GB1477995A - Rhodium-containing catalyst and use thereof in preparation of 6-deoxy-5-oxytetracycline - Google Patents
Rhodium-containing catalyst and use thereof in preparation of 6-deoxy-5-oxytetracyclineInfo
- Publication number
- GB1477995A GB1477995A GB318476A GB318476A GB1477995A GB 1477995 A GB1477995 A GB 1477995A GB 318476 A GB318476 A GB 318476A GB 318476 A GB318476 A GB 318476A GB 1477995 A GB1477995 A GB 1477995A
- Authority
- GB
- United Kingdom
- Prior art keywords
- deoxy
- oxytetracycline
- catalyst
- rhodium
- reaction mixture
- 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
- 239000003054 catalyst Substances 0.000 title abstract 7
- 239000004100 Oxytetracycline Substances 0.000 title abstract 4
- 229960000625 oxytetracycline Drugs 0.000 title abstract 4
- 229910052703 rhodium Inorganic materials 0.000 title abstract 3
- 239000010948 rhodium Substances 0.000 title abstract 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 9
- 238000005984 hydrogenation reaction Methods 0.000 abstract 4
- 239000011541 reaction mixture Substances 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 2
- 229910021604 Rhodium(III) chloride Inorganic materials 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 230000004907 flux Effects 0.000 abstract 1
- 239000002198 insoluble material Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- MHIGBKBJSQVXNH-IWVLMIASSA-N methacycline Chemical compound C=C([C@H]1[C@@H]2O)C3=CC=CC(O)=C3C(=O)C1=C(O)[C@@]1(O)[C@@H]2[C@H](N(C)C)C(O)=C(C(N)=O)C1=O MHIGBKBJSQVXNH-IWVLMIASSA-N 0.000 abstract 1
- 235000019366 oxytetracycline Nutrition 0.000 abstract 1
- 229960004368 oxytetracycline hydrochloride Drugs 0.000 abstract 1
- 238000011084 recovery Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 239000001632 sodium acetate 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
- 150000004684 trihydrates Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
-
- 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
-
- 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
-
- 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
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
- B01J31/30—Halides
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)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/544,839 US3962131A (en) | 1975-01-28 | 1975-01-28 | Rhodium containing catalyst and use thereof in preparation of 6-deoxy-5-oxytetracycline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1477995A true GB1477995A (en) | 1977-06-29 |
Family
ID=24173812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB318476A Expired GB1477995A (en) | 1975-01-28 | 1976-01-27 | Rhodium-containing catalyst and use thereof in preparation of 6-deoxy-5-oxytetracycline |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3962131A (enExample) |
| JP (1) | JPS5724177B2 (enExample) |
| AR (1) | AR211112A1 (enExample) |
| BE (1) | BE837665A (enExample) |
| CA (1) | CA1035352A (enExample) |
| CH (1) | CH609887A5 (enExample) |
| DE (1) | DE2554524C3 (enExample) |
| DK (1) | DK151381C (enExample) |
| ES (1) | ES444143A1 (enExample) |
| FR (1) | FR2299079A1 (enExample) |
| GB (1) | GB1477995A (enExample) |
| HK (1) | HK31079A (enExample) |
| IE (1) | IE41936B1 (enExample) |
| KE (1) | KE2941A (enExample) |
| LU (1) | LU74230A1 (enExample) |
| MX (1) | MX4844E (enExample) |
| MY (1) | MY7900248A (enExample) |
| NL (1) | NL159598B (enExample) |
| SE (1) | SE428534B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111732522A (zh) * | 2020-07-21 | 2020-10-02 | 山东国邦药业有限公司 | 一种脱氧土霉素的制备方法 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4743699A (en) * | 1982-01-19 | 1988-05-10 | Plurichemie Anstalt | Homogeneous catalytic system and a process for the preparation of same |
| PT76061A (en) * | 1982-12-30 | 1983-01-01 | Stable homogeneous hydrogenation rhodium catalyst - useful in high yield prodn. of doxycycline by stereospecific hydrogenation | |
| 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 |
| JPS5967358U (ja) * | 1982-10-29 | 1984-05-07 | 三菱自動車工業株式会社 | 車両の配管取付構造 |
| DK386784A (da) * | 1983-08-17 | 1985-02-18 | Hovione Int Ltd | Fremgangsmaade til fremstilling af alfa-6-desoxy-tetracykliner |
| US4987242A (en) * | 1988-10-28 | 1991-01-22 | Jagmohan Khanna | Hydrogenation catalyst useful in the production of alpha-6-deoxytetracyclines |
| US4902447A (en) * | 1988-10-28 | 1990-02-20 | Ranbaxy Laboratories Limited | Process for the production of alpha-6-deoxytetracyclines and hydrogenation catalyst useful therein |
| 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 |
| ATE68476T1 (de) * | 1989-04-03 | 1991-11-15 | Ranbaxy Lab Ltd | Verfahren zur herstellung von alpha-6deoxytetracyclinen. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3759838A (en) * | 1964-12-10 | 1973-09-18 | Shell Oil Co | Rhodium halide complex catalyst compositions |
| US3660493A (en) * | 1967-10-17 | 1972-05-02 | British Petroleum Co | Hydroformylation process |
| GB1326012A (en) * | 1969-07-14 | 1973-08-08 | Johnson Matthey Co Ltd | Catalyst compositions |
| US3907890A (en) * | 1974-05-28 | 1975-09-23 | Pfizer | Preparation of alpha-6-deoxy-5-hydroxytetracycline |
-
1975
- 1975-01-28 US US05/544,839 patent/US3962131A/en not_active Expired - Lifetime
- 1975-11-17 IE IE2495/75A patent/IE41936B1/en unknown
- 1975-12-04 DE DE2554524A patent/DE2554524C3/de not_active Expired
- 1975-12-18 CA CA242,009A patent/CA1035352A/en not_active Expired
-
1976
- 1976-01-06 MX MX766633U patent/MX4844E/es unknown
- 1976-01-08 ES ES444143A patent/ES444143A1/es not_active Expired
- 1976-01-14 NL NL7600334.A patent/NL159598B/xx not_active IP Right Cessation
- 1976-01-16 FR FR7601164A patent/FR2299079A1/fr active Granted
- 1976-01-19 BE BE1007143A patent/BE837665A/fr not_active IP Right Cessation
- 1976-01-20 SE SE7600564A patent/SE428534B/xx not_active IP Right Cessation
- 1976-01-21 DK DK022876A patent/DK151381C/da active
- 1976-01-21 CH CH73576A patent/CH609887A5/xx not_active IP Right Cessation
- 1976-01-22 LU LU74230A patent/LU74230A1/xx unknown
- 1976-01-22 JP JP632476A patent/JPS5724177B2/ja not_active Expired
- 1976-01-22 AR AR261993A patent/AR211112A1/es active
- 1976-01-27 GB GB318476A patent/GB1477995A/en not_active Expired
-
1979
- 1979-03-22 KE KE2941A patent/KE2941A/xx unknown
- 1979-05-10 HK HK310/79A patent/HK31079A/xx unknown
- 1979-12-30 MY MY248/79A patent/MY7900248A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111732522A (zh) * | 2020-07-21 | 2020-10-02 | 山东国邦药业有限公司 | 一种脱氧土霉素的制备方法 |
| CN111732522B (zh) * | 2020-07-21 | 2022-10-18 | 山东国邦药业有限公司 | 一种脱氧土霉素的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| BE837665A (fr) | 1976-07-19 |
| AU1043376A (en) | 1977-07-28 |
| IE41936L (en) | 1976-07-28 |
| DK151381B (da) | 1987-11-30 |
| CH609887A5 (enExample) | 1979-03-30 |
| SE7600564L (sv) | 1976-07-29 |
| AR211112A1 (es) | 1977-10-31 |
| CA1035352A (en) | 1978-07-25 |
| DK151381C (da) | 1988-06-13 |
| NL7600334A (nl) | 1976-07-30 |
| FR2299079A1 (fr) | 1976-08-27 |
| DE2554524A1 (de) | 1976-07-29 |
| FR2299079B1 (enExample) | 1978-02-10 |
| KE2941A (en) | 1979-04-06 |
| JPS5724177B2 (enExample) | 1982-05-22 |
| ES444143A1 (es) | 1977-05-01 |
| HK31079A (en) | 1979-05-18 |
| IE41936B1 (en) | 1980-04-23 |
| SE428534B (sv) | 1983-07-11 |
| DE2554524B2 (de) | 1978-04-13 |
| LU74230A1 (enExample) | 1976-12-31 |
| NL159598B (nl) | 1979-03-15 |
| MY7900248A (en) | 1979-12-31 |
| US3962131A (en) | 1976-06-08 |
| DE2554524C3 (de) | 1979-03-15 |
| JPS5199697A (enExample) | 1976-09-02 |
| MX4844E (es) | 1982-10-28 |
| DK22876A (da) | 1976-07-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19940127 |