JPH05389B2 - - Google Patents
Info
- Publication number
- JPH05389B2 JPH05389B2 JP63009771A JP977188A JPH05389B2 JP H05389 B2 JPH05389 B2 JP H05389B2 JP 63009771 A JP63009771 A JP 63009771A JP 977188 A JP977188 A JP 977188A JP H05389 B2 JPH05389 B2 JP H05389B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- cimetidine
- cyano
- imidazole
- guanidine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229960001380 cimetidine Drugs 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 10
- GAIOTNZPXCFNJU-UHFFFAOYSA-N 1-(2-chloroethyl)-3-cyano-2-methylguanidine Chemical compound N#CNC(=NC)NCCCl GAIOTNZPXCFNJU-UHFFFAOYSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- -1 5-methyl-1H-imidazol-4-yl Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 claims 1
- AQIXAKUUQRKLND-UHFFFAOYSA-N cimetidine Chemical compound N#C/N=C(/NC)NCCSCC=1N=CNC=1C AQIXAKUUQRKLND-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical compound O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 description 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 3
- GCYDEHNKSNMNMN-UHFFFAOYSA-N (5-methyl-1h-imidazol-4-yl)methanethiol Chemical compound CC=1NC=NC=1CS GCYDEHNKSNMNMN-UHFFFAOYSA-N 0.000 description 2
- BSYXWUSCBKBFLM-UHFFFAOYSA-N (5-methyl-1h-imidazol-4-yl)methanethiol;hydrochloride Chemical compound Cl.CC=1N=CNC=1CS BSYXWUSCBKBFLM-UHFFFAOYSA-N 0.000 description 2
- FNMHARGLJLWHAA-UHFFFAOYSA-N 1-(2-bromoethyl)-3-cyano-2-methylguanidine Chemical compound N#CNC(=NC)NCCBr FNMHARGLJLWHAA-UHFFFAOYSA-N 0.000 description 2
- KWULCRGWFZACSD-UHFFFAOYSA-N 2-(2-chloroethyl)guanidine Chemical compound NC(N)=NCCCl KWULCRGWFZACSD-UHFFFAOYSA-N 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 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
- AXJZCJSXNZZMDU-UHFFFAOYSA-N (5-methyl-1h-imidazol-4-yl)methanol Chemical group CC=1N=CNC=1CO AXJZCJSXNZZMDU-UHFFFAOYSA-N 0.000 description 1
- CIYWXBAEXXLEBF-UHFFFAOYSA-N 2-(5-methyl-1h-imidazol-4-yl)ethanethiol Chemical compound CC=1N=CNC=1CCS CIYWXBAEXXLEBF-UHFFFAOYSA-N 0.000 description 1
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 1
- QYCSUYJIUAAHRF-UHFFFAOYSA-N 2-ethoxy-2-(2-oxopropanoyl)propanedithial Chemical compound C(C)OC(C(C(C)=O)=O)(C=S)C=S QYCSUYJIUAAHRF-UHFFFAOYSA-N 0.000 description 1
- APZXPRHPPCTRHN-UHFFFAOYSA-N 4-(chloromethyl)-5-methyl-1h-imidazole Chemical compound CC=1NC=NC=1CCl APZXPRHPPCTRHN-UHFFFAOYSA-N 0.000 description 1
- ZOHLKTFCEUOOOQ-UHFFFAOYSA-N 4-(methoxymethyl)-5-methyl-1h-imidazole Chemical compound COCC=1N=CNC=1C ZOHLKTFCEUOOOQ-UHFFFAOYSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- IULFXBLVJIPESI-UHFFFAOYSA-N bis(methylsulfanyl)methylidenecyanamide Chemical compound CSC(SC)=NC#N IULFXBLVJIPESI-UHFFFAOYSA-N 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 1
- UMTFPTCPRUEQHM-UHFFFAOYSA-N dicyanolead Chemical compound N#C[Pb]C#N UMTFPTCPRUEQHM-UHFFFAOYSA-N 0.000 description 1
- 210000004211 gastric acid Anatomy 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances 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
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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU91/87A YU45030B (en) | 1987-01-23 | 1987-01-23 | Process for preparing crystalline cimetidine |
| YU91/87 | 1987-01-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63192757A JPS63192757A (ja) | 1988-08-10 |
| JPH05389B2 true JPH05389B2 (US08063081-20111122-C00044.png) | 1993-01-05 |
Family
ID=25548294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63009771A Granted JPS63192757A (ja) | 1987-01-23 | 1988-01-21 | シメチジンの製造法 |
Country Status (6)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6362202B1 (en) | 1999-03-02 | 2002-03-26 | Sepracor Inc. | Methods and compositions using (−) norcisapride in combination with proton pump inhibitors or H2 receptor antagonists |
| US6353005B1 (en) | 1999-03-02 | 2002-03-05 | Sepracor, Inc. | Method and compositions using (+) norcisapride in combination with proton pump inhibitors or H2 receptor antagonist |
| CN105541723A (zh) * | 2015-12-17 | 2016-05-04 | 石家庄市普力制药有限公司 | 一种西咪替丁粗品的结晶工艺 |
Family Cites Families (3)
| 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 |
| WO1980001694A1 (en) * | 1979-02-14 | 1980-08-21 | Rech Syntheses Organ | Imino-alkyl and amino-nitryl cyano-guanidinze |
| YU44053B (en) * | 1986-05-08 | 1990-02-28 | Lek Tovarna Farmacevtskih | Process for obtaining 4(5)-methyl-5(4)-thiomethyl imidazole |
-
1987
- 1987-01-23 YU YU91/87A patent/YU45030B/xx unknown
- 1987-01-23 SI SI8710091A patent/SI8710091A8/sl unknown
-
1988
- 1988-01-05 EP EP88100081A patent/EP0279161B1/en not_active Expired - Lifetime
- 1988-01-05 DE DE3886786T patent/DE3886786T2/de not_active Expired - Fee Related
- 1988-01-21 JP JP63009771A patent/JPS63192757A/ja active Granted
- 1988-01-25 US US07/147,423 patent/US4855439A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| YU45030B (en) | 1991-06-30 |
| YU9187A (en) | 1988-12-31 |
| JPS63192757A (ja) | 1988-08-10 |
| EP0279161A3 (en) | 1989-05-10 |
| EP0279161A2 (en) | 1988-08-24 |
| SI8710091A8 (en) | 1996-06-30 |
| EP0279161B1 (en) | 1994-01-05 |
| DE3886786T2 (de) | 1994-06-01 |
| DE3886786D1 (de) | 1994-02-17 |
| US4855439A (en) | 1989-08-08 |
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