GB855170A - 6-demethyl-6-deoxytetracycline and the 4-epimers thereof - Google Patents
6-demethyl-6-deoxytetracycline and the 4-epimers thereofInfo
- Publication number
- GB855170A GB855170A GB522158A GB522158A GB855170A GB 855170 A GB855170 A GB 855170A GB 522158 A GB522158 A GB 522158A GB 522158 A GB522158 A GB 522158A GB 855170 A GB855170 A GB 855170A
- Authority
- GB
- United Kingdom
- Prior art keywords
- deoxytetracycline
- demethyl
- acid
- hydrogen
- aluminium
- 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
- XDVCLKFLRAWGIT-ADOAZJKMSA-N sancycline Chemical compound C([C@H]1C2)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 XDVCLKFLRAWGIT-ADOAZJKMSA-N 0.000 title 1
- MTCQOMXDZUULRV-ADOAZJKMSA-N (4s,4as,5ar,12ar)-4-(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=CC=CC(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O MTCQOMXDZUULRV-ADOAZJKMSA-N 0.000 abstract 9
- 239000001257 hydrogen Substances 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- ICPMTQOYWXXMIG-OPDGVEILSA-K aluminum;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoate Chemical compound [Al+3].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O ICPMTQOYWXXMIG-OPDGVEILSA-K 0.000 abstract 3
- 239000002585 base Substances 0.000 abstract 3
- 239000000243 solution Substances 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 2
- 229940093475 2-ethoxyethanol Drugs 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- 229960000583 acetic acid Drugs 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000012362 glacial acetic acid Substances 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- RMVMLZHPWMTQGK-SOUFLCLCSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1([C@H]2O)=CC=CC(O)=C1C(O)=C1[C@@H]2C[C@H]2[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]2(O)C1=O RMVMLZHPWMTQGK-SOUFLCLCSA-N 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- YTTFFPATQICAQN-UHFFFAOYSA-N 2-methoxypropan-1-ol Chemical compound COC(C)CO YTTFFPATQICAQN-UHFFFAOYSA-N 0.000 abstract 1
- 229910015900 BF3 Inorganic materials 0.000 abstract 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- 239000004098 Tetracycline Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- -1 alkaline earth metal salts Chemical class 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 159000000013 aluminium salts Chemical class 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 abstract 1
- 229910001863 barium hydroxide Inorganic materials 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract 1
- 239000004327 boric acid Substances 0.000 abstract 1
- 229910052796 boron Inorganic materials 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 abstract 1
- 239000000920 calcium hydroxide Substances 0.000 abstract 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000013522 chelant Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- JCSGAUKCDAVARS-UHFFFAOYSA-N demethyltetracycline Natural products CN(C1C(=C(C(C2(C(=C3C(C4=C(C=CC=C4C(C3CC12)O)O)=O)O)O)=O)C(=O)N)O)C JCSGAUKCDAVARS-UHFFFAOYSA-N 0.000 abstract 1
- 229940093499 ethyl acetate Drugs 0.000 abstract 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 abstract 1
- 239000011654 magnesium acetate Substances 0.000 abstract 1
- 229940069446 magnesium acetate Drugs 0.000 abstract 1
- 235000011285 magnesium acetate Nutrition 0.000 abstract 1
- 159000000003 magnesium salts Chemical class 0.000 abstract 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 abstract 1
- 235000019799 monosodium phosphate Nutrition 0.000 abstract 1
- CZFNISFYDPIDNM-UHFFFAOYSA-N n,n-dimethylformamide;oxolane Chemical compound CN(C)C=O.C1CCOC1 CZFNISFYDPIDNM-UHFFFAOYSA-N 0.000 abstract 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical group [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 229960002180 tetracycline Drugs 0.000 abstract 1
- 229930101283 tetracycline Natural products 0.000 abstract 1
- 235000019364 tetracycline Nutrition 0.000 abstract 1
- 150000003522 tetracyclines Chemical class 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to 6-demethyl-6-deoxytetracycline having the formula: <FORM:0855170/IV(b)/1> the 4-epimer thereof, and salts of these compounds with an acid or a base and complexes with metal salts, e.g. aluminium, magnesium and calcium, e.g. aluminium gluconate. The base is obtained by catalytically reducing by means of hydrogen a 6-demethyltetracycline of formula: <FORM:0855170/IV(b)/2> wherein Z is hydrogen, chlorine or bromine, or the 4-epimer thereof, in a solvent solution in the presence of a substance which forms a chelate ring with a peri-dioxygenated hydro-naphthalene, e.g. boric acid, boron trihalides such as boron trifluoride, aluminium salts such as aluminium chloride and magnesium salts such as magnesium acetate. Where Z is hydrogen one mole of hydrogen is used and where Z is chlorine or bromine 2 moles of hydrogen are used. The reduction is carried out at temperatures of 0 DEG C. to 100 DEG C. and preferably at room temperature to 50 DEG C. and at hydrogen pressures of 1/2 to 100 atmospheres. The catalyst may be a metal of the platinum family especially 5% palladium hydroxide on charcoal. Specified solvents are water, dioxane, glacial acetic acid, 2-ethoxyethanol and ethyl acetate; a mixture of water and dimethylformamide (1 : 1) containing perchloric acid is preferred. The 4-epimer of 6-demethyl-6-deoxytetracycline is produced by allowing a concentrated solution of 6-demethyl-6-deoxytetracycline to stand at pH 3 to 5 and preferably 3,5 to 4,5 for 1 to 7 days. A suitable solvent is methanol, ethanol, butanol, acetone, 2-ethoxyethanol, 2-methoxypropanol, glacial acetic acid, tetrahydrofuran dimethylformamide and mixtures thereof. A suitable buffer is sodium dihydrogen phosphate. Acid salts are prepared by treating the 6-demethyl-6-deoxytetracycline with an acid, e.g. hydrochloric, sulphuric, phosphoric and trichloroacetic at pH below 4. Alkali metal and alkaline earth metal salts are obtained by treating the 6-demethyl-6-deoxytetracycline with a base such as sodium hydroxide, potassium hydroxide, calcium hydroxide or barium hydroxide at a pH above 6,0. The free 6-demethyl-6-deoxytetracycline may be obtained by adjusting a solution of the salt to pH 4 to 6. 6-demethyl-6-deoxytetracycline aluminium gluconate complex is produced by mixing 6-demethyl-6-deoxytetracycline with aluminium gluconate in aqueous solution. 6-demethyl-6-deoxytetracycline is a broad spectrum antibiotic more active against staphyloccus aureus than tetracycline and possessing some stability in acid and alkaline aqueous media. Specification 855,169 is referred to.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64322757A | 1957-03-01 | 1957-03-01 | |
| US64321857A | 1957-03-01 | 1957-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB855170A true GB855170A (en) | 1960-11-30 |
Family
ID=43466745
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB522258A Expired GB845649A (en) | 1957-03-01 | 1958-02-18 | 6-deoxytetracycline and 6-deoxyoxytetracycline |
| GB522158A Expired GB855170A (en) | 1957-03-01 | 1958-02-18 | 6-demethyl-6-deoxytetracycline and the 4-epimers thereof |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB522258A Expired GB845649A (en) | 1957-03-01 | 1958-02-18 | 6-deoxytetracycline and 6-deoxyoxytetracycline |
Country Status (7)
| Country | Link |
|---|---|
| AT (2) | AT206434B (en) |
| CH (2) | CH382728A (en) |
| DE (2) | DE1076675B (en) |
| DK (2) | DK92251C (en) |
| FR (2) | FR1241126A (en) |
| GB (2) | GB845649A (en) |
| MC (2) | MC49A1 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3160661A (en) | 1958-07-28 | 1964-12-08 | American Cyanamid Co | 6-deoxytetracyclines |
| FR1430859A (en) * | 1960-05-23 | 1966-05-25 | ||
| DE1768971B2 (en) * | 1960-05-23 | 1976-01-22 | Ausscheidung aus: 14 68 478 Pfizer Inc., New York, N.Y. (V.St.A.) | 11A-HALOGEN-6-DESOXY-6-DESMETHYL-6-METHYLENE TETRACYCLINE AND THEIR ACID ADDITIONAL SALTS |
| US20030171340A1 (en) * | 2002-02-07 | 2003-09-11 | Jenefir Isbister | Methods of disease treatment using metal-complexed tetracycline antibiotics |
| CA2533150C (en) | 2003-07-25 | 2013-03-12 | Warner Chilcott Company, Inc. | A doxycycline metal complex in a solid dosage form |
| CN107445855B (en) * | 2017-08-07 | 2018-12-14 | 绍兴市逸晨医疗科技有限公司 | A kind of preparation method of Doxycycline Hyclate impurity C |
| CN116270667B (en) * | 2023-03-21 | 2025-09-16 | 佛山市正典生物技术有限公司 | Aureomycin hydrochloride composition and preparation method and application thereof |
-
1958
- 1958-02-18 GB GB522258A patent/GB845649A/en not_active Expired
- 1958-02-18 GB GB522158A patent/GB855170A/en not_active Expired
- 1958-02-20 CH CH5612058A patent/CH382728A/en unknown
- 1958-02-20 CH CH5612158A patent/CH384568A/en unknown
- 1958-02-21 MC MC57A patent/MC49A1/en unknown
- 1958-02-21 FR FR758758A patent/FR1241126A/en not_active Expired
- 1958-02-21 MC MC59A patent/MC48A1/en unknown
- 1958-02-21 FR FR758759A patent/FR1241127A/en not_active Expired
- 1958-02-25 DE DEA28947A patent/DE1076675B/en active Pending
- 1958-02-25 DE DEA28948A patent/DE1076676B/en active Pending
- 1958-02-27 DK DK69558A patent/DK92251C/en active
- 1958-02-27 DK DK69458A patent/DK92351C/en active
- 1958-02-28 AT AT146658A patent/AT206434B/en active
- 1958-02-28 AT AT146758A patent/AT206435B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| CH384568A (en) | 1964-11-30 |
| MC48A1 (en) | 1958-09-11 |
| GB845649A (en) | 1960-08-24 |
| MC49A1 (en) | 1958-09-11 |
| FR1241127A (en) | 1960-12-20 |
| FR1241126A (en) | 1960-12-20 |
| DE1076676B (en) | 1960-03-03 |
| DK92251C (en) | 1961-11-27 |
| AT206435B (en) | 1959-11-25 |
| AT206434B (en) | 1959-11-25 |
| CH382728A (en) | 1964-10-15 |
| DK92351C (en) | 1961-12-11 |
| DE1076675B (en) | 1960-03-03 |
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