CS205030B2 - Method of producing of the stabil antibiotic means - Google Patents
Method of producing of the stabil antibiotic means Download PDFInfo
- Publication number
- CS205030B2 CS205030B2 CS768758A CS875876A CS205030B2 CS 205030 B2 CS205030 B2 CS 205030B2 CS 768758 A CS768758 A CS 768758A CS 875876 A CS875876 A CS 875876A CS 205030 B2 CS205030 B2 CS 205030B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- weight
- pyrrolidone
- tetracycline
- magnesium
- oxytetracycline
- Prior art date
Links
- 230000003115 biocidal effect Effects 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims description 41
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims abstract description 78
- 239000000203 mixture Substances 0.000 claims abstract description 63
- 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 abstract description 57
- 239000004100 Oxytetracycline Substances 0.000 claims abstract description 55
- 229960000625 oxytetracycline Drugs 0.000 claims abstract description 55
- 235000019366 oxytetracycline Nutrition 0.000 claims abstract description 55
- 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 abstract description 55
- 229960003722 doxycycline Drugs 0.000 claims abstract description 46
- 229930101283 tetracycline Natural products 0.000 claims abstract description 45
- 239000004098 Tetracycline Substances 0.000 claims abstract description 44
- 229960002180 tetracycline Drugs 0.000 claims abstract description 44
- 235000019364 tetracycline Nutrition 0.000 claims abstract description 44
- 150000003522 tetracyclines Chemical class 0.000 claims abstract description 43
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 239000002253 acid Substances 0.000 claims abstract description 30
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims abstract description 27
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims abstract description 27
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims abstract description 27
- 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 abstract description 24
- 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 abstract description 24
- 239000004099 Chlortetracycline Substances 0.000 claims abstract description 13
- 229960004475 chlortetracycline Drugs 0.000 claims abstract description 13
- 235000019365 chlortetracycline Nutrition 0.000 claims abstract description 13
- 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 abstract 5
- 239000000243 solution Substances 0.000 claims description 100
- 150000002681 magnesium compounds Chemical class 0.000 claims description 23
- 239000000395 magnesium oxide Substances 0.000 claims description 22
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 22
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 22
- 239000007864 aqueous solution Substances 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000001110 calcium chloride Substances 0.000 claims description 7
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 7
- 229940043430 calcium compound Drugs 0.000 claims description 7
- 150000001674 calcium compounds Chemical class 0.000 claims description 7
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 6
- 229940072172 tetracycline antibiotic Drugs 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 abstract description 18
- 229910052749 magnesium Inorganic materials 0.000 abstract description 18
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract description 17
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract description 3
- 239000011575 calcium Substances 0.000 abstract description 3
- 229910052791 calcium Inorganic materials 0.000 abstract 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 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-WESIUVDSSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- FZKWRPSUNUOXKJ-CVHRZJFOSA-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;hydrate Chemical compound O.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 FZKWRPSUNUOXKJ-CVHRZJFOSA-N 0.000 description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 34
- 230000000694 effects Effects 0.000 description 30
- 230000032683 aging Effects 0.000 description 18
- 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 17
- VYGBQXDNOUHIBZ-UHFFFAOYSA-L sodium formaldehyde sulphoxylate Chemical compound [Na+].[Na+].O=C.[O-]S[O-] VYGBQXDNOUHIBZ-UHFFFAOYSA-L 0.000 description 17
- 229960004989 tetracycline hydrochloride Drugs 0.000 description 17
- 230000002431 foraging effect Effects 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- OGQYJDHTHFAPRN-UHFFFAOYSA-N 2-fluoro-6-(trifluoromethyl)benzonitrile Chemical compound FC1=CC=CC(C(F)(F)F)=C1C#N OGQYJDHTHFAPRN-UHFFFAOYSA-N 0.000 description 9
- 229960003185 chlortetracycline hydrochloride Drugs 0.000 description 9
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 8
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 8
- -1 alkali metal bisulfite Chemical class 0.000 description 7
- 239000012458 free base Substances 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 239000006184 cosolvent Substances 0.000 description 6
- 229940017705 formaldehyde sulfoxylate Drugs 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 6
- 159000000003 magnesium salts Chemical class 0.000 description 6
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 241000283690 Bos taurus Species 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 229910001425 magnesium ion Inorganic materials 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 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 4
- SXQFCVDSOLSHOQ-UHFFFAOYSA-N lactamide Chemical compound CC(O)C(N)=O SXQFCVDSOLSHOQ-UHFFFAOYSA-N 0.000 description 4
- 229910001629 magnesium chloride Inorganic materials 0.000 description 4
- 235000011147 magnesium chloride Nutrition 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 238000007911 parenteral administration Methods 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 230000036765 blood level Effects 0.000 description 3
- 229910001424 calcium ion Inorganic materials 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 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
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- 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 compound 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 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 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
- HRKQOINLCJTGBK-UHFFFAOYSA-L dioxidosulfate(2-) Chemical compound [O-]S[O-] HRKQOINLCJTGBK-UHFFFAOYSA-L 0.000 description 2
- 229960004082 doxycycline hydrochloride Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- KXSFFNPTLXGGQF-UHFFFAOYSA-N magnesium;pyrrolidin-2-one Chemical compound [Mg].O=C1CCCN1 KXSFFNPTLXGGQF-UHFFFAOYSA-N 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 229960004368 oxytetracycline hydrochloride Drugs 0.000 description 2
- 239000003182 parenteral nutrition solution Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000010254 subcutaneous injection Methods 0.000 description 2
- 239000007929 subcutaneous injection Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 2
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-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
- CFMWPNYNLBQUPE-UHFFFAOYSA-N 2-aminoethanol 3-sulfanylpropane-1,2-diol Chemical compound NCCO.OCC(O)CS CFMWPNYNLBQUPE-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
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 244000248349 Citrus limon Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 108010021006 Tyrothricin Proteins 0.000 description 1
- QDCILXFPWMMNQY-LKRXSEBCSA-N [(1S,5R)-8-methyl-8-[(4-phenylphenyl)methyl]-8-azoniabicyclo[3.2.1]octan-3-yl] (2R)-3-hydroxy-2-phenylpropanoate Chemical compound C[N+]1(Cc2ccc(cc2)-c2ccccc2)[C@H]2CC[C@@H]1CC(C2)OC(=O)[C@@H](CO)c1ccccc1 QDCILXFPWMMNQY-LKRXSEBCSA-N 0.000 description 1
- NAJWWXVFAQOCBS-UHFFFAOYSA-L [Cl-].[Cl-].[Ca+2].NCCO.OCC(O)CS.O=C1CCCN1 Chemical compound [Cl-].[Cl-].[Ca+2].NCCO.OCC(O)CS.O=C1CCCN1 NAJWWXVFAQOCBS-UHFFFAOYSA-L 0.000 description 1
- JOSAZXNVODDPCR-UHFFFAOYSA-M [O-2].[Na+].[Mg+2].O=C.OS[O-].O=C1CCCN1 Chemical compound [O-2].[Na+].[Mg+2].O=C.OS[O-].O=C1CCCN1 JOSAZXNVODDPCR-UHFFFAOYSA-M 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 235000013365 dairy product Nutrition 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
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 229940079593 drug 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
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen 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
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 229960002809 lindane Drugs 0.000 description 1
- 229940097364 magnesium acetate tetrahydrate Drugs 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
- 239000005645 nematicide Substances 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 239000011644 potassium salts of orthophosphoric acid Substances 0.000 description 1
- 235000019858 potassium salts of orthophosphoric acid Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011643 sodium salts of orthophosphoric acid Substances 0.000 description 1
- 235000019857 sodium salts of orthophosphoric acid Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000011200 topical administration Methods 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
- 238000005303 weighing Methods 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)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (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 |
|---|---|
| CS205030B2 true CS205030B2 (en) | 1981-04-30 |
Family
ID=27164830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS768758A CS205030B2 (en) | 1976-01-02 | 1976-12-29 | Method of producing of the stabil antibiotic means |
Country Status (29)
| Country | Link |
|---|---|
| US (3) | US4018889A (https=) |
| JP (1) | JPS5290616A (https=) |
| KR (1) | KR810000900B1 (https=) |
| AR (1) | AR209242A1 (https=) |
| AT (1) | AT345977B (https=) |
| BE (1) | BE849885A (https=) |
| BG (1) | BG36493A3 (https=) |
| CA (2) | CA1075603A (https=) |
| CH (1) | CH616080A5 (https=) |
| CS (1) | CS205030B2 (https=) |
| DD (1) | DD129997A5 (https=) |
| DE (1) | DE2659152C2 (https=) |
| DK (1) | DK145753C (https=) |
| EG (1) | EG12291A (https=) |
| FI (1) | FI56116C (https=) |
| FR (1) | FR2336937A1 (https=) |
| GB (1) | GB1520197A (https=) |
| GR (1) | GR65305B (https=) |
| HK (1) | HK30181A (https=) |
| IE (1) | IE44767B1 (https=) |
| IN (1) | IN145845B (https=) |
| KE (1) | KE3166A (https=) |
| LU (1) | LU76493A1 (https=) |
| NL (1) | NL166620C (https=) |
| OA (1) | OA05524A (https=) |
| PT (1) | PT66017B (https=) |
| SE (1) | SE435997B (https=) |
| SU (1) | SU1309901A3 (https=) |
| ZA (1) | ZA767689B (https=) |
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 |
| IE49934B1 (en) * | 1979-07-02 | 1986-01-08 | Pfizer | Long acting sulfonamide injectable compositions |
| IE49933B1 (en) * | 1979-07-05 | 1986-01-08 | Pfizer | 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 |
| US6500812B2 (en) | 1999-09-14 | 2002-12-31 | Paratek Pharmaceuticals, Inc. | 13-substituted methacycline compounds |
| US6849615B2 (en) | 1999-09-14 | 2005-02-01 | Paratek Pharmaceuticals, Inc. | 13-substituted methacycline compounds |
| EP2327687A3 (en) * | 1999-09-14 | 2012-08-15 | Trustees Of Tufts College | Methods of preparing substituted tetracyclines with transition metal-based chemistries |
| US8106225B2 (en) * | 1999-09-14 | 2012-01-31 | Trustees Of Tufts College | Methods of preparing substituted tetracyclines with transition metal-based chemistries |
| WO2001051089A1 (de) * | 2000-01-13 | 2001-07-19 | Merck Patent Gmbh | Pharmazeutische zubereitungen enthaltend 2-pyrrolidon als lösungsvermittler |
| AU3105801A (en) | 2000-01-24 | 2001-07-31 | Trustees Of Tufts College | Tetracycline compounds for treatment of cryptosporidium parvum related disorders |
| MXPA02009482A (es) | 2000-03-31 | 2004-05-14 | Tufts College | Compuestos tetraciclinas sustituidos con grupos 7- y 9- carbamato, urea, tiourea, tiocarbamato y heteroaril-amino. |
| WO2001087824A2 (en) * | 2000-05-15 | 2001-11-22 | Paratek Pharmaceuticals, Inc. | 7-substituted fused ring tetracycline compounds |
| US20040224927A1 (en) | 2000-06-16 | 2004-11-11 | Trustees Of Tufts College | 7-N-substituted phenyl tetracycline compounds |
| US20020132798A1 (en) * | 2000-06-16 | 2002-09-19 | Nelson Mark L. | 7-phenyl-substituted tetracycline compounds |
| US20020128238A1 (en) * | 2000-06-16 | 2002-09-12 | Nelson Mark L. | 7-phenyl-substituted tetracycline compounds |
| US7094806B2 (en) * | 2000-07-07 | 2006-08-22 | Trustees Of Tufts College | 7, 8 and 9-substituted tetracycline compounds |
| US20050143353A1 (en) * | 2000-07-07 | 2005-06-30 | Paratek Pharmaceuticals, Inc. | 13-Substituted methacycline compounds |
| EA013908B1 (ru) | 2000-07-07 | 2010-08-30 | Трастис Оф Тафтс Коллидж | Замещенные соединения миноциклина (варианты), фармацевтическая композиция и способ лечения чувствительного к тетрациклину состояния млекопитающего |
| MXPA03000036A (es) | 2000-07-07 | 2003-07-14 | Tufts College | Compuestos de metaciclina sustituidos en posicion 13. |
| JP4963771B2 (ja) | 2000-07-07 | 2012-06-27 | トラスティーズ・オブ・タフツ・カレッジ | ７、８および９−置換テトラサイクリン化合物 |
| CN1450989A (zh) | 2000-07-07 | 2003-10-22 | 塔夫茨大学信托人 | 7－取代的四环素化合物 |
| RU2178698C1 (ru) * | 2000-11-28 | 2002-01-27 | Закрытое Акционерное Общество "Нита-Фарм" | Способ получения композиции магниевого комплекса окситетрациклина пролонгированного действия |
| US7553828B2 (en) * | 2001-03-13 | 2009-06-30 | Paratek Pharmaceuticals, Inc. | 9-aminomethyl substituted minocycline compounds |
| WO2002072506A2 (en) * | 2001-03-13 | 2002-09-19 | Paratek Pharmaceuticals, Inc. | 7-pyrollyl tetracycline compounds and methods of use thereof |
| WO2002072532A1 (en) | 2001-03-13 | 2002-09-19 | Paratek Pharmaceuticals, Inc. | 7, 9-substituted tetracycline compounds |
| EP1241160A1 (en) * | 2001-03-13 | 2002-09-18 | Glaxo Group Limited | Tetracycline derivatives and their use as antibiotic agents |
| WO2002072031A2 (en) | 2001-03-14 | 2002-09-19 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds as synergistic antifungal agents |
| JP2004530661A (ja) * | 2001-03-14 | 2004-10-07 | 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 | 抗真菌剤としての置換テトラサイクリン化合物 |
| EP1399414B1 (en) | 2001-04-24 | 2010-01-13 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds for the treatment of malaria |
| US8088820B2 (en) * | 2001-04-24 | 2012-01-03 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds for the treatment of malaria |
| US20030181371A1 (en) * | 2001-12-28 | 2003-09-25 | Angiotech Pharmaceuticals, Inc. | Compositions and methods of using collajolie |
| EP2311799A1 (en) * | 2002-01-08 | 2011-04-20 | Paratek Pharmaceuticals, Inc. | 4-dedimethylamino tetracycline compounds |
| JP2005526754A (ja) | 2002-03-08 | 2005-09-08 | 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 | アミノメチル置換されたテトラサイクリン化合物 |
| KR101083498B1 (ko) | 2002-03-21 | 2011-11-16 | 파라테크 파마슈티컬스, 인크. | 치환된 테트라시클린 화합물 |
| US6958161B2 (en) | 2002-04-12 | 2005-10-25 | F H Faulding & Co Limited | Modified release coated drug preparation |
| CA2492273C (en) | 2002-07-12 | 2013-02-05 | Paratek Pharmaceuticals, Inc. | 3, 10, and 12a substituted tetracycline compounds |
| WO2004038001A2 (en) | 2002-10-24 | 2004-05-06 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds for the treatment of malaria |
| US20040192658A1 (en) * | 2002-12-27 | 2004-09-30 | Angiotech International Ag | Compositions and methods of using collajolie |
| JP4738333B2 (ja) | 2003-07-09 | 2011-08-03 | 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 | ９−アミノメチルテトラサイクリン化合物のプロドラッグ |
| US20060287283A1 (en) * | 2003-07-09 | 2006-12-21 | Paratek Pharmaceuticals, Inc. | Prodrugs of 9-aminomethyl tetracycline compounds |
| CA2531728A1 (en) | 2003-07-09 | 2005-02-03 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| CN103040773A (zh) * | 2003-07-25 | 2013-04-17 | 沃纳奇尔科特有限责任公司 | 多西环素金属络合物固体剂型 |
| CA2553510C (en) * | 2004-01-15 | 2012-09-25 | Paratek Pharmaceuticals, Inc. | Aromatic a-ring derivatives of tetracycline compounds |
| TWI261038B (en) * | 2004-08-11 | 2006-09-01 | Bo-Cheng Chen | Bicycle gear-shifting handgrip |
| AU2005299294B2 (en) * | 2004-10-25 | 2012-06-07 | Paratek Pharmaceuticals, Inc. | 4-aminotetracyclines and methods of use thereof |
| EP2269985A3 (en) | 2004-10-25 | 2011-09-21 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| AU2006206359B2 (en) * | 2005-01-21 | 2011-03-31 | Allergan Pharmaceuticals International Limited | A tetracycline metal complex in a solid dosage form |
| WO2006084265A1 (en) | 2005-02-04 | 2006-08-10 | 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 |
| US20080241235A1 (en) * | 2007-04-02 | 2008-10-02 | 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 |
| US7919483B2 (en) * | 2005-06-24 | 2011-04-05 | Medicis Pharmaceutical Corporation | Method 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 |
| US7544373B2 (en) * | 2007-04-02 | 2009-06-09 | Medicis Pharmaceutical Corporation | Minocycline oral dosage forms for the treatment of acne |
| US7541347B2 (en) * | 2007-04-02 | 2009-06-02 | Medicis Pharmaceutical Coropration | 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 |
| EP2298324A1 (en) | 2006-01-24 | 2011-03-23 | Paratek Pharmaceuticals, Inc. | Methods of increasing oral bioavailability of tetracyclines |
| CA2649221A1 (en) * | 2006-04-17 | 2007-10-25 | Evgeny Tsiperman | Isolation of tetracycline derivatives |
| US8198470B2 (en) * | 2006-04-24 | 2012-06-12 | Teva Pharmaceutical Industries Ltd. | Crystalline form II of tigecycline and processes for preparation thereof |
| DE202007019460U1 (de) * | 2006-04-24 | 2012-10-24 | Teva Pharmaceutical Industries Ltd. | Kristalline Tigecyclin-Formen |
| AU2007249695A1 (en) * | 2006-05-15 | 2007-11-22 | 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 |
| PT2120963T (pt) | 2006-12-21 | 2018-12-17 | Paratek Pharm Innc | Compostos tetraciclina substituídos para tratamento de distúrbios inflamatórios da pele |
| PL2109602T3 (pl) * | 2006-12-21 | 2014-09-30 | Paratek Pharm Innc | Pochodne tetracyliny do leczenia zakażeń bakteryjnych, wirusowych i pasożytniczych |
| US20080241197A1 (en) * | 2007-04-02 | 2008-10-02 | Medicis Pharmaceutical Corporation | Minocycline dosage forms for the treatment of acne |
| JP2010523684A (ja) | 2007-04-12 | 2010-07-15 | 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を用いる、脊髄筋委縮症を治療するための方法 |
| JP2010525069A (ja) * | 2007-04-27 | 2010-07-22 | 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 | アミノアルキルテトラサイクリン化合物の合成方法および精製方法 |
| BRPI0823405A2 (pt) | 2007-07-06 | 2012-12-25 | Paratek Pharmaceuticals, Inc. | mÉtodos para sintetizar compostos de tetraciclina substituÍda |
| CA2717703A1 (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 |
| JP2011517697A (ja) * | 2008-04-14 | 2011-06-16 | 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 | 置換テトラサイクリン化合物 |
| 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 |
| EP2341771A4 (en) * | 2008-09-19 | 2012-08-15 | Paratek Pharm Innc | TETRACYCLINE COMPOUNDS FOR THE TREATMENT OF RHEUMATOID ARTHRITIS AND RELATED THERAPEUTIC METHODS |
| US20120121706A1 (en) | 2009-04-10 | 2012-05-17 | Tufts Medical Center, Inc. | PAR-1 Activation by Metalloproteinase-1 (MMP-1) |
| KR101799304B1 (ko) | 2010-05-12 | 2017-11-20 | 렘펙스 파머수티클스 인코퍼레이티드 | 테트라사이클린 조성물 |
| US9255068B2 (en) | 2011-05-12 | 2016-02-09 | Warner Chilcott Company, Llc | Crystalline salts of (4S,4AS,5AR,12AS)-4-dimethylamino-3,10,12,12A-tetrahydroxy-7-[methoxy(methyl)amino)-methyl] acid amide and methods of using the same |
| 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 |
| KR20170134514A (ko) | 2015-03-23 | 2017-12-06 | 바이오팜엑스 인코포레이티드 | 피부과 사용을 위한 약학 테트라사이클린 조성물 |
| 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 |
| BR112019008897A2 (pt) | 2016-11-01 | 2019-08-13 | Paratek Pharm Innc | método para tratar pneumonia bacteriana adquirida na comunidade. |
| CN111343991A (zh) | 2017-07-21 | 2020-06-26 | 阿尔米雷尔有限责任公司 | 非炎性病变的治疗 |
| 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 |
| 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 |
| NL6607516A (https=) * | 1966-05-31 | 1967-12-01 | ||
| 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. |
| US3932653A (en) * | 1974-12-19 | 1976-01-13 | Nelson Research & Development Co. | Composition and method for topical administration of griseofulvin |
| US3957994A (en) * | 1974-12-19 | 1976-05-18 | Nelson Research & Development Company | Topical anti-inflammatory composition and method of use |
| 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 US05/748,600 patent/US4086332A/en not_active Expired - Lifetime
- 1976-12-07 US US05/748,355 patent/US4081528A/en not_active Expired - Lifetime
- 1976-12-10 SE SE7613959A patent/SE435997B/xx not_active IP Right Cessation
- 1976-12-15 GB GB52394/76A patent/GB1520197A/en not_active Expired
- 1976-12-15 IN IN2209/CAL/76A patent/IN145845B/en unknown
- 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 GR GR52477A patent/GR65305B/el unknown
- 1976-12-23 CA CA268,611A patent/CA1072012A/en not_active Expired
- 1976-12-24 JP JP15613476A patent/JPS5290616A/ja active Granted
- 1976-12-27 PT PT66017A patent/PT66017B/pt unknown
- 1976-12-28 FI FI763716A patent/FI56116C/fi not_active IP Right Cessation
- 1976-12-28 CH CH1640076A patent/CH616080A5/fr not_active IP Right Cessation
- 1976-12-28 SU SU762436954A patent/SU1309901A3/ru active
- 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 NL NL7614470.A patent/NL166620C/xx 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 ZA ZA767689A patent/ZA767689B/xx unknown
- 1976-12-29 LU LU76493A patent/LU76493A1/xx unknown
- 1976-12-29 DD DD7600196699A patent/DD129997A5/xx unknown
- 1976-12-29 FR FR7639413A patent/FR2336937A1/fr active Granted
- 1976-12-29 OA OA56026A patent/OA05524A/xx unknown
- 1976-12-29 AR AR266034A patent/AR209242A1/es active
- 1976-12-29 CS CS768758A patent/CS205030B2/cs unknown
- 1976-12-29 BG BG035054A patent/BG36493A3/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 |
|---|---|---|
| CS205030B2 (en) | Method of producing of the stabil antibiotic means | |
| US4126680A (en) | Tetracycline antibiotic compositions | |
| EP1778238B1 (de) | Lagerstabile infusionslösung von dihydropteridinonen | |
| KR100402570B1 (ko) | 주사용퀴놀론제제 | |
| US4081527A (en) | Chlortetracycline compositions | |
| US20060128641A1 (en) | Levamisole, avermectins or similar in pyrrolidone solvent | |
| US4259331A (en) | Oxytetracycline compositions | |
| EP0795329B1 (en) | Parenterally injectable piroxicam solutions | |
| US4360523A (en) | Pharmaceutical formulations of 4'-(9-acridinylamino)-methanesulfon-m-anisidide | |
| US6110905A (en) | Long-acting oxytetracycline composition | |
| US5034397A (en) | Stable, water soluble salt compositions of M-AMSA in 1-methyl-2-pyrrolidinone | |
| FI57883C (fi) | Foerfarande foer framstaellning av en stabil klortetracyklinloesning | |
| JPH0112728B2 (https=) | ||
| HU176305B (hu) | Eljárás stabil tetraciklin-készítmények előállítására | |
| CA1072011A (en) | Stable solutions of tetracycline in aqueous 2-pyrrolidone |