SU793402A3 - Способ получени производных 1-пиперазинил-4н- -триазоло/3,4с/-тиено/2,3е/-1,4-диазепина - Google Patents
Способ получени производных 1-пиперазинил-4н- -триазоло/3,4с/-тиено/2,3е/-1,4-диазепина Download PDFInfo
- Publication number
- SU793402A3 SU793402A3 SU792746903A SU2746903A SU793402A3 SU 793402 A3 SU793402 A3 SU 793402A3 SU 792746903 A SU792746903 A SU 792746903A SU 2746903 A SU2746903 A SU 2746903A SU 793402 A3 SU793402 A3 SU 793402A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- radical
- triazolo
- piperazinyl
- thieno
- preparing
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 238000006356 dehydrogenation reaction Methods 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 229910052736 halogen Chemical group 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- -1 methoxyphenyl Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000006501 nitrophenyl group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- QAQNWCMGKXMUQT-UHFFFAOYSA-N 6,7-dihydro-1h-1,4-diazepine Chemical compound C1CC=NC=CN1 QAQNWCMGKXMUQT-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing 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
- C07D495/12—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 three hetero rings
- C07D495/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
перекристаллизовывают этанолом. Выход 52,7 г (97,3% от теории); т.пл. 215-21бс.
Пример 3. 8-Бром-6-(о-хлорфенил )-1-пиперазинил-4Н-5-триазоло 3 ,4-сЗтиеноГ2, З-е 1, 4-диазепин.
4,6 г 0,01 моль 8-бром-6- о-хлорфенил )-1-пиперазинил -4Н-5-триазоло 3, 4-cJ тиено 2 , 3-е 5, 6-дигид- ро 1,4-диазепина раствор ют в 100 мл дистиллированного над перманганатом кали ацетона. При температуре кипени при размешивании сначала добавл ют 3 г бикарбоната натри в 15 мл воды, а затем 2 мл 20%-ной серной
кислоты, и кип т т в течение дальнейших 30 мин. Растворитель отгон ют, остаток разбавл ют водой, подщелачивают аммиаком и встр хивают с метиленхлоридом . После промывки, сушкн и выпаривани растворител остаетс сырой продукт, который выкристаллизовывают из этанола, и получают вышеуказанное соединение с точкой плавлени 24б-248°С и выходом 4,2 г (91,3% от теории).
Аналогично примера-м 1-3 получают соединени общей формулы (1) приведенные в таблице.
11
С)
Вг
12
Вг
С1
13
С1
Вг
241-242
134-135
218-222
14
С1
Вг
Вг
С1
15
16
Вг
CI
17
Вг
Вг
240-241
262-263
264
167-169
13
Вг
240-242
19
СН5С1
Вг
С1
-СНг-СНг-Л
Продолжение таблицы
180-182
хСН,
224-228
СН,
Claims (1)
- Формула изобретенияСпособ получения производных 1-пиперазинил-4Н-5-триазоло [3,4-с]тиено£2,3-е]1,4-диазепина общей формулы^!)R-N атомами углерода, фенил, толил, метоксифенил, галоидфёнил, нитрофенил или пиридил,' . R2· - водород, фтор; хлор или бром, R3 - хлор, бром или алкильный радикал , отличающийся тем, что соединение общей формулы(п.)R3 tгде R1 - водород, неразветленный или разветвленный алкильный, галоидалкильный, оксиалкильный или диалкиламиноалкильный радикал, незамещенные или замещенный метилом, метоксилом, нитрогруппой или галоидом фенильный радикал, пиридильный или пиримидильный радикал или остаток R2* -СО-, где означает водород, алкил с 1-17 атомами .углерода, алкоксил с 1-2R-NR2 (П)R\ Яги R3 имеют вышеуказанные где значения, подвергают дегидрированию.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772732943 DE2732943A1 (de) | 1977-07-21 | 1977-07-21 | Neue substituierte 1-piperazinyl- 4h-s-triazolo eckige klammer auf 3,4c eckige klammer zu thieno eckige klammer auf 2,3e eckige klammer zu 1,4-diazepine, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen |
| DE19772732921 DE2732921A1 (de) | 1977-07-21 | 1977-07-21 | Neue substituierte 1-acyl-piperidino- bzw. -piperazino-4h-s-triazolo eckige klammer auf 3,4c eckige klammer zu thieno eckige klammer auf 2,3e eckige klammer zu 1,4- diazepine, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU793402A3 true SU793402A3 (ru) | 1980-12-30 |
Family
ID=25772369
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2638749A SU725564A1 (ru) | 1977-07-21 | 1978-07-19 | Способ получени замещенных 1пиперазинил-4н- -триазоло/3,4-с/ тиено/2,3-е/-1,4-диазепинов или их солей |
| SU792746903A SU793402A3 (ru) | 1977-07-21 | 1979-04-04 | Способ получени производных 1-пиперазинил-4н- -триазоло/3,4с/-тиено/2,3е/-1,4-диазепина |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2638749A SU725564A1 (ru) | 1977-07-21 | 1978-07-19 | Способ получени замещенных 1пиперазинил-4н- -триазоло/3,4-с/ тиено/2,3-е/-1,4-диазепинов или их солей |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US4180573A (ru) |
| EP (1) | EP0000479B1 (ru) |
| JP (1) | JPS5422395A (ru) |
| AT (1) | AT363949B (ru) |
| AU (1) | AU515885B2 (ru) |
| CA (1) | CA1087182A (ru) |
| CH (1) | CH642374A5 (ru) |
| CS (1) | CS209897B2 (ru) |
| DD (1) | DD137934A5 (ru) |
| DE (1) | DE2860404D1 (ru) |
| DK (1) | DK150306C (ru) |
| ES (2) | ES471886A1 (ru) |
| FI (1) | FI63033C (ru) |
| FR (1) | FR2398070A1 (ru) |
| GB (1) | GB2001972B (ru) |
| GR (1) | GR65022B (ru) |
| HU (1) | HU176485B (ru) |
| IE (1) | IE47336B1 (ru) |
| IL (1) | IL55169A (ru) |
| IT (1) | IT1107490B (ru) |
| LU (1) | LU80002A1 (ru) |
| NL (1) | NL7807762A (ru) |
| NO (1) | NO149889C (ru) |
| NZ (1) | NZ187915A (ru) |
| PH (1) | PH14236A (ru) |
| PL (1) | PL115061B1 (ru) |
| PT (1) | PT68330A (ru) |
| RO (1) | RO75609A (ru) |
| SE (1) | SE439920B (ru) |
| SU (2) | SU725564A1 (ru) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2830782A1 (de) * | 1978-07-13 | 1980-01-24 | Boehringer Sohn Ingelheim | Neue substituierte 4h-s-triazolo eckige klammer auf 3,4c eckige klammer zu thieno eckige klammer auf 2,3e eckige klammer zu 1,4-diazepine, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen |
| EP0230942B1 (de) * | 1986-01-21 | 1992-04-29 | Boehringer Ingelheim Kg | Thieno-1,4-diazepine |
| CA2143246C (en) * | 1994-03-16 | 2000-08-22 | Thierry Godel | Imidazodiazepines |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH12303A (en) * | 1973-02-08 | 1979-01-16 | Hoffmann La Roche | Thienotriazolodiazepine derivatives |
| AT338799B (de) * | 1974-03-02 | 1977-09-12 | Boehringer Sohn Ingelheim | Verfahren zur herstellung neuer substituierter 6-aryl-4h-s-triazolo-(3,4c)-thieno-(2,3e)-1,4-diazepine und ihrer salze |
| US3894025A (en) * | 1974-03-21 | 1975-07-08 | Upjohn Co | 1-Piperazino-6-phenyl-4H-s-triazolo{8 4,3-a{9 {8 1,4{9 -benzodiazepine compounds |
| JPS5747916B2 (ru) * | 1974-05-13 | 1982-10-13 | ||
| DE2503235A1 (de) * | 1975-01-27 | 1976-07-29 | Boehringer Sohn Ingelheim | Neues verfahren zur herstellung von 8-brom-thieno-triazolo-1,4-diazepinen |
| DE2533924C3 (de) * | 1975-07-30 | 1979-05-03 | C.H. Boehringer Sohn, 6507 Ingelheim | Verfahren zur Herstellung von 6- Aryl-4H-striazolo [3,4-c] thieno [2,3-e] 1,4-diazepinen |
| DE2531678C3 (de) * | 1975-07-16 | 1979-06-28 | C.H. Boehringer Sohn, 6507 Ingelheim | Thieno [2,3e] triazole [3,4c] 5,6-dihydro-l,4diazepine und Verfahren zu ihrer Herstellung |
-
1978
- 1978-06-26 FI FI782025A patent/FI63033C/fi not_active IP Right Cessation
- 1978-06-28 DE DE7878100263T patent/DE2860404D1/de not_active Expired
- 1978-06-28 EP EP78100263A patent/EP0000479B1/de not_active Expired
- 1978-07-07 GR GR56728A patent/GR65022B/el unknown
- 1978-07-11 AT AT0498978A patent/AT363949B/de not_active IP Right Cessation
- 1978-07-13 US US05/924,149 patent/US4180573A/en not_active Expired - Lifetime
- 1978-07-17 PH PH21384A patent/PH14236A/en unknown
- 1978-07-18 CH CH772878A patent/CH642374A5/de not_active IP Right Cessation
- 1978-07-18 RO RO7894710A patent/RO75609A/ro unknown
- 1978-07-19 IT IT50381/78A patent/IT1107490B/it active
- 1978-07-19 LU LU80002A patent/LU80002A1/de unknown
- 1978-07-19 SU SU2638749A patent/SU725564A1/ru active
- 1978-07-19 CS CS784821A patent/CS209897B2/cs unknown
- 1978-07-19 IL IL55169A patent/IL55169A/xx unknown
- 1978-07-20 JP JP8889078A patent/JPS5422395A/ja active Granted
- 1978-07-20 PT PT68330A patent/PT68330A/pt unknown
- 1978-07-20 NO NO782499A patent/NO149889C/no unknown
- 1978-07-20 HU HU78BO1726A patent/HU176485B/hu unknown
- 1978-07-20 NZ NZ187915A patent/NZ187915A/xx unknown
- 1978-07-20 CA CA307,798A patent/CA1087182A/en not_active Expired
- 1978-07-20 NL NL7807762A patent/NL7807762A/xx not_active Application Discontinuation
- 1978-07-20 PL PL1978208542A patent/PL115061B1/pl unknown
- 1978-07-20 AU AU38209/78A patent/AU515885B2/en not_active Expired
- 1978-07-20 SE SE7808019A patent/SE439920B/sv not_active IP Right Cessation
- 1978-07-20 IE IE1456/78A patent/IE47336B1/en unknown
- 1978-07-20 ES ES471886A patent/ES471886A1/es not_active Expired
- 1978-07-20 DK DK325178A patent/DK150306C/da not_active IP Right Cessation
- 1978-07-20 DD DD78206830A patent/DD137934A5/xx unknown
- 1978-07-20 GB GB7830584A patent/GB2001972B/en not_active Expired
- 1978-07-21 FR FR7821744A patent/FR2398070A1/fr active Granted
- 1978-08-24 ES ES472812A patent/ES472812A1/es not_active Expired
-
1979
- 1979-04-04 SU SU792746903A patent/SU793402A3/ru active
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