ES411982A1 - Process for the preparation of alpha-6-deoxytetracyclines - Google Patents
Process for the preparation of alpha-6-deoxytetracyclinesInfo
- Publication number
- ES411982A1 ES411982A1 ES411982A ES411982A ES411982A1 ES 411982 A1 ES411982 A1 ES 411982A1 ES 411982 A ES411982 A ES 411982A ES 411982 A ES411982 A ES 411982A ES 411982 A1 ES411982 A1 ES 411982A1
- Authority
- ES
- Spain
- Prior art keywords
- general formula
- alpha
- preparation
- see formula
- type
- 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
- 238000000034 method Methods 0.000 title abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 229910000510 noble metal Inorganic materials 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
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- YJJKYKYXZZCJEE-UHFFFAOYSA-N 2,2-diphenylethylphosphane Chemical compound C=1C=CC=CC=1C(CP)C1=CC=CC=C1 YJJKYKYXZZCJEE-UHFFFAOYSA-N 0.000 abstract 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 abstract 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- LVTCZSBUROAWTE-UHFFFAOYSA-N diethyl(phenyl)phosphane Chemical compound CCP(CC)C1=CC=CC=C1 LVTCZSBUROAWTE-UHFFFAOYSA-N 0.000 abstract 1
- 238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 229910052741 iridium Inorganic materials 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 229910052762 osmium Inorganic materials 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 229910052703 rhodium Inorganic materials 0.000 abstract 1
- 229910052707 ruthenium Inorganic materials 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- -1 tributylphoafine Chemical compound 0.000 abstract 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 abstract 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 abstract 1
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Catalysts (AREA)
Abstract
Procedure for the preparation of alpha-6-dioxytetracyclines, of general formula II: **(See formula)** where Y = H, F, C1, Br, I, R = H, OH, -O-CO-R', and R'= C1 to C6 alkyl group by homogeneous catalytic hydrogenation of 6-dimethyl-6-dioxy-6-methylenetetracyclines of general formula I: **(See formula)** in which Y and R have the aforementioned meaning, with the use of catalysts soluble in the reaction medium, consisting of noble metal complexes with electron donor linkers of the phosphine, arsine, and tertiary stibnin type; the noble metals used being Rh, Pd, Ru, Os, Ir, Pt, Ni; the suitable linkers being triphenylphosphine, triphenylarsine, triphenylstibine, tributylphoafine, triethylphosphine, diethylphenylphosphine, diphenylethylphosphine; using polar solvents of the type mono- or polyoxyhydrinated alcohols from C1 to C4, N, N'-dimethylformamide, N, N'-dimethylacetamide, dioxane, tetrahydrofuran, methoxyethanol, ethoxyethanol, acetonitrile, pyridine; working at temperatures between 15º and 80ºC, for times of 1 to 8 hours in the presence of hydrogen, at pressures of 1 to 150 kg/cm2. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2095972 | 1972-02-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES411982A1 true ES411982A1 (en) | 1976-01-01 |
Family
ID=11174633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES411982A Expired ES411982A1 (en) | 1972-02-24 | 1973-02-23 | Process for the preparation of alpha-6-deoxytetracyclines |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS6114145B2 (en) |
| AT (1) | AT320627B (en) |
| AU (1) | AU477038B2 (en) |
| CA (1) | CA1003410A (en) |
| CH (1) | CH579531A5 (en) |
| DE (1) | DE2308227C2 (en) |
| DK (1) | DK153394C (en) |
| ES (1) | ES411982A1 (en) |
| GB (1) | GB1418137A (en) |
| IL (1) | IL41600A (en) |
| NL (1) | NL178591C (en) |
| NO (1) | NO138563C (en) |
| PH (1) | PH10072A (en) |
| SE (1) | SE389862B (en) |
| ZA (1) | ZA731178B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE435619C (en) * | 1973-02-01 | 1985-11-18 | Pfizer | PROCEDURE FOR PREPARING A 6ALFA DEOXYTETRACYCLINE |
| US3954862A (en) * | 1973-04-20 | 1976-05-04 | Pfizer Inc. | Process for producing α-6-deoxytetracyclines |
| PT74303B (en) * | 1982-01-19 | 1983-08-08 | Joao Emerico Villax | PROCESS FOR THE PREPARATION OF NEW CATALYZERS CONTAINING RHODIUM AND USE THEREOF |
| CN111732522B (en) * | 2020-07-21 | 2022-10-18 | 山东国邦药业有限公司 | Preparation method of doxycycline |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1430859A (en) * | 1960-05-23 | 1966-05-25 |
-
1973
- 1973-02-19 CH CH234973A patent/CH579531A5/xx not_active IP Right Cessation
- 1973-02-19 GB GB811973A patent/GB1418137A/en not_active Expired
- 1973-02-20 CA CA164,204A patent/CA1003410A/en not_active Expired
- 1973-02-20 DE DE2308227A patent/DE2308227C2/en not_active Expired
- 1973-02-20 ZA ZA731178A patent/ZA731178B/en unknown
- 1973-02-21 SE SE7302447A patent/SE389862B/en unknown
- 1973-02-21 DK DK093273A patent/DK153394C/en not_active IP Right Cessation
- 1973-02-22 PH PH14362*A patent/PH10072A/en unknown
- 1973-02-22 NL NLAANVRAGE7302506,A patent/NL178591C/en not_active IP Right Cessation
- 1973-02-22 IL IL41600A patent/IL41600A/en unknown
- 1973-02-22 AT AT155773A patent/AT320627B/en not_active IP Right Cessation
- 1973-02-22 AU AU52502/73A patent/AU477038B2/en not_active Expired
- 1973-02-23 NO NO737/73A patent/NO138563C/en unknown
- 1973-02-23 ES ES411982A patent/ES411982A1/en not_active Expired
- 1973-02-24 JP JP48022592A patent/JPS6114145B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6114145B2 (en) | 1986-04-17 |
| NO138563C (en) | 1978-09-27 |
| CA1003410A (en) | 1977-01-11 |
| AT320627B (en) | 1975-02-25 |
| DE2308227A1 (en) | 1973-08-30 |
| DK153394C (en) | 1993-08-02 |
| NL7302506A (en) | 1973-08-28 |
| GB1418137A (en) | 1975-12-17 |
| DK153394B (en) | 1988-07-11 |
| CH579531A5 (en) | 1976-09-15 |
| JPS4897864A (en) | 1973-12-13 |
| PH10072A (en) | 1976-08-05 |
| NL178591B (en) | 1985-11-18 |
| DE2308227C2 (en) | 1983-01-13 |
| AU5250273A (en) | 1974-08-22 |
| ZA731178B (en) | 1973-11-28 |
| AU477038B2 (en) | 1976-10-14 |
| NL178591C (en) | 1992-09-16 |
| IL41600A (en) | 1975-07-28 |
| IL41600A0 (en) | 1973-04-30 |
| NO138563B (en) | 1978-06-19 |
| SE389862B (en) | 1976-11-22 |
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