SU950188A3 - Способ получени производных 4(5)-меркаптометилимидазолов - Google Patents
Способ получени производных 4(5)-меркаптометилимидазолов Download PDFInfo
- Publication number
- SU950188A3 SU950188A3 SU792802997A SU2802997A SU950188A3 SU 950188 A3 SU950188 A3 SU 950188A3 SU 792802997 A SU792802997 A SU 792802997A SU 2802997 A SU2802997 A SU 2802997A SU 950188 A3 SU950188 A3 SU 950188A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- carried out
- fact
- formula
- methyl
- methanol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 5
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 7
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 208000007107 Stomach Ulcer Diseases 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 208000000718 duodenal ulcer Diseases 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 1
- KEWLVUBYGUZFKX-UHFFFAOYSA-N 2-ethylguanidine Chemical compound CCNC(N)=N KEWLVUBYGUZFKX-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 101100001674 Emericella variicolor andI gene Proteins 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- FPWNQPQTICPCOM-UHFFFAOYSA-N acetonitrile;propan-2-ol Chemical compound CC#N.CC(C)O FPWNQPQTICPCOM-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000010438 heat treatment 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
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1634077A CH631971A5 (en) | 1977-12-30 | 1977-12-30 | Process for preparing imidazole derivatives |
| CH1069578 | 1978-10-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU950188A3 true SU950188A3 (ru) | 1982-08-07 |
Family
ID=25707086
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU792802997A SU950188A3 (ru) | 1977-12-30 | 1979-08-21 | Способ получени производных 4(5)-меркаптометилимидазолов |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS55500026A (cs) |
| CS (1) | CS207750B2 (cs) |
| DE (1) | DE2857324D2 (cs) |
| DK (1) | DK319679A (cs) |
| FI (1) | FI784018A7 (cs) |
| FR (1) | FR2413373A1 (cs) |
| GB (1) | GB2036003B (cs) |
| GR (1) | GR65283B (cs) |
| IT (1) | IT1102765B (cs) |
| NL (1) | NL171054C (cs) |
| NO (1) | NO784350L (cs) |
| PL (1) | PL113033B1 (cs) |
| SE (1) | SE7907148L (cs) |
| SU (1) | SU950188A3 (cs) |
| WO (1) | WO1979000466A1 (cs) |
| YU (1) | YU313178A (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS213376B2 (en) * | 1978-05-12 | 1982-04-09 | Crc Ricerca Chim | Method of making the derivatives of n-kyanoazomethines |
| LU81178A1 (de) * | 1978-05-12 | 1979-09-10 | Crc Ricerca Chim | Neue thiolderivate des imidazols |
| WO1981000255A1 (en) * | 1979-07-16 | 1981-02-05 | Rech Syntheses Organ | Imino-alkyl and amino-nitril cyano-guanidines |
| JPS56501008A (cs) * | 1979-07-30 | 1981-07-23 | ||
| PT72320B (en) * | 1980-01-08 | 1982-07-23 | Glaxo Group Ltd | Process for preparation of a furan derivative |
| CA1181084A (en) * | 1980-01-08 | 1985-01-15 | Glaxo Group Limited | Process for the preparation of a furan derivative |
| EP0058286A1 (fr) * | 1981-02-12 | 1982-08-25 | Société de Recherches et de Synthèses Organiques SA | Isomères géométriques de cyano-guanidines et leurs procédés de préparation |
| GB8502446D0 (en) * | 1985-01-31 | 1985-03-06 | Smith Kline French Lab | Preparing aziridine derivative |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1531231A (en) * | 1974-09-02 | 1978-11-08 | Smith Kline French Lab | Process for the production of cyanoguanidine derivatives |
| GB1533380A (en) * | 1974-09-02 | 1978-11-22 | Smith Kline French Lab | Process for the preparation of heterocyclic substituted thioureas and h-cyanoguanidines |
| IL56265A (en) * | 1977-12-28 | 1982-08-31 | Om Lab Sa | Process for preparing imidazolyl methylthio guanidine derivatives and a novel intermediate therefor |
-
1978
- 1978-12-22 GR GR57973A patent/GR65283B/el unknown
- 1978-12-22 NO NO784350A patent/NO784350L/no unknown
- 1978-12-28 FI FI784018A patent/FI784018A7/fi unknown
- 1978-12-28 WO PCT/CH1978/000058 patent/WO1979000466A1/de unknown
- 1978-12-28 DE DE78CH7800058T patent/DE2857324D2/de not_active Expired
- 1978-12-28 IT IT31352/78A patent/IT1102765B/it active
- 1978-12-28 JP JP50020578A patent/JPS55500026A/ja active Pending
- 1978-12-28 GB GB7928551A patent/GB2036003B/en not_active Expired
- 1978-12-29 FR FR7836922A patent/FR2413373A1/fr active Pending
- 1978-12-29 CS CS789198A patent/CS207750B2/cs unknown
- 1978-12-29 YU YU03131/78A patent/YU313178A/xx unknown
- 1978-12-29 NL NLAANVRAGE7812662,A patent/NL171054C/xx not_active IP Right Cessation
- 1978-12-30 PL PL1978212389A patent/PL113033B1/pl unknown
-
1979
- 1979-07-30 DK DK319679A patent/DK319679A/da not_active Application Discontinuation
- 1979-08-21 SU SU792802997A patent/SU950188A3/ru active
- 1979-08-28 SE SE7907148A patent/SE7907148L/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IT1102765B (it) | 1985-10-07 |
| YU313178A (en) | 1982-10-31 |
| PL113033B1 (en) | 1980-11-29 |
| NL7812662A (nl) | 1979-07-03 |
| NL171054B (nl) | 1982-09-01 |
| NO784350L (no) | 1979-07-03 |
| WO1979000466A1 (en) | 1979-07-26 |
| IT7831352A0 (it) | 1978-12-28 |
| GB2036003A (en) | 1980-06-25 |
| CS207750B2 (en) | 1981-08-31 |
| PL212389A1 (pl) | 1979-08-13 |
| JPS55500026A (cs) | 1980-01-24 |
| NL171054C (nl) | 1983-02-01 |
| SE7907148L (sv) | 1979-08-28 |
| GB2036003B (en) | 1982-08-18 |
| FI784018A7 (fi) | 1979-07-01 |
| FR2413373A1 (fr) | 1979-07-27 |
| DE2857324D2 (en) | 1980-11-20 |
| DK319679A (da) | 1979-08-30 |
| GR65283B (en) | 1980-08-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4794185A (en) | Process for the preparation of imidazopyridines | |
| SU888815A3 (ru) | Способ получени нитросоединений | |
| SU950188A3 (ru) | Способ получени производных 4(5)-меркаптометилимидазолов | |
| RU1802811C (ru) | Способ получени N-( @ -замещенный алкил)-N @ -(имидазол-4-ил)-гуанидина или его кислых аддитивных солей | |
| IE48532B1 (en) | Process for preparing h2-receptor antagonist cimetidine | |
| KR910005850B1 (ko) | 이미다조[1,5-a]피리미딘 유도체의 제조방법 | |
| HU195486B (en) | Process for preparing new pyridine derivatives | |
| KR840002007B1 (ko) | 푸란유도체의 제조방법 | |
| US4394516A (en) | Process for the preparation of a furan derivative | |
| EP1927590B1 (en) | Method for producing 1-substituted-5-acylimidazole compound | |
| SU936811A3 (ru) | Способ получени пиридазинилгидразонов или их кислотно-аддитивных солей | |
| SU1227111A3 (ru) | Способ получени производных гуанидина или их таутомерных соединений или их солей | |
| US3320272A (en) | Process for preparing z-alkoxycyclo- heptimidazole derivatives | |
| US3461131A (en) | Process for preparing 2-substituted cycloheptimidazole derivatives | |
| Shimadzu et al. | Studies on furan derivatives. XIV. Nucleophilic substitution of methyl 5‐nitro‐2‐furancarboxylate and 5‐Nitrofuran‐2‐nitrile | |
| SU900802A3 (ru) | Способ получени этиленимино-циано-азометинов | |
| US4200761A (en) | Process for preparing N-cyano-N'methyl-N"-{2-[(4-methyl-5-imidazolyl)-methylthio]-ethyl} guanidine | |
| US3226379A (en) | Novel 1,3-bis(polyhydroxyalkyl)-2-imidazolidinones and 1,3-bis(polyhydroxyalkyl)-imidazolidine-2-thiones | |
| CN119462612A (zh) | 制备二氨基嘧啶衍生物或其酸加成盐的新方法 | |
| KR920004137B1 (ko) | 이미다졸 유도체의 제조방법 | |
| EP0034421B1 (en) | N-phenyl-n'-cyano-0-phenylisoureas and process for their preparation | |
| SU655307A3 (ru) | Способ получени производных гуанидинов или их солей | |
| NO863769L (no) | Fremgangsmaate for fremstilling av 4-hydroksy-2-oksopyrrolin-1-yl-acetamid. | |
| US4189444A (en) | Process for the preparation of N,N'-disubstituted 2-naphthaleneethanimidamide and intermediates used therein | |
| EP0276574B1 (en) | Alpha-acyloxyketone derivatives |