JPS6425767A - Production of quinazoline derivative or salt thereof - Google Patents
Production of quinazoline derivative or salt thereofInfo
- Publication number
- JPS6425767A JPS6425767A JP63075623A JP7562388A JPS6425767A JP S6425767 A JPS6425767 A JP S6425767A JP 63075623 A JP63075623 A JP 63075623A JP 7562388 A JP7562388 A JP 7562388A JP S6425767 A JPS6425767 A JP S6425767A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- salt
- reacting
- formula
- synthetic intermediate
- 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
- 150000003839 salts Chemical class 0.000 title abstract 3
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 abstract 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 abstract 2
- 238000006884 silylation reaction Methods 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 238000006136 alcoholysis reaction Methods 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 238000005828 desilylation reaction Methods 0.000 abstract 1
- 206010012601 diabetes mellitus Diseases 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000002904 solvent 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
- 239000005051 trimethylchlorosilane Substances 0.000 abstract 1
- SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 abstract 1
Abstract
PURPOSE:To easily and safely obtain the titled compound useful as a synthetic intermediate for anti-inflammatory agent or a synthetic intermediate for a drug for the remedy of complications of diabetes, in high yield at a low cost, by reacting a specific compound with a silylation agent and then a compound such as ethyl bromoacetate. CONSTITUTION:The objective compound of formula III can be produced by (1) reacting a compound of formula I (R<1> is H or halogen) or its salt with a silylation agent [e.g. hexamethyldisilazane, trimethylchlorosilane or N,O-bis(trimethylsilyl)acetamide] in a solvent such as toluene usually under cooling or at room temperature, (2) reacting the product with a compound of formula II [R<2> is alkyl, lower alkenyl, lower aralkyl or R<3>-Z (R<3> is carboxyl; Z is lower alkylene); X is acid residue] or its salt and, as necessary, (3) desilylating the reaction product. The desilylation is carried out by hydrolysis, alcoholysis, etc.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63075623A JPS6425767A (en) | 1987-04-03 | 1988-03-28 | Production of quinazoline derivative or salt thereof |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8342687 | 1987-04-03 | ||
| JP63075623A JPS6425767A (en) | 1987-04-03 | 1988-03-28 | Production of quinazoline derivative or salt thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6425767A true JPS6425767A (en) | 1989-01-27 |
Family
ID=26416778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63075623A Pending JPS6425767A (en) | 1987-04-03 | 1988-03-28 | Production of quinazoline derivative or salt thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6425767A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0775697A1 (en) | 1995-11-14 | 1997-05-28 | Sumitomo Chemical Company, Limited | Process for producing 1-substituted tetrahydroquinazolindionen |
| US5795984A (en) * | 1995-12-26 | 1998-08-18 | Sumitomo Chemical Company Limited | Process for producing isatoic anhydrides |
| WO1998041514A1 (en) * | 1997-03-17 | 1998-09-24 | Fujisawa Pharmaceutical Co., Ltd. | Process for producing quinazoline derivatives |
| EP0878468A1 (en) * | 1997-05-13 | 1998-11-18 | Sumitomo Chemical Company, Limited | Process for producing 1-substituted tetrahydroquinazolines |
| EP0896961A1 (en) * | 1995-12-28 | 1999-02-17 | Fuji Chemical Industry Co., Ltd. | Process for the preparation of 3-dihalobenzyl-2,4-quinazolinedione derivatives |
| US5994542A (en) * | 1995-11-14 | 1999-11-30 | Sumitomo Chemical Company, Limited | Process for producing 1-substituted tetrahydroquinazolines |
| WO2000053584A1 (en) * | 1999-03-09 | 2000-09-14 | Fujisawa Pharmaceutical Co., Ltd. | Process for producing quinazoline derivative or salt thereof |
| WO2008107436A1 (en) * | 2007-03-06 | 2008-09-12 | Novartis Ag | Bicyclic organic compounds suitable for the treatment of inflammatory or allergic conditions |
-
1988
- 1988-03-28 JP JP63075623A patent/JPS6425767A/en active Pending
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0775697A1 (en) | 1995-11-14 | 1997-05-28 | Sumitomo Chemical Company, Limited | Process for producing 1-substituted tetrahydroquinazolindionen |
| US5756738A (en) * | 1995-11-14 | 1998-05-26 | Sumitomo Chemical Company, Limited | Process for producing 1-substituted tetrahydroquinazolines |
| US5994542A (en) * | 1995-11-14 | 1999-11-30 | Sumitomo Chemical Company, Limited | Process for producing 1-substituted tetrahydroquinazolines |
| US5795984A (en) * | 1995-12-26 | 1998-08-18 | Sumitomo Chemical Company Limited | Process for producing isatoic anhydrides |
| US5981749A (en) * | 1995-12-26 | 1999-11-09 | Sumitomo Chemical Company Limited | Process for producing isatoic anhydrides |
| US5973145A (en) * | 1995-12-26 | 1999-10-26 | Sumitomo Chemical Company, Limited | Process for producing isatoic anhydrides |
| EP0896961A4 (en) * | 1995-12-28 | 1999-04-07 | Fuji Chem Ind Co Ltd | Process for the preparation of 3-dihalobenzyl-2,4-quinazolinedione derivatives |
| EP0896961A1 (en) * | 1995-12-28 | 1999-02-17 | Fuji Chemical Industry Co., Ltd. | Process for the preparation of 3-dihalobenzyl-2,4-quinazolinedione derivatives |
| WO1998041514A1 (en) * | 1997-03-17 | 1998-09-24 | Fujisawa Pharmaceutical Co., Ltd. | Process for producing quinazoline derivatives |
| EP0878468A1 (en) * | 1997-05-13 | 1998-11-18 | Sumitomo Chemical Company, Limited | Process for producing 1-substituted tetrahydroquinazolines |
| WO2000053584A1 (en) * | 1999-03-09 | 2000-09-14 | Fujisawa Pharmaceutical Co., Ltd. | Process for producing quinazoline derivative or salt thereof |
| WO2008107436A1 (en) * | 2007-03-06 | 2008-09-12 | Novartis Ag | Bicyclic organic compounds suitable for the treatment of inflammatory or allergic conditions |
| JP2010520256A (en) * | 2007-03-06 | 2010-06-10 | ノバルティス アーゲー | Bicyclic organic compounds suitable for the treatment of inflammation or allergic symptoms |
| US8633211B2 (en) | 2007-03-06 | 2014-01-21 | Novartis Ag | Bicyclic organic compounds suitable for the treatment of inflammatory or allergic conditions |
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