IE38797B1 - Process for the preparation of tetracyclines - Google Patents
Process for the preparation of tetracyclinesInfo
- Publication number
- IE38797B1 IE38797B1 IE159/74A IE15974A IE38797B1 IE 38797 B1 IE38797 B1 IE 38797B1 IE 159/74 A IE159/74 A IE 159/74A IE 15974 A IE15974 A IE 15974A IE 38797 B1 IE38797 B1 IE 38797B1
- Authority
- IE
- Ireland
- Prior art keywords
- catalyst
- tetracycline
- alkyl
- tetracyclines
- preparation
- Prior art date
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
Landscapes
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
6-Methylenetetracyclines are hydrogenated by treating a tetracycline with an exocyclic methylene group with H2 in the presence of a catalyst consisting of a complex of rhodium with a tertiary phosphine of formula PR1R2R3, (where R1 and R2 are phenyl opt. substd. by e.g. alkyl, alkoxy, halogen or dialkylamino gps; and R3 and R gamma are alkyl or benzyl gp), in a solvent which dissolves both the tetracycline and the catalyst. The process produces little or no undesired anhydrotetracyclines, the reduction is practically quantitative and the catalyst is stereoselective to the production of the 6 alpha-epimer.
[FR2216268A1]
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US32851473A | 1973-02-01 | 1973-02-01 | |
US36806073A | 1973-06-08 | 1973-06-08 | |
US42827873A | 1973-12-26 | 1973-12-26 |
Publications (2)
Publication Number | Publication Date |
---|---|
IE38797L IE38797L (en) | 1974-08-01 |
IE38797B1 true IE38797B1 (en) | 1978-06-07 |
Family
ID=27406609
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IE159/74A IE38797B1 (en) | 1973-02-01 | 1974-01-28 | Process for the preparation of tetracyclines |
Country Status (18)
Country | Link |
---|---|
JP (1) | JPS5912111B2 (en) |
AR (1) | AR210453A1 (en) |
CA (1) | CA1027117A (en) |
CH (1) | CH589605A5 (en) |
DD (1) | DD110855A5 (en) |
DE (1) | DE2403714A1 (en) |
ES (1) | ES422758A1 (en) |
FI (1) | FI58492C (en) |
FR (1) | FR2216268A1 (en) |
IE (1) | IE38797B1 (en) |
IL (1) | IL44084A (en) |
IN (1) | IN138662B (en) |
LU (1) | LU69288A1 (en) |
NL (1) | NL166921B (en) |
NO (2) | NO151585C (en) |
PH (1) | PH14446A (en) |
SE (1) | SE435619C (en) |
YU (1) | YU39915B (en) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AR208347A1 (en) * | 1974-12-19 | 1976-12-20 | Pfizer | IMPROVEMENT IN THE PRODUCTION OF ALPHA-6-DEOXYTETRACYCLINES |
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 | |
USRE32535E (en) * | 1982-01-19 | 1987-10-27 | Plurichemie Anstalt | Process for the preparation of α-6-deoxytetracyclines |
US4550096A (en) * | 1982-01-19 | 1985-10-29 | Plurichemie Anstalt | Homogeneous catalytic system comprising rhodium, hydrazine and phosphine and a process for the preparation of same |
DK386784A (en) * | 1983-08-17 | 1985-02-18 | Hovione Int Ltd | PROCEDURE FOR PREPARING ALFA-6-DESOXY-TETRACYCLINES |
US4987242A (en) * | 1988-10-28 | 1991-01-22 | Jagmohan Khanna | Hydrogenation catalyst useful in the production of alpha-6-deoxytetracyclines |
US4973719A (en) * | 1988-10-28 | 1990-11-27 | Ranbaxy Laboratories Limited | Process for the production of alpha-6-deoxytetracyclines |
US5049683A (en) * | 1989-01-04 | 1991-09-17 | Houba, Inc. | Process for the production of alpha-6-deoxytetracyclines |
DE68900339D1 (en) * | 1989-04-03 | 1991-11-21 | Ranbaxy Lab Ltd | METHOD FOR PRODUCING ALPHA-6-DEOXYTETRACYCLINES. |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3639439A (en) * | 1964-12-10 | 1972-02-01 | Shell Oil Co | Rhodium (i) halide complexes |
US3489786A (en) * | 1964-12-10 | 1970-01-13 | Shell Oil Co | Hydrogenation process |
GB1121643A (en) * | 1966-02-07 | 1968-07-31 | Ici Ltd | Hydrogenation process |
GB1418137A (en) * | 1972-02-24 | 1975-12-17 | Ankerfarm Spa | Process for the preparation of alpha-6-deoxytetracyclines |
AR208347A1 (en) * | 1974-12-19 | 1976-12-20 | Pfizer | IMPROVEMENT IN THE PRODUCTION OF ALPHA-6-DEOXYTETRACYCLINES |
-
1974
- 1974-01-23 SE SE7400879A patent/SE435619C/en not_active IP Right Cessation
- 1974-01-25 IL IL44084A patent/IL44084A/en unknown
- 1974-01-25 IN IN171/CAL/74A patent/IN138662B/en unknown
- 1974-01-26 DE DE2403714A patent/DE2403714A1/en active Granted
- 1974-01-28 IE IE159/74A patent/IE38797B1/en unknown
- 1974-01-28 PH PH15444A patent/PH14446A/en unknown
- 1974-01-29 CA CA191,157A patent/CA1027117A/en not_active Expired
- 1974-01-30 ES ES422758A patent/ES422758A1/en not_active Expired
- 1974-01-30 LU LU69288A patent/LU69288A1/xx unknown
- 1974-01-31 DD DD176299A patent/DD110855A5/xx unknown
- 1974-01-31 FI FI266/74A patent/FI58492C/en active
- 1974-01-31 NL NL7401340.A patent/NL166921B/en not_active Application Discontinuation
- 1974-01-31 NO NO740320A patent/NO151585C/en unknown
- 1974-02-01 JP JP49012873A patent/JPS5912111B2/en not_active Expired
- 1974-02-01 CH CH143574A patent/CH589605A5/xx not_active IP Right Cessation
- 1974-02-01 FR FR7403435A patent/FR2216268A1/en active Granted
- 1974-02-01 YU YU253/74A patent/YU39915B/en unknown
- 1974-02-10 AR AR252162A patent/AR210453A1/en active
-
1984
- 1984-09-24 NO NO843825A patent/NO153806C/en unknown
Also Published As
Publication number | Publication date |
---|---|
NO843825L (en) | 1974-08-02 |
SE7400879L (en) | 1974-09-12 |
AU6490674A (en) | 1975-07-31 |
PH14446A (en) | 1981-07-22 |
SE435619B (en) | 1984-10-08 |
JPS49102662A (en) | 1974-09-27 |
DD110855A5 (en) | 1975-01-12 |
CA1027117A (en) | 1978-02-28 |
IN138662B (en) | 1976-03-06 |
NO740320L (en) | 1974-08-02 |
IL44084A (en) | 1977-10-31 |
FI58492B (en) | 1980-10-31 |
NO151585C (en) | 1985-05-08 |
NO153806B (en) | 1986-02-17 |
YU39915B (en) | 1985-06-30 |
SE435619C (en) | 1985-11-18 |
YU25374A (en) | 1982-02-28 |
FR2216268A1 (en) | 1974-08-30 |
CH589605A5 (en) | 1977-07-15 |
NO153806C (en) | 1986-05-28 |
IE38797L (en) | 1974-08-01 |
DE2403714A1 (en) | 1974-08-22 |
ES422758A1 (en) | 1976-08-01 |
IL44084A0 (en) | 1974-05-16 |
AR210453A1 (en) | 1977-08-15 |
FR2216268B1 (en) | 1978-01-06 |
JPS5912111B2 (en) | 1984-03-21 |
DE2403714C2 (en) | 1987-04-09 |
NO151585B (en) | 1985-01-21 |
NL166921B (en) | 1981-05-15 |
FI58492C (en) | 1986-09-05 |
LU69288A1 (en) | 1974-09-25 |
NL7401340A (en) | 1974-08-05 |
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