GB1296340A - - Google Patents
Info
- Publication number
- GB1296340A GB1296340A GB1296340DA GB1296340A GB 1296340 A GB1296340 A GB 1296340A GB 1296340D A GB1296340D A GB 1296340DA GB 1296340 A GB1296340 A GB 1296340A
- Authority
- GB
- United Kingdom
- Prior art keywords
- salt
- deoxytetracycline
- methylene
- weight
- nickel
- 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
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 7
- 239000003054 catalyst Substances 0.000 abstract 6
- 150000003839 salts Chemical class 0.000 abstract 6
- 229910017052 cobalt Inorganic materials 0.000 abstract 4
- 239000010941 cobalt Substances 0.000 abstract 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 4
- 239000004098 Tetracycline Substances 0.000 abstract 3
- 229910052759 nickel Inorganic materials 0.000 abstract 3
- 235000019364 tetracycline Nutrition 0.000 abstract 3
- 150000003522 tetracyclines Chemical class 0.000 abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- 229960002180 tetracycline Drugs 0.000 abstract 2
- 229930101283 tetracycline Natural products 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052684 Cerium Inorganic materials 0.000 abstract 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Chemical group 0.000 abstract 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 229910052804 chromium Inorganic materials 0.000 abstract 1
- 239000011651 chromium Substances 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052750 molybdenum Inorganic materials 0.000 abstract 1
- 239000011733 molybdenum Substances 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 229910052703 rhodium Inorganic materials 0.000 abstract 1
- 239000010948 rhodium Substances 0.000 abstract 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract 1
- 229940040944 tetracyclines Drugs 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1296340 Preparation of 6-deoxytetracyclines ALFA FARMACEUTICI SpA 12 Aug 1971 [24 Feb 1971] 37846/71 Heading C2A A process for preparing a 6-deoxytetracycline or a salt thereof comprises hydrogenating a corresponding 6 - methylene - 6 - deoxytetracycline or a salt thereof in the presence of a nickel or cobalt catalyst, followed by salification if required. Raney nickel and Ranoy cobalt are suitable catalysts. In particular, a process for preparing a 6-deoxytetracycline of Formula I or a salt thereof comprises hydrogenating a corresponding 6 - methylene - 6 - deoxytetracycline of Formula II or III wherein R is hydrogen or hydroxyl and X is chlorine or bromine or a salt thereof in the presence of a nickel or cobalt catalyst, followed by salification if required. An example of a tetracycline which may be prepared according to this process is 6-α-deoxy-5-hydroxytetra. cycline. Examples of tetracyclines which may be hydrogenated according to this process are 11 - α - chloro - 6 - deoxy - 6 - methylene- 5- hydroxy-tetracycline or 6-deoxy-6-methylene- 5-hydroxytetracycline or a salt thereof. The weight of catalyst employed may be 1% to 30% of the weight of the tetracycline to be hydrogenated. The hydrogenation may be carried out in the presence of a catalyst promoter, e.g. a hydrosoluble salt of copper, zinc, chromium, molybdenum, cerium, platinum, palladium or rhodium. The weight of the promoter may be from 0À01% to 5% of the weight of the nickel or cobalt catalyst used.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT335171 | 1971-02-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1296340A true GB1296340A (en) | 1972-11-15 |
Family
ID=11105485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1296340D Expired GB1296340A (en) | 1971-02-24 | 1971-08-12 |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT309679B (en) |
| BE (1) | BE770580A (en) |
| DE (1) | DE2136621A1 (en) |
| ES (1) | ES394776A1 (en) |
| FR (1) | FR2127491A5 (en) |
| GB (1) | GB1296340A (en) |
| NL (1) | NL7109740A (en) |
| ZA (1) | ZA714766B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5075470A (en) * | 1989-07-31 | 1991-12-24 | Plurichemie Anstalt | Process for the preparation of a rhodium complex |
| CN114315627A (en) * | 2021-12-30 | 2022-04-12 | 扬州联博药业有限公司 | Method for synthesizing doxycycline dehydrate by catalyzing with normal-temperature ionic liquid and zeolite |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU41093B (en) * | 1978-04-12 | 1986-12-31 | Pliva Pharm & Chem Works | Process for preparing 6-deoxy-5hydroxy-tetracycline |
| PT76061A (en) * | 1982-12-30 | 1983-01-01 | Stable homogeneous hydrogenation rhodium catalyst - useful in high yield prodn. of doxycycline by stereospecific hydrogenation | |
| US4500458A (en) * | 1982-01-19 | 1985-02-19 | Plurichemie Anstalt | Process for the preparation of α-6-deoxytetracyclines |
| DE391005T1 (en) * | 1989-04-03 | 1991-04-11 | Ranbaxy Laboratories, Ltd., New Delhi | METHOD FOR PRODUCING ALPHA-6-DEOXYTETRACYCLINES. |
-
1971
- 1971-07-14 NL NL7109740A patent/NL7109740A/xx unknown
- 1971-07-19 ZA ZA714766A patent/ZA714766B/en unknown
- 1971-07-22 DE DE19712136621 patent/DE2136621A1/en active Pending
- 1971-07-23 AT AT643671A patent/AT309679B/en not_active IP Right Cessation
- 1971-07-28 BE BE770580A patent/BE770580A/en unknown
- 1971-08-12 GB GB1296340D patent/GB1296340A/en not_active Expired
- 1971-09-03 ES ES394776A patent/ES394776A1/en not_active Expired
- 1971-09-20 FR FR7133735A patent/FR2127491A5/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5075470A (en) * | 1989-07-31 | 1991-12-24 | Plurichemie Anstalt | Process for the preparation of a rhodium complex |
| CN114315627A (en) * | 2021-12-30 | 2022-04-12 | 扬州联博药业有限公司 | Method for synthesizing doxycycline dehydrate by catalyzing with normal-temperature ionic liquid and zeolite |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7109740A (en) | 1972-08-28 |
| AT309679B (en) | 1973-08-27 |
| DE2136621A1 (en) | 1972-09-14 |
| ZA714766B (en) | 1972-09-27 |
| FR2127491A5 (en) | 1972-10-13 |
| BE770580A (en) | 1971-12-01 |
| ES394776A1 (en) | 1974-09-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 414F | Notice of opposition given (sect. 14/1949) | ||
| PS | Patent sealed | ||
| 414E | Application relinquished (sect. 14/1949) | ||
| CSNS | Application of which complete specification have been accepted and published, but patent is not sealed |