TWI592390B - 聚環狀四環素化合物 - Google Patents

Info

Publication number

TWI592390B

TWI592390B TW100110964A TW100110964A TWI592390B TW I592390 B TWI592390 B TW I592390B TW 100110964 A TW100110964 A TW 100110964A TW 100110964 A TW100110964 A TW 100110964A TW I592390 B TWI592390 B TW I592390B

Authority

TW

Taiwan

Prior art keywords

group

alkyl

compound

ring

organism

Prior art date

2010-03-31

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• -1 Polycyclic tetracycline compounds Chemical class 0.000 title claims description 76
• 239000004098 Tetracycline Substances 0.000 title claims description 76
• 229960002180 tetracycline Drugs 0.000 title claims description 76
• 229930101283 tetracycline Natural products 0.000 title claims description 76
• 235000019364 tetracycline Nutrition 0.000 title claims description 76
• 150000001875 compounds Chemical class 0.000 claims description 362
• 239000001257 hydrogen Substances 0.000 claims description 100
• 229910052739 hydrogen Inorganic materials 0.000 claims description 100
• 208000015181 infectious disease Diseases 0.000 claims description 82
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 79
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 76
• 125000000623 heterocyclic group Chemical group 0.000 claims description 70
• 238000000034 method Methods 0.000 claims description 62
• 150000003839 salts Chemical class 0.000 claims description 58
• 229910052757 nitrogen Inorganic materials 0.000 claims description 54
• 150000003522 tetracyclines Chemical class 0.000 claims description 51
• 125000001153 fluoro group Chemical group F* 0.000 claims description 39
• 239000000460 chlorine Chemical group 0.000 claims description 38
• 230000001154 acute effect Effects 0.000 claims description 36
• 241000894006 Bacteria Species 0.000 claims description 35
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 34
• 239000011737 fluorine Substances 0.000 claims description 31
• 229910052731 fluorine Inorganic materials 0.000 claims description 31
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
• 125000000217 alkyl group Chemical group 0.000 claims description 29
• 125000006413 ring segment Chemical group 0.000 claims description 28
• 229920006395 saturated elastomer Polymers 0.000 claims description 28
• 125000005843 halogen group Chemical group 0.000 claims description 24
• 125000001424 substituent group Chemical group 0.000 claims description 24
• 125000002837 carbocyclic group Chemical group 0.000 claims description 23
• 238000011282 treatment Methods 0.000 claims description 23
• 125000005842 heteroatom Chemical group 0.000 claims description 22
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 20
• 208000007764 Legionnaires' Disease Diseases 0.000 claims description 19
• 230000001580 bacterial effect Effects 0.000 claims description 19
• 229910052799 carbon Inorganic materials 0.000 claims description 19
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• 125000004452 carbocyclyl group Chemical group 0.000 claims description 18
• 125000004432 carbon atom Chemical group C* 0.000 claims description 17
• 229910052760 oxygen Inorganic materials 0.000 claims description 17
• 125000003386 piperidinyl group Chemical group 0.000 claims description 16
• 229910052717 sulfur Inorganic materials 0.000 claims description 16
• 230000008569 process Effects 0.000 claims description 15
• 241000193996 Streptococcus pyogenes Species 0.000 claims description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
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• 241000191967 Staphylococcus aureus Species 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
• 241000606768 Haemophilus influenzae Species 0.000 claims description 11
• 125000002947 alkylene group Chemical group 0.000 claims description 11
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• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 11
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
• 125000003118 aryl group Chemical group 0.000 claims description 10
• SOVUOXKZCCAWOJ-HJYUBDRYSA-N (4s,4as,5ar,12ar)-9-[[2-(tert-butylamino)acetyl]amino]-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=C(N(C)C)C=C(NC(=O)CNC(C)(C)C)C(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O SOVUOXKZCCAWOJ-HJYUBDRYSA-N 0.000 claims description 9
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• 239000003242 anti bacterial agent Substances 0.000 claims description 9
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• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
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• 229940088710 antibiotic agent Drugs 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
• 230000001225 therapeutic effect Effects 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 7
• 229940032049 enterococcus faecalis Drugs 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
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• 229940031000 streptococcus pneumoniae Drugs 0.000 claims description 6
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• 108700042778 Antimicrobial Peptides Proteins 0.000 claims description 5
• 102000044503 Antimicrobial Peptides Human genes 0.000 claims description 5
• 241000588921 Enterobacteriaceae Species 0.000 claims description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 241000589989 Helicobacter Species 0.000 claims description 5
• RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 claims description 5
• 241000187479 Mycobacterium tuberculosis Species 0.000 claims description 5
• 229960003085 meticillin Drugs 0.000 claims description 5
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
• 241000589876 Campylobacter Species 0.000 claims description 4
• 241001185363 Chlamydiae Species 0.000 claims description 4
• 241000498849 Chlamydiales Species 0.000 claims description 4
• 241000194033 Enterococcus Species 0.000 claims description 4
• 241000606790 Haemophilus Species 0.000 claims description 4
• 208000016604 Lyme disease Diseases 0.000 claims description 4
• 241000186359 Mycobacterium Species 0.000 claims description 4
• 241000204031 Mycoplasma Species 0.000 claims description 4
• 241000606651 Rickettsiales Species 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 241000605059 Bacteroidetes Species 0.000 claims description 3
• 241000589968 Borrelia Species 0.000 claims description 3
• 241001112696 Clostridia Species 0.000 claims description 3
• 241000186216 Corynebacterium Species 0.000 claims description 3
• 241000589242 Legionella pneumophila Species 0.000 claims description 3
• 241000186781 Listeria Species 0.000 claims description 3
• 241000588653 Neisseria Species 0.000 claims description 3
• 241000187654 Nocardia Species 0.000 claims description 3
• 241000186429 Propionibacterium Species 0.000 claims description 3
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• 241000589886 Treponema Species 0.000 claims description 3
• 241000607598 Vibrio Species 0.000 claims description 3
• 125000006430 alkyl cyclopropyl group Chemical group 0.000 claims description 3
• 229940124307 fluoroquinolone Drugs 0.000 claims description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 229940115932 legionella pneumophila Drugs 0.000 claims description 3
• 239000003910 polypeptide antibiotic agent Substances 0.000 claims description 3
• 229940072172 tetracycline antibiotic Drugs 0.000 claims description 3
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
• MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 claims description 3
• 241000304886 Bacilli Species 0.000 claims description 2
• 229930186147 Cephalosporin Natural products 0.000 claims description 2
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• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 2
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• MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 claims 2
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