SU1077570A3 - Способ получени производного гуанидина - Google Patents
Способ получени производного гуанидина Download PDFInfo
- Publication number
- SU1077570A3 SU1077570A3 SU782704652A SU2704652A SU1077570A3 SU 1077570 A3 SU1077570 A3 SU 1077570A3 SU 782704652 A SU782704652 A SU 782704652A SU 2704652 A SU2704652 A SU 2704652A SU 1077570 A3 SU1077570 A3 SU 1077570A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- formula
- methyl
- guanidine
- het
- imidazole
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 title abstract 6
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 title abstract 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 claims description 6
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 claims 1
- 150000002460 imidazoles Chemical class 0.000 claims 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims 1
- -1 2-oxo-3-oxazolidinyl Chemical group 0.000 abstract description 3
- 102000003710 Histamine H2 Receptors Human genes 0.000 abstract description 2
- 108090000050 Histamine H2 Receptors Proteins 0.000 abstract description 2
- 208000007107 Stomach Ulcer Diseases 0.000 abstract description 2
- GCYDEHNKSNMNMN-UHFFFAOYSA-N (5-methyl-1h-imidazol-4-yl)methanethiol Chemical compound CC=1NC=NC=1CS GCYDEHNKSNMNMN-UHFFFAOYSA-N 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 abstract 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 150000002357 guanidines Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- DHTGOTUEWYNOCN-UHFFFAOYSA-N Cl.CSC=1N=CNC=1C Chemical compound Cl.CSC=1N=CNC=1C DHTGOTUEWYNOCN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- LDWZDAMJGLOLGF-UHFFFAOYSA-N 1h-imidazole;hydrochloride Chemical compound Cl.C1=CNC=N1.C1=CNC=N1 LDWZDAMJGLOLGF-UHFFFAOYSA-N 0.000 description 1
- KEWLVUBYGUZFKX-UHFFFAOYSA-N 2-ethylguanidine Chemical compound CCNC(N)=N KEWLVUBYGUZFKX-UHFFFAOYSA-N 0.000 description 1
- PDWPOXKSTFGRIT-UHFFFAOYSA-N 4-(chloromethyl)-5-methyl-1h-imidazole;hydrochloride Chemical compound Cl.CC=1NC=NC=1CCl PDWPOXKSTFGRIT-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- BSTCYTGYWURHKZ-UHFFFAOYSA-N Cl.CC=1N=C(NC1C)S Chemical compound Cl.CC=1N=C(NC1C)S BSTCYTGYWURHKZ-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C07C323/44—X or Y being nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/16—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms
- C07D203/20—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms by carbonic acid, or by sulfur or nitrogen analogues thereof, e.g. carbamates
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНОГО ГУАНИДИНА формулы ИН-СНз СН2-8-СН,-СНг-1«1-сС И 1-СаН СНз .Н . , с использованием производных ймидаэола , отличающийс тем, что, с целью упрощени процесса, хлоргндрат имидазола формулы SH U V СНз НС1 S подвергают взаимодействию с азиридином формулы ,НН-СНз D К-СгК в водной среде в присутствии WaOH в инертной атмосфере. VI Сл
Description
Изобретение относитс к способ получени производного гуанидина формулы . НК-СЯ Н-ц-СНг-З-СНг который обладает лечебными свойст вами, и может быть использовано в медицине при лечении зв желудка, блокиру рецепторы гистамина Н2. Известен способ получени прои хЬодного гуанидина формулы (1) путеи взаимодействи Н -циан-N - f2-| 4-метил-5-имидазолил) -метилмер капто этил -5-метилизотиомочевины с 33%-ным раствором метиламина в этаноле. Реакционную смесь отстаи вают при комнатной температуре в течение 2,5 ч. После упаривани при пониженном давлении остаток дважды перекристаллизовывают из изопропанола/летролейного эфира. Выход 8,6 г или 90% |l. К недостаткс1М данного способа следует отнести труднодоступность исходного реагента и необходимост двойной перекристаллизации целево го продукта дл получени чистого вещества, Цель изобретени - упрощение процесса. Поставленна цель достигаетс тем, что согласно способу получени производного гуанидина формулы (1) с использованием производн . имидазола хлоргидрат имидазола формулы K CK2-SH снзнсг подвергают взаимодействию с азири ном формулы ЦН-СНз 1Г-С«Н в водной среде в присутствии инертной атмосфере. Пример, N -метил-К циано-Я -2-{4-метил-5-имидазолил)-метилтио) -этилгуанидин . К раствору 16,45 г хлоргидрата 4-метил-5-метилмеркаптоимидазола и -12,4 r,N- К-метил-Н -цианокарбоксамидино ) -азиридина в 100 мл дистиллированной воды в потоке азота дог ;бавл ют 4,4 г J4 аОН, поддержива в течение всей реакции инертную атмосферу . После 20 ч при обычной температуре путем фильтровани отдел ют кристаллическую фазу продукта, котора рекристаллизуетс в ацетонитриле , т.пл. 142-143®С. Выход 90%. Исходные продукты приготавливают следукицим образом. 1.Хлоргидрат 4-метил-5-метилмеркаптоимидазол . В течение б ч через раствор 8,7 г 4-метил-5-(этоксидитиоформил) -имидазола в 100 мл 12 и. сол ной кислоты пропускают противоток азота, растворитель удал ют -при пониженном давлении , и твердый осадок кристаллизуют на холоде в бутаноле-2, рекристаллизуют в бутаноле-2, т.пл. 208-210 С. Выход 90%. 2.Хлоргидрат 4-метил-5-метилмеркаптоимидазола . К раствору 16,5 г хлоргидрата 4-метил-5-хлорметилимидазола в 70 мл этилового спирта добавл ют 29,6 г этилксантата кали и поддерживают поток в течение 3 ч. Остатки после испарени помещают в 100 мл 12 н. СОЛЯНОЙ кислоты в потоке азота в течение 6 ч. Растворитель удал ют при пониженном давлении и твердый остаток кристаллизуют на холоде в бутаноле-2, рекристаллизуют в бутаноле-2 , т.пл. 208-210 С. Выход 80%. Таким образом, предлагаемый способ позвол ет получить целевой продукт из доступных исходных продуктов , например азиридина - многотоннажного продукта, который широко используетс в бумажной промышленности . Кроме того, реакционноспособность азиридииа настолько высока,, а реакци протекает в настолько м гких услови х, что побочные продукты не образуютс и целевой продукт не требует перекристаллизации.
Claims (2)
- СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОД1НОГО ГУАНИДИНА формулы„ΝΗ-СНзСН2" 5 -ен.,- СНГБН- сС аСНзIнс использованием производных имидазола, отличающийся тем, что, с целью упрощения процесса, хлоргидрат имидазола формулыОС| СНз-НС!подвергают взаимодействию с азйридином формулын.сГ-™-сн,в водной среде в присутствии МаОН в инертной атмосфере.107757011077570
- 2
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1612677A CH626353A5 (en) | 1977-12-28 | 1977-12-28 | Process for the preparation of a guanidine |
| CH1247778A CH636348A5 (en) | 1978-12-07 | 1978-12-07 | Process for the preparation of guanidine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1077570A3 true SU1077570A3 (ru) | 1984-02-29 |
Family
ID=25710349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782704652A SU1077570A3 (ru) | 1977-12-28 | 1978-12-28 | Способ получени производного гуанидина |
Country Status (12)
| Country | Link |
|---|---|
| JP (2) | JPS5827792B2 (ru) |
| CS (1) | CS208770B2 (ru) |
| DE (1) | DE2855836A1 (ru) |
| ES (1) | ES476707A1 (ru) |
| FI (1) | FI74954C (ru) |
| IL (1) | IL56265A (ru) |
| IT (1) | IT1102776B (ru) |
| NL (1) | NL184832C (ru) |
| PL (1) | PL115042B1 (ru) |
| RO (1) | RO76087A (ru) |
| SU (1) | SU1077570A3 (ru) |
| YU (1) | YU41138B (ru) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL56265A (en) * | 1977-12-28 | 1982-08-31 | Om Lab Sa | Process for preparing imidazolyl methylthio guanidine derivatives and a novel intermediate therefor |
| NO784350L (no) * | 1977-12-30 | 1979-07-03 | Crc Ricerca Chim | Fremgangsmaate til alkylering av 4(5)-merkaptometyl-imidazoler med aziridinderivater |
| YU40332B (en) * | 1978-04-26 | 1985-12-31 | Lek Tovarna Farmacevtskih | Process for preparing n-cyano-n'-methyl-n''-((2-((4-methyl-5-imidazolyl)-methylthio)ethyl)-guanidine |
| LU81178A1 (de) * | 1978-05-12 | 1979-09-10 | Crc Ricerca Chim | Neue thiolderivate des imidazols |
| US4222845A (en) * | 1978-12-13 | 1980-09-16 | Gulf Oil Corporation | Integrated coal liquefaction-gasification-naphtha reforming process |
| JPS56500174A (ru) * | 1979-02-14 | 1981-02-19 | ||
| CH642068A5 (fr) * | 1979-03-14 | 1984-03-30 | Rech Syntheses Organ | Cyano-urees et cyano-thiourees therapeutiquement actives. |
| PT72320B (en) | 1980-01-08 | 1982-07-23 | Glaxo Group Ltd | Process for preparation of a furan derivative |
| YU41689B (en) * | 1980-01-14 | 1987-12-31 | Lek Tovarna Farmacevtskih | Process for preparing imidazole derivatives |
| DE3014353A1 (de) * | 1980-04-15 | 1982-01-21 | Bayer Ag, 5090 Leverkusen | Trisubstituierte cyanguanidine, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| JPS5888366A (ja) * | 1981-11-19 | 1983-05-26 | Fujimoto Seiyaku Kk | グアニジン誘導体の製造法 |
| JPS59130273A (ja) * | 1983-01-14 | 1984-07-26 | Tokawa Tetsuo | イミダゾ−ル系化合物の製造法 |
| JPS6170789U (ru) * | 1984-10-16 | 1986-05-14 | ||
| GB8502446D0 (en) * | 1985-01-31 | 1985-03-06 | Smith Kline French Lab | Preparing aziridine derivative |
| YU45030B (en) * | 1987-01-23 | 1991-06-30 | Lek Tovarna Farmacevtskih | Process for preparing crystalline cimetidine |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE36050B1 (en) * | 1971-03-09 | 1976-08-04 | Smith Kline French Lab | Ureas thioureas and guanidines |
| GB1533380A (en) * | 1974-09-02 | 1978-11-22 | Smith Kline French Lab | Process for the preparation of heterocyclic substituted thioureas and h-cyanoguanidines |
| GB1531231A (en) * | 1974-09-02 | 1978-11-08 | Smith Kline French Lab | Process for the production of cyanoguanidine derivatives |
| JPS5817511B2 (ja) * | 1975-10-03 | 1983-04-07 | 積水化学工業株式会社 | セツチヤクザイソセイブツ |
| MW5076A1 (en) * | 1975-12-29 | 1978-02-08 | Smith Kline French Lab | Pharmacologicalle active compounds |
| JPS5440547A (en) * | 1977-09-07 | 1979-03-30 | Seikosha Kk | Device for adjusting output frequency of frequency divider |
| IL56265A (en) * | 1977-12-28 | 1982-08-31 | Om Lab Sa | Process for preparing imidazolyl methylthio guanidine derivatives and a novel intermediate therefor |
| JPS5742068A (en) * | 1980-08-27 | 1982-03-09 | Ricoh Co Ltd | Solvent recovering device for wet type electronic copying machine |
| JPS6011994B2 (ja) * | 1981-08-10 | 1985-03-29 | 池田 博美 | ガソリンエンジン用液体燃料 |
| JPS5888366A (ja) * | 1981-11-19 | 1983-05-26 | Fujimoto Seiyaku Kk | グアニジン誘導体の製造法 |
-
1978
- 1978-12-20 IL IL7856265A patent/IL56265A/xx unknown
- 1978-12-22 DE DE19782855836 patent/DE2855836A1/de active Granted
- 1978-12-22 ES ES476707A patent/ES476707A1/es not_active Expired
- 1978-12-27 FI FI783990A patent/FI74954C/fi not_active IP Right Cessation
- 1978-12-27 CS CS788968A patent/CS208770B2/cs unknown
- 1978-12-27 YU YU3084/78A patent/YU41138B/xx unknown
- 1978-12-28 JP JP53164401A patent/JPS5827792B2/ja not_active Expired
- 1978-12-28 IT IT7831392A patent/IT1102776B/it active
- 1978-12-28 RO RO7896094A patent/RO76087A/ro unknown
- 1978-12-28 SU SU782704652A patent/SU1077570A3/ru active
- 1978-12-28 PL PL1978212223A patent/PL115042B1/pl unknown
- 1978-12-28 NL NLAANVRAGE7812600,A patent/NL184832C/xx not_active IP Right Cessation
-
1983
- 1983-07-14 JP JP58129273A patent/JPS5962572A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| 1. Выложенна за вка DE 2344779, кл. 12 р 9, опублик. 1974. . -: . ; i S:- I * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54130566A (en) | 1979-10-09 |
| DE2855836A1 (de) | 1979-07-12 |
| RO76087A (ro) | 1981-02-28 |
| JPS5827792B2 (ja) | 1983-06-11 |
| NL184832C (nl) | 1989-11-16 |
| PL115042B1 (en) | 1981-03-31 |
| NL7812600A (nl) | 1979-07-02 |
| ES476707A1 (es) | 1979-06-01 |
| IT1102776B (it) | 1985-10-07 |
| IL56265A (en) | 1982-08-31 |
| FI783990A (fi) | 1979-06-29 |
| JPS5962572A (ja) | 1984-04-10 |
| FI74954C (fi) | 1988-04-11 |
| FI74954B (fi) | 1987-12-31 |
| IL56265A0 (en) | 1979-03-12 |
| IT7831392A0 (it) | 1978-12-28 |
| PL212223A1 (pl) | 1979-08-27 |
| YU41138B (en) | 1986-12-31 |
| DE2855836C2 (ru) | 1989-09-28 |
| CS208770B2 (en) | 1981-09-15 |
| YU308478A (en) | 1983-01-21 |
| JPS6140667B2 (ru) | 1986-09-10 |
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