SU1277899A3 - Способ получени производных пирроло (1,2- @ )тиазола - Google Patents
Способ получени производных пирроло (1,2- @ )тиазола Download PDFInfo
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- SU1277899A3 SU1277899A3 SU843821206A SU3821206A SU1277899A3 SU 1277899 A3 SU1277899 A3 SU 1277899A3 SU 843821206 A SU843821206 A SU 843821206A SU 3821206 A SU3821206 A SU 3821206A SU 1277899 A3 SU1277899 A3 SU 1277899A3
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- USSR - Soviet Union
- Prior art keywords
- temperature
- pyrrolo
- thiazole
- kpa
- reduced pressure
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- AAUBAPMXIKRIIH-UHFFFAOYSA-N 1,3-dihydropyrrolo[1,2-c][1,3]thiazole Chemical class C1=CC=C2CSCN21 AAUBAPMXIKRIIH-UHFFFAOYSA-N 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- -1 pyrrolo (1 Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- 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
-
- 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
-
- 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
- C07D213/55—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/06—1,3-Thiazines; Hydrogenated 1,3-thiazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
СПОСОБ ПО ТУЧЕНИЯ ПРОИЗВОДНЫХ ПИРРОЛО
Description
1Ю
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ы Изобретение относитс к спосооу получени новых химических соединений , а именно производных пирроло (1,2-с).тиазола, вл ющихс полупродуктами в синтезе веществ с биологической активностью. Цель изобретени - получение новых соединений в качестве полупродуктов в синтезе биологически активных пирроло( 1 , 2-с)тиазол)в с новым видом биологического действи в этом р ду. Пример 1.48г 3-(3-пиpидилJ lH,ЗH-пиppoлo( 1,2-с)-7-тиазолкарбонитрила добавл ют в раствор 41,7 г гидроокиси кали в таблетках в 400 см этиленгликол . Реакционную смесь нагревают до температуры, близ кой к 150°С, которую поддерживают в течение 6 ч 30 мин. В течение 16 ч перемешивают при температуре, близкой к 20°С. Растворитель выпаривают при пониженном давлении (5 мм рт.ст 0,7 кПа) при температуре, близкой к 100°С. Остаток раствор ют в 380 см дистиллированной воды. В полученный раствор добавл ют 0,5 г растительной сажи, затем раствор фильтруют и его рН довод т, до 4 при помощи добавлени концентрированного водного раствора сол ной кислоты, поддержива температуру близкой к 20°С. Образующиес кристаллы отдел ют фильтрацией , промьшают 3 раза в 600 см- дистиллированной воды, затем сушат при пониженном давлении (20 мм рт.ст 2,7 кПа) при температуре, близкой к 20°С, в присутствии гидроокиси кали в таблетках. Таким образом по лучают 49,5 г неочищенного продукта плав щегос при температуре 177°С. Этот продукт раствор ют в 840 см кип щего этанола. В полученный раст вор добавл ют 0,5 г растительной сажи, затем раствор фильтруют в гор чем состо нии, фильтрат охлаждают до температуры, близкой к 4°С, кото рую поддерживают в течение 1 ч. Образующиес кристаллы отдел ют фильт рацией, промывают 3 раза в 45 см этанола, охлажденного до температуры , близкой к 4С, затем 3 раза в 90 см диэтилового простого эфира и сушат при пониженном давлении (20 мм рт.ст.; 2,7 кПа) при темпера туре, близкой к , в присутствии гидроокиси кали в таблетках. Таким образом получают 36,6 г 3-(3-пиридил )-1Н,ЗН-пирроло(,2-е 7-тиазолкарбоновой кислоты в виде кристаллов кремового цвета, плав щихс при . И р и м е р 2. Смесь 18,7 г 5-(3пиридил )-1Ы,ЗН-пирроло(1,2-с)-7-тиазолкарбонитрила , 16,3 г гидроокиси кали в виде таблеток и 160 см этиленгликол нагревают при перемешивании при температуре около 155 С в течение 2 ч. После 16 ч перемешивани при температуре около растворитель выпаривают при пониженном давлении (2 мм рт.ст.; 0,27 кПа) при температуре около 100°С. Остаток раствор ют в 100 см дистиллированной воды, а рН полученного раствора довод т до 5 путем присоединени водного раствора 211 сол ной кислоты. По вившиес ..кристаллы отдел ют путем фильтровани , промывают 3 раза в 150 см дистиллирова5шой воды, затем 3 раза в 150 см ацетона и сушат при пониженном давлении (20 мм рт.ст, 2,7 кПа) п.ри температуре около 20°С в присутствии гидроокиси кали в виде таблеток. Таким образом получают 17,7 г неочищенного соединени , плав щегос при температуре 264°С. Это соединение соедин ют с 1,3 г соединени , полученного на предыдущей стадии, и раствор ют в смеси 650 см -бутанола и 150 см диметилформамида , предварительно нагретой до температуры около 115°С. Прибавл ют 0,5 г растительной сажи к полученному раствору и на тепле фильтруют. Ф 1льтрат охлаж.дают до температуры около 4°С в течение 16 ч. Образовавшиес кристаллы отдел ют фильтрованием , дважды промывают 50 см диметилформамида , трехкратно в 150 см этанола , трехкратно в 150 см изопропилового эфира, затем трехкратно в 150 см простого диэтилового эфира, после чего сушат при пониженном давлении (20 мм рт.ст.; 2,7 кПа) при температуре около в присутствии гид,роокиси кали в виде таблеток. Таким обрз.зом получают 16,1 г соединени , плав щегос при температуре . С помощью 250 см дистиллированной Bo/:tbi это соединение перевод т в суспензию, которую перемешивают при температуре около 20°С в течение 2 ч. Кристаллы отдел ют путем фильтровани , промывают в 150 см дистиллированной воды (п тикратное промывание, трехкратно промывают в 90 см этанола, трехкратно в 90 смизопропилового эфира и трехкратно в 90 см: диэтилового эфира, сушат при пониженном давлении (20 мм рт.ст. 5 2,7 кПа) при температуре около 100°С в присутствии гидроокиси кали в виде-таблеток. Таким образом получают 15,5 г 5-,{3 пиридил)-1Н,ЗН-пирроло (1 ,2-с)-7-тиазолкарбоновой кислоты , имеющей вид кремовых кристаплов ,плав щихс при температуре 266 .
Claims (1)
- СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ ПИРРОЛО(1,2-с)ТИАЗОЛА формулыС00Н где один из Р^и Р.^ - атом водорода, а другой - 3—пиридил, отличающийся тем, что соединение формулыCN где Rή и R^ имеют указанные значения, подвергают гидролизу путем нагревания при температуре 150°С в щелочной среде в присутствии этиленгликоля.СО с1277899 АЗ
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8300453A FR2541280B1 (fr) | 1983-01-13 | 1983-01-13 | Nouveaux derives du 1h, 3h-pyrrolo (1,2c) thiazolecarboxamide-7, leur preparation et les medicaments qui les contiennent |
| FR8300454A FR2539417A1 (fr) | 1983-01-13 | 1983-01-13 | Nouveaux pyrrolo-1, 2 heterocycles, leur preparation et les medicaments qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1277899A3 true SU1277899A3 (ru) | 1986-12-15 |
Family
ID=26223238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU843821206A SU1277899A3 (ru) | 1983-01-13 | 1984-12-07 | Способ получени производных пирроло (1,2- @ )тиазола |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4539400A (ru) |
| EP (1) | EP0124384B1 (ru) |
| KR (1) | KR910001285B1 (ru) |
| AU (1) | AU562833B2 (ru) |
| BG (3) | BG37996A3 (ru) |
| CA (1) | CA1221366A (ru) |
| DD (1) | DD216021A5 (ru) |
| DE (1) | DE3465199D1 (ru) |
| DK (1) | DK14084A (ru) |
| ES (3) | ES8407059A1 (ru) |
| FI (1) | FI80457C (ru) |
| GR (1) | GR81681B (ru) |
| HU (3) | HU196215B (ru) |
| IE (1) | IE56840B1 (ru) |
| IL (1) | IL70665A (ru) |
| MA (1) | MA20003A1 (ru) |
| NO (1) | NO167205C (ru) |
| NZ (1) | NZ206808A (ru) |
| PL (2) | PL142254B1 (ru) |
| PT (1) | PT77953B (ru) |
| SU (1) | SU1277899A3 (ru) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2557111B1 (fr) * | 1983-12-21 | 1986-04-11 | Rhone Poulenc Sante | Nouveaux derives ortho-condenses du pyrrole, leur preparation et les medicaments qui les contiennent |
| GB8903592D0 (en) * | 1989-02-16 | 1989-04-05 | Boots Co Plc | Therapeutic agents |
| AU5938390A (en) * | 1989-06-26 | 1991-01-17 | Research Foundation Of The State University Of New York, The | Bis-acyloxymethyl derivatives |
| DE4419247A1 (de) * | 1994-06-01 | 1995-12-07 | Merckle Gmbh | Sulfonylierte Pyrrolizincarbonsäureamide und deren Anwendung in der Pharmazie |
| DE4419246A1 (de) * | 1994-06-01 | 1995-12-07 | Merckle Gmbh | Heteroarylsubstituierte Pyrrolizinverbindungen und deren Anwendung in der Pharmazie |
| DE4419315A1 (de) * | 1994-06-01 | 1995-12-07 | Merckle Gmbh | Heteropyrrolizinverbindungen und deren Anwendung in der Pharmazie |
| DE10004157A1 (de) * | 2000-02-01 | 2001-08-02 | Merckle Gmbh Chem Pharm Fabrik | 4-Pyridyl-und 2,4-Pyrimidinyl-substituierte Pyrrolderivate und ihre Anwendung in der Pharmazie |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1401707A (fr) * | 1963-07-03 | 1965-06-04 | Kodak Pathe | Nouveaux colorants, nouveaux composés intermédiaires servant à les préparer et produits photographiques les contenant |
| US3544590A (en) * | 1967-04-28 | 1970-12-01 | Exxon Research Engineering Co | Cyclic amines and the process for their formation |
| US3642807A (en) * | 1970-06-18 | 1972-02-15 | Schering Corp | Certain 1-/dilower-alkyl amino-loweralkyl/-2-phenyl indolizines and quaternary salts thereof |
| US3865839A (en) * | 1973-03-01 | 1975-02-11 | Hoechst Co American | Thiopyranopyrrolylsalicyclic acids and derivatives thereof |
-
1984
- 1984-01-11 AU AU23203/84A patent/AU562833B2/en not_active Ceased
- 1984-01-11 NZ NZ206808A patent/NZ206808A/en unknown
- 1984-01-11 GR GR73493A patent/GR81681B/el unknown
- 1984-01-11 MA MA20224A patent/MA20003A1/fr unknown
- 1984-01-11 DD DD84259350A patent/DD216021A5/de not_active IP Right Cessation
- 1984-01-11 IL IL70665A patent/IL70665A/xx unknown
- 1984-01-11 US US06/569,909 patent/US4539400A/en not_active Expired - Lifetime
- 1984-01-12 DE DE8484400059T patent/DE3465199D1/de not_active Expired
- 1984-01-12 DK DK14084A patent/DK14084A/da unknown
- 1984-01-12 BG BG8465687A patent/BG37996A3/xx not_active Expired
- 1984-01-12 BG BG8463859A patent/BG37839A3/xx unknown
- 1984-01-12 CA CA000445145A patent/CA1221366A/fr not_active Expired
- 1984-01-12 HU HU871615A patent/HU196215B/hu unknown
- 1984-01-12 BG BG8465686A patent/BG37840A3/xx unknown
- 1984-01-12 NO NO840108A patent/NO167205C/no unknown
- 1984-01-12 IE IE65/84A patent/IE56840B1/en not_active IP Right Cessation
- 1984-01-12 HU HU8479A patent/HU193276B/hu not_active IP Right Cessation
- 1984-01-12 PT PT77953A patent/PT77953B/pt not_active IP Right Cessation
- 1984-01-12 FI FI840108A patent/FI80457C/fi not_active IP Right Cessation
- 1984-01-12 HU HU871619A patent/HU196216B/hu unknown
- 1984-01-12 KR KR1019840000096A patent/KR910001285B1/ko not_active IP Right Cessation
- 1984-01-12 EP EP84400059A patent/EP0124384B1/fr not_active Expired
- 1984-01-13 PL PL1984251305A patent/PL142254B1/pl unknown
- 1984-01-13 PL PL1984251306A patent/PL142255B1/pl unknown
- 1984-01-13 ES ES528875A patent/ES8407059A1/es not_active Expired
- 1984-03-28 ES ES531060A patent/ES8501770A1/es not_active Expired
- 1984-03-28 ES ES531061A patent/ES8504822A1/es not_active Expired
- 1984-12-07 SU SU843821206A patent/SU1277899A3/ru active
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| Патент FR № 2412554, кл. С 07 Р513/04, опублик. 1979. * |
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