CH616080A5 - - Google Patents
Download PDFInfo
- Publication number
- CH616080A5 CH616080A5 CH1640076A CH1640076A CH616080A5 CH 616080 A5 CH616080 A5 CH 616080A5 CH 1640076 A CH1640076 A CH 1640076A CH 1640076 A CH1640076 A CH 1640076A CH 616080 A5 CH616080 A5 CH 616080A5
- Authority
- CH
- Switzerland
- Prior art keywords
- pyrrolidone
- magnesium
- pharmaceutically acceptable
- solution
- weight
- Prior art date
Links
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 86
- 239000004100 Oxytetracycline Substances 0.000 claims description 53
- 229960000625 oxytetracycline Drugs 0.000 claims description 53
- 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 53
- 235000019366 oxytetracycline Nutrition 0.000 claims description 52
- 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 52
- 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 claims description 42
- 229960003722 doxycycline Drugs 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 40
- 229960002180 tetracycline Drugs 0.000 claims description 38
- 239000004098 Tetracycline Substances 0.000 claims description 34
- 235000019364 tetracycline Nutrition 0.000 claims description 34
- 229930101283 tetracycline Natural products 0.000 claims description 34
- 239000000395 magnesium oxide Substances 0.000 claims description 33
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 33
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 33
- 150000003522 tetracyclines Chemical group 0.000 claims description 33
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 31
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 31
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 27
- 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 24
- 229960004475 chlortetracycline Drugs 0.000 claims description 23
- 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 20
- 239000004099 Chlortetracycline Substances 0.000 claims description 19
- 235000019365 chlortetracycline Nutrition 0.000 claims description 19
- 150000002681 magnesium compounds Chemical class 0.000 claims description 17
- 239000011777 magnesium Substances 0.000 claims description 16
- 229910052749 magnesium Inorganic materials 0.000 claims description 15
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 14
- 230000003115 biocidal effect Effects 0.000 claims description 12
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 9
- 239000001110 calcium chloride Substances 0.000 claims description 9
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000003242 anti bacterial agent Substances 0.000 claims description 6
- 229940043430 calcium compound Drugs 0.000 claims description 6
- 150000001674 calcium compounds Chemical class 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000013522 chelant Substances 0.000 claims 8
- 238000011065 in-situ storage Methods 0.000 claims 4
- 229940088710 antibiotic agent Drugs 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 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 claims 1
- 239000000243 solution Substances 0.000 description 99
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
- 239000000203 mixture Substances 0.000 description 49
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- 230000000694 effects Effects 0.000 description 33
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 24
- OGQYJDHTHFAPRN-UHFFFAOYSA-N 2-fluoro-6-(trifluoromethyl)benzonitrile Chemical group FC1=CC=CC(C(F)(F)F)=C1C#N OGQYJDHTHFAPRN-UHFFFAOYSA-N 0.000 description 14
- 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 14
- 229960003185 chlortetracycline hydrochloride Drugs 0.000 description 14
- 229940091250 magnesium supplement Drugs 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 10
- 229960004989 tetracycline hydrochloride Drugs 0.000 description 10
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- ADXMPQWGTCFPGL-UHFFFAOYSA-L [Mg+2].O=C.[O-]S[O-] Chemical compound [Mg+2].O=C.[O-]S[O-] ADXMPQWGTCFPGL-UHFFFAOYSA-L 0.000 description 8
- 229910001425 magnesium ion Inorganic materials 0.000 description 8
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- 239000006184 cosolvent Substances 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 229940017705 formaldehyde sulfoxylate Drugs 0.000 description 4
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 229940072172 tetracycline antibiotic Drugs 0.000 description 4
- PTNZGHXUZDHMIQ-UHFFFAOYSA-N 4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide;hydrochloride Chemical group Cl.C1=CC=C2C(C)C(C(O)C3C(C(O)=C(C(N)=O)C(=O)C3N(C)C)(O)C3=O)C3=C(O)C2=C1O PTNZGHXUZDHMIQ-UHFFFAOYSA-N 0.000 description 3
- 241000283725 Bos Species 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 230000036765 blood level Effects 0.000 description 3
- 229960004082 doxycycline hydrochloride Drugs 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 3
- 239000011654 magnesium acetate Substances 0.000 description 3
- 235000011285 magnesium acetate Nutrition 0.000 description 3
- 229940069446 magnesium acetate Drugs 0.000 description 3
- 229960002337 magnesium chloride Drugs 0.000 description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 description 3
- 235000011147 magnesium chloride Nutrition 0.000 description 3
- 229960004368 oxytetracycline hydrochloride Drugs 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 239000003182 parenteral nutrition solution Substances 0.000 description 3
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- -1 Faminoethanol Chemical class 0.000 description 2
- 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 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229940072107 ascorbate Drugs 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 229910001424 calcium ion Inorganic materials 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 229960003390 magnesium sulfate Drugs 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007929 subcutaneous injection Substances 0.000 description 2
- 238000010254 subcutaneous injection Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 1
- KZDCMKVLEYCGQX-UDPGNSCCSA-N 2-(diethylamino)ethyl 4-aminobenzoate;(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;hydrate Chemical compound O.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 KZDCMKVLEYCGQX-UDPGNSCCSA-N 0.000 description 1
- JCUQWSIALJCIEE-UHFFFAOYSA-N 3,4-dichlorothiolane 1,1-dioxide Chemical group ClC1CS(=O)(=O)CC1Cl JCUQWSIALJCIEE-UHFFFAOYSA-N 0.000 description 1
- NLJVXZFCYKWXLH-DXTIXLATSA-N 3-[(3r,6s,9s,12s,15s,17s,20s,22r,25s,28s)-20-(2-amino-2-oxoethyl)-9-(3-aminopropyl)-3,22,25-tribenzyl-15-[(4-hydroxyphenyl)methyl]-6-(2-methylpropyl)-2,5,8,11,14,18,21,24,27-nonaoxo-12-propan-2-yl-1,4,7,10,13,16,19,23,26-nonazabicyclo[26.3.0]hentriacontan Chemical compound C([C@H]1C(=O)N[C@H](C(=O)N[C@@H](CCCN)C(=O)N[C@H](C(N[C@H](CC=2C=CC=CC=2)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(O)=O)N1)=O)CC(C)C)C(C)C)C1=CC=C(O)C=C1 NLJVXZFCYKWXLH-DXTIXLATSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 102000016736 Cyclin Human genes 0.000 description 1
- 108050006400 Cyclin Proteins 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- RZCHTMXTKQHYDT-UHFFFAOYSA-N N-Lactoyl ethanolamine Chemical compound CC(O)C(=O)NCCO RZCHTMXTKQHYDT-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 108010021006 Tyrothricin Proteins 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 235000021028 berry Nutrition 0.000 description 1
- 150000001669 calcium Chemical class 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- RKLXDNHNLPUQRB-TVJUEJKUSA-N chembl564271 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]2C(C)SC[C@H](N[C@@H](CC(N)=O)C(=O)NC(=O)[C@@H](NC2=O)CSC1C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)NC(=C)C(=O)N[C@@H](CCCCN)C(O)=O)NC(=O)[C@H]1NC(=O)C(=C\C)/NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]2NC(=O)CNC(=O)[C@@H]3CCCN3C(=O)[C@@H](NC(=O)[C@H]3N[C@@H](CC(C)C)C(=O)NC(=O)C(=C)NC(=O)CC[C@H](NC(=O)[C@H](NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CC=4C5=CC=CC=C5NC=4)CSC3)C(O)=O)C(C)SC2)C(C)C)C(C)SC1)C1=CC=CC=C1 RKLXDNHNLPUQRB-TVJUEJKUSA-N 0.000 description 1
- 229960005091 chloramphenicol Drugs 0.000 description 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- DFBKLUNHFCTMDC-PICURKEMSA-N dieldrin Chemical compound C([C@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@H]2[C@@H]2[C@H]1O2 DFBKLUNHFCTMDC-PICURKEMSA-N 0.000 description 1
- 229950006824 dieldrin Drugs 0.000 description 1
- NGPMUTDCEIKKFM-UHFFFAOYSA-N dieldrin Natural products CC1=C(Cl)C2(Cl)C3C4CC(C5OC45)C3C1(Cl)C2(Cl)Cl NGPMUTDCEIKKFM-UHFFFAOYSA-N 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- HALQELOKLVRWRI-VDBOFHIQSA-N doxycycline hyclate Chemical compound O.[Cl-].[Cl-].CCO.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H]([NH+](C)C)[C@@H]1[C@H]2O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H]([NH+](C)C)[C@@H]1[C@H]2O HALQELOKLVRWRI-VDBOFHIQSA-N 0.000 description 1
- 229960001172 doxycycline hyclate Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 229940044170 formate Drugs 0.000 description 1
- JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 229940097042 glucuronate Drugs 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 229940049906 glutamate Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 1
- SXQFCVDSOLSHOQ-UHFFFAOYSA-N lactamide Chemical compound CC(O)C(N)=O SXQFCVDSOLSHOQ-UHFFFAOYSA-N 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 229960002809 lindane Drugs 0.000 description 1
- 229940097364 magnesium acetate tetrahydrate Drugs 0.000 description 1
- 229940050906 magnesium chloride hexahydrate Drugs 0.000 description 1
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 1
- 239000001755 magnesium gluconate Substances 0.000 description 1
- 229960003035 magnesium gluconate Drugs 0.000 description 1
- 235000015778 magnesium gluconate Nutrition 0.000 description 1
- OVGXLJDWSLQDRT-UHFFFAOYSA-L magnesium lactate Chemical compound [Mg+2].CC(O)C([O-])=O.CC(O)C([O-])=O OVGXLJDWSLQDRT-UHFFFAOYSA-L 0.000 description 1
- 239000000626 magnesium lactate Substances 0.000 description 1
- 229960004658 magnesium lactate Drugs 0.000 description 1
- 235000015229 magnesium lactate Nutrition 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- IAKLPCRFBAZVRW-XRDLMGPZSA-L magnesium;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoate;hydrate Chemical compound O.[Mg+2].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 IAKLPCRFBAZVRW-XRDLMGPZSA-L 0.000 description 1
- XKPKPGCRSHFTKM-UHFFFAOYSA-L magnesium;diacetate;tetrahydrate Chemical compound O.O.O.O.[Mg+2].CC([O-])=O.CC([O-])=O XKPKPGCRSHFTKM-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005341 metaphosphate group Chemical group 0.000 description 1
- 229940014662 pantothenate Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 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
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 229960003010 sodium sulfate Drugs 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 108010082567 subtilin Proteins 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960003281 tyrothricin Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
- A61K31/787—Polymers containing nitrogen containing heterocyclic rings having nitrogen as a ring hetero atom
- A61K31/79—Polymers of vinyl pyrrolidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/65—Tetracyclines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/02—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/646,295 US4018889A (en) | 1976-01-02 | 1976-01-02 | Oxytetracycline compositions |
| CA268,177A CA1075603A (en) | 1976-01-02 | 1976-12-17 | Stable solutions of doxycycline in aqueous 2-pyrrolidone |
| KR7700012A KR810000900B1 (ko) | 1976-01-02 | 1977-01-06 | 항생물질 조성제의 안정화 방법 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH616080A5 true CH616080A5 (instruction) | 1980-03-14 |
Family
ID=27164830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1640076A CH616080A5 (instruction) | 1976-01-02 | 1976-12-28 |
Country Status (29)
| Country | Link |
|---|---|
| US (3) | US4018889A (instruction) |
| JP (1) | JPS5290616A (instruction) |
| KR (1) | KR810000900B1 (instruction) |
| AR (1) | AR209242A1 (instruction) |
| AT (1) | AT345977B (instruction) |
| BE (1) | BE849885A (instruction) |
| BG (1) | BG36493A3 (instruction) |
| CA (2) | CA1075603A (instruction) |
| CH (1) | CH616080A5 (instruction) |
| CS (1) | CS205030B2 (instruction) |
| DD (1) | DD129997A5 (instruction) |
| DE (1) | DE2659152C2 (instruction) |
| DK (1) | DK145753C (instruction) |
| EG (1) | EG12291A (instruction) |
| FI (1) | FI56116C (instruction) |
| FR (1) | FR2336937A1 (instruction) |
| GB (1) | GB1520197A (instruction) |
| GR (1) | GR65305B (instruction) |
| HK (1) | HK30181A (instruction) |
| IE (1) | IE44767B1 (instruction) |
| IN (1) | IN145845B (instruction) |
| KE (1) | KE3166A (instruction) |
| LU (1) | LU76493A1 (instruction) |
| NL (1) | NL166620C (instruction) |
| OA (1) | OA05524A (instruction) |
| PT (1) | PT66017B (instruction) |
| SE (1) | SE435997B (instruction) |
| SU (1) | SU1309901A3 (instruction) |
| ZA (1) | ZA767689B (instruction) |
Families Citing this family (103)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4126680A (en) * | 1977-04-27 | 1978-11-21 | Pfizer Inc. | Tetracycline antibiotic compositions |
| EP0009559B1 (de) * | 1978-08-01 | 1982-08-25 | Ciba-Geigy Ag | Stabile flüssige Arzneimittelformulierung, ihre Herstellung und Verwendung |
| EP0012496B1 (en) * | 1978-12-08 | 1983-07-20 | Beecham Group Plc | A process for the preparation of a solid sodium amoxycillin and aqueous solutions thereof |
| US4259331A (en) * | 1979-04-16 | 1981-03-31 | Pfizer Inc. | Oxytetracycline compositions |
| ATE4166T1 (de) * | 1979-07-02 | 1983-08-15 | Pfizer Inc. | Langwirkende injizierbare sulfonamidzusammensetzungen. |
| EP0022342B1 (en) * | 1979-07-05 | 1983-06-15 | Pfizer Inc. | Sulfonamide solutions |
| US4303643A (en) * | 1979-07-05 | 1981-12-01 | Pfizer Inc. | Sulfonamide compositions |
| US4386083A (en) * | 1980-04-10 | 1983-05-31 | Walter Hacke | Injectable oxytetracycline compositions |
| CA1163197A (en) * | 1980-04-10 | 1984-03-06 | Herman Horn | Injectable oxytetracycline compositions |
| US4399127A (en) * | 1980-04-10 | 1983-08-16 | Diamond Shamrock Corporation | Injectable oxytetracycline compositions |
| US4374826A (en) * | 1980-07-21 | 1983-02-22 | Pfizer Inc. | Sulfonamide compositions |
| NL178941C (nl) * | 1982-06-15 | 1986-06-16 | Aesculaap Bv | Werkwijze voor de bereiding van een waterig oxytetracyclinepreparaat. |
| US4769232A (en) * | 1984-03-22 | 1988-09-06 | Pfizer Inc. | Parenteral formulations of indolmycin |
| IE74244B1 (en) * | 1985-10-01 | 1997-07-16 | Bimeda Res Dev Ltd | A process for preparing an antibiotic composition |
| HU194493B (en) * | 1985-11-27 | 1988-02-29 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing primycin-containing colloidal basic gel and compositions comprising the same |
| FR2608044B1 (fr) * | 1986-12-10 | 1992-09-11 | Sogeval | Composition antibiotique aqueuse a usage veterinaire |
| US4906475A (en) * | 1988-02-16 | 1990-03-06 | Paco Pharmaceutical Services | Estradiol transdermal delivery system |
| US6756365B2 (en) * | 1991-11-06 | 2004-06-29 | Trustees Of Tufts College | Reducing tetracycline resistance in living cells |
| EP0626171A1 (de) * | 1993-05-26 | 1994-11-30 | Winfried Dörnhöfer | Injektionslösung für die intravenöse oder intramuskuläre Verabreichung an Tiere |
| ES2130069B1 (es) * | 1997-04-10 | 2000-03-01 | Basf Labiana S A | Preparacion farmaceutica con liberacion retardada del producto activo. |
| US20020077276A1 (en) * | 1999-04-27 | 2002-06-20 | Fredeking Terry M. | Compositions and methods for treating hemorrhagic virus infections and other disorders |
| US8106225B2 (en) * | 1999-09-14 | 2012-01-31 | Trustees Of Tufts College | Methods of preparing substituted tetracyclines with transition metal-based chemistries |
| CN102336680A (zh) | 1999-09-14 | 2012-02-01 | 塔夫茨大学信托人 | 用基于过渡金属的化学制备取代四环素的方法 |
| US6849615B2 (en) | 1999-09-14 | 2005-02-01 | Paratek Pharmaceuticals, Inc. | 13-substituted methacycline compounds |
| US6500812B2 (en) | 1999-09-14 | 2002-12-31 | Paratek Pharmaceuticals, Inc. | 13-substituted methacycline compounds |
| EP1255565A1 (de) * | 2000-01-13 | 2002-11-13 | MERCK PATENT GmbH | Pharmazeutische zubereitungen enthaltend 2-pyrrolidon als lösungsvermittler |
| JP2003523963A (ja) * | 2000-01-24 | 2003-08-12 | トラスティーズ・オブ・タフツ・カレッジ | クリプトスポリジウム・パルヴム関連疾患の治療のためのテトラサイクリン化合物 |
| HUP0300082A2 (en) | 2000-03-31 | 2003-05-28 | Paratek Pharmaceuticals | 7- and 9-carbamate, urea, thiourea, thiocarbamate, and heteroaryl-amino substituted tetracycline derivatives, process for their preparation and use and pharmaceutical compositions containing them |
| EP2308863A1 (en) * | 2000-05-15 | 2011-04-13 | Paratek Pharmaceuticals, Inc. | 7-substituted fused ring tetracycline compounds |
| US20020132798A1 (en) * | 2000-06-16 | 2002-09-19 | Nelson Mark L. | 7-phenyl-substituted tetracycline compounds |
| AU2001268475A1 (en) * | 2000-06-16 | 2002-01-02 | Trustees Of Tufts College | 7-phenyl-substituted tetracycline compounds |
| US20040224927A1 (en) * | 2000-06-16 | 2004-11-11 | Trustees Of Tufts College | 7-N-substituted phenyl tetracycline compounds |
| IL153674A0 (en) | 2000-07-07 | 2003-07-06 | Tufts College | 13-substituted methacycline compounds |
| BR0112265A (pt) | 2000-07-07 | 2003-06-24 | Tufts College | Compostos de tetraciclina substituìda, e de sanciclina 7-substituìda, método para tratar um estado responsivo à tetraciclina em um indivìduo, e, composição farmacêutica |
| US20050143353A1 (en) * | 2000-07-07 | 2005-06-30 | Paratek Pharmaceuticals, Inc. | 13-Substituted methacycline compounds |
| US7094806B2 (en) | 2000-07-07 | 2006-08-22 | Trustees Of Tufts College | 7, 8 and 9-substituted tetracycline compounds |
| CA2415086A1 (en) | 2000-07-07 | 2002-01-17 | Trustees Of Tufts College | 7,8 and 9-substituted tetracycline compounds |
| ATE336481T1 (de) | 2000-07-07 | 2006-09-15 | Tufts College | 9-substituierte minocyclinverbindungen |
| RU2178698C1 (ru) * | 2000-11-28 | 2002-01-27 | Закрытое Акционерное Общество "Нита-Фарм" | Способ получения композиции магниевого комплекса окситетрациклина пролонгированного действия |
| WO2002072506A2 (en) | 2001-03-13 | 2002-09-19 | Paratek Pharmaceuticals, Inc. | 7-pyrollyl tetracycline compounds and methods of use thereof |
| US7553828B2 (en) | 2001-03-13 | 2009-06-30 | Paratek Pharmaceuticals, Inc. | 9-aminomethyl substituted minocycline compounds |
| EP1241160A1 (en) * | 2001-03-13 | 2002-09-18 | Glaxo Group Limited | Tetracycline derivatives and their use as antibiotic agents |
| WO2002072532A1 (en) | 2001-03-13 | 2002-09-19 | Paratek Pharmaceuticals, Inc. | 7, 9-substituted tetracycline compounds |
| EP1379255A2 (en) * | 2001-03-14 | 2004-01-14 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds as antifungal agents |
| JP2005504722A (ja) | 2001-03-14 | 2005-02-17 | パラテック ファーマシューティカルズ インコーポレイテッド | 相乗的抗真菌薬剤としての置換テトラサイクリン化合物 |
| US8088820B2 (en) * | 2001-04-24 | 2012-01-03 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds for the treatment of malaria |
| EP2186793A1 (en) | 2001-04-24 | 2010-05-19 | Paratek Pharmaceuticals, Inc. | Substituted Tetracycline Compounds |
| US20030181371A1 (en) * | 2001-12-28 | 2003-09-25 | Angiotech Pharmaceuticals, Inc. | Compositions and methods of using collajolie |
| EP2311798A1 (en) | 2002-01-08 | 2011-04-20 | Paratek Pharmaceuticals, Inc. | 4-dedimethylamino tetracycline compounds |
| EP2301534A1 (en) | 2002-03-08 | 2011-03-30 | Paratek Pharmaceuticals, Inc. | Amino-methyl substituted tetracycline compounds |
| IL164180A0 (en) | 2002-03-21 | 2005-12-18 | Paratek Pharm Innc | Substituted tetracycline compounds |
| US6958161B2 (en) | 2002-04-12 | 2005-10-25 | F H Faulding & Co Limited | Modified release coated drug preparation |
| KR101089429B1 (ko) | 2002-07-12 | 2011-12-07 | 파라테크 파마슈티컬스, 인크. | 3, 10, 및 12ａ 치환된 테트라시클린 화합물 |
| JP2006503898A (ja) | 2002-10-24 | 2006-02-02 | パラテック ファーマシューティカルズ， インク． | マラリア治療のための置換テトラサイクリン化合物 |
| EP1585555A2 (en) * | 2002-12-27 | 2005-10-19 | Angiotech International Ag | Compositions and methods of using collagen and mmpi |
| AU2004259661B2 (en) | 2003-07-09 | 2011-11-10 | Paratek Pharmaceuticals, Inc. | Prodrugs of 9-aminomethyl tetracycline compounds |
| US20060287283A1 (en) * | 2003-07-09 | 2006-12-21 | Paratek Pharmaceuticals, Inc. | Prodrugs of 9-aminomethyl tetracycline compounds |
| EP2298322A3 (en) | 2003-07-09 | 2011-05-11 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| WO2005011707A1 (en) * | 2003-07-25 | 2005-02-10 | Warner Chilcott Company, Inc. | A doxycycline metal complex in a solid dosage form |
| JP5010284B2 (ja) * | 2004-01-15 | 2012-08-29 | パラテック ファーマシューティカルズ インコーポレイテッド | テトラサイクリン化合物の芳香族ａ環誘導体 |
| TWI261038B (en) * | 2004-08-11 | 2006-09-01 | Bo-Cheng Chen | Bicycle gear-shifting handgrip |
| EP1805134B1 (en) * | 2004-10-25 | 2012-06-20 | Paratek Pharmaceuticals, Inc. | 4-aminotetracyclines and methods of use thereof |
| US8466132B2 (en) | 2004-10-25 | 2013-06-18 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| ES2588584T3 (es) * | 2005-01-21 | 2016-11-03 | Warner Chilcott Company, Llc | Un complejo metálico de tetraciclina en una forma de dosificación sólida |
| US8088755B2 (en) | 2005-02-04 | 2012-01-03 | Paratek Pharmaceuticals, Inc. | 11a, 12-derivatives of tetracycline compounds |
| US9192615B2 (en) | 2008-08-06 | 2015-11-24 | Medicis Pharmaceutical Corporation | Method for the treatment of acne and certain dosage forms thereof |
| US7541347B2 (en) * | 2007-04-02 | 2009-06-02 | Medicis Pharmaceutical Coropration | Minocycline oral dosage forms for the treatment of acne |
| US20080241235A1 (en) * | 2007-04-02 | 2008-10-02 | Medicis Pharmaceutical Corporation | Minocycline oral dosage forms for the treatment of acne |
| US8722650B1 (en) | 2005-06-24 | 2014-05-13 | Medicis Pharmaceutical Corporation | Extended-release minocycline dosage forms |
| US20080242642A1 (en) | 2007-04-02 | 2008-10-02 | Medicis Pharmaceutical Corporation | Minocycline oral dosage forms for the treatment of acne |
| US7919483B2 (en) * | 2005-06-24 | 2011-04-05 | Medicis Pharmaceutical Corporation | Method for the treatment of acne |
| US7544373B2 (en) * | 2007-04-02 | 2009-06-09 | Medicis Pharmaceutical Corporation | Minocycline oral dosage forms for the treatment of acne |
| US8252776B2 (en) | 2007-04-02 | 2012-08-28 | Medicis Pharmaceutical Corporation | Minocycline oral dosage forms for the treatment of acne |
| JP2009502809A (ja) * | 2005-07-21 | 2009-01-29 | パラテック ファーマシューティカルズ インコーポレイテッド | １０−置換テトラサイクリンおよびその使用方法 |
| AU2007208214B2 (en) | 2006-01-24 | 2013-02-14 | Paratek Pharmaceuticals, Inc. | Methods of increasing oral bioavailability of tetracyclines |
| US20070244335A1 (en) * | 2006-04-17 | 2007-10-18 | Teva Pharmaceutical Industries Ltd. | Isolation of tetracycline derivatives |
| WO2007127292A2 (en) * | 2006-04-24 | 2007-11-08 | Teva Pharmaceutical Industries Ltd. | Tigeycline crystalline forms and processes for preparation thereof |
| US8198470B2 (en) * | 2006-04-24 | 2012-06-12 | Teva Pharmaceutical Industries Ltd. | Crystalline form II of tigecycline and processes for preparation thereof |
| EP2026776A2 (en) * | 2006-05-15 | 2009-02-25 | Paratek Pharmaceuticals, Inc. | Methods of regulating expression of genes or of gene products using substituted tetracycline compounds |
| WO2008045507A2 (en) | 2006-10-11 | 2008-04-17 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds for treatment of bacillus anthracis infections |
| IL302749A (en) | 2006-12-21 | 2023-07-01 | Paratek Pharm Innc | A tetracycline compound, a pharmaceutical composition comprising the tetracycline compound, and the tetracycline compound of the pharmaceutical composition for treating a tetracycline responsive state |
| EP2120963B1 (en) | 2006-12-21 | 2018-09-12 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds for treatment of inflammatory skin disorders |
| US20080241197A1 (en) * | 2007-04-02 | 2008-10-02 | Medicis Pharmaceutical Corporation | Minocycline dosage forms for the treatment of acne |
| WO2008127722A1 (en) | 2007-04-12 | 2008-10-23 | Paratek Pharmaceuticals, Inc. | Methods for treating spinal muscular atrophy using tetracycline compounds |
| CA2688662A1 (en) * | 2007-04-27 | 2008-11-06 | Paratek Pharmaceuticals, Inc. | Methods for synthesizing and purifying aminoalkyl tetracycline compounds |
| KR20100042276A (ko) | 2007-07-06 | 2010-04-23 | 파라테크 파마슈티컬스, 인크. | 치환 테트라사이클린 화합물의 합성방법 |
| AU2009220171A1 (en) * | 2008-03-05 | 2009-09-11 | Paratek Pharmaceuticals, Inc. | Minocycline compounds and methods of use thereof |
| PT2271348T (pt) | 2008-03-28 | 2018-04-16 | Paratek Pharm Innc | Formulação de comprimido oral de composto de tetraciclina |
| AU2009236631A1 (en) * | 2008-04-14 | 2009-10-22 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| TW202216656A (zh) | 2008-05-19 | 2022-05-01 | 美商Ｐｒｔｋ Ｓｐｖ２公司 | 四環素化合物之甲苯磺酸鹽及同素異形體 |
| BRPI0918050A2 (pt) * | 2008-09-19 | 2015-09-22 | Paratek Pharm Innc | compostos de tetraciclina para o tratamento de artrite reumatoide e metodos relacionados de tratamento |
| EP2990051B1 (en) | 2009-04-10 | 2016-10-26 | Tufts Medical Center, Inc. | Par-1 activation by metalloproteinase-1 (mmp-1) |
| CN102970992B (zh) | 2010-05-12 | 2016-07-06 | 莱姆派克斯制药公司 | 四环素组合物 |
| PL2707003T3 (pl) | 2011-05-12 | 2019-11-29 | Paratek Pharm Innc | Krystaliczne sole amidu kwasu (4s,4as,5ar,12as)-4-dimetyloamino-3,10,12,12a-tetrahydroksy-7-[(metoksy(metylo)amino)metylo]-1,11-diokso- 1,4,4a,5,5a,6,11,12a-oktahydronaftaceno- 2-karboksylowego i sposoby ich stosowania |
| US9561241B1 (en) | 2011-06-28 | 2017-02-07 | Medicis Pharmaceutical Corporation | Gastroretentive dosage forms for minocycline |
| WO2015021387A2 (en) * | 2013-08-09 | 2015-02-12 | Britt George N | Formulations for control and prevention of periodontal and perimplant diseases and other diseases and conditions of the mouth, and supra and sub-gingival delivery methods and systems for such formulations |
| CN103536530A (zh) * | 2013-10-30 | 2014-01-29 | 王玉万 | 盐酸多西环素长效注射剂及制备方法 |
| CN107708665B (zh) | 2015-03-23 | 2022-07-22 | 贝尔生物制药有限公司 | 用于皮肤病学用途的药用四环素组合物 |
| CN104721133B (zh) * | 2015-04-14 | 2018-05-18 | 四川美嘉龙生物科技有限公司 | 一种土霉素制剂及制备方法 |
| RU2019113715A (ru) | 2016-11-01 | 2020-12-03 | Паратек Фармасьютикалс, Инк. | 9-аминометилминоциклиновые соединения и их применение для лечениия внебольничной бактериальной пневмонии(вбп) |
| ES2962380T3 (es) | 2017-07-21 | 2024-03-18 | Almirall Llc | Sareciclina para el tratamiento de lesiones de acné no inflamatorias |
| TWI841543B (zh) | 2017-11-28 | 2024-05-11 | 德商Ｃ 樂克塔股份有限公司 | 生產海藻糖之方法 |
| US11426351B2 (en) | 2019-12-26 | 2022-08-30 | Sunstar Inc. | Process for producing a pharmaceutical composition containing micro particles |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB805026A (en) * | 1956-03-02 | 1958-11-26 | Konink Nl Gisten Spiritusfabri | Process for enhancing the solubility of medicines in water |
| GB802111A (en) * | 1956-09-25 | 1958-10-01 | Irwin Irville Lubowe | Improved non-toxic pesticidal compositions |
| US2990331A (en) * | 1956-11-23 | 1961-06-27 | Pfizer & Co C | Stable solutions of salts of tetracyclines for parenteral administration |
| DE1091287B (de) * | 1957-04-09 | 1960-10-20 | Byk Gulden Lomberg Chem Fab | Verfahren zur Herstellung stabiler, waessriger Loesungen von Tyrothricin und Subtilin |
| US2980584A (en) * | 1957-10-29 | 1961-04-18 | Pfizer & Co C | Parenteral magnesium oxytetracycline acetic or lactic acid carboxamide vehicle preparation |
| US2987437A (en) * | 1958-03-06 | 1961-06-06 | Gen Aniline & Film Corp | Nematocidal composition |
| US3062717A (en) * | 1958-12-11 | 1962-11-06 | Pfizer & Co C | Intramuscular calcium tetracycline acetic or lactic acid carboxamide vehicle preparation |
| NL6607516A (instruction) * | 1966-05-31 | 1967-12-01 | ||
| US3957972A (en) * | 1966-05-31 | 1976-05-18 | Koninklijke Nederlandsche Gist-En Spiritusfabriek N.V. | Stable solutions of oxytetracycline suitable for parenteral and peroral administration and process of preparation |
| DE1767891C3 (de) * | 1968-06-28 | 1980-10-30 | Pfizer | Verfahren zur Herstellung von wäßrigen arzneilichen Lösungen für die parenterale, perorale und lokale Anwendung mit einem Gehalt an einem Tetracyclinderivat |
| US3957980A (en) * | 1972-10-26 | 1976-05-18 | Pfizer Inc. | Doxycycline parenteral compositions |
| GB1508601A (en) * | 1974-01-19 | 1978-04-26 | Norbrook Labor Ltd | Oxytetracycline solution |
| DK138974B (da) * | 1974-02-19 | 1978-11-27 | Ciba Geigy Ag | Fremgangsmåde til fremstilling af vandige oxytetracyclinopløsninger til parenteral, peroral og lokal anvendelse. |
| US3957994A (en) * | 1974-12-19 | 1976-05-18 | Nelson Research & Development Company | Topical anti-inflammatory composition and method of use |
| US3932653A (en) * | 1974-12-19 | 1976-01-13 | Nelson Research & Development Co. | Composition and method for topical administration of griseofulvin |
| US3969516A (en) * | 1974-12-19 | 1976-07-13 | Nelson Research & Development Company | Composition and method for treatment of acne |
| GB1538903A (en) | 1975-04-11 | 1979-01-24 | Nelson Res & Dev | Carrier for a topically applied physiologically active agent or cosmetic agent |
-
1976
- 1976-01-02 US US05/646,295 patent/US4018889A/en not_active Expired - Lifetime
- 1976-12-07 US US05/748,355 patent/US4081528A/en not_active Expired - Lifetime
- 1976-12-07 US US05/748,600 patent/US4086332A/en not_active Expired - Lifetime
- 1976-12-10 SE SE7613959A patent/SE435997B/xx not_active IP Right Cessation
- 1976-12-15 IN IN2209/CAL/76A patent/IN145845B/en unknown
- 1976-12-15 GB GB52394/76A patent/GB1520197A/en not_active Expired
- 1976-12-17 CA CA268,177A patent/CA1075603A/en not_active Expired
- 1976-12-21 IE IE2800/76A patent/IE44767B1/en not_active IP Right Cessation
- 1976-12-23 CA CA268,611A patent/CA1072012A/en not_active Expired
- 1976-12-23 GR GR52477A patent/GR65305B/el unknown
- 1976-12-24 JP JP15613476A patent/JPS5290616A/ja active Granted
- 1976-12-27 PT PT66017A patent/PT66017B/pt unknown
- 1976-12-28 CH CH1640076A patent/CH616080A5/fr not_active IP Right Cessation
- 1976-12-28 NL NL7614470.A patent/NL166620C/xx not_active IP Right Cessation
- 1976-12-28 EG EG800/76A patent/EG12291A/xx active
- 1976-12-28 BE BE1007849A patent/BE849885A/xx not_active IP Right Cessation
- 1976-12-28 DK DK584676A patent/DK145753C/da not_active IP Right Cessation
- 1976-12-28 SU SU762436954A patent/SU1309901A3/ru active
- 1976-12-28 FI FI763716A patent/FI56116C/fi not_active IP Right Cessation
- 1976-12-28 DE DE2659152A patent/DE2659152C2/de not_active Expired
- 1976-12-28 AT AT971776A patent/AT345977B/de active
- 1976-12-29 DD DD7600196699A patent/DD129997A5/xx unknown
- 1976-12-29 ZA ZA767689A patent/ZA767689B/xx unknown
- 1976-12-29 BG BG035054A patent/BG36493A3/xx unknown
- 1976-12-29 AR AR266034A patent/AR209242A1/es active
- 1976-12-29 CS CS768758A patent/CS205030B2/cs unknown
- 1976-12-29 OA OA56026A patent/OA05524A/xx unknown
- 1976-12-29 FR FR7639413A patent/FR2336937A1/fr active Granted
- 1976-12-29 LU LU76493A patent/LU76493A1/xx unknown
-
1977
- 1977-01-06 KR KR7700012A patent/KR810000900B1/ko not_active Expired
-
1981
- 1981-07-02 HK HK301/81A patent/HK30181A/xx unknown
- 1981-10-15 KE KE3166A patent/KE3166A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH616080A5 (instruction) | ||
| CH630260A5 (fr) | Compositions antibiotiques a base d'une tetracycline. | |
| US4482554A (en) | Pharmaceutical compositions containing oxicam derivatives and process for their preparation | |
| FR2696740A1 (fr) | Dérivés prodrogués de la diméthylbiguanide et applications comme médicaments. | |
| US4772460A (en) | Method of reducing the swelling or pain associated with antibiotics compositions | |
| US4081527A (en) | Chlortetracycline compositions | |
| FR2584405A1 (fr) | Sels de furosemide, composition pharmaceutique les contenant et leur procede de preparation | |
| KR850001300B1 (ko) | 옥시테트라사이클린 조성물의 제조방법 | |
| HU177873B (en) | Further developped process for preparing an aequous solution containing a complex of n-/3-chloro-4-/4-chloro-phenoxy/-phenyl/-2-hydroxy-3,5-diiodo-benzamide with polyvinyl-pyrrolidone | |
| EP0448583A1 (fr) | Composes organometalliques, leurs modes de preparation et compositions pharmaceutiques les contenant | |
| JPS61267547A (ja) | 微生物の生育を制御する新規５−アルキルスルホニルサリチルアニリド | |
| CH642378A5 (fr) | Nouveau derive du paracetamol, son procede de preparation et son utilisation en therapeutique. | |
| CH622023A5 (en) | Process for the preparation of a water-soluble compound based on a substituted phenylaminoalcohol | |
| JPS5821888B2 (ja) | スイセイラフオキサニドセイザイ | |
| BE1001262A4 (fr) | Procede en vue de provoquer la regression de la leucemie et l'inhibition de la croissance des tumeurs chez les mammiferes. | |
| KR100498268B1 (ko) | 피롤리돈계 양쪽성 계면활성제 | |
| FR2608044A1 (fr) | Composition antibiotique aqueuse a usage veterinaire | |
| WO2025085641A1 (en) | The synthesis and characterization of end-group modified poloxamers | |
| FI57883C (fi) | Foerfarande foer framstaellning av en stabil klortetracyklinloesning | |
| PL110324B1 (en) | Method of obtaining stable antibiotic preparations | |
| LU83081A1 (fr) | Compositions antitumeurs | |
| LU87274A1 (fr) | Procede en vue de provoquer la regression de la leucemie et l'inhibition de la croissance des tumeurs chez les mammiferes | |
| LU86350A1 (fr) | Sels et compositions pharmaceutiques hydrosolubles a base d'aminoalcools |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |