JPS617238A - ｄｌ−クロルプレナリンの光学分割法 - Google Patents
ｄｌ−クロルプレナリンの光学分割法Info
- Publication number
- JPS617238A JPS617238A JP12817184A JP12817184A JPS617238A JP S617238 A JPS617238 A JP S617238A JP 12817184 A JP12817184 A JP 12817184A JP 12817184 A JP12817184 A JP 12817184A JP S617238 A JPS617238 A JP S617238A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- chlorprenaline
- water
- optical resolution
- crystals
- 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
- 230000003287 optical effect Effects 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 12
- 229950011462 clorprenaline Drugs 0.000 title abstract 3
- 239000013078 crystal Substances 0.000 claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000002253 acid Substances 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 7
- 150000007524 organic acids Chemical class 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims description 3
- SSMSBSWKLKKXGG-LLVKDONJSA-N (S)-clorprenaline Chemical compound CC(C)NC[C@@H](O)C1=CC=CC=C1Cl SSMSBSWKLKKXGG-LLVKDONJSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 6
- -1 organic acid salt Chemical class 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 230000000254 damaging effect Effects 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- 239000002585 base Substances 0.000 description 11
- 238000004448 titration Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960001270 d- tartaric acid Drugs 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 150000004683 dihydrates Chemical class 0.000 description 2
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000004684 trihydrates Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 101100480530 Danio rerio tal1 gene Proteins 0.000 description 1
- 101100480538 Mus musculus Tal1 gene Proteins 0.000 description 1
- 101100312945 Pasteurella multocida (strain Pm70) talA gene Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004044 bronchoconstricting agent Substances 0.000 description 1
- 230000003435 bronchoconstrictive effect Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 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
- 239000000203 mixture Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12817184A JPS617238A (ja) | 1984-06-21 | 1984-06-21 | ｄｌ−クロルプレナリンの光学分割法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12817184A JPS617238A (ja) | 1984-06-21 | 1984-06-21 | ｄｌ−クロルプレナリンの光学分割法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS617238A true JPS617238A (ja) | 1986-01-13 |
| JPS6121939B2 JPS6121939B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-05-29 |
Family
ID=14978157
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12817184A Granted JPS617238A (ja) | 1984-06-21 | 1984-06-21 | ｄｌ−クロルプレナリンの光学分割法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS617238A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1384711A1 (en) * | 1996-06-13 | 2004-01-28 | SUMIKA FINE CHEMICALS Co., Ltd. | Optical resolution of a piperidine derivative |
| WO2008015689A1 (en) * | 2006-08-02 | 2008-02-07 | Aarti Healthcare Limited | A process for the preparation of optically pure r (-) salbutamol and its pharmaceutically acceptable salts |
| CN106045865A (zh) * | 2016-05-25 | 2016-10-26 | 陕西科技大学 | 一种基于手性液相色谱制备氯丙那林光学异构体的方法 |
-
1984
- 1984-06-21 JP JP12817184A patent/JPS617238A/ja active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1384711A1 (en) * | 1996-06-13 | 2004-01-28 | SUMIKA FINE CHEMICALS Co., Ltd. | Optical resolution of a piperidine derivative |
| US6815548B2 (en) | 1996-06-13 | 2004-11-09 | Sumika Fine Chemicals Co., Ltd. | Process for preparing a piperidine derivative |
| WO2008015689A1 (en) * | 2006-08-02 | 2008-02-07 | Aarti Healthcare Limited | A process for the preparation of optically pure r (-) salbutamol and its pharmaceutically acceptable salts |
| CN106045865A (zh) * | 2016-05-25 | 2016-10-26 | 陕西科技大学 | 一种基于手性液相色谱制备氯丙那林光学异构体的方法 |
| CN106045865B (zh) * | 2016-05-25 | 2018-11-27 | 陕西科技大学 | 一种基于手性液相色谱制备氯丙那林光学异构体的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6121939B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-05-29 |
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