CA2639406A1 - Methods of increasing oral bioavailability of tetracyclines - Google Patents
Methods of increasing oral bioavailability of tetracyclines Download PDFInfo
- Publication number
- CA2639406A1 CA2639406A1 CA002639406A CA2639406A CA2639406A1 CA 2639406 A1 CA2639406 A1 CA 2639406A1 CA 002639406 A CA002639406 A CA 002639406A CA 2639406 A CA2639406 A CA 2639406A CA 2639406 A1 CA2639406 A1 CA 2639406A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- hydrogen
- alkenyl
- aryl
- 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.)
- Abandoned
Links
- 239000004098 Tetracycline Substances 0.000 title claims abstract description 129
- 235000019364 tetracycline Nutrition 0.000 title claims abstract description 128
- 238000000034 method Methods 0.000 title claims abstract description 44
- 230000001965 increasing effect Effects 0.000 title claims abstract description 13
- 150000003522 tetracyclines Chemical class 0.000 title description 39
- 229940040944 tetracyclines Drugs 0.000 title description 32
- -1 tetracycline compounds Chemical class 0.000 claims abstract description 164
- 229930101283 tetracycline Natural products 0.000 claims abstract description 98
- 229960002180 tetracycline Drugs 0.000 claims abstract description 97
- 125000000217 alkyl group Chemical group 0.000 claims description 76
- 125000003118 aryl group Chemical group 0.000 claims description 53
- 125000003342 alkenyl group Chemical group 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 52
- 125000000304 alkynyl group Chemical group 0.000 claims description 51
- 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
- 239000003795 chemical substances by application Substances 0.000 claims description 37
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
- 230000002708 enhancing effect Effects 0.000 claims description 34
- 150000002431 hydrogen Chemical group 0.000 claims description 30
- 125000003282 alkyl amino group Chemical group 0.000 claims description 29
- 229910052736 halogen Chemical group 0.000 claims description 29
- 150000002367 halogens Chemical group 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000004414 alkyl thio group Chemical group 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 239000001301 oxygen Substances 0.000 claims description 22
- 125000002252 acyl group Chemical group 0.000 claims description 21
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 21
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 239000000651 prodrug Chemical group 0.000 claims description 16
- 229940002612 prodrug Drugs 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 12
- 229920000053 polysorbate 80 Polymers 0.000 claims description 12
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 11
- 125000005199 aryl carbonyloxy group Chemical group 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 10
- 229940068968 polysorbate 80 Drugs 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 125000004457 alkyl amino carbonyl 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
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 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
- 239000003937 drug carrier Substances 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
- 230000035699 permeability Effects 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
- 239000003921 oil Substances 0.000 claims description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 4
- 125000003368 amide 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
- 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
- 235000012239 silicon dioxide Nutrition 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
- 230000002183 duodenal effect Effects 0.000 claims description 3
- 230000002496 gastric effect Effects 0.000 claims description 3
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 230000000873 masking effect Effects 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 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 group [H]S* 0.000 claims 8
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 239000012458 free base Substances 0.000 description 32
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 14
- 229960004023 minocycline Drugs 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 241000700159 Rattus Species 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 125000004658 aryl carbonyl amino group Chemical group 0.000 description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 229910019142 PO4 Inorganic materials 0.000 description 9
- 125000004442 acylamino group Chemical group 0.000 description 9
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 9
- 239000010452 phosphate Substances 0.000 description 9
- 210000001519 tissue Anatomy 0.000 description 9
- 239000002253 acid Substances 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
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 125000004986 diarylamino group Chemical group 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 150000003573 thiols Chemical class 0.000 description 8
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 description 7
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 description 7
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 7
- 150000007942 carboxylates Chemical class 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 7
- 150000003467 sulfuric acid derivatives Chemical group 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000004434 sulfur atom Chemical group 0.000 description 6
- 241000581364 Clinitrachus argentatus Species 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 5
- 125000005907 alkyl ester group Chemical group 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 5
- 230000006870 function Effects 0.000 description 5
- 210000004731 jugular vein Anatomy 0.000 description 5
- 239000000314 lubricant Substances 0.000 description 5
- 238000003305 oral gavage Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229920001661 Chitosan Polymers 0.000 description 4
- 241001465754 Metazoa Species 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
- 238000001727 in vivo Methods 0.000 description 4
- 238000001990 intravenous administration Methods 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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
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- 235000019198 oils Nutrition 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- FIWQZURFGYXCEO-UHFFFAOYSA-M sodium;decanoate Chemical compound [Na+].CCCCCCCCCC([O-])=O FIWQZURFGYXCEO-UHFFFAOYSA-M 0.000 description 4
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- 239000003814 drug Substances 0.000 description 3
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- 150000003840 hydrochlorides Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 description 2
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- 125000004429 atom Chemical group 0.000 description 2
- 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
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- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Molecular Biology (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76181906P | 2006-01-24 | 2006-01-24 | |
| US60/761,819 | 2006-01-24 | ||
| PCT/US2007/002081 WO2007087416A2 (en) | 2006-01-24 | 2007-01-24 | Methods of increasing oral bioavailability of tetracyclines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2639406A1 true CA2639406A1 (en) | 2007-08-02 |
Family
ID=38181071
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002639406A Abandoned CA2639406A1 (en) | 2006-01-24 | 2007-01-24 | Methods of increasing oral bioavailability of tetracyclines |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US9078811B2 (enExample) |
| EP (2) | EP1991236A2 (enExample) |
| JP (2) | JP2009524675A (enExample) |
| AU (2) | AU2007208214B2 (enExample) |
| CA (1) | CA2639406A1 (enExample) |
| WO (1) | WO2007087416A2 (enExample) |
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| US20040224927A1 (en) * | 2000-06-16 | 2004-11-11 | Trustees Of Tufts College | 7-N-substituted phenyl tetracycline compounds |
| US7094806B2 (en) * | 2000-07-07 | 2006-08-22 | Trustees Of Tufts College | 7, 8 and 9-substituted tetracycline compounds |
| US8088820B2 (en) * | 2001-04-24 | 2012-01-03 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds for the treatment of malaria |
| US20060287283A1 (en) * | 2003-07-09 | 2006-12-21 | Paratek Pharmaceuticals, Inc. | Prodrugs of 9-aminomethyl tetracycline compounds |
| EP2319828A3 (en) | 2003-07-09 | 2011-07-06 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| AU2004261143B2 (en) | 2003-07-25 | 2009-11-05 | Allergan Pharmaceuticals International Limited | A doxycycline metal complex in a solid dosage form |
| EP2287148A3 (en) * | 2004-10-25 | 2011-10-26 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| NZ556582A (en) * | 2005-01-21 | 2010-12-24 | Warner Chilcott Co Llc | A tetracycline metal complex in a solid dosage form |
| JP2008530023A (ja) * | 2005-02-04 | 2008-08-07 | 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 | テトラサイクリン化合物の１１ａ，１２−誘導体 |
| WO2007014154A2 (en) * | 2005-07-21 | 2007-02-01 | Paratek Pharmaceuticals, Inc. | 10-substituted tetracyclines and methods of use thereof |
| 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 |
| SI2120963T1 (sl) | 2006-12-21 | 2019-02-28 | Paratek Pharmaceuticals, Inc. | Substituirane spojine tetraciklina za zdravljenje vnetnih kožnih motenj |
| PT2109602E (pt) * | 2006-12-21 | 2014-05-23 | Paratek Pharm Innc | Derivados de tetraciclina para o tratamento de infecções bacterianas, virais e parasitárias |
| US7935687B2 (en) | 2007-04-12 | 2011-05-03 | Paratek Pharmaceuticals, Inc. | Methods for treating spinal muscular atrophy using tetracycline compounds |
| CN102015602A (zh) | 2008-03-05 | 2011-04-13 | 帕拉特克药品公司 | 米诺环素化合物及其使用方法 |
| PT2271348T (pt) * | 2008-03-28 | 2018-04-16 | Paratek Pharm Innc | Formulação de comprimido oral de composto de tetraciclina |
| US20100022483A1 (en) * | 2008-04-14 | 2010-01-28 | Paratek Pharmaceuticals, Inc. | Substituted Tetracycline Compounds |
| TW202021946A (zh) * | 2008-05-19 | 2020-06-16 | 美商派洛泰克藥物股份有限公司 | 四環素化合物之甲苯磺酸鹽及同素異形體 |
| CN103936645B (zh) | 2008-08-08 | 2016-03-09 | 四相制药公司 | C7-氟取代的四环素化合物 |
| AP2011005631A0 (en) * | 2008-09-19 | 2011-04-30 | Paratek Pharmaceuticals Ind | Tetracycline compounds for the treatment of rheumatoid arthritis and related methods of treatment. |
| CA2761241C (en) | 2009-05-08 | 2018-02-27 | Tetraphase Pharmaceuticals, Inc. | Tetracycline compounds |
| US9624166B2 (en) | 2009-08-28 | 2017-04-18 | Tetraphase Pharmaceuticals, Inc. | Tetracycline compounds |
| US9119793B1 (en) | 2011-06-28 | 2015-09-01 | Medicis Pharmaceutical Corporation | Gastroretentive dosage forms for doxycycline |
| NZ722096A (en) | 2011-12-15 | 2016-11-25 | Alkermes Pharma Ireland Ltd | Prodrugs of secondary amine compounds |
| HUE042600T2 (hu) | 2012-08-31 | 2019-07-29 | Tetraphase Pharmaceuticals Inc | Tetraciklin vegyületek |
| US10842802B2 (en) | 2013-03-15 | 2020-11-24 | Medicis Pharmaceutical Corporation | Controlled release pharmaceutical dosage forms |
| SG10201913559VA (en) * | 2016-03-24 | 2020-02-27 | Paratek Pharm Innc | Methods for treating and preventing c. difficile infection |
| EP3529236B1 (en) | 2016-10-19 | 2024-02-07 | Tetraphase Pharmaceuticals, Inc. | Crystalline forms of eravacycline |
| CN110087655A (zh) | 2016-11-01 | 2019-08-02 | 帕拉特克药品公司 | 9-氨基甲基米诺环素化合物及其在治疗社区获得性细菌性肺炎(cabp)中的用途 |
| PT117254B (pt) | 2021-05-26 | 2024-04-18 | Hovione Farm S A | Método de síntese de compostos 9-aminometil tetraciclinas |
| WO2023238143A1 (en) * | 2022-06-11 | 2023-12-14 | Gufic Biosciences Limited | A freeze dried parenteral composition of omadacycline tosylate with improved stability |
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| EA006170B1 (ru) * | 2000-07-07 | 2005-10-27 | Трастис Оф Тафтс Коллидж | Замещенные соединения тетрациклина (варианты), фармацевтическая композиция и способ лечения чувствительного к тетрациклину состояния субъекта |
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| CA2531732C (en) * | 2003-07-09 | 2012-04-10 | Paratek Pharmaceuticals, Inc. | Prodrugs of 9-aminomethyl tetracycline compounds |
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| WO2005016311A1 (en) * | 2003-08-11 | 2005-02-24 | Advancis Pharmaceutical Corporation | Robust pellet |
| WO2005046651A1 (en) * | 2003-11-12 | 2005-05-26 | Ranbaxy Laboratories Limited | Liquid filled capsules of doxycycline |
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-
2007
- 2007-01-24 EP EP07762567A patent/EP1991236A2/en not_active Withdrawn
- 2007-01-24 WO PCT/US2007/002081 patent/WO2007087416A2/en not_active Ceased
- 2007-01-24 EP EP10192776A patent/EP2298324A1/en not_active Withdrawn
- 2007-01-24 US US11/657,412 patent/US9078811B2/en active Active
- 2007-01-24 CA CA002639406A patent/CA2639406A1/en not_active Abandoned
- 2007-01-24 AU AU2007208214A patent/AU2007208214B2/en not_active Expired - Fee Related
- 2007-01-24 JP JP2008552415A patent/JP2009524675A/ja active Pending
-
2010
- 2010-01-25 JP JP2010013625A patent/JP2010106043A/ja active Pending
- 2010-10-26 AU AU2010236028A patent/AU2010236028A1/en not_active Abandoned
-
2015
- 2015-07-01 US US14/789,506 patent/US20160030453A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010106043A (ja) | 2010-05-13 |
| WO2007087416A3 (en) | 2007-09-20 |
| AU2010236028A1 (en) | 2010-11-18 |
| US9078811B2 (en) | 2015-07-14 |
| JP2009524675A (ja) | 2009-07-02 |
| AU2007208214A1 (en) | 2007-08-02 |
| US20160030453A1 (en) | 2016-02-04 |
| EP2298324A1 (en) | 2011-03-23 |
| US20080070873A1 (en) | 2008-03-20 |
| WO2007087416A2 (en) | 2007-08-02 |
| EP1991236A2 (en) | 2008-11-19 |
| AU2007208214B2 (en) | 2013-02-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20140716 |