JPS623148B2 - - Google Patents
Info
- Publication number
- JPS623148B2 JPS623148B2 JP58010355A JP1035583A JPS623148B2 JP S623148 B2 JPS623148 B2 JP S623148B2 JP 58010355 A JP58010355 A JP 58010355A JP 1035583 A JP1035583 A JP 1035583A JP S623148 B2 JPS623148 B2 JP S623148B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- reaction
- cimetidine
- cyano
- ethyl
- 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
Links
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000006722 reduction reaction Methods 0.000 claims description 7
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 6
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 6
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 claims description 4
- 229940116357 potassium thiocyanate Drugs 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 3
- IGSAPGNIBICQPA-UHFFFAOYSA-N 2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound CC=1NC=NC=1CSCCNC(N)=N IGSAPGNIBICQPA-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000013078 crystal Substances 0.000 description 15
- AQIXAKUUQRKLND-UHFFFAOYSA-N cimetidine Chemical compound N#C/N=C(/NC)NCCSCC=1N=CNC=1C AQIXAKUUQRKLND-UHFFFAOYSA-N 0.000 description 14
- 229960001380 cimetidine Drugs 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 239000007868 Raney catalyst Substances 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- -1 4-methyl-5-imidazolyl Chemical group 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 239000012000 urushibara nickel Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58010355A JPS59137464A (ja) | 1983-01-25 | 1983-01-25 | イミダゾ−ル系化合物の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58010355A JPS59137464A (ja) | 1983-01-25 | 1983-01-25 | イミダゾ−ル系化合物の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59137464A JPS59137464A (ja) | 1984-08-07 |
| JPS623148B2 true JPS623148B2 (en, 2012) | 1987-01-23 |
Family
ID=11747867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58010355A Granted JPS59137464A (ja) | 1983-01-25 | 1983-01-25 | イミダゾ−ル系化合物の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59137464A (en, 2012) |
-
1983
- 1983-01-25 JP JP58010355A patent/JPS59137464A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59137464A (ja) | 1984-08-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4537900A (en) | Cimetidine Z, a new crystal modification of cimetidine | |
| JPS623148B2 (en, 2012) | ||
| JPH0136462B2 (en, 2012) | ||
| JPS636063B2 (en, 2012) | ||
| JPS60105661A (ja) | シアノグアニジン誘導体及びその製造方法 | |
| JP2909145B2 (ja) | β―ラクタマーゼ抑止剤の製法 | |
| JP2811525B2 (ja) | ２−ブチル−４−クロロ−５−フォルミルイミダゾールの合成方法 | |
| JPS6056139B2 (ja) | シアノグアニジン誘導体の製造法 | |
| JP2685120B2 (ja) | ジチアゾリウム塩の製造方法 | |
| JPH033665B2 (en, 2012) | ||
| JPS622589B2 (en, 2012) | ||
| JPS622592B2 (en, 2012) | ||
| CN120383564A (zh) | 一种咪唑苯脲的制备方法 | |
| JPS622590B2 (en, 2012) | ||
| JPS6317869A (ja) | ２−低級アルキル−４−アミノ−５−ホルミルピリミジンの製造法 | |
| JPS63211264A (ja) | インドリン類の製造法 | |
| JPS6067466A (ja) | イミダゾ−ル誘導体の製造方法 | |
| JPS59122475A (ja) | イミダゾ−ル系化合物の製法 | |
| JP3081359B2 (ja) | ２−アミノ−１−フェニル−１−エタノール誘導体 | |
| JPH0665665B2 (ja) | １，３−ジメチル−２−イミダゾリジノンの製造方法 | |
| JPS62106067A (ja) | アリ−ルシアナミドの製造方法 | |
| JPH0665200A (ja) | フタルイミド化合物の製造法 | |
| JPS6056708B2 (ja) | イミダゾ−ル誘導体の製造方法 | |
| JPS62132867A (ja) | イミダゾ−ル誘導体の製法 | |
| JPH04182470A (ja) | Ｎ―シアノ―ｎ’―メチル―ｎ”―［２―［［（５―メチル―１ｈ―４―イミダゾリル）メチル］チオ］エチル］グアニジンの製造方法 |