROCESSES FOR THEIR PREPARATION |
| IT1802866A IT1056705B (en) | 1966-08-03 | 1966-08-03 | DERIVATIVES OF S TRIAZOL 4,3 A PYRIDINE AND PROCESS FOR THEIR PREPARATION |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1117068A true GB1117068A (en) | 1968-06-12 |
Family
ID=26326965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5073866A Expired GB1117068A (en) | 1965-12-15 | 1966-11-11 | S-triazole-[4,3-a]-pyridine derivatives and processes for their preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1117068A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0062873A1 (en) * | 1981-04-13 | 1982-10-20 | Schering Corporation | 1-Substituted-4-phenyl-polyhydro-pyridines and -pyrrolidines, processes for their preparation and pharmaceutical compositions containing them |
| FR2672052A1 (en) * | 1991-01-28 | 1992-07-31 | Esteve Labor Dr | DERIVATIVES OF ARYL (OR HETEROARYL) -PIPERAZINYL-ALKYL-AZOLES, THEIR PREPARATION AND THEIR APPLICATION AS MEDICAMENTS. |
| EP1108722A1 (en) * | 1999-12-16 | 2001-06-20 | AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.p.A. | Trazodone hydrochloride and process for its preparation |
| WO2009019133A1 (en) * | 2007-08-03 | 2009-02-12 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | Trazodone and trazodone hydrochloride in purified form |
| EP3922250A4 (en) * | 2019-09-24 | 2022-12-07 | Obshestvo S Ogranichennoy Otvetstvennost'Yu "Nauchno-Proizvodstvennaya Kompaniya "Skiff" | Composition for correcting the behaviour of cats and dogs |
-
1966
- 1966-11-11 GB GB5073866A patent/GB1117068A/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0062873A1 (en) * | 1981-04-13 | 1982-10-20 | Schering Corporation | 1-Substituted-4-phenyl-polyhydro-pyridines and -pyrrolidines, processes for their preparation and pharmaceutical compositions containing them |
| US5292739A (en) * | 1990-01-28 | 1994-03-08 | Laboratorios Del Dr. Esteve, S.A. | Aryl(or heteroaryl) piperazinylalkylazole derivatives, their preparation and their application as medicaments |
| FR2672052A1 (en) * | 1991-01-28 | 1992-07-31 | Esteve Labor Dr | DERIVATIVES OF ARYL (OR HETEROARYL) -PIPERAZINYL-ALKYL-AZOLES, THEIR PREPARATION AND THEIR APPLICATION AS MEDICAMENTS. |
| US5382586A (en) * | 1991-01-28 | 1995-01-17 | Laboratorios Del Dr. Esteve S.A. | Aryl (or heteroaryl)piperazinylalkylazole derivatives, their preparation and their application as medicaments |
| EP1108722A1 (en) * | 1999-12-16 | 2001-06-20 | AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.p.A. | Trazodone hydrochloride and process for its preparation |
| WO2009019133A1 (en) * | 2007-08-03 | 2009-02-12 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | Trazodone and trazodone hydrochloride in purified form |
| US8133893B2 (en) | 2007-08-03 | 2012-03-13 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | Trazodone and trazodone hydrochloride in purified form |
| EA017019B1 (en) * | 2007-08-03 | 2012-09-28 | Ацьенде Кимике Рьюните Анджелини Франческо А.К.Р.А.Ф. С.П.А. | Trazodone and trazodone hydrochloride in purified form |
| EP3922250A4 (en) * | 2019-09-24 | 2022-12-07 | Obshestvo S Ogranichennoy Otvetstvennost'Yu "Nauchno-Proizvodstvennaya Kompaniya "Skiff" | Composition for correcting the behaviour of cats and dogs |
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