SU850007A3 - Способ получени производных имидазо/2,1-B/ТиАзОлидиНА - Google Patents
Способ получени производных имидазо/2,1-B/ТиАзОлидиНА Download PDFInfo
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- SU850007A3 SU850007A3 SU792831085A SU2831085A SU850007A3 SU 850007 A3 SU850007 A3 SU 850007A3 SU 792831085 A SU792831085 A SU 792831085A SU 2831085 A SU2831085 A SU 2831085A SU 850007 A3 SU850007 A3 SU 850007A3
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- USSR - Soviet Union
- Prior art keywords
- diazacyclopent
- general formula
- ring
- thia
- alk
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- 238000000034 method Methods 0.000 title claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 7
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical group C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 abstract 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 241000534944 Thia Species 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 6
- -1 2, 3-dihydrothiazole sulfoxide Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- DNQAQWCFLJOCNU-UHFFFAOYSA-N 4,5-bis[(4-methoxyphenyl)methyl]imidazolidine-2-thione Chemical compound C1=CC(OC)=CC=C1CC1C(CC=2C=CC(OC)=CC=2)NC(=S)N1 DNQAQWCFLJOCNU-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229950009928 thiazosulfone Drugs 0.000 description 1
Classifications
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- 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
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
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- 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
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/84—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D277/18—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
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- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/06—1,3-Thiazines; Hydrogenated 1,3-thiazines not condensed with other rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
.чаетс в том, что соединение общей формулы
Ar.vx-
::1т:.
Аг.
где Аг;| и Ar,j имеют вышеуказанные значени , подвергают взаимодействию с перекисью водорода или перйодатом.
Пример 1. 2г 5,6-ди-п-метоксифенил-2 ,3-дигидро-4Н-имидаэо f2, тиазола суспендируют в 33 мл этилового спирта и приготовленную суспензию смешивают в течение 5 мин с 7,01 МП 30%-ного раствора перекиси водорода. Реакционную смесь выдерживают в течение 90 мин при температуре ее кипени с обратным холодильником . Затем реакционную смесь охлаждают, выливают ее в 20 мл воды со льдом и производ т экстрагировани этиловым эфиром уксусной кислоты. Из состава полученного после упаривани экстракта, промытого водой и высушенного сернокислым натрием, получают после перекристаллизации 5,б-ди-п-метоксифенилимидазо 2 ,,3-дигидротиазолсульфоксид , т.пл. 1761770с .
Исходный материал может быть получен следующим образом,
2,5 г натри раствор ют в 220 мл этилового спирта. К полученному раствору прибавл ют 35 г 4,5-дианизилимидазолин-2-тиона . Получают суспензию . В течение 2 мин к этой суспензи прибавл ют по капл м при комнатной температуре (перемешивают) 15,7 мл 2-хлорэтанола. Реакционную смесь перемешивают в течение 1 ч при 609С и затем в течение 4 ч при температуре кипени с обратным холодильником. Непосредственно после этого слабую суспензию упаривают досуха. Остаток подвергают очистке при помощи ацетона/воды . Получают 4,5-ди-(п-метокс фенил) -2 -|Ь-оксиэтилмеркаптоимидазол.
14,8 г 4,5-ди-(п-метоксифенил)-2-l -oкcиэтилмepкaптoимидaзoлa раствор ют в 50 мл абсолютного пиридина и при перемешивании и температуре приблизительно внутри реакционного сосуда к раствору прибавл ют по капл м 15,8 г бензолсульфохлорида в 60 мл абсолютного пиридина. Непосредственно после этого реакционную смесь перемешивают в течение 60 ч. при температуре 0°С. Затем реакционную смесь выливают в воду со льдом и производ т экстрагирование дихлорметаном . Объединенные и промытые водой три раза дихлорметановые экстракты сушат сернокислым натрием и эатем упаривают досуха. В зкий маслообразный продукт кристаллизуют из смеси
толуола и петролейного эфира. Полу- ченный указанным способом 5,6-ди- (п-метоксифенил)-имидазо 2,1-Ь -дигидротиазол имеет т.пл. 152-154с.
Пример 2. 0,5 г 5,6-ди-п-метоксифенил-2 ,3-дигидро-4Н-имидазо 12,1-Ь тиазола суспендируют в 1,5 мл лед ной уксусной кислоты и приготовленную суспензию смешивают с 0,9 мл 30%-ного раствора перекиси водорода. Реакционную смесь перемешивают в течение 7 ч при , затем выливают ее в воду со льдом и производ т экстрагирование этиловым эфиром уксусной кислоты. Органическую фазу промывают 1 н. раствором гидроокиси натри до тех пор, пока экстракт не становитс основным. После этого органическую фазу промывают водой и раствором соли до нейтральной реакции промывных вод, сушат сернокислым натрием и затем упаривают. Остаток кристаллизуют из этилового эфира уксусной кислоты, после чего полученный продукт перекристаллизовывают из смеси этилового эфира уксусной кислоты и петролейного эфира.
В результате получают 5,6-ди-пметоксифенилимидазо 2,1-Ь}-дигидротиазолсульфона с т .пл. 186-1870С. Аношогичным образом получают: 6-(п-метоксифенил )-5-.(4-пиридил )-2, 3-дигидро-имидазо 2 ,1-ь тиазолсульфоксид , т.пл. 165-170С, 6-(п-фторфенил )-5-4-пиридил-2,3-дигидро-имидазо 2,1-Ь тиазолсульфоксид, т.пл. 229231 С , 5,6-ди- (2-пиридил)-2, 3-дигидро-имидазо 2 ,1-Ь тиазолсульфоксид, т.пл. 199-2000С.
Claims (1)
- Формула изобретениСпособ получени производных имидазо 2,1-Ь тиазолидина общей формулы I1°)п.где кольцо 1,З-диазациклопент-2-ена . может иметь дополнительную двойную св зь, Аг и Аг независимо друг от друга означают, в соответствующем 55 случае, замещенный низшим алкоксилом или галогеном фенил или пиридил и п означает 1 или 2, отличаюш; и. и с тем, что соединение общей формулы IImr где Аг и Аг имеют вышеуказанные значени , подвергают взаимодействию с перекисью водорода или периодатом . Источники информации, прин тые во викмание при экспертизе 1. патент СССР 492090. кл. С 07 О 513/04, опублик. 1976.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU77703A LU77703A1 (de) | 1977-07-07 | 1977-07-07 | Verfahren zur herstellung von bicyclischen thia-diaza-verbindungen |
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| Publication Number | Publication Date |
|---|---|
| SU850007A3 true SU850007A3 (ru) | 1981-07-23 |
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ID=19728633
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782632647A SU873886A3 (ru) | 1977-07-07 | 1978-07-06 | Способ получени прозводных имидазо (2,1-в)тиазола или их солей в виде смеси изомеров или отдельных изомеров |
| SU792763599A SU893134A3 (ru) | 1977-07-07 | 1979-05-18 | Способ получени имидазо-2,1-8-тиазолин-или-тиазин-производных в виде смеси или отдельных изомеров или их кислотно-аддитивных солей |
| SU792831085A SU850007A3 (ru) | 1977-07-07 | 1979-10-23 | Способ получени производных имидазо/2,1-B/ТиАзОлидиНА |
| SU792855458A SU873887A3 (ru) | 1977-07-07 | 1979-12-20 | Способ получени производных имидазо/2,1-в/тиазолина или имидазо /2,1-в/тиазина или их кислотно-аддитивных солей,в виде смеси изомеров или отдельных изомеров |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782632647A SU873886A3 (ru) | 1977-07-07 | 1978-07-06 | Способ получени прозводных имидазо (2,1-в)тиазола или их солей в виде смеси изомеров или отдельных изомеров |
| SU792763599A SU893134A3 (ru) | 1977-07-07 | 1979-05-18 | Способ получени имидазо-2,1-8-тиазолин-или-тиазин-производных в виде смеси или отдельных изомеров или их кислотно-аддитивных солей |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU792855458A SU873887A3 (ru) | 1977-07-07 | 1979-12-20 | Способ получени производных имидазо/2,1-в/тиазолина или имидазо /2,1-в/тиазина или их кислотно-аддитивных солей,в виде смеси изомеров или отдельных изомеров |
Country Status (18)
| Country | Link |
|---|---|
| EP (3) | EP0000353A3 (ru) |
| JP (1) | JPS5416470A (ru) |
| AR (2) | AR222309A1 (ru) |
| AU (1) | AU3778878A (ru) |
| DD (2) | DD138212A5 (ru) |
| DK (1) | DK305578A (ru) |
| ES (4) | ES471458A1 (ru) |
| FI (1) | FI782132A7 (ru) |
| GR (1) | GR64978B (ru) |
| IL (1) | IL55086A0 (ru) |
| IT (1) | IT8149647A0 (ru) |
| LU (1) | LU77703A1 (ru) |
| NO (1) | NO782357L (ru) |
| NZ (1) | NZ187789A (ru) |
| PL (1) | PL116596B1 (ru) |
| PT (1) | PT68246A (ru) |
| SU (4) | SU873886A3 (ru) |
| ZA (1) | ZA783898B (ru) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CY1302A (en) * | 1978-04-11 | 1985-12-06 | Ciba Geigy Ag | Mercapto-imidazole derivatives,their preparation,their pharmaceutical compositions and applications |
| DE2823197A1 (de) * | 1978-05-24 | 1979-11-29 | Schering Ag | Neue imidazolderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| US4175127A (en) * | 1978-09-27 | 1979-11-20 | Smithkline Corporation | Pyridyl substituted 2,3-dihydroimidazo[2,1-b]thiazoles |
| PL221188A1 (ru) * | 1979-01-05 | 1980-12-01 | Ciba Geigy Ag | |
| US4636516A (en) * | 1981-02-19 | 1987-01-13 | Yamanouchi Pharmaceutical Co., Ltd. | 3,5-di-tert-butyl-4-hydroxyphenyl-substituted heterocyclic compounds |
| IL78834A (en) * | 1985-05-23 | 1992-07-15 | Smithkline Beckman Corp | 2,3-dihydro-5-(1,4-dihydropyridin-4-yl)-6-phenylimidazo(2,1-b)thiazoles and 6,7-dihydro-3-(1,4-dihydropyridin-4-yl)-2-phenyl-5h-imidazo(2,1-b)(1,3)thiazines and their use as intermediates in a process for preparing the corresponding pyridyl-substituted imidazo(2,1-b)thiazoles and 5h-imidazo(2,1-b)(1,3)thiazines |
| US5008390A (en) * | 1985-05-23 | 1991-04-16 | Smithkline Beckman Corporation | Compounds for preparing 6-phenyl-2,3-dihydroimidazo[2,1-b]-thiazoles and corresponding thiazines |
| US4803279A (en) * | 1985-05-23 | 1989-02-07 | Smithkline Beckman Corporation | 1.4-dihydro-4-pyridyl-substituted imidazo (2,1-b) thiazoles and the corresponding thiazines. |
| US4719218A (en) * | 1985-12-12 | 1988-01-12 | Smithkline Beckman Corporation | Pyrrolo[1,2-a]imidazole and pyrrolo[1,2-a]pyridine derivatives and their use as 5-lipoxygenase pathway inhibitor |
| ZW24186A1 (en) * | 1985-12-12 | 1987-07-08 | Smithkline Beckman Corp | Inhibition of the 5-lipoxygenase pathway |
| KR920702621A (ko) * | 1989-06-13 | 1992-10-06 | 스튜어트 알. 슈터 | 단핵세포 및/또는 마크로파지에 의한 인터루킨-1 또는 종양회사인자 생성의 억제 |
| GB9005966D0 (en) * | 1990-03-16 | 1990-05-09 | May & Baker Ltd | New compositions of matter |
| GB9019838D0 (en) * | 1990-09-11 | 1990-10-24 | Smith Kline French Lab | Compounds |
| CA2063865A1 (en) * | 1992-03-24 | 1993-09-25 | Karoly Lempert | 2-(substituted imino)-thiazolidines and process for the preparation thereof |
| US5552422A (en) * | 1995-01-11 | 1996-09-03 | Merck Frosst Canada, Inc. | Aryl substituted 5,5 fused aromatic nitrogen compounds as anti-inflammatory agents |
| RU2405788C1 (ru) * | 2009-07-14 | 2010-12-10 | Государственное образовательное учреждение высшего профессионального образования "БАШКИРСКИЙ ГОСУДАРСТВЕННЫЙ МЕДИЦИНСКИЙ УНИВЕРСИТЕТ ФЕДЕРАЛЬНОГО АГЕНТСТВА ПО ЗДРАВООХРАНЕНИЮ И СОЦИАЛЬНОМУ РАЗВИТИЮ" | ДИГИДРОХЛОРИД 3-ЦИКЛОГЕКСИЛАМИНОМЕТИЛТИАЗОЛО[3,2-a]БЕНЗИМИДАЗОЛА, ПРОЯВЛЯЮЩИЙ ИММУНОТРОПНУЮ И АНТИАГРЕГАЦИОННУЮ АКТИВНОСТЬ |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2981739A (en) * | 1958-01-27 | 1961-04-25 | Diamond Alkali Co | Certain alpha-haloaldehyde addition products of ethylenethioureas and process |
| NL131034C (ru) * | 1964-05-11 | |||
| US3297708A (en) * | 1965-10-06 | 1967-01-10 | American Cyanamid Co | Method of preparing thiazolidines |
| US3455924A (en) * | 1967-02-08 | 1969-07-15 | Upjohn Co | Dianisylimidazoles |
| NL164285C (nl) * | 1968-01-09 | 1980-12-15 | Rhone Poulenc Sa | Werkwijze ter bereiding van een farmaceutisch preparaat, dat een imidazoÿ2.1-bÿthiazoolderivaat bevat, de gevormde farmaceutische preparaten, alsmede werkwijze voor het bereiden van dit imidazoÿ2.1-bÿthiazoolderivaat. |
| BE788792A (fr) * | 1971-09-30 | 1973-03-13 | Ici Ltd | Procedes et compositions a usage anti-bacterien |
| US3842097A (en) * | 1973-01-22 | 1974-10-15 | Searle & Co | 2-(phenoxyalkylthio)imidazoles and congeners |
| SE428686B (sv) * | 1975-08-11 | 1983-07-18 | Du Pont | Forfarande for framstellning av antiinflammatoriskt aktiva imidazoler |
| GB1541321A (en) * | 1976-03-10 | 1979-02-28 | Metabio | 2,3-dihydroimidazo(2,1-b)thiazole derivatives and process for their preparation |
| US4064260A (en) * | 1976-07-29 | 1977-12-20 | E. I. Du Pont De Nemours And Company | Anti-inflammatory diarylimidazothiazoles and their corresponding S-oxides |
| US4263311A (en) * | 1976-09-27 | 1981-04-21 | Smithkline Corporation | 5,6-Phenyl-2,3-dihydroimidazo [2,1-b] thiazoles |
-
1977
- 1977-07-07 LU LU77703A patent/LU77703A1/de unknown
-
1978
- 1978-06-29 EP EP78100272A patent/EP0000353A3/xx not_active Withdrawn
- 1978-06-29 EP EP80101323A patent/EP0019688A1/de not_active Ceased
- 1978-06-29 EP EP80101322A patent/EP0020858A1/de not_active Withdrawn
- 1978-07-03 PT PT68246A patent/PT68246A/pt unknown
- 1978-07-03 FI FI782132A patent/FI782132A7/fi not_active Application Discontinuation
- 1978-07-05 ES ES471458A patent/ES471458A1/es not_active Expired
- 1978-07-05 IL IL55086A patent/IL55086A0/xx unknown
- 1978-07-05 AU AU37788/78A patent/AU3778878A/en active Pending
- 1978-07-05 GR GR56695A patent/GR64978B/el unknown
- 1978-07-05 AR AR272843A patent/AR222309A1/es active
- 1978-07-06 DD DD78206565A patent/DD138212A5/xx unknown
- 1978-07-06 NO NO782357A patent/NO782357L/no unknown
- 1978-07-06 SU SU782632647A patent/SU873886A3/ru active
- 1978-07-06 JP JP8153378A patent/JPS5416470A/ja active Pending
- 1978-07-06 DD DD78214990A patent/DD145538A5/de unknown
- 1978-07-06 DK DK783055A patent/DK305578A/da unknown
- 1978-07-06 ZA ZA00783898A patent/ZA783898B/xx unknown
- 1978-07-06 NZ NZ187789A patent/NZ187789A/xx unknown
- 1978-07-07 PL PL1978208253A patent/PL116596B1/pl unknown
-
1979
- 1979-03-05 ES ES478296A patent/ES478296A1/es not_active Expired
- 1979-05-18 SU SU792763599A patent/SU893134A3/ru active
- 1979-09-10 ES ES484033A patent/ES484033A1/es not_active Expired
- 1979-09-20 ES ES484327A patent/ES484327A1/es not_active Expired
- 1979-10-23 SU SU792831085A patent/SU850007A3/ru active
- 1979-12-03 AR AR279136A patent/AR224381A1/es active
- 1979-12-20 SU SU792855458A patent/SU873887A3/ru active
-
1981
- 1981-11-06 IT IT8149647A patent/IT8149647A0/it unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL208253A1 (pl) | 1979-06-04 |
| EP0000353A2 (de) | 1979-01-24 |
| IL55086A0 (en) | 1978-09-29 |
| AR222309A1 (es) | 1981-05-15 |
| LU77703A1 (de) | 1979-03-26 |
| PL116596B1 (en) | 1981-06-30 |
| EP0019688A1 (de) | 1980-12-10 |
| FI782132A7 (fi) | 1979-01-08 |
| IT8149647A0 (it) | 1981-11-06 |
| SU873887A3 (ru) | 1981-10-15 |
| NZ187789A (en) | 1981-03-16 |
| PT68246A (en) | 1978-08-01 |
| ES484327A1 (es) | 1980-05-16 |
| GR64978B (en) | 1980-06-11 |
| AR224381A1 (es) | 1981-11-30 |
| DD138212A5 (de) | 1979-10-17 |
| EP0000353A3 (en) | 1979-06-13 |
| SU873886A3 (ru) | 1981-10-15 |
| ES484033A1 (es) | 1980-04-16 |
| EP0020858A1 (de) | 1981-01-07 |
| ES471458A1 (es) | 1979-10-01 |
| DD145538A5 (de) | 1980-12-17 |
| ES478296A1 (es) | 1979-05-16 |
| JPS5416470A (en) | 1979-02-07 |
| NO782357L (no) | 1979-01-09 |
| AU3778878A (en) | 1980-01-10 |
| SU893134A3 (ru) | 1981-12-23 |
| DK305578A (da) | 1979-01-08 |
| ZA783898B (en) | 1979-07-25 |
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