SU561508A3 - Способ получени производных 2-бензоил3-(аминоацетиламидо)-пиридина или их солей - Google Patents
Способ получени производных 2-бензоил3-(аминоацетиламидо)-пиридина или их солейInfo
- Publication number
- SU561508A3 SU561508A3 SU2043813A SU2043813A SU561508A3 SU 561508 A3 SU561508 A3 SU 561508A3 SU 2043813 A SU2043813 A SU 2043813A SU 2043813 A SU2043813 A SU 2043813A SU 561508 A3 SU561508 A3 SU 561508A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- benzoyl
- amino
- acetylamido
- salts
- preparing
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title 1
- 238000002474 experimental method Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- -1 (ethylaminoacetyl amide) 6 - chloropyridine Chemical compound 0.000 description 1
- SYZRZLUNWVNNNV-UHFFFAOYSA-N 2-bromoacetyl chloride Chemical compound ClC(=O)CBr SYZRZLUNWVNNNV-UHFFFAOYSA-N 0.000 description 1
- AULWPXHFRBLPAE-UHFFFAOYSA-N 6-chloropyridine Chemical compound ClC1=C=CC=C[N]1 AULWPXHFRBLPAE-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
натром, или действием разбавлеш1Ь Х кислот, например разбавленной уксусной кислоты.
П р и м е р 1. 2 Бензоил 3 - (аминоацетиламадо ) 6 - хлорпиридин.
100 г 2 - бензоил - 3 - бромацетиламидо - 6 «лорпиридина прибавл ют к 400 мл жидкого аммиака при перемеилшании. Смесь перемешивают 4 час при -40° С, затем упаривают аммиак. Твердый остаток раствор ют в 400 мл хлористого метилена и раствор промьтают один раз 400 мл воды. ОрганиЧЕСкий слой сушат и при перемешивании смешивают с 400 мл бензина, при этом осаждаетс требуемый продукт. Выход 50 г, т.пл. 200-201°С.
Исходное вещество получают следующим образом: в раствор 312 г 2-бензоил-3 - амшю - 6 хлоргеиридина в 1250мл ацетона прибавл ют по капл м Б течение 15 мин 135 мл бромацетилхлорида при охлаждении льдом. Через некоторое врем вьтристаллизовьшаетс продукт реакции, который через 2 час отфильтровывают. Выход 363 г, Т.Ш1. 128°С,
Пример 2. 2- Бензоил - 3 (этиламиноацетиламвдо ) 6 - хлорпиридин.
В смесь 50 г этиламина и 150 мл метанола прибавл ют при комнатной температуре 34,4 г 2 бензоил 3 - бромацетиламндо - 6 хлорпиридищ при перемешивании. TeNmeparypa повьшгаетс до 30°С. Перемешивают 1 час, отфильтровывают .рсадс (к,д)аствор ют в диоксане, смешивают с 6 и. зтанольным раствором хлористого водорода, гид.рохлорид отфильтровьгоают и промьшают диоксаном . Выход 23,8 г, т.пл. 196-200°С.
Claims (1)
1. Вейганд-Х льгетаг. Методы эксперимента в органической химии. М., Хнню , 1968, с. 413.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT411372A AT321303B (de) | 1972-05-10 | 1972-05-10 | Verfahren zur Herstellung von neuen 2-Benzoyl-3-amino-pyridin-Verbindungen und deren Salzen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU561508A3 true SU561508A3 (ru) | 1977-06-05 |
Family
ID=3559825
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1914703A SU538662A3 (ru) | 1972-05-10 | 1973-04-26 | Способ получени производных 2-бензоил-3-аминопиридина или их солей |
| SU742043814A SU597338A3 (ru) | 1972-05-10 | 1974-06-17 | Способ получени производных 2-бензоил-3-амино-6-галоидпиридинов или их солей |
| SU2043813A SU561508A3 (ru) | 1972-05-10 | 1974-07-17 | Способ получени производных 2-бензоил3-(аминоацетиламидо)-пиридина или их солей |
| SU742043816A SU677653A3 (ru) | 1972-05-10 | 1974-07-17 | Способ получени 2-бензоил-3аминопиридинов или их солей |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1914703A SU538662A3 (ru) | 1972-05-10 | 1973-04-26 | Способ получени производных 2-бензоил-3-аминопиридина или их солей |
| SU742043814A SU597338A3 (ru) | 1972-05-10 | 1974-06-17 | Способ получени производных 2-бензоил-3-амино-6-галоидпиридинов или их солей |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU742043816A SU677653A3 (ru) | 1972-05-10 | 1974-07-17 | Способ получени 2-бензоил-3аминопиридинов или их солей |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3875176A (ru) |
| JP (1) | JPS4948674A (ru) |
| AR (2) | AR207633Q (ru) |
| AT (1) | AT321303B (ru) |
| AU (1) | AU469111B2 (ru) |
| BE (1) | BE799339A (ru) |
| CA (1) | CA991189A (ru) |
| CH (2) | CH605761A5 (ru) |
| CS (1) | CS181238B2 (ru) |
| DD (1) | DD106378A5 (ru) |
| DE (1) | DE2319872A1 (ru) |
| EG (1) | EG11137A (ru) |
| ES (3) | ES413173A1 (ru) |
| FR (1) | FR2184077B1 (ru) |
| GB (1) | GB1416459A (ru) |
| HU (1) | HU169037B (ru) |
| IL (1) | IL42007A (ru) |
| NL (1) | NL7306170A (ru) |
| PL (1) | PL91935B1 (ru) |
| RO (1) | RO63441A (ru) |
| SE (1) | SE415974B (ru) |
| SU (4) | SU538662A3 (ru) |
| ZA (1) | ZA732013B (ru) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4007290A (en) * | 1974-01-09 | 1977-02-08 | General Foods Corporation | Caffeine antagonim |
| DE3067662D1 (en) * | 1980-01-16 | 1984-06-07 | Lacer Sa | New 2-halo-pyridines, their production and pharmaceutical compositions |
| JPH01104580U (ru) * | 1988-01-05 | 1989-07-14 | ||
| JP2531989B2 (ja) * | 1988-09-14 | 1996-09-04 | 吉富製薬株式会社 | ピリジン化合物 |
| RU2255088C2 (ru) * | 2001-02-09 | 2005-06-27 | Исихара Сангио Кайся, Лтд. | Производное бензоилпиридина или его соль, содержащий его в качестве активного ингредиента фунгицид, способы его получения и промежуточные соединения для его получения |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3781360A (en) * | 1966-01-14 | 1973-12-25 | Schering Corp | 2-polyfluoroloweralkylamino benzophenones |
| US3763178A (en) * | 1968-09-05 | 1973-10-02 | American Home Prod | Imidazolinyl phenyl carbonyl acid addition salts and related compounds |
-
1972
- 1972-05-10 AT AT411372A patent/AT321303B/de not_active IP Right Cessation
-
1973
- 1973-01-01 AR AR251133A patent/AR207633Q/es unknown
- 1973-03-22 ZA ZA732013A patent/ZA732013B/xx unknown
- 1973-03-27 DD DD169761A patent/DD106378A5/xx unknown
- 1973-03-30 ES ES413173A patent/ES413173A1/es not_active Expired
- 1973-03-30 ES ES413174A patent/ES413174A1/es not_active Expired
- 1973-03-30 ES ES413175A patent/ES413175A1/es not_active Expired
- 1973-04-03 US US347361A patent/US3875176A/en not_active Expired - Lifetime
- 1973-04-11 IL IL42007A patent/IL42007A/en unknown
- 1973-04-19 DE DE2319872A patent/DE2319872A1/de not_active Withdrawn
- 1973-04-26 SU SU1914703A patent/SU538662A3/ru active
- 1973-05-03 NL NL7306170A patent/NL7306170A/xx not_active Application Discontinuation
- 1973-05-07 CH CH381676A patent/CH605761A5/xx not_active IP Right Cessation
- 1973-05-07 CH CH643373A patent/CH582150A5/xx not_active IP Right Cessation
- 1973-05-08 EG EG168/73A patent/EG11137A/xx active
- 1973-05-08 PL PL1973162405A patent/PL91935B1/pl unknown
- 1973-05-08 CS CS7300003271A patent/CS181238B2/cs unknown
- 1973-05-09 BE BE6044150A patent/BE799339A/xx unknown
- 1973-05-09 RO RO7300074727A patent/RO63441A/ro unknown
- 1973-05-09 HU HUDE817A patent/HU169037B/hu unknown
- 1973-05-10 GB GB2229873A patent/GB1416459A/en not_active Expired
- 1973-05-10 SE SE7306625A patent/SE415974B/xx unknown
- 1973-05-10 FR FR7316947A patent/FR2184077B1/fr not_active Expired
- 1973-05-10 CA CA170,937A patent/CA991189A/en not_active Expired
- 1973-05-10 AR AR247950A patent/AR201105A1/es active
- 1973-05-10 AU AU55537/73A patent/AU469111B2/en not_active Expired
- 1973-05-10 JP JP48052056A patent/JPS4948674A/ja active Pending
-
1974
- 1974-06-17 SU SU742043814A patent/SU597338A3/ru active
- 1974-07-17 SU SU2043813A patent/SU561508A3/ru active
- 1974-07-17 SU SU742043816A patent/SU677653A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| EG11137A (en) | 1978-06-30 |
| CH582150A5 (ru) | 1976-11-30 |
| JPS4948674A (ru) | 1974-05-11 |
| AT321303B (de) | 1975-03-25 |
| FR2184077A1 (ru) | 1973-12-21 |
| SU677653A3 (ru) | 1979-07-30 |
| AR201105A1 (es) | 1975-02-14 |
| RO63441A (fr) | 1978-05-15 |
| CH605761A5 (ru) | 1978-10-13 |
| BE799339A (fr) | 1973-11-09 |
| US3875176A (en) | 1975-04-01 |
| AR207633Q (es) | 1976-10-22 |
| SE415974B (sv) | 1980-11-17 |
| HU169037B (ru) | 1976-09-28 |
| ZA732013B (en) | 1974-04-24 |
| AU469111B2 (en) | 1976-02-05 |
| IL42007A0 (en) | 1973-06-29 |
| CS181238B2 (en) | 1978-03-31 |
| NL7306170A (ru) | 1973-11-13 |
| ES413173A1 (es) | 1976-01-16 |
| GB1416459A (en) | 1975-12-03 |
| SU597338A3 (ru) | 1978-03-05 |
| IL42007A (en) | 1977-06-30 |
| CA991189A (en) | 1976-06-15 |
| PL91935B1 (ru) | 1977-03-31 |
| DE2319872A1 (de) | 1973-11-22 |
| ES413174A1 (es) | 1976-01-16 |
| ES413175A1 (es) | 1976-06-01 |
| FR2184077B1 (ru) | 1976-07-02 |
| AU5553773A (en) | 1974-11-14 |
| DD106378A5 (ru) | 1974-06-12 |
| SU538662A3 (ru) | 1976-12-05 |
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