JP2014525451A5 - - Google Patents
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- JP2014525451A5 JP2014525451A5 JP2014528555A JP2014528555A JP2014525451A5 JP 2014525451 A5 JP2014525451 A5 JP 2014525451A5 JP 2014528555 A JP2014528555 A JP 2014528555A JP 2014528555 A JP2014528555 A JP 2014528555A JP 2014525451 A5 JP2014525451 A5 JP 2014525451A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- amino
- methyl
- oxo
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- 125000000217 alkyl group Chemical group 0.000 claims 244
- -1 hydroxyl - amino, hydroxyl Chemical group 0.000 claims 142
- 125000003118 aryl group Chemical group 0.000 claims 46
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 39
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 35
- 125000003282 alkyl amino group Chemical group 0.000 claims 31
- 125000000623 heterocyclic group Chemical group 0.000 claims 26
- 125000001072 heteroaryl group Chemical group 0.000 claims 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 239000001257 hydrogen Substances 0.000 claims 17
- 125000003545 alkoxy group Chemical group 0.000 claims 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
- 150000002431 hydrogen Chemical class 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- 239000008194 pharmaceutical composition Substances 0.000 claims 12
- PRLAXFQDDSSHNY-UHFFFAOYSA-N 1h-indole-3-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC=C2C(C(=O)O)=CNC2=C1 PRLAXFQDDSSHNY-UHFFFAOYSA-N 0.000 claims 8
- 239000003242 anti bacterial agent Substances 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 208000035143 Bacterial infection Diseases 0.000 claims 6
- JXYPFOQQDWNPDV-UHFFFAOYSA-N Cl.OC(=O)c1cnc2cc3cccccc3cc12 Chemical compound Cl.OC(=O)c1cnc2cc3cccccc3cc12 JXYPFOQQDWNPDV-UHFFFAOYSA-N 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 6
- 208000022362 bacterial infectious disease Diseases 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 6
- 241000894006 Bacteria Species 0.000 claims 5
- 125000001769 aryl amino group Chemical group 0.000 claims 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 5
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 4
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims 3
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims 3
- 125000005960 1,4-diazepanyl group Chemical group 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- JSOILMJIWRVSNX-UHFFFAOYSA-N Cl.N1=C2C(CC(=C1)C(=O)O)=CC=CC=C2 Chemical compound Cl.N1=C2C(CC(=C1)C(=O)O)=CC=CC=C2 JSOILMJIWRVSNX-UHFFFAOYSA-N 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 230000003115 biocidal effect Effects 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
- IBTWUVRCFHJPKN-UHFFFAOYSA-N hydron;pyridine-3-carboxylic acid;chloride Chemical compound Cl.OC(=O)C1=CC=CN=C1 IBTWUVRCFHJPKN-UHFFFAOYSA-N 0.000 claims 3
- KMAKOBLIOCQGJP-UHFFFAOYSA-N indole-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CNC2=C1 KMAKOBLIOCQGJP-UHFFFAOYSA-N 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 3
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 241001156739 Actinobacteria <phylum> Species 0.000 claims 2
- 241000606125 Bacteroides Species 0.000 claims 2
- 241000606161 Chlamydia Species 0.000 claims 2
- 241000194032 Enterococcus faecalis Species 0.000 claims 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims 2
- 241000192142 Proteobacteria Species 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 229930189077 Rifamycin Natural products 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000006319 alkynyl amino group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 229940032049 enterococcus faecalis Drugs 0.000 claims 2
- AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 claims 2
- 239000012458 free base Substances 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000005241 heteroarylamino group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 229960003292 rifamycin Drugs 0.000 claims 2
- HJYYPODYNSCCOU-ODRIEIDWSA-N rifamycin SV Chemical compound OC1=C(C(O)=C2C)C3=C(O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O HJYYPODYNSCCOU-ODRIEIDWSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 241000894007 species Species 0.000 claims 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- CVCQAQVBOPNTFI-AAONGDSNSA-N (3r,4r,5s,6r)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol;sulfuric acid Chemical compound OS(O)(=O)=O.N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O.N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O CVCQAQVBOPNTFI-AAONGDSNSA-N 0.000 claims 1
- VCOPTHOUUNAYKQ-WBTCAYNUSA-N (3s)-3,6-diamino-n-[[(2s,5s,8e,11s,15s)-15-amino-11-[(6r)-2-amino-1,4,5,6-tetrahydropyrimidin-6-yl]-8-[(carbamoylamino)methylidene]-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentazacyclohexadec-5-yl]methyl]hexanamide;(3s)-3,6-diamino-n-[[(2s,5s,8 Chemical compound N1C(=O)\C(=C/NC(N)=O)NC(=O)[C@H](CNC(=O)C[C@@H](N)CCCN)NC(=O)[C@H](C)NC(=O)[C@@H](N)CNC(=O)[C@@H]1[C@@H]1NC(N)=NCC1.N1C(=O)\C(=C/NC(N)=O)NC(=O)[C@H](CNC(=O)C[C@@H](N)CCCN)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CNC(=O)[C@@H]1[C@@H]1NC(N)=NCC1 VCOPTHOUUNAYKQ-WBTCAYNUSA-N 0.000 claims 1
- SGKRLCUYIXIAHR-AKNGSSGZSA-N (4s,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-AKNGSSGZSA-N 0.000 claims 1
- FFTVPQUHLQBXQZ-KVUCHLLUSA-N (4s,4as,5ar,12ar)-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=CC(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 FFTVPQUHLQBXQZ-KVUCHLLUSA-N 0.000 claims 1
- 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 1
- OURIMSKXUOYJRD-CFILVAQYSA-N (9R,10S)-15-(ethylaminomethyl)-6,9,10-trihydroxy-14-methyl-4-oxo-3,14-diazatetracyclo[9.7.0.02,7.013,17]octadeca-1(11),2(7),5,12,15,17-hexaene-5-carboxylic acid hydrochloride Chemical compound Cl.C1=C2N(C)C(CNCC)=CC2=CC2=C1[C@H](O)[C@H](O)CC1=C2NC(=O)C(C(O)=O)=C1O OURIMSKXUOYJRD-CFILVAQYSA-N 0.000 claims 1
- MINDHVHHQZYEEK-UHFFFAOYSA-N (E)-(2S,3R,4R,5S)-5-[(2S,3S,4S,5S)-2,3-epoxy-5-hydroxy-4-methylhexyl]tetrahydro-3,4-dihydroxy-(beta)-methyl-2H-pyran-2-crotonic acid ester with 9-hydroxynonanoic acid Natural products CC(O)C(C)C1OC1CC1C(O)C(O)C(CC(C)=CC(=O)OCCCCCCCCC(O)=O)OC1 MINDHVHHQZYEEK-UHFFFAOYSA-N 0.000 claims 1
- RXZBMPWDPOLZGW-XMRMVWPWSA-N (E)-roxithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N/OCOCCOC)/[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 RXZBMPWDPOLZGW-XMRMVWPWSA-N 0.000 claims 1
- XUBOMFCQGDBHNK-JTQLQIEISA-N (S)-gatifloxacin Chemical compound FC1=CC(C(C(C(O)=O)=CN2C3CC3)=O)=C2C(OC)=C1N1CCN[C@@H](C)C1 XUBOMFCQGDBHNK-JTQLQIEISA-N 0.000 claims 1
- 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims 1
- FEPGHUPFTLRZIC-UHFFFAOYSA-N 13-(ethylaminomethyl)-6-hydroxy-12-methyl-4-oxo-3,12-diazatetracyclo[7.7.0.02,7.011,15]hexadeca-1(9),2(7),5,10,13,15-hexaene-5-carboxylic acid hydrochloride Chemical compound Cl.C1C(C(=C(C(O)=O)C(=O)N2)O)=C2C2=C1C=C(N(C(CNCC)=C1)C)C1=C2 FEPGHUPFTLRZIC-UHFFFAOYSA-N 0.000 claims 1
- LMEUTEOPYTZWOA-UHFFFAOYSA-N 14-(ethylamino)-6-hydroxy-4-oxo-3-azatricyclo[10.4.0.02,7]hexadeca-1(12),2(7),5,13,15-pentaene-5-carboxylic acid Chemical compound C=1C(NCC)=CC=C2C=1CCCCC1=C2NC(=O)C(C(O)=O)=C1O LMEUTEOPYTZWOA-UHFFFAOYSA-N 0.000 claims 1
- FFKJRDNEWOASPJ-UHFFFAOYSA-N 14-(ethylaminomethyl)-6-hydroxy-15-methyl-4-oxo-3,15-diazatetracyclo[9.7.0.02,7.012,16]octadeca-1(11),2(7),5,12(16),13,17-hexaene-5-carboxylic acid hydrochloride Chemical compound Cl.C12=CC=C3N(C)C(CNCC)=CC3=C2CCCC2=C1NC(=O)C(C(O)=O)=C2O FFKJRDNEWOASPJ-UHFFFAOYSA-N 0.000 claims 1
- ITQKTRVSBSIUFK-UHFFFAOYSA-N 14-methyl-4-oxo-15-[(propan-2-ylamino)methyl]-3,14-diazatetracyclo[9.7.0.02,7.013,17]octadeca-1(11),2(7),5,12,15,17-hexaene-5-carboxylic acid hydrochloride Chemical compound Cl.C1=C2N(C)C(CNC(C)C)=CC2=CC2=C1CCCC1=C2NC(=O)C(C(O)=O)=C1 ITQKTRVSBSIUFK-UHFFFAOYSA-N 0.000 claims 1
- OTXWRVMPBWJZST-UHFFFAOYSA-N 15-(aminomethyl)-6-hydroxy-14-methyl-4-oxo-3,14-diazatetracyclo[9.7.0.02,7.013,17]octadeca-1(11),2(7),5,12,15,17-hexaene-5-carboxylic acid hydrochloride Chemical compound Cl.C1=C2N(C)C(CN)=CC2=CC2=C1CCCC1=C2NC(=O)C(C(O)=O)=C1O OTXWRVMPBWJZST-UHFFFAOYSA-N 0.000 claims 1
- UYULKWDHTZPMPZ-UHFFFAOYSA-N 15-(azetidin-1-ylmethyl)-14-methyl-4-oxo-3,14-diazatetracyclo[9.7.0.02,7.013,17]octadeca-1(11),2(7),5,12,15,17-hexaene-5-carboxylic acid hydrochloride Chemical compound Cl.C=1C2=CC(C=3NC(=O)C(C(O)=O)=CC=3CCC3)=C3C=C2N(C)C=1CN1CCC1 UYULKWDHTZPMPZ-UHFFFAOYSA-N 0.000 claims 1
- XSQVQZJVNJJPHC-UHFFFAOYSA-N 15-(azetidin-1-ylmethyl)-6-hydroxy-14-methyl-4-oxo-3,14-diazatetracyclo[9.7.0.02,7.013,17]octadeca-1(11),2(7),5,12,15,17-hexaene-5-carboxylic acid hydrochloride Chemical compound Cl.C=1C2=CC(C=3NC(=O)C(C(O)=O)=C(O)C=3CCC3)=C3C=C2N(C)C=1CN1CCC1 XSQVQZJVNJJPHC-UHFFFAOYSA-N 0.000 claims 1
- CBGHZXRNKIMLGT-UHFFFAOYSA-N 15-(butylaminomethyl)-6-hydroxy-14-methyl-4-oxo-3,14-diazatetracyclo[9.7.0.02,7.013,17]octadeca-1(11),2(7),5,12,15,17-hexaene-5-carboxylic acid hydrochloride Chemical compound Cl.C1=C2N(C)C(CNCCCC)=CC2=CC2=C1CCCC1=C2NC(=O)C(C(O)=O)=C1O CBGHZXRNKIMLGT-UHFFFAOYSA-N 0.000 claims 1
- PURPUJKNHAMTPS-UHFFFAOYSA-N 15-(diethylaminomethyl)-6-hydroxy-14-methyl-4-oxo-3,14-diazatetracyclo[9.7.0.02,7.013,17]octadeca-1(11),2(7),5,12,15,17-hexaene-5-carboxylic acid hydrochloride Chemical compound Cl.C1=C2N(C)C(CN(CC)CC)=CC2=CC2=C1CCCC1=C2NC(=O)C(C(O)=O)=C1O PURPUJKNHAMTPS-UHFFFAOYSA-N 0.000 claims 1
- OMEWUIBSOBWJLW-UHFFFAOYSA-N 15-(ethylaminomethyl)-14-methyl-4-oxo-3,14-diazatetracyclo[9.7.0.02,7.013,17]octadeca-1(11),2(7),5,12,15,17-hexaene-5-carboxylic acid hydrochloride Chemical compound Cl.C1=C2N(C)C(CNCC)=CC2=CC2=C1CCCC1=C2NC(=O)C(C(O)=O)=C1 OMEWUIBSOBWJLW-UHFFFAOYSA-N 0.000 claims 1
- LEYUVFSNQXJBMP-UHFFFAOYSA-N 15-(ethylaminomethyl)-6-hydroxy-10,14-dimethyl-4-oxo-3,14-diazatetracyclo[9.7.0.02,7.013,17]octadeca-1(11),2(7),5,9,12,15,17-heptaene-5-carboxylic acid hydrochloride Chemical compound Cl.C1=C2N(C)C(CNCC)=CC2=CC2=C1C(C)=CCC1=C2NC(=O)C(C(O)=O)=C1O LEYUVFSNQXJBMP-UHFFFAOYSA-N 0.000 claims 1
- VFXIYGGRKNHQEB-UHFFFAOYSA-N 15-(ethylaminomethyl)-6-hydroxy-14-methyl-4-oxo-3,10,14-triazatetracyclo[9.7.0.02,7.013,17]octadeca-1(11),2(7),5,12,15,17-hexaene-5-carboxylic acid hydrochloride Chemical compound Cl.C1=C2N(C)C(CNCC)=CC2=CC2=C1NCCC1=C2NC(=O)C(C(O)=O)=C1O VFXIYGGRKNHQEB-UHFFFAOYSA-N 0.000 claims 1
- UMDSNNBWTQPXTE-UHFFFAOYSA-N 15-(ethylaminomethyl)-6-hydroxy-14-methyl-4-oxo-3,14-diazatetracyclo[9.7.0.02,7.013,17]octadeca-1(11),2(7),5,12,15,17-hexaene-5-carboxylic acid hydrochloride Chemical compound Cl.C1=C2N(C)C(CNCC)=CC2=CC2=C1CCCC1=C2NC(=O)C(C(O)=O)=C1O UMDSNNBWTQPXTE-UHFFFAOYSA-N 0.000 claims 1
- ULBYZQCXLQMMGE-UHFFFAOYSA-N 15-[(3-acetamidopyrrolidin-1-yl)methyl]-6-hydroxy-14-methyl-4-oxo-3,14-diazatetracyclo[9.7.0.02,7.013,17]octadeca-1(11),2(7),5,12,15,17-hexaene-5-carboxylic acid hydrochloride Chemical compound Cl.C1C(NC(=O)C)CCN1CC(N(C1=C2)C)=CC1=CC1=C2CCCC2=C1NC(=O)C(C(O)=O)=C2O ULBYZQCXLQMMGE-UHFFFAOYSA-N 0.000 claims 1
- BACNPGTXNPGTRI-UHFFFAOYSA-N 15-[(benzylamino)methyl]-6-hydroxy-14-methyl-4-oxo-3,14-diazatetracyclo[9.7.0.02,7.013,17]octadeca-1(11),2(7),5,12,15,17-hexaene-5-carboxylic acid hydrochloride Chemical compound Cl.C=1C2=CC(C=3NC(=O)C(C(O)=O)=C(O)C=3CCC3)=C3C=C2N(C)C=1CNCC1=CC=CC=C1 BACNPGTXNPGTRI-UHFFFAOYSA-N 0.000 claims 1
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| WO2016039938A1 (en) * | 2014-09-09 | 2016-03-17 | Ptc Therapeutics, Inc. | Polycyclic 2-pyridinone antibacterial compounds |
| WO2016109706A1 (en) * | 2014-12-31 | 2016-07-07 | Ptc Therapeutics, Inc. | Fused polycyclic 2-pyridinone antibacterial compounds |
| WO2018200571A1 (en) | 2017-04-25 | 2018-11-01 | Arbutus Biopharma Corporation | Substituted 2,3-dihydro-1h-indene analogs and methods using same |
| GB201720163D0 (en) * | 2017-12-04 | 2018-01-17 | Galapagos Nv | Novel compounds and pharmaceutical compositions thereof for the treatment of hepatitis B |
| TWI801517B (zh) * | 2018-03-12 | 2023-05-11 | 加拿大商愛彼特生物製藥公司 | 經取代的2-吡啶酮三環化合物、其類似物及其使用方法 |
| US12083118B2 (en) | 2018-03-29 | 2024-09-10 | Arbutus Biopharma Corporation | Substituted 1,1′-biphenyl compounds, analogues thereof, and methods using same |
| CN108659091B (zh) * | 2018-05-24 | 2020-07-03 | 烟台大学 | 夫西地酸衍生物及其合成制备方法和应用 |
| RU2711968C1 (ru) * | 2018-11-22 | 2020-01-24 | федеральное государственное бюджетное образовательное учреждение высшего образования "Пермский национальный исследовательский политехнический университет" | Анальгезирующее средство |
| KR20210145788A (ko) | 2019-04-01 | 2021-12-02 | 닛산 가가쿠 가부시키가이샤 | 피리다지논 화합물 및 제초제 |
| WO2021000297A1 (en) | 2019-07-03 | 2021-01-07 | Merck Sharp & Dohme Corp. | Compounds and methods of use thereof as antibacterial agents |
| CN112592343B (zh) * | 2019-10-01 | 2023-05-16 | 周雨恬 | 一种多环化合物及作为抗病毒药物的应用 |
| KR20230026479A (ko) | 2020-06-22 | 2023-02-24 | 에프. 호프만-라 로슈 아게 | 설폰 유도체 |
| MX2023010948A (es) * | 2021-03-17 | 2023-11-28 | Janssen Sciences Ireland Unlimited Co | Compuestos antibacterianos. |
| US11964986B1 (en) | 2023-07-03 | 2024-04-23 | Rejuveron Telomere Therapeutics Ag | 9-oxo-9,10-dihydro-6H-pyrano[3,2-b:4,5-b′]dipyridine-8-carboxylic acid derivatives |
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| US4474786A (en) * | 1983-06-16 | 1984-10-02 | Schering Corporation | Tricyclic lactams and derivatives useful in increasing cardiac contractility |
| JPS60197684A (ja) * | 1984-03-21 | 1985-10-07 | Dainippon Pharmaceut Co Ltd | ベンゾ〔ａ〕キノリジン誘導体およびその塩 |
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| WO2008127274A2 (en) * | 2006-09-22 | 2008-10-23 | Ptc Therapeutics, Inc. | Heterocyclic inhibitors of bacterial peptidyl trna hydrolase and uses thereof |
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