AU2006339058B2 - Phosphonated rifamycins and uses thereof for the prevention and treatment of bone and joint infections - Google Patents
Phosphonated rifamycins and uses thereof for the prevention and treatment of bone and joint infections Download PDFInfo
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- AU2006339058B2 AU2006339058B2 AU2006339058A AU2006339058A AU2006339058B2 AU 2006339058 B2 AU2006339058 B2 AU 2006339058B2 AU 2006339058 A AU2006339058 A AU 2006339058A AU 2006339058 A AU2006339058 A AU 2006339058A AU 2006339058 B2 AU2006339058 B2 AU 2006339058B2
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- 229930189077 Rifamycin Natural products 0.000 title claims abstract description 144
- 238000011282 treatment Methods 0.000 title claims abstract description 71
- 229940081192 rifamycins Drugs 0.000 title abstract description 31
- BTVYFIMKUHNOBZ-QXMMDKDBSA-N rifamycin s Chemical class O=C1C(C(O)=C2C)=C3C(=O)C=C1NC(=O)\C(C)=C/C=C\C(C)C(O)C(C)C(O)C(C)C(OC(C)=O)C(C)C(OC)\C=C/OC1(C)OC2=C3C1=O BTVYFIMKUHNOBZ-QXMMDKDBSA-N 0.000 title abstract description 30
- 206010005940 Bone and joint infections Diseases 0.000 title abstract description 8
- 230000002265 prevention Effects 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 244
- 239000003242 anti bacterial agent Substances 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 59
- 238000011321 prophylaxis Methods 0.000 claims abstract description 26
- HJYYPODYNSCCOU-ODRIEIDWSA-N rifamycin SV Chemical compound OC1=C(C(O)=C2C)C3=C(O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O HJYYPODYNSCCOU-ODRIEIDWSA-N 0.000 claims description 121
- 210000000988 bone and bone Anatomy 0.000 claims description 113
- 229960003292 rifamycin Drugs 0.000 claims description 113
- 239000000203 mixture Substances 0.000 claims description 108
- 125000000217 alkyl group Chemical group 0.000 claims description 83
- 229940122361 Bisphosphonate Drugs 0.000 claims description 78
- 239000003814 drug Substances 0.000 claims description 63
- 125000005647 linker group Chemical group 0.000 claims description 63
- 229960000885 rifabutin Drugs 0.000 claims description 58
- 150000003839 salts Chemical class 0.000 claims description 56
- ZWBTYMGEBZUQTK-PVLSIAFMSA-N [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,32-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-6,23-dioxospiro[8,33-dioxa-24,27,29-triazapentacyclo[23.6.1.14,7.05,31.026,30]tritriaconta-1(32),2,4,9,19,21,24,26,30-nonaene-28,4'-piperidine]-13-yl] acetate Chemical compound CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C2=O)c2c4NC5(CCN(CC(C)C)CC5)N=c4c(=NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)c(O)c2c(O)c3C ZWBTYMGEBZUQTK-PVLSIAFMSA-N 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 44
- 239000008194 pharmaceutical composition Substances 0.000 claims description 42
- 150000004663 bisphosphonates Chemical group 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
- 229950005007 rifalazil Drugs 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 229960001225 rifampicin Drugs 0.000 claims description 25
- 208000035143 Bacterial infection Diseases 0.000 claims description 23
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 23
- SGHWBDUXKUSFOP-KYALZUAASA-N rifalazil Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)N=C2C(=O)C=3C(O)=C4C)C)OC)C4=C1C=3C(NC1=C(O)C=3)=C2OC1=CC=3N1CCN(CC(C)C)CC1 SGHWBDUXKUSFOP-KYALZUAASA-N 0.000 claims description 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 18
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 15
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 14
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000004098 Tetracycline Substances 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 235000019364 tetracycline Nutrition 0.000 claims description 11
- 150000003522 tetracyclines Chemical class 0.000 claims description 11
- 230000008878 coupling Effects 0.000 claims description 10
- 238000010168 coupling process Methods 0.000 claims description 10
- 238000005859 coupling reaction Methods 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- NZCRJKRKKOLAOJ-XRCRFVBUSA-N rifaximin Chemical compound OC1=C(C(O)=C2C)C3=C4N=C5C=C(C)C=CN5C4=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O NZCRJKRKKOLAOJ-XRCRFVBUSA-N 0.000 claims description 10
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 10
- FFTVPQUHLQBXQZ-KVUCHLLUSA-N (4s,4as,5ar,12ar)-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=C(N(C)C)C=CC(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O FFTVPQUHLQBXQZ-KVUCHLLUSA-N 0.000 claims description 8
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- DDTDNCYHLGRFBM-YZEKDTGTSA-N chembl2367892 Chemical compound CC(=O)N[C@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1O[C@@H]([C@H]1C(N[C@@H](C2=CC(O)=CC(O[C@@H]3[C@H]([C@H](O)[C@H](O)[C@@H](CO)O3)O)=C2C=2C(O)=CC=C(C=2)[C@@H](NC(=O)[C@@H]2NC(=O)[C@@H]3C=4C=C(O)C=C(C=4)OC=4C(O)=CC=C(C=4)[C@@H](N)C(=O)N[C@H](CC=4C=C(Cl)C(O5)=CC=4)C(=O)N3)C(=O)N1)C(O)=O)=O)C(C=C1Cl)=CC=C1OC1=C(O[C@H]3[C@H]([C@@H](O)[C@H](O)[C@H](CO)O3)NC(C)=O)C5=CC2=C1 DDTDNCYHLGRFBM-YZEKDTGTSA-N 0.000 claims description 8
- XJHXLMVKYIVZTE-LOALFDMRSA-N chloroeremomycin Chemical compound O([C@@H]1C2=CC=C(C(=C2)Cl)OC=2C=C3C=C(C=2O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O[C@@H]2O[C@@H](C)[C@H](O)[C@@](C)(N)C2)OC2=CC=C(C=C2Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]2C(=O)N[C@@H]1C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@@H](O)[C@H](C)O1 XJHXLMVKYIVZTE-LOALFDMRSA-N 0.000 claims description 8
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- UECIPBUIMXSXEI-BNSVOVDNSA-N eremomycin Chemical compound O([C@@H]1C2=CC=C(C=C2)OC=2C=C3C=C(C=2O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O[C@@H]2O[C@@H](C)[C@H](O)[C@@](C)(N)C2)OC2=CC=C(C=C2Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]2C(=O)N[C@@H]1C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@@H](O)[C@H](C)O1 UECIPBUIMXSXEI-BNSVOVDNSA-N 0.000 claims description 8
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- WDZCUPBHRAEYDL-GZAUEHORSA-N rifapentine Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C(O)=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N(CC1)CCN1C1CCCC1 WDZCUPBHRAEYDL-GZAUEHORSA-N 0.000 claims description 8
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
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- 235000021317 phosphate Nutrition 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
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- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
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- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical class CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical class OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
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- 125000003373 pyrazinyl group Chemical group 0.000 description 1
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- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical group N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- OIFKKXUCNTVCSO-HHQFNNIRSA-M sodium [(2S,5R)-2-(5-ethoxycarbonyl-1,2,4-oxadiazol-3-yl)-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] sulfate Chemical compound CCOC(=O)C1=NC(=NO1)[C@@H]1CC[C@@H]2CN1C(=O)N2OS(=O)(=O)O[Na] OIFKKXUCNTVCSO-HHQFNNIRSA-M 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229960005491 sodium morrhuate Drugs 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
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- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000011421 subcutaneous treatment Methods 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical class OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
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- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003441 thioacyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 101150071242 tolC gene Proteins 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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- 239000003643 water by type Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- GDJZZWYLFXAGFH-UHFFFAOYSA-M xylenesulfonate group Chemical group C1(C(C=CC=C1)C)(C)S(=O)(=O)[O-] GDJZZWYLFXAGFH-UHFFFAOYSA-M 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- 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
- A61K47/51—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 non-active ingredient being a modifying agent
- A61K47/54—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 non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/548—Phosphates or phosphonates, e.g. bone-seeking
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- 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
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Physical Education & Sports Medicine (AREA)
- Biochemistry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Biophysics (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70714505P | 2005-08-11 | 2005-08-11 | |
| US60/707,145 | 2005-08-11 | ||
| PCT/IB2006/004128 WO2007096703A2 (en) | 2005-08-11 | 2006-08-11 | Phosphonated rifamycins and uses thereof for the prevention and treatment of bone and joint infections |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2006339058A1 AU2006339058A1 (en) | 2007-08-30 |
| AU2006339058B2 true AU2006339058B2 (en) | 2012-09-06 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2006339058A Ceased AU2006339058B2 (en) | 2005-08-11 | 2006-08-11 | Phosphonated rifamycins and uses thereof for the prevention and treatment of bone and joint infections |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8404664B2 (enExample) |
| EP (1) | EP1928890B1 (enExample) |
| JP (1) | JP5368092B2 (enExample) |
| KR (1) | KR101327635B1 (enExample) |
| CN (1) | CN101282981B (enExample) |
| AU (1) | AU2006339058B2 (enExample) |
| BR (1) | BRPI0614758A2 (enExample) |
| CA (1) | CA2618741C (enExample) |
| EA (1) | EA016059B1 (enExample) |
| IL (1) | IL189270A (enExample) |
| WO (1) | WO2007096703A2 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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- 2006-08-11 KR KR1020087005807A patent/KR101327635B1/ko not_active Expired - Fee Related
- 2006-08-11 BR BRPI0614758-5A patent/BRPI0614758A2/pt not_active Application Discontinuation
- 2006-08-11 US US12/063,300 patent/US8404664B2/en not_active Expired - Fee Related
- 2006-08-11 AU AU2006339058A patent/AU2006339058B2/en not_active Ceased
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Also Published As
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| KR101327635B1 (ko) | 2013-11-12 |
| CA2618741A1 (en) | 2007-08-30 |
| CA2618741C (en) | 2014-03-25 |
| IL189270A0 (en) | 2008-08-07 |
| CN101282981B (zh) | 2012-09-26 |
| US20110263534A1 (en) | 2011-10-27 |
| KR20080035687A (ko) | 2008-04-23 |
| JP5368092B2 (ja) | 2013-12-18 |
| US8404664B2 (en) | 2013-03-26 |
| EP1928890B1 (en) | 2013-04-03 |
| EP1928890A2 (en) | 2008-06-11 |
| WO2007096703A2 (en) | 2007-08-30 |
| IL189270A (en) | 2015-05-31 |
| WO2007096703A3 (en) | 2008-01-03 |
| EA016059B1 (ru) | 2012-01-30 |
| EA200800570A1 (ru) | 2009-02-27 |
| JP2009505974A (ja) | 2009-02-12 |
| AU2006339058A1 (en) | 2007-08-30 |
| CN101282981A (zh) | 2008-10-08 |
| BRPI0614758A2 (pt) | 2011-04-12 |
| EP1928890A4 (en) | 2011-08-31 |
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