CA2737524A1 - Organic compounds for applications in bacterial infections treatment - Google Patents
Organic compounds for applications in bacterial infections treatment Download PDFInfo
- Publication number
- CA2737524A1 CA2737524A1 CA2737524A CA2737524A CA2737524A1 CA 2737524 A1 CA2737524 A1 CA 2737524A1 CA 2737524 A CA2737524 A CA 2737524A CA 2737524 A CA2737524 A CA 2737524A CA 2737524 A1 CA2737524 A1 CA 2737524A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- group
- substituted
- unsubstituted
- c4alkyl
- 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
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- 238000011282 treatment Methods 0.000 title claims abstract description 24
- 208000035143 Bacterial infection Diseases 0.000 title claims description 17
- 208000022362 bacterial infectious disease Diseases 0.000 title claims description 17
- 150000002894 organic compounds Chemical class 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 253
- 238000000034 method Methods 0.000 claims description 192
- -1 C1-C6alkoxy Chemical group 0.000 claims description 129
- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 44
- 239000003814 drug Substances 0.000 claims description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- 125000000623 heterocyclic group Chemical group 0.000 claims description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 241000894006 Bacteria Species 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000004429 atom Chemical group 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 230000002401 inhibitory effect Effects 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- 239000003112 inhibitor Substances 0.000 claims description 11
- 239000003937 drug carrier Substances 0.000 claims description 10
- 208000015181 infectious disease Diseases 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000006413 ring segment Chemical group 0.000 claims description 10
- 208000027096 gram-negative bacterial infections Diseases 0.000 claims description 9
- 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 8
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 8
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 7
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 7
- 241000588921 Enterobacteriaceae Species 0.000 claims description 6
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 6
- 241000588769 Proteus <enterobacteria> Species 0.000 claims description 6
- 241000607142 Salmonella Species 0.000 claims description 6
- 241000607720 Serratia Species 0.000 claims description 6
- 229940124597 therapeutic agent Drugs 0.000 claims description 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 241000589291 Acinetobacter Species 0.000 claims description 5
- 241000588914 Enterobacter Species 0.000 claims description 5
- OWQGGUZHYIFZRN-RNCFNFMXSA-N n-[(2s,3r)-3-amino-1-(hydroxyamino)-1-oxobutan-2-yl]-4-but-2-ynoxy-2-fluorobenzamide Chemical compound CC#CCOC1=CC=C(C(=O)N[C@@H]([C@@H](C)N)C(=O)NO)C(F)=C1 OWQGGUZHYIFZRN-RNCFNFMXSA-N 0.000 claims description 5
- PYMXQIVDCHTBAC-XVSSEFHLSA-N n-[(2s,3r)-3-amino-1-(hydroxyamino)-1-oxobutan-2-yl]-4-but-2-ynoxycyclohexane-1-carboxamide Chemical compound CC#CCOC1CCC(C(=O)N[C@@H]([C@@H](C)N)C(=O)NO)CC1 PYMXQIVDCHTBAC-XVSSEFHLSA-N 0.000 claims description 5
- GGBCAIKKJZYVLI-NWDGAFQWSA-N n-[(2s,3r)-3-amino-4,4,4-trifluoro-1-(hydroxyamino)-1-oxobutan-2-yl]-4-but-2-ynoxybenzamide Chemical compound CC#CCOC1=CC=C(C(=O)N[C@@H]([C@@H](N)C(F)(F)F)C(=O)NO)C=C1 GGBCAIKKJZYVLI-NWDGAFQWSA-N 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 229960000707 tobramycin Drugs 0.000 claims description 5
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 claims description 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
- 241001673062 Achromobacter xylosoxidans Species 0.000 claims description 4
- WZPBZJONDBGPKJ-UHFFFAOYSA-N Antibiotic SQ 26917 Natural products O=C1N(S(O)(=O)=O)C(C)C1NC(=O)C(=NOC(C)(C)C(O)=O)C1=CSC(N)=N1 WZPBZJONDBGPKJ-UHFFFAOYSA-N 0.000 claims description 4
- 241000588923 Citrobacter Species 0.000 claims description 4
- 108090000790 Enzymes Proteins 0.000 claims description 4
- 102000004190 Enzymes Human genes 0.000 claims description 4
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 claims description 4
- 229930182566 Gentamicin Natural products 0.000 claims description 4
- 241000588748 Klebsiella Species 0.000 claims description 4
- 241000588653 Neisseria Species 0.000 claims description 4
- 108010040201 Polymyxins Proteins 0.000 claims description 4
- 241000122973 Stenotrophomonas maltophilia Species 0.000 claims description 4
- 239000004098 Tetracycline Substances 0.000 claims description 4
- 229960004099 azithromycin Drugs 0.000 claims description 4
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 claims description 4
- WZPBZJONDBGPKJ-VEHQQRBSSA-N aztreonam Chemical compound O=C1N(S([O-])(=O)=O)[C@@H](C)[C@@H]1NC(=O)C(=N/OC(C)(C)C(O)=O)\C1=CSC([NH3+])=N1 WZPBZJONDBGPKJ-VEHQQRBSSA-N 0.000 claims description 4
- 229960003644 aztreonam Drugs 0.000 claims description 4
- 229960003405 ciprofloxacin Drugs 0.000 claims description 4
- 229960001225 rifampicin Drugs 0.000 claims description 4
- 235000019364 tetracycline Nutrition 0.000 claims description 4
- 150000003522 tetracyclines Chemical class 0.000 claims description 4
- SGKRLCUYIXIAHR-AKNGSSGZSA-N (4s,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-AKNGSSGZSA-N 0.000 claims description 3
- 241000588807 Bordetella Species 0.000 claims description 3
- 241000589513 Burkholderia cepacia Species 0.000 claims description 3
- 241000046135 Cedecea Species 0.000 claims description 3
- 241000607473 Edwardsiella <enterobacteria> Species 0.000 claims description 3
- 241000588724 Escherichia coli Species 0.000 claims description 3
- 241000606790 Haemophilus Species 0.000 claims description 3
- 241000589248 Legionella Species 0.000 claims description 3
- GSDSWSVVBLHKDQ-JTQLQIEISA-N Levofloxacin Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-JTQLQIEISA-N 0.000 claims description 3
- 241000588771 Morganella <proteobacterium> Species 0.000 claims description 3
- 241000588768 Providencia Species 0.000 claims description 3
- 241000589516 Pseudomonas Species 0.000 claims description 3
- 241000607768 Shigella Species 0.000 claims description 3
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 claims description 3
- 241000607734 Yersinia <bacteria> Species 0.000 claims description 3
- 229960004821 amikacin Drugs 0.000 claims description 3
- LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 claims description 3
- 229960000723 ampicillin Drugs 0.000 claims description 3
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 229960002100 cefepime Drugs 0.000 claims description 3
- 229960004261 cefotaxime Drugs 0.000 claims description 3
- AZZMGZXNTDTSME-JUZDKLSSSA-M cefotaxime sodium Chemical compound [Na+].N([C@@H]1C(N2C(=C(COC(C)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 AZZMGZXNTDTSME-JUZDKLSSSA-M 0.000 claims description 3
- 229960004755 ceftriaxone Drugs 0.000 claims description 3
- VAAUVRVFOQPIGI-SPQHTLEESA-N ceftriaxone Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NC(=O)C(=O)NN1C VAAUVRVFOQPIGI-SPQHTLEESA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229960002227 clindamycin Drugs 0.000 claims description 3
- KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 claims description 3
- 229960003722 doxycycline Drugs 0.000 claims description 3
- 229960003276 erythromycin Drugs 0.000 claims description 3
- 229960002182 imipenem Drugs 0.000 claims description 3
- ZSKVGTPCRGIANV-ZXFLCMHBSA-N imipenem Chemical compound C1C(SCC\N=C\N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 ZSKVGTPCRGIANV-ZXFLCMHBSA-N 0.000 claims description 3
- 229960003376 levofloxacin Drugs 0.000 claims description 3
- DMJNNHOOLUXYBV-PQTSNVLCSA-N meropenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](C(=O)N(C)C)C1 DMJNNHOOLUXYBV-PQTSNVLCSA-N 0.000 claims description 3
- 229960002260 meropenem Drugs 0.000 claims description 3
- BGUNXABNVHNTGX-UHFFFAOYSA-N n-[3-amino-1-(hydroxyamino)-3-methyl-1-oxobutan-2-yl]-4-(4,4-dimethylpent-2-ynoxy)benzamide Chemical compound CC(C)(C)C#CCOC1=CC=C(C(=O)NC(C(=O)NO)C(C)(C)N)C=C1 BGUNXABNVHNTGX-UHFFFAOYSA-N 0.000 claims description 3
- JPCUWLVKAJJSLN-UHFFFAOYSA-N n-[3-amino-1-(hydroxyamino)-3-methyl-1-oxobutan-2-yl]-4-but-2-ynoxybenzamide Chemical compound CC#CCOC1=CC=C(C(=O)NC(C(=O)NO)C(C)(C)N)C=C1 JPCUWLVKAJJSLN-UHFFFAOYSA-N 0.000 claims description 3
- 229940056360 penicillin g Drugs 0.000 claims description 3
- 229960002292 piperacillin Drugs 0.000 claims description 3
- WCMIIGXFCMNQDS-IDYPWDAWSA-M piperacillin sodium Chemical compound [Na+].O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC=CC=1)C(=O)N[C@@H]1C(=O)N2[C@@H](C([O-])=O)C(C)(C)S[C@@H]21 WCMIIGXFCMNQDS-IDYPWDAWSA-M 0.000 claims description 3
- 229960002180 tetracycline Drugs 0.000 claims description 3
- 229930101283 tetracycline Natural products 0.000 claims description 3
- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 claims description 3
- 229960004659 ticarcillin Drugs 0.000 claims description 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 2
- 241001453380 Burkholderia Species 0.000 claims description 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 2
- 101100134922 Gallus gallus COR5 gene Proteins 0.000 claims description 2
- 208000007764 Legionnaires' Disease Diseases 0.000 claims description 2
- 241000588621 Moraxella Species 0.000 claims description 2
- 241000607598 Vibrio Species 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- HQHYZYYMVAXQID-UHFFFAOYSA-N n-[1-(1-aminocyclopropyl)-2-(hydroxyamino)-2-oxoethyl]-4-but-2-ynoxybenzamide Chemical compound C1=CC(OCC#CC)=CC=C1C(=O)NC(C(=O)NO)C1(N)CC1 HQHYZYYMVAXQID-UHFFFAOYSA-N 0.000 claims description 2
- 125000005551 pyridylene group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- MMRINLZOZVAPDZ-LSGRDSQZSA-N (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methylpyrrolidin-1-ium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;chloride Chemical compound Cl.S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1C[N+]1(C)CCCC1 MMRINLZOZVAPDZ-LSGRDSQZSA-N 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004431 deuterium atom Chemical group 0.000 claims 1
- PSHHTTQQTBVDML-CABCVRRESA-N n-[(1r,2s)-1-amino-1-cyclopropyl-3-(hydroxyamino)-3-oxopropan-2-yl]-4-but-2-ynoxybenzamide Chemical compound C1=CC(OCC#CC)=CC=C1C(=O)N[C@H](C(=O)NO)[C@H](N)C1CC1 PSHHTTQQTBVDML-CABCVRRESA-N 0.000 claims 1
- NKFFENLDZVMLAC-UHFFFAOYSA-N n-[3-amino-1-(hydroxyamino)-3-methyl-1-oxobutan-2-yl]-4-(4-hydroxy-4-methylpent-2-ynoxy)benzamide Chemical compound CC(C)(O)C#CCOC1=CC=C(C(=O)NC(C(=O)NO)C(C)(C)N)C=C1 NKFFENLDZVMLAC-UHFFFAOYSA-N 0.000 claims 1
- JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin 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\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 18
- 201000010099 disease Diseases 0.000 abstract description 12
- 230000002265 prevention Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 113
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 105
- 239000000203 mixture Substances 0.000 description 100
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 91
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- 239000000243 solution Substances 0.000 description 74
- 238000006243 chemical reaction Methods 0.000 description 59
- 235000019439 ethyl acetate Nutrition 0.000 description 47
- 229910001868 water Inorganic materials 0.000 description 44
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 39
- 125000000217 alkyl group Chemical group 0.000 description 37
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- 125000003118 aryl group Chemical group 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 32
- 238000003786 synthesis reaction Methods 0.000 description 30
- 239000003795 chemical substances by application Substances 0.000 description 29
- 229940079593 drug Drugs 0.000 description 28
- 230000015572 biosynthetic process Effects 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
- 239000008194 pharmaceutical composition Substances 0.000 description 25
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 24
- 230000002829 reductive effect Effects 0.000 description 24
- 125000000304 alkynyl group Chemical group 0.000 description 23
- 229910052799 carbon Inorganic materials 0.000 description 23
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 22
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
- 125000003342 alkenyl group Chemical group 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 239000002253 acid Substances 0.000 description 21
- 239000000651 prodrug Substances 0.000 description 21
- 229940002612 prodrug Drugs 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 21
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/20—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hydrogen atoms and substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D309/22—Radicals substituted by oxygen atoms
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
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- A61P31/12—Antivirals
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Virology (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9766408P | 2008-09-17 | 2008-09-17 | |
| US61/097,664 | 2008-09-17 | ||
| PCT/EP2009/061905 WO2010031750A1 (en) | 2008-09-17 | 2009-09-15 | Organic compounds for applications in bacterial infections treatment |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2737524A1 true CA2737524A1 (en) | 2010-03-25 |
Family
ID=41397755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2737524A Abandoned CA2737524A1 (en) | 2008-09-17 | 2009-09-15 | Organic compounds for applications in bacterial infections treatment |
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| Country | Link |
|---|---|
| US (1) | US8372885B2 (enExample) |
| EP (1) | EP2340241A1 (enExample) |
| JP (1) | JP5550650B2 (enExample) |
| KR (1) | KR20110055735A (enExample) |
| CN (1) | CN102159537B (enExample) |
| AR (1) | AR074719A1 (enExample) |
| AU (1) | AU2009294710A1 (enExample) |
| CA (1) | CA2737524A1 (enExample) |
| EA (1) | EA201100505A1 (enExample) |
| MX (1) | MX2011002804A (enExample) |
| TW (1) | TW201018460A (enExample) |
| UY (1) | UY32123A (enExample) |
| WO (1) | WO2010031750A1 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008154642A2 (en) * | 2007-06-12 | 2008-12-18 | Achaogen, Inc. | Antibacterial agents |
| EP2334636A2 (en) | 2008-09-19 | 2011-06-22 | Pfizer Inc. | Hydroxamic acid derivatives useful as antibacterial agents |
| WO2011005355A1 (en) * | 2009-05-07 | 2011-01-13 | Achaogen, Inc. | Combinations comprising a lpxc inhibitor and an antibiotic for use in the treatment of infections caused by gram-negative bacteria |
| JP5591494B2 (ja) * | 2009-07-14 | 2014-09-17 | 東ソ−・エフテック株式会社 | 高純度の含フッ素エチリデン−2−メチルプロパンスルフィンアミド、その製造方法及びそれを用いた光学活性含フッ素アミン誘導体の製造方法 |
| PL2512474T3 (pl) | 2009-12-16 | 2015-03-31 | Pfizer | N-przyłączone pochodne kwasu hydroksamowego użyteczne jako środki przeciwbakteryjne |
| US8247436B2 (en) | 2010-03-19 | 2012-08-21 | Novartis Ag | Pyridine and pyrazine derivative for the treatment of CF |
| PH12012502087A1 (en) | 2010-04-20 | 2015-04-15 | Taisho Pharmaceutical Co Ltd | Novel hydroxamic acid derivative |
| US9738604B2 (en) | 2010-09-03 | 2017-08-22 | Duke University | Ethynylbenzene derivatives |
| AP3336A (en) | 2011-03-07 | 2015-07-31 | Pfizer | Fluoro-pyridinone derivatives useful as antibacterial agents |
| SG193458A1 (en) | 2011-04-08 | 2013-10-30 | Pfizer | Imidazole, pyrazole, and triazole derivatives useful as antibacterial agents |
| CN103717582B (zh) | 2011-04-08 | 2015-09-30 | 辉瑞大药厂 | 用作抗菌剂的异*唑衍生物 |
| JP6006609B2 (ja) * | 2011-10-19 | 2016-10-12 | 大正製薬株式会社 | 新規なヒドロキサム酸誘導体を含有する医薬 |
| JP5869311B2 (ja) * | 2011-11-21 | 2016-02-24 | 国立大学法人 名古屋工業大学 | 光学活性含フッ素β−アミノ酸誘導体及びその製造法 |
| WO2013170165A1 (en) | 2012-05-10 | 2013-11-14 | Achaogen, Inc. | Antibacterial agents |
| JP5902575B2 (ja) * | 2012-07-20 | 2016-04-13 | 国立大学法人お茶の水女子大学 | 光学活性含フッ素アミン化合物の製造方法並びに光学活性含フッ素アミン化合物 |
| CN104470940B (zh) | 2012-09-19 | 2018-10-16 | 霍夫曼-拉罗奇有限公司 | 2-氧代-2,3,4,5-四氢-1H-苯并[b][1,4]二氮杂*及其治疗癌症的用途 |
| WO2014165075A1 (en) | 2013-03-12 | 2014-10-09 | Achaogen, Inc. | Antibacterial agents |
| TR201911245T4 (tr) | 2013-03-15 | 2019-08-21 | Fujifilm Toyama Chemical Co Ltd | Yeni hidroksamik asit türevi veya bunun tuzu. |
| CA2921427A1 (en) * | 2013-08-16 | 2015-02-19 | Duke University | Substituted hydroxamic acid compounds |
| US9908851B2 (en) | 2013-08-16 | 2018-03-06 | Duke University | 2-piperidinyl substituted N,3-dihydroxybutanamides |
| US10189786B2 (en) | 2013-08-16 | 2019-01-29 | Duke University | Antibacterial compounds |
| KR20170048546A (ko) | 2014-09-12 | 2017-05-08 | 토야마 케미칼 컴퍼니 리미티드 | 신규 히드록삼산 유도체 또는 그 염을 함유하는 의약 조성물 |
| JPWO2016039432A1 (ja) | 2014-09-12 | 2017-06-22 | 富山化学工業株式会社 | 新規なヒドロキサム酸誘導体および抗菌性物質を組み合わせて使用する方法 |
| CN105669750B (zh) * | 2016-03-01 | 2018-04-03 | 中国医学科学院医药生物技术研究所 | 新型锌离子螯合剂及其制备和在抗革兰氏阴性菌感染中的应用 |
| EP3448375B1 (en) | 2016-04-25 | 2023-09-27 | Duke University | Benzoylglycine derivatives and methods of making and using same |
| WO2017223349A1 (en) | 2016-06-23 | 2017-12-28 | Achaogen, Inc. | Antibacterial agents |
| US11299455B2 (en) | 2018-07-12 | 2022-04-12 | Piramal Pharma Limited | Process for diastereoselective synthesis of vicinal diamines |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1577345A (en) | 1976-06-10 | 1980-10-22 | Eisai Co Ltd | Hydroxamic acid derivatives of use in the treatment of urolithiasis and pyelonephrosis |
| US6951884B2 (en) | 2002-06-12 | 2005-10-04 | Hoffmann-La Roche Inc. | Fluorobenzamides and uses thereof |
| SG2012000667A (en) * | 2003-01-08 | 2015-03-30 | Univ Washington | Antibacterial agents |
| CA2528231A1 (en) | 2003-06-13 | 2004-12-23 | Laboratorios S.A.L.V.A.T., S.A. | New benzamides as ppar.gamma. modulators |
| US7714168B2 (en) | 2005-10-27 | 2010-05-11 | Sumitomo Chemical Company, Limited | Amide compounds and their use |
| WO2008154642A2 (en) * | 2007-06-12 | 2008-12-18 | Achaogen, Inc. | Antibacterial agents |
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2009
- 2009-09-11 US US12/557,654 patent/US8372885B2/en not_active Expired - Fee Related
- 2009-09-15 EA EA201100505A patent/EA201100505A1/ru unknown
- 2009-09-15 EP EP09782998A patent/EP2340241A1/en not_active Withdrawn
- 2009-09-15 MX MX2011002804A patent/MX2011002804A/es not_active Application Discontinuation
- 2009-09-15 CA CA2737524A patent/CA2737524A1/en not_active Abandoned
- 2009-09-15 AU AU2009294710A patent/AU2009294710A1/en not_active Abandoned
- 2009-09-15 WO PCT/EP2009/061905 patent/WO2010031750A1/en not_active Ceased
- 2009-09-15 CN CN200980136312.2A patent/CN102159537B/zh not_active Expired - Fee Related
- 2009-09-15 KR KR1020117008624A patent/KR20110055735A/ko not_active Withdrawn
- 2009-09-15 JP JP2011527300A patent/JP5550650B2/ja not_active Expired - Fee Related
- 2009-09-15 AR ARP090103529A patent/AR074719A1/es unknown
- 2009-09-16 TW TW098131268A patent/TW201018460A/zh unknown
- 2009-09-16 UY UY0001032123A patent/UY32123A/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JP5550650B2 (ja) | 2014-07-16 |
| EA201100505A1 (ru) | 2011-10-31 |
| CN102159537A (zh) | 2011-08-17 |
| US20100120872A1 (en) | 2010-05-13 |
| TW201018460A (en) | 2010-05-16 |
| CN102159537B (zh) | 2014-11-05 |
| UY32123A (es) | 2010-04-30 |
| WO2010031750A1 (en) | 2010-03-25 |
| AU2009294710A1 (en) | 2010-03-25 |
| AR074719A1 (es) | 2011-02-09 |
| EP2340241A1 (en) | 2011-07-06 |
| MX2011002804A (es) | 2011-04-11 |
| KR20110055735A (ko) | 2011-05-25 |
| US8372885B2 (en) | 2013-02-12 |
| JP2012502946A (ja) | 2012-02-02 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |
Effective date: 20130917 |