CA2658506C - Acrylamide derivatives as fab 1 inhibitors - Google Patents
Acrylamide derivatives as fab 1 inhibitors Download PDFInfo
- Publication number
- CA2658506C CA2658506C CA2658506A CA2658506A CA2658506C CA 2658506 C CA2658506 C CA 2658506C CA 2658506 A CA2658506 A CA 2658506A CA 2658506 A CA2658506 A CA 2658506A CA 2658506 C CA2658506 C CA 2658506C
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- pyrido
- acrylamide
- compound
- tetrahydro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 239000003112 inhibitor Substances 0.000 title description 29
- 150000003926 acrylamides Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 356
- 239000000203 mixture Substances 0.000 claims abstract description 283
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 6
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 56
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- FJWSMXKFXFFEPV-UHFFFAOYSA-N prop-2-enamide;hydrochloride Chemical compound Cl.NC(=O)C=C FJWSMXKFXFFEPV-UHFFFAOYSA-N 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 239000000829 suppository Substances 0.000 claims description 5
- HVNOQCNEOFIEJG-OUKQBFOZSA-N (e)-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]-3-(4-phenyl-1,2,3,5-tetrahydropyrido[2,3-e][1,4]diazepin-7-yl)prop-2-enamide Chemical compound O1C2=CC=CC=C2C(C)=C1CN(C)C(=O)\C=C\C(C=C1C2)=CN=C1NCCN2C1=CC=CC=C1 HVNOQCNEOFIEJG-OUKQBFOZSA-N 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- DVROUVDGEKDRTL-BQYQJAHWSA-N (e)-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]-3-(2,3,4,5-tetrahydro-1h-pyrido[2,3-e][1,4]diazepin-7-yl)prop-2-enamide Chemical compound N1CCNCC2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4O3)C)C)=CN=C21 DVROUVDGEKDRTL-BQYQJAHWSA-N 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- VBJRVJSNAGPPNR-BQYQJAHWSA-N (e)-n-methyl-n-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-(4-oxo-2,3,5,6-tetrahydro-1h-pyrido[2,3-b][1,5]diazocin-8-yl)prop-2-enamide Chemical compound N1CCC(=O)NCC2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4S3)C)C)=CN=C21 VBJRVJSNAGPPNR-BQYQJAHWSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 238000007910 systemic administration Methods 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims 1
- RZPNYZPFZNZBND-CMDGGOBGSA-N (e)-3-(1,2,3,4,5,6-hexahydropyrido[2,3-b][1,5]diazocin-8-yl)-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]prop-2-enamide Chemical compound N1CCCNCC2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4O3)C)C)=CN=C21 RZPNYZPFZNZBND-CMDGGOBGSA-N 0.000 claims 1
- JORIROYQKODZLZ-MDZDMXLPSA-N (e)-3-(2,2-dimethyl-3-oxo-4h-pyrido[3,2-b][1,4]oxazin-7-yl)-n-methyl-n-[(3-methyl-1h-indol-2-yl)methyl]prop-2-enamide Chemical compound N1C(=O)C(C)(C)OC2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4N3)C)C)=CN=C21 JORIROYQKODZLZ-MDZDMXLPSA-N 0.000 claims 1
- DIFKKRMHIPUBNM-RRABGKBLSA-N (e)-3-(3,3-dimethyl-1,2,4,5-tetrahydropyrido[2,3-e][1,4]diazepin-7-yl)-n-methyl-n-[(3-methyl-1-benzothiophen-2-yl)methyl]prop-2-enamide;hydrochloride Chemical compound Cl.N1CC(C)(C)NCC2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4S3)C)C)=CN=C21 DIFKKRMHIPUBNM-RRABGKBLSA-N 0.000 claims 1
- MNFBFBWTZYHEQX-MDZDMXLPSA-N (e)-3-(3,3-dimethyl-1,2-dihydropyrido[2,3-e][1,4]diazepin-7-yl)-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]prop-2-enamide Chemical compound N1CC(C)(C)N=CC2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4O3)C)C)=CN=C21 MNFBFBWTZYHEQX-MDZDMXLPSA-N 0.000 claims 1
- QCXPSKFNZGKSEF-RRABGKBLSA-N (e)-3-(3,3-dimethyl-1,2-dihydropyrido[2,3-e][1,4]diazepin-7-yl)-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]prop-2-enamide;hydrochloride Chemical compound Cl.N1CC(C)(C)N=CC2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4O3)C)C)=CN=C21 QCXPSKFNZGKSEF-RRABGKBLSA-N 0.000 claims 1
- CRKOCOWRTJFRBI-FMQWLBJXSA-N (e)-3-(3,3-dimethyl-2-oxo-1,5-dihydropyrido[2,3-e][1,4]oxazepin-7-yl)-n-[(1r)-1-(3-methoxy-2-propoxyphenyl)ethyl]-n-methylprop-2-enamide Chemical compound CCCOC1=C(OC)C=CC=C1[C@@H](C)N(C)C(=O)\C=C\C1=CN=C(NC(=O)C(C)(C)OC2)C2=C1 CRKOCOWRTJFRBI-FMQWLBJXSA-N 0.000 claims 1
- PFGIPCRDSQFHGZ-MDZDMXLPSA-N (e)-3-(3,3-dimethyl-4,5-dihydro-2h-pyrido[3,2-b][1,4]oxazepin-8-yl)-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]prop-2-enamide Chemical compound N1CC(C)(C)COC2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4O3)C)C)=CN=C21 PFGIPCRDSQFHGZ-MDZDMXLPSA-N 0.000 claims 1
- ABWHYSMHWAKPCX-ZHACJKMWSA-N (e)-3-(3,3-dimethyl-4-oxo-2,5-dihydropyrido[3,2-b][1,4]oxazepin-8-yl)-n-[(3-methoxy-2-propoxyphenyl)methyl]-n-methylprop-2-enamide Chemical compound C1=CC=C(OC)C(OCCC)=C1CN(C)C(=O)\C=C\C1=CN=C(NC(=O)C(C)(C)CO2)C2=C1 ABWHYSMHWAKPCX-ZHACJKMWSA-N 0.000 claims 1
- OQKSNMRAHGPKAU-HRNDJLQDSA-N (e)-3-(4-acetyl-1,2,3,5-tetrahydropyrido[2,3-e][1,4]diazepin-7-yl)-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]prop-2-enamide;hydrochloride Chemical compound Cl.N1CCN(C(C)=O)CC2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4O3)C)C)=CN=C21 OQKSNMRAHGPKAU-HRNDJLQDSA-N 0.000 claims 1
- YSYOIFKCMANYRV-JXMROGBWSA-N (e)-3-(5-hydroxy-8-oxo-5,6,7,9-tetrahydropyrido[2,3-b]azepin-3-yl)-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]prop-2-enamide Chemical compound N1C(=O)CCC(O)C2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4O3)C)C)=CN=C21 YSYOIFKCMANYRV-JXMROGBWSA-N 0.000 claims 1
- UZWRMQDFJPAYHO-UXULGGHQSA-N (e)-3-[(3s)-3-benzyl-2,3,4,5-tetrahydro-1h-pyrido[2,3-e][1,4]diazepin-7-yl]-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]prop-2-enamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C([C@H]1CNC2=NC=C(C=C2CN1)/C=C/C(=O)N(CC1=C(C2=CC=CC=C2O1)C)C)C1=CC=CC=C1 UZWRMQDFJPAYHO-UXULGGHQSA-N 0.000 claims 1
- BFEJTYGIEAOXFN-ASTDGNLGSA-N (e)-3-[2,2-dimethyl-3-(methylamino)pyrido[3,2-b][1,4]oxazin-7-yl]-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]prop-2-enamide;hydrochloride Chemical compound Cl.O1C2=CC=CC=C2C(C)=C1CN(C)C(=O)/C=C/C1=CN=C2N/C(=N/C)C(C)(C)OC2=C1 BFEJTYGIEAOXFN-ASTDGNLGSA-N 0.000 claims 1
- JLHKDYJQOZUARQ-ZHACJKMWSA-N (e)-3-[2,2-dimethyl-3-(methylamino)pyrido[3,2-b][1,4]oxazin-7-yl]-n-methyl-n-[(3-methyl-1-benzothiophen-2-yl)methyl]prop-2-enamide Chemical compound S1C2=CC=CC=C2C(C)=C1CN(C)C(=O)/C=C/C1=CN=C2N/C(=N/C)C(C)(C)OC2=C1 JLHKDYJQOZUARQ-ZHACJKMWSA-N 0.000 claims 1
- RERCAVBFOPPDGY-BQYQJAHWSA-N (e)-n-[(3,4-dimethylthieno[2,3-b]thiophen-5-yl)methyl]-n-methyl-3-(8-oxo-5,6,7,9-tetrahydropyrido[2,3-b]azepin-3-yl)prop-2-enamide Chemical compound N1C(=O)CCCC2=CC(/C=C/C(=O)N(CC3=C(C=4C(C)=CSC=4S3)C)C)=CN=C21 RERCAVBFOPPDGY-BQYQJAHWSA-N 0.000 claims 1
- XSKYUXOMNYYVBJ-CMDGGOBGSA-N (e)-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]-3-(2,3,4,5-tetrahydro-1h-pyrido[2,3-b][1,4]diazepin-8-yl)prop-2-enamide Chemical compound N1CCCNC2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4O3)C)C)=CN=C21 XSKYUXOMNYYVBJ-CMDGGOBGSA-N 0.000 claims 1
- YWZXJGLWPAYZKA-HRNDJLQDSA-N (e)-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]-3-(4-methylsulfonyl-1,2,3,5-tetrahydropyrido[2,3-e][1,4]diazepin-7-yl)prop-2-enamide;hydrochloride Chemical compound Cl.N1CCN(S(C)(=O)=O)CC2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4O3)C)C)=CN=C21 YWZXJGLWPAYZKA-HRNDJLQDSA-N 0.000 claims 1
- SKVWKHPMSLUTLM-HRNDJLQDSA-N (e)-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]-3-(5-methyl-4-oxo-1,2,3,6-tetrahydropyrido[2,3-b][1,5]diazocin-8-yl)prop-2-enamide;hydrochloride Chemical compound Cl.N1CCC(=O)N(C)CC2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4O3)C)C)=CN=C21 SKVWKHPMSLUTLM-HRNDJLQDSA-N 0.000 claims 1
- AOVIKGVBACAFRB-VWUNKNEVSA-N (e)-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]-3-[(3r)-3-methyl-2,3,4,5-tetrahydro-1h-pyrido[2,3-e][1,4]diazepin-7-yl]prop-2-enamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C2CN[C@H](C)CNC2=NC=C1\C=C\C(=O)N(C)CC1=C(C)C2=CC=CC=C2O1 AOVIKGVBACAFRB-VWUNKNEVSA-N 0.000 claims 1
- BVZVUDIBWKNPHW-CMDGGOBGSA-N (e)-n-methyl-n-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-(2,3,4,5-tetrahydro-1h-pyrido[2,3-b][1,4]diazepin-8-yl)prop-2-enamide Chemical compound N1CCCNC2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4S3)C)C)=CN=C21 BVZVUDIBWKNPHW-CMDGGOBGSA-N 0.000 claims 1
- DIMGYXRTBUURFG-USRGLUTNSA-N (e)-n-methyl-n-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-(2,3,4,5-tetrahydro-1h-pyrido[2,3-e][1,4]diazepin-7-yl)prop-2-enamide;hydrochloride Chemical compound Cl.N1CCNCC2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4S3)C)C)=CN=C21 DIMGYXRTBUURFG-USRGLUTNSA-N 0.000 claims 1
- WDRMNPKMBMILQR-BQYQJAHWSA-N (e)-n-methyl-n-[(3-methyl-1h-indol-2-yl)methyl]-3-(1,2,3,5-tetrahydropyrido[2,3-e][1,4]oxazepin-7-yl)prop-2-enamide Chemical compound N1CCOCC2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4N3)C)C)=CN=C21 WDRMNPKMBMILQR-BQYQJAHWSA-N 0.000 claims 1
- LQYQZCKKDMRZRQ-HJCTYBPXSA-N (e)-n-methyl-n-[(3-methyl-3a,7a-dihydro-1-benzofuran-2-yl)methyl]-3-[(3s)-3-methyl-2,3,4,5-tetrahydro-1h-pyrido[2,3-e][1,4]diazepin-7-yl]prop-2-enamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C2CN[C@@H](C)CNC2=NC=C1\C=C\C(=O)N(C)CC(O1)=C(C)C2C1C=CC=C2 LQYQZCKKDMRZRQ-HJCTYBPXSA-N 0.000 claims 1
- VGUYHEPLYSXHNU-MRXNPFEDSA-N 3-(3,3-dimethyl-4-oxo-2,5-dihydropyrido[3,2-b][1,4]oxazepin-8-yl)-n-methyl-n-[(1r)-1-(3-methyl-1-benzofuran-2-yl)ethyl]prop-2-enamide Chemical compound N1C(=O)C(C)(C)COC2=CC(C=CC(=O)N(C)[C@H](C)C3=C(C4=CC=CC=C4O3)C)=CN=C21 VGUYHEPLYSXHNU-MRXNPFEDSA-N 0.000 claims 1
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims 1
- VQIGBUZJMBJGEY-UHFFFAOYSA-N n-methyl-n-[(1-methylindol-2-yl)methyl]-3-(1,2,3,5-tetrahydropyrido[2,3-e][1,4]oxazepin-7-yl)prop-2-enamide Chemical compound N1CCOCC2=CC(C=CC(=O)N(CC=3N(C4=CC=CC=C4C=3)C)C)=CN=C21 VQIGBUZJMBJGEY-UHFFFAOYSA-N 0.000 claims 1
- JWBSXUBRCMAXSR-UHFFFAOYSA-N n-methyl-n-[(1-methylindol-2-yl)methyl]-3-(4-methyl-1,2,3,5-tetrahydropyrido[2,3-e][1,4]diazepin-7-yl)prop-2-enamide;dihydrochloride Chemical compound Cl.Cl.N1CCN(C)CC2=CC(C=CC(=O)N(CC=3N(C4=CC=CC=C4C=3)C)C)=CN=C21 JWBSXUBRCMAXSR-UHFFFAOYSA-N 0.000 claims 1
- IYAIRPWESZQYLS-UHFFFAOYSA-N n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]-3-(1,2,3,5-tetrahydropyrido[2,3-e][1,4]oxazepin-7-yl)prop-2-enamide Chemical compound N1CCOCC2=CC(C=CC(=O)N(CC3=C(C4=CC=CC=C4O3)C)C)=CN=C21 IYAIRPWESZQYLS-UHFFFAOYSA-N 0.000 claims 1
- NQADEVLYZHKIDI-UHFFFAOYSA-N n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]-3-(4-methyl-1,2,3,5-tetrahydropyrido[2,3-e][1,4]diazepin-7-yl)prop-2-enamide;dihydrochloride Chemical compound Cl.Cl.N1CCN(C)CC2=CC(C=CC(=O)N(CC3=C(C4=CC=CC=C4O3)C)C)=CN=C21 NQADEVLYZHKIDI-UHFFFAOYSA-N 0.000 claims 1
- UEKRSCDIIGMYMD-MDWZMJQESA-N tert-butyl 7-[(e)-3-[1,2-dihydroacenaphthylen-5-ylmethyl(methyl)amino]-3-oxoprop-1-enyl]-1,2,3,5-tetrahydropyrido[2,3-e][1,4]diazepine-4-carboxylate Chemical compound N1CCN(C(=O)OC(C)(C)C)CC2=CC(/C=C/C(=O)N(CC=3C=4C=CC=C5CCC(C=45)=CC=3)C)=CN=C21 UEKRSCDIIGMYMD-MDWZMJQESA-N 0.000 claims 1
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- 229910052786 argon Inorganic materials 0.000 description 36
- 230000001580 bacterial effect Effects 0.000 description 36
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Apparatus For Disinfection Or Sterilisation (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicinal Preparation (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83205806P | 2006-07-20 | 2006-07-20 | |
| US60/832,058 | 2006-07-20 | ||
| PCT/CA2007/001277 WO2008009122A1 (en) | 2006-07-20 | 2007-07-19 | Acrylamide derivatives as fab i inhibitors |
Publications (2)
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|---|---|
| CA2658506A1 CA2658506A1 (en) | 2008-01-24 |
| CA2658506C true CA2658506C (en) | 2016-01-26 |
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|---|---|---|---|
| CA2658506A Expired - Fee Related CA2658506C (en) | 2006-07-20 | 2007-07-19 | Acrylamide derivatives as fab 1 inhibitors |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US8318720B2 (enExample) |
| EP (2) | EP2687533B1 (enExample) |
| JP (1) | JP5468899B2 (enExample) |
| CA (1) | CA2658506C (enExample) |
| IL (1) | IL196590A (enExample) |
| WO (1) | WO2008009122A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60017180T2 (de) | 1999-10-08 | 2005-12-08 | Affinium Pharmaceuticals, Inc., Toronto | Fab i inhibitoren |
| CA2444597A1 (en) * | 2001-04-06 | 2002-10-06 | Affinium Pharmaceuticals, Inc. | Fab i inhibitors |
| AU2003298937A1 (en) | 2002-12-06 | 2004-06-30 | Affinium Pharmaceuticals, Inc. | Heterocyclic compounds, methods of making them and their use in therapy |
| US8450307B2 (en) | 2004-06-04 | 2013-05-28 | Affinium Pharmaceuticals, Inc. | Therapeutic agents, and methods of making and using the same |
| WO2008009122A1 (en) | 2006-07-20 | 2008-01-24 | Affinium Pharmaceuticals, Inc. | Acrylamide derivatives as fab i inhibitors |
| EP2125802A4 (en) | 2007-02-16 | 2014-08-20 | Debiopharm Int Sa | SALTS, PRODRUGS AND POLYMORPHES OF FAB I INHIBITORS |
| FR2927331B1 (fr) | 2008-02-07 | 2011-05-20 | Centre Nat Rech Scient | Nouveaux derives anti-infectieux, leur procede de preparation, compositions pharmaceutiques les contenant et leurs utilisations en therapeutique. |
| US8394139B2 (en) * | 2008-08-29 | 2013-03-12 | Cook Medical Technologies Llc | Barbed anchors for wire stent |
| CN102470127A (zh) | 2009-08-19 | 2012-05-23 | 埃姆比特生物科学公司 | 联芳基化合物和其使用方法 |
| JP2013510834A (ja) * | 2009-11-16 | 2013-03-28 | メリテク | ［１，５］‐ジアゾシン誘導体 |
| JP5816629B2 (ja) | 2009-11-18 | 2015-11-18 | ファブ ファーマ エスエーエス | 新規の複素環式アクリルアミド及び医薬としてのその使用 |
| US20130281442A1 (en) * | 2010-06-11 | 2013-10-24 | Barry Hafkin | Compounds for Treatment of Bovine Mastitis |
| WO2012061698A2 (en) | 2010-11-05 | 2012-05-10 | Senomyx, Inc. | Compounds useful as modulators of trpm8 |
| HK1200445A1 (en) * | 2011-08-10 | 2015-08-07 | Janssen Sciences Ireland Uc | Antibacterial homopiperidinyl substituted 3,4 dihydro 1h [1,8]naphthyridinones |
| JO3611B1 (ar) | 2011-08-10 | 2020-08-27 | Janssen Sciences Ireland Uc | سايكلو بنتا (سي (بيرول 4,3 ثاني هيدرو 1 hمستبدله [8,1] نافثيريدينونات مضادة للجراثيم |
| EP2742047B1 (en) * | 2011-08-10 | 2021-05-12 | Janssen Sciences Ireland Unlimited Company | Antibacterial piperidinyl substituted 3,4-dihydro-1h-[1,8]naphthyridinones |
| DK2861608T3 (da) | 2012-06-19 | 2019-06-24 | Debiopharm Int Sa | Prodrug-derivater af (e)-n-methyl-n-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamid |
| WO2014072930A2 (en) * | 2012-11-09 | 2014-05-15 | Aurigene Discovery Technologies Limited | Fused pyridine derivatives as antibacterial agents |
| RU2723480C2 (ru) | 2015-08-31 | 2020-06-11 | Тон-А Сосио Холдингз Ко., Лтд. | Гетероарильные соединения и их применение в качестве терапевтических лекарственных средств |
| WO2017058594A1 (en) | 2015-10-01 | 2017-04-06 | Senomyx, Inc. | Compounds useful as modulators of trpm8 |
| AU2017213628B2 (en) | 2016-02-05 | 2021-07-29 | Denali Therapeutics Inc. | Inhibitors of receptor-interacting protein kinase 1 |
| BR112018016721A2 (pt) | 2016-02-26 | 2018-12-26 | Debiopharm Int Sa | uso de di-hidrogeno fosfato de {6-[(e)-3-{metil[(3-metil-1-benfofuran-2-iol)metil]amino)-3-xopro-1-en-1-il]-2-oxo-3,4-di-hidro-1,8-naftiridin-1(2h)-il}metila e composição farmacêutica para tratamento de infecções bacterianas associadas ao pé diabético |
| WO2018071343A1 (en) | 2016-10-10 | 2018-04-19 | Dong-A Socio Holdings Co., Ltd. | Heteroaryl compounds and their use as mer inhibitors |
| WO2018107060A1 (en) | 2016-12-09 | 2018-06-14 | Denali Therapeutics Inc. | Compounds, compositions and methods |
| PL3880675T3 (pl) * | 2018-11-12 | 2025-02-10 | Debiopharm International Sa | Związki antybiotykowe, sposoby ich wytwarzania, kompozycje farmaceutyczne zawierające te związki oraz ich zastosowanie |
| LT3923914T (lt) | 2019-02-14 | 2023-07-25 | Debiopharm International S.A. | Afabicino kompozicija, jos gamybos būdas |
| CA3139942A1 (en) | 2019-06-14 | 2020-12-17 | Justyna NOWAKOWSKA | Medicament and use thereof for treating bacterial infections involving biofilm |
| IL293980A (en) * | 2019-12-19 | 2022-08-01 | Debiopharm Int Sa | New compounds and their use |
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- 2007-07-19 CA CA2658506A patent/CA2658506C/en not_active Expired - Fee Related
- 2007-07-19 EP EP13177463.0A patent/EP2687533B1/en active Active
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| IL196590A (en) | 2017-03-30 |
| EP2054422A1 (en) | 2009-05-06 |
| WO2008009122A1 (en) | 2008-01-24 |
| US20100130470A1 (en) | 2010-05-27 |
| JP2010501474A (ja) | 2010-01-21 |
| US8318720B2 (en) | 2012-11-27 |
| US20130237523A1 (en) | 2013-09-12 |
| CA2658506A1 (en) | 2008-01-24 |
| EP2054422A4 (en) | 2012-10-03 |
| EP2687533B1 (en) | 2017-07-19 |
| EP2687533A2 (en) | 2014-01-22 |
| EP2687533A3 (en) | 2014-04-16 |
| JP5468899B2 (ja) | 2014-04-09 |
| IL196590A0 (en) | 2009-11-18 |
| EP2054422B1 (en) | 2017-06-14 |
| US8895545B2 (en) | 2014-11-25 |
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20190719 |