JPH0314027B2 - - Google Patents
Info
- Publication number
- JPH0314027B2 JPH0314027B2 JP57027042A JP2704282A JPH0314027B2 JP H0314027 B2 JPH0314027 B2 JP H0314027B2 JP 57027042 A JP57027042 A JP 57027042A JP 2704282 A JP2704282 A JP 2704282A JP H0314027 B2 JPH0314027 B2 JP H0314027B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- formula
- represented
- imidazole derivative
- derivative according
- 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 20
- -1 1,3-disubstituted imidazole Chemical class 0.000 claims description 17
- 150000002460 imidazoles Chemical class 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 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 38
- 238000000034 method Methods 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000002994 raw material Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- VIHYIVKEECZGOU-UHFFFAOYSA-N N-acetylimidazole Chemical compound CC(=O)N1C=CN=C1 VIHYIVKEECZGOU-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- JBOIAZWJIACNJF-UHFFFAOYSA-N 1h-imidazole;hydroiodide Chemical compound [I-].[NH2+]1C=CN=C1 JBOIAZWJIACNJF-UHFFFAOYSA-N 0.000 description 2
- BKJFDZSBZWHRNH-UHFFFAOYSA-N 8-bromooctanoic acid Chemical compound OC(=O)CCCCCCCBr BKJFDZSBZWHRNH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 108010069102 Thromboxane-A synthase Proteins 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZTTWQKYKGNLCCA-UHFFFAOYSA-N 2-methyl-10H-thieno[2,3-b][1,5]benzodiazepin-4-amine Chemical compound N1C2=CC=CC=C2N=C(N)C2=C1SC(C)=C2 ZTTWQKYKGNLCCA-UHFFFAOYSA-N 0.000 description 1
- JLPQXFFMVVPIRW-UHFFFAOYSA-N 7-bromoheptanoic acid Chemical compound OC(=O)CCCCCCBr JLPQXFFMVVPIRW-UHFFFAOYSA-N 0.000 description 1
- IGNBKLCFKTYIRI-UHFFFAOYSA-N 7-chloroheptanoic acid Chemical compound OC(=O)CCCCCCCl IGNBKLCFKTYIRI-UHFFFAOYSA-N 0.000 description 1
- ZJMQLPOJWFYMME-UHFFFAOYSA-N 7-iodoheptanoic acid Chemical compound OC(=O)CCCCCCI ZJMQLPOJWFYMME-UHFFFAOYSA-N 0.000 description 1
- ZRJDOTOHSGMNJK-UHFFFAOYSA-N 8-bromo-2,2-dimethyloctanoic acid Chemical compound OC(=O)C(C)(C)CCCCCCBr ZRJDOTOHSGMNJK-UHFFFAOYSA-N 0.000 description 1
- GHBKZAJXCXDEAK-UHFFFAOYSA-N 8-bromo-2-methyloctanoic acid Chemical compound OC(=O)C(C)CCCCCCBr GHBKZAJXCXDEAK-UHFFFAOYSA-N 0.000 description 1
- SJHCDMKHMIJAIW-UHFFFAOYSA-N 8-chloro-2,2-dimethyloctanoic acid Chemical compound OC(=O)C(C)(C)CCCCCCCl SJHCDMKHMIJAIW-UHFFFAOYSA-N 0.000 description 1
- BGYPPYWDTVHCLI-UHFFFAOYSA-N 8-chloro-2-methyloctanoic acid Chemical compound OC(=O)C(C)CCCCCCCl BGYPPYWDTVHCLI-UHFFFAOYSA-N 0.000 description 1
- SCTRLHIAVHHIEJ-UHFFFAOYSA-N 8-chlorooctanoic acid Chemical compound OC(=O)CCCCCCCCl SCTRLHIAVHHIEJ-UHFFFAOYSA-N 0.000 description 1
- KDOIUCVMDLDXOP-UHFFFAOYSA-N 8-imidazol-1-yloctanoic acid;hydrochloride Chemical compound Cl.OC(=O)CCCCCCCN1C=CN=C1 KDOIUCVMDLDXOP-UHFFFAOYSA-N 0.000 description 1
- ATZMBJOEEVXQPA-UHFFFAOYSA-N 8-iodooctanoic acid Chemical compound OC(=O)CCCCCCCI ATZMBJOEEVXQPA-UHFFFAOYSA-N 0.000 description 1
- XEGRKZRPTBNSMN-UHFFFAOYSA-N 9-bromononanoic acid Chemical compound OC(=O)CCCCCCCCBr XEGRKZRPTBNSMN-UHFFFAOYSA-N 0.000 description 1
- DFJLDESPZKERQH-UHFFFAOYSA-N 9-chlorononanoic acid Chemical compound OC(=O)CCCCCCCCCl DFJLDESPZKERQH-UHFFFAOYSA-N 0.000 description 1
- KNTGUFLHSQVAHE-UHFFFAOYSA-N 9-iodononanoic acid Chemical compound OC(=O)CCCCCCCCI KNTGUFLHSQVAHE-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- GDBUORNHWAZSNU-UHFFFAOYSA-N N-propanoylimidazole Chemical compound CCC(=O)N1C=CN=C1 GDBUORNHWAZSNU-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- SHOBMTILPVNCAD-UHFFFAOYSA-N ethyl 8-bromo-2-methyloctanoate Chemical compound CCOC(=O)C(C)CCCCCCBr SHOBMTILPVNCAD-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 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
- 150000004693 imidazolium salts Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57027042A JPS58144375A (ja) | 1982-02-22 | 1982-02-22 | 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 |
|---|---|---|---|
| JP57027042A JPS58144375A (ja) | 1982-02-22 | 1982-02-22 | 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 |
|---|---|
| JPS58144375A JPS58144375A (ja) | 1983-08-27 |
| JPH0314027B2 true JPH0314027B2 (en, 2012) | 1991-02-25 |
Family
ID=12210005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57027042A Granted JPS58144375A (ja) | 1982-02-22 | 1982-02-22 | 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) | JPS58144375A (en, 2012) |
-
1982
- 1982-02-22 JP JP57027042A patent/JPS58144375A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58144375A (ja) | 1983-08-27 |
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