JPS6429346A - Production of 7-nitro-6-demethyl-6-deoxytetracycline - Google Patents
Production of 7-nitro-6-demethyl-6-deoxytetracyclineInfo
- Publication number
- JPS6429346A JPS6429346A JP18344087A JP18344087A JPS6429346A JP S6429346 A JPS6429346 A JP S6429346A JP 18344087 A JP18344087 A JP 18344087A JP 18344087 A JP18344087 A JP 18344087A JP S6429346 A JPS6429346 A JP S6429346A
- Authority
- JP
- Japan
- Prior art keywords
- deoxytetracycline
- demethyl
- nitro
- production
- trifluoromethanesulfonic acid
- 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
- ICIDIYCNVITODC-UVPAEMEASA-N (4s,4as,5ar,12ar)-2-carbamoyl-4-(dimethylazaniumyl)-10,11,12a-trihydroxy-7-nitro-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracen-1-olate Chemical compound C1C2=C([N+]([O-])=O)C=CC(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O ICIDIYCNVITODC-UVPAEMEASA-N 0.000 title 1
- MTCQOMXDZUULRV-ADOAZJKMSA-N (4s,4as,5ar,12ar)-4-(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=CC=CC(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O MTCQOMXDZUULRV-ADOAZJKMSA-N 0.000 abstract 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 abstract 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 2
- 229910001963 alkali metal nitrate Inorganic materials 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000000802 nitrating effect Effects 0.000 abstract 2
- 229910017604 nitric acid Inorganic materials 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 1
- 229940072172 tetracycline antibiotic Drugs 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PURPOSE:To obtain the titled compound useful as a synthetic intermediate for a tetracycline antibiotic substance in high selectivity, by nitrating 6- demethyl-6-deoxytetracycline in trifluoromethanesulfonic acid. CONSTITUTION:The objective compound is produced by nitrating 6-demethyl-6- deoxytetracycline in trifluoromethanesulfonic acid with nitric acid or an alkali metal nitrate at -10-+20 deg.C, preferably -5-+10 deg.C. The amount of the trifluoromethanesulfonic acid is 5-100pts.wt., preferably 10-50pts.wt. per 1pt.wt. of 6-demethyl-6-deoxytetracycline and that of nitric acid or alkali metal nitrate is 1.0-1.1mol. per 1mol. of the 6-demethyl-6-deoxytetracycline.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18344087A JPS6429346A (en) | 1987-07-24 | 1987-07-24 | Production of 7-nitro-6-demethyl-6-deoxytetracycline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18344087A JPS6429346A (en) | 1987-07-24 | 1987-07-24 | Production of 7-nitro-6-demethyl-6-deoxytetracycline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6429346A true JPS6429346A (en) | 1989-01-31 |
Family
ID=16135807
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18344087A Pending JPS6429346A (en) | 1987-07-24 | 1987-07-24 | Production of 7-nitro-6-demethyl-6-deoxytetracycline |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6429346A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004502753A (en) * | 2000-07-07 | 2004-01-29 | トラスティーズ・オブ・タフツ・カレッジ | 7-substituted tetracycline compounds |
| WO2007120913A3 (en) * | 2006-04-17 | 2007-12-06 | Teva Pharma | Isolation of tetracycline derivatives |
| US7871993B2 (en) | 2006-04-24 | 2011-01-18 | Teva Pharmaceutical Industries Ltd. | Tigecycline crystalline forms and processes for preparation thereof |
| US8198470B2 (en) | 2006-04-24 | 2012-06-12 | Teva Pharmaceutical Industries Ltd. | Crystalline form II of tigecycline and processes for preparation thereof |
| US8198469B2 (en) | 2006-11-29 | 2012-06-12 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of tigecycline and processes for preparation thereof |
-
1987
- 1987-07-24 JP JP18344087A patent/JPS6429346A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004502753A (en) * | 2000-07-07 | 2004-01-29 | トラスティーズ・オブ・タフツ・カレッジ | 7-substituted tetracycline compounds |
| WO2007120913A3 (en) * | 2006-04-17 | 2007-12-06 | Teva Pharma | Isolation of tetracycline derivatives |
| US7871993B2 (en) | 2006-04-24 | 2011-01-18 | Teva Pharmaceutical Industries Ltd. | Tigecycline crystalline forms and processes for preparation thereof |
| US8198470B2 (en) | 2006-04-24 | 2012-06-12 | Teva Pharmaceutical Industries Ltd. | Crystalline form II of tigecycline and processes for preparation thereof |
| US8207361B2 (en) | 2006-04-24 | 2012-06-26 | Teva Pharmaceutical Industries Ltd. | Tigecycline crystalline forms and processes for preparation thereof |
| US8198469B2 (en) | 2006-11-29 | 2012-06-12 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of tigecycline and processes for preparation thereof |
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