CH382728A - Procédé de préparation de nouveaux composés de la série des tétracyclines - Google Patents

Procédé de préparation de nouveaux composés de la série des tétracyclines

Info

Publication number: CH382728A
Authority: CH; Switzerland
Prior art keywords: demethyl; solution; reduction; hydrogen; tetracycline
Prior art date: 1957-03-01

Application number

CH5612058A

Other languages

English (en)

French (fr)

Inventor

Daniel Mc Cormick Jerry Robert

Raymond Jensen Elmer

Original Assignee

American Cyanamid Co

Priority date (The priority date 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 date listed.)

1957-03-01

Filing date

1958-02-20

Publication date

1964-10-15

1958-02-20 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1964-10-15 Publication of CH382728A publication Critical patent/CH382728A/fr

Links

150000001875 compounds Chemical class 0.000 title claims description 24
238000000034 method Methods 0.000 title claims description 13
230000008569 process Effects 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 4
239000004098 Tetracycline Substances 0.000 title description 28
235000019364 tetracycline Nutrition 0.000 title description 28
150000003522 tetracyclines Chemical class 0.000 title description 28
229960002180 tetracycline Drugs 0.000 title description 23
229930101283 tetracycline Natural products 0.000 title description 23
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
230000009467 reduction Effects 0.000 claims description 13
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 9
239000004327 boric acid Substances 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
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 claims description 8
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 claims description 7
239000002253 acid Substances 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 5
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
229910052796 boron Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
238000006317 isomerization reaction Methods 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
FMTDIUIBLCQGJB-UHFFFAOYSA-N Demethylchlortetracyclin Natural products C1C2C(O)C3=C(Cl)C=CC(O)=C3C(=O)C2=C(O)C2(O)C1C(N(C)C)C(O)=C(C(N)=O)C2=O FMTDIUIBLCQGJB-UHFFFAOYSA-N 0.000 claims description 2
150000001447 alkali salts Chemical class 0.000 claims description 2
229910052782 aluminium Inorganic materials 0.000 claims description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000011777 magnesium Substances 0.000 claims description 2
229910052697 platinum Inorganic materials 0.000 claims description 2
239000002798 polar solvent Substances 0.000 claims description 2
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 claims 3
238000004519 manufacturing process Methods 0.000 claims 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
159000000007 calcium salts Chemical class 0.000 claims 1
239000013522 chelant Substances 0.000 claims 1
FMTDIUIBLCQGJB-SEYHBJAFSA-N demeclocycline Chemical compound C1([C@@H](O)[C@H]2C3)=C(Cl)C=CC(O)=C1C(=O)C2=C(O)[C@@]1(O)[C@@H]3[C@H](N(C)C)C(O)=C(C(N)=O)C1=O FMTDIUIBLCQGJB-SEYHBJAFSA-N 0.000 claims 1
229910052749 magnesium Inorganic materials 0.000 claims 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 20
239000000203 mixture Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
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 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 10
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
238000006722 reduction reaction Methods 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
230000000844 anti-bacterial effect Effects 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
241000191967 Staphylococcus aureus Species 0.000 description 6
230000003115 biocidal effect Effects 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
229910015900 BF3 Inorganic materials 0.000 description 5
239000000872 buffer Substances 0.000 description 5
239000013078 crystal Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
230000007935 neutral effect Effects 0.000 description 5
229940040944 tetracyclines Drugs 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
241000894006 Bacteria Species 0.000 description 4
241000193996 Streptococcus pyogenes Species 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000002949 hemolytic effect Effects 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
-1 2rethoxyethanol Substances 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
238000006345 epimerization reaction Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
238000002156 mixing Methods 0.000 description 3
238000011946 reduction process Methods 0.000 description 3
238000004448 titration Methods 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
239000004100 Oxytetracycline Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
238000000862 absorption spectrum Methods 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
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 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
230000008901 benefit Effects 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
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 2
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 2
238000004587 chromatography analysis Methods 0.000 description 2
235000019441 ethanol Nutrition 0.000 description 2
IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 2
239000011654 magnesium acetate Substances 0.000 description 2
235000011285 magnesium acetate Nutrition 0.000 description 2
229940069446 magnesium acetate Drugs 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229960000625 oxytetracycline Drugs 0.000 description 2
238000002798 spectrophotometry method Methods 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
NWXMGUDVXFXRIG-PMXORCKASA-N (4r,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide 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)C3=C(O)C2=C1O NWXMGUDVXFXRIG-PMXORCKASA-N 0.000 description 1
CIJFGLCHAOVWRZ-QKYUADJBSA-N (4s,4as,5ar,12ar)-4-(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide;hydrochloride Chemical group Cl.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 CIJFGLCHAOVWRZ-QKYUADJBSA-N 0.000 description 1
GUXHBMASAHGULD-SEYHBJAFSA-N (4s,4as,5as,6s,12ar)-7-chloro-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)=C(Cl)C=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 GUXHBMASAHGULD-SEYHBJAFSA-N 0.000 description 1
OAPVUSSHCBRCOL-KBHRXELFSA-N (4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide;hydrochloride Chemical compound Cl.C1([C@H]2O)=C(Cl)C=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 OAPVUSSHCBRCOL-KBHRXELFSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
229940093475 2-ethoxyethanol Drugs 0.000 description 1
YTTFFPATQICAQN-UHFFFAOYSA-N 2-methoxypropan-1-ol Chemical compound COC(C)CO YTTFFPATQICAQN-UHFFFAOYSA-N 0.000 description 1
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
241000193755 Bacillus cereus Species 0.000 description 1
244000063299 Bacillus subtilis Species 0.000 description 1
235000014469 Bacillus subtilis Nutrition 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241000186984 Kitasatospora aureofaciens Species 0.000 description 1
241000258241 Mantis Species 0.000 description 1
241000191938 Micrococcus luteus Species 0.000 description 1
241000186359 Mycobacterium Species 0.000 description 1
241000187480 Mycobacterium smegmatis Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241001637516 Polygonia c-album Species 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
241000588767 Proteus vulgaris Species 0.000 description 1
241000607132 Salmonella enterica subsp. enterica serovar Gallinarum Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
239000010428 baryte Substances 0.000 description 1
229910052601 baryte Inorganic materials 0.000 description 1
239000002585 base Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
230000009920 chelation Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
230000008014 freezing Effects 0.000 description 1
238000007710 freezing Methods 0.000 description 1
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229910000403 monosodium phosphate Inorganic materials 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
238000004816 paper chromatography Methods 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229940072033 potash Drugs 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical group [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229940066528 trichloroacetate Drugs 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 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)

CH5612058A 1957-03-01 1958-02-20 Procédé de préparation de nouveaux composés de la série des tétracyclines CH382728A (fr)

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
CH382728A true CH382728A (fr)	1964-10-15

Family

ID=43466745

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH5612058A CH382728A (fr)	1957-03-01	1958-02-20	Procédé de préparation de nouveaux composés de la série des tétracyclines
CH5612158A CH384568A (fr)	1957-03-01	1958-02-20	Procédé de préparation de 6-désoxytétracyclines

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH5612158A CH384568A (fr)	1957-03-01	1958-02-20	Procédé de préparation de 6-désoxytétracyclines

Country Status (7)

Country	Link
AT (2)	AT206434B (de)
CH (2)	CH382728A (de)
DE (2)	DE1076676B (de)
DK (2)	DK92351C (de)
FR (2)	FR1241126A (de)
GB (2)	GB855170A (de)
MC (2)	MC48A1 (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3160661A (en)	1958-07-28	1964-12-08	American Cyanamid Co	6-deoxytetracyclines
FR1430859A (de) *	1960-05-23	1966-05-25
DE1793556C2 (de) *	1960-05-23	1982-06-16	Pfizer Inc., 10017 New York, N.Y.	7-Chlor-5-hydroxy-6-desoxy-6-desmethyl-6-methylentetracyclin, 5-Hydroxy-6-desoxy-6-desmethyl-6-methylentetracyclin und deren Salze mit Säuren und Basen sowie diese Verbindungen enthaltende Antibiotika
US20030171340A1 (en) *	2002-02-07	2003-09-11	Jenefir Isbister	Methods of disease treatment using metal-complexed tetracycline antibiotics
NZ544826A (en) *	2003-07-25	2008-07-31	Warner Chilcott Co Inc	A doxycycline metal complex in a solid dosage form
CN107445855B (zh) *	2017-08-07	2018-12-14	绍兴市逸晨医疗科技有限公司	一种盐酸多西环素杂质c的制备方法
CN116270667B (zh) *	2023-03-21	2025-09-16	佛山市正典生物技术有限公司	一种盐酸金霉素组合物及其制备方法和用途

1958
- 1958-02-18 GB GB522158A patent/GB855170A/en not_active Expired
- 1958-02-18 GB GB522258A patent/GB845649A/en not_active Expired
- 1958-02-20 CH CH5612058A patent/CH382728A/fr unknown
- 1958-02-20 CH CH5612158A patent/CH384568A/fr unknown
- 1958-02-21 FR FR758758A patent/FR1241126A/fr not_active Expired
- 1958-02-21 MC MC59A patent/MC48A1/xx unknown
- 1958-02-21 MC MC57A patent/MC49A1/xx unknown
- 1958-02-21 FR FR758759A patent/FR1241127A/fr not_active Expired
- 1958-02-25 DE DEA28948A patent/DE1076676B/de active Pending
- 1958-02-25 DE DEA28947A patent/DE1076675B/de active Pending
- 1958-02-27 DK DK69458A patent/DK92351C/da active
- 1958-02-27 DK DK69558A patent/DK92251C/da active
- 1958-02-28 AT AT146658A patent/AT206434B/de active
- 1958-02-28 AT AT146758A patent/AT206435B/de active

Also Published As

Publication number	Publication date
DK92251C (da)	1961-11-27
FR1241126A (fr)	1960-12-20
DE1076675B (de)	1960-03-03
MC48A1 (fr)	1958-09-11
DK92351C (da)	1961-12-11
AT206434B (de)	1959-11-25
CH384568A (fr)	1964-11-30
MC49A1 (fr)	1958-09-11
GB855170A (en)	1960-11-30
FR1241127A (fr)	1960-12-20
AT206435B (de)	1959-11-25
GB845649A (en)	1960-08-24
DE1076676B (de)	1960-03-03

Publication	Publication Date	Title
CA1334407C (fr)	1995-02-14	Procede de preparation de nouvelles alcoyloximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique
CH304875A (fr)	1955-01-31	Procédé de préparation d'une nouvelle substance antibiotique.
BE487301A (de)
FR2549837A1 (fr)	1985-02-01	Procede de preparation d'ester de 1-acetoxyethyle de cefuroxime
CH384568A (fr)	1964-11-30	Procédé de préparation de 6-désoxytétracyclines
CA1042425A (fr)	1978-11-14	Procede de preparation d'un derive neamine et ses sels_
EP0634995B1 (de)	1996-07-03	Verfahren und zwischenprodukte für die reinigung von oxytetracycline
FR2465731A1 (fr)	1981-03-27	Derives de type desoxy-2 o-demethyl-3 des fortimicines a et b, utiles notamment comme medicaments antibiotiques
US2786077A (en)	1957-03-19	Desdimethylaminotetracyclines and process
CA1046058A (fr)	1979-01-09	Procede de preparation d'un nouveau derive aminoglycosidique et ses sels
BE565024A (de)
US3160661A (en)	1964-12-08	6-deoxytetracyclines
BE565025A (de)
US2538106A (en)	1951-01-16	N-methyl-d-glucosamine and derivatives thereof
CH382729A (fr)	1964-10-15	Procédé de préparation de tétracyclines
JPS58876B2 (ja)	1983-01-08	Ｆｒ −１９２３ブツシツノセイゾウホウホウ
US4374764A (en)	1983-02-22	Macrolide antibiotic
FR2477546A1 (fr)	1981-09-11	Composes carbapenemes et leurs procedes de preparation
LU82384A1 (fr)	1980-07-31	Cristallisation du sel sesqui-sodique d'un diacide d'oxa-b-lactame antibiotique
CA1082697A (fr)	1980-07-29	Procede de preparation d'un nouveau derive de la desoxystreptamine et ses sels
CH409942A (fr)	1966-03-31	Procédé de préparation de nouveaux dérivés de la tétracycline
FR2459288A1 (fr)	1981-01-09	Procede de preparation de la mildiomycine par un micro-organisme du genre streptoverticillium, dans une culture contenant un compose n-methyle
BE572584A (de)
US2990426A (en)	1961-06-27	Epimerization process for anhydrotetracycline
BE572382A (de)