CH384568A - Procédé de préparation de 6-désoxytétracyclines - Google Patents

Procédé de préparation de 6-désoxytétracyclines

Info

Publication number: CH384568A
Authority: CH; Switzerland
Prior art keywords: tetracycline; deoxytetracyclines; solution; reduction; preparation
Prior art date: 1957-03-01

Application number

CH5612158A

Other languages

English (en)

French (fr)

Inventor

Daniel Mccormick 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

1964-11-30

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

1964-11-30 Publication of CH384568A publication Critical patent/CH384568A/fr

Links

238000000034 method Methods 0.000 title claims description 20
230000008569 process Effects 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 8
239000004098 Tetracycline Substances 0.000 claims description 30
235000019364 tetracycline Nutrition 0.000 claims description 30
150000003522 tetracyclines Chemical class 0.000 claims description 30
229930101283 tetracycline Natural products 0.000 claims description 25
150000001875 compounds Chemical class 0.000 claims description 24
229960002180 tetracycline Drugs 0.000 claims description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 21
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 11
239000004327 boric acid Substances 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 9
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 claims description 7
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 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
239000004100 Oxytetracycline Substances 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
229960000625 oxytetracycline Drugs 0.000 claims description 5
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
235000019366 oxytetracycline Nutrition 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 5
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 claims description 5
LJVDOBHBFMLPMI-XRNKAMNCSA-N (4s,4as,5as,6s,12ar)-7-bromo-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC(Br)=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 LJVDOBHBFMLPMI-XRNKAMNCSA-N 0.000 claims description 4
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
229910052796 boron Inorganic materials 0.000 claims description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
229910052782 aluminium Inorganic materials 0.000 claims description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
238000006317 isomerization reaction Methods 0.000 claims description 3
239000011777 magnesium Substances 0.000 claims description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
159000000007 calcium salts Chemical class 0.000 claims description 2
229910052749 magnesium Inorganic materials 0.000 claims description 2
229910052697 platinum Inorganic materials 0.000 claims description 2
239000002798 polar solvent Substances 0.000 claims description 2
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
239000000203 mixture Substances 0.000 description 28
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
239000000243 solution Substances 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 20
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
XMEVHPAGJVLHIG-FMZCEJRJSA-N chembl454950 Chemical compound [Cl-].C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H]([NH+](C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O XMEVHPAGJVLHIG-FMZCEJRJSA-N 0.000 description 8
238000006722 reduction reaction Methods 0.000 description 8
229960004989 tetracycline hydrochloride Drugs 0.000 description 8
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
230000000844 anti-bacterial effect Effects 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000000047 product Substances 0.000 description 7
SGKRLCUYIXIAHR-AKNGSSGZSA-N (4s,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-AKNGSSGZSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
241000193996 Streptococcus pyogenes Species 0.000 description 6
239000013078 crystal Substances 0.000 description 6
238000002156 mixing Methods 0.000 description 6
229940040944 tetracyclines Drugs 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 5
230000003115 biocidal effect Effects 0.000 description 5
239000000872 buffer Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
238000002798 spectrophotometry method Methods 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
238000000862 absorption spectrum Methods 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
239000003242 anti bacterial agent Substances 0.000 description 4
229940088710 antibiotic agent Drugs 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
230000002949 hemolytic effect Effects 0.000 description 4
238000011946 reduction process Methods 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
241000191967 Staphylococcus aureus Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
150000001447 alkali salts Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
238000006345 epimerization reaction Methods 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
239000000284 extract Substances 0.000 description 3
-1 inorganic acid salt Chemical class 0.000 description 3
SGKRLCUYIXIAHR-NLJUDYQYSA-N (4r,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-NLJUDYQYSA-N 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 2
QYAPHLRPFNSDNH-MRFRVZCGSA-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;hydrochloride Chemical compound Cl.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 QYAPHLRPFNSDNH-MRFRVZCGSA-N 0.000 description 2
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
229910015900 BF3 Inorganic materials 0.000 description 2
102000016736 Cyclin Human genes 0.000 description 2
108050006400 Cyclin Proteins 0.000 description 2
241001637516 Polygonia c-album Species 0.000 description 2
241000191963 Staphylococcus epidermidis Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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
239000003153 chemical reaction reagent Substances 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
230000007935 neutral effect Effects 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
OWFJMIVZYSDULZ-DVJPNYBFSA-N (4r,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 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)C3=C(O)C2=C1O OWFJMIVZYSDULZ-DVJPNYBFSA-N 0.000 description 1
DHPRQBPJLMKORJ-XRZQSNOTSA-N (4r,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-XRZQSNOTSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
229940093475 2-ethoxyethanol Drugs 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
229920001817 Agar Polymers 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 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
241000901842 Escherichia coli W Species 0.000 description 1
239000005909 Kieselgur Substances 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
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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
150000008043 acidic salts Chemical class 0.000 description 1
239000008272 agar Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
230000004071 biological effect Effects 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
238000005119 centrifugation Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000013522 chelant Substances 0.000 description 1
230000009920 chelation Effects 0.000 description 1
239000003795 chemical substances by application Substances 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
239000012065 filter cake Substances 0.000 description 1
IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
239000012458 free base Substances 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 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
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 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
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 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
235000021395 porridge Nutrition 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
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
230000000717 retained effect Effects 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
238000003756 stirring Methods 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000004448 titration Methods 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
238000005406 washing 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH5612158A 1957-03-01 1958-02-20 Procédé de préparation de 6-désoxytétracyclines CH384568A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US64321857A	1957-03-01	1957-03-01
US64322757A	1957-03-01	1957-03-01

Publications (1)

Publication Number	Publication Date
CH384568A true CH384568A (fr)	1964-11-30

Family

ID=43466745

Family Applications (2)

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

Family Applications After (1)

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

Country Status (7)

Country	Link
AT (2)	AT206435B (da)
CH (2)	CH384568A (da)
DE (2)	DE1076676B (da)
DK (2)	DK92251C (da)
FR (2)	FR1241126A (da)
GB (2)	GB845649A (da)
MC (2)	MC48A1 (da)

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
DE1768971B2 (de) *	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- methylentetracycline und ihre saeureadditionssalze
FR1430859A (da) *	1960-05-23	1966-05-25
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 GB522258A patent/GB845649A/en not_active Expired
- 1958-02-18 GB GB522158A patent/GB855170A/en not_active Expired
- 1958-02-20 CH CH5612158A patent/CH384568A/fr unknown
- 1958-02-20 CH CH5612058A patent/CH382728A/fr unknown
- 1958-02-21 MC MC59A patent/MC48A1/xx unknown
- 1958-02-21 FR FR758758A patent/FR1241126A/fr not_active Expired
- 1958-02-21 FR FR758759A patent/FR1241127A/fr not_active Expired
- 1958-02-21 MC MC57A patent/MC49A1/xx unknown
- 1958-02-25 DE DEA28948A patent/DE1076676B/de active Pending
- 1958-02-25 DE DEA28947A patent/DE1076675B/de active Pending
- 1958-02-27 DK DK69558A patent/DK92251C/da active
- 1958-02-27 DK DK69458A patent/DK92351C/da active
- 1958-02-28 AT AT146758A patent/AT206435B/de active
- 1958-02-28 AT AT146658A patent/AT206434B/de active

Also Published As

Publication number	Publication date
MC48A1 (fr)	1958-09-11
DK92251C (da)	1961-11-27
AT206435B (de)	1959-11-25
DE1076675B (de)	1960-03-03
FR1241127A (fr)	1960-12-20
DE1076676B (de)	1960-03-03
MC49A1 (fr)	1958-09-11
GB855170A (en)	1960-11-30
CH382728A (fr)	1964-10-15
FR1241126A (fr)	1960-12-20
AT206434B (de)	1959-11-25
GB845649A (en)	1960-08-24
DK92351C (da)	1961-12-11

Publication	Publication Date	Title
CH304875A (fr)	1955-01-31	Procédé de préparation d'une nouvelle substance antibiotique.
BE487301A (da)
CA1042425A (fr)	1978-11-14	Procede de preparation d'un derive neamine et ses sels_
CH382728A (fr)	1964-10-15	Procédé de préparation de nouveaux composés de la série des tétracyclines
BE565025A (da)
EP0634995B1 (en)	1996-07-03	Process and intermediate for the purification of oxytetracycline
CA1046058A (fr)	1979-01-09	Procede de preparation d'un nouveau derive aminoglycosidique et ses sels
CH387022A (fr)	1965-01-31	Procédé de préparation de 6-désoxy-tétracyclines
BE565024A (da)
CH382729A (fr)	1964-10-15	Procédé de préparation de tétracyclines
CA1123824A (fr)	1982-05-18	Oximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments
JPS58876B2 (ja)	1983-01-08	Ｆｒ −１９２３ブツシツノセイゾウホウホウ
US4072695A (en)	1978-02-07	3α,7α-Dihydroxy-cholanic acid derivatives
EP0023178B1 (fr)	1983-10-19	Procédé de préparation de solutions concentrées d'amygdaline sous sa forme naturelle
FR2468582A1 (fr)	1981-05-08	Antibiotiques de type macrolide, leur procede de preparation et compositions therapeutiques les contenant
LU82384A1 (fr)	1980-07-31	Cristallisation du sel sesqui-sodique d'un diacide d'oxa-b-lactame antibiotique
FR2477546A1 (fr)	1981-09-11	Composes carbapenemes et leurs procedes de preparation
BE572584A (da)
CA1082697A (fr)	1980-07-29	Procede de preparation d'un nouveau derive de la desoxystreptamine et ses sels
BE572382A (da)
BE633874A (da)
CH409942A (fr)	1966-03-31	Procédé de préparation de nouveaux dérivés de la tétracycline
BE561069A (da)
HU213390B (en)	1997-06-30	Process for the purification of oxytetracycline from acetyl-decarboxamido-oxytetracycline
BE548510A (da)