DK169920B1 - Fremgangsmåde til fremstilling af N-sulfamyl-3-(2-guanidinothiazol-4-ylmethylthio)propionamidin - Google Patents
Fremgangsmåde til fremstilling af N-sulfamyl-3-(2-guanidinothiazol-4-ylmethylthio)propionamidin Download PDFInfo
- Publication number
- DK169920B1 DK169920B1 DK434586A DK434586A DK169920B1 DK 169920 B1 DK169920 B1 DK 169920B1 DK 434586 A DK434586 A DK 434586A DK 434586 A DK434586 A DK 434586A DK 169920 B1 DK169920 B1 DK 169920B1
- Authority
- DK
- Denmark
- Prior art keywords
- guanidino
- thiazol
- sulfamyl
- famotidine
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- XUFQPHANEAPEMJ-UHFFFAOYSA-N famotidine Chemical compound NC(N)=NC1=NC(CSCCC(N)=NS(N)(=O)=O)=CS1 XUFQPHANEAPEMJ-UHFFFAOYSA-N 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 7
- 229960001596 famotidine Drugs 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 238000005804 alkylation reaction Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- AHNNULCXEIGUHA-UHFFFAOYSA-N 2-[4-(sulfanylmethyl)-1,3-thiazol-2-yl]guanidine Chemical compound NC(N)=NC1=NC(CS)=CS1 AHNNULCXEIGUHA-UHFFFAOYSA-N 0.000 claims description 6
- QZFCNUHDVLMXDA-UHFFFAOYSA-N 3-chloro-n'-sulfamoylpropanimidamide Chemical compound ClCCC(N)=NS(N)(=O)=O QZFCNUHDVLMXDA-UHFFFAOYSA-N 0.000 claims description 6
- 238000011065 in-situ storage Methods 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- VJAMCQFRFWRULO-UHFFFAOYSA-N thiourea;dihydrochloride Chemical compound Cl.Cl.NC(S)=N VJAMCQFRFWRULO-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 6
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- -1 sulfoxide compound Chemical class 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- FTKAAVQOOXXUGW-UHFFFAOYSA-N [4-[[amino(azaniumylidene)methyl]sulfanylmethyl]-1,3-thiazol-2-yl]-(diaminomethylidene)azanium;dichloride Chemical compound Cl.Cl.NC(=N)SCC1=CSC(N=C(N)N)=N1 FTKAAVQOOXXUGW-UHFFFAOYSA-N 0.000 description 4
- DOWMJKWFABWEAH-UHFFFAOYSA-N n'-sulfamoylprop-2-enimidamide Chemical compound NS(=O)(=O)NC(=N)C=C DOWMJKWFABWEAH-UHFFFAOYSA-N 0.000 description 4
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical class SC LSDPWZHWYPCBBB-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FSKYYRZENXOYAP-UHFFFAOYSA-N 2-[4-(2-cyanoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine Chemical compound NC(=N)NC1=NC(CSCCC#N)=CS1 FSKYYRZENXOYAP-UHFFFAOYSA-N 0.000 description 2
- INDWVHABTMSBCJ-UHFFFAOYSA-N 3-methylsulfanylpropanenitrile Chemical compound CSCCC#N INDWVHABTMSBCJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229960001380 cimetidine Drugs 0.000 description 2
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- PPIZMFIUBYYLRB-UHFFFAOYSA-N 1,1-dioxo-3,4-dihydro-2h-1,2,6-thiadiazin-5-amine Chemical compound NC1=NS(=O)(=O)NCC1 PPIZMFIUBYYLRB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- IVLQMIVEODCGLH-UHFFFAOYSA-N 3-chloro-n'-sulfamoylpropanimidamide;hydrochloride Chemical compound Cl.ClCCC(/N)=N/S(N)(=O)=O IVLQMIVEODCGLH-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- LRFIDMFTYCHEFX-UHFFFAOYSA-N 3-chloropropanimidamide;hydrochloride Chemical compound Cl.NC(=N)CCCl LRFIDMFTYCHEFX-UHFFFAOYSA-N 0.000 description 1
- QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical class OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 description 1
- RNZYZIJPRMPMED-UHFFFAOYSA-N 3-methylsulfanyl-n'-sulfamoylpropanimidamide Chemical compound CSCCC(=N)NS(N)(=O)=O RNZYZIJPRMPMED-UHFFFAOYSA-N 0.000 description 1
- 102000003710 Histamine H2 Receptors Human genes 0.000 description 1
- 108090000050 Histamine H2 Receptors Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010022714 Intestinal ulcer Diseases 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- QUBHCMPAOWIZMT-UHFFFAOYSA-N [2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methyl carbamimidothioate Chemical compound NC(N)=NC1=NC(CSC(N)=N)=CS1 QUBHCMPAOWIZMT-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 230000002280 anti-androgenic effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000011210 chromatographic step Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008240 homogeneous mixture Substances 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- PLPIVSVTRFQJFM-UHFFFAOYSA-N methanimidoyl methanimidate;hydrochloride Chemical compound Cl.N=COC=N PLPIVSVTRFQJFM-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/28—Radicals substituted by nitrogen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU342485 | 1985-09-11 | ||
| HU853424A HU194845B (en) | 1985-09-11 | 1985-09-11 | Process for production of n-sulphamil-3-/2-guanidintiazolil-4-methil-tio/-propion-amidin |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK434586D0 DK434586D0 (da) | 1986-09-10 |
| DK434586A DK434586A (da) | 1987-03-12 |
| DK169920B1 true DK169920B1 (da) | 1995-04-03 |
Family
ID=10963968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK434586A DK169920B1 (da) | 1985-09-11 | 1986-09-10 | Fremgangsmåde til fremstilling af N-sulfamyl-3-(2-guanidinothiazol-4-ylmethylthio)propionamidin |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4835281A (fr) |
| JP (1) | JPH0645609B2 (fr) |
| KR (1) | KR910000237B1 (fr) |
| CN (1) | CN1013674B (fr) |
| AR (1) | AR240319A1 (fr) |
| AT (1) | AT386824B (fr) |
| AU (1) | AU587279B2 (fr) |
| BE (1) | BE905409A (fr) |
| CA (1) | CA1263120A (fr) |
| DD (1) | DD249479A5 (fr) |
| DK (1) | DK169920B1 (fr) |
| ES (1) | ES2001677A6 (fr) |
| FI (1) | FI86423C (fr) |
| GB (1) | GB2180237B (fr) |
| GE (1) | GEP19960471B (fr) |
| GR (1) | GR862308B (fr) |
| HU (1) | HU194845B (fr) |
| NL (1) | NL8602225A (fr) |
| NO (1) | NO163010C (fr) |
| PT (1) | PT83348B (fr) |
| SE (1) | SE8603797L (fr) |
| SU (1) | SU1450743A3 (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU194845B (en) * | 1985-09-11 | 1988-03-28 | Richter Gedeon Vegyeszet | Process for production of n-sulphamil-3-/2-guanidintiazolil-4-methil-tio/-propion-amidin |
| HU196775B (en) * | 1986-08-05 | 1989-01-30 | Richter Gedeon Vegyeszet | Process for production of morfologically unique new modifications of famotidin and medical compositions containing such substances |
| NO882037L (no) * | 1987-06-22 | 1988-12-23 | Marga Para La Investigacion Sa | Famotidin, polymerte former og fremstilling derav. |
| US5731442A (en) * | 1997-03-11 | 1998-03-24 | Albemarle Corporation | Synthesis of thiazole derivatives |
| US5856500A (en) * | 1997-03-11 | 1999-01-05 | Albemarle Corporation | Synthesis of thiazole derivatives |
| AU772188B2 (en) * | 1998-11-17 | 2004-04-08 | Nitromed, Inc. | Nitrosated and nitrosylated H2 receptor antagonist compounds, compositions and methods of use |
| WO2009058997A2 (fr) * | 2007-11-01 | 2009-05-07 | Biocept Inc. | Isolement non invasif d'acide nucléique fœtal |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6056143B2 (ja) * | 1979-08-02 | 1985-12-09 | 山之内製薬株式会社 | アミジン誘導体ならびにその製造法 |
| US4808589A (en) * | 1982-02-20 | 1989-02-28 | Smith Kline & French Laboratories Limited | Pyrimidone derivatives |
| US4496737A (en) | 1982-09-27 | 1985-01-29 | Merck & Co., Inc. | Process for preparing sulfamylamidine antisecretory agents |
| ES8504157A1 (es) * | 1983-10-07 | 1985-04-01 | Inke Sa | Procedimiento para la obtencion de (-1amino-3-(((2-((diaminometileno) amino)-4-tiazolil)metil)tio)propilideno)sulfamida |
| ES532239A0 (es) * | 1984-05-07 | 1985-08-01 | Inke Sa | Procedimiento para la obtencion de la 1-amino-3-2-diamino-metilen-amino-4-tiazolil-metil-tio-propiliden-sulfamida. |
| ES536322A0 (es) * | 1984-09-27 | 1985-08-01 | Bioiberica | Procedimiento para la obtencion del n-aminosolfenil-3-(((2-guanidin-4-tiazonil)metil)tio) propionamidina |
| ES8506664A1 (es) * | 1984-10-17 | 1985-08-01 | Inke Sa | Procedimiento para la obtencion de la (1-amino-3(((2-((diamino-metilen) amino)-4-tiazolil)metil)tio)propiliden)sulfamida |
| HU193608B (en) * | 1985-09-11 | 1987-11-30 | Richter Gedeon Vegyeszet | Process for production of new dervatives of n-sulphanol-propion-amidine |
| HU194845B (en) * | 1985-09-11 | 1988-03-28 | Richter Gedeon Vegyeszet | Process for production of n-sulphamil-3-/2-guanidintiazolil-4-methil-tio/-propion-amidin |
| JP3751649B2 (ja) * | 1994-12-01 | 2006-03-01 | 関西ペイント株式会社 | 自動車外板塗膜の一時保護方法 |
-
1985
- 1985-09-11 HU HU853424A patent/HU194845B/hu unknown
-
1986
- 1986-08-22 CA CA000516617A patent/CA1263120A/fr not_active Expired
- 1986-09-03 NL NL8602225A patent/NL8602225A/nl not_active Application Discontinuation
- 1986-09-08 AR AR305176A patent/AR240319A1/es active
- 1986-09-08 KR KR1019860007508A patent/KR910000237B1/ko not_active Expired
- 1986-09-09 DD DD86294264A patent/DD249479A5/de unknown
- 1986-09-09 SU SU864028107A patent/SU1450743A3/ru active
- 1986-09-09 GR GR862308A patent/GR862308B/el unknown
- 1986-09-10 NO NO863616A patent/NO163010C/no not_active IP Right Cessation
- 1986-09-10 AU AU62569/86A patent/AU587279B2/en not_active Expired
- 1986-09-10 FI FI863657A patent/FI86423C/fi not_active IP Right Cessation
- 1986-09-10 AT AT0243486A patent/AT386824B/de not_active IP Right Cessation
- 1986-09-10 BE BE0/217144A patent/BE905409A/fr not_active IP Right Cessation
- 1986-09-10 GB GB8621742A patent/GB2180237B/en not_active Expired
- 1986-09-10 DK DK434586A patent/DK169920B1/da not_active IP Right Cessation
- 1986-09-10 JP JP61211792A patent/JPH0645609B2/ja not_active Expired - Lifetime
- 1986-09-10 PT PT83348A patent/PT83348B/pt unknown
- 1986-09-10 SE SE8603797A patent/SE8603797L/xx not_active Application Discontinuation
- 1986-09-11 CN CN86105909A patent/CN1013674B/zh not_active Expired
- 1986-09-11 ES ES8601790A patent/ES2001677A6/es not_active Expired
-
1987
- 1987-07-23 US US07/077,095 patent/US4835281A/en not_active Expired - Lifetime
-
1993
- 1993-06-14 GE GEAP1993867A patent/GEP19960471B/en unknown
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