JP2009524675A - テトラサイクリンの経口バイオアベイラビリティーを増加する方法 - Google Patents
テトラサイクリンの経口バイオアベイラビリティーを増加する方法 Download PDFInfo
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- JP2009524675A JP2009524675A JP2008552415A JP2008552415A JP2009524675A JP 2009524675 A JP2009524675 A JP 2009524675A JP 2008552415 A JP2008552415 A JP 2008552415A JP 2008552415 A JP2008552415 A JP 2008552415A JP 2009524675 A JP2009524675 A JP 2009524675A
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- Prior art keywords
- alkyl
- hydrogen
- compound
- alkenyl
- alkynyl
- 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.)
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- 239000004098 Tetracycline Substances 0.000 title claims abstract description 119
- 235000019364 tetracycline Nutrition 0.000 title claims abstract description 119
- 229930101283 tetracycline Natural products 0.000 title claims abstract description 114
- 229960002180 tetracycline Drugs 0.000 title claims abstract description 113
- 238000000034 method Methods 0.000 title claims abstract description 46
- 150000003522 tetracyclines Chemical class 0.000 title description 29
- -1 tetracycline compounds Chemical class 0.000 claims abstract description 155
- 239000003623 enhancer Substances 0.000 claims abstract description 36
- 230000001965 increasing effect Effects 0.000 claims abstract description 12
- 210000001035 gastrointestinal tract Anatomy 0.000 claims abstract description 10
- 210000000936 intestine Anatomy 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 239000003937 drug carrier Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 78
- 150000001875 compounds Chemical class 0.000 claims description 53
- 125000003342 alkenyl group Chemical group 0.000 claims description 52
- 125000000304 alkynyl group Chemical group 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 239000001257 hydrogen Substances 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 150000002431 hydrogen Chemical class 0.000 claims description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
- 125000003282 alkyl amino group Chemical group 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 125000004414 alkyl thio group Chemical group 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 25
- 125000002252 acyl group Chemical group 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 239000001301 oxygen Substances 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 239000000651 prodrug Substances 0.000 claims description 16
- 229940002612 prodrug Drugs 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 11
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 11
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000001769 aryl amino group Chemical group 0.000 claims description 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 9
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 9
- 125000005110 aryl thio group Chemical group 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 6
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 6
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 6
- 210000001198 duodenum Anatomy 0.000 claims description 6
- 239000002702 enteric coating Substances 0.000 claims description 6
- 238000009505 enteric coating Methods 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 230000001050 lubricating effect Effects 0.000 claims description 6
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 6
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 6
- 229940068968 polysorbate 80 Drugs 0.000 claims description 6
- 229920000053 polysorbate 80 Polymers 0.000 claims description 6
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
- 230000035699 permeability Effects 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 210000000813 small intestine Anatomy 0.000 claims description 5
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 4
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 4
- 125000003435 aroyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 3
- 239000003921 oil Substances 0.000 claims description 3
- 235000012239 silicon dioxide Nutrition 0.000 claims description 3
- 229910002016 Aerosil® 200 Inorganic materials 0.000 claims description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 239000001110 calcium chloride Substances 0.000 claims description 2
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 2
- 230000002708 enhancing effect Effects 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 230000003381 solubilizing effect Effects 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 8
- 230000000903 blocking effect Effects 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 14
- 239000012458 free base Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 229960004023 minocycline Drugs 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 241000700159 Rattus Species 0.000 description 10
- 125000004658 aryl carbonyl amino group Chemical group 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- 210000001519 tissue Anatomy 0.000 description 9
- 229910019142 PO4 Inorganic materials 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 125000004442 acylamino group Chemical group 0.000 description 8
- 125000004947 alkyl aryl amino group Chemical group 0.000 description 8
- 125000002877 alkyl aryl group Chemical group 0.000 description 8
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 8
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 8
- 125000004986 diarylamino group Chemical group 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 8
- 239000010452 phosphate Substances 0.000 description 8
- 150000003573 thiols Chemical class 0.000 description 8
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 description 7
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 7
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 description 7
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 7
- 150000007942 carboxylates Chemical class 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 7
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 7
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical group [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 125000004434 sulfur atom Chemical group 0.000 description 6
- 229940040944 tetracyclines Drugs 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 150000001447 alkali salts Chemical class 0.000 description 5
- 125000005907 alkyl ester group Chemical group 0.000 description 5
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 5
- 229940124530 sulfonamide Drugs 0.000 description 5
- 150000003456 sulfonamides Chemical group 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
- 230000003000 nontoxic effect Effects 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- FIWQZURFGYXCEO-UHFFFAOYSA-M sodium;decanoate Chemical compound [Na+].CCCCCCCCCC([O-])=O FIWQZURFGYXCEO-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004100 Oxytetracycline Substances 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
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- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
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- 150000001412 amines Chemical class 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 229960000625 oxytetracycline Drugs 0.000 description 3
- IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 description 3
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- 229910052623 talc Inorganic materials 0.000 description 3
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 3
- NWXMGUDVXFXRIG-WESIUVDSSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical 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 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
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- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
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- 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
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
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- 108010010803 Gelatin Proteins 0.000 description 2
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000005090 alkenylcarbonyl group Chemical group 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
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- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 description 2
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- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
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- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
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- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76181906P | 2006-01-24 | 2006-01-24 | |
| PCT/US2007/002081 WO2007087416A2 (en) | 2006-01-24 | 2007-01-24 | Methods of increasing oral bioavailability of tetracyclines |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2010013625A Division JP2010106043A (ja) | 2006-01-24 | 2010-01-25 | テトラサイクリンの経口バイオアベイラビリティーを増加する方法 |
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| JP2009524675A true JP2009524675A (ja) | 2009-07-02 |
| JP2009524675A5 JP2009524675A5 (enExample) | 2010-03-18 |
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| JP2008552415A Pending JP2009524675A (ja) | 2006-01-24 | 2007-01-24 | テトラサイクリンの経口バイオアベイラビリティーを増加する方法 |
| JP2010013625A Pending JP2010106043A (ja) | 2006-01-24 | 2010-01-25 | テトラサイクリンの経口バイオアベイラビリティーを増加する方法 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2010013625A Pending JP2010106043A (ja) | 2006-01-24 | 2010-01-25 | テトラサイクリンの経口バイオアベイラビリティーを増加する方法 |
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| EP (2) | EP1991236A2 (enExample) |
| JP (2) | JP2009524675A (enExample) |
| AU (2) | AU2007208214B2 (enExample) |
| CA (1) | CA2639406A1 (enExample) |
| WO (1) | WO2007087416A2 (enExample) |
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| PT2271348T (pt) * | 2008-03-28 | 2018-04-16 | Paratek Pharm Innc | Formulação de comprimido oral de composto de tetraciclina |
| CA2721399A1 (en) * | 2008-04-14 | 2009-10-22 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
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| ES2627772T3 (es) | 2009-05-08 | 2017-07-31 | Tetraphase Pharmaceuticals, Inc. | Compuestos de tetraciclina |
| JP5944825B2 (ja) | 2009-08-28 | 2016-07-05 | テトラフェース 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 |
| US9119793B1 (en) | 2011-06-28 | 2015-09-01 | Medicis Pharmaceutical Corporation | Gastroretentive dosage forms for doxycycline |
| WO2013088255A1 (en) * | 2011-12-15 | 2013-06-20 | Alkermes Pharma Ireland Limited | Prodrugs of secondary amine compounds |
| BR112015004523B1 (pt) | 2012-08-31 | 2020-08-04 | Tetraphase Pharmaceuticals, Inc | Compostos de tetraciclina, composições farmacêuticas e seus usos |
| US10842802B2 (en) | 2013-03-15 | 2020-11-24 | Medicis Pharmaceutical Corporation | Controlled release pharmaceutical dosage forms |
| SG11201808246SA (en) * | 2016-03-24 | 2018-10-30 | Paratek Pharm Innc | Methods for treating and preventing c. difficile infection |
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2007087416A3 (en) | 2007-09-20 |
| US20080070873A1 (en) | 2008-03-20 |
| WO2007087416A2 (en) | 2007-08-02 |
| JP2010106043A (ja) | 2010-05-13 |
| CA2639406A1 (en) | 2007-08-02 |
| AU2007208214B2 (en) | 2013-02-14 |
| EP1991236A2 (en) | 2008-11-19 |
| EP2298324A1 (en) | 2011-03-23 |
| AU2007208214A1 (en) | 2007-08-02 |
| US20160030453A1 (en) | 2016-02-04 |
| US9078811B2 (en) | 2015-07-14 |
| AU2010236028A1 (en) | 2010-11-18 |
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