TW201609641A - 抗菌１ｈ－吲唑及１ｈ－吲哚衍生物 - Google Patents

Info

Publication number

TW201609641A

TW201609641A TW103144395A TW103144395A TW201609641A TW 201609641 A TW201609641 A TW 201609641A TW 103144395 A TW103144395 A TW 103144395A TW 103144395 A TW103144395 A TW 103144395A TW 201609641 A TW201609641 A TW 201609641A

Authority

TW

Taiwan

Prior art keywords

hydroxy

methyl

butanamine

methylsulfonyl

compound

Prior art date

2013-12-19

Links

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• 230000000844 anti-bacterial effect Effects 0.000 title abstract description 13
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title description 3
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 412
• -1 trifluoromethoxy, amino Chemical group 0.000 claims abstract description 279
• 150000003839 salts Chemical class 0.000 claims abstract description 67
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 47
• 150000002367 halogens Chemical class 0.000 claims abstract description 47
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 24
• 125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 16
• 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims abstract description 16
• 125000005309 thioalkoxy group Chemical group 0.000 claims abstract description 16
• 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims abstract description 6
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 157
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 43
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 38
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 37
• 238000011282 treatment Methods 0.000 claims description 33
• 125000000217 alkyl group Chemical group 0.000 claims description 32
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 26
• 208000035143 Bacterial infection Diseases 0.000 claims description 26
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 26
• 239000002253 acid Substances 0.000 claims description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 18
• 230000002265 prevention Effects 0.000 claims description 18
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 17
• 229910052731 fluorine Inorganic materials 0.000 claims description 17
• 239000011737 fluorine Substances 0.000 claims description 17
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
• 150000004702 methyl esters Chemical class 0.000 claims description 13
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
• FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 claims description 10
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• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 125000003277 amino group Chemical group 0.000 claims description 5
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• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
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• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 3
• 239000004480 active ingredient Substances 0.000 claims description 3
• JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims description 3
• JKTORXLUQLQJCM-UHFFFAOYSA-N 4-phosphonobutylphosphonic acid Chemical compound OP(O)(=O)CCCCP(O)(O)=O JKTORXLUQLQJCM-UHFFFAOYSA-N 0.000 claims description 2
• 239000004471 Glycine Substances 0.000 claims description 2
• 150000001412 amines Chemical class 0.000 claims description 2
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 2
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
• 208000027096 gram-negative bacterial infections Diseases 0.000 claims description 2
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
• WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims 1
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
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• 125000004103 aminoalkyl group Chemical group 0.000 abstract description 6
• 125000005113 hydroxyalkoxy group Chemical group 0.000 abstract description 5
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• 125000005083 alkoxyalkoxy group Chemical group 0.000 abstract description 2
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
• 238000005481 NMR spectroscopy Methods 0.000 description 131
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• 238000002360 preparation method Methods 0.000 description 122
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 105
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• 239000007858 starting material Substances 0.000 description 65
• 238000006243 chemical reaction Methods 0.000 description 61
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• 239000011541 reaction mixture Substances 0.000 description 52
• 239000000543 intermediate Substances 0.000 description 50
• 239000007787 solid Substances 0.000 description 44
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• 125000004432 carbon atom Chemical group C* 0.000 description 27
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 27
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• 238000004128 high performance liquid chromatography Methods 0.000 description 24
• 229910052740 iodine Inorganic materials 0.000 description 24
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 23
• 239000002904 solvent Substances 0.000 description 23
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 20
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• 239000011630 iodine Substances 0.000 description 20
• 125000006239 protecting group Chemical group 0.000 description 19
• 230000002829 reductive effect Effects 0.000 description 19
• 239000003242 anti bacterial agent Substances 0.000 description 17
• 239000011734 sodium Substances 0.000 description 15
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 14
• 229940088710 antibiotic agent Drugs 0.000 description 14
• 230000008878 coupling Effects 0.000 description 14
• 238000010168 coupling process Methods 0.000 description 14
• 238000005859 coupling reaction Methods 0.000 description 14
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
• 241000588747 Klebsiella pneumoniae Species 0.000 description 13
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical class BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
• 229910052794 bromium Chemical class 0.000 description 13
• 239000003921 oil Substances 0.000 description 13
• 235000019198 oils Nutrition 0.000 description 13
• 238000002953 preparative HPLC Methods 0.000 description 13
• 238000000746 purification Methods 0.000 description 13
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• IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 12
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• 238000000926 separation method Methods 0.000 description 11
• 239000002585 base Substances 0.000 description 10
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