FR2216268A1 - Catalytic hydrogenation of 6-methylenetetracyclines - using rhodium-tert phosphine complex catalyst giving a stereospecific prod. in high yield - Google Patents
Catalytic hydrogenation of 6-methylenetetracyclines - using rhodium-tert phosphine complex catalyst giving a stereospecific prod. in high yieldInfo
- Publication number
- FR2216268A1 FR2216268A1 FR7403435A FR7403435A FR2216268A1 FR 2216268 A1 FR2216268 A1 FR 2216268A1 FR 7403435 A FR7403435 A FR 7403435A FR 7403435 A FR7403435 A FR 7403435A FR 2216268 A1 FR2216268 A1 FR 2216268A1
- Authority
- FR
- France
- Prior art keywords
- methylenetetracyclines
- rhodium
- stereospecific
- prod
- high yield
- 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.)
- Granted
Links
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 title abstract 4
- 239000003054 catalyst Substances 0.000 title abstract 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 title abstract 2
- 230000000707 stereoselective effect Effects 0.000 title abstract 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title 1
- 239000004098 Tetracycline Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229960002180 tetracycline Drugs 0.000 abstract 2
- 229930101283 tetracycline Natural products 0.000 abstract 2
- 235000019364 tetracycline Nutrition 0.000 abstract 2
- 150000003522 tetracyclines Chemical class 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 239000002904 solvent Substances 0.000 abstract 1
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)
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 |
|---|---|
| FR2216268A1 true FR2216268A1 (en) | 1974-08-30 |
| FR2216268B1 FR2216268B1 (enrdf_load_stackoverflow) | 1978-01-06 |
Family
ID=27406609
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7403435A Granted FR2216268A1 (en) | 1973-02-01 | 1974-02-01 | Catalytic hydrogenation of 6-methylenetetracyclines - using rhodium-tert phosphine complex catalyst giving a stereospecific prod. in high yield |
Country Status (18)
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0086046A1 (en) * | 1982-01-19 | 1983-08-17 | Plurichemie Anstalt | A process for the preparation of alpha-6-DEOXYTETRACYCLINES |
| US4597904A (en) * | 1983-08-17 | 1986-07-01 | Hovione Inter Ltd. | Process for the preparation of α-6-deoxy-tetracyclines |
| USRE32535E (en) * | 1982-01-19 | 1987-10-27 | Plurichemie Anstalt | Process for the preparation of α-6-deoxytetracyclines |
| US4973719A (en) * | 1988-10-28 | 1990-11-27 | Ranbaxy Laboratories Limited | Process for the production of alpha-6-deoxytetracyclines |
| US4987242A (en) * | 1988-10-28 | 1991-01-22 | Jagmohan Khanna | Hydrogenation catalyst useful in the production of alpha-6-deoxytetracyclines |
| US4997959A (en) * | 1989-04-03 | 1991-03-05 | 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 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR208347A1 (es) * | 1974-12-19 | 1976-12-20 | Pfizer | Mejora en la produccion de alfa-6-deoxitetraciclinas |
| 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 |
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 |
| CH579531A5 (enrdf_load_stackoverflow) * | 1972-02-24 | 1976-09-15 | Ankerfarm Spa | |
| AR208347A1 (es) * | 1974-12-19 | 1976-12-20 | Pfizer | Mejora en la produccion de alfa-6-deoxitetraciclinas |
-
1974
- 1974-01-23 SE SE7400879A patent/SE435619C/xx not_active IP Right Cessation
- 1974-01-25 IN IN171/CAL/74A patent/IN138662B/en unknown
- 1974-01-25 IL IL44084A patent/IL44084A/en unknown
- 1974-01-26 DE DE2403714A patent/DE2403714C2/de not_active Expired
- 1974-01-28 PH PH15444A patent/PH14446A/en unknown
- 1974-01-28 IE IE159/74A patent/IE38797B1/xx unknown
- 1974-01-29 CA CA191,157A patent/CA1027117A/en not_active Expired
- 1974-01-30 ES ES422758A patent/ES422758A1/es not_active Expired
- 1974-01-30 LU LU69288A patent/LU69288A1/xx unknown
- 1974-01-31 NO NO740320A patent/NO151585C/no unknown
- 1974-01-31 DD DD176299A patent/DD110855A5/xx unknown
- 1974-01-31 NL NL7401340.A patent/NL166921B/xx not_active Application Discontinuation
- 1974-01-31 FI FI266/74A patent/FI58492C/fi active
- 1974-02-01 FR FR7403435A patent/FR2216268A1/fr active Granted
- 1974-02-01 YU YU253/74A patent/YU39915B/xx unknown
- 1974-02-01 JP JP49012873A patent/JPS5912111B2/ja not_active Expired
- 1974-02-01 CH CH143574A patent/CH589605A5/xx not_active IP Right Cessation
- 1974-02-10 AR AR252162A patent/AR210453A1/es active
-
1984
- 1984-09-24 NO NO843825A patent/NO153806C/no unknown
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0086046A1 (en) * | 1982-01-19 | 1983-08-17 | Plurichemie Anstalt | A process for the preparation of alpha-6-DEOXYTETRACYCLINES |
| FR2530490A1 (fr) * | 1982-01-19 | 1984-01-27 | Plurichemie Anstalt | Procede de preparation de nouveaux catalyseurs contenant du rhodium et leur application |
| US4500458A (en) * | 1982-01-19 | 1985-02-19 | Plurichemie Anstalt | Process for the preparation of α-6-deoxytetracyclines |
| USRE32535E (en) * | 1982-01-19 | 1987-10-27 | Plurichemie Anstalt | Process for the preparation of α-6-deoxytetracyclines |
| US4597904A (en) * | 1983-08-17 | 1986-07-01 | Hovione Inter Ltd. | Process for the preparation of α-6-deoxy-tetracyclines |
| US4973719A (en) * | 1988-10-28 | 1990-11-27 | Ranbaxy Laboratories Limited | Process for the production of alpha-6-deoxytetracyclines |
| US4987242A (en) * | 1988-10-28 | 1991-01-22 | Jagmohan Khanna | Hydrogenation catalyst useful in the production of alpha-6-deoxytetracyclines |
| US5049683A (en) * | 1989-01-04 | 1991-09-17 | Houba, Inc. | Process for the production of alpha-6-deoxytetracyclines |
| US4997959A (en) * | 1989-04-03 | 1991-03-05 | Ranbaxy Laboratories Limited | Process for the production of alpha-6-deoxytetracyclines |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CL | Concession to grant licences | ||
| CD | Change of name or company name | ||
| CC | Supplementary protection certificate (spc) laid open to the public (law of 25 june 1990) |
Free format text: 92C0359, 920601 |
|
| CB | Supplementary protection certificate (spc) granted (law of 25 june 1990) |
Free format text: 92C0359, 740201 |
|
| CL | Concession to grant licences | ||
| CL | Concession to grant licences |