JP2008519788A5 - - Google Patents

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Publication number

JP2008519788A5

JP2008519788A5 JP2007540573A JP2007540573A JP2008519788A5 JP 2008519788 A5 JP2008519788 A5 JP 2008519788A5 JP 2007540573 A JP2007540573 A JP 2007540573A JP 2007540573 A JP2007540573 A JP 2007540573A JP 2008519788 A5 JP2008519788 A5 JP 2008519788A5

Authority

JP

Japan

Prior art keywords

dihydro

oxo

carboxy

dimethylamino

erythromycin

Prior art date

2005-11-09

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.)

Withdrawn

Links

• Espacenet
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• -1 3-carboxy-1,4-dihydro-1-dimethylamino-4-oxo-6-quinolinyl Chemical group 0.000 claims 51
• 125000000217 alkyl group Chemical group 0.000 claims 35
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 28
• 229960002626 clarithromycin Drugs 0.000 claims 24
• 229960003276 erythromycin Drugs 0.000 claims 24
• 229910052739 hydrogen Inorganic materials 0.000 claims 23
• 239000001257 hydrogen Substances 0.000 claims 23
• 150000001875 compounds Chemical class 0.000 claims 20
• 125000006308 propyl amino group Chemical group 0.000 claims 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 13
• 125000003545 alkoxy group Chemical group 0.000 claims 11
• 125000003118 aryl group Chemical group 0.000 claims 10
• 150000002431 hydrogen Chemical class 0.000 claims 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
• 125000000623 heterocyclic group Chemical group 0.000 claims 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
• 229910052736 halogen Inorganic materials 0.000 claims 6
• 150000002367 halogens Chemical class 0.000 claims 6
• 125000001072 heteroaryl group Chemical group 0.000 claims 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims 5
• 125000004122 cyclic group Chemical group 0.000 claims 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
• 125000003342 alkenyl group Chemical group 0.000 claims 4
• 229960004099 azithromycin Drugs 0.000 claims 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 4
• 238000000034 method Methods 0.000 claims 4
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 4
• 229910052757 nitrogen Inorganic materials 0.000 claims 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
• ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 4
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 3
• 208000035143 Bacterial infection Diseases 0.000 claims 3
• MNLAVFKVRUQAKW-UHFFFAOYSA-N VR nerve agent Chemical compound CCN(CC)CCSP(C)(=O)OCC(C)C MNLAVFKVRUQAKW-UHFFFAOYSA-N 0.000 claims 3
• 125000004429 atom Chemical group 0.000 claims 3
• 208000022362 bacterial infectious disease Diseases 0.000 claims 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
• 241001465754 Metazoa Species 0.000 claims 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
• 239000002253 acid Substances 0.000 claims 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
• 150000001540 azides Chemical class 0.000 claims 2
• 125000000753 cycloalkyl group Chemical group 0.000 claims 2
• 125000005842 heteroatom Chemical group 0.000 claims 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
• 229910052760 oxygen Inorganic materials 0.000 claims 2
• 239000001301 oxygen Substances 0.000 claims 2
• 230000002265 prevention Effects 0.000 claims 2
• 125000006239 protecting group Chemical group 0.000 claims 2
• 150000003839 salts Chemical class 0.000 claims 2
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
• 229910052717 sulfur Inorganic materials 0.000 claims 2
• 239000011593 sulfur Chemical group 0.000 claims 2
• 230000009885 systemic effect Effects 0.000 claims 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
• NPDLYUOYAGBHFB-WDSKDSINSA-N Asn-Arg Chemical group NC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N NPDLYUOYAGBHFB-WDSKDSINSA-N 0.000 claims 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
• 125000003302 alkenyloxy group Chemical group 0.000 claims 1
• 125000000304 alkynyl group Chemical group 0.000 claims 1
• 150000001412 amines Chemical class 0.000 claims 1
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
• 239000003054 catalyst Substances 0.000 claims 1
• 239000003638 chemical reducing agent Substances 0.000 claims 1
• 229950010035 davercin Drugs 0.000 claims 1
• 239000003085 diluting agent Substances 0.000 claims 1
• 239000003814 drug Substances 0.000 claims 1
• TYQXKHPOXXXCTP-CSLYCKPJSA-N erythromycin A 2'-propanoate 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)OC(=O)CC)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 TYQXKHPOXXXCTP-CSLYCKPJSA-N 0.000 claims 1
• 229950001028 erythromycin propionate Drugs 0.000 claims 1
• VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims 1
• 239000011737 fluorine Substances 0.000 claims 1
• 229910052731 fluorine Inorganic materials 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
• 150000002923 oximes Chemical class 0.000 claims 1
• 239000008194 pharmaceutical composition Substances 0.000 claims 1
• 239000000546 pharmaceutical excipient Substances 0.000 claims 1
• 125000001424 substituent group Chemical group 0.000 claims 1
• 238000002560 therapeutic procedure Methods 0.000 claims 1
• 125000004001 thioalkyl group Chemical group 0.000 claims 1