SU728718A3 - Способ получени триазоло-тиено- диазепин-1-онов - Google Patents
Способ получени триазоло-тиено- диазепин-1-онов Download PDFInfo
- Publication number
- SU728718A3 SU728718A3 SU782683104A SU2683104A SU728718A3 SU 728718 A3 SU728718 A3 SU 728718A3 SU 782683104 A SU782683104 A SU 782683104A SU 2683104 A SU2683104 A SU 2683104A SU 728718 A3 SU728718 A3 SU 728718A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- ones
- diazepin
- triazolothieno
- preparing
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
- -1 alkali metal salt Chemical class 0.000 abstract description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052794 bromium Inorganic materials 0.000 abstract description 2
- 229910052801 chlorine Inorganic materials 0.000 abstract description 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 230000002082 anti-convulsion Effects 0.000 abstract 1
- 239000002249 anxiolytic agent Substances 0.000 abstract 1
- 230000000949 anxiolytic effect Effects 0.000 abstract 1
- 229940005530 anxiolytics Drugs 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052736 halogen Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229940125723 sedative agent Drugs 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- BWQYVHZSYJNLNK-UHFFFAOYSA-N thieno[3,2-c]diazepin-2-ylhydrazine Chemical compound N(N)N1N=C2C(=CC=C1)SC=C2 BWQYVHZSYJNLNK-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Description
Изобретение относитс к способу получени новых производных триазол тиенодиазепин-1-онов, обладающих ценными фармакологическими свойствами . Цель изобретени - получение но вых полезных соединений, расшир ющих арсенал средств воздействи на живой организм - достигаетс путем синтеза последних, основанного на известной реакции взаимодействи производных 2-.гидразино-ЗН (2 , 3-е) иено-1 ,4,-диазепина с фосгеном 1 Описываетс , согласно изобретен способ получени триазолотиенодиазепин-1-онов общей форму.лы I где R - атом хлора, брома или йода RU - водород или галоид. путем взаимодействи 2-гидразинотиенодиазепина общей формулы где Н, и R имеют указанные значени , с фосгеном. Целевой продукт выдел ют известными приемами. Обычно способ осуществл ют следующим образом: соединение гидразина раствор ют в инертном растворителе, например в толуоле, ксилоле, бензоле или хлористом углеводороде и подвергают взаимодействию с раствором фосгена в том же caMOMi растворителе или с газообразным фосгеном при температуре между и точкой кипени реакционной смеси. При этом фосген целесообразно добавл ть при комнатной температуре и затем смесь постепенно нагревать до точки кипени . Соединени общей форму.пы i известны и могут быть получены путем взаимодействи соответствующего 2-моркаптотиенодиазепина с гидразином.
Пример 1. 8-Бром-6-(o-xjiop фенил).-4Н.-3-триазоло (3, 4-с) тнено- (2 ,3-е),-1,4-диаэепин-1-он.
11 г (0,03 мол ) 7-бром-5-(о-зслорфенил ) 2-гидразино-ЗН- 2 , тиено-1 ,4 диазепина раствор ют в 250 г/ш толуола и затем смешивают со 100 мл 15%-ного раствора фосгена в толуоле. После одночасового размешивани при комнатной температуре и двухчасового размешивани при температуре кипени реакционный раствор после охпаж-дени встр хивают с насыщенным раствором карбоната натри . Органическую фазу после сушки упаривают и после перекристаллизации из метанола получают 0,1 т (77% от теоретического) целевого соединени с т.пл. 233-235
Диалогично приведенному в примерах 1 способу получают следующие соединени :
8-Хлор-б-(о-хлорфёнил)-4Н-Б-триазоло- (3,4-с)тиеноС2,3-eJ-1,4-диазе ПИН-1-он; Т.Ш1, 219-222 0
8 Бром-6-(о-бромфенил)4Н-3-триаэоло- 3 ,4-с1тиено(2,3-е)-1,4-диаэепин-1-он , т.пл. 212-214°С
8-Йод-б-(о-хлорфенил)-4Н-3-триазоло- (3,4-с)тиено(2.3-е)-1,4-диазе ПИН-1-ОН, т.пл. 2l5-2l7C
8 Хлор-б-фенил-4Н-8-триазоло{3 ,4-с)тиено(2,3-е)-1,4-диазепин-1-он, т.пл, 170-172°С
Claims (1)
1. Патент Великобритании №1346016, кл. С 07 d 99/06, опублик, 1974.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772708121 DE2708121A1 (de) | 1977-02-25 | 1977-02-25 | Triazolo-thieno-diazepin-l-one, verfahren zu ihrer herstellung und arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU728718A3 true SU728718A3 (ru) | 1980-04-15 |
Family
ID=6002117
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782582299A SU882411A3 (ru) | 1977-02-25 | 1978-02-22 | Способ получени триазоло-тиено-диазепин-1-онов или их солей |
| SU782683755A SU793401A3 (ru) | 1977-02-25 | 1978-11-10 | Способ получени производных триазолотиено-диазепин-1-она |
| SU782683104A SU728718A3 (ru) | 1977-02-25 | 1978-11-10 | Способ получени триазоло-тиено- диазепин-1-онов |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782582299A SU882411A3 (ru) | 1977-02-25 | 1978-02-22 | Способ получени триазоло-тиено-диазепин-1-онов или их солей |
| SU782683755A SU793401A3 (ru) | 1977-02-25 | 1978-11-10 | Способ получени производных триазолотиено-диазепин-1-она |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US4333944A (ru) |
| JP (1) | JPS53105497A (ru) |
| AT (1) | AT358050B (ru) |
| AU (1) | AU518863B2 (ru) |
| BE (1) | BE864318A (ru) |
| BG (1) | BG28577A3 (ru) |
| CA (1) | CA1070301A (ru) |
| CH (2) | CH641462A5 (ru) |
| CS (1) | CS203183B2 (ru) |
| DD (1) | DD135382A5 (ru) |
| DE (1) | DE2708121A1 (ru) |
| DK (1) | DK150487C (ru) |
| ES (2) | ES467292A1 (ru) |
| FI (1) | FI62839C (ru) |
| FR (1) | FR2381775A1 (ru) |
| GB (1) | GB1584906A (ru) |
| GR (1) | GR64419B (ru) |
| HU (1) | HU176483B (ru) |
| IE (1) | IE46425B1 (ru) |
| IL (1) | IL54120A (ru) |
| IT (1) | IT1102280B (ru) |
| LU (1) | LU79115A1 (ru) |
| NL (1) | NL7802084A (ru) |
| NO (1) | NO142839C (ru) |
| NZ (1) | NZ186559A (ru) |
| PH (1) | PH15987A (ru) |
| PL (1) | PL115163B1 (ru) |
| PT (1) | PT67707B (ru) |
| RO (1) | RO74147A (ru) |
| SE (1) | SE436205B (ru) |
| SU (3) | SU882411A3 (ru) |
| YU (1) | YU43978A (ru) |
| ZA (1) | ZA781085B (ru) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2708121A1 (de) * | 1977-02-25 | 1978-09-07 | Boehringer Sohn Ingelheim | Triazolo-thieno-diazepin-l-one, verfahren zu ihrer herstellung und arzneimittel |
| DE3829419C1 (ru) * | 1988-08-31 | 1989-12-28 | Accumulatorenwerke Hoppecke Carl Zoellner & Sohn Gmbh & Co Kg, 5790 Brilon, De | |
| CA2120939A1 (en) * | 1991-10-11 | 1993-04-15 | Tetsuya Tahara | Therapeutic agent for osteoporosis and diazepine compound |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE755139A (fr) * | 1969-08-21 | 1971-02-22 | Upjohn Co | Derives de benzodiazepinones, leurs intermediaires, et leur preparatio |
| JPS5418280B2 (ru) * | 1971-10-30 | 1979-07-06 | ||
| PH12303A (en) * | 1973-02-08 | 1979-01-16 | Hoffmann La Roche | Thienotriazolodiazepine derivatives |
| US4155913A (en) * | 1973-02-08 | 1979-05-22 | Hoffmann-La Roche Inc. | 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 |
| DE2708121A1 (de) * | 1977-02-25 | 1978-09-07 | Boehringer Sohn Ingelheim | Triazolo-thieno-diazepin-l-one, verfahren zu ihrer herstellung und arzneimittel |
-
1977
- 1977-02-25 DE DE19772708121 patent/DE2708121A1/de active Granted
-
1978
- 1978-02-02 FI FI780336A patent/FI62839C/fi not_active IP Right Cessation
- 1978-02-20 AT AT119478A patent/AT358050B/de not_active IP Right Cessation
- 1978-02-21 GR GR55505A patent/GR64419B/el unknown
- 1978-02-21 CS CS781092A patent/CS203183B2/cs unknown
- 1978-02-22 CH CH194978A patent/CH641462A5/de not_active IP Right Cessation
- 1978-02-22 SU SU782582299A patent/SU882411A3/ru active
- 1978-02-23 BG BG038796A patent/BG28577A3/xx unknown
- 1978-02-23 LU LU79115A patent/LU79115A1/de unknown
- 1978-02-23 IT IT48164/78A patent/IT1102280B/it active
- 1978-02-23 DD DD78203822A patent/DD135382A5/xx unknown
- 1978-02-23 IL IL54120A patent/IL54120A/xx unknown
- 1978-02-24 NZ NZ186559A patent/NZ186559A/xx unknown
- 1978-02-24 SE SE7802154A patent/SE436205B/sv not_active IP Right Cessation
- 1978-02-24 DK DK085078A patent/DK150487C/da active
- 1978-02-24 BE BE185480A patent/BE864318A/xx not_active IP Right Cessation
- 1978-02-24 ES ES467292A patent/ES467292A1/es not_active Expired
- 1978-02-24 JP JP2082178A patent/JPS53105497A/ja active Granted
- 1978-02-24 YU YU00439/78A patent/YU43978A/xx unknown
- 1978-02-24 IE IE405/78A patent/IE46425B1/en unknown
- 1978-02-24 NL NL7802084A patent/NL7802084A/xx not_active Application Discontinuation
- 1978-02-24 PT PT67707A patent/PT67707B/pt unknown
- 1978-02-24 ZA ZA00781085A patent/ZA781085B/xx unknown
- 1978-02-24 PL PL1978204882A patent/PL115163B1/pl unknown
- 1978-02-24 CA CA297,678A patent/CA1070301A/en not_active Expired
- 1978-02-24 HU HU78BO1701A patent/HU176483B/hu unknown
- 1978-02-24 FR FR7805383A patent/FR2381775A1/fr active Granted
- 1978-02-24 PH PH20819A patent/PH15987A/en unknown
- 1978-02-24 NO NO780636A patent/NO142839C/no unknown
- 1978-02-24 GB GB7524/78A patent/GB1584906A/en not_active Expired
- 1978-02-24 AU AU33602/78A patent/AU518863B2/en not_active Expired
- 1978-02-25 RO RO7893321A patent/RO74147A/ro unknown
- 1978-09-19 ES ES473465A patent/ES473465A1/es not_active Expired
- 1978-11-10 SU SU782683755A patent/SU793401A3/ru active
- 1978-11-10 SU SU782683104A patent/SU728718A3/ru active
-
1981
- 1981-02-10 US US06/233,294 patent/US4333944A/en not_active Expired - Fee Related
-
1982
- 1982-07-02 CH CH406582A patent/CH641182A5/de not_active IP Right Cessation
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