DE2631676A1 - Verfahren zur herstellung von anhydro-5-hydroxy-tetracyclin - Google Patents
Verfahren zur herstellung von anhydro-5-hydroxy-tetracyclinInfo
- Publication number
- DE2631676A1 DE2631676A1 DE19762631676 DE2631676A DE2631676A1 DE 2631676 A1 DE2631676 A1 DE 2631676A1 DE 19762631676 DE19762631676 DE 19762631676 DE 2631676 A DE2631676 A DE 2631676A DE 2631676 A1 DE2631676 A1 DE 2631676A1
- Authority
- DE
- Germany
- Prior art keywords
- anhydro
- mixture
- tetracycline
- hydroxy
- hydroxytetracycline
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 239000004098 Tetracycline Substances 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 229960002180 tetracycline Drugs 0.000 claims description 7
- 230000018044 dehydration Effects 0.000 claims description 6
- 238000006297 dehydration reaction Methods 0.000 claims description 6
- 229940071103 sulfosalicylate Drugs 0.000 claims description 6
- 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 claims description 5
- MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical compound OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 claims description 5
- 229940087646 methanolamine Drugs 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 235000019364 tetracycline Nutrition 0.000 description 5
- 150000003522 tetracyclines Chemical class 0.000 description 5
- 239000012453 solvate Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229930101283 tetracycline Natural products 0.000 description 4
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229940040944 tetracyclines Drugs 0.000 description 2
- SVDOODSCHVSYEK-IFLJXUKPSA-N (4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydron;chloride Chemical compound Cl.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)C3=C(O)C2=C1O SVDOODSCHVSYEK-IFLJXUKPSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- IJCMDGBKHKZSJL-UHFFFAOYSA-N acetonitrile sulfuric acid Chemical compound S(=O)(=O)(O)O.S(O)(O)(=O)=O.C(C)#N IJCMDGBKHKZSJL-UHFFFAOYSA-N 0.000 description 1
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- CYDMQBQPVICBEU-UHFFFAOYSA-N chlorotetracycline Natural products C1=CC(Cl)=C2C(O)(C)C3CC4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-UHFFFAOYSA-N 0.000 description 1
- CYDMQBQPVICBEU-XRNKAMNCSA-N chlortetracycline 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)=C3C(=O)C2=C1O CYDMQBQPVICBEU-XRNKAMNCSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- QZIQJVCYUQZDIR-UHFFFAOYSA-N mechlorethamine hydrochloride Chemical compound Cl.ClCCN(C)CCCl QZIQJVCYUQZDIR-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- FKSLYSSVKFYJKE-UHFFFAOYSA-N n,n-diethylethanamine;methanol Chemical compound OC.CCN(CC)CC FKSLYSSVKFYJKE-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 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 description 1
- 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 description 1
- 229940072172 tetracycline antibiotic Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU178975A YU37118B (en) | 1975-07-14 | 1975-07-14 | Process for preparing 5a,5-anhydro-5-hydroxy-tetracycline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2631676A1 true DE2631676A1 (de) | 1977-02-03 |
Family
ID=25555580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762631676 Withdrawn DE2631676A1 (de) | 1975-07-14 | 1976-07-14 | Verfahren zur herstellung von anhydro-5-hydroxy-tetracyclin |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT344323B (enExample) |
| DE (1) | DE2631676A1 (enExample) |
| FR (1) | FR2318146A1 (enExample) |
| GB (1) | GB1509677A (enExample) |
| YU (1) | YU37118B (enExample) |
-
1975
- 1975-07-14 YU YU178975A patent/YU37118B/xx unknown
-
1976
- 1976-07-05 AT AT487976A patent/AT344323B/de not_active IP Right Cessation
- 1976-07-06 GB GB2807876A patent/GB1509677A/en not_active Expired
- 1976-07-13 FR FR7621453A patent/FR2318146A1/fr active Granted
- 1976-07-14 DE DE19762631676 patent/DE2631676A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| ATA487976A (de) | 1977-11-15 |
| GB1509677A (en) | 1978-05-04 |
| AT344323B (de) | 1978-07-10 |
| YU37118B (en) | 1984-08-31 |
| FR2318146B1 (enExample) | 1980-08-29 |
| FR2318146A1 (fr) | 1977-02-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE68922241T2 (de) | Verfahren zur Herstellung von Erythromcin A-oxim oder eines Salzes davon. | |
| DE60003509T2 (de) | Herstellung von nicht-kristallinen und kristallinen Dihydratformen von Azithromycin | |
| DE1300934B (de) | Verfahren zur Herstellung von 6-Desoxy-6-desmethyl-6-methylen-tetracyclinen bzw. ihren Salzen mit Saeuren oder Basen | |
| DE3881576T2 (de) | Anthracyclinderivate und ihre Verwendung. | |
| DE69510999T2 (de) | Terazosinmonohydrochlorid und Verfahren und Zwischenprodukte für seine Herstellung | |
| DE69813830T2 (de) | Verbessertes verfahren zur herstellung antiparasitärer mittel | |
| DE2425983B2 (de) | Sulfonsaeuresalze von acylcholinen, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zusammensetzung | |
| DE2929058C2 (de) | N,N,N-Trimethylammonium-methylsulfate der Polyenmakrolidmethylester und Verfahren zu deren Herstellung | |
| DE2740950A1 (de) | Verfahren zur herstellung von flavonen | |
| DE1287578B (de) | Verfahren zum voruebergehenden Schutz von Carboxylgruppen | |
| DE2117442B2 (de) | Verfahren zur Herstellung eines a -e-Desoxytetracyclins | |
| DE69212002T2 (de) | Verfahren und zwischenprodukte für die reinigung von oxytetracycline | |
| DE1958514C3 (de) | Apovincaminsaureamid | |
| DE1143817C2 (de) | Verfahren zur Herstellung von 6-Phenoxyacylamidopenicillansaeure-derivaten und von nicht giftigen Salzen derselben | |
| DE2719916C2 (de) | Verfahren zur Herstellung von 2,9-Dioxatricyclo[4,3,1,0↑3↑↑,↑↑7↑]decanen | |
| DE1804983A1 (de) | Verfahren zur Herstellung von Cephalosporansaeurederivaten | |
| DE2814974A1 (de) | Neue n hoch 2 -t-butyl-11a-halo-6-demethyl-6-desoxy-6-methylen-tetracycline und verfahren zu ihrer herstellung | |
| DE3207021A1 (de) | Aminoacridin-(alpha)- und/oder (beta)-(d)-n-glykosid- und/oder aminoacridin-(alpha)- und/oder (beta)-(l)-n-glykosidderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE69605520T2 (de) | Natrium-Orthohydroxymandelat-Phenol-Wasser-Komplexe, Verfahren zu deren Herstellung sowie Verwendung zur Isolation des Natrium Orthohydroxymandelats | |
| CH449006A (de) | Verfahren zur Herstellung von Fusidinsäure- und Dihydrofusidinsäurederivaten | |
| DE2506356A1 (de) | Neue acylphenoxypropansulfosaeuren, deren salze sowie suesstoffpraeparate, die diese verbindungen enthalten | |
| DE2856534A1 (de) | 11-alkanoyl-4''desoxy-4''-isonitrilo-oleandomycin-derivate und ihre verwendung | |
| DE1620592A1 (de) | Neue Lincomycinderivate und Verfahren zu ihrer Herstellung | |
| DE2208631C3 (de) | N-Isobornyloxycarbonylcephalosporin C, Verfahren zu seiner Herstellung und Verwendung zur Herstellung von Cephalosporin C | |
| DE2131945B2 (de) | Verfahren zum abtrennen von alpha6-desoxy-5-hydroxy-tetracyclin hoher reinheit aus einem reaktionsgemisch |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |