EA007490B1 - N-арил-2-оксазолидинон-5-карбоксамиды, их производные и их применение в качестве антибактериальных средств - Google Patents

Info

Publication number

EA007490B1

EA007490B1 EA200400893A EA200400893A EA007490B1 EA 007490 B1 EA007490 B1 EA 007490B1 EA 200400893 A EA200400893 A EA 200400893A EA 200400893 A EA200400893 A EA 200400893A EA 007490 B1 EA007490 B1 EA 007490B1

Authority

EA

Eurasian Patent Office

Prior art keywords

oxo

dihydro

methyl

phenyl

oxazolidinecarboxamide

Prior art date

2002-02-25

Links

• Espacenet
• Global Dossier
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• 230000000844 anti-bacterial effect Effects 0.000 title description 6
• 229940088710 antibiotic agent Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 371
• 238000000034 method Methods 0.000 claims description 186
• -1 2,3-dihydro-6-benzothiazolyl Chemical group 0.000 claims description 165
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 94
• 125000000217 alkyl group Chemical group 0.000 claims description 34
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
• 125000001424 substituent group Chemical group 0.000 claims description 32
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
• 239000008194 pharmaceutical composition Substances 0.000 claims description 25
• 150000003839 salts Chemical class 0.000 claims description 20
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 12
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
• 208000015181 infectious disease Diseases 0.000 claims description 10
• 125000001624 naphthyl group Chemical group 0.000 claims description 10
• 241000124008 Mammalia Species 0.000 claims description 9
• 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 8
• 230000000813 microbial effect Effects 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims description 6
• 230000037396 body weight Effects 0.000 claims description 5
• 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims description 5
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 229910052796 boron Inorganic materials 0.000 claims description 3
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
• 150000002367 halogens Chemical class 0.000 claims 10
• 125000001475 halogen functional group Chemical group 0.000 claims 2
• 239000003242 anti bacterial agent Substances 0.000 abstract description 4
• 125000001072 heteroaryl group Chemical group 0.000 abstract description 2
• 125000003107 substituted aryl group Chemical group 0.000 abstract description 2
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 571
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 230
• 239000000203 mixture Substances 0.000 description 219
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 180
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 170
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 159
• 239000000243 solution Substances 0.000 description 155
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 151
• 230000002829 reductive effect Effects 0.000 description 145
• 238000002360 preparation method Methods 0.000 description 144
• 239000011541 reaction mixture Substances 0.000 description 126
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 120
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 96
• 239000007787 solid Substances 0.000 description 91
• 235000002639 sodium chloride Nutrition 0.000 description 80
• 239000000741 silica gel Substances 0.000 description 77
• 229910002027 silica gel Inorganic materials 0.000 description 77
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 71
• 238000005160 1H NMR spectroscopy Methods 0.000 description 70
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 69
• 239000002904 solvent Substances 0.000 description 68
• 239000011780 sodium chloride Substances 0.000 description 63
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 62
• 239000000543 intermediate Substances 0.000 description 58
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
• 239000000725 suspension Substances 0.000 description 57
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 52
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 47
• 239000000047 product Substances 0.000 description 47
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 43
• 239000012074 organic phase Substances 0.000 description 40
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 39
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 37
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 37
• 238000000746 purification Methods 0.000 description 37
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 34
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 34
• 238000004587 chromatography analysis Methods 0.000 description 33
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 32
• 125000005843 halogen group Chemical group 0.000 description 32
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 31
• 238000001914 filtration Methods 0.000 description 30
• 239000010410 layer Substances 0.000 description 29
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
• 238000006243 chemical reaction Methods 0.000 description 28
• 238000011282 treatment Methods 0.000 description 27
• 239000003054 catalyst Substances 0.000 description 25
• 238000003756 stirring Methods 0.000 description 25
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 24
• 125000000623 heterocyclic group Chemical group 0.000 description 24
• 125000000392 cycloalkenyl group Chemical group 0.000 description 23
• 239000000706 filtrate Substances 0.000 description 23
• 125000003118 aryl group Chemical group 0.000 description 22
• 239000012043 crude product Substances 0.000 description 22
• 238000000354 decomposition reaction Methods 0.000 description 22
• 235000019441 ethanol Nutrition 0.000 description 22
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• 239000012044 organic layer Substances 0.000 description 21
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
• 239000003480 eluent Substances 0.000 description 20
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 19
• 239000007788 liquid Substances 0.000 description 19
• 229910052757 nitrogen Inorganic materials 0.000 description 19
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
• 239000003814 drug Substances 0.000 description 18
• 239000002244 precipitate Substances 0.000 description 18
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
• 229910021529 ammonia Inorganic materials 0.000 description 17
• 235000019270 ammonium chloride Nutrition 0.000 description 16
• 229940079593 drug Drugs 0.000 description 16
• 238000003818 flash chromatography Methods 0.000 description 16
• 239000001257 hydrogen Substances 0.000 description 16
• 229910052739 hydrogen Inorganic materials 0.000 description 16
• MCVFFRWZNYZUIJ-UHFFFAOYSA-M lithium;trifluoromethanesulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)F MCVFFRWZNYZUIJ-UHFFFAOYSA-M 0.000 description 16
• 229920006395 saturated elastomer Polymers 0.000 description 16
• 239000002253 acid Substances 0.000 description 15
• 150000001414 amino alcohols Chemical class 0.000 description 15
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
• 239000003921 oil Substances 0.000 description 15
• 235000019198 oils Nutrition 0.000 description 15
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
• 239000012298 atmosphere Substances 0.000 description 14
• 238000010828 elution Methods 0.000 description 14
• 230000003993 interaction Effects 0.000 description 14
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
• AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
• 239000003153 chemical reaction reagent Substances 0.000 description 13
• 229910052740 iodine Inorganic materials 0.000 description 13
• DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 13
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• 239000002585 base Substances 0.000 description 12
• 238000002347 injection Methods 0.000 description 12
• 239000007924 injection Substances 0.000 description 12
• 239000002504 physiological saline solution Substances 0.000 description 12
• 238000011176 pooling Methods 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• 239000008346 aqueous phase Substances 0.000 description 11
• 125000000547 substituted alkyl group Chemical group 0.000 description 11
• 150000003462 sulfoxides Chemical class 0.000 description 11
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 10
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• 239000000651 prodrug Substances 0.000 description 10
• 229940002612 prodrug Drugs 0.000 description 10
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• 238000001953 recrystallisation Methods 0.000 description 10
• 238000010992 reflux Methods 0.000 description 10
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• 238000005406 washing Methods 0.000 description 10
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• 239000011630 iodine Substances 0.000 description 9
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• 239000004480 active ingredient Substances 0.000 description 8
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• 238000002953 preparative HPLC Methods 0.000 description 7
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• 239000002002 slurry Substances 0.000 description 7
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
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• QITPMSSAFSZYOP-UHFFFAOYSA-N 6-nitro-3h-1,3-benzothiazol-2-one Chemical class C1=C([N+]([O-])=O)C=C2SC(O)=NC2=C1 QITPMSSAFSZYOP-UHFFFAOYSA-N 0.000 description 6
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• 238000004128 high performance liquid chromatography Methods 0.000 description 6
• 229910052742 iron Inorganic materials 0.000 description 6
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
• 238000007911 parenteral administration Methods 0.000 description 6
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• 239000003381 stabilizer Substances 0.000 description 6
• 125000005555 sulfoximide group Chemical group 0.000 description 6
• OVRJVKCZJCNSOW-UHFFFAOYSA-N thian-4-one Chemical compound O=C1CCSCC1 OVRJVKCZJCNSOW-UHFFFAOYSA-N 0.000 description 6
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• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
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• 238000003786 synthesis reaction Methods 0.000 description 5
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