JPS56118081A - Preparation of 6-methoxy-1,8-naphthyridine - Google Patents
Preparation of 6-methoxy-1,8-naphthyridineInfo
- Publication number
- JPS56118081A JPS56118081A JP2144080A JP2144080A JPS56118081A JP S56118081 A JPS56118081 A JP S56118081A JP 2144080 A JP2144080 A JP 2144080A JP 2144080 A JP2144080 A JP 2144080A JP S56118081 A JPS56118081 A JP S56118081A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- naphthyridine
- lower alkyl
- methoxy
- 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
- IVQQSZQUIWLZIA-UHFFFAOYSA-N 3-methoxy-1,8-naphthyridine Chemical compound N1=CC=CC2=CC(OC)=CN=C21 IVQQSZQUIWLZIA-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 239000003814 drug Substances 0.000 abstract 2
- 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 2
- IRRYFLAZTLGICF-UHFFFAOYSA-N 5-ethyl-8-oxofuro[3,2-b][1,8]naphthyridine-7-carboxylic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC2=C1C=CO2 IRRYFLAZTLGICF-UHFFFAOYSA-N 0.000 abstract 1
- QUXLCYFNVNNRBE-UHFFFAOYSA-N 6-methylpyridin-2-amine Chemical compound CC1=CC=CC(N)=N1 QUXLCYFNVNNRBE-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
PURPOSE: To prepare the titled compound useful as an intermediate of medicine, at a low cost, by reacting an easily available compound as a raw material first with bromine and then with sodium methoxide.
CONSTITUTION: A compound of formula II (R1, R3' and R7 are lower alkyl) which is easily and industrially available compound, is made to react with bromine to obtain a compound of formula III, which is reacted with sodium methoxide to obtain a 1,7-dialkyl-6-methoxy-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid of formula I (R3 is H or lower alkyl) or its lower alkyl ester. The compound of formula II can be prepared easily from, e.g. 6-amino-2-picoline. The compound of formula I can be converted e.g. to 5-ethyl-5,8-dihydro-8-oxofuro[3,2-b]-1,8-naphthyridine-7-carboxylic acid which is a known medicine.
COPYRIGHT: (C)1981,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2144080A JPS56118081A (en) | 1980-02-22 | 1980-02-22 | Preparation of 6-methoxy-1,8-naphthyridine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2144080A JPS56118081A (en) | 1980-02-22 | 1980-02-22 | Preparation of 6-methoxy-1,8-naphthyridine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS56118081A true JPS56118081A (en) | 1981-09-16 |
Family
ID=12055018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2144080A Pending JPS56118081A (en) | 1980-02-22 | 1980-02-22 | Preparation of 6-methoxy-1,8-naphthyridine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56118081A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008046135A1 (en) * | 2006-10-16 | 2008-04-24 | Bionomics Limited | Novel anxiolytic compounds |
| US9023848B2 (en) | 2011-03-02 | 2015-05-05 | Bionomics Limited | Small-molecules as therapeutics |
| US9133188B2 (en) | 2011-05-12 | 2015-09-15 | Bionomics Limited | Methods for preparing naphthyridines |
| US10954231B2 (en) | 2006-10-16 | 2021-03-23 | Bionomics Limited | Anxiolytic compounds |
-
1980
- 1980-02-22 JP JP2144080A patent/JPS56118081A/en active Pending
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008046135A1 (en) * | 2006-10-16 | 2008-04-24 | Bionomics Limited | Novel anxiolytic compounds |
| US8293737B2 (en) | 2006-10-16 | 2012-10-23 | Bionomics Limited | Anxiolytic compounds |
| US8551990B2 (en) | 2006-10-16 | 2013-10-08 | Bionomics Limited | Anxiolytic compounds |
| US8614212B2 (en) | 2006-10-16 | 2013-12-24 | Bionomics Limited | Anxiolytic compounds |
| US8906912B2 (en) | 2006-10-16 | 2014-12-09 | Bionomics Limited | Anxiolytic compounds |
| US9573945B2 (en) | 2006-10-16 | 2017-02-21 | Bionomics Limited | Anxiolytic compounds |
| JP2017105818A (en) * | 2006-10-16 | 2017-06-15 | バイオノミクス リミテッド | Novel anxiolytic compounds |
| US9975892B2 (en) | 2006-10-16 | 2018-05-22 | Bionomics Limited | Anxiolytic compounds |
| US10233181B2 (en) | 2006-10-16 | 2019-03-19 | Bionomics Limited | Anxiolytic compounds |
| US10954231B2 (en) | 2006-10-16 | 2021-03-23 | Bionomics Limited | Anxiolytic compounds |
| US9023848B2 (en) | 2011-03-02 | 2015-05-05 | Bionomics Limited | Small-molecules as therapeutics |
| US9133188B2 (en) | 2011-05-12 | 2015-09-15 | Bionomics Limited | Methods for preparing naphthyridines |
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