JPS574986A - Preparation of oxazolidine derivative - Google Patents
Preparation of oxazolidine derivativeInfo
- Publication number
- JPS574986A JPS574986A JP7912680A JP7912680A JPS574986A JP S574986 A JPS574986 A JP S574986A JP 7912680 A JP7912680 A JP 7912680A JP 7912680 A JP7912680 A JP 7912680A JP S574986 A JPS574986 A JP S574986A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- alkyl
- derivative
- useful
- 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
- 150000002917 oxazolidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 abstract 1
- QIORDSKCCHRSSD-UHFFFAOYSA-N 3-methyl-2-nitrophenol Chemical class CC1=CC=CC(O)=C1[N+]([O-])=O QIORDSKCCHRSSD-UHFFFAOYSA-N 0.000 abstract 1
- 206010003658 Atrial Fibrillation Diseases 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 abstract 1
- 206010003119 arrhythmia Diseases 0.000 abstract 1
- 230000006793 arrhythmia Effects 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- -1 e.g. Substances 0.000 abstract 1
- 150000003948 formamides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 230000001537 neural effect Effects 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 235000011150 stannous chloride Nutrition 0.000 abstract 1
- 239000001119 stannous chloride Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
PURPOSE: To obtain the titled compound in high yield useful as an intermediate for synthesizing drugs, by reacting a methylnitrophenol derivative of oxazolidine with a substituted formamide derivative, followed by reduction.
CONSTITUTION: A compound shown by the formula I (R is alkyl) is reacted with a compound shown by the formula II (X and Y are halogen; R1 is alkyl, aryl, or aralkyl) in a solvent, preferably hydrocarbon, ether, dimethylformamide, etc. in the presence of a base, e.g., triethylamine, etc. at 50W150°CC. The prepared reaction product is reduced with a reducing agent, e.g., stannous chloride, sodium boron hydride, etc. in the presence of a catalyst (e.g., platinum, palladium, nickel, etc.) to give the disired substance shown by the formula III. A compound obtained by hydrolyzing the desired compound has β-adrenergic neuronal blocking actions and is useful for remedying and preventing arrhythmia, atrial fibrillation, and coronatitis.
COPYRIGHT: (C)1982,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7912680A JPS574986A (en) | 1980-06-13 | 1980-06-13 | Preparation of oxazolidine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7912680A JPS574986A (en) | 1980-06-13 | 1980-06-13 | Preparation of oxazolidine derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS574986A true JPS574986A (en) | 1982-01-11 |
Family
ID=13681238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7912680A Pending JPS574986A (en) | 1980-06-13 | 1980-06-13 | Preparation of oxazolidine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS574986A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5399574A (en) * | 1990-06-07 | 1995-03-21 | Burroughs Wellcome Co. | Indolyl tetrahydropyridines for treating migraine |
-
1980
- 1980-06-13 JP JP7912680A patent/JPS574986A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5399574A (en) * | 1990-06-07 | 1995-03-21 | Burroughs Wellcome Co. | Indolyl tetrahydropyridines for treating migraine |
| US5466699A (en) * | 1990-06-07 | 1995-11-14 | Burroughs Wellcome Co. | Indolyl compounds for treating migraine |
| US5863935A (en) * | 1990-06-07 | 1999-01-26 | Zeneca Limited | Therapeutic heterocyclic compounds |
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