DE69221252T2 - Lipophile Zusammensetzungen von Oligosaccharid-Antibiotikasalzen - Google Patents
Lipophile Zusammensetzungen von Oligosaccharid-AntibiotikasalzenInfo
- Publication number
- DE69221252T2 DE69221252T2 DE69221252T DE69221252T DE69221252T2 DE 69221252 T2 DE69221252 T2 DE 69221252T2 DE 69221252 T DE69221252 T DE 69221252T DE 69221252 T DE69221252 T DE 69221252T DE 69221252 T2 DE69221252 T2 DE 69221252T2
- Authority
- DE
- Germany
- Prior art keywords
- cyclodextrin
- hydroxypropyl
- formula
- compound
- pharmaceutically acceptable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 230000003115 biocidal effect Effects 0.000 title claims abstract description 75
- 239000000203 mixture Substances 0.000 title claims abstract description 65
- 229920001542 oligosaccharide Polymers 0.000 title claims abstract description 55
- 150000002482 oligosaccharides Chemical class 0.000 title claims abstract description 55
- 150000003839 salts Chemical class 0.000 title claims description 22
- 208000011580 syndromic disease Diseases 0.000 claims abstract description 38
- 206010067484 Adverse reaction Diseases 0.000 claims abstract description 34
- 230000006838 adverse reaction Effects 0.000 claims abstract description 34
- 241001465754 Metazoa Species 0.000 claims abstract description 26
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 13
- 230000002924 anti-infective effect Effects 0.000 claims abstract 2
- 229920000858 Cyclodextrin Polymers 0.000 claims description 99
- 150000001875 compounds Chemical class 0.000 claims description 71
- -1 hydroxypropyl substituents Chemical group 0.000 claims description 51
- 239000003242 anti bacterial agent Substances 0.000 claims description 44
- 229940088710 antibiotic agent Drugs 0.000 claims description 40
- 229940080345 gamma-cyclodextrin Drugs 0.000 claims description 32
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 claims description 29
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 24
- 229960004853 betadex Drugs 0.000 claims description 22
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 17
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims description 16
- 229930188253 Everninomicin Natural products 0.000 claims description 15
- 229940043377 alpha-cyclodextrin Drugs 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 210000002966 serum Anatomy 0.000 claims description 13
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims description 10
- 208000027096 gram-negative bacterial infections Diseases 0.000 claims description 9
- 208000027136 gram-positive bacterial infections Diseases 0.000 claims description 9
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 208000015181 infectious disease Diseases 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 6
- 238000002560 therapeutic procedure Methods 0.000 claims description 6
- 229930192734 Avilamycin Natural products 0.000 claims description 5
- IHGNORNGVOUHBM-UHFFFAOYSA-N Flambamycin Natural products COCC1OC(OC2C(C3OC4(OC3CO2)C2OCOC2C(O)(C(C)O4)C(C)=O)OC(=O)C(C)C)C(OC)C(O)C1OC(C1O)OC(C)C(OC)C1OC(C(C1(C)O2)O)OC(C)C1OC2(OC1C)CC(O)C1OC(OC1C)CC(O)C1OC(=O)C1=C(C)C(Cl)=C(O)C(Cl)=C1OC IHGNORNGVOUHBM-UHFFFAOYSA-N 0.000 claims description 5
- ATJWHTJURZPAPG-CFNSFCSXSA-N [(1r,2r,4r,6s)-4-[(2r,2'r,3's,3ar,4r,4'r,6s,7s,7ar)-6-[(2r,3r,4r,5r,6s)-2-[(2r,3s,4s,5s,6s)-6-[(2r,3as,3'ar,6s,6'r,7r,7's,7ar,7'ar)-7'-acetyl-7'-hydroxy-6'-methyl-7-(2-methylpropanoyloxy)spiro[4,6,7,7a-tetrahydro-3ah-[1,3]dioxolo[4,5-c]pyran-2,4'-6,7a-dih Chemical compound O([C@@H]1[C@@H](C)C[C@H](C[C@H]1O)O[C@H]1[C@H](O)C[C@]2(O[C@@H]3[C@@H](C)O[C@H]([C@H]([C@@]3(C)O2)O)O[C@H]2[C@@H](OC)[C@@H](O)O[C@H]([C@@H]2O)O[C@H]2[C@H](O)[C@H](OC)[C@H](O[C@H]3[C@@H]([C@@H]4O[C@]5(O[C@H]4CO3)[C@@H]3OCO[C@H]3[C@@](O)([C@@H](C)O5)C(C)=O)OC(=O)C(C)C)O[C@@H]2COC)O[C@@H]1C)C(=O)C1=C(C)C(Cl)=C(O)C(Cl)=C1OC ATJWHTJURZPAPG-CFNSFCSXSA-N 0.000 claims description 5
- 235000019379 avilamycin Nutrition 0.000 claims description 5
- 239000004190 Avilamycin Substances 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- XIRGHRXBGGPPKY-OTPQUNEMSA-N [(2r,3s,4r,6s)-6-[(2'r,3's,3ar,4r,4'r,6s,7ar)-6-[(2s,3r,4r,5s,6r)-2-[(2r,3s,4s,5s,6s)-6-[(2r,3as,3'ar,6'r,7r,7's,7ar,7'ar)-7'-acetyl-7'-hydroxy-6'-methyl-7-(2-methylpropanoyloxy)spiro[4,6,7,7a-tetrahydro-3ah-[1,3]dioxolo[4,5-c]pyran-2,4'-6,7a-dihydro-3ah- Chemical compound O([C@H]1[C@H](O)C[C@@H](O[C@@H]1C)O[C@H]1[C@H](O)CC2(O[C@]3(C)C[C@@H](O[C@H](C)[C@H]3O2)O[C@H]2[C@@H](OC)[C@@H](C)O[C@H]([C@@H]2O)O[C@H]2[C@H](O)[C@H](OC)[C@H](OC3[C@@H]([C@@H]4O[C@]5(O[C@H]4CO3)[C@@H]3OCO[C@H]3[C@@](O)([C@@H](C)O5)C(C)=O)OC(=O)C(C)C)O[C@@H]2COC)O[C@@H]1C)C(=O)C1=C(C)C(Cl)=C(O)C(Cl)=C1OC XIRGHRXBGGPPKY-OTPQUNEMSA-N 0.000 claims description 4
- 229960005185 avilamycin Drugs 0.000 claims description 4
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical group OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 3
- 229930192609 Curamycin Natural products 0.000 claims description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 3
- 229930195725 Mannitol Natural products 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 3
- 239000000594 mannitol Substances 0.000 claims description 3
- 235000010355 mannitol Nutrition 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 claims description 2
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 claims description 2
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 2
- MSWZFWKMSRAUBD-QZABAPFNSA-N beta-D-glucosamine Chemical compound N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-QZABAPFNSA-N 0.000 claims description 2
- VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical group CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 claims description 2
- 229960002023 chloroprocaine Drugs 0.000 claims description 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 2
- 229960001231 choline Drugs 0.000 claims description 2
- CJXAEXPPLWQRFR-UHFFFAOYSA-N clemizole Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2N=C1CN1CCCC1 CJXAEXPPLWQRFR-UHFFFAOYSA-N 0.000 claims description 2
- 229950002020 clemizole Drugs 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 229940043279 diisopropylamine Drugs 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229960005141 piperazine Drugs 0.000 claims description 2
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 claims description 2
- 229960004919 procaine Drugs 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 21
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 abstract description 16
- 229920000053 polysorbate 80 Polymers 0.000 abstract description 16
- 239000003814 drug Substances 0.000 abstract description 6
- 241000282414 Homo sapiens Species 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 5
- 208000035143 Bacterial infection Diseases 0.000 abstract description 4
- 208000022362 bacterial infectious disease Diseases 0.000 abstract description 4
- ODLHGICHYURWBS-FOSILIAISA-N molport-023-220-444 Chemical compound CC(O)COC[C@@H]([C@@H]([C@H]([C@@H]1O)O)O[C@@H]2O[C@H]([C@H](O[C@@H]3O[C@@H](COCC(C)O)[C@@H]([C@H]([C@@H]3O)O)O[C@@H]3O[C@@H](COCC(C)O)[C@@H]([C@H]([C@@H]3O)O)O[C@@H]3O[C@@H](COCC(C)O)[C@@H]([C@H]([C@@H]3O)O)O[C@@H]3O[C@@H](COCC(C)O)[C@@H]([C@H]([C@@H]3O)O)O3)[C@@H](O)[C@@H]2O)COCC(O)C)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O)[C@H]3O[C@H]1COCC(C)O ODLHGICHYURWBS-FOSILIAISA-N 0.000 abstract 1
- 239000002585 base Substances 0.000 description 32
- 238000000855 fermentation Methods 0.000 description 28
- 230000004151 fermentation Effects 0.000 description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 26
- 239000007864 aqueous solution Substances 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 235000002639 sodium chloride Nutrition 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 241000699670 Mus sp. Species 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical group OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 11
- 238000002347 injection Methods 0.000 description 11
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- 239000000243 solution Substances 0.000 description 11
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- UPADRKHAIMTUCC-OWALTSPQSA-N [(2r,3r,4r,6s)-6-[(2r,2'r,3's,3ar,4r,4'r,6s,7s,7ar)-6-[(2s,3r,4r,5s,6r)-2-[(2r,3s,4s,5s,6s)-6-[(3ar,3'as,4r,6's,7r,7'r,7as,7'as)-7-(2,4-dihydroxy-6-methylbenzoyl)oxy-7'-hydroxyspiro[3a,6,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4,2'-4,6,7,7a-tetrahydro-3a Chemical compound O([C@@H]1CO[C@]2([C@@H]3OCO[C@H]31)O[C@H]1CO[C@H]([C@@H]([C@@H]1O2)O)O[C@@H]1O[C@@H]([C@H]([C@H](O)[C@@H]1OC)O[C@H]1[C@@H]([C@@H](O[C@H]2[C@H]([C@@]3(C)O[C@]4(O[C@H](C)[C@@H](O[C@@H]5O[C@H](C)[C@@H](OC(=O)C=6C(=C(Cl)C(O)=C(Cl)C=6C)OC)[C@H](O[C@@H]6O[C@@H](C)[C@H](OC)[C@](C)(C6)[N+]([O-])=O)C5)[C@H](O)C4)O[C@@H]3[C@@H](C)O2)O)[C@@H](OC)[C@@H](C)O1)O)COC)C(=O)C1=C(C)C=C(O)C=C1O UPADRKHAIMTUCC-OWALTSPQSA-N 0.000 description 9
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- FZWBNHMXJMCXLU-UHFFFAOYSA-N 2,3,4,5-tetrahydroxy-6-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyhexanal Chemical compound OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OCC(O)C(O)C(O)C(O)C=O)O1 FZWBNHMXJMCXLU-UHFFFAOYSA-N 0.000 description 5
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- 229960005156 digoxin Drugs 0.000 description 1
- LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
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- 229940032049 enterococcus faecalis Drugs 0.000 description 1
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- 101150071520 gmm gene Proteins 0.000 description 1
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- 210000003141 lower extremity Anatomy 0.000 description 1
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- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
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- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
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- 238000005497 microtitration Methods 0.000 description 1
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- 238000010172 mouse model Methods 0.000 description 1
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- 230000035772 mutation Effects 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
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- 150000002989 phenols Chemical class 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
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 201000000317 pneumocystosis Diseases 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
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- 239000003755 preservative agent Substances 0.000 description 1
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- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
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- 239000008223 sterile water Substances 0.000 description 1
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
-
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
- C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
- C07H9/04—Cyclic acetals
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nanotechnology (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Medical Informatics (AREA)
- Biophysics (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicinal Preparation (AREA)
- Steroid Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77786491A | 1991-10-16 | 1991-10-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69221252D1 DE69221252D1 (de) | 1997-09-04 |
| DE69221252T2 true DE69221252T2 (de) | 1998-01-22 |
Family
ID=25111545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69221252T Expired - Fee Related DE69221252T2 (de) | 1991-10-16 | 1992-10-14 | Lipophile Zusammensetzungen von Oligosaccharid-Antibiotikasalzen |
Country Status (26)
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6380172B1 (en) | 1991-10-16 | 2002-04-30 | Schering Corporation | Monomeric lipophilic oligosaccharide antibiotic compositions |
| US5948688A (en) * | 1991-10-16 | 1999-09-07 | Schering Corporation | Method of determining monomeric drug content |
| US5652226A (en) * | 1995-12-22 | 1997-07-29 | Schering Corporation | Water soluble antibiotics |
| US5776912A (en) * | 1996-12-20 | 1998-07-07 | Schering Corporation | Lipophilic oligosaccharide antibiotic compositions |
| US5763600A (en) * | 1997-04-18 | 1998-06-09 | Schering Corporation | Oligosaccharide antibiotics and process for preparation thereof |
| EP1027061B1 (en) * | 1997-10-03 | 2005-05-25 | Galenica Pharmaceuticals, Inc. | Imine-forming polysaccharides, preparation thereof and the use thereof as adjuvants and immunostimulants |
| US6162910A (en) * | 1998-11-30 | 2000-12-19 | Schering Corporation | Process for preparing lipophilic oligosaccharide antibiotics |
| AR021717A1 (es) * | 1998-12-18 | 2002-07-31 | Schering Corp | Proceso para recuperar antibioticos oligosacaridos lipofilicos. |
| US6320044B1 (en) | 1998-12-18 | 2001-11-20 | Schering Corporation | Process for recovering lipophilic oligosaccharide antibiotics |
| WO2001039573A2 (de) * | 1999-12-01 | 2001-06-07 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Verwendung von lungensurfactant zur behandlung von legionärskrankheit |
| US6861513B2 (en) | 2000-01-12 | 2005-03-01 | Schering Corporation | Everninomicin biosynthetic genes |
| SI1278549T1 (sl) | 2000-05-02 | 2009-04-30 | Theravance Inc | Sestavek, ki vsebuje ciklodekstrin in glikopeptidni antibiotik |
| US6699505B2 (en) * | 2000-10-17 | 2004-03-02 | Massachusetts Institute Of Technology | Method of increasing the efficacy of antibiotics by compexing with cyclodextrins |
| DE10109166A1 (de) * | 2001-02-25 | 2002-09-12 | Combinature Biopharm Ag | Avilamycin-Derivate |
| MXPA06010592A (es) * | 2004-03-17 | 2007-06-12 | Panacos Pharmaceuticals Inc | Sales farmaceuticas de acido 3-o-(3',3'-dimetilsuccinil) betulinico. |
| EP1977874A3 (en) * | 2004-12-01 | 2008-10-15 | Nitto Denko Corporation | Foam Filling Member |
| JP2008535923A (ja) * | 2005-04-12 | 2008-09-04 | パナコス ファーマシューティカルズ インコーポレーティッド | ３−ｏ−（３’，３’−ジメチルスクシニル）ベツリン酸ジ−ｎ−メチル−ｄ−グルカミンの多形 |
| BRPI0816790A8 (pt) * | 2007-09-14 | 2017-05-16 | Sanofi Pasteur Biologics Co | Composições farmacêuticas contendo toxóides a e b de clostridium difficile |
| JP2010095454A (ja) * | 2008-10-14 | 2010-04-30 | Cyclochem:Kk | 抗菌組成物 |
| EP4324483A3 (en) * | 2011-01-14 | 2024-05-01 | Emory University | Oligosaccharide conjugates for targeting bacteria and uses related thereto |
| EA033892B1 (ru) | 2015-06-10 | 2019-12-05 | Втесс, Инк. | Композиции гидроксипропил-бета-циклодекстринов и способы |
| CN106317143B (zh) * | 2016-08-23 | 2020-10-30 | 河北圣雪大成制药有限责任公司 | 一种提取阿维拉霉素的方法 |
| WO2023156966A1 (en) | 2022-02-18 | 2023-08-24 | Beren Therapeutics P.B.C. | Compositions of hydroxypropyl-beta-cyclodextrin and methods of purifying the same |
| CN117024611B (zh) * | 2023-03-01 | 2024-05-17 | 中国科学院南海海洋研究所 | 寡糖类抗生素everninomicin高产菌株的构建及活性的应用 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR128F (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1962-04-02 | |||
| US3915956A (en) * | 1973-07-09 | 1975-10-28 | Schering Corp | Reduction products of everninomicins and methods for their manufacture |
| US3920629A (en) * | 1973-09-19 | 1975-11-18 | Schering Corp | Desevernitrose everninomicins and method for their manufacture |
| US4006225A (en) * | 1973-10-31 | 1977-02-01 | Schering Corporation | Method of using reduction products of everninomicins as antibacterial agents and pharmaceutical compositions useful therefor |
| US3998708A (en) * | 1976-01-19 | 1976-12-21 | Schering Corporation | Electrochemical process for preparing hydroxylaminoeverninomicins |
| US4027016A (en) * | 1976-01-19 | 1977-05-31 | Schering Corporation | Everninomicin antibacterial derivatives, electrochemical method for their manufacture, method for their use as antibacterial agents, and pharmaceutical compositions useful therefor |
| US4129720A (en) * | 1977-02-14 | 1978-12-12 | Schering Corporation | Aminoeverninomicin and derivatives thereof |
| US4597968A (en) * | 1982-08-06 | 1986-07-01 | Schering Corporation | Antibiotic 13-384 complex from Micromonospora carbonacea var africana |
| DE3346123A1 (de) * | 1983-12-21 | 1985-06-27 | Janssen Pharmaceutica, N.V., Beerse | Pharmazeutische praeparate von in wasser schwerloeslichen oder instabilen arzneistoffen und verfahren zu ihrer herstellung |
| US4596795A (en) * | 1984-04-25 | 1986-06-24 | The United States Of America As Represented By The Secretary, Dept. Of Health & Human Services | Administration of sex hormones in the form of hydrophilic cyclodextrin derivatives |
| US4727064A (en) * | 1984-04-25 | 1988-02-23 | The United States Of America As Represented By The Department Of Health And Human Services | Pharmaceutical preparations containing cyclodextrin derivatives |
| US4735903A (en) * | 1984-06-21 | 1988-04-05 | Schering Corporation | Micromonospora carbonacea var africana |
| US4870060A (en) * | 1985-03-15 | 1989-09-26 | Janssen Pharmaceutica | Derivatives of γ-cylodextrin |
| US4767748A (en) * | 1985-10-15 | 1988-07-30 | Schering Corporation | Substituted oligosaccharide antibodies |
| US4622314A (en) * | 1985-10-15 | 1986-11-11 | Schering Corporation | Substituted oligosaccharide antibiotics |
| US5002935A (en) * | 1987-12-30 | 1991-03-26 | University Of Florida | Improvements in redox systems for brain-targeted drug delivery |
| US5017566A (en) * | 1987-12-30 | 1991-05-21 | University Of Florida | Redox systems for brain-targeted drug delivery |
| KR0166088B1 (ko) * | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
-
1992
- 1992-10-14 AT AT92309368T patent/ATE156019T1/de not_active IP Right Cessation
- 1992-10-14 DK DK92309368.6T patent/DK0538011T3/da active
- 1992-10-14 EP EP92921991A patent/EP0610295A1/en active Pending
- 1992-10-14 ES ES92309368T patent/ES2104845T3/es not_active Expired - Lifetime
- 1992-10-14 KR KR1019940701247A patent/KR100249584B1/ko not_active Expired - Fee Related
- 1992-10-14 DE DE69221252T patent/DE69221252T2/de not_active Expired - Fee Related
- 1992-10-14 JP JP5507719A patent/JP2614407B2/ja not_active Expired - Lifetime
- 1992-10-14 PH PH45109A patent/PH31675A/en unknown
- 1992-10-14 NZ NZ244735A patent/NZ244735A/en unknown
- 1992-10-14 ZA ZA927923A patent/ZA927923B/xx unknown
- 1992-10-14 US US08/211,700 patent/US5624914A/en not_active Expired - Lifetime
- 1992-10-14 CA CA002121345A patent/CA2121345C/en not_active Expired - Fee Related
- 1992-10-14 AU AU27806/92A patent/AU678344B2/en not_active Ceased
- 1992-10-14 EP EP92309368A patent/EP0538011B1/en not_active Expired - Lifetime
- 1992-10-14 YU YU92192A patent/YU48722B/sh unknown
- 1992-10-14 PL PL92303189A patent/PL170591B1/pl unknown
- 1992-10-14 WO PCT/US1992/008565 patent/WO1993007904A1/en not_active Application Discontinuation
- 1992-10-14 HU HU9401104A patent/HUT75157A/hu unknown
- 1992-10-14 TW TW081108170A patent/TW221378B/zh active
- 1992-10-15 CN CN92112388A patent/CN1035923C/zh not_active Expired - Fee Related
- 1992-10-15 IL IL10344692A patent/IL103446A/xx not_active IP Right Cessation
- 1992-10-15 MX MX9205922A patent/MX9205922A/es not_active IP Right Cessation
- 1992-10-16 SI SI19929200260A patent/SI9200260A/sl unknown
- 1992-10-16 HR HR07/777,864A patent/HRP921069B1/xx not_active IP Right Cessation
-
1994
- 1994-04-08 NO NO941276A patent/NO307326B1/no not_active IP Right Cessation
- 1994-04-14 FI FI941723A patent/FI941723A7/fi unknown
-
1997
- 1997-09-19 GR GR970402434T patent/GR3024800T3/el unknown
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