BE566475A

BE566475A -

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Publication number: BE566475A
Authority: BE; Belgium
Prior art keywords: water; salts; tetracyclines; components; tetracycline
Prior art date

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English (en)

French (fr)

Publication of BE566475A publication Critical patent/BE566475A/fr

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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 23
239000004098 Tetracycline Substances 0.000 claims description 22
235000019364 tetracycline Nutrition 0.000 claims description 22
150000003522 tetracyclines Chemical class 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 13
229930101283 tetracycline Natural products 0.000 claims description 12
229940040944 tetracyclines Drugs 0.000 claims description 12
229960002180 tetracycline Drugs 0.000 claims description 10
150000007513 acids Chemical class 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 5
150000001735 carboxylic acids Chemical group 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
159000000032 aromatic acids Chemical group 0.000 claims description 3
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
102000016736 Cyclin Human genes 0.000 claims 1
108050006400 Cyclin Proteins 0.000 claims 1
230000001747 exhibiting effect Effects 0.000 claims 1
150000007529 inorganic bases Chemical class 0.000 claims 1
150000007530 organic bases Chemical class 0.000 claims 1
239000000243 solution Substances 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000002244 precipitate Substances 0.000 description 9
229960004989 tetracycline hydrochloride Drugs 0.000 description 9
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
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
229960004909 aminosalicylic acid Drugs 0.000 description 6
238000003756 stirring Methods 0.000 description 6
FVVDKUPCWXUVNP-UHFFFAOYSA-M Aminosalicylate sodium anhydrous Chemical compound [Na+].NC1=CC=C(C([O-])=O)C(O)=C1 FVVDKUPCWXUVNP-UHFFFAOYSA-M 0.000 description 5
206010013911 Dysgeusia Diseases 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000002585 base Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000000796 flavoring agent Substances 0.000 description 4
235000019634 flavors Nutrition 0.000 description 4
WVTDZOPAGHNYTM-IZGCTLQUSA-N (4s,4as,5as,6r,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;4-amino-2-hydroxybenzoic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1.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 WVTDZOPAGHNYTM-IZGCTLQUSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
159000000007 calcium salts Chemical class 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
230000009967 tasteless effect Effects 0.000 description 3
NWXMGUDVXFXRIG-WESIUVDSSA-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 Chemical class 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-WESIUVDSSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000003513 alkali Substances 0.000 description 2
-1 alkaline earth metal salts Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000000155 melt Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
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 2
SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 1
ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-M 4-aminosalicylate(1-) Chemical compound NC1=CC=C(C([O-])=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-M 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 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
238000001816 cooling Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000000203 mixture Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
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 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
150000003870 salicylic acids Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000012976 tarts Nutrition 0.000 description 1
239000011800 void material Substances 0.000 description 1