TW201542556A - 抗菌之１，２－二氫－３ｈ－吡咯并［１，２－ｃ］咪唑－３－酮衍生物 - Google Patents

Info

Publication number

TW201542556A

TW201542556A TW104106737A TW104106737A TW201542556A TW 201542556 A TW201542556 A TW 201542556A TW 104106737 A TW104106737 A TW 104106737A TW 104106737 A TW104106737 A TW 104106737A TW 201542556 A TW201542556 A TW 201542556A

Authority

TW

Taiwan

Prior art keywords

methyl

hydroxy

pyrrolo

methylsulfonyl

imidazole

Prior art date

2014-03-04

Links

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• Global Dossier
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• 230000000844 anti-bacterial effect Effects 0.000 title abstract description 16
• XTYMYZJHPHOJAW-UHFFFAOYSA-N 1,2-dihydropyrrolo[1,2-c]imidazol-3-one Chemical class C1=CN2C(=O)NCC2=C1 XTYMYZJHPHOJAW-UHFFFAOYSA-N 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 527
• 150000003839 salts Chemical class 0.000 claims abstract description 72
• -1 1,2-dihydroxyethyl Chemical group 0.000 claims description 517
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 233
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 77
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 62
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 59
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 53
• 238000011282 treatment Methods 0.000 claims description 51
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 45
• 229910052736 halogen Inorganic materials 0.000 claims description 44
• 150000002367 halogens Chemical class 0.000 claims description 44
• 125000000217 alkyl group Chemical group 0.000 claims description 42
• 125000003545 alkoxy group Chemical group 0.000 claims description 41
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 28
• 208000035143 Bacterial infection Diseases 0.000 claims description 26
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 26
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 26
• 150000004702 methyl esters Chemical class 0.000 claims description 26
• 230000002265 prevention Effects 0.000 claims description 21
• 239000003814 drug Substances 0.000 claims description 19
• 150000002148 esters Chemical class 0.000 claims description 19
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 15
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
• FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 claims description 12
• XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical group OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 12
• 108700003601 dimethylglycine Proteins 0.000 claims description 12
• 125000005309 thioalkoxy group Chemical group 0.000 claims description 11
• 150000001412 amines Chemical class 0.000 claims description 9
• VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical group NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 8
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 7
• KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
• GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 4
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 4
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• 239000004480 active ingredient Substances 0.000 claims description 3
• 125000002252 acyl group Chemical group 0.000 claims description 3
• OTTPWWFPWBCJBS-UHFFFAOYSA-N o-(trifluoromethyl)hydroxylamine Chemical compound NOC(F)(F)F OTTPWWFPWBCJBS-UHFFFAOYSA-N 0.000 claims description 3
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
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• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 1
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 1
• CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical group OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims 1
• LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims 1
• TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
• 229940095102 methyl benzoate Drugs 0.000 claims 1
• 229940116269 uric acid Drugs 0.000 claims 1
• 238000000034 method Methods 0.000 description 222
• 238000005481 NMR spectroscopy Methods 0.000 description 219
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 211
• 238000002360 preparation method Methods 0.000 description 209
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 180
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 116
• 239000000203 mixture Substances 0.000 description 116
• 235000019439 ethyl acetate Nutrition 0.000 description 106
• 239000000243 solution Substances 0.000 description 105
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 101
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 95
• 238000006243 chemical reaction Methods 0.000 description 94
• 239000007787 solid Substances 0.000 description 88
• 239000000543 intermediate Substances 0.000 description 75
• 239000011541 reaction mixture Substances 0.000 description 57
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 52
• 239000012044 organic layer Substances 0.000 description 50
• 239000012267 brine Substances 0.000 description 36
• 239000010410 layer Substances 0.000 description 36
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 36
• 239000002904 solvent Substances 0.000 description 34
• 241000894006 Bacteria Species 0.000 description 33
• 239000002253 acid Substances 0.000 description 33
• 238000004128 high performance liquid chromatography Methods 0.000 description 31
• 239000000706 filtrate Substances 0.000 description 28
• 229910052740 iodine Inorganic materials 0.000 description 28
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
• 238000002953 preparative HPLC Methods 0.000 description 25
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
• 208000015181 infectious disease Diseases 0.000 description 24
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
• IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 23
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 22
• 239000011630 iodine Substances 0.000 description 22
• 229920006395 saturated elastomer Polymers 0.000 description 22
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
• 125000004432 carbon atom Chemical group C* 0.000 description 20
• 230000002829 reductive effect Effects 0.000 description 20
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 20
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 18
• 206010057190 Respiratory tract infections Diseases 0.000 description 18
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• 239000011737 fluorine Substances 0.000 description 18
• 229910052731 fluorine Inorganic materials 0.000 description 18
• 229910052757 nitrogen Inorganic materials 0.000 description 18
• 238000000746 purification Methods 0.000 description 17
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 16
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• 239000003480 eluent Substances 0.000 description 16
• 239000011734 sodium Substances 0.000 description 16
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• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 15
• 239000002585 base Substances 0.000 description 15
• WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 15
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• 241000589517 Pseudomonas aeruginosa Species 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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