PL100701B1 - - Google Patents
Download PDFInfo
- Publication number
- PL100701B1 PL100701B1 PL18375775A PL18375775A PL100701B1 PL 100701 B1 PL100701 B1 PL 100701B1 PL 18375775 A PL18375775 A PL 18375775A PL 18375775 A PL18375775 A PL 18375775A PL 100701 B1 PL100701 B1 PL 100701B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- acid
- hydroxy
- methyl
- hydrochloride
- Prior art date
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- -1 3-methyl-6-hydroxy-7-acetylcoumaronic acid aminoester hydrochlorides Chemical class 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000003840 hydrochlorides Chemical class 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- 230000001077 hypotensive effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 208000001953 Hypotension Diseases 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000000812 cholinergic antagonist Substances 0.000 description 2
- 150000001907 coumarones Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 208000021822 hypotensive Diseases 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000002048 spasmolytic effect Effects 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- OXIKLRTYAYRAOE-CMDGGOBGSA-N (e)-3-(1-benzyl-3-pyridin-3-ylpyrazol-4-yl)prop-2-enoic acid Chemical compound N1=C(C=2C=NC=CC=2)C(/C=C/C(=O)O)=CN1CC1=CC=CC=C1 OXIKLRTYAYRAOE-CMDGGOBGSA-N 0.000 description 1
- OFFSPAZVIVZPHU-UHFFFAOYSA-N 1-benzofuran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)=CC2=C1 OFFSPAZVIVZPHU-UHFFFAOYSA-N 0.000 description 1
- LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 description 1
- AQMCATUUSZRBCB-UHFFFAOYSA-N 7-acetyl-6-hydroxy-3-methyl-1-benzofuran-2-carboxylic acid Chemical compound CC(=O)C1=C(O)C=CC2=C1OC(C(O)=O)=C2C AQMCATUUSZRBCB-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL18375775A PL100701B1 (enExample) | 1975-10-03 | 1975-10-03 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL18375775A PL100701B1 (enExample) | 1975-10-03 | 1975-10-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL100701B1 true PL100701B1 (enExample) | 1978-11-30 |
Family
ID=19973760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL18375775A PL100701B1 (enExample) | 1975-10-03 | 1975-10-03 |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL100701B1 (enExample) |
-
1975
- 1975-10-03 PL PL18375775A patent/PL100701B1/pl unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU629595B2 (en) | Pyrimidines and their pharmaceutical acceptable salts thereof, and their use as medicines | |
| DK175205B1 (da) | Fremgangsmåde til fremstilling af 1-adamantan-derivater | |
| KR920000270B1 (ko) | 치환된 벤즈 아미드의 제조방법 | |
| EP3851433B1 (en) | Preparation process for amantadine nitrate derivative | |
| NO163619B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive tetrahydro- 2-heterocykloalkylpyrido(4,3)indoler. | |
| US4129656A (en) | Thiazolidine derivatives, salidiuretic compositions and methods of effecting salidiuresis employing them | |
| CN118251384A (zh) | 苯并噻唑类化合物、其制备方法及应用 | |
| US3953490A (en) | Preparation of (3-trifluoromethylphenoxy)(4-chlorophenyl)acetonitrile | |
| PL100701B1 (enExample) | ||
| US2857383A (en) | Amino esters of thianaphthenealkanoic acids | |
| US2822391A (en) | Conhj | |
| CH627175A5 (enExample) | ||
| US5055490A (en) | Stereoisomers of benzonitrile derivatives, useful as cardiac arrhythmiac agents | |
| KR920000375B1 (ko) | 치환된 구아닐티오우레아의 제조방법 | |
| US2910505A (en) | S-substituted n-benzhydryl pseudothioureas and their pseudothiouronium salts | |
| DE69528770T2 (de) | Derivate des benzopyrans und des benzothiopyrans, deren herstellung und deren verwendung als agonisten von dopamin rezeptoren | |
| ITMI20011772A1 (it) | Processo per la preparazione della 2,5-bis-(2,2,2-trifluoroetossi)-n-(2-piperidilmetil)-benzamide(flecainide) | |
| JPS63203672A (ja) | 新規な複素環化合物 | |
| JPS61267542A (ja) | アミノベンズアミド化合物 | |
| KR820001081B1 (ko) | 모라노린 유도체의 제법 | |
| US3004976A (en) | Aromatic carboxylic acid esters of | |
| CS255890B2 (en) | Process for preparing new racemic and optical active derivatives of 9-or 11-nitroapovincaminic acid | |
| KR820001082B1 (ko) | 모라노린 유도체의 제조방법 | |
| KR870000450B1 (ko) | 아미노 알킬 푸란 유도체의 제조방법 | |
| JPH0219356A (ja) | アミノアセトニトリル誘導体及びその製造方法 |