BE523640A - - Google Patents
Info
- Publication number
- BE523640A BE523640A BE523640DA BE523640A BE 523640 A BE523640 A BE 523640A BE 523640D A BE523640D A BE 523640DA BE 523640 A BE523640 A BE 523640A
- Authority
- BE
- Belgium
- Prior art keywords
- sep
- chlorotetracycline
- product
- catalyst
- antibiotic
- Prior art date
Links
- DHPRQBPJLMKORJ-XRNKAMNCSA-N (4S,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O DHPRQBPJLMKORJ-XRNKAMNCSA-N 0.000 claims description 14
- 230000003115 biocidal Effects 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 239000004098 Tetracycline Substances 0.000 claims description 9
- 235000019364 tetracycline Nutrition 0.000 claims description 9
- 229960002180 Tetracycline Drugs 0.000 claims description 8
- OFVLGDICTFRJMM-WESIUVDSSA-N Tetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[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 OFVLGDICTFRJMM-WESIUVDSSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 230000001264 neutralization Effects 0.000 claims description 2
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 32
- 239000000047 product Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000004599 antimicrobial Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 244000005700 microbiome Species 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 229940064005 Antibiotic throat preparations Drugs 0.000 description 3
- 229940083879 Antibiotics FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE Drugs 0.000 description 3
- 229940042052 Antibiotics for systemic use Drugs 0.000 description 3
- 229940042786 Antitubercular Antibiotics Drugs 0.000 description 3
- 229940093922 Gynecological Antibiotics Drugs 0.000 description 3
- 229940024982 Topical Antifungal Antibiotics Drugs 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000008043 acidic salts Chemical class 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 229940079866 intestinal antibiotics Drugs 0.000 description 3
- 229940005935 ophthalmologic Antibiotics Drugs 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- YCIHPQHVWDULOY-FMZCEJRJSA-N (4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride Chemical group Cl.C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O YCIHPQHVWDULOY-FMZCEJRJSA-N 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L Barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 229960000625 Oxytetracycline Drugs 0.000 description 2
- IWVCMVBTMGNXQD-PXOLEDIWSA-N Oxytetracycline Chemical compound 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 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N Silver nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229960004989 tetracycline hydrochloride Drugs 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-Ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 241000589562 Brucella Species 0.000 description 1
- 229960004475 Chlortetracycline Drugs 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- 239000004100 Oxytetracycline Substances 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 206010039447 Salmonellosis Diseases 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 229940063650 Terramycin Drugs 0.000 description 1
- 229940040944 Tetracyclines Drugs 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000845 anti-microbial Effects 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- CXLSVMAGOLTCSL-UHFFFAOYSA-J calcium;barium(2+);dicarbonate Chemical compound [Ca+2].[Ba+2].[O-]C([O-])=O.[O-]C([O-])=O CXLSVMAGOLTCSL-UHFFFAOYSA-J 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- -1 chlorotetracycline compound Chemical class 0.000 description 1
- 235000019365 chlortetracycline Nutrition 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent Effects 0.000 description 1
- 230000001627 detrimental Effects 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- AHEVKYYGXVEWNO-UEPZRUIBSA-N lymecycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(=O)NCNCCCC[C@H](N)C(O)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O AHEVKYYGXVEWNO-UEPZRUIBSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000003472 neutralizing Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 230000003287 optical Effects 0.000 description 1
- 235000019366 oxytetracycline Nutrition 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000001954 sterilising Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- NEDFZELJKGZAQF-UHFFFAOYSA-J strontium;barium(2+);dicarbonate Chemical compound [Sr+2].[Ba+2].[O-]C([O-])=O.[O-]C([O-])=O NEDFZELJKGZAQF-UHFFFAOYSA-J 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE523640A true BE523640A (pt) |
Family
ID=158512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE523640D BE523640A (pt) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE523640A (pt) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3160661A (en) * | 1958-07-28 | 1964-12-08 | American Cyanamid Co | 6-deoxytetracyclines |
-
0
- BE BE523640D patent/BE523640A/fr unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3160661A (en) * | 1958-07-28 | 1964-12-08 | American Cyanamid Co | 6-deoxytetracyclines |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1121343A (fr) | Procede de preparation d'une forme cristalline du sel de sodium d'un derive oximine de l'acide 7-amino thiazolyl acetamido cephalosporanique | |
| FR2688506A1 (fr) | Procede de preparation de sels de l'acide clavulanique. | |
| CA1042425A (fr) | Procede de preparation d'un derive neamine et ses sels_ | |
| BE523640A (pt) | ||
| FR2807427A1 (fr) | Plastifiant energetique comprenant un melange eutectique de bis (2,2-dinitropropyl) formal, de 2,2 dinitropropyl- 2,2-dinitrobutylformal et de bis (2,2-dinitrobutyl) formal, et son procede de preparation | |
| CA1046058A (fr) | Procede de preparation d'un nouveau derive aminoglycosidique et ses sels | |
| CA1140155A (fr) | PROCEDE DE PREPARATION D'UN NOUVEAU DERIVE DU 1.alpha.,25-DIHYDROXY CHOLECALCIFEROL | |
| BE506950A (pt) | ||
| BE1000157A5 (fr) | Procede de preparation de derives de la moranoline. | |
| CH387022A (fr) | Procédé de préparation de 6-désoxy-tétracyclines | |
| CH384568A (fr) | Procédé de préparation de 6-désoxytétracyclines | |
| BE1004449A4 (fr) | Procede ameliore pour la preparation de tripeptide aldehydes. | |
| FR2491471A1 (fr) | Benzoxazolinones substituees, leur preparation et leur application en therapeutique | |
| BE572382A (pt) | ||
| BE572236A (pt) | ||
| CA1042424A (fr) | Procede de preparation d'un derive de la gentamine et ses sels_ | |
| CH326864A (fr) | Procédé de purification des sels d'acides de la tétracycline | |
| BE572450A (pt) | ||
| BE593853A (pt) | ||
| BE533740A (pt) | ||
| BE550641A (pt) | ||
| BE624559A (pt) | ||
| CH406194A (fr) | Procédé de préparation de sels stables de diméthylcarboxy-alkylsulfonium | |
| BE557360A (pt) | ||
| BE563353A (pt) |