GB1386662A - Preparation of 6-demethyl-6-deoxy-6-methylene-11alpha-bromo- tetracyclines and 9-bromo-anhydrotetracyclines - Google Patents
Preparation of 6-demethyl-6-deoxy-6-methylene-11alpha-bromo- tetracyclines and 9-bromo-anhydrotetracyclinesInfo
- Publication number
- GB1386662A GB1386662A GB1568872A GB1568872A GB1386662A GB 1386662 A GB1386662 A GB 1386662A GB 1568872 A GB1568872 A GB 1568872A GB 1568872 A GB1568872 A GB 1568872A GB 1386662 A GB1386662 A GB 1386662A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bromo
- tetracycline
- demethyl
- deoxy
- methylene
- 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.)
- Expired
Links
- 239000004098 Tetracycline Substances 0.000 title abstract 4
- 235000019364 tetracycline Nutrition 0.000 title abstract 3
- 229940040944 tetracyclines Drugs 0.000 title abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 4
- 239000001117 sulphuric acid Substances 0.000 abstract 4
- 235000011149 sulphuric acid Nutrition 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 229960002180 tetracycline Drugs 0.000 abstract 2
- 229930101283 tetracycline Natural products 0.000 abstract 2
- 150000003522 tetracyclines Chemical class 0.000 abstract 2
- LJVDOBHBFMLPMI-XRNKAMNCSA-N (4s,4as,5as,6s,12ar)-7-bromo-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical class C1=CC(Br)=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O LJVDOBHBFMLPMI-XRNKAMNCSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004100 Oxytetracycline Substances 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- QZIQJVCYUQZDIR-UHFFFAOYSA-N mechlorethamine hydrochloride Chemical compound Cl.ClCCN(C)CCCl QZIQJVCYUQZDIR-UHFFFAOYSA-N 0.000 abstract 1
- 229960000625 oxytetracycline Drugs 0.000 abstract 1
- IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 abstract 1
- 235000019366 oxytetracycline Nutrition 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1386662 Bromo-tetracycline derivatives PLIVA PHARMACEUTICAL & CHEMICAL WORKS 5 April 1972 [5 April 1971] 15688/72 Heading C2C 6 - Demethyl - 6 - deoxy - 6 - methylene - 11α-bromo-tetracyclines (III) and 9-bromo-anhydrotetracyclines (IV) are prepared according to the following reaction sequence, wherein R represents -H or -OH In the reaction sequence, tetracycline (I, R = H) or oxytetracycline (I, R = OH) is reacted with bromine in the presence of pyridine or morpholine to give an 11a-bromo-tetracycline- 6,12-hemiketal (II). The latter is then dehydrated with either a mixture of sulphuric acid and acetonitrile resulting in the 6-demethyl-6- deoxy - 6 - methylene - 11a - bromo - tetracycline (III), or a mixture of sulphuric acid and glacial acetic acid resulting in the 9-bromoanhydrotetracycline (IV). When sulphuric acid alone or containing 30% water is used, a mixture of (III) and (IV) are obtained, the proportion of the anhydro-derivative IV increasing with the concentration of the sulphuric acid. In a comparative example, tetracycline is brominated to 11a-bromotetracycline-6,12-hemiketal with N-bromosuccinimide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU82971A YU36486B (en) | 1971-04-05 | 1971-04-05 | Process for preparing 6-demethyl-6-deoxy-6-methylene-11a-bromo tetracycline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1386662A true GB1386662A (en) | 1975-03-12 |
Family
ID=25551600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1568872A Expired GB1386662A (en) | 1971-04-05 | 1972-04-05 | Preparation of 6-demethyl-6-deoxy-6-methylene-11alpha-bromo- tetracyclines and 9-bromo-anhydrotetracyclines |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT314732B (en) |
| DE (1) | DE2216459A1 (en) |
| ES (1) | ES401253A1 (en) |
| GB (1) | GB1386662A (en) |
| YU (1) | YU36486B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107056641B (en) * | 2017-04-10 | 2019-05-17 | 河南师范大学 | A kind of preparation method of fortimicin |
| CN107098825B (en) * | 2017-04-10 | 2019-05-31 | 广东中农联生物制药有限公司 | A kind of high efficiency preparation method of fortimicin |
-
1971
- 1971-04-05 YU YU82971A patent/YU36486B/en unknown
-
1972
- 1972-03-22 AT AT244172A patent/AT314732B/en not_active IP Right Cessation
- 1972-03-28 ES ES401253A patent/ES401253A1/en not_active Expired
- 1972-04-05 GB GB1568872A patent/GB1386662A/en not_active Expired
- 1972-04-05 DE DE19722216459 patent/DE2216459A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| YU82971A (en) | 1982-02-25 |
| YU36486B (en) | 1984-02-29 |
| DE2216459A1 (en) | 1972-10-12 |
| AT314732B (en) | 1974-04-25 |
| ES401253A1 (en) | 1975-02-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) |