JP2016527321A5 - - Google Patents
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- Publication number
- JP2016527321A5 JP2016527321A5 JP2016533471A JP2016533471A JP2016527321A5 JP 2016527321 A5 JP2016527321 A5 JP 2016527321A5 JP 2016533471 A JP2016533471 A JP 2016533471A JP 2016533471 A JP2016533471 A JP 2016533471A JP 2016527321 A5 JP2016527321 A5 JP 2016527321A5
- Authority
- JP
- Japan
- Prior art keywords
- mycobacterium
- compound
- formula
- pharmaceutically acceptable
- borabenzo
- 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.)
- Granted
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- SEZUIFUXTYWPPI-UHFFFAOYSA-N (5-chloro-11-methyl-2,9,12-trioxa-1-boratricyclo[6.4.1.04,13]trideca-4,6,8(13)-trien-3-yl)methanamine Chemical compound CC1COC2=C3B(OC(CN)C3=C(Cl)C=C2)O1 SEZUIFUXTYWPPI-UHFFFAOYSA-N 0.000 claims description 2
- UCKURIYBZQDEIO-UHFFFAOYSA-N CC1(C)COC2=C3B(OC(CN)C3=C(Br)C=C2)O1 Chemical compound CC1(C)COC2=C3B(OC(CN)C3=C(Br)C=C2)O1 UCKURIYBZQDEIO-UHFFFAOYSA-N 0.000 claims description 2
- DNCNLMBTZDBNIS-UHFFFAOYSA-N CC1(C)COC2=C3B(OC(CN)C3=C(Cl)C=C2)O1 Chemical compound CC1(C)COC2=C3B(OC(CN)C3=C(Cl)C=C2)O1 DNCNLMBTZDBNIS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 23
- 150000003839 salts Chemical class 0.000 claims 23
- 241000186359 Mycobacterium Species 0.000 claims 19
- 229940124597 therapeutic agent Drugs 0.000 claims 13
- 201000008827 tuberculosis Diseases 0.000 claims 8
- 241001465754 Metazoa Species 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- -1 monocarbonate Chemical compound 0.000 claims 7
- 206010062207 Mycobacterial infection Diseases 0.000 claims 6
- 208000027531 mycobacterial infectious disease Diseases 0.000 claims 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 6
- 241000187479 Mycobacterium tuberculosis Species 0.000 claims 4
- AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 3
- 125000001246 bromo group Chemical group Br* 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 2
- 208000023081 Buruli ulcer disease Diseases 0.000 claims 2
- BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 208000019693 Lung disease Diseases 0.000 claims 2
- 241000186367 Mycobacterium avium Species 0.000 claims 2
- 241000186365 Mycobacterium fortuitum Species 0.000 claims 2
- 241000186363 Mycobacterium kansasii Species 0.000 claims 2
- GTPRAUYDOHITMN-MRVPVSSYSA-N [(3S)-5-bromo-2,9,12-trioxa-1-boratricyclo[6.4.1.04,13]trideca-4,6,8(13)-trien-3-yl]methanamine Chemical compound NC[C@H]1OB2OCCOc3ccc(Br)c1c23 GTPRAUYDOHITMN-MRVPVSSYSA-N 0.000 claims 2
- WOZSCQDILHKSGG-UHFFFAOYSA-N adefovir depivoxil Chemical compound N1=CN=C2N(CCOCP(=O)(OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C)C=NC2=C1N WOZSCQDILHKSGG-UHFFFAOYSA-N 0.000 claims 2
- 229940124522 antiretrovirals Drugs 0.000 claims 2
- 239000003903 antiretrovirus agent Substances 0.000 claims 2
- 229960005107 darunavir Drugs 0.000 claims 2
- CJBJHOAVZSMMDJ-HEXNFIEUSA-N darunavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)C1=CC=CC=C1 CJBJHOAVZSMMDJ-HEXNFIEUSA-N 0.000 claims 2
- 229960002656 didanosine Drugs 0.000 claims 2
- PEASPLKKXBYDKL-FXEVSJAOSA-N enfuvirtide Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(C)=O)[C@@H](C)O)[C@@H](C)CC)C1=CN=CN1 PEASPLKKXBYDKL-FXEVSJAOSA-N 0.000 claims 2
- 229960002049 etravirine Drugs 0.000 claims 2
- PYGWGZALEOIKDF-UHFFFAOYSA-N etravirine Chemical compound CC1=CC(C#N)=CC(C)=C1OC1=NC(NC=2C=CC(=CC=2)C#N)=NC(N)=C1Br PYGWGZALEOIKDF-UHFFFAOYSA-N 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000002346 iodo group Chemical group I* 0.000 claims 2
- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- UBHVTBVINWNDLN-UHFFFAOYSA-N (5-bromo-11-methyl-2,9,12-trioxa-1-boratricyclo[6.4.1.04,13]trideca-4,6,8(13)-trien-3-yl)methanamine Chemical compound CC1COC2=C3B(OC(CN)C3=C(Br)C=C2)O1 UBHVTBVINWNDLN-UHFFFAOYSA-N 0.000 claims 1
- GTPRAUYDOHITMN-UHFFFAOYSA-N (5-bromo-2,9,12-trioxa-1-boratricyclo[6.4.1.04,13]trideca-4,6,8(13)-trien-3-yl)methanamine Chemical compound NCC1OB2OCCOC3=C2C1=C(Br)C=C3 GTPRAUYDOHITMN-UHFFFAOYSA-N 0.000 claims 1
- RNOYDEJQJQUYRO-UHFFFAOYSA-N (5-chloro-2,9,12-trioxa-1-boratricyclo[6.4.1.04,13]trideca-4,6,8(13)-trien-3-yl)methanamine Chemical compound NCC1OB2OCCOC3=C2C1=C(Cl)C=C3 RNOYDEJQJQUYRO-UHFFFAOYSA-N 0.000 claims 1
- KSAAKIKKTQBNSN-UHFFFAOYSA-N (5-fluoro-2,9,12-trioxa-1-boratricyclo[6.4.1.04,13]trideca-4,6,8(13)-trien-3-yl)methanamine Chemical compound NCC1OB2OCCOc3ccc(F)c1c23 KSAAKIKKTQBNSN-UHFFFAOYSA-N 0.000 claims 1
- HBUJYEUPIIJJOS-PBHICJAKSA-N (5r)-3-[4-[1-[(2s)-2,3-dihydroxypropanoyl]-3,6-dihydro-2h-pyridin-4-yl]-3,5-difluorophenyl]-5-(1,2-oxazol-3-yloxymethyl)-1,3-oxazolidin-2-one Chemical compound C1N(C(=O)[C@@H](O)CO)CCC(C=2C(=CC(=CC=2F)N2C(O[C@@H](COC3=NOC=C3)C2)=O)F)=C1 HBUJYEUPIIJJOS-PBHICJAKSA-N 0.000 claims 1
- QRPZBKAMSFHVRW-UHFFFAOYSA-N 1-(4-benzoylpiperazin-1-yl)-2-[4-methoxy-7-(3-methyl-1,2,4-triazol-1-yl)-1h-pyrrolo[2,3-c]pyridin-3-yl]ethane-1,2-dione Chemical compound C1=2NC=C(C(=O)C(=O)N3CCN(CC3)C(=O)C=3C=CC=CC=3)C=2C(OC)=CN=C1N1C=NC(C)=N1 QRPZBKAMSFHVRW-UHFFFAOYSA-N 0.000 claims 1
- OKGPFTLYBPQBIX-CQSZACIVSA-N 1-[(2r)-4-benzoyl-2-methylpiperazin-1-yl]-2-(4-methoxy-1h-pyrrolo[2,3-b]pyridin-3-yl)ethane-1,2-dione Chemical compound C1=2C(OC)=CC=NC=2NC=C1C(=O)C(=O)N([C@@H](C1)C)CCN1C(=O)C1=CC=CC=C1 OKGPFTLYBPQBIX-CQSZACIVSA-N 0.000 claims 1
- KIMCGLHTSSZPNS-UHFFFAOYSA-N 2,3-dinitrobenzamide Chemical compound NC(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O KIMCGLHTSSZPNS-UHFFFAOYSA-N 0.000 claims 1
- MJNPHLBKHKJDEF-UHFFFAOYSA-N 2h-1$l^{4},2-benzothiazine 1-oxide Chemical compound C1=CC=C2S(=O)NC=CC2=C1 MJNPHLBKHKJDEF-UHFFFAOYSA-N 0.000 claims 1
- YVMGQODAKAHLHB-UHFFFAOYSA-N 3-nitroimidazo[4,5-e]oxazine Chemical compound O1N=C([N+](=O)[O-])C=C2N=CN=C21 YVMGQODAKAHLHB-UHFFFAOYSA-N 0.000 claims 1
- HSBKFSPNDWWPSL-VDTYLAMSSA-N 4-amino-5-fluoro-1-[(2s,5r)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1[C@@H]1C=C[C@H](CO)O1 HSBKFSPNDWWPSL-VDTYLAMSSA-N 0.000 claims 1
- CGBYTKOSZYQOPV-ASSBYYIWSA-N 5-chloro-3-[[3-[(e)-2-cyanoethenyl]-5-methylphenyl]-methoxyphosphoryl]-1h-indole-2-carboxamide Chemical compound C1([P@](=O)(C=2C3=CC(Cl)=CC=C3NC=2C(N)=O)OC)=CC(C)=CC(\C=C\C#N)=C1 CGBYTKOSZYQOPV-ASSBYYIWSA-N 0.000 claims 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- AXRYRYVKAWYZBR-UHFFFAOYSA-N Atazanavir Natural products C=1C=C(C=2N=CC=CC=2)C=CC=1CN(NC(=O)C(NC(=O)OC)C(C)(C)C)CC(O)C(NC(=O)C(NC(=O)OC)C(C)(C)C)CC1=CC=CC=C1 AXRYRYVKAWYZBR-UHFFFAOYSA-N 0.000 claims 1
- 108010019625 Atazanavir Sulfate Proteins 0.000 claims 1
- 241001260012 Bursa Species 0.000 claims 1
- 208000006448 Buruli Ulcer Diseases 0.000 claims 1
- 108010036239 CD4-IgG(2) Proteins 0.000 claims 1
- QAGYKUNXZHXKMR-UHFFFAOYSA-N CPD000469186 Natural products CC1=C(O)C=CC=C1C(=O)NC(C(O)CN1C(CC2CCCCC2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- XQSPYNMVSIKCOC-NTSWFWBYSA-N Emtricitabine Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1O[C@@H](CO)SC1 XQSPYNMVSIKCOC-NTSWFWBYSA-N 0.000 claims 1
- 108010032976 Enfuvirtide Proteins 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- 241000233866 Fungi Species 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- KJHKTHWMRKYKJE-SUGCFTRWSA-N Kaletra Chemical compound N1([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)COC=2C(=CC=CC=2C)C)CC=2C=CC=CC=2)CCCNC1=O KJHKTHWMRKYKJE-SUGCFTRWSA-N 0.000 claims 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims 1
- 206010024229 Leprosy Diseases 0.000 claims 1
- 208000032376 Lung infection Diseases 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 241001508003 Mycobacterium abscessus Species 0.000 claims 1
- 241001467553 Mycobacterium africanum Species 0.000 claims 1
- 241000186366 Mycobacterium bovis Species 0.000 claims 1
- 241001467552 Mycobacterium bovis BCG Species 0.000 claims 1
- 241001312372 Mycobacterium canettii Species 0.000 claims 1
- 241000211133 Mycobacterium caprae Species 0.000 claims 1
- 241000186364 Mycobacterium intracellulare Species 0.000 claims 1
- 241000187492 Mycobacterium marinum Species 0.000 claims 1
- 241000187919 Mycobacterium microti Species 0.000 claims 1
- 241000187489 Mycobacterium simiae Species 0.000 claims 1
- 241000187917 Mycobacterium ulcerans Species 0.000 claims 1
- 206010066289 Mycobacterium ulcerans infection Diseases 0.000 claims 1
- 241000187494 Mycobacterium xenopi Species 0.000 claims 1
- 201000002481 Myositis Diseases 0.000 claims 1
- SYNVNXVFFXGJBH-MRVPVSSYSA-N NC[C@H]1OB2OCCOc3ccc(I)c1c23 Chemical compound NC[C@H]1OB2OCCOc3ccc(I)c1c23 SYNVNXVFFXGJBH-MRVPVSSYSA-N 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims 1
- 206010035664 Pneumonia Diseases 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 claims 1
- 244000082988 Secale cereale Species 0.000 claims 1
- 206010062255 Soft tissue infection Diseases 0.000 claims 1
- XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 claims 1
- SUJUHGSWHZTSEU-UHFFFAOYSA-N Tipranavir Natural products C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C(F)(F)F)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 SUJUHGSWHZTSEU-UHFFFAOYSA-N 0.000 claims 1
- UCKURIYBZQDEIO-SECBINFHSA-N [(3S)-5-bromo-11,11-dimethyl-2,9,12-trioxa-1-boratricyclo[6.4.1.04,13]trideca-4,6,8(13)-trien-3-yl]methanamine Chemical compound CC1(C)COc2ccc(Br)c3[C@@H](CN)OB(O1)c23 UCKURIYBZQDEIO-SECBINFHSA-N 0.000 claims 1
- DNCNLMBTZDBNIS-SECBINFHSA-N [(3S)-5-chloro-11,11-dimethyl-2,9,12-trioxa-1-boratricyclo[6.4.1.04,13]trideca-4,6,8(13)-trien-3-yl]methanamine Chemical compound CC1(C)COC2=C3B(O[C@H](CN)C3=C(Cl)C=C2)O1 DNCNLMBTZDBNIS-SECBINFHSA-N 0.000 claims 1
- RNOYDEJQJQUYRO-MRVPVSSYSA-N [(3S)-5-chloro-2,9,12-trioxa-1-boratricyclo[6.4.1.04,13]trideca-4,6,8(13)-trien-3-yl]methanamine Chemical compound O1CCOC2=CC=C(Cl)C3=C2B1O[C@@H]3CN RNOYDEJQJQUYRO-MRVPVSSYSA-N 0.000 claims 1
- 229960004748 abacavir Drugs 0.000 claims 1
- MCGSCOLBFJQGHM-SCZZXKLOSA-N abacavir Chemical compound C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 claims 1
- 206010000269 abscess Diseases 0.000 claims 1
- 229960001997 adefovir Drugs 0.000 claims 1
- 229960003205 adefovir dipivoxil Drugs 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical class O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 claims 1
- 229940072056 alginate Drugs 0.000 claims 1
- 235000010443 alginic acid Nutrition 0.000 claims 1
- 229920000615 alginic acid Polymers 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 229960001830 amprenavir Drugs 0.000 claims 1
- YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 229960003277 atazanavir Drugs 0.000 claims 1
- AXRYRYVKAWYZBR-GASGPIRDSA-N atazanavir Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 AXRYRYVKAWYZBR-GASGPIRDSA-N 0.000 claims 1
- 229960000508 bedaquiline Drugs 0.000 claims 1
- QUIJNHUBAXPXFS-XLJNKUFUSA-N bedaquiline Chemical compound C1([C@H](C2=CC3=CC(Br)=CC=C3N=C2OC)[C@@](O)(CCN(C)C)C=2C3=CC=CC=C3C=CC=2)=CC=CC=C1 QUIJNHUBAXPXFS-XLJNKUFUSA-N 0.000 claims 1
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| KR101636431B1 (ko) | 2013-07-30 | 2016-07-05 | 동아에스티 주식회사 | 트리사이클릭 벤즈옥사보롤 화합물, 이의 제조방법 및 용도 |
| US20160251380A1 (en) | 2013-08-09 | 2016-09-01 | Glaxosmithkline Intellectual Property (No.2) Limited | Tricyclic benzoxaborole compounds and uses thereof |
| CN106459097A (zh) | 2014-07-01 | 2017-02-22 | 第三共株式会社 | 作为抗菌剂的三环苯并氧杂硼杂环戊烯类 |
| MA41495A (fr) * | 2015-02-12 | 2017-12-19 | Anacor Pharmaceuticals Inc | Composés benzoxaborole et leurs utilisations |
| PE20190119A1 (es) | 2016-05-12 | 2019-01-17 | Anacor Pharmaceuticals Inc | Esteres de oxaborol y sus usos |
| CN109387594B (zh) * | 2017-08-08 | 2021-01-19 | 武汉武药科技有限公司 | 一种分离和分析贝达喹啉光学异构体的方法 |
| ES2949908T3 (es) * | 2018-01-09 | 2023-10-03 | Halcyon Labs Private Ltd | Proceso para la preparación de Crisaborol y sus intermedios |
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| AU2011237681B2 (en) * | 2010-04-07 | 2015-01-22 | Glaxosmithkline Llc | Process for preparing benzoxaboroles |
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| US8530452B2 (en) * | 2011-12-22 | 2013-09-10 | Micurx Pharmaceuticals, Inc. | Tricyclic boron compounds for antimicrobial therapy |
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| MA41495A (fr) * | 2015-02-12 | 2017-12-19 | Anacor Pharmaceuticals Inc | Composés benzoxaborole et leurs utilisations |
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- 2014-08-08 RS RS20220108A patent/RS62887B1/sr unknown
- 2014-08-08 EA EA201690135A patent/EA032844B1/ru unknown
- 2014-08-08 LT LTEPPCT/US2014/050370T patent/LT3030519T/lt unknown
- 2014-08-08 SI SI201431939T patent/SI3030519T1/sl unknown
- 2014-08-08 PL PL14834292T patent/PL3030519T3/pl unknown
- 2014-08-08 CN CN201480049562.3A patent/CN105492388B/zh active Active
- 2014-08-08 CN CN201811396796.1A patent/CN110003253B/zh active Active
- 2014-08-08 SG SG11201600787PA patent/SG11201600787PA/en unknown
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- 2014-08-08 CA CA2919888A patent/CA2919888C/en active Active
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2016
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- 2016-02-03 PH PH12016500234A patent/PH12016500234B1/en unknown
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- 2016-02-08 CL CL2016000313A patent/CL2016000313A1/es unknown
- 2016-02-09 DO DO2016000045A patent/DOP2016000045A/es unknown
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2017
- 2017-08-03 AU AU2017210567A patent/AU2017210567B2/en active Active
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2019
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2020
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2022
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