JPS6256871B2 - - Google Patents
Info
- Publication number
- JPS6256871B2 JPS6256871B2 JP7950879A JP7950879A JPS6256871B2 JP S6256871 B2 JPS6256871 B2 JP S6256871B2 JP 7950879 A JP7950879 A JP 7950879A JP 7950879 A JP7950879 A JP 7950879A JP S6256871 B2 JPS6256871 B2 JP S6256871B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- general formula
- lower alkyl
- alkyl group
- compound
- 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
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001409 amidines Chemical class 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000027119 gastric acid secretion Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000001078 anti-cholinergic effect Effects 0.000 description 3
- -1 methoxy, ethoxy, propoxy Chemical group 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- AQFWNELGMODZGC-UHFFFAOYSA-N o-ethylhydroxylamine Chemical compound CCON AQFWNELGMODZGC-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- PBQKWXUCMGTHNU-UHFFFAOYSA-N 2-methylsulfanylpropanamide Chemical compound CSC(C)C(N)=O PBQKWXUCMGTHNU-UHFFFAOYSA-N 0.000 description 1
- GBNBIQDPFCZDCN-UHFFFAOYSA-N 3-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]-n'-hydroxypropanimidamide Chemical compound NC(=N)NC1=NC(CSCCC(N)=NO)=CS1 GBNBIQDPFCZDCN-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- GRKUXCWELVWVMZ-UHFFFAOYSA-N amino acetate Chemical compound CC(=O)ON GRKUXCWELVWVMZ-UHFFFAOYSA-N 0.000 description 1
- SDBCCDNTZKHGBJ-UHFFFAOYSA-N amino butanoate Chemical compound CCCC(=O)ON SDBCCDNTZKHGBJ-UHFFFAOYSA-N 0.000 description 1
- KTYVHLCLTPLSGC-UHFFFAOYSA-N amino propanoate Chemical compound CCC(=O)ON KTYVHLCLTPLSGC-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229940069428 antacid Drugs 0.000 description 1
- 239000003159 antacid agent Substances 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (27)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7950879A JPS565469A (en) | 1979-06-23 | 1979-06-23 | Novel amidine derivative and its preparation |
| AT0103080A AT374800B (de) | 1979-03-06 | 1980-02-25 | Verfahren zur herstellung neuer guanidinothiazole und von deren salzen |
| PH23689A PH16099A (en) | 1979-03-06 | 1980-02-26 | Guanidinothiazole compounds,process for preparing them and medical composition containing them |
| FI800591A FI70890C (fi) | 1979-03-06 | 1980-02-27 | Foerfarande foer framstaellning av farmakologiskt vaerdefulla guanidinotiazolfoereningar |
| AU55975/80A AU534329B2 (en) | 1979-03-06 | 1980-02-28 | Guanioinothiazoles |
| GR61334A GR67011B (xx) | 1979-03-06 | 1980-03-03 | |
| DE19803008056 DE3008056A1 (de) | 1979-03-06 | 1980-03-03 | Guanidinothiazolverbindungen, verfahren zu ihrer herstellung und arzneimittel |
| FR8004690A FR2450827A1 (fr) | 1979-03-06 | 1980-03-03 | Composes du guanidinothiazole utiles comme inhibiteurs des secretions d'acide gastrique, leurs procedes de preparation et les compositions medicales contenant de tels composes |
| CH171680A CH644114A5 (de) | 1979-03-06 | 1980-03-04 | Guanidinothiazolverbindungen, verfahren zu ihrer herstellung und sie enthaltende arzneimittel. |
| PT70899A PT70899A (en) | 1979-03-06 | 1980-03-04 | Process for preparing useful guanidinothiazole compounds |
| CA000346986A CA1145345A (en) | 1979-03-06 | 1980-03-04 | Process for preparing guanidinothiazole compounds |
| MX8011198U MX7406E (es) | 1979-03-06 | 1980-03-05 | Procedimiento para preparar compuestos de guanidinotiazol |
| UA2891152A UA5926A1 (uk) | 1979-03-06 | 1980-03-05 | Спосіб одержання гуанідінотіазольних сполучень |
| DK093580A DK157132C (da) | 1979-03-06 | 1980-03-05 | Analogifremgangsmaade til fremstilling af guanidinothiazolforbindelser eller syreadditionssalte deraf |
| SE8001691A SE447253B (sv) | 1979-03-06 | 1980-03-05 | Nya guanidinotiazolforeningar |
| ES489222A ES489222A0 (es) | 1979-03-06 | 1980-03-05 | Un procedimiento para preparar un compuesto de guanidinotia-zol |
| SU802891152A SU876056A3 (ru) | 1979-03-06 | 1980-03-05 | Способ получени гуанидинотиазольных соединений |
| MX808685U MX6187E (es) | 1979-03-06 | 1980-03-05 | Procedimiento para preparar compuestos de guanidinotiazol |
| MX8011289U MX7292E (es) | 1979-03-06 | 1980-03-05 | Procedimiento para preparar compuestos de guanidinotiazol |
| IT67346/80A IT1165509B (it) | 1979-03-06 | 1980-03-05 | Composti guanidino tiazolici particolarmente utili come inibitori di secrezione di acidi gastrici e procedimento per la loro preparazione |
| YU622/80A YU42966B (en) | 1979-03-06 | 1980-03-06 | Process for obtaining guanidine thiazole compounds |
| US06/127,902 US4362736A (en) | 1979-03-06 | 1980-03-06 | Guanidinothiazole compounds, and medical compositions containing them |
| NL8001361A NL8001361A (nl) | 1979-03-06 | 1980-03-06 | Guanidinothiazoolverbindingen, werkwijzen ter bereiding ervan, alsmede farmaceutische preparaten die de guanidinothiazoolverbindingen bevatten. |
| GB8007702A GB2052478B (en) | 1979-03-06 | 1980-03-06 | Guanidinothiazole compounds |
| SI8010622A SI8010622A8 (sl) | 1979-03-06 | 1980-03-06 | Postopek pridobivanja gvanidintiazolnih spojin |
| LV930547A LV5493A3 (lv) | 1979-03-06 | 1993-11-30 | Guanidinotiazolu savienojumu iegusanas panemiens |
| GEAP19942152A GEP19970667B (en) | 1979-03-06 | 1994-09-07 | Method of producing guanidinothiazole compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7950879A JPS565469A (en) | 1979-06-23 | 1979-06-23 | Novel amidine derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS565469A JPS565469A (en) | 1981-01-20 |
| JPS6256871B2 true JPS6256871B2 (xx) | 1987-11-27 |
Family
ID=13691881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7950879A Granted JPS565469A (en) | 1979-03-06 | 1979-06-23 | Novel amidine derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS565469A (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6061375A (ja) * | 1983-09-14 | 1985-04-09 | Nissan Shatai Co Ltd | 車両用サンドイッチ型防音，防振構造体の製造方法 |
| JPH0665620B2 (ja) * | 1986-12-18 | 1994-08-24 | 日本特殊塗料株式会社 | 車両用制振シート |
-
1979
- 1979-06-23 JP JP7950879A patent/JPS565469A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS565469A (en) | 1981-01-20 |
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