JPH0340024B2 - - Google Patents
Info
- Publication number
- JPH0340024B2 JPH0340024B2 JP57033463A JP3346382A JPH0340024B2 JP H0340024 B2 JPH0340024 B2 JP H0340024B2 JP 57033463 A JP57033463 A JP 57033463A JP 3346382 A JP3346382 A JP 3346382A JP H0340024 B2 JPH0340024 B2 JP H0340024B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- formula
- compound represented
- group
- represented
- 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
- 238000004519 manufacturing process Methods 0.000 claims description 24
- -1 1,3-disubstituted imidazole Chemical class 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000002460 imidazoles Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 47
- 238000006243 chemical reaction Methods 0.000 description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000002994 raw material Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 5
- VWUCIBOKNZGWLX-UHFFFAOYSA-N 1h-imidazol-1-ium;bromide Chemical compound [Br-].C1=C[NH+]=CN1 VWUCIBOKNZGWLX-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VIHYIVKEECZGOU-UHFFFAOYSA-N N-acetylimidazole Chemical compound CC(=O)N1C=CN=C1 VIHYIVKEECZGOU-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 230000002921 anti-spasmodic effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- OHPWPYMGPYQPTO-UHFFFAOYSA-N 2-bromo-1-[4-(2-phenylethyl)phenyl]ethanone Chemical group C1=CC(C(=O)CBr)=CC=C1CCC1=CC=CC=C1 OHPWPYMGPYQPTO-UHFFFAOYSA-N 0.000 description 2
- IQEIGQFNDLINOT-UHFFFAOYSA-N 2-chloro-1-(4-phenylphenyl)ethanone Chemical compound C1=CC(C(=O)CCl)=CC=C1C1=CC=CC=C1 IQEIGQFNDLINOT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229940124575 antispasmodic agent Drugs 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000012156 elution solvent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LRWLZSXTTFWNTO-UHFFFAOYSA-N 2-bromo-1-(4-phenylphenyl)propan-1-one Chemical group C1=CC(C(=O)C(Br)C)=CC=C1C1=CC=CC=C1 LRWLZSXTTFWNTO-UHFFFAOYSA-N 0.000 description 1
- PVWFUCRYWYDOJS-UHFFFAOYSA-N 2-imidazol-1-yl-1-(4-phenylphenyl)propan-1-ol Chemical group C1=CN=CN1C(C)C(O)C(C=C1)=CC=C1C1=CC=CC=C1 PVWFUCRYWYDOJS-UHFFFAOYSA-N 0.000 description 1
- CXVYHVRNSQXTQO-UHFFFAOYSA-N 2-imidazol-1-yl-1-(4-phenylphenyl)propan-1-ol;hydrochloride Chemical compound [Cl-].C1=CN=C[NH+]1C(C)C(O)C(C=C1)=CC=C1C1=CC=CC=C1 CXVYHVRNSQXTQO-UHFFFAOYSA-N 0.000 description 1
- ZMWDZKFGQNUTMM-UHFFFAOYSA-N 2-imidazol-1-yl-1-(4-phenylphenyl)propan-1-one Chemical group C1=CN=CN1C(C)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ZMWDZKFGQNUTMM-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- GDBUORNHWAZSNU-UHFFFAOYSA-N N-propanoylimidazole Chemical compound CCC(=O)N1C=CN=C1 GDBUORNHWAZSNU-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- JEGIFBGJZPYMJS-UHFFFAOYSA-N imidazol-1-yl(phenyl)methanone Chemical compound C1=CN=CN1C(=O)C1=CC=CC=C1 JEGIFBGJZPYMJS-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57033463A JPS58150567A (ja) | 1982-03-03 | 1982-03-03 | 新規な１，３−二置換イミダゾ−ル誘導体およびその製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57033463A JPS58150567A (ja) | 1982-03-03 | 1982-03-03 | 新規な１，３−二置換イミダゾ−ル誘導体およびその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58150567A JPS58150567A (ja) | 1983-09-07 |
| JPH0340024B2 true JPH0340024B2 (es) | 1991-06-17 |
Family
ID=12387231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57033463A Granted JPS58150567A (ja) | 1982-03-03 | 1982-03-03 | 新規な１，３−二置換イミダゾ−ル誘導体およびその製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58150567A (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4683312A (en) * | 1984-11-13 | 1987-07-28 | Eli Lilly And Company | Imidazolium hypoglycemic agents |
| US4609670A (en) * | 1984-11-13 | 1986-09-02 | Eli Lilly And Company | Imidazolium hypoglycemic agents |
-
1982
- 1982-03-03 JP JP57033463A patent/JPS58150567A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58150567A (ja) | 1983-09-07 |
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