SU628819A3 - Method of producing derivatives of tetrahydrothienopyridine - Google Patents
Method of producing derivatives of tetrahydrothienopyridineInfo
- Publication number
- SU628819A3 SU628819A3 SU762366005A SU2366005A SU628819A3 SU 628819 A3 SU628819 A3 SU 628819A3 SU 762366005 A SU762366005 A SU 762366005A SU 2366005 A SU2366005 A SU 2366005A SU 628819 A3 SU628819 A3 SU 628819A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- tetrahydrothienopyridine
- producing derivatives
- producing
- hydrogen
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 4
- WJFYLCXWEXZNHU-UHFFFAOYSA-N 2,3,3a,4-tetrahydrothieno[3,2-b]pyridine Chemical class N1C=CC=C2SCCC21 WJFYLCXWEXZNHU-UHFFFAOYSA-N 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- OJYDKYKQCVPTFG-UHFFFAOYSA-N 2,3,3a,4-tetrahydrothieno[3,2-c]pyridine Chemical class C1N=CC=C2SCCC21 OJYDKYKQCVPTFG-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- -1 nitro, cyanoacetamido Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Изобретение относитс х способу получени новых производных тетрагидротиено (3,2-с) пиридина, которы может найти применение в химико-фар мацевтической промышленности. Известен способ получени аминометильных соединений взаимодействием соединений с подвижным атомом водорода с карбонильнЕлми соединени ми и аминами (реакци Манниха) 1 . Целью изобретени вл етс разработка способа получени новых производных тетрагидротиено (3,2-с) пи ридина, обладающих ценными .фармаколо гическими свойствами, основанного на известной в iорганической химии реакции. Поставленна цель достигаетс способом получени производных тетрагидротиено (3,2-с) пиридина общей 1 юрмулы т N-СНг где - водород или низишй алкил; . водород,галоген,низший алкил,низший алкоксил,нитро-,цианоацетамидо- или ди(низший алкил)амин группа, причем когда гидроксил находитс во 2-положении, то Т HRjв 3-,4-, 5-или 6-положении,а когда гидроксил находитс в 4-положении, , 3 - в 3- и 5- положении и отличаютс от водорода, заключающимс в том, что соединений общей формулы II Л-if H . глеТ - указанвыше, подвергают взаимодействию сполиоксиметиЛеном и фенолом общей формулы указаны выае, в среде инертного органического растворител , лучше в этаноле, или в изопропаноле , или в диоксане, при температуре от 50 до температуры кипени растворител . Обычно процесс ведут при перемешивании в течение от 2 до 20 ч. Очистку целевых продуктов ведут обычными приемами, например перекристаллизацией из органическихThe invention relates to a process for the preparation of tetrahydrothieno (3,2-c) pyridine derivatives, which can be used in the chemical-pharmaceutical industry. A known method for producing aminomethyl compounds by reacting compounds with a mobile hydrogen atom with carbonyl compounds and amines (Mannich reaction) 1. The aim of the invention is to develop a method for producing new tetrahydrothieno (3,2-c) pyridine derivatives having valuable pharmacological properties, based on the reaction known in organic chemistry. The goal has been achieved by a method for the preparation of tetrahydrothieno (3,2-c) pyridine derivatives with a total of 1 Jmula t N-CHg, where is hydrogen or lower alkyl; . hydrogen, halogen, lower alkyl, lower alkoxy, nitro, cyanoacetamido or di (lower alkyl) amine group, and when the hydroxyl is in the 2-position, then T HRj in the 3-, 4-, 5- or 6-position, and when the hydroxyl is in the 4-position, 3 is in the 3- and 5-position and differs from hydrogen, which means that the compounds of general formula II are L-if H. GluT is indicated above, is subjected to the interaction of spioxymethylene and phenol of the general formula indicated above, in an inert organic solvent, preferably in ethanol, or in isopropanol, or in dioxane, at a temperature from 50 to the boiling point of the solvent. Typically, the process is carried out with stirring for 2 to 20 hours. Purification of the target products is carried out by conventional methods, for example, by recrystallization from organic
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7521549A FR2317303A1 (en) | 1975-07-09 | 1975-07-09 | PROCESS FOR PREPARING TETRAHYDROTHIENO (3,2-C) AND (2,3-C) PYRIDINE DERIVATIVES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU628819A3 true SU628819A3 (en) | 1978-10-15 |
Family
ID=9157715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762366005A SU628819A3 (en) | 1975-07-09 | 1976-06-09 | Method of producing derivatives of tetrahydrothienopyridine |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS5236691A (en) |
| AR (1) | AR211019A1 (en) |
| AT (1) | AT348526B (en) |
| BE (1) | BE843822A (en) |
| CA (1) | CA1071634A (en) |
| CH (1) | CH609349A5 (en) |
| DD (1) | DD125081A5 (en) |
| DE (1) | DE2630474A1 (en) |
| DK (1) | DK141333B (en) |
| ES (1) | ES448404A1 (en) |
| FR (1) | FR2317303A1 (en) |
| GB (1) | GB1544093A (en) |
| GR (1) | GR59812B (en) |
| HU (1) | HU172280B (en) |
| IE (1) | IE42821B1 (en) |
| IL (1) | IL49641A (en) |
| LU (1) | LU74674A1 (en) |
| MX (1) | MX3224E (en) |
| NL (1) | NL7605362A (en) |
| PH (1) | PH12311A (en) |
| PL (1) | PL100685B1 (en) |
| PT (1) | PT65072B (en) |
| SE (1) | SE421699B (en) |
| SU (1) | SU628819A3 (en) |
| YU (1) | YU40137B (en) |
| ZA (1) | ZA763219B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5665315A (en) * | 1979-11-02 | 1981-06-03 | Nec Corp | Magnetic recording and inspecting system |
| DE3736664A1 (en) * | 1987-10-29 | 1989-05-11 | Boehringer Ingelheim Kg | TETRAHYDRO-FURO- AND -THIENO (2,3-C) PYRIDINE, THEIR USE AS A MEDICAMENT AND METHOD FOR THE PRODUCTION THEREOF |
| NZ233654A (en) * | 1989-05-18 | 1993-02-25 | Bristol Myers Squibb Co | 2-aminomethyl-5-aminophenol derivatives; hair dye compositions containing them |
-
1975
- 1975-07-09 FR FR7521549A patent/FR2317303A1/en active Granted
-
1976
- 1976-03-31 LU LU74674A patent/LU74674A1/xx unknown
- 1976-04-01 CH CH404576A patent/CH609349A5/en not_active IP Right Cessation
- 1976-04-21 GR GR50593A patent/GR59812B/en unknown
- 1976-04-23 YU YU1030/76A patent/YU40137B/en unknown
- 1976-05-06 PT PT65072A patent/PT65072B/en unknown
- 1976-05-19 NL NL7605362A patent/NL7605362A/en not_active Application Discontinuation
- 1976-05-21 IE IE1079/76A patent/IE42821B1/en unknown
- 1976-05-24 IL IL49641A patent/IL49641A/en unknown
- 1976-05-31 ES ES448404A patent/ES448404A1/en not_active Expired
- 1976-06-01 ZA ZA763219A patent/ZA763219B/en unknown
- 1976-06-03 AR AR263501A patent/AR211019A1/en active
- 1976-06-09 SU SU762366005A patent/SU628819A3/en active
- 1976-06-10 CA CA254,573A patent/CA1071634A/en not_active Expired
- 1976-06-16 MX MX000320U patent/MX3224E/en unknown
- 1976-07-01 DK DK297876AA patent/DK141333B/en not_active IP Right Cessation
- 1976-07-01 PH PH7618641A patent/PH12311A/en unknown
- 1976-07-05 AT AT489876A patent/AT348526B/en not_active IP Right Cessation
- 1976-07-06 BE BE168664A patent/BE843822A/en not_active IP Right Cessation
- 1976-07-07 DD DD193745A patent/DD125081A5/xx unknown
- 1976-07-07 SE SE7607762A patent/SE421699B/en not_active IP Right Cessation
- 1976-07-07 DE DE19762630474 patent/DE2630474A1/en active Pending
- 1976-07-08 JP JP51081441A patent/JPS5236691A/en active Granted
- 1976-07-08 GB GB28511/76A patent/GB1544093A/en not_active Expired
- 1976-07-08 PL PL1976191016A patent/PL100685B1/en unknown
- 1976-07-09 HU HU76PA00001255A patent/HU172280B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH609349A5 (en) | 1979-02-28 |
| GR59812B (en) | 1978-03-01 |
| FR2317303A1 (en) | 1977-02-04 |
| PH12311A (en) | 1979-01-16 |
| DD125081A5 (en) | 1977-03-30 |
| SE7607762L (en) | 1977-01-10 |
| IE42821L (en) | 1977-01-09 |
| PL100685B1 (en) | 1978-10-31 |
| GB1544093A (en) | 1979-04-11 |
| AU1568676A (en) | 1977-03-31 |
| YU103076A (en) | 1982-02-28 |
| ATA489876A (en) | 1978-07-15 |
| AR211019A1 (en) | 1977-10-14 |
| SE421699B (en) | 1982-01-25 |
| YU40137B (en) | 1985-08-31 |
| AT348526B (en) | 1979-02-26 |
| CA1071634A (en) | 1980-02-12 |
| JPS5310077B2 (en) | 1978-04-11 |
| HU172280B (en) | 1978-07-28 |
| LU74674A1 (en) | 1976-09-01 |
| PT65072B (en) | 1977-09-13 |
| ES448404A1 (en) | 1977-07-01 |
| MX3224E (en) | 1980-07-28 |
| IL49641A0 (en) | 1976-07-30 |
| IL49641A (en) | 1978-08-31 |
| PT65072A (en) | 1976-06-01 |
| DK297876A (en) | 1977-01-10 |
| DK141333C (en) | 1980-08-25 |
| BE843822A (en) | 1977-01-06 |
| FR2317303B1 (en) | 1977-12-16 |
| DE2630474A1 (en) | 1977-01-13 |
| JPS5236691A (en) | 1977-03-22 |
| DK141333B (en) | 1980-02-25 |
| ZA763219B (en) | 1977-05-25 |
| IE42821B1 (en) | 1980-10-22 |
| NL7605362A (en) | 1977-01-11 |
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