SU504481A3 - Method for preparing imidazo (4,5-b) pyridine derivatives - Google Patents

Method for preparing imidazo (4,5-b) pyridine derivatives

Info

Publication number
SU504481A3
SU504481A3 SU1936093A SU1936093A SU504481A3 SU 504481 A3 SU504481 A3 SU 504481A3 SU 1936093 A SU1936093 A SU 1936093A SU 1936093 A SU1936093 A SU 1936093A SU 504481 A3 SU504481 A3 SU 504481A3
Authority
SU
USSR - Soviet Union
Prior art keywords
pyridine
methylimidazo
general formula
salts
coorj
Prior art date
Application number
SU1936093A
Other languages
Russian (ru)
Inventor
Боеш Роже
Original Assignee
Рон-Пуленк С.А. (Фирма)
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Рон-Пуленк С.А. (Фирма) filed Critical Рон-Пуленк С.А. (Фирма)
Application granted granted Critical
Publication of SU504481A3 publication Critical patent/SU504481A3/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic 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
    • C07D471/02Heterocyclic 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
    • C07D471/04Ortho-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Claims (1)

(54) СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ ИМИДАЗО ,5-в| ПИРИДИНА Реакци  осушествп етс  обычно в органическом растворителе при температуре , близкой к 25 С. Новые продукты обшей формулы I в известных случа х могут быть очищены физическими методами (дистилл цией, кристаллизацией, хроматографией) или хиMH4e6KHh .fH. кристаллизаци  последних, затем разложение в щелочной среде). Новые продукты согласно изобретению могут превращатьс  в кислотно-аддитив- ные соли или в соли четвертичного аммоние вого основани . Пример, Нагревают до 102° С в течение 5 час суспензию из 2,26 г 2-( 3-метоксикарбонилтиоуреидо) -3-аминопиридина и 2 г ацетата меди в 10 мл воды и 20 мл уксусной, кислоты. Фильтруют полученную суспензию и подщелачивают .фильтрат добавлением гйдоата okJiCM -аммони  ( d 6,92) до рН 8. Выдел етс  твердое вещество, которое отдел ют фильт рованием, промывают  гри раза 5 мл дистиллированной воды. Таким образом получают 0,6 г 2-метоксикарбониламиноимидазо пиридина с т.пл, 285-290 С Можно получить 15,5 г 2-(3-метокси карбонилтиоуреидо)-3-аминопигидина, кото рый разлагаетс  при 230 С, действием 15,2 г метипизотиодианатоформиата на г 2,3-диаминопиридина в 370 мл ацетонитрила при 25 С. По этому же способу, но примен   дру гие соответствующие исходнью продукты, можно получить следующие соединени : 2-этоксикарбониламино-5-метилимидазо 4,5-в пиридин, плав щийс  при 285 С с зложением; 2-метоксикарбониламино-5-метилимидазо 4,5-в) пиридин, плав щийс  при 271272°С; 2-метоксикарбониламино-6-метилимидазо , пиридин, разлагающийс  при 365368°С перед плавлением. . Формула изобретени  Способ получени  производных имидазо, ,5-йТ пиридина общей формулы - NH-COORj 11 , . -N где PI - атом водорода или алкил с 1-4 атомамк углерода; и - алкил с 1-4 атомами углерода, или их солей, о тличающийс  тем, что, циклизуют производное пиридина общей формулы о; -NH-COORj где Р и Bj имеют указанные значени , a.Rj- атом водорода или р адикал-CS-WHСОО о вьщелением целевого продукта в свободном виде или переводом его в соль известными приемами.(54) METHOD FOR OBTAINING IMIDAZO DERIVATIVES, 5-in | Pyridine The reaction is usually carried out in an organic solvent at a temperature close to 25 ° C. New products of general formula I can in certain cases be purified by physical methods (distillation, crystallization, chromatography) or mH4e6KHh .fH. crystallization of the latter, then decomposition in an alkaline medium). The novel products according to the invention can be converted to acid addition salts or to quaternary ammonium salts. Example: A suspension of 2.26 g of 2- (3-methoxycarbonylthioureido) -3-aminopyridine and 2 g of copper acetate in 10 ml of water and 20 ml of acetic acid is heated to 102 ° C for 5 hours. Filter the resulting suspension and alkalinize the filtrate by adding okJiCM ammonium hydroxide (d 6.92) to pH 8. A solid is separated, which is separated by filtration, washed 5 times with distilled water. Thus, 0.6 g of 2-methoxycarbonylaminoimidazo-pyridine with m.p. 285-290 ° C can be obtained. 15.5 g of 2- (3-methoxy carbonylthioureido) -3-aminopigidine can be obtained, which decomposes at g of methyl-isothiodianato-formate per g of 2,3-diaminopyridine in 370 ml of acetonitrile at 25 ° C. The following compounds can be obtained by the same method, but using other appropriate starting materials: 2-ethoxycarbonylamino-5-methylimidazo 4,5-in pyridine, being at 285 ° C with a deposition; 2-methoxycarbonylamino-5-methylimidazo 4,5-c) pyridine, melting at 271272 ° C; 2-methoxycarbonylamino-6-methylimidazo, pyridine, which decomposes at 365368 ° C before melting. . The invention The method of obtaining imidazo derivatives, 5th T of pyridine with the general formula NH-COORj 11,. -N where PI is a hydrogen atom or alkyl with 1-4 carbon atoms; and - alkyl with 1-4 carbon atoms, or salts thereof, characterized in that the pyridine derivative of the general formula o is cyclized; -NH-COORj where P and Bj have the indicated meanings, a. Rj is a hydrogen atom or p-radical-CS-WH COO to isolate the target product in free form or to salt it using known techniques.
SU1936093A 1971-08-25 1973-07-06 Method for preparing imidazo (4,5-b) pyridine derivatives SU504481A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7130825A FR2150236A2 (en) 1971-08-25 1971-08-25 Anthelmintic imidazo (4,5-b) pyridine derivs - with low mammalian toxicity,for oral human and veterinary use

Publications (1)

Publication Number Publication Date
SU504481A3 true SU504481A3 (en) 1976-02-25

Family

ID=9082201

Family Applications (1)

Application Number Title Priority Date Filing Date
SU1936093A SU504481A3 (en) 1971-08-25 1973-07-06 Method for preparing imidazo (4,5-b) pyridine derivatives

Country Status (5)

Country Link
JP (1) JPS5117558B2 (en)
AT (1) AT309434B (en)
CS (1) CS161784B2 (en)
FR (1) FR2150236A2 (en)
SU (1) SU504481A3 (en)

Also Published As

Publication number Publication date
FR2150236A2 (en) 1973-04-06
JPS5117558B2 (en) 1976-06-03
FR2150236B2 (en) 1974-10-18
AT309434B (en) 1973-07-15
CS161784B2 (en) 1975-06-10
JPS5029596A (en) 1975-03-25

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