JPS59130273A - イミダゾ−ル系化合物の製造法 - Google Patents
イミダゾ−ル系化合物の製造法Info
- Publication number
- JPS59130273A JPS59130273A JP58004632A JP463283A JPS59130273A JP S59130273 A JPS59130273 A JP S59130273A JP 58004632 A JP58004632 A JP 58004632A JP 463283 A JP463283 A JP 463283A JP S59130273 A JPS59130273 A JP S59130273A
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- crown
- imidazole
- cyano
- formula
- 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.)
- Granted
Links
- -1 imidazole compound Chemical class 0.000 title claims abstract description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title description 11
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims abstract description 9
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 3
- 150000001340 alkali metals Chemical group 0.000 claims abstract description 3
- 229910052784 alkaline earth metal Chemical group 0.000 claims abstract 2
- 150000001342 alkaline earth metals Chemical group 0.000 claims abstract 2
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 claims description 18
- 229960001380 cimetidine Drugs 0.000 claims description 18
- 239000013078 crystal Substances 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract description 9
- 150000003983 crown ethers Chemical class 0.000 abstract description 9
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 abstract description 2
- 230000000767 anti-ulcer Effects 0.000 abstract description 2
- 229910052752 metalloid Inorganic materials 0.000 abstract 2
- 150000002357 guanidines Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000005905 mesyloxy group Chemical group 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 abstract 1
- 239000000047 product Substances 0.000 description 9
- 238000000862 absorption spectrum Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- XKEHLMZHBXCJGZ-UHFFFAOYSA-N 1,4,7,10,13,16,19-heptaoxacyclohenicosane Chemical compound C1COCCOCCOCCOCCOCCOCCO1 XKEHLMZHBXCJGZ-UHFFFAOYSA-N 0.000 description 1
- GAIOTNZPXCFNJU-UHFFFAOYSA-N 1-(2-chloroethyl)-3-cyano-2-methylguanidine Chemical compound N#CNC(=NC)NCCCl GAIOTNZPXCFNJU-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- XTNKKKZZEGJQDP-UHFFFAOYSA-N 2-[(n-cyano-n'-methylcarbamimidoyl)amino]ethyl 4-methylbenzenesulfonate Chemical compound N#CNC(=NC)NCCOS(=O)(=O)C1=CC=C(C)C=C1 XTNKKKZZEGJQDP-UHFFFAOYSA-N 0.000 description 1
- KEWLVUBYGUZFKX-UHFFFAOYSA-N 2-ethylguanidine Chemical compound CCNC(N)=N KEWLVUBYGUZFKX-UHFFFAOYSA-N 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 101150084411 crn1 gene Proteins 0.000 description 1
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58004632A JPS59130273A (ja) | 1983-01-14 | 1983-01-14 | イミダゾ−ル系化合物の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58004632A JPS59130273A (ja) | 1983-01-14 | 1983-01-14 | イミダゾ−ル系化合物の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59130273A true JPS59130273A (ja) | 1984-07-26 |
| JPS622591B2 JPS622591B2 (enrdf_load_stackoverflow) | 1987-01-20 |
Family
ID=11589384
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58004632A Granted JPS59130273A (ja) | 1983-01-14 | 1983-01-14 | イミダゾ−ル系化合物の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59130273A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113234018A (zh) * | 2021-05-11 | 2021-08-10 | 石家庄市普力制药有限公司 | 一种西咪替丁的生产方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5340771A (en) * | 1976-09-21 | 1978-04-13 | Smith Kline French Lab | Novel polymorph of heterocyclic compound |
| JPS5440547A (en) * | 1977-09-07 | 1979-03-30 | Seikosha Kk | Device for adjusting output frequency of frequency divider |
| JPS54130566A (en) * | 1977-12-28 | 1979-10-09 | Om Lab Sa | Manufacture of guanidine derivative |
-
1983
- 1983-01-14 JP JP58004632A patent/JPS59130273A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5340771A (en) * | 1976-09-21 | 1978-04-13 | Smith Kline French Lab | Novel polymorph of heterocyclic compound |
| JPS5440547A (en) * | 1977-09-07 | 1979-03-30 | Seikosha Kk | Device for adjusting output frequency of frequency divider |
| JPS54130566A (en) * | 1977-12-28 | 1979-10-09 | Om Lab Sa | Manufacture of guanidine derivative |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113234018A (zh) * | 2021-05-11 | 2021-08-10 | 石家庄市普力制药有限公司 | 一种西咪替丁的生产方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS622591B2 (enrdf_load_stackoverflow) | 1987-01-20 |
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