JPS5622765A - Novel method of preparing pindolol - Google Patents
Novel method of preparing pindololInfo
- Publication number
- JPS5622765A JPS5622765A JP9882579A JP9882579A JPS5622765A JP S5622765 A JPS5622765 A JP S5622765A JP 9882579 A JP9882579 A JP 9882579A JP 9882579 A JP9882579 A JP 9882579A JP S5622765 A JPS5622765 A JP S5622765A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- pindolol
- produce
- condensing agent
- 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.)
- Pending
Links
- PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 title abstract 2
- 229960002508 pindolol Drugs 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 238000006482 condensation reaction Methods 0.000 abstract 2
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 abstract 1
- NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical class OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 abstract 1
- DWJWWWPFIONTMT-UHFFFAOYSA-N 5-(chloromethyl)-3-propan-2-yl-1,3-oxazolidin-2-one Chemical compound CC(C)N1CC(CCl)OC1=O DWJWWWPFIONTMT-UHFFFAOYSA-N 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 208000000418 Premature Cardiac Complexes Diseases 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 238000007086 side reaction Methods 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910001023 sodium amalgam Inorganic materials 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
Landscapes
- Indole Compounds (AREA)
Abstract
PURPOSE: A novel compound, 3-isopropyl-5-chloromethyl-2-oxazolidinone, and a 4-hydroxyindole derivative are subjected to condensation reaction under specific conditions and the product is hydrolyzed to produce the titled compound used as a remedy for extrasystole with advantage.
CONSTITUTION: The condensation reaction between a novel compound of formula I and another compound of formula II (R is H, alkali metal) is conducted in an anhydrous polar solvent such as dimethylformamide in an inert gas atmosphere in the presence of a condensing agent of metallic sodium such as sodium amalgam or sodium hydride, preferably at a temperature lower than 120°C on an oil bath to produce pindolol of formula III having β-acceptor blocking effect and hypotensive activity wherein the amounts of the starting materials are stoichiometric and side reactions do not occur. The compound of formula I is prepared, e.g., by condensation between epichlorohydrin and isopropyl isocyanate in the presence of a condensing agent.
COPYRIGHT: (C)1981,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9882579A JPS5622765A (en) | 1979-08-02 | 1979-08-02 | Novel method of preparing pindolol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9882579A JPS5622765A (en) | 1979-08-02 | 1979-08-02 | Novel method of preparing pindolol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5622765A true JPS5622765A (en) | 1981-03-03 |
Family
ID=14230065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9882579A Pending JPS5622765A (en) | 1979-08-02 | 1979-08-02 | Novel method of preparing pindolol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5622765A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS577465A (en) * | 1980-06-13 | 1982-01-14 | Paamakemu Asia:Kk | Preparation of indole derivative |
| JPS6399336A (en) * | 1987-09-09 | 1988-04-30 | Howa Mach Ltd | Bobbin-transporting apparatus in fine spinning winder |
-
1979
- 1979-08-02 JP JP9882579A patent/JPS5622765A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS577465A (en) * | 1980-06-13 | 1982-01-14 | Paamakemu Asia:Kk | Preparation of indole derivative |
| JPS6399336A (en) * | 1987-09-09 | 1988-04-30 | Howa Mach Ltd | Bobbin-transporting apparatus in fine spinning winder |
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