RU2404982C2 - Применение соединений пирролохинолина для уничтожения клинически латентных микроорганизмов - Google Patents
Применение соединений пирролохинолина для уничтожения клинически латентных микроорганизмов Download PDFInfo
- Publication number
- RU2404982C2 RU2404982C2 RU2008122912/04A RU2008122912A RU2404982C2 RU 2404982 C2 RU2404982 C2 RU 2404982C2 RU 2008122912/04 A RU2008122912/04 A RU 2008122912/04A RU 2008122912 A RU2008122912 A RU 2008122912A RU 2404982 C2 RU2404982 C2 RU 2404982C2
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- pyrrolo
- dihydro
- quinoline
- phenoxy
- Prior art date
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- SLHCMPVPVQSTBV-UHFFFAOYSA-N C1=CNC2=C3C=CN=C3C=CC2=C1 Chemical class C1=CNC2=C3C=CN=C3C=CC2=C1 SLHCMPVPVQSTBV-UHFFFAOYSA-N 0.000 title 1
- 244000005700 microbiome Species 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 25
- 239000004599 antimicrobial Substances 0.000 claims abstract 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 5
- 239000003814 drug Substances 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 46
- 125000001424 substituent group Chemical group 0.000 claims 40
- 229910052736 halogen Inorganic materials 0.000 claims 35
- 150000002367 halogens Chemical class 0.000 claims 35
- 125000003545 alkoxy group Chemical group 0.000 claims 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 20
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 15
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 14
- -1 R B represents H Chemical group 0.000 claims 10
- 125000000304 alkynyl group Chemical group 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000003342 alkenyl group Chemical group 0.000 claims 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 229910052740 iodine Inorganic materials 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 108010092160 Dactinomycin Proteins 0.000 claims 4
- 229930183665 actinomycin Natural products 0.000 claims 4
- 239000002671 adjuvant Substances 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- RGYMMMXHXLDZQA-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-2-yl)-4-methyl-8-phenoxy-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=C2C=3N(C4CC5=CC=CC=C5C4)CCC=3C(C)=NC2=CC=C1OC1=CC=CC=C1 RGYMMMXHXLDZQA-UHFFFAOYSA-N 0.000 claims 3
- 208000035143 Bacterial infection Diseases 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 230000000843 anti-fungal effect Effects 0.000 claims 3
- 229940121375 antifungal agent Drugs 0.000 claims 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims 3
- 239000003085 diluting agent Substances 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 2
- JVTNCEXFLROSJQ-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-2-yl)-4-methyl-6-phenoxy-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=CC=C2C=3N(C4CC5=CC=CC=C5C4)CCC=3C(C)=NC2=C1OC1=CC=CC=C1 JVTNCEXFLROSJQ-UHFFFAOYSA-N 0.000 claims 2
- TUDGJSQTQPFGPB-UHFFFAOYSA-N 1-benzyl-4-methyl-8-phenoxy-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=C2C=3N(CC=4C=CC=CC=4)CCC=3C(C)=NC2=CC=C1OC1=CC=CC=C1 TUDGJSQTQPFGPB-UHFFFAOYSA-N 0.000 claims 2
- MVIIBSQHOHBBAY-UHFFFAOYSA-N 4-methyl-8-phenoxy-1-(1-phenylethyl)-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C=1C=CC=CC=1C(C)N1CCC(C(=NC2=CC=3)C)=C1C2=CC=3OC1=CC=CC=C1 MVIIBSQHOHBBAY-UHFFFAOYSA-N 0.000 claims 2
- SLEVTVFWKZEBCZ-UHFFFAOYSA-N 4-methyl-8-phenoxy-1-(4-propan-2-ylphenyl)-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=CC(C(C)C)=CC=C1N1C(C=2C(=CC=C(OC=3C=CC=CC=3)C=2)N=C2C)=C2CC1 SLEVTVFWKZEBCZ-UHFFFAOYSA-N 0.000 claims 2
- OSKYEKWSYSWZRJ-UHFFFAOYSA-N 8-methoxy-4-methyl-1-(4-phenoxyphenyl)-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=2C3=CC(OC)=CC=C3N=C(C)C=2CCN1C(C=C1)=CC=C1OC1=CC=CC=C1 OSKYEKWSYSWZRJ-UHFFFAOYSA-N 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- DGMPVYSXXIOGJY-UHFFFAOYSA-N Fusaric acid Chemical compound CCCCC1=CC=C(C(O)=O)N=C1 DGMPVYSXXIOGJY-UHFFFAOYSA-N 0.000 claims 2
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims 2
- 229960004011 methenamine Drugs 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- RXWNCPJZOCPEPQ-NVWDDTSBSA-N puromycin Chemical compound C1=CC(OC)=CC=C1C[C@H](N)C(=O)N[C@H]1[C@@H](O)[C@H](N2C3=NC=NC(=C3N=C2)N(C)C)O[C@@H]1CO RXWNCPJZOCPEPQ-NVWDDTSBSA-N 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 claims 2
- 229960001082 trimethoprim Drugs 0.000 claims 2
- YKJYKKNCCRKFSL-RDBSUJKOSA-N (-)-anisomycin Chemical compound C1=CC(OC)=CC=C1C[C@@H]1[C@H](OC(C)=O)[C@@H](O)CN1 YKJYKKNCCRKFSL-RDBSUJKOSA-N 0.000 claims 1
- DQJCDTNMLBYVAY-ZXXIYAEKSA-N (2S,5R,10R,13R)-16-{[(2R,3S,4R,5R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-(ethylamino)-6-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-(4-aminobutyl)-10-carbamoyl-2,13-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid Chemical compound NCCCC[C@H](C(=O)N[C@@H](C)C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)C(C)O[C@@H]1[C@@H](NCC)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DQJCDTNMLBYVAY-ZXXIYAEKSA-N 0.000 claims 1
- CXNPLSGKWMLZPZ-GIFSMMMISA-N (2r,3r,6s)-3-[[(3s)-3-amino-5-[carbamimidoyl(methyl)amino]pentanoyl]amino]-6-(4-amino-2-oxopyrimidin-1-yl)-3,6-dihydro-2h-pyran-2-carboxylic acid Chemical compound O1[C@@H](C(O)=O)[C@H](NC(=O)C[C@@H](N)CCN(C)C(N)=N)C=C[C@H]1N1C(=O)N=C(N)C=C1 CXNPLSGKWMLZPZ-GIFSMMMISA-N 0.000 claims 1
- BKZOUCVNTCLNFF-IGXZVFLKSA-N (2s)-2-[(2r,3r,4s,5r,6s)-2-hydroxy-6-[(1s)-1-[(2s,5r,7s,8r,9s)-2-[(2r,5s)-5-[(2r,3s,4r,5r)-5-[(2s,3s,4s,5r,6s)-6-hydroxy-4-methoxy-3,5,6-trimethyloxan-2-yl]-4-methoxy-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,8-dimethyl-1,10-dioxaspiro[4.5]dec Chemical compound O([C@@H]1[C@@H]2O[C@H]([C@@H](C)[C@H]2OC)[C@@]2(C)O[C@H](CC2)[C@@]2(C)O[C@]3(O[C@@H]([C@H](C)[C@@H](OC)C3)[C@@H](C)[C@@H]3[C@@H]([C@H](OC)[C@@H](C)[C@](O)([C@H](C)C(O)=O)O3)C)CC2)[C@](C)(O)[C@H](C)[C@@H](OC)[C@@H]1C BKZOUCVNTCLNFF-IGXZVFLKSA-N 0.000 claims 1
- KOFBVFFPLADGGO-DUSUDKPKSA-N (3r,4s,5r,6r)-6-[(1r,2r)-1-amino-2-hydroxypropyl]oxane-2,3,4,5-tetrol Chemical compound C[C@@H](O)[C@@H](N)[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O KOFBVFFPLADGGO-DUSUDKPKSA-N 0.000 claims 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- AGNGYMCLFWQVGX-AGFFZDDWSA-N (e)-1-[(2s)-2-amino-2-carboxyethoxy]-2-diazonioethenolate Chemical compound OC(=O)[C@@H](N)CO\C([O-])=C\[N+]#N AGNGYMCLFWQVGX-AGFFZDDWSA-N 0.000 claims 1
- DVWXIUFCHHVNDT-UHFFFAOYSA-N 1-(1-benzylpiperidin-4-yl)-4-methyl-8-phenoxy-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=C2C=3N(C4CCN(CC=5C=CC=CC=5)CC4)CCC=3C(C)=NC2=CC=C1OC1=CC=CC=C1 DVWXIUFCHHVNDT-UHFFFAOYSA-N 0.000 claims 1
- QGXUAOBBZQTJPC-UHFFFAOYSA-N 1-(1-benzylpyrrolidin-3-yl)-8-methoxy-4-methyl-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=2C3=CC(OC)=CC=C3N=C(C)C=2CCN1C(C1)CCN1CC1=CC=CC=C1 QGXUAOBBZQTJPC-UHFFFAOYSA-N 0.000 claims 1
- FZNPGWDLTIHOCL-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-4-methyl-8-phenoxy-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=C2C=3N(CC4OC5=CC=CC=C5OC4)CCC=3C(C)=NC2=CC=C1OC1=CC=CC=C1 FZNPGWDLTIHOCL-UHFFFAOYSA-N 0.000 claims 1
- OEHBVJMUGBVLBC-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-8-methoxy-4-methyl-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1OC2=CC=CC=C2OC1CN1CCC2=C1C1=CC(OC)=CC=C1N=C2C OEHBVJMUGBVLBC-UHFFFAOYSA-N 0.000 claims 1
- WODUWSOPQKIYEZ-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-1-yl)-4-methyl-8-phenoxy-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=C2C=3N(C4C5=CC=CC=C5CC4)CCC=3C(C)=NC2=CC=C1OC1=CC=CC=C1 WODUWSOPQKIYEZ-UHFFFAOYSA-N 0.000 claims 1
- CCOOYLVRANBZSZ-UHFFFAOYSA-N 1-(3-methoxypropyl)-4-methyl-8-phenoxy-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound COCCCN1CCC(C(=NC2=CC=3)C)=C1C2=CC=3OC1=CC=CC=C1 CCOOYLVRANBZSZ-UHFFFAOYSA-N 0.000 claims 1
- AZDOESBFPVLBNQ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-4-methyl-8-phenoxy-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=CC(OC)=CC=C1N1C(C=2C(=CC=C(OC=3C=CC=CC=3)C=2)N=C2C)=C2CC1 AZDOESBFPVLBNQ-UHFFFAOYSA-N 0.000 claims 1
- AQXUDFZPKPULCB-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6,8-dimethoxy-4-methyl-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=2C3=CC(OC)=CC(OC)=C3N=C(C)C=2CCN1CC1CC1 AQXUDFZPKPULCB-UHFFFAOYSA-N 0.000 claims 1
- WODUWSOPQKIYEZ-AREMUKBSSA-N 1-[(1r)-2,3-dihydro-1h-inden-1-yl]-4-methyl-8-phenoxy-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=C2C=3N([C@H]4C5=CC=CC=C5CC4)CCC=3C(C)=NC2=CC=C1OC1=CC=CC=C1 WODUWSOPQKIYEZ-AREMUKBSSA-N 0.000 claims 1
- WODUWSOPQKIYEZ-SANMLTNESA-N 1-[(1s)-2,3-dihydro-1h-inden-1-yl]-4-methyl-8-phenoxy-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=C2C=3N([C@@H]4C5=CC=CC=C5CC4)CCC=3C(C)=NC2=CC=C1OC1=CC=CC=C1 WODUWSOPQKIYEZ-SANMLTNESA-N 0.000 claims 1
- NPAJRZSZPGYVKP-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)ethyl]-4-methyl-8-phenoxy-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=C2C=3N(CCC=4C=CC(Cl)=CC=4)CCC=3C(C)=NC2=CC=C1OC1=CC=CC=C1 NPAJRZSZPGYVKP-UHFFFAOYSA-N 0.000 claims 1
- CWJMKVLYTPYIPW-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)ethyl]-4-methyl-8-phenoxy-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=CC(OC)=CC=C1CCN1C(C=2C(=CC=C(OC=3C=CC=CC=3)C=2)N=C2C)=C2CC1 CWJMKVLYTPYIPW-UHFFFAOYSA-N 0.000 claims 1
- DDKUAZFTMXXZIS-UHFFFAOYSA-N 1-[3-(4-methyl-8-phenoxy-2,3-dihydropyrrolo[3,2-c]quinolin-1-yl)propyl]pyrrolidin-2-one Chemical compound C1=C2C=3N(CCCN4C(CCC4)=O)CCC=3C(C)=NC2=CC=C1OC1=CC=CC=C1 DDKUAZFTMXXZIS-UHFFFAOYSA-N 0.000 claims 1
- CSUABWIZBRPWDY-UHFFFAOYSA-N 1-[3-fluoro-4-(4-methylpiperazin-1-yl)phenyl]-8-methoxy-4-methyl-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=2C3=CC(OC)=CC=C3N=C(C)C=2CCN1C(C=C1F)=CC=C1N1CCN(C)CC1 CSUABWIZBRPWDY-UHFFFAOYSA-N 0.000 claims 1
- AOQTWHZWOJXHCJ-UHFFFAOYSA-N 1-[4-(4-fluorophenoxy)phenyl]-8-methoxy-4-methyl-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=2C3=CC(OC)=CC=C3N=C(C)C=2CCN1C(C=C1)=CC=C1OC1=CC=C(F)C=C1 AOQTWHZWOJXHCJ-UHFFFAOYSA-N 0.000 claims 1
- WIFTXZARFQYDOI-UHFFFAOYSA-N 1-benzyl-4-methyl-6-phenoxy-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=CC=C2C=3N(CC=4C=CC=CC=4)CCC=3C(C)=NC2=C1OC1=CC=CC=C1 WIFTXZARFQYDOI-UHFFFAOYSA-N 0.000 claims 1
- IGTRPTSSKHKRGR-UHFFFAOYSA-N 1-benzyl-6,8-dimethoxy-4-methyl-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=2C3=CC(OC)=CC(OC)=C3N=C(C)C=2CCN1CC1=CC=CC=C1 IGTRPTSSKHKRGR-UHFFFAOYSA-N 0.000 claims 1
- QNZGQQRIFLNEAF-UHFFFAOYSA-N 1-cyclohexyl-4-methyl-8-phenoxy-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=C2C=3N(C4CCCCC4)CCC=3C(C)=NC2=CC=C1OC1=CC=CC=C1 QNZGQQRIFLNEAF-UHFFFAOYSA-N 0.000 claims 1
- INLASFAPRUISQI-UHFFFAOYSA-N 1-cyclohexyl-8-methoxy-4-methyl-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=2C3=CC(OC)=CC=C3N=C(C)C=2CCN1C1CCCCC1 INLASFAPRUISQI-UHFFFAOYSA-N 0.000 claims 1
- UMNUCTVIDKJPPV-UHFFFAOYSA-N 1-cyclopropyl-6,8-dimethoxy-4-methyl-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=2C3=CC(OC)=CC(OC)=C3N=C(C)C=2CCN1C1CC1 UMNUCTVIDKJPPV-UHFFFAOYSA-N 0.000 claims 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- GVEZIHKRYBHEFX-MNOVXSKESA-N 13C-Cerulenin Natural products CC=CCC=CCCC(=O)[C@H]1O[C@@H]1C(N)=O GVEZIHKRYBHEFX-MNOVXSKESA-N 0.000 claims 1
- CTMXMUYXFHJAGX-UHFFFAOYSA-N 2,4-dimethyl-1-(2-methylphenyl)-8-phenoxy-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound CC1=NC=2C=CC(=CC=2C2=C1CC(N2C1=C(C=CC=C1)C)C)OC1=CC=CC=C1 CTMXMUYXFHJAGX-UHFFFAOYSA-N 0.000 claims 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 1
- CUICHUOHGNCCEZ-UHFFFAOYSA-N 2-[4-(8-methoxy-4-methyl-2,3-dihydropyrrolo[3,2-c]quinolin-1-yl)phenoxy]-n,n-dimethylethanamine Chemical compound C1=2C3=CC(OC)=CC=C3N=C(C)C=2CCN1C1=CC=C(OCCN(C)C)C=C1 CUICHUOHGNCCEZ-UHFFFAOYSA-N 0.000 claims 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- ZZRIVGZAWYEOIT-UHFFFAOYSA-N 3-(6,8-dimethoxy-4-methyl-2,3-dihydropyrrolo[3,2-c]quinolin-1-yl)-5-methylphenol Chemical compound C1=2C3=CC(OC)=CC(OC)=C3N=C(C)C=2CCN1C1=CC(C)=CC(O)=C1 ZZRIVGZAWYEOIT-UHFFFAOYSA-N 0.000 claims 1
- MBBZEMJDPTXWPF-UHFFFAOYSA-N 3-(6,8-dimethoxy-4-methyl-2,3-dihydropyrrolo[3,2-c]quinolin-1-yl)phenol Chemical compound C1=2C3=CC(OC)=CC(OC)=C3N=C(C)C=2CCN1C1=CC=CC(O)=C1 MBBZEMJDPTXWPF-UHFFFAOYSA-N 0.000 claims 1
- NPQZNMPPUASIAY-UHFFFAOYSA-N 4-(6,8-dimethoxy-4-methyl-2,3-dihydropyrrolo[3,2-c]quinolin-1-yl)phenol Chemical compound C1=2C3=CC(OC)=CC(OC)=C3N=C(C)C=2CCN1C1=CC=C(O)C=C1 NPQZNMPPUASIAY-UHFFFAOYSA-N 0.000 claims 1
- IIVINQSXIFCKDQ-UHFFFAOYSA-N 4-[4-methyl-1-(4-phenoxyphenyl)-2,3-dihydropyrrolo[3,2-c]quinolin-8-yl]morpholine Chemical compound C1CC=2C(C)=NC3=CC=C(N4CCOCC4)C=C3C=2N1C(C=C1)=CC=C1OC1=CC=CC=C1 IIVINQSXIFCKDQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
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| RU2008122912A RU2008122912A (ru) | 2009-12-20 |
| RU2404982C2 true RU2404982C2 (ru) | 2010-11-27 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2688161C2 (ru) * | 2013-07-25 | 2019-05-20 | Университет Ягеллоньски | Пирролохинолиновые производные в качестве 5-нт6 антагонистов, способ их получения и применение |
| RU2824145C1 (ru) * | 2020-05-06 | 2024-08-06 | Шанхай Юаньси Медисин Корп. | Применение производного бензизоселеназола против коронавируса и для контролирования интерстициального заболевания легких (изл), связанного с коронавирусом |
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| GB0522715D0 (en) | 2005-11-08 | 2005-12-14 | Helperby Therapeutics Ltd | New use |
| GB0709513D0 (en) * | 2007-05-17 | 2007-06-27 | Helperby Therapeutics Ltd | Topical formulations |
| US8759348B2 (en) * | 2007-05-17 | 2014-06-24 | Helperby Therapeutics Limited | Use of 4-(pyrrolidin-1-yl)quinoline compounds to kill clinically latent microorganisms |
| CA2703475A1 (en) | 2007-10-25 | 2009-04-30 | Cempra Pharmaceuticals, Inc. | Process for the preparation of macrolide antibacterial agents |
| EP2358379B1 (en) | 2008-10-24 | 2015-12-16 | Cempra Pharmaceuticals, Inc. | Biodefenses using triazole-containing macrolides |
| US9937194B1 (en) | 2009-06-12 | 2018-04-10 | Cempra Pharmaceuticals, Inc. | Compounds and methods for treating inflammatory diseases |
| RU2457208C2 (ru) * | 2009-07-06 | 2012-07-27 | Государственное образовательное учреждение высшего профессионального образования "Пермская государственная фармацевтическая академия Федерального агентства по здравоохранению и социальному развитию" (ГОУ ВПО "ПГФА Росздрава") | 1H-ПИРРОЛО[3,4-b]ХИНОЛИН-3,9(2H,4H)-ДИОНЫ, ОБЛАДАЮЩИЕ ПРОТИВОТУБЕРКУЛЕЗНОЙ АКТИВНОСТЬЮ, И СПОСОБ ИХ ПОЛУЧЕНИЯ |
| BR112012024999A2 (pt) | 2010-03-30 | 2016-07-12 | Helperby Therapeutics Ltd | combinação e uso |
| GB201013207D0 (en) | 2010-08-05 | 2010-09-22 | Helperby Therapeutics Ltd | Novel combination |
| JP2013532716A (ja) * | 2010-08-05 | 2013-08-19 | ヘルパービー セラピューティクス リミテッド | ピロロキノリン化合物と、β−ラクタム系抗微生物剤、ムピロシンまたはクロルヘキシジンとの組み合わせ |
| GB201015079D0 (en) | 2010-09-10 | 2010-10-27 | Helperby Therapeutics Ltd | Novel use |
| CA2811568A1 (en) * | 2010-10-08 | 2012-04-12 | Helperby Therapeutics Limited | Novel composition |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| RU2688161C2 (ru) * | 2013-07-25 | 2019-05-20 | Университет Ягеллоньски | Пирролохинолиновые производные в качестве 5-нт6 антагонистов, способ их получения и применение |
| RU2824145C1 (ru) * | 2020-05-06 | 2024-08-06 | Шанхай Юаньси Медисин Корп. | Применение производного бензизоселеназола против коронавируса и для контролирования интерстициального заболевания легких (изл), связанного с коронавирусом |
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