SU632298A3 - Способ получени -6-дезокси-5-окситетрациклина или его солей - Google Patents
Способ получени -6-дезокси-5-окситетрациклина или его солейInfo
- Publication number
- SU632298A3 SU632298A3 SU742032110A SU2032110A SU632298A3 SU 632298 A3 SU632298 A3 SU 632298A3 SU 742032110 A SU742032110 A SU 742032110A SU 2032110 A SU2032110 A SU 2032110A SU 632298 A3 SU632298 A3 SU 632298A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- catalyst
- isomer
- palladium
- copper
- product
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 239000004100 Oxytetracycline Substances 0.000 title claims description 6
- 229960000625 oxytetracycline Drugs 0.000 title claims description 6
- 150000003839 salts Chemical class 0.000 title claims description 6
- 239000003054 catalyst Substances 0.000 claims description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 24
- 239000000047 product Substances 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052763 palladium Inorganic materials 0.000 claims description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 11
- 229910052802 copper Inorganic materials 0.000 claims description 11
- 239000010949 copper Substances 0.000 claims description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052737 gold Inorganic materials 0.000 claims description 7
- 239000010931 gold Substances 0.000 claims description 7
- 238000005984 hydrogenation reaction Methods 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 4
- 229910045601 alloy Inorganic materials 0.000 claims description 4
- 239000000956 alloy Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 229910052709 silver Inorganic materials 0.000 claims description 4
- 239000004332 silver Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical compound OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 claims 2
- 229910000881 Cu alloy Inorganic materials 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003245 coal Substances 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 claims 1
- 238000006317 isomerization reaction Methods 0.000 claims 1
- LKWKIVHUCKVYOA-UHFFFAOYSA-N phosphoric acid;trifluoroborane Chemical compound FB(F)F.OP(O)(O)=O LKWKIVHUCKVYOA-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229940071103 sulfosalicylate Drugs 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004098 Tetracycline Substances 0.000 description 2
- 229960002180 tetracycline Drugs 0.000 description 2
- 235000019364 tetracycline Nutrition 0.000 description 2
- 229930101283 tetracycline Natural products 0.000 description 2
- 150000003522 tetracyclines Chemical class 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical compound NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000011221 initial treatment Methods 0.000 description 1
- IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical class C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 229940070891 pyridium Drugs 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI1387A HU167250B (enrdf_load_stackoverflow) | 1973-06-08 | 1973-06-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU632298A3 true SU632298A3 (ru) | 1978-11-05 |
Family
ID=10994484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU742032110A SU632298A3 (ru) | 1973-06-08 | 1974-06-06 | Способ получени -6-дезокси-5-окситетрациклина или его солей |
Country Status (12)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK386784A (da) * | 1983-08-17 | 1985-02-18 | Hovione Int Ltd | Fremgangsmaade til fremstilling af alfa-6-desoxy-tetracykliner |
| HU198173B (en) * | 1987-09-18 | 1989-08-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing doxycycline |
| ES2019267T3 (es) * | 1989-04-03 | 1993-09-16 | Ranbaxy Laboratories, Ltd. | Un procedimiento para la preparacion de alfa-6-desoxitetraciclinas. |
| CN102086165B (zh) * | 2010-12-29 | 2013-06-19 | 开封制药(集团)有限公司 | Pd催化剂在生产强力霉素氢化工艺中的应用 |
-
1973
- 1973-06-08 HU HUCI1387A patent/HU167250B/hu unknown
-
1974
- 1974-03-04 CS CS743969A patent/CS175748B1/cs unknown
- 1974-06-04 AT AT457574A patent/AT332969B/de not_active IP Right Cessation
- 1974-06-06 FR FR7419510A patent/FR2232539A1/fr not_active Withdrawn
- 1974-06-06 SU SU742032110A patent/SU632298A3/ru active
- 1974-06-06 DD DD178988A patent/DD113894A1/xx unknown
- 1974-06-07 JP JP49064162A patent/JPS5052051A/ja active Pending
- 1974-06-07 ES ES427070A patent/ES427070A1/es not_active Expired
- 1974-06-07 GB GB2545174A patent/GB1436670A/en not_active Expired
- 1974-06-07 DK DK307174A patent/DK307174A/da not_active Application Discontinuation
- 1974-06-07 BE BE145164A patent/BE816029A/xx unknown
- 1974-06-07 PL PL1974171743A patent/PL93707B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU167250B (enrdf_load_stackoverflow) | 1975-09-27 |
| JPS5052051A (enrdf_load_stackoverflow) | 1975-05-09 |
| DK307174A (enrdf_load_stackoverflow) | 1975-02-03 |
| ES427070A1 (es) | 1976-07-16 |
| FR2232539A1 (enrdf_load_stackoverflow) | 1975-01-03 |
| CS175748B1 (en) | 1977-05-31 |
| BE816029A (fr) | 1974-09-30 |
| PL93707B1 (enrdf_load_stackoverflow) | 1977-06-30 |
| ATA457574A (de) | 1976-02-15 |
| DD113894A1 (enrdf_load_stackoverflow) | 1975-07-05 |
| GB1436670A (en) | 1976-05-19 |
| AT332969B (de) | 1976-10-25 |
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