HU188074B - Process for the preparation of cimetidin - Google Patents
Process for the preparation of cimetidin Download PDFInfo
- Publication number
- HU188074B HU188074B HU812400A HU240081A HU188074B HU 188074 B HU188074 B HU 188074B HU 812400 A HU812400 A HU 812400A HU 240081 A HU240081 A HU 240081A HU 188074 B HU188074 B HU 188074B
- Authority
- HU
- Hungary
- Prior art keywords
- methyl
- cimetidine
- guanidine
- cyano
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 229960001380 cimetidine Drugs 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000011541 reaction mixture Substances 0.000 claims abstract description 4
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 claims abstract 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- WICBLRRSUUGZGC-UHFFFAOYSA-N 1-cyano-2-methyl-1-(2-sulfanylethyl)guanidine Chemical compound CNC(=N)N(C#N)CCS WICBLRRSUUGZGC-UHFFFAOYSA-N 0.000 claims description 7
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
- PDWPOXKSTFGRIT-UHFFFAOYSA-N 4-(chloromethyl)-5-methyl-1h-imidazole;hydrochloride Chemical compound Cl.CC=1NC=NC=1CCl PDWPOXKSTFGRIT-UHFFFAOYSA-N 0.000 claims description 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 4
- -1 5-methyl-1H-imidazol-4-yl Chemical group 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- BCNSGSPCHOJOHW-UHFFFAOYSA-N 1-methyl-1-(2-sulfanylethyl)guanidine Chemical compound NC(=N)N(C)CCS BCNSGSPCHOJOHW-UHFFFAOYSA-N 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 abstract description 4
- ZORWZOOZJGMSTE-UHFFFAOYSA-N 1-cyano-2-methyl-3-(2-sulfanylethyl)guanidine Chemical compound N#CNC(=NC)NCCS ZORWZOOZJGMSTE-UHFFFAOYSA-N 0.000 abstract description 3
- 208000007107 Stomach Ulcer Diseases 0.000 abstract description 2
- 201000005917 gastric ulcer Diseases 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract 1
- AQIXAKUUQRKLND-UHFFFAOYSA-N cimetidine Chemical compound N#C/N=C(/NC)NCCSCC=1N=CNC=1C AQIXAKUUQRKLND-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- IWXZVNKDTSUCSF-UHFFFAOYSA-N 4-(bromomethyl)-5-methyl-1h-imidazole;hydrobromide Chemical compound Br.CC=1NC=NC=1CBr IWXZVNKDTSUCSF-UHFFFAOYSA-N 0.000 description 4
- APZXPRHPPCTRHN-UHFFFAOYSA-N 4-(chloromethyl)-5-methyl-1h-imidazole Chemical compound CC=1NC=NC=1CCl APZXPRHPPCTRHN-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- PUIDZZJQDCILKY-UHFFFAOYSA-N 1-cyano-2-methyl-1-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound CN=C(N)N(C#N)CCSCC=1N=CNC=1C PUIDZZJQDCILKY-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- MHGGQXIPBPGZFB-UHFFFAOYSA-N methyl n-cyano-n'-methylcarbamimidothioate Chemical compound CSC(=NC)NC#N MHGGQXIPBPGZFB-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- AXJZCJSXNZZMDU-UHFFFAOYSA-N (5-methyl-1h-imidazol-4-yl)methanol Chemical compound CC=1N=CNC=1CO AXJZCJSXNZZMDU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 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
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- DNTJOBABUVWGNS-UHFFFAOYSA-N 4-(bromomethyl)-5-methyl-1h-imidazole Chemical compound CC=1NC=NC=1CBr DNTJOBABUVWGNS-UHFFFAOYSA-N 0.000 description 1
- FASMXPUFMXBVRL-UHFFFAOYSA-N 5-(chloromethyl)-1h-imidazole;hydron;chloride Chemical compound Cl.ClCC1=CN=CN1 FASMXPUFMXBVRL-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 230000027125 histamine-induced gastric acid secretion Effects 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000003389 potentiating 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
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 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 1
- 231100000925 very toxic Toxicity 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
-
- 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
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)
- Cephalosporin Compounds (AREA)
- Lubricants (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Compounds Of Unknown Constitution (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI802649A FI63753C (fi) | 1980-08-21 | 1980-08-21 | Foerfarande foer framstaellning av kristallint simetidin. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU188074B true HU188074B (en) | 1986-03-28 |
Family
ID=8513706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU812400A HU188074B (en) | 1980-08-21 | 1981-08-17 | Process for the preparation of cimetidin |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0046635B1 (en, 2012) |
| JP (1) | JPH0153272B2 (en, 2012) |
| AT (1) | ATE14123T1 (en, 2012) |
| BG (1) | BG36786A3 (en, 2012) |
| CA (1) | CA1164876A (en, 2012) |
| CS (1) | CS220346B2 (en, 2012) |
| DD (1) | DD201675A5 (en, 2012) |
| DE (1) | DE3171202D1 (en, 2012) |
| DK (1) | DK554580A (en, 2012) |
| ES (1) | ES8204425A1 (en, 2012) |
| FI (1) | FI63753C (en, 2012) |
| GR (1) | GR67669B (en, 2012) |
| HU (1) | HU188074B (en, 2012) |
| NO (1) | NO155440C (en, 2012) |
| PL (1) | PL133507B1 (en, 2012) |
| PT (1) | PT73478B (en, 2012) |
| RO (1) | RO83439B (en, 2012) |
| SU (1) | SU1122222A3 (en, 2012) |
| YU (1) | YU201481A (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59130274A (ja) * | 1983-01-14 | 1984-07-26 | Tokawa Tetsuo | イミダゾ−ル系化合物の製法 |
| JPS6182818A (ja) * | 1984-10-01 | 1986-04-26 | Toray Ind Inc | 化学薬品の精製法 |
| GB8618846D0 (en) * | 1986-08-01 | 1986-09-10 | Smithkline Beckman Corp | Chemical process |
| JPH0627120B2 (ja) * | 1986-11-07 | 1994-04-13 | 三井石油化学工業株式会社 | 新規なα−クロロケトン誘導体および製造法 |
| JPH064601B2 (ja) * | 1987-11-04 | 1994-01-19 | 三井石油化学工業株式会社 | Ｎ−シアノ−ｎ’−メチル−ｎ’’−［２−｛（５−メチル−１ｈ−イミダゾール−４−イル）メチルチオ｝エチルグアニジンの精製法 |
| 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 (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4093621A (en) * | 1974-09-02 | 1978-06-06 | Smith Kline & French Laboratories Limited | Process for preparing heterocyclicalkylthioalkyl-N-cyanoguanidines and thioureas |
| US4215217A (en) * | 1975-10-29 | 1980-07-29 | Sk&F Lab Co. | Process for preparing 4-substituted imidazole compounds |
| ES458042A1 (es) * | 1977-04-06 | 1978-08-16 | Ricorvi S A | Nuevo procedimiento para la sintesis de la 1-ciano-2-metil- 3-(2-(((5-metil-imidazol-4-il-)metil)tio)etil)-guanidina. |
| US4112234A (en) * | 1977-08-22 | 1978-09-05 | Bristol-Myers Company | Imidazolylmethylthioethyl alkynyl guanidines |
-
1980
- 1980-08-21 FI FI802649A patent/FI63753C/fi not_active IP Right Cessation
- 1980-12-29 DK DK554580A patent/DK554580A/da not_active Application Discontinuation
-
1981
- 1981-07-23 DE DE8181303378T patent/DE3171202D1/de not_active Expired
- 1981-07-23 EP EP81303378A patent/EP0046635B1/en not_active Expired
- 1981-07-23 AT AT81303378T patent/ATE14123T1/de not_active IP Right Cessation
- 1981-07-27 GR GR65640A patent/GR67669B/el unknown
- 1981-08-03 JP JP56120798A patent/JPH0153272B2/ja not_active Expired
- 1981-08-04 PT PT73478A patent/PT73478B/pt unknown
- 1981-08-05 CA CA000383256A patent/CA1164876A/en not_active Expired
- 1981-08-11 ES ES504698A patent/ES8204425A1/es not_active Expired
- 1981-08-17 HU HU812400A patent/HU188074B/hu unknown
- 1981-08-18 SU SU813322501A patent/SU1122222A3/ru active
- 1981-08-19 CS CS816219A patent/CS220346B2/cs unknown
- 1981-08-19 DD DD81232689A patent/DD201675A5/de unknown
- 1981-08-20 YU YU02014/81A patent/YU201481A/xx unknown
- 1981-08-20 RO RO105135A patent/RO83439B/ro unknown
- 1981-08-20 NO NO812813A patent/NO155440C/no unknown
- 1981-08-21 BG BG053354A patent/BG36786A3/xx unknown
- 1981-09-20 PL PL1981232730A patent/PL133507B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU1122222A3 (ru) | 1984-10-30 |
| NO155440C (no) | 1987-04-01 |
| EP0046635A1 (en) | 1982-03-03 |
| JPH0153272B2 (en, 2012) | 1989-11-13 |
| ES504698A0 (es) | 1982-05-16 |
| CA1164876A (en) | 1984-04-03 |
| RO83439A (ro) | 1984-02-21 |
| EP0046635B1 (en) | 1985-07-03 |
| NO155440B (no) | 1986-12-22 |
| DD201675A5 (de) | 1983-08-03 |
| FI63753B (fi) | 1983-04-29 |
| FI802649A7 (fi) | 1982-02-22 |
| JPS5754176A (en, 2012) | 1982-03-31 |
| PT73478B (en) | 1983-11-30 |
| YU201481A (en) | 1984-02-29 |
| GR67669B (en, 2012) | 1981-09-02 |
| BG36786A3 (bg) | 1985-01-15 |
| DE3171202D1 (en) | 1985-08-08 |
| PL133507B1 (en) | 1985-06-29 |
| DK554580A (da) | 1982-02-22 |
| PL232730A1 (en, 2012) | 1982-04-26 |
| ES8204425A1 (es) | 1982-05-16 |
| PT73478A (en) | 1981-09-01 |
| ATE14123T1 (de) | 1985-07-15 |
| NO812813L (no) | 1982-02-22 |
| FI63753C (fi) | 1987-02-19 |
| CS220346B2 (en) | 1983-03-25 |
| RO83439B (ro) | 1984-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1296716C (en) | N-(2-substituted alkyl)-n'-[(imidazole-4-yl) alkyl] guanidine | |
| DE1118789B (de) | Verfahren zur Herstellung von 1, 3, 5-Triazinderivaten | |
| HU188074B (en) | Process for the preparation of cimetidin | |
| EP0285681B1 (de) | Verfahren zur Herstellung von Nitroethenderivaten | |
| EP0179408B1 (de) | Neue Amidoalkylmelamine und Aminoalkylmelamine und Verfahren zu ihrer Herstellung | |
| US4574155A (en) | Process for preparing 2-hydrazino-1,3-diazacycloalk-2-ene hydrohalides | |
| EP0029909B1 (de) | Verfahren zur Herstellung von Säureamiden, Verwendung des Verfahrens und Morpholino-äthyl-isocyanid | |
| CA1118445A (en) | N,n'-[bis(n-cyanoguanyl)] crystamine derivatives | |
| CH643821A5 (de) | Substituierte phenylacetylguanidine, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische praeparate. | |
| DE1795344B2 (de) | Verfahren zur herstellung von 3-aminoisothiazolen | |
| FR2525221A1 (fr) | Derives du furanne et sels d'addition de ces derives, leurs procedes de preparation et leurs applications en therapeutique | |
| GB2216521A (en) | Process for the preparation of 1,4-dihydro-pyridine derivatives | |
| CH529766A (de) | Verfahren zur Herstellung von Aryloxy-isoalkyl- 2-imidazolinen | |
| DE3242204A1 (de) | Verfahren zur herstellung von aminoalkylfuranen oder -thiophenen | |
| US4383115A (en) | Imino-alkyl and amino-nitrile cyano-guanidines | |
| EP0004535A2 (de) | Verfahren zur Herstellung von 4-Methyl-5-((2-aminoäthyl)-thiomethyl)-imidazol-dihydrochlorid | |
| FR2569692A1 (fr) | Procede de preparation de derives de guanidinothiazole | |
| CH616665A5 (en, 2012) | ||
| US5089612A (en) | Thiadiazine compound and method for preparing same | |
| SU465784A3 (ru) | Способ получени замещенных бигуанида | |
| AT400146B (de) | Verfahren zur herstellung von 1-(2-((5- | |
| EP0202461A1 (de) | Substituierte 2-(N-Alkinyl-N-phenylamino)imidazolinderivate, deren Säureadditionssalze, diese enthaltende Arzneimittel und Verfahren zu deren Herstellung | |
| DE4216028A1 (de) | 2-(Substituierte Imino)-thiazolidin-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel sowie ihre Verwendung | |
| DE3332148A1 (de) | Thiazolderivate, verfahren zu deren herstellung und diese enthaltende arzneimittel | |
| JP3081359B2 (ja) | ２−アミノ−１−フェニル−１−エタノール誘導体 |