JPS6313429B2 - - Google Patents
Info
- Publication number
- JPS6313429B2 JPS6313429B2 JP12874380A JP12874380A JPS6313429B2 JP S6313429 B2 JPS6313429 B2 JP S6313429B2 JP 12874380 A JP12874380 A JP 12874380A JP 12874380 A JP12874380 A JP 12874380A JP S6313429 B2 JPS6313429 B2 JP S6313429B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- acid
- compound
- pyridyl
- chloroform
- 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
- -1 3,3-disubstituted propionamidine compound Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000002218 hypoglycaemic effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- MNKDACDKDSUAMA-UHFFFAOYSA-N 3-phenyl-3-pyridin-2-ylpropanimidamide Chemical compound C=1C=CC=NC=1C(CC(=N)N)C1=CC=CC=C1 MNKDACDKDSUAMA-UHFFFAOYSA-N 0.000 description 1
- VYIBCOSBNVFEIW-UHFFFAOYSA-N 3-phenylpropanamide Chemical compound NC(=O)CCC1=CC=CC=C1 VYIBCOSBNVFEIW-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003153 chemical reaction reagent 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
- 239000007884 disintegrant Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 229940126904 hypoglycaemic agent Drugs 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
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 229940127017 oral antidiabetic Drugs 0.000 description 1
- 239000003538 oral antidiabetic agent Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12874380A JPS5753451A (en) | 1980-09-17 | 1980-09-17 | 3,3-disusbtituted rropionamidine compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12874380A JPS5753451A (en) | 1980-09-17 | 1980-09-17 | 3,3-disusbtituted rropionamidine compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5753451A JPS5753451A (en) | 1982-03-30 |
| JPS6313429B2 true JPS6313429B2 (enrdf_load_stackoverflow) | 1988-03-25 |
Family
ID=14992351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12874380A Granted JPS5753451A (en) | 1980-09-17 | 1980-09-17 | 3,3-disusbtituted rropionamidine compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5753451A (enrdf_load_stackoverflow) |
-
1980
- 1980-09-17 JP JP12874380A patent/JPS5753451A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5753451A (en) | 1982-03-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU667107B2 (en) | Thiazolylvinylphenyl derivatives | |
| US4096151A (en) | Certain 3-cyanopyridine intermediates | |
| CA1223598A (en) | DOPAMINE-.beta.-HYDROXYLASE INHIBITORS | |
| WO2003037881A1 (fr) | Cristal a forme $g(a) ou $g(b) d'un derive acetanilinide | |
| RU2162081C2 (ru) | Способ получения ламотриджина и промежуточное соединение, используемое при его получении | |
| EP0508740B1 (en) | Thiazolidinedione derivatives, their production and their use | |
| WO2006090153A1 (en) | Process for preparing protected amiidines | |
| DE69215482T2 (de) | 2,2'-Alkylendiindolderivate, Verfahren zu ihrer Herstellung, sie enthaltende Arzneimittel und deren Verwendung als Ulcustherapeutikum | |
| DE3923675A1 (de) | Amonoalkylsubstituierte 2-aminothiazole und diese enthaltende therapeutische mittel | |
| JPS59216877A (ja) | 置換フエニル−２−（１ｈ）−ピリミジノン | |
| JPS6312063B2 (enrdf_load_stackoverflow) | ||
| JPS6313429B2 (enrdf_load_stackoverflow) | ||
| CN1034922A (zh) | 新四氢吡啶衍生物制备方法 | |
| US4361575A (en) | Substituted 2-phenylamino-2-imidazolines and salts thereof | |
| JPH0774205B2 (ja) | 新規イミダゾ−ル誘導体 | |
| JPH06758B2 (ja) | イミダゾール誘導体、その製法およびそれを含有する医薬 | |
| US4011323A (en) | Bi-4-[1-(quinazolinyl-4)piperidyls] and bis{4-[1-(quinazolinyl-4)piperidyl]alkanes} | |
| US4221798A (en) | Hypotensive 2-heterocycloamino-imidazolines | |
| US4479952A (en) | Monosubstituted piperazines | |
| GB1601991A (en) | Pyrido (2,1-b) quinazoline derivatives | |
| JPS649990B2 (enrdf_load_stackoverflow) | ||
| JPS635025B2 (enrdf_load_stackoverflow) | ||
| JP3252189B2 (ja) | ピラゾロ〔１，５−ａ〕ピリミジン誘導体 | |
| JPS6157307B2 (enrdf_load_stackoverflow) | ||
| JPS649991B2 (enrdf_load_stackoverflow) |