HU185298B - Process for producing cimetidine - Google Patents
Process for producing cimetidine Download PDFInfo
- Publication number
- HU185298B HU185298B HU187681A HU187681A HU185298B HU 185298 B HU185298 B HU 185298B HU 187681 A HU187681 A HU 187681A HU 187681 A HU187681 A HU 187681A HU 185298 B HU185298 B HU 185298B
- Authority
- HU
- Hungary
- Prior art keywords
- methylamine
- reaction
- cimetidine
- methyl
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 229960001380 cimetidine Drugs 0.000 title claims description 14
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 title description 13
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000011541 reaction mixture Substances 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 239000012736 aqueous medium Substances 0.000 claims abstract description 6
- 238000010533 azeotropic distillation Methods 0.000 claims abstract description 3
- 150000004682 monohydrates Chemical class 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 19
- AQIXAKUUQRKLND-UHFFFAOYSA-N cimetidine Chemical compound N#C/N=C(/NC)NCCSCC=1N=CNC=1C AQIXAKUUQRKLND-UHFFFAOYSA-N 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 abstract description 9
- -1 5-methylimidazol-4-yl Chemical group 0.000 abstract description 3
- 238000009835 boiling Methods 0.000 abstract description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 abstract 2
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 abstract 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000012535 impurity Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- AUUYARZXATYXHN-UHFFFAOYSA-N Cl.C(#N)NC(SC)=NCCSCC=1N=CNC1C Chemical compound Cl.C(#N)NC(SC)=NCCSCC=1N=CNC1C AUUYARZXATYXHN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- PQTDYPBOJLSPKE-UHFFFAOYSA-N methyl n-cyano-n'-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]carbamimidothioate;hydrate Chemical compound O.N#CNC(SC)=NCCSCC=1N=CNC=1C PQTDYPBOJLSPKE-UHFFFAOYSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- UBHDUFNPQJWPRQ-UHFFFAOYSA-N (5-methyl-1h-imidazol-3-ium-4-yl)methanol;chloride Chemical compound Cl.CC=1NC=NC=1CO UBHDUFNPQJWPRQ-UHFFFAOYSA-N 0.000 description 1
- JEOZNMMOIBLWLV-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethanamine Chemical compound CC=1N=CNC=1CSCCN JEOZNMMOIBLWLV-UHFFFAOYSA-N 0.000 description 1
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FPBPLBWLMYGIQR-UHFFFAOYSA-N Metiamide Chemical compound CNC(=S)NCCSCC=1N=CNC=1C FPBPLBWLMYGIQR-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- XMYLSWOTJKUSHE-UHFFFAOYSA-N cyanamide;lead Chemical compound [Pb].NC#N XMYLSWOTJKUSHE-UHFFFAOYSA-N 0.000 description 1
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 238000000326 densiometry Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- WSUNDBVVUCLXTG-UHFFFAOYSA-N methyl n-cyano-n'-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]carbamimidothioate Chemical compound N#CNC(SC)=NCCSCC=1NC=NC=1C WSUNDBVVUCLXTG-UHFFFAOYSA-N 0.000 description 1
- MHGGQXIPBPGZFB-UHFFFAOYSA-N methyl n-cyano-n'-methylcarbamimidothioate Chemical compound CSC(=NC)NC#N MHGGQXIPBPGZFB-UHFFFAOYSA-N 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT80481A AT377562B (de) | 1981-02-23 | 1981-02-23 | Stranggepresster hohlziegel |
| HU187681A HU185298B (en) | 1981-06-26 | 1981-06-26 | Process for producing cimetidine |
| BE1/10541A BE893608A (fr) | 1981-06-26 | 1982-06-23 | Procede pour la preparation de la cimetidine |
| GB08218311A GB2103206B (en) | 1981-06-26 | 1982-06-24 | Process for preparing an imidazole derivative |
| AT245182A AT378186B (de) | 1981-06-26 | 1982-06-24 | Verfahren zur herstellung von cimetidin |
| DE19823223802 DE3223802A1 (de) | 1981-06-26 | 1982-06-25 | Verfahren zur herstellung von 1-cyan-2-methyl-3-<2'-(((5''-methylimidazol- 4''-yl)-methyl)-thio)-aethyl>-guanidin (cimetidin) |
| FR8211152A FR2508447B1 (fr) | 1981-06-26 | 1982-06-25 | Procede pour la preparation de la cimetidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU187681A HU185298B (en) | 1981-06-26 | 1981-06-26 | Process for producing cimetidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU185298B true HU185298B (en) | 1984-12-28 |
Family
ID=10956621
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU187681A HU185298B (en) | 1981-02-23 | 1981-06-26 | Process for producing cimetidine |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT378186B (enrdf_load_stackoverflow) |
| BE (1) | BE893608A (enrdf_load_stackoverflow) |
| DE (1) | DE3223802A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2508447B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2103206B (enrdf_load_stackoverflow) |
| HU (1) | HU185298B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0224612A1 (de) * | 1985-12-05 | 1987-06-10 | HEUMANN PHARMA GMBH & CO | Verfahren zur Herstellung von N-Cyano-N'-methyl-N"[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]guanidin |
| CN114149348A (zh) * | 2021-12-15 | 2022-03-08 | 河北新石制药有限公司 | 西咪替丁缩合杂质的合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE804144A (en) * | 1972-09-05 | 1974-02-28 | Smith Kline French Lab | H-2-Receptor antihistamines esp gastric acid inhibitors - -N-cyano-N"-(heterocyclyl-alkyl-(thio oxa amino or methylene-alkyl)-guanidines |
| YU40716B (en) * | 1978-07-19 | 1986-04-30 | Pliva Pharm & Chem Works | Process for obtaining n-cyano-n'-methyl-n'-û2-|5-metylimidazole4-yl)-methyl¨-thioethylù guanidine |
| JPS5610175A (en) * | 1979-07-06 | 1981-02-02 | Fujisawa Pharmaceut Co Ltd | Preparation of imidazole derivative |
-
1981
- 1981-06-26 HU HU187681A patent/HU185298B/hu not_active IP Right Cessation
-
1982
- 1982-06-23 BE BE1/10541A patent/BE893608A/fr not_active IP Right Cessation
- 1982-06-24 AT AT245182A patent/AT378186B/de not_active IP Right Cessation
- 1982-06-24 GB GB08218311A patent/GB2103206B/en not_active Expired
- 1982-06-25 FR FR8211152A patent/FR2508447B1/fr not_active Expired
- 1982-06-25 DE DE19823223802 patent/DE3223802A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3223802A1 (de) | 1983-01-13 |
| ATA245182A (de) | 1984-11-15 |
| GB2103206A (en) | 1983-02-16 |
| BE893608A (fr) | 1982-12-23 |
| FR2508447B1 (fr) | 1986-05-16 |
| AT378186B (de) | 1985-06-25 |
| GB2103206B (en) | 1985-02-13 |
| FR2508447A1 (fr) | 1982-12-31 |
| DE3223802C2 (enrdf_load_stackoverflow) | 1992-01-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0339061B2 (enrdf_load_stackoverflow) | ||
| SU677655A3 (ru) | Способ получени -циклоалкилметил-2-фениламиноимидазолинов-2или их солей | |
| JPH09255651A (ja) | Ｎ−メチル−ｎ′−ニトログアニジンの製造法 | |
| KR920002295B1 (ko) | 프롤리디논 유도체의 제조방법 | |
| US6673922B2 (en) | Process for preparing triazine compound and quaternary ammonium salts | |
| HU185298B (en) | Process for producing cimetidine | |
| HU185457B (en) | Process for preparating cimetidine-z | |
| DK169920B1 (da) | Fremgangsmåde til fremstilling af N-sulfamyl-3-(2-guanidinothiazol-4-ylmethylthio)propionamidin | |
| SU1122222A3 (ru) | Способ получени циметидина | |
| JPH0256354B2 (enrdf_load_stackoverflow) | ||
| US4275216A (en) | Process for preparing 4(5)-hydroxymethyl 5(4)-lower alkyl imidazoles | |
| EP0066440B1 (en) | Chemical process | |
| US6248888B1 (en) | Process for the preparation of terazosin hydrochloride dihydrate | |
| JPS6317837B2 (enrdf_load_stackoverflow) | ||
| JPH062747B2 (ja) | ２‐アルキル‐４，５‐ジヒドロキシメチルイミダゾールの製法 | |
| JP3082006B2 (ja) | ２−アルキルチオ−４，６−ジヒドロキシピリミジンの製造法 | |
| KR20200088570A (ko) | 피마살탄 및 그의 제조 중간체의 제조방법 | |
| HU225245B1 (en) | Process for producing heterocyclic compounds | |
| JPH0113469B2 (enrdf_load_stackoverflow) | ||
| JP2002155058A (ja) | １位置換ヒダントイン類の製造方法 | |
| JPH0469156B2 (enrdf_load_stackoverflow) | ||
| SU791232A3 (ru) | Способ получени производных 2- ариламино-2-имидазолина | |
| HU185636B (en) | Process for preparing new cimetidine-hydrate /cimetidine-h/ | |
| KR790001309B1 (ko) | 우라실 유도체의 제조법 | |
| KR810000271B1 (ko) | 1-(2'-퓨라니딜)-5-플루오로 우라실의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |