KR20080110984A - 보론함유 소분자 - Google Patents
보론함유 소분자 Download PDFInfo
- Publication number
- KR20080110984A KR20080110984A KR1020087018808A KR20087018808A KR20080110984A KR 20080110984 A KR20080110984 A KR 20080110984A KR 1020087018808 A KR1020087018808 A KR 1020087018808A KR 20087018808 A KR20087018808 A KR 20087018808A KR 20080110984 A KR20080110984 A KR 20080110984A
- Authority
- KR
- South Korea
- Prior art keywords
- substituted
- unsubstituted
- compound
- member selected
- alkyl
- 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.)
- Withdrawn
Links
- 229910052796 boron Inorganic materials 0.000 title claims description 42
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims description 30
- 150000003384 small molecules Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 485
- 210000000282 nail Anatomy 0.000 claims abstract description 123
- 241000233866 Fungi Species 0.000 claims abstract description 44
- 210000000003 hoof Anatomy 0.000 claims abstract description 28
- 208000031888 Mycoses Diseases 0.000 claims abstract description 15
- 206010017533 Fungal infection Diseases 0.000 claims abstract description 13
- 208000010195 Onychomycosis Diseases 0.000 claims abstract description 8
- 201000005882 tinea unguium Diseases 0.000 claims abstract description 8
- 210000000078 claw Anatomy 0.000 claims abstract description 6
- -1 methoxymethoxy Chemical group 0.000 claims description 883
- 238000000034 method Methods 0.000 claims description 232
- 125000000217 alkyl group Chemical group 0.000 claims description 177
- 108020004566 Transfer RNA Proteins 0.000 claims description 139
- 102000052866 Amino Acyl-tRNA Synthetases Human genes 0.000 claims description 121
- 108700028939 Amino Acyl-tRNA Synthetases Proteins 0.000 claims description 121
- 125000003118 aryl group Chemical group 0.000 claims description 116
- 125000001072 heteroaryl group Chemical group 0.000 claims description 107
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 104
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 99
- 125000004429 atom Chemical group 0.000 claims description 97
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 94
- 241000894007 species Species 0.000 claims description 87
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 86
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 80
- 244000005700 microbiome Species 0.000 claims description 75
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 69
- 229910052736 halogen Inorganic materials 0.000 claims description 67
- 150000002367 halogens Chemical class 0.000 claims description 64
- 239000002904 solvent Substances 0.000 claims description 64
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 53
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 51
- 238000006243 chemical reaction Methods 0.000 claims description 50
- 241000282414 Homo sapiens Species 0.000 claims description 47
- 150000001413 amino acids Chemical class 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 46
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 42
- 150000002148 esters Chemical class 0.000 claims description 42
- 208000015181 infectious disease Diseases 0.000 claims description 35
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 33
- 239000003814 drug Substances 0.000 claims description 32
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 32
- 238000009472 formulation Methods 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 30
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims description 30
- 241001465754 Metazoa Species 0.000 claims description 28
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 241000894006 Bacteria Species 0.000 claims description 26
- 210000004209 hair Anatomy 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 108010076876 Keratins Proteins 0.000 claims description 24
- 102000011782 Keratins Human genes 0.000 claims description 24
- 125000005842 heteroatom Chemical group 0.000 claims description 24
- 230000002401 inhibitory effect Effects 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 230000015572 biosynthetic process Effects 0.000 claims description 22
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
- 230000000694 effects Effects 0.000 claims description 22
- 230000004048 modification Effects 0.000 claims description 22
- 238000012986 modification Methods 0.000 claims description 22
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
- 238000003786 synthesis reaction Methods 0.000 claims description 22
- 125000004122 cyclic group Chemical group 0.000 claims description 21
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 20
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 20
- 125000001041 indolyl group Chemical group 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
- 125000001153 fluoro group Chemical group F* 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 18
- 230000012010 growth Effects 0.000 claims description 17
- 230000005764 inhibitory process Effects 0.000 claims description 17
- 238000001953 recrystallisation Methods 0.000 claims description 17
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 17
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 16
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 15
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 15
- 241001480043 Arthrodermataceae Species 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 230000037304 dermatophytes Effects 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 15
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 15
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 15
- 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 15
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 15
- 125000002757 morpholinyl group Chemical group 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 244000045947 parasite Species 0.000 claims description 15
- LFQDNHWZDQTITF-UHFFFAOYSA-N tavaborole Chemical compound FC1=CC=C2B(O)OCC2=C1 LFQDNHWZDQTITF-UHFFFAOYSA-N 0.000 claims description 15
- 241000223238 Trichophyton Species 0.000 claims description 14
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 14
- 239000002773 nucleotide Substances 0.000 claims description 14
- 125000003729 nucleotide group Chemical group 0.000 claims description 14
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 14
- 238000012360 testing method Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 102000004190 Enzymes Human genes 0.000 claims description 13
- 108090000790 Enzymes Proteins 0.000 claims description 13
- 241000223229 Trichophyton rubrum Species 0.000 claims description 13
- 125000003282 alkyl amino group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 230000000813 microbial effect Effects 0.000 claims description 13
- MLRBNIXMTWSDJU-UHFFFAOYSA-N 2-benzylfuran Chemical class C=1C=CC=CC=1CC1=CC=CO1 MLRBNIXMTWSDJU-UHFFFAOYSA-N 0.000 claims description 12
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 12
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 12
- 150000007523 nucleic acids Chemical class 0.000 claims description 12
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- 102000003960 Ligases Human genes 0.000 claims description 10
- 108090000364 Ligases Proteins 0.000 claims description 10
- 108091028043 Nucleic acid sequence Proteins 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 230000004071 biological effect Effects 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 210000004904 fingernail bed Anatomy 0.000 claims description 10
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 10
- 150000003212 purines Chemical class 0.000 claims description 10
- 150000003222 pyridines Chemical class 0.000 claims description 10
- 150000003230 pyrimidines Chemical class 0.000 claims description 10
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
- 241000222122 Candida albicans Species 0.000 claims description 9
- 241001480035 Epidermophyton Species 0.000 claims description 9
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 claims description 9
- 150000002460 imidazoles Chemical class 0.000 claims description 9
- 230000002147 killing effect Effects 0.000 claims description 9
- 125000003386 piperidinyl group Chemical group 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- 241001480037 Microsporum Species 0.000 claims description 8
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 8
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine group Chemical group [C@@H]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C=NC=2C(N)=NC=NC12 OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 8
- 125000001246 bromo group Chemical group Br* 0.000 claims description 8
- 229940095731 candida albicans Drugs 0.000 claims description 8
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical class CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 8
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims description 7
- 208000002474 Tinea Diseases 0.000 claims description 7
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 7
- 230000001086 cytosolic effect Effects 0.000 claims description 7
- 125000004288 oxazolidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC1([H])* 0.000 claims description 7
- 125000005864 sulfonamidyl group Chemical group 0.000 claims description 7
- 229930024421 Adenine Natural products 0.000 claims description 6
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical class NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 6
- 241000228212 Aspergillus Species 0.000 claims description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 6
- 229960000643 adenine Drugs 0.000 claims description 6
- 230000001580 bacterial effect Effects 0.000 claims description 6
- 230000002438 mitochondrial effect Effects 0.000 claims description 6
- 230000009885 systemic effect Effects 0.000 claims description 6
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims description 5
- 241000228245 Aspergillus niger Species 0.000 claims description 5
- 241000588724 Escherichia coli Species 0.000 claims description 5
- 241000223218 Fusarium Species 0.000 claims description 5
- 238000010521 absorption reaction Methods 0.000 claims description 5
- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical group C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 claims description 5
- 125000003275 alpha amino acid group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 208000017520 skin disease Diseases 0.000 claims description 5
- DHANQIJKGVELAS-UHFFFAOYSA-N 3-phenyldioxaborolane Chemical class O1OCCB1C1=CC=CC=C1 DHANQIJKGVELAS-UHFFFAOYSA-N 0.000 claims description 4
- 241000223602 Alternaria alternata Species 0.000 claims description 4
- 241000223678 Aureobasidium pullulans Species 0.000 claims description 4
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 4
- FRDOMQZQFJXSJN-UHFFFAOYSA-N CC1(C)BOOC1(C)C Chemical class CC1(C)BOOC1(C)C FRDOMQZQFJXSJN-UHFFFAOYSA-N 0.000 claims description 4
- 201000004624 Dermatitis Diseases 0.000 claims description 4
- 238000003747 Grignard reaction Methods 0.000 claims description 4
- 241000228143 Penicillium Species 0.000 claims description 4
- 241000371621 Stemphylium Species 0.000 claims description 4
- 230000001154 acute effect Effects 0.000 claims description 4
- 229960005305 adenosine Drugs 0.000 claims description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 108020004707 nucleic acids Proteins 0.000 claims description 4
- 102000039446 nucleic acids Human genes 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000010791 quenching Methods 0.000 claims description 4
- 230000000171 quenching effect Effects 0.000 claims description 4
- 229910052709 silver Inorganic materials 0.000 claims description 4
- 239000004332 silver Substances 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 229940113082 thymine Drugs 0.000 claims description 4
- 229940035893 uracil Drugs 0.000 claims description 4
- UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 claims description 3
- 201000004384 Alopecia Diseases 0.000 claims description 3
- 206010003694 Atrophy Diseases 0.000 claims description 3
- 241001337994 Cryptococcus <scale insect> Species 0.000 claims description 3
- UHDGCWIWMRVCDJ-PSQAKQOGSA-N Cytidine Natural products O=C1N=C(N)C=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-PSQAKQOGSA-N 0.000 claims description 3
- 206010048768 Dermatosis Diseases 0.000 claims description 3
- 206010018612 Gonorrhoea Diseases 0.000 claims description 3
- 208000007514 Herpes zoster Diseases 0.000 claims description 3
- 206010061304 Nail infection Diseases 0.000 claims description 3
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 3
- 241000122799 Scopulariopsis Species 0.000 claims description 3
- 231100000360 alopecia Toxicity 0.000 claims description 3
- 230000037444 atrophy Effects 0.000 claims description 3
- 230000001684 chronic effect Effects 0.000 claims description 3
- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical class O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 claims description 3
- 208000001786 gonorrhea Diseases 0.000 claims description 3
- 230000002757 inflammatory effect Effects 0.000 claims description 3
- 125000002346 iodo group Chemical group I* 0.000 claims description 3
- 239000003550 marker Substances 0.000 claims description 3
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 claims description 3
- 241000335423 Blastomyces Species 0.000 claims description 2
- 241001149956 Cladosporium herbarum Species 0.000 claims description 2
- 208000032541 Epidermal naevus Diseases 0.000 claims description 2
- 241000228402 Histoplasma Species 0.000 claims description 2
- 206010024229 Leprosy Diseases 0.000 claims description 2
- 241000555676 Malassezia Species 0.000 claims description 2
- 241000721454 Pemphigus Species 0.000 claims description 2
- 239000001177 diphosphate Substances 0.000 claims description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical class [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 2
- 235000011180 diphosphates Nutrition 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 150000004712 monophosphates Chemical class 0.000 claims description 2
- 230000002829 reductive effect Effects 0.000 claims description 2
- 238000004611 spectroscopical analysis Methods 0.000 claims description 2
- 208000006379 syphilis Diseases 0.000 claims description 2
- 201000008827 tuberculosis Diseases 0.000 claims description 2
- 239000008177 pharmaceutical agent Substances 0.000 claims 8
- 241000893966 Trichophyton verrucosum Species 0.000 claims 5
- 150000001722 carbon compounds Chemical class 0.000 claims 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims 5
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 5
- 102000004587 Methionine-tRNA ligase Human genes 0.000 claims 4
- 108010003060 Methionine-tRNA ligase Proteins 0.000 claims 4
- 125000001589 carboacyl group Chemical group 0.000 claims 4
- 230000000149 penetrating effect Effects 0.000 claims 4
- 102000029793 Isoleucine-tRNA ligase Human genes 0.000 claims 3
- 101710176147 Isoleucine-tRNA ligase, cytoplasmic Proteins 0.000 claims 3
- 102000017737 Lysine-tRNA Ligase Human genes 0.000 claims 3
- 108010092041 Lysine-tRNA Ligase Proteins 0.000 claims 3
- 102000002798 Phenylalanine-tRNA Ligase Human genes 0.000 claims 3
- 108010004478 Phenylalanine-tRNA Ligase Proteins 0.000 claims 3
- 101710149031 Probable isoleucine-tRNA ligase, cytoplasmic Proteins 0.000 claims 3
- 108010029287 Threonine-tRNA ligase Proteins 0.000 claims 3
- 102100040537 Threonine-tRNA ligase 1, cytoplasmic Human genes 0.000 claims 3
- 125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 102000004163 DNA-directed RNA polymerases Human genes 0.000 claims 2
- 108090000626 DNA-directed RNA polymerases Proteins 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- 125000000741 isoleucyl group Chemical group [H]N([H])C(C(C([H])([H])[H])C([H])([H])C([H])([H])[H])C(=O)O* 0.000 claims 2
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 206010029864 nystagmus Diseases 0.000 claims 2
- 244000052769 pathogen Species 0.000 claims 2
- 230000001717 pathogenic effect Effects 0.000 claims 2
- 125000000405 phenylalanyl group Chemical group 0.000 claims 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 1
- XMBPPRJTXLMQND-UHFFFAOYSA-N 3-methyldioxaborolane Chemical compound CB1CCOO1 XMBPPRJTXLMQND-UHFFFAOYSA-N 0.000 claims 1
- 229940126062 Compound A Drugs 0.000 claims 1
- 206010012442 Dermatitis contact Diseases 0.000 claims 1
- 206010015150 Erythema Diseases 0.000 claims 1
- OUHGTOMCWYHIPN-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)[IH]Br Chemical compound FC(F)(F)S(=O)(=O)[IH]Br OUHGTOMCWYHIPN-UHFFFAOYSA-N 0.000 claims 1
- 208000014260 Fungal keratitis Diseases 0.000 claims 1
- 244000037922 Gaultheria shallon Species 0.000 claims 1
- 235000004434 Gaultheria shallon Nutrition 0.000 claims 1
- 206010018691 Granuloma Diseases 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- 206010068058 Nail atrophy Diseases 0.000 claims 1
- 206010034464 Periarthritis Diseases 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 241000220317 Rosa Species 0.000 claims 1
- 201000009594 Systemic Scleroderma Diseases 0.000 claims 1
- 206010042953 Systemic sclerosis Diseases 0.000 claims 1
- 241000209140 Triticum Species 0.000 claims 1
- 235000021307 Triticum Nutrition 0.000 claims 1
- 208000004631 alopecia areata Diseases 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 claims 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
- 208000010247 contact dermatitis Diseases 0.000 claims 1
- IRDWNJAVINUANK-UHFFFAOYSA-N dioxaborinine Chemical class O1OC=CC=B1 IRDWNJAVINUANK-UHFFFAOYSA-N 0.000 claims 1
- 231100000321 erythema Toxicity 0.000 claims 1
- 208000024386 fungal infectious disease Diseases 0.000 claims 1
- 210000001654 germ layer Anatomy 0.000 claims 1
- 208000003906 hydrocephalus Diseases 0.000 claims 1
- 206010020718 hyperplasia Diseases 0.000 claims 1
- 229910052738 indium Inorganic materials 0.000 claims 1
- 206010023365 keratopathy Diseases 0.000 claims 1
- 230000001418 larval effect Effects 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 210000005075 mammary gland Anatomy 0.000 claims 1
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 claims 1
- 210000003097 mucus Anatomy 0.000 claims 1
- 201000000050 myeloid neoplasm Diseases 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 239000011148 porous material Substances 0.000 claims 1
- 230000001124 posttranscriptional effect Effects 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 239000004576 sand Substances 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 206010043778 thyroiditis Diseases 0.000 claims 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 210000003491 skin Anatomy 0.000 abstract description 31
- 210000004906 toe nail Anatomy 0.000 abstract description 27
- 238000011282 treatment Methods 0.000 abstract description 27
- 230000000699 topical effect Effects 0.000 abstract description 16
- 230000035515 penetration Effects 0.000 abstract description 7
- 125000001424 substituent group Chemical group 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- 229940024606 amino acid Drugs 0.000 description 36
- 235000001014 amino acid Nutrition 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 26
- 210000004027 cell Anatomy 0.000 description 25
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 22
- 241000700605 Viruses Species 0.000 description 22
- 229940079593 drug Drugs 0.000 description 22
- 235000019441 ethanol Nutrition 0.000 description 20
- 230000035772 mutation Effects 0.000 description 19
- 229940121375 antifungal agent Drugs 0.000 description 18
- 238000003556 assay Methods 0.000 description 18
- 238000009835 boiling Methods 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 15
- 239000000539 dimer Substances 0.000 description 14
- 239000013638 trimer Substances 0.000 description 13
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 12
- 102000043856 Leucine-tRNA ligase Human genes 0.000 description 12
- 108010071170 Leucine-tRNA ligase Proteins 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 125000002015 acyclic group Chemical group 0.000 description 12
- 229940088598 enzyme Drugs 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 11
- 150000002500 ions Chemical class 0.000 description 11
- 229960000310 isoleucine Drugs 0.000 description 11
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 11
- 108090000623 proteins and genes Proteins 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 150000008064 anhydrides Chemical class 0.000 description 10
- 239000003112 inhibitor Substances 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- 241000193830 Bacillus <bacterium> Species 0.000 description 9
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 9
- 125000002252 acyl group Chemical group 0.000 description 9
- 230000000843 anti-fungal effect Effects 0.000 description 9
- 239000003429 antifungal agent Substances 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
- 239000004474 valine Substances 0.000 description 9
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 8
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 8
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 8
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 8
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 8
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 8
- 239000004472 Lysine Substances 0.000 description 8
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 8
- 229950006790 adenosine phosphate Drugs 0.000 description 8
- 229960003767 alanine Drugs 0.000 description 8
- 125000003368 amide group Chemical group 0.000 description 8
- 230000010261 cell growth Effects 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 238000009792 diffusion process Methods 0.000 description 8
- 229960003646 lysine Drugs 0.000 description 8
- 229930182817 methionine Natural products 0.000 description 8
- 108090000765 processed proteins & peptides Proteins 0.000 description 8
- 125000006239 protecting group Chemical group 0.000 description 8
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 7
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 7
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
- 241000187747 Streptomyces Species 0.000 description 7
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 7
- 239000004473 Threonine Substances 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
- 235000004279 alanine Nutrition 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 102000004196 processed proteins & peptides Human genes 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000283690 Bos taurus Species 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical group OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 6
- 241000186359 Mycobacterium Species 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 230000001965 increasing effect Effects 0.000 description 6
- 150000002540 isothiocyanates Chemical class 0.000 description 6
- 150000002632 lipids Chemical class 0.000 description 6
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 6
- 229920001184 polypeptide Polymers 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 210000001519 tissue Anatomy 0.000 description 6
- 241000589876 Campylobacter Species 0.000 description 5
- UDMBCSSLTHHNCD-UHFFFAOYSA-N Coenzym Q(11) Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(O)=O)C(O)C1O UDMBCSSLTHHNCD-UHFFFAOYSA-N 0.000 description 5
- 241000186216 Corynebacterium Species 0.000 description 5
- 108020004414 DNA Proteins 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 241000427940 Fusarium solani Species 0.000 description 5
- 150000001298 alcohols Chemical group 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 125000004474 heteroalkylene group Chemical group 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- 231100000252 nontoxic Toxicity 0.000 description 5
- 230000003000 nontoxic effect Effects 0.000 description 5
- OHENQANLQNOMAO-UHFFFAOYSA-N oxaborole Chemical compound O1B=CC=C1 OHENQANLQNOMAO-UHFFFAOYSA-N 0.000 description 5
- 230000035699 permeability Effects 0.000 description 5
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 5
- 210000000434 stratum corneum Anatomy 0.000 description 5
- 125000003107 substituted aryl group Chemical group 0.000 description 5
- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 description 5
- 229960002722 terbinafine Drugs 0.000 description 5
- 238000011200 topical administration Methods 0.000 description 5
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- OIVLITBTBDPEFK-UHFFFAOYSA-N 5,6-dihydrouracil Chemical class O=C1CCNC(=O)N1 OIVLITBTBDPEFK-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 241000589158 Agrobacterium Species 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 241000588807 Bordetella Species 0.000 description 4
- 241000193403 Clostridium Species 0.000 description 4
- 241000711573 Coronaviridae Species 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000588914 Enterobacter Species 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 241000606790 Haemophilus Species 0.000 description 4
- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 4
- 241000701074 Human alphaherpesvirus 2 Species 0.000 description 4
- 241000701024 Human betaherpesvirus 5 Species 0.000 description 4
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 4
- 241000713340 Human immunodeficiency virus 2 Species 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
- 241000606860 Pasteurella Species 0.000 description 4
- 241001193612 Phoma violacea Species 0.000 description 4
- 108010039918 Polylysine Proteins 0.000 description 4
- 241000589516 Pseudomonas Species 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 241000607142 Salmonella Species 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 241000607598 Vibrio Species 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 244000309464 bull Species 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical class NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 4
- 230000001976 improved effect Effects 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 238000002483 medication Methods 0.000 description 4
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 208000026721 nail disease Diseases 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000002777 nucleoside Substances 0.000 description 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920000656 polylysine Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000651 prodrug Substances 0.000 description 4
- 229940002612 prodrug Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000000241 respiratory effect Effects 0.000 description 4
- 229910052703 rhodium Inorganic materials 0.000 description 4
- 239000010948 rhodium Substances 0.000 description 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 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 description 4
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 3
- JOXJSNMBKNEDTQ-UHFFFAOYSA-N 2-(3-chlorophenyl)-1,3,2-dioxaborolane Chemical compound ClC1=CC=CC(B2OCCO2)=C1 JOXJSNMBKNEDTQ-UHFFFAOYSA-N 0.000 description 3
- VHVPQPYKVGDNFY-DFMJLFEVSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-DFMJLFEVSA-N 0.000 description 3
- GDUXKUYAOLDWIU-UHFFFAOYSA-N 3-(1,3,2-dioxaborolan-2-yl)benzonitrile Chemical compound N#CC1=CC=CC(B2OCCO2)=C1 GDUXKUYAOLDWIU-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- 241000283707 Capra Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- 241000710781 Flaviviridae Species 0.000 description 3
- 241000287828 Gallus gallus Species 0.000 description 3
- 241000711549 Hepacivirus C Species 0.000 description 3
- 241000701044 Human gammaherpesvirus 4 Species 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 241000555688 Malassezia furfur Species 0.000 description 3
- 206010026749 Mania Diseases 0.000 description 3
- 241000893976 Nannizzia gypsea Species 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 241001494479 Pecora Species 0.000 description 3
- 241000235645 Pichia kudriavzevii Species 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 241000186429 Propionibacterium Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 101100205184 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CDC60 gene Proteins 0.000 description 3
- 241000607768 Shigella Species 0.000 description 3
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 3
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 3
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 235000013330 chicken meat Nutrition 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940088679 drug related substance Drugs 0.000 description 3
- RFHAOTPXVQNOHP-UHFFFAOYSA-N fluconazole Chemical compound C1=NC=NN1CC(C=1C(=CC(F)=CC=1)F)(O)CN1C=NC=N1 RFHAOTPXVQNOHP-UHFFFAOYSA-N 0.000 description 3
- 229960004884 fluconazole Drugs 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
- 150000004677 hydrates Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000003834 intracellular effect Effects 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 229960004130 itraconazole Drugs 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 108020004999 messenger RNA Proteins 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000001979 organolithium group Chemical group 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 238000001356 surgical procedure Methods 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- 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 description 2
- UZKBSZSTDQSMDR-UHFFFAOYSA-N 1-[(4-chlorophenyl)-phenylmethyl]piperazine Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 UZKBSZSTDQSMDR-UHFFFAOYSA-N 0.000 description 2
- LPHIYKWSEYTCLW-UHFFFAOYSA-N 1h-azaborole Chemical compound N1B=CC=C1 LPHIYKWSEYTCLW-UHFFFAOYSA-N 0.000 description 2
- ZZTKQFUKXNRAKR-UHFFFAOYSA-N 2-[3-(3h-2,1-benzoxaborol-1-yl)phenoxy]-5-chlorophenol Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=CC(B2C3=CC=CC=C3CO2)=C1 ZZTKQFUKXNRAKR-UHFFFAOYSA-N 0.000 description 2
- BUDOHXRLVIXTME-UHFFFAOYSA-N 3,4-dimethyldioxaborinane Chemical compound CB1OOCCC1C BUDOHXRLVIXTME-UHFFFAOYSA-N 0.000 description 2
- VHDDPRSTDANHBU-UHFFFAOYSA-N 4-(1,3,2-dioxaborolan-2-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1B1OCCO1 VHDDPRSTDANHBU-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- ZLOIGESWDJYCTF-UHFFFAOYSA-N 4-Thiouridine Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=S)C=C1 ZLOIGESWDJYCTF-UHFFFAOYSA-N 0.000 description 2
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 description 2
- PXACTUVBBMDKRW-UHFFFAOYSA-M 4-bromobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-M 0.000 description 2
- ZLOIGESWDJYCTF-XVFCMESISA-N 4-thiouridine Chemical class O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=S)C=C1 ZLOIGESWDJYCTF-XVFCMESISA-N 0.000 description 2
- 241000186046 Actinomyces Species 0.000 description 2
- 241000272525 Anas platyrhynchos Species 0.000 description 2
- 241000272814 Anser sp. Species 0.000 description 2
- 241000256844 Apis mellifera Species 0.000 description 2
- 241000203069 Archaea Species 0.000 description 2
- 241001225321 Aspergillus fumigatus Species 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 2
- 241001416153 Bos grunniens Species 0.000 description 2
- 241000589562 Brucella Species 0.000 description 2
- 241000282836 Camelus dromedarius Species 0.000 description 2
- 241000222173 Candida parapsilosis Species 0.000 description 2
- 241000222178 Candida tropicalis Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- 241000282994 Cervidae Species 0.000 description 2
- 241000606161 Chlamydia Species 0.000 description 2
- 241000606153 Chlamydia trachomatis Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000222290 Cladosporium Species 0.000 description 2
- 241000272201 Columbiformes Species 0.000 description 2
- 201000003075 Crimean-Congo hemorrhagic fever Diseases 0.000 description 2
- 241000221204 Cryptococcus neoformans Species 0.000 description 2
- 206010012504 Dermatophytosis Diseases 0.000 description 2
- 241000194033 Enterococcus Species 0.000 description 2
- 241001480036 Epidermophyton floccosum Species 0.000 description 2
- 241000283086 Equidae Species 0.000 description 2
- 241000283073 Equus caballus Species 0.000 description 2
- 241000588722 Escherichia Species 0.000 description 2
- 241000192125 Firmicutes Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 241000589989 Helicobacter Species 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 241000701027 Human herpesvirus 6 Species 0.000 description 2
- 229930010555 Inosine Natural products 0.000 description 2
- UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical class O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 description 2
- 241000588748 Klebsiella Species 0.000 description 2
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 2
- 241000222724 Leishmania amazonensis Species 0.000 description 2
- 244000207740 Lemna minor Species 0.000 description 2
- 241001233242 Lontra Species 0.000 description 2
- 241000406668 Loxodonta cyclotis Species 0.000 description 2
- 241001299738 Malassezia pachydermatis Species 0.000 description 2
- 241001291478 Malassezia sympodialis Species 0.000 description 2
- 241001480000 Microsporum audouinii Species 0.000 description 2
- 241000893980 Microsporum canis Species 0.000 description 2
- 241001460074 Microsporum distortum Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 2
- 241000272458 Numididae Species 0.000 description 2
- 108091034117 Oligonucleotide Proteins 0.000 description 2
- 241000711504 Paramyxoviridae Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000283011 Rangifer Species 0.000 description 2
- 241000235527 Rhizopus Species 0.000 description 2
- 241000282849 Ruminantia Species 0.000 description 2
- 241000825258 Scopulariopsis brevicaulis Species 0.000 description 2
- 241000589973 Spirochaeta Species 0.000 description 2
- 241000191940 Staphylococcus Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 2
- 241000194017 Streptococcus Species 0.000 description 2
- 241000272534 Struthio camelus Species 0.000 description 2
- 241000282898 Sus scrofa Species 0.000 description 2
- 241000606507 Talaromyces pinophilus Species 0.000 description 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 241000088074 Turbinella pyrum Species 0.000 description 2
- 241000607626 Vibrio cholerae Species 0.000 description 2
- 241000607734 Yersinia <bacteria> Species 0.000 description 2
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical group N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 2
- HMAKMGIOLLFHOF-UHFFFAOYSA-N [2-(3h-2,1-benzoxaborol-1-yl)-5-chlorophenyl]methanol Chemical compound OCC1=CC(Cl)=CC=C1B1C2=CC=CC=C2CO1 HMAKMGIOLLFHOF-UHFFFAOYSA-N 0.000 description 2
- RJOAWYWGRKWCPB-UHFFFAOYSA-N [2-(3h-2,1-benzoxaborol-1-yl)phenyl]methanol Chemical compound OCC1=CC=CC=C1B1C2=CC=CC=C2CO1 RJOAWYWGRKWCPB-UHFFFAOYSA-N 0.000 description 2
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 2
- 241000222126 [Candida] glabrata Species 0.000 description 2
- 230000003187 abdominal effect Effects 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 230000006229 amino acid addition Effects 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 125000005002 aryl methyl group Chemical group 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 150000001639 boron compounds Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 208000032343 candida glabrata infection Diseases 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 229940038705 chlamydia trachomatis Drugs 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 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 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 2
- 235000018417 cysteine Nutrition 0.000 description 2
- 229940104302 cytosine Drugs 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 206010013023 diphtheria Diseases 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 229940096118 ella Drugs 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000000833 heterodimer Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229960003786 inosine Drugs 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 2
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 2
- 239000012907 medicinal substance Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 229960003512 nicotinic acid Drugs 0.000 description 2
- 235000001968 nicotinic acid Nutrition 0.000 description 2
- 239000011664 nicotinic acid Substances 0.000 description 2
- 150000003833 nucleoside derivatives Chemical class 0.000 description 2
- 125000003835 nucleoside group Chemical group 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000013612 plasmid Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 230000001915 proofreading effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 201000005404 rubella Diseases 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- 229960005322 streptomycin Drugs 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 125000002130 sulfonic acid ester group Chemical group 0.000 description 2
- 150000003459 sulfonic acid esters Chemical class 0.000 description 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000005309 thioalkoxy group Chemical group 0.000 description 2
- 239000012049 topical pharmaceutical composition Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000013518 transcription Methods 0.000 description 2
- 230000035897 transcription Effects 0.000 description 2
- 230000037317 transdermal delivery Effects 0.000 description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 description 2
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 2
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 2
- 125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 2
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 2
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
- 238000007514 turning Methods 0.000 description 2
- OOLLAFOLCSJHRE-ZHAKMVSLSA-N ulipristal acetate Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(OC(C)=O)C(C)=O)[C@]2(C)C1 OOLLAFOLCSJHRE-ZHAKMVSLSA-N 0.000 description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 1
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- 102000040650 (ribonucleotides)n+m Human genes 0.000 description 1
- 125000000196 1,4-pentadienyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])=C([H])[H] 0.000 description 1
- FNXHOBDXERDGGW-UHFFFAOYSA-N 1-(3-chlorophenyl)-3h-2,1-benzoxaborole Chemical compound ClC1=CC=CC(B2C3=CC=CC=C3CO2)=C1 FNXHOBDXERDGGW-UHFFFAOYSA-N 0.000 description 1
- GMPASXURYDBGPI-UHFFFAOYSA-N 1-(3-chlorophenyl)-4,5-dihydro-3h-2,1-benzoxaborepine Chemical compound ClC1=CC=CC(B2C3=CC=CC=C3CCCO2)=C1 GMPASXURYDBGPI-UHFFFAOYSA-N 0.000 description 1
- YQAAYZFWEHIEBZ-UHFFFAOYSA-N 1-(4-chloro-2-methoxyphenyl)-2,3-dihydro-1h-benzo[c][1,2]benzoxaborole Chemical compound COC1=CC(Cl)=CC=C1C1C23C=CC=CC2=BOC3=CCC1 YQAAYZFWEHIEBZ-UHFFFAOYSA-N 0.000 description 1
- ZPBBUGVRRBPAGW-UHFFFAOYSA-N 1-[2-(3h-2,1-benzoxaborol-1-yl)-5-chlorophenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC(Cl)=CC=C1B1C2=CC=CC=C2CO1 ZPBBUGVRRBPAGW-UHFFFAOYSA-N 0.000 description 1
- IHUIFUYFNXHXKM-UHFFFAOYSA-N 1-[2-(3h-2,1-benzoxaborol-1-yl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1B1C2=CC=CC=C2CO1 IHUIFUYFNXHXKM-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- YFTHTJAPODJVSL-UHFFFAOYSA-N 2-(1-benzothiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(SC=C2)C2=C1 YFTHTJAPODJVSL-UHFFFAOYSA-N 0.000 description 1
- AMROMNCFBJPUEB-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3,2-dioxaborolane Chemical compound FC1=CC=CC(B2OCCO2)=C1 AMROMNCFBJPUEB-UHFFFAOYSA-N 0.000 description 1
- ZDANMRXRFANFKM-UHFFFAOYSA-N 2-(4-chlorophenyl)-1,3,2-dioxaborolane Chemical compound C1=CC(Cl)=CC=C1B1OCCO1 ZDANMRXRFANFKM-UHFFFAOYSA-N 0.000 description 1
- RTVDRQDLRDTRGP-UHFFFAOYSA-N 2-[2-(methoxymethoxymethyl)phenyl]-1,3,2-dioxaborolane Chemical compound COCOCC1=CC=CC=C1B1OCCO1 RTVDRQDLRDTRGP-UHFFFAOYSA-N 0.000 description 1
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 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 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- LWEYICDKBBAZLK-UHFFFAOYSA-N 3-(5,6-dimethoxy-3h-2,1-benzoxaborol-1-yl)benzonitrile Chemical compound C1=2C=C(OC)C(OC)=CC=2COB1C1=CC=CC(C#N)=C1 LWEYICDKBBAZLK-UHFFFAOYSA-N 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- SPXOTSHWBDUUMT-UHFFFAOYSA-M 4-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=C(S([O-])(=O)=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-M 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- HHLQTIUKGYQQOD-UHFFFAOYSA-N 5-chloro-1-(3-fluorophenyl)-3h-2,1-benzoxaborole Chemical compound FC1=CC=CC(B2C3=CC=C(Cl)C=C3CO2)=C1 HHLQTIUKGYQQOD-UHFFFAOYSA-N 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000589291 Acinetobacter Species 0.000 description 1
- 241000588626 Acinetobacter baumannii Species 0.000 description 1
- 241000186041 Actinomyces israelii Species 0.000 description 1
- 241000701242 Adenoviridae Species 0.000 description 1
- 241000589155 Agrobacterium tumefaciens Species 0.000 description 1
- 241001545522 Aguacate virus Species 0.000 description 1
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical class NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 208000003829 American Hemorrhagic Fever Diseases 0.000 description 1
- 206010001935 American trypanosomiasis Diseases 0.000 description 1
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 description 1
- 240000000662 Anethum graveolens Species 0.000 description 1
- 108020005098 Anticodon Proteins 0.000 description 1
- 240000005528 Arctium lappa Species 0.000 description 1
- 241000712892 Arenaviridae Species 0.000 description 1
- 201000009695 Argentine hemorrhagic fever Diseases 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- 241000228197 Aspergillus flavus Species 0.000 description 1
- WTQNMYBQCBGAPV-UHFFFAOYSA-N B(O)(OC1=CC(=CC=C1)Cl)OC2=CC=CC=C2CCOCOC Chemical compound B(O)(OC1=CC(=CC=C1)Cl)OC2=CC=CC=C2CCOCOC WTQNMYBQCBGAPV-UHFFFAOYSA-N 0.000 description 1
- YCEGGNNGACCHFZ-UHFFFAOYSA-N B1OC=CC=C1 Chemical compound B1OC=CC=C1 YCEGGNNGACCHFZ-UHFFFAOYSA-N 0.000 description 1
- 241000193738 Bacillus anthracis Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 102100026189 Beta-galactosidase Human genes 0.000 description 1
- 241000228405 Blastomyces dermatitidis Species 0.000 description 1
- 208000034200 Bolivian hemorrhagic fever Diseases 0.000 description 1
- 241000589567 Brucella abortus Species 0.000 description 1
- 206010006500 Brucellosis Diseases 0.000 description 1
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 description 1
- PSXLCTPHDAEPLK-UHFFFAOYSA-N CC(C)[Mg] Chemical compound CC(C)[Mg] PSXLCTPHDAEPLK-UHFFFAOYSA-N 0.000 description 1
- 101150102024 CDC60 gene Proteins 0.000 description 1
- BPUPXIJIEDVDJW-UHFFFAOYSA-N COCN(CC(C(C1=CC(Cl)=CC=C1)=CC=C1)=C1OB(O)O)COC Chemical compound COCN(CC(C(C1=CC(Cl)=CC=C1)=CC=C1)=C1OB(O)O)COC BPUPXIJIEDVDJW-UHFFFAOYSA-N 0.000 description 1
- BROWNFLMWQDUFH-UHFFFAOYSA-N COCOCC1=C(C=CC=C1)OBOC1=C(C=CC=C1)COCOC Chemical compound COCOCC1=C(C=CC=C1)OBOC1=C(C=CC=C1)COCOC BROWNFLMWQDUFH-UHFFFAOYSA-N 0.000 description 1
- 244000197813 Camelina sativa Species 0.000 description 1
- 241000589874 Campylobacter fetus Species 0.000 description 1
- 241000589875 Campylobacter jejuni Species 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241001647378 Chlamydia psittaci Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
- BHYOQNUELFTYRT-UHFFFAOYSA-N Cholesterol sulfate Natural products C1C=C2CC(OS(O)(=O)=O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 BHYOQNUELFTYRT-UHFFFAOYSA-N 0.000 description 1
- SBUKLPSBNFWJCU-UHFFFAOYSA-N ClIBr Chemical group ClIBr SBUKLPSBNFWJCU-UHFFFAOYSA-N 0.000 description 1
- 241000193163 Clostridioides difficile Species 0.000 description 1
- 241000193155 Clostridium botulinum Species 0.000 description 1
- 241000193468 Clostridium perfringens Species 0.000 description 1
- 241000193449 Clostridium tetani Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000709687 Coxsackievirus Species 0.000 description 1
- 201000007336 Cryptococcosis Diseases 0.000 description 1
- 241000223936 Cryptosporidium parvum Species 0.000 description 1
- 241000186427 Cutibacterium acnes Species 0.000 description 1
- 241000701022 Cytomegalovirus Species 0.000 description 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 description 1
- 102000016928 DNA-directed DNA polymerase Human genes 0.000 description 1
- 108010014303 DNA-directed DNA polymerase Proteins 0.000 description 1
- 241000725619 Dengue virus Species 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- 101100186820 Drosophila melanogaster sicily gene Proteins 0.000 description 1
- 241001466953 Echovirus Species 0.000 description 1
- 241000224432 Entamoeba histolytica Species 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241000194031 Enterococcus faecium Species 0.000 description 1
- 241000991587 Enterovirus C Species 0.000 description 1
- 206010015146 Erysipeloid Diseases 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 208000001860 Eye Infections Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000589602 Francisella tularensis Species 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- 241000699694 Gerbillinae Species 0.000 description 1
- 241000224467 Giardia intestinalis Species 0.000 description 1
- 241001043186 Gibbium Species 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 241000606768 Haemophilus influenzae Species 0.000 description 1
- 241000590002 Helicobacter pylori Species 0.000 description 1
- 241000700739 Hepadnaviridae Species 0.000 description 1
- 241000700721 Hepatitis B virus Species 0.000 description 1
- 206010019851 Hepatotoxicity Diseases 0.000 description 1
- 208000009889 Herpes Simplex Diseases 0.000 description 1
- 241000700586 Herpesviridae Species 0.000 description 1
- 241000228404 Histoplasma capsulatum Species 0.000 description 1
- 241000430519 Human rhinovirus sp. Species 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical class [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- 229920001612 Hydroxyethyl starch Polymers 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 240000007597 Hymenaea verrucosa Species 0.000 description 1
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 108010059881 Lactase Proteins 0.000 description 1
- 241000194036 Lactococcus Species 0.000 description 1
- 208000004204 Larva Migrans Diseases 0.000 description 1
- 206010023927 Lassa fever Diseases 0.000 description 1
- 241000589242 Legionella pneumophila Species 0.000 description 1
- 241000222738 Leishmania aethiopica Species 0.000 description 1
- 241000178949 Leishmania chagasi Species 0.000 description 1
- 241000222727 Leishmania donovani Species 0.000 description 1
- 241000222697 Leishmania infantum Species 0.000 description 1
- 241000012072 Leishmania mexicana venezuelensis Species 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 206010066945 Lichen striatus Diseases 0.000 description 1
- 241000711828 Lyssavirus Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001291474 Malassezia globosa Species 0.000 description 1
- 241001291477 Malassezia restricta Species 0.000 description 1
- 241001291475 Malassezia slooffiae Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 201000005505 Measles Diseases 0.000 description 1
- 241000235048 Meyerozyma guilliermondii Species 0.000 description 1
- 241001260008 Microsporum equinum Species 0.000 description 1
- 208000005647 Mumps Diseases 0.000 description 1
- 241000545499 Mycobacterium avium-intracellulare Species 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 description 1
- 206010028698 Nail dystrophy Diseases 0.000 description 1
- 241000588653 Neisseria Species 0.000 description 1
- 241000588652 Neisseria gonorrhoeae Species 0.000 description 1
- 241000588650 Neisseria meningitidis Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000714209 Norwalk virus Species 0.000 description 1
- 244000020186 Nymphaea lutea Species 0.000 description 1
- 241000702259 Orbivirus Species 0.000 description 1
- 241000713112 Orthobunyavirus Species 0.000 description 1
- 241000150452 Orthohantavirus Species 0.000 description 1
- 241000712464 Orthomyxoviridae Species 0.000 description 1
- 206010033372 Pain and discomfort Diseases 0.000 description 1
- 208000005775 Parakeratosis Diseases 0.000 description 1
- 208000002606 Paramyxoviridae Infections Diseases 0.000 description 1
- 206010034016 Paronychia Diseases 0.000 description 1
- 241000029132 Paronychia Species 0.000 description 1
- 241000701945 Parvoviridae Species 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- 241000222831 Phialophora <Chaetothyriales> Species 0.000 description 1
- 201000000239 Phlebotomus fever Diseases 0.000 description 1
- 241000713137 Phlebovirus Species 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- 240000009188 Phyllostachys vivax Species 0.000 description 1
- 241000709664 Picornaviridae Species 0.000 description 1
- 241000224017 Plasmodium berghei Species 0.000 description 1
- 241000223960 Plasmodium falciparum Species 0.000 description 1
- 241000223821 Plasmodium malariae Species 0.000 description 1
- 206010035501 Plasmodium malariae infection Diseases 0.000 description 1
- 206010035502 Plasmodium ovale infection Diseases 0.000 description 1
- 241000233872 Pneumocystis carinii Species 0.000 description 1
- 241000711902 Pneumovirus Species 0.000 description 1
- 208000000474 Poliomyelitis Diseases 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 206010037575 Pustular psoriasis Diseases 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 102000014450 RNA Polymerase III Human genes 0.000 description 1
- 108010078067 RNA Polymerase III Proteins 0.000 description 1
- 206010037742 Rabies Diseases 0.000 description 1
- 241000711798 Rabies lyssavirus Species 0.000 description 1
- 206010037888 Rash pustular Diseases 0.000 description 1
- 208000033464 Reiter syndrome Diseases 0.000 description 1
- 241000702247 Reoviridae Species 0.000 description 1
- 241000702263 Reovirus sp. Species 0.000 description 1
- 206010038687 Respiratory distress Diseases 0.000 description 1
- 241000725643 Respiratory syncytial virus Species 0.000 description 1
- 241000712907 Retroviridae Species 0.000 description 1
- 241000711931 Rhabdoviridae Species 0.000 description 1
- 241000220010 Rhode Species 0.000 description 1
- 241000316848 Rhodococcus <scale insect> Species 0.000 description 1
- 241000606701 Rickettsia Species 0.000 description 1
- 241000606695 Rickettsia rickettsii Species 0.000 description 1
- 208000000705 Rift Valley Fever Diseases 0.000 description 1
- 241000713124 Rift Valley fever virus Species 0.000 description 1
- 241000710799 Rubella virus Species 0.000 description 1
- 241000315672 SARS coronavirus Species 0.000 description 1
- 241000235070 Saccharomyces Species 0.000 description 1
- 241000132889 Scedosporium Species 0.000 description 1
- 241000223255 Scytalidium Species 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 241000713311 Simian immunodeficiency virus Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 206010041736 Sporotrichosis Diseases 0.000 description 1
- 241000191963 Staphylococcus epidermidis Species 0.000 description 1
- 241001147691 Staphylococcus saprophyticus Species 0.000 description 1
- 241001478878 Streptobacillus Species 0.000 description 1
- 241000193985 Streptococcus agalactiae Species 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 1
- 241000710924 Togaviridae Species 0.000 description 1
- 241000223997 Toxoplasma gondii Species 0.000 description 1
- 201000005485 Toxoplasmosis Diseases 0.000 description 1
- 241000893963 Trichophyton concentricum Species 0.000 description 1
- 241001480046 Trichophyton schoenleinii Species 0.000 description 1
- 241000985906 Trichophyton soudanense Species 0.000 description 1
- 241001480048 Trichophyton tonsurans Species 0.000 description 1
- 241001480050 Trichophyton violaceum Species 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 241001442399 Trypanosoma brucei gambiense Species 0.000 description 1
- 241001442397 Trypanosoma brucei rhodesiense Species 0.000 description 1
- 241000223109 Trypanosoma cruzi Species 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- 208000034784 Tularaemia Diseases 0.000 description 1
- 208000001924 Tungiasis Diseases 0.000 description 1
- 241000700647 Variola virus Species 0.000 description 1
- 241001661641 Verrucosa Species 0.000 description 1
- 241000458243 Viana Species 0.000 description 1
- 241000607272 Vibrio parahaemolyticus Species 0.000 description 1
- 241000405217 Viola <butterfly> Species 0.000 description 1
- 206010047505 Visceral leishmaniasis Diseases 0.000 description 1
- 239000004164 Wax ester Substances 0.000 description 1
- 241000710886 West Nile virus Species 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000003152 Yellow Fever Diseases 0.000 description 1
- 241000710772 Yellow fever virus Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- PNDPGZBMCMUPRI-XXSWNUTMSA-N [125I][125I] Chemical compound [125I][125I] PNDPGZBMCMUPRI-XXSWNUTMSA-N 0.000 description 1
- SXFOJGKAIQWOJJ-UHFFFAOYSA-N [2-(methoxymethoxymethyl)phenyl]boronic acid Chemical compound COCOCC1=CC=CC=C1B(O)O SXFOJGKAIQWOJJ-UHFFFAOYSA-N 0.000 description 1
- XJKIIKZHUOSWBZ-UHFFFAOYSA-N [5-chloro-2-(5-chloro-3h-2,1-benzoxaborol-1-yl)phenyl]methanol Chemical compound OCC1=CC(Cl)=CC=C1B1C2=CC=C(Cl)C=C2CO1 XJKIIKZHUOSWBZ-UHFFFAOYSA-N 0.000 description 1
- QQIRAVWVGBTHMJ-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;lithium Chemical compound [Li].C[Si](C)(C)N[Si](C)(C)C QQIRAVWVGBTHMJ-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 108700010877 adenoviridae proteins Proteins 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000005237 alkyleneamino group Chemical group 0.000 description 1
- 125000005238 alkylenediamino group Chemical group 0.000 description 1
- 125000005530 alkylenedioxy group Chemical group 0.000 description 1
- 125000005529 alkyleneoxy group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 1
- 229960003942 amphotericin b Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229960005475 antiinfective agent Drugs 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000005101 aryl methoxy carbonyl group Chemical group 0.000 description 1
- 125000005165 aryl thioxy group Chemical group 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 229940091771 aspergillus fumigatus Drugs 0.000 description 1
- 229940065181 bacillus anthracis Drugs 0.000 description 1
- 229940028420 bactroban Drugs 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 108010005774 beta-Galactosidase Proteins 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 238000002306 biochemical method Methods 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- XQIMLPCOVYNASM-UHFFFAOYSA-N borole Chemical compound B1C=CC=C1 XQIMLPCOVYNASM-UHFFFAOYSA-N 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229940056450 brucella abortus Drugs 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229940055022 candida parapsilosis Drugs 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000019522 cellular metabolic process Effects 0.000 description 1
- 229940106189 ceramide Drugs 0.000 description 1
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 description 1
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 1
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 1
- BHYOQNUELFTYRT-DPAQBDIFSA-N cholesterol sulfate Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 BHYOQNUELFTYRT-DPAQBDIFSA-N 0.000 description 1
- SCKYRAXSEDYPSA-UHFFFAOYSA-N ciclopirox Chemical compound ON1C(=O)C=C(C)C=C1C1CCCCC1 SCKYRAXSEDYPSA-UHFFFAOYSA-N 0.000 description 1
- 229960003749 ciclopirox Drugs 0.000 description 1
- 229960004022 clotrimazole Drugs 0.000 description 1
- VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 description 1
- 239000011436 cob Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 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 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 210000000805 cytoplasm Anatomy 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000009429 distress Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 241001493065 dsRNA viruses Species 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- 229940007078 entamoeba histolytica Drugs 0.000 description 1
- 229940032049 enterococcus faecalis Drugs 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 210000003527 eukaryotic cell Anatomy 0.000 description 1
- 208000011323 eye infectious disease Diseases 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229940118764 francisella tularensis Drugs 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 229940047650 haemophilus influenzae Drugs 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 229940037467 helicobacter pylori Drugs 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- 208000005252 hepatitis A Diseases 0.000 description 1
- 231100000334 hepatotoxic Toxicity 0.000 description 1
- 230000003082 hepatotoxic effect Effects 0.000 description 1
- 201000005473 herpetic whitlow Diseases 0.000 description 1
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 1
- 229960002885 histidine Drugs 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 239000000710 homodimer Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 210000003284 horn Anatomy 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229940050526 hydroxyethylstarch Drugs 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000012678 infectious agent Substances 0.000 description 1
- 230000004941 influx Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- CBEQRNSPHCCXSH-UHFFFAOYSA-N iodine monobromide Chemical compound IBr CBEQRNSPHCCXSH-UHFFFAOYSA-N 0.000 description 1
- 229940044173 iodine-125 Drugs 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 229960004125 ketoconazole Drugs 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 229940116108 lactase Drugs 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 229940115932 legionella pneumophila Drugs 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 201000011486 lichen planus Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000033001 locomotion Effects 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- SDMCZCALYDCRBH-UHFFFAOYSA-N methoxymethyl(triphenyl)phosphanium Chemical class C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SDMCZCALYDCRBH-UHFFFAOYSA-N 0.000 description 1
- NOCGROPYCGRERZ-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 NOCGROPYCGRERZ-UHFFFAOYSA-M 0.000 description 1
- SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 1
- 208000020298 milker nodule Diseases 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000006682 monohaloalkyl group Chemical group 0.000 description 1
- 230000008450 motivation Effects 0.000 description 1
- 201000000626 mucocutaneous leishmaniasis Diseases 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 208000010805 mumps infectious disease Diseases 0.000 description 1
- MINDHVHHQZYEEK-HBBNESRFSA-N mupirocin Chemical compound C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@@H]1[C@@H](O)[C@@H](O)[C@H](C\C(C)=C\C(=O)OCCCCCCCCC(O)=O)OC1 MINDHVHHQZYEEK-HBBNESRFSA-N 0.000 description 1
- 229960003128 mupirocin Drugs 0.000 description 1
- DDHVILIIHBIMQU-YJGQQKNPSA-L mupirocin calcium hydrate Chemical compound O.O.[Ca+2].C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@@H]1[C@@H](O)[C@@H](O)[C@H](C\C(C)=C\C(=O)OCCCCCCCCC([O-])=O)OC1.C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@@H]1[C@@H](O)[C@@H](O)[C@H](C\C(C)=C\C(=O)OCCCCCCCCC([O-])=O)OC1 DDHVILIIHBIMQU-YJGQQKNPSA-L 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 125000001736 nosyl group Chemical group S(=O)(=O)(C1=CC=C([N+](=O)[O-])C=C1)* 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000003463 organelle Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- GCGYPHVQHXGABK-UHFFFAOYSA-N oxaborepine Chemical compound O1B=CC=CC=C1 GCGYPHVQHXGABK-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 230000005298 paramagnetic effect Effects 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 125000004660 phenylalkylthio group Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical class CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 125000006684 polyhaloalkyl group Polymers 0.000 description 1
- 229920005862 polyol Chemical group 0.000 description 1
- 150000003077 polyols Chemical group 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 229940055019 propionibacterium acne Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 229930194369 pseudomonic acid Natural products 0.000 description 1
- 208000029561 pustule Diseases 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 208000002574 reactive arthritis Diseases 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 210000003705 ribosome Anatomy 0.000 description 1
- 229940075118 rickettsia rickettsii Drugs 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 125000005630 sialyl group Chemical group 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 208000037946 swimming pool granuloma Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 239000006208 topical dosage form Substances 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical class OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 229940118696 vibrio cholerae Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000019386 wax ester Nutrition 0.000 description 1
- 229940051021 yellow-fever virus Drugs 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/69—Boron compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A61K31/7076—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Communicable Diseases (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75522705P | 2005-12-30 | 2005-12-30 | |
| US60/755.227 | 2005-12-30 | ||
| PCT/US2006/005542 WO2006089067A2 (en) | 2005-02-16 | 2006-02-16 | Boron-containing small molecules |
| USPCT/US2006/05542 | 2006-02-16 | ||
| US11/357,687 US7582621B2 (en) | 2005-02-16 | 2006-02-16 | Boron-containing small molecules |
| US11/357,687 | 2006-02-16 | ||
| US74636106P | 2006-05-03 | 2006-05-03 | |
| US60/746,361 | 2006-05-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20080110984A true KR20080110984A (ko) | 2008-12-22 |
Family
ID=38225302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020087018808A Withdrawn KR20080110984A (ko) | 2005-12-30 | 2006-08-16 | 보론함유 소분자 |
Country Status (11)
| Country | Link |
|---|---|
| US (14) | US7767657B2 (enExample) |
| EP (1) | EP1976536A4 (enExample) |
| JP (1) | JP2009526751A (enExample) |
| KR (1) | KR20080110984A (enExample) |
| CN (3) | CN106008583A (enExample) |
| AU (1) | AU2006333527B2 (enExample) |
| BR (1) | BRPI0621279B1 (enExample) |
| CA (1) | CA2635680A1 (enExample) |
| IL (1) | IL192402A (enExample) |
| RU (1) | RU2008131324A (enExample) |
| WO (1) | WO2007078340A2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160146785A (ko) * | 2014-05-05 | 2016-12-21 | 아나코르 파마슈티칼스 인코포레이티드 | 화합물 및 매니큐어 |
Families Citing this family (87)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUE026021T2 (en) * | 2005-02-16 | 2016-05-30 | Anacor Pharmaceuticals Inc | Biocidal boron phthalide (boronophthalide) compounds |
| US7793666B2 (en) * | 2005-07-28 | 2010-09-14 | Innovation Biomedical Devices, Inc. | Apparatus and method for treatment of infected nail |
| CN106008583A (zh) | 2005-12-30 | 2016-10-12 | 安纳考尔医药公司 | 含硼的小分子 |
| BRPI0708051A2 (pt) * | 2006-02-16 | 2011-05-17 | Anacor Pharmaceuticals Inc | moléculas pequenas contendo boro como agentes antiflamatórios |
| JP2009536660A (ja) * | 2006-05-02 | 2009-10-15 | アナコール ファーマシューティカルズ，インコーポレイテッド | 加水分解耐性ホウ素含有治療剤及びその使用方法 |
| JO3598B1 (ar) * | 2006-10-10 | 2020-07-05 | Infinity Discovery Inc | الاحماض والاسترات البورونية كمثبطات اميد هيدروليز الحامض الدهني |
| JO3396B1 (ar) | 2007-06-20 | 2019-10-20 | Anacor Pharmaceuticals Inc | جزيئات صغيرة تحتوي على البورون |
| US20090175810A1 (en) | 2008-01-03 | 2009-07-09 | Gareth Winckle | Compositions and methods for treating diseases of the nail |
| KR101672511B1 (ko) | 2008-03-06 | 2016-11-03 | 아나코르 파마슈티칼스 인코포레이티드 | 소염제로써 붕소가 함유된 소분자 |
| WO2009126691A1 (en) | 2008-04-09 | 2009-10-15 | Infinity Pharmaceuticals, Inc | Inhibitors of fatty acid amide hydrolase |
| WO2009140309A2 (en) * | 2008-05-12 | 2009-11-19 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| WO2010011354A2 (en) * | 2008-07-25 | 2010-01-28 | Innovation Biomedical Devices, Inc. | Enchanced trans-keratin drug delivery |
| EP2348863A4 (en) * | 2008-09-04 | 2012-03-07 | Anacor Pharmaceuticals Inc | BORN SMALL MOLECULES |
| US8461336B2 (en) * | 2008-09-04 | 2013-06-11 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| US9493489B2 (en) * | 2008-10-15 | 2016-11-15 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules as anti-protozoal agents |
| KR20110111407A (ko) * | 2008-12-17 | 2011-10-11 | 아나코르 파마슈티칼스 인코포레이티드 | (ｓ)-３-아미노메틸-７-(３-히드록시-프로폭시)-３ｈ-벤조〔ｃ〕〔１,２〕옥사보롤-１-올의 다형태 |
| WO2010118159A1 (en) | 2009-04-07 | 2010-10-14 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| EP2416660B1 (en) | 2009-04-07 | 2014-07-02 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| WO2011017125A1 (en) | 2009-07-28 | 2011-02-10 | Anacor Pharmaceuticals, Inc. | Trisubstituted boron-containing molecules |
| US9440994B2 (en) * | 2009-08-14 | 2016-09-13 | Anacor Pharmaceuticals, Inc. | Boron containing small molecules as antiprotozoal agents |
| WO2011019616A1 (en) | 2009-08-14 | 2011-02-17 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules as antiprotozoal agents |
| WO2011019612A1 (en) | 2009-08-14 | 2011-02-17 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules as antiprotozoal agents |
| US20110207701A1 (en) * | 2009-08-19 | 2011-08-25 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules as antiprotozoal agents |
| WO2011037731A1 (en) | 2009-09-25 | 2011-03-31 | Anacor Pharmaceuticals, Inc. | Boron containing small molecules |
| US8979820B2 (en) | 2009-10-09 | 2015-03-17 | Cynthia S. Bailey | Method and apparatus for improving the appearance of nails affected by onychomycosis through the topical application of an aqueous solution containing boric acid and camphor or other terpenes |
| US9346834B2 (en) | 2009-10-20 | 2016-05-24 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules as antiprotozoal agents |
| WO2011060196A1 (en) | 2009-11-11 | 2011-05-19 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| WO2011063293A1 (en) * | 2009-11-20 | 2011-05-26 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules as antihelminth agents |
| WO2011094450A1 (en) | 2010-01-27 | 2011-08-04 | Anacor Pharmaceuticals, Inc | Boron-containing small molecules |
| AU2011213072C1 (en) | 2010-02-03 | 2016-12-15 | Infinity Pharmaceuticals, Inc. | Fatty acid amide hydrolase inhibitors |
| AP2012006482A0 (en) | 2010-03-19 | 2012-10-31 | Anacor Pharmacueticals Inc | Boron-containing small molecules as anti-protozoalagent |
| US8039494B1 (en) | 2010-07-08 | 2011-10-18 | Dow Pharmaceutical Sciences, Inc. | Compositions and methods for treating diseases of the nail |
| HRP20211762T1 (hr) | 2010-09-07 | 2022-02-18 | Anacor Pharmaceuticals, Inc. | Derivati benzoksaborola za liječenje bakterijskih infekcija |
| WO2013049424A1 (en) | 2011-09-28 | 2013-04-04 | Wisconsin Alumni Research Foundation | Catalytic conversion of cellulose to fuels and chemicals using boronic acids |
| BR112014008186A2 (pt) | 2011-10-07 | 2017-04-11 | Syngenta Participations Ag | método para proteção de plantas úteis ou material de propagação de plantas |
| AR088669A1 (es) | 2011-11-21 | 2014-06-25 | Lilly Co Eli | Derivados de dihidrodibenzo[c][1,2]oxaborol y dihidroisoxazol utiles para el control de ectoparasitos |
| AR088668A1 (es) * | 2011-11-21 | 2014-06-25 | Lilly Co Eli | Moleculas pequeñas que contienen boro |
| US9732101B2 (en) | 2012-01-18 | 2017-08-15 | Wisconsin Alumni Research Foundation | Bioreversible boronates for delivery of molecules into cells |
| WO2013110005A1 (en) * | 2012-01-18 | 2013-07-25 | Wisconsin Alumni Research Foundation | Boronate-mediated delivery of molecules into cells |
| US20150080342A1 (en) * | 2012-04-14 | 2015-03-19 | Anacor Pharmaceuticals, Inc. | Benzoxaborole compounds and uses thereof |
| WO2014007831A1 (en) | 2012-07-06 | 2014-01-09 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| US8980544B2 (en) | 2012-11-27 | 2015-03-17 | The Penn State Research Foundation | Boronic and borinic acid compounds as inhibitors of sulfenic acid-containing proteins |
| US9585396B2 (en) | 2013-01-30 | 2017-03-07 | Agrofresh Inc. | Volatile applications against pathogens |
| UY35287A (es) | 2013-01-30 | 2014-08-29 | Dow Agrosciences Llc | Uso de benzoxaborolas como agentes antimicrobianos volátiles en carnes, plantas o partes de plantas. |
| US8669207B1 (en) | 2013-01-30 | 2014-03-11 | Dow Agrosciences, Llc. | Compounds and compositions |
| US11039617B2 (en) | 2013-01-30 | 2021-06-22 | Agrofresh Inc. | Large scale methods of uniformly coating packaging surfaces with a volatile antimicrobial to preserve food freshness |
| US10070649B2 (en) | 2013-01-30 | 2018-09-11 | Agrofresh Inc. | Volatile applications against pathogens |
| AP2015008638A0 (en) | 2013-02-01 | 2015-08-31 | Anacor Pharmaceuticals Inc | Boron-containing small molecules as antiprotozoal agents |
| AR094961A1 (es) | 2013-03-15 | 2015-09-09 | Lilly Co Eli | 1-hidroxi-benzooxaboroles como agentes antiparasitarios |
| WO2014173880A1 (en) * | 2013-04-22 | 2014-10-30 | Syngenta Participations Ag | Novel microbiocides |
| KR101636431B1 (ko) | 2013-07-30 | 2016-07-05 | 동아에스티 주식회사 | 트리사이클릭 벤즈옥사보롤 화합물, 이의 제조방법 및 용도 |
| EP3030519B1 (en) | 2013-08-09 | 2022-01-05 | Glaxosmithkline Intellectual Property (No. 2) Limited | Tricyclic benzoxaborole compounds and uses thereof |
| MX363386B (es) | 2013-10-03 | 2019-03-20 | Dow Pharmaceutical Sciences | Formulaciones de efinaconazol estabilizadas. |
| CN105848719A (zh) | 2013-11-22 | 2016-08-10 | 道尔医药科学公司 | 抗感染的方法、组合物和装置 |
| EP3086797B1 (en) | 2013-12-23 | 2018-05-23 | Medical Brands Research B.V. | Dermatological composition based on algae and olive leaf extracts |
| RU2016137000A (ru) | 2014-02-17 | 2018-03-22 | Зингента Партисипейшнс Аг | Микробиоцидно активные бензоксаборолы |
| US11039621B2 (en) | 2014-02-19 | 2021-06-22 | Corning Incorporated | Antimicrobial glass compositions, glasses and polymeric articles incorporating the same |
| US11039620B2 (en) | 2014-02-19 | 2021-06-22 | Corning Incorporated | Antimicrobial glass compositions, glasses and polymeric articles incorporating the same |
| US9622483B2 (en) | 2014-02-19 | 2017-04-18 | Corning Incorporated | Antimicrobial glass compositions, glasses and polymeric articles incorporating the same |
| KR20170007347A (ko) * | 2014-05-12 | 2017-01-18 | 애그로프레쉬 인크. | 병원체에 대항하는 휘발성 적용 |
| EP3164404B1 (en) | 2014-07-01 | 2019-04-03 | Daiichi Sankyo Company, Limited | Tricyclic benzoxaboroles as antibacterial agents |
| US20160051565A1 (en) * | 2014-08-20 | 2016-02-25 | Professional Compounding Centers Of America (Pcca) | Transdermal Pharmaceutical Compositions Including Testosterone and an Aromatase Inhibitor |
| BR112017008211A2 (pt) | 2014-10-21 | 2017-12-26 | Hexima Ltd | método para inibir infecção de um patógeno fúngico, formulação tópica ou extrato celular ou vegetal e uso de uma formulação ou extrato celular ou vegetal |
| MA41494B1 (fr) | 2015-02-12 | 2020-10-28 | Glaxosmithkline Ip No 2 Ltd | Composés benzoxaborole substitués en position 4 et utilisations associées |
| CA2981773C (en) | 2015-04-09 | 2022-03-15 | The Penn State Research Foundation | Synergistic benzoxaborole-containing anti-fungicidal composition |
| KR20170136570A (ko) | 2015-04-09 | 2017-12-11 | 아나코르 파마슈티칼스 인코포레이티드 | 항원생동물제로서의 붕소-함유 소분자 |
| WO2017024022A1 (en) * | 2015-08-06 | 2017-02-09 | The Penn State Research Foundation | Benzoxaborole-containing coating resistant to cellulose-supportable fungus |
| WO2017031041A1 (en) * | 2015-08-17 | 2017-02-23 | Channel Therapeutics, Inc. | Functionalized aminobenzoboroxoles |
| US10874679B2 (en) | 2016-03-02 | 2020-12-29 | Bill & Melinda Gates Foundation | Boron-containing small molecules |
| WO2017151489A1 (en) | 2016-03-02 | 2017-09-08 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| US10611781B2 (en) | 2016-03-02 | 2020-04-07 | Bill And Melinda Gates Foundation | Boron-containing small molecules |
| EP3426029B1 (en) | 2016-03-07 | 2023-08-30 | AgroFresh Inc. | Synergistic methods of using benzoxaborole compounds and preservative gases as an antimicrobial for crops |
| WO2017183043A1 (en) * | 2016-04-18 | 2017-10-26 | Biophore India Pharmaceuticals Pvt. Ltd. | Novel process for the preparation of tavaborole, its novel polymorphic forms and the polymorphs thereof |
| US11447506B2 (en) | 2016-05-09 | 2022-09-20 | Anacor Pharmaceuticals, Inc. | Crystal forms of crisaborole in free form and preparation method and use thereof |
| JP2019520321A (ja) | 2016-05-09 | 2019-07-18 | アナコール ファーマシューティカルズ，インコーポレイテッド | フリー体のクリサボロールの結晶形ならびにそれらの調製方法および使用 |
| EA201892639A1 (ru) | 2016-06-03 | 2019-06-28 | Басф Се | Соединения бензоксаборола |
| WO2019190503A1 (en) * | 2018-03-28 | 2019-10-03 | Cove Bio Llc | Methods and compositions for treating parkinson's disease |
| WO2018150327A1 (en) * | 2017-02-14 | 2018-08-23 | Wavelength Enterprises Ltd | Crisaborole production process |
| CN109206446B (zh) * | 2017-11-14 | 2021-08-03 | 深圳市塔吉瑞生物医药有限公司 | 一种取代的含硼的化合物及包含该化合物的药物组合物 |
| CA3120976A1 (en) | 2017-11-30 | 2019-06-06 | Boragen, Inc. | Benzoxaborole compounds and formulations thereof |
| AU2019325436B2 (en) | 2018-08-18 | 2023-10-26 | 5Metis, Inc. | Solid forms of substituted benzoxaborole and compositions thereof |
| WO2020123881A1 (en) * | 2018-12-12 | 2020-06-18 | Boragen, Inc. | Boron containing compounds and their uses |
| EP3956729A1 (en) * | 2019-04-16 | 2022-02-23 | Basf Se | Composition for avoiding pattern collapse when treating patterned materials with line-space dimensions of 50 nm or below comprising a boron-type additive |
| WO2021021932A1 (en) * | 2019-07-30 | 2021-02-04 | Boragen, Inc. | Flow reaction process for manufacture of boron-containing agrochemicals |
| US20230340530A1 (en) | 2020-08-31 | 2023-10-26 | Pfizer Inc. | Methods of Protecting RNA |
| CN114249756A (zh) * | 2020-09-21 | 2022-03-29 | 广东和博制药有限公司 | 一种他伐硼罗的合成方法 |
| CN115894575B (zh) * | 2022-08-10 | 2024-11-19 | 河南大学 | 一种由非经典三层笼状簇构筑的多金属氧酸盐材料及其制备方法与应用 |
Family Cites Families (110)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2260336A (en) * | 1939-10-16 | 1941-10-28 | Dow Chemical Co | Method of preparation of organic borates |
| US2741548A (en) | 1954-10-15 | 1956-04-10 | Standard Oil Co | Leaded motor fuel containing boron compounds |
| GB791688A (en) | 1955-05-12 | 1958-03-12 | May & Baker Ltd | Improvements in or relating to pyrazole derivatives |
| US3093659A (en) | 1956-06-20 | 1963-06-11 | Pfizer & Co C | Antifungal and insecticidal halokojic acid metal complexes |
| US3104255A (en) | 1960-06-16 | 1963-09-17 | Standard Oil Co | Telomerization of unsaturated hydrocarbons with alkylene glycol borates and telomeric products obtained thereby |
| US3297525A (en) | 1962-10-19 | 1967-01-10 | Merck & Co Inc | Fungicidal compositions comprising salicylates of 8 hydroxy quinoline carboxylic esters |
| NL134354C (enExample) | 1963-05-23 | |||
| US3686398A (en) * | 1970-07-20 | 1972-08-22 | Chevron Res | 10,9-boroxarophenanthrene as fungicides |
| US3816472A (en) | 1972-07-06 | 1974-06-11 | Schering Corp | Azido analogs of griseofulvin |
| GB1396904A (en) * | 1972-08-11 | 1975-06-11 | Ici Ltd | Method for the control of micro-organisms |
| US4766113A (en) * | 1975-10-24 | 1988-08-23 | Chapman Chemical Company | Antimicrobial compositions and methods of using same |
| US4602011A (en) * | 1975-10-24 | 1986-07-22 | Chapman Chemical Company | Antimicrobial compositions and methods of using same |
| AT354187B (de) | 1976-11-22 | 1979-12-27 | Hoffmann La Roche | Fungizides mittel |
| US4716035A (en) * | 1985-05-24 | 1987-12-29 | The Procter & Gamble Company | Oral compositions and methods for treating gingivitis |
| JPH0676285B2 (ja) | 1985-11-01 | 1994-09-28 | 三井東圧化学株式会社 | ベンジルアミン誘導体、その製造法およびその用途 |
| US5962498A (en) * | 1986-06-11 | 1999-10-05 | Procyon Pharmaceuticals, Inc. | Protein kinase C modulators. C. indolactam structural-types with anti-inflammatory activity |
| US4894220A (en) * | 1987-01-30 | 1990-01-16 | Colgate-Palmolive Company | Antibacterial antiplaque oral composition |
| DE3720147A1 (de) | 1987-06-16 | 1988-12-29 | Hoechst Ag | Antimykotisch wirksamer nagellack sowie verfahren zu dessen herstellung |
| US4977268A (en) | 1988-04-08 | 1990-12-11 | Duke University | Boron dipeptide compounds |
| US4919934A (en) | 1989-03-02 | 1990-04-24 | Richardson-Vicks Inc. | Cosmetic sticks |
| SG47101A1 (en) * | 1992-07-31 | 1998-03-20 | Us Bioscience | Crystalline amifostine compositions and methods for the preparation and use of same |
| US5348947A (en) * | 1993-05-07 | 1994-09-20 | American Cyanamid Company | Diarylboron ester and thioester fungicidal agents |
| US5348948A (en) * | 1993-05-07 | 1994-09-20 | American Cyanamid Company | 2,2-diaryl-1-(oxa and thia)-2a-azonia-2-borataacenaphthene fungicidal |
| WO1995008918A1 (en) * | 1993-09-29 | 1995-04-06 | Gist-Brocades N.V. | A novel antifungal composition |
| US5594151A (en) * | 1994-01-28 | 1997-01-14 | Prolinx, Inc. | Phenylboronic acid complexing reagents derived from aminosalicylic acid |
| GB9411587D0 (en) * | 1994-06-09 | 1994-08-03 | Zeneca Ltd | Compound, composition and use |
| US5498407A (en) | 1994-10-24 | 1996-03-12 | Atlas; Sheldon M. | Poly(2-hydroxyethyl methacrylate) and all copolymers of poly-HEMA fibers and cosmetic compositions containing same |
| US6083903A (en) * | 1994-10-28 | 2000-07-04 | Leukosite, Inc. | Boronic ester and acid compounds, synthesis and uses |
| US5696164A (en) | 1994-12-22 | 1997-12-09 | Johnson & Johnson Consumer Products, Inc. | Antifungal treatment of nails |
| GB9500856D0 (en) | 1995-01-17 | 1995-03-08 | Zeneca Ltd | Composition and use |
| JPH09124620A (ja) | 1995-10-11 | 1997-05-13 | Bristol Myers Squibb Co | 置換ビフェニルスルホンアミドエンドセリン拮抗剤 |
| US6766183B2 (en) | 1995-11-22 | 2004-07-20 | Medtronic Minimed, Inc. | Long wave fluorophore sensor compounds and other fluorescent sensor compounds in polymers |
| GB9604926D0 (en) * | 1996-03-08 | 1996-05-08 | Sandoz Ltd | Organic compounds |
| WO1997048697A1 (en) * | 1996-06-19 | 1997-12-24 | Rhone-Poulenc Rorer Limited | Substituted azabicylic compounds and their use as inhibitors of the production of tnf and cyclic amp phosphodiesterase |
| US5831046A (en) * | 1996-08-05 | 1998-11-03 | Prolinx, Incorporated | Boronic acid-contaning nucleic acid monomers |
| WO1998012206A1 (en) | 1996-09-19 | 1998-03-26 | The Board Of Trustees Of Leland Stanford Jr. University | Dna adenine methyltransferases and uses thereof |
| EP0947498B1 (en) | 1996-12-02 | 2004-09-15 | Chisso Corporation | Optically active nitro alcohol derivatives, optically active amino alcohol derivatives, and process for preparing the same |
| US6221640B1 (en) | 1997-05-14 | 2001-04-24 | Cubist Pharmaceuticals, Inc. | Enterococcal aminoacyl-trna synthetase proteins, nucleic acids and strains comprising same |
| US6140328A (en) * | 1997-12-12 | 2000-10-31 | Rutgers, The State University Of New Jersey | Heterocyclic cytotoxic agents |
| EP0983037B1 (en) | 1998-02-09 | 2003-05-02 | MacroChem Corporation | Antifungal nail lacquer |
| AU745321B2 (en) | 1998-04-17 | 2002-03-21 | Bertek Pharmaceuticals, Inc. | Topical formulations for the treatment of nail fungal diseases |
| DE19829947A1 (de) | 1998-07-04 | 2000-01-05 | Bayer Ag | Elektrolumineszierende Anordnungen mit Bor-Chelaten |
| US6462036B1 (en) | 1998-11-06 | 2002-10-08 | Basf Aktiengesellschaft | Tricyclic pyrazole derivatives |
| TR200102277T2 (tr) | 1998-11-06 | 2002-01-21 | Basf Aktiengesellschaft Ag. | Üç halkalı (Trisiklik) pirazol türevleri |
| EP1155698A4 (en) | 1999-01-29 | 2003-01-15 | Nitto Kasei Co Ltd | ORGANOBORAL COMPOUNDS HAVING COCCIDIOSTAT ACTIVITY |
| JP2003501431A (ja) | 1999-05-25 | 2003-01-14 | ザ ペン ステート リサーチ ファウンデイション | Ｄｎａメチル基転移酵素阻害剤 |
| DE60032614D1 (de) | 1999-08-25 | 2007-02-08 | Ambergen Inc | Verfahren zur erkennung, analyse und isolierung von freiwerdenden proteinen |
| US6306628B1 (en) * | 1999-08-25 | 2001-10-23 | Ambergen, Incorporated | Methods for the detection, analysis and isolation of Nascent proteins |
| AU7995300A (en) * | 1999-10-05 | 2001-05-10 | Bethesda Pharmaceuticals, Inc. | Dithiolane derivatives |
| JP2003519187A (ja) | 2000-01-06 | 2003-06-17 | マランテック ホールディング リミテッド ライアビリティ カンパニー | 癌管理のための電子活性化合物の使用方法 |
| US7074392B1 (en) | 2000-03-27 | 2006-07-11 | Taro Pharmaceutical Industries Limited | Controllled delivery system of antifungal and keratolytic agents for local treatment of fungal infections |
| US6521619B2 (en) | 2000-06-29 | 2003-02-18 | Icos Corporation | Aryl phenylcyclopropyl sulfide derivatives and their use as cell adhesion inhibiting anti-inflammatory and immune suppressive agents |
| DE10032017A1 (de) | 2000-07-01 | 2002-01-10 | Clariant Gmbh | Verfahren zur Herstellung hochreiner Formylphenylboronsäuren |
| WO2002006316A2 (en) * | 2000-07-14 | 2002-01-24 | Zycos, Inc. | Alpha-msh related compounds and methods of use |
| CA2428191A1 (en) * | 2000-11-07 | 2002-05-30 | Bristol-Myers Squibb Company | Acid derivatives useful as serine protease inhibitors |
| EP1339725B1 (en) | 2000-11-30 | 2006-11-22 | The Penn State Research Foundation | Dna methyl transferase inhibitors |
| DE10110051C2 (de) * | 2001-03-02 | 2003-07-03 | Clariant Gmbh | Verfahren zur Herstellung von Boron- und Borinsäuren |
| US6878365B2 (en) * | 2001-03-10 | 2005-04-12 | James Edward Brehove | Topical application for treating toenail fungus |
| ES2332090T3 (es) | 2001-04-06 | 2010-01-26 | Biocryst Pharmaceuticals, Inc. | Compuestos biarilicos como inhibidores de serina proteasa. |
| GB0117645D0 (en) * | 2001-07-19 | 2001-09-12 | Isis Innovation | Therapeutic stratergies for prevention and treatment of alzheimers disease |
| EP1416799A4 (en) * | 2001-07-23 | 2004-11-10 | Univ Ramot | METHODS AND COMPOSITIONS FOR TREATING FUNGAL INFECTIONS |
| DE10143979A1 (de) * | 2001-09-07 | 2003-03-27 | Clariant Gmbh | Verfahren zur Herstellung von Bisallylboranen und nicht-aromatischen Boronsäuren |
| WO2003033002A1 (en) | 2001-10-11 | 2003-04-24 | Ono Pharmaceutical Co | Intracellular calcium concentration increase inhibitors |
| JP4209659B2 (ja) | 2001-11-15 | 2009-01-14 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | アミジノ誘導体並びにそれを用いた抗血液凝固剤および血栓症治療剤 |
| WO2003059916A2 (en) | 2002-01-10 | 2003-07-24 | The Pennsylvania State Research Foundation | Methods for the preparation of alkyl diaryl borinates and complexed diarylborinic acids |
| IL166156A0 (en) | 2002-07-09 | 2006-01-15 | Point Therapeutics Inc | Boroproline compound combination therapy |
| AU2003291403A1 (en) * | 2002-11-08 | 2004-06-03 | Neurogen Corporation | 3-substituted-6-aryl pyridined as ligands of c5a receptors |
| US7446236B2 (en) | 2002-12-02 | 2008-11-04 | Solvias Ag | Catalytic hydrogenation of carbon-heteroatom double bonds |
| US7390806B2 (en) * | 2002-12-18 | 2008-06-24 | Anacor Pharmaceuticals, Inc. | Antibiotics containing borinic acid complexes and methods of use |
| EP1581500A4 (en) * | 2002-12-18 | 2008-03-05 | Anacor Pharmaceuticals Inc | ANTIBIOTICS CONTAINING BORINIC ACID COMPLEXES AND METHODS OF USE |
| CA2519107A1 (en) | 2003-03-14 | 2004-09-23 | Astrazeneca Ab | Novel fused triazolones and the uses thereof |
| US20050125852A1 (en) * | 2003-05-09 | 2005-06-09 | Sugen, Inc. | Novel kinases |
| US7465836B2 (en) | 2003-06-16 | 2008-12-16 | Anacor Pharmaceuticals, Inc. | Hydrolytically-resistant boron-containing therapeutics and methods of use |
| JP2005022986A (ja) | 2003-06-30 | 2005-01-27 | Sankyo Co Ltd | Ｅｄｇ受容体拮抗作用を有するアルキン誘導体 |
| DE602004008631T2 (de) * | 2003-07-03 | 2008-07-10 | F. Hoffmann-La Roche Ag | Duale nk1/nk3 antagonisten zur behandlung von schizophrenie |
| WO2005066172A1 (en) | 2003-12-29 | 2005-07-21 | 3M Innovative Properties Company | Piperazine, [1,4]diazepane, [1,4]diazocane, and [1,5]diazocane fused imidazo ring compounds |
| EP2335722B1 (en) * | 2004-05-12 | 2019-03-13 | The Brigham and Women's Hospital, Inc. | Use of gelsolin to treat infections |
| JP2007537296A (ja) | 2004-05-14 | 2007-12-20 | アボット・ラボラトリーズ | 治療薬としてのキナーゼ阻害薬 |
| AR049915A1 (es) | 2004-06-14 | 2006-09-13 | Anacor Pharmaceuticals Inc | Compuestos con contenido de boro y metodos de uso de los mismos |
| KR100624238B1 (ko) * | 2004-06-22 | 2006-09-19 | 한국화학연구원 | 알파-아릴메톡시아크릴레이트 유도체를 함유하는 대사성골 질환의 예방 및 치료용 약학 조성물 |
| US20060111388A1 (en) | 2004-11-19 | 2006-05-25 | University Of North Texas Health Science Center At Fort Worth | Phenanthroline and derivatives thereof used to lower intraocular pressure in an affected eye |
| GB0501944D0 (en) | 2005-01-31 | 2005-03-09 | Univ Cambridge Tech | Compounds for use in chemical detection and/or quantitation |
| HUE026021T2 (en) | 2005-02-16 | 2016-05-30 | Anacor Pharmaceuticals Inc | Biocidal boron phthalide (boronophthalide) compounds |
| US7919422B2 (en) | 2005-03-08 | 2011-04-05 | Agency For Science, Technology And Research | Chiral bisoxazoline catalysts |
| PE20061303A1 (es) * | 2005-03-30 | 2006-12-07 | Astion Dev As | Composicion farmaceutica que comprende oxaprozina |
| US20070028682A1 (en) | 2005-08-04 | 2007-02-08 | Geon Sagong | System for measuring fluid level using acoustic impedance matching |
| US20080234229A1 (en) | 2005-08-18 | 2008-09-25 | Auspex Pharmaceuticals, Inc. | Novel Therapeutic Agents for the Treatment of Cancer, Metabolic Diseases and Skin Disorders |
| CN106008583A (zh) | 2005-12-30 | 2016-10-12 | 安纳考尔医药公司 | 含硼的小分子 |
| BRPI0708051A2 (pt) | 2006-02-16 | 2011-05-17 | Anacor Pharmaceuticals Inc | moléculas pequenas contendo boro como agentes antiflamatórios |
| US20070286822A1 (en) * | 2006-06-12 | 2007-12-13 | Anacor Pharmaceuticals Inc. | Compounds for the Treatment of Periodontal Disease |
| RU2008152367A (ru) | 2006-06-12 | 2010-07-20 | Анакор Фармасьютикалз, Инк. (Us) | Соединения для лечения периодонтального заболевания |
| KR100848491B1 (ko) | 2007-01-16 | 2008-07-28 | 영진약품공업주식회사 | 베타아미노기를 갖는 2-싸이아졸리딘 유도체, 이의약학적으로 허용 가능한 염 및 이의 제조 방법 |
| JO3396B1 (ar) | 2007-06-20 | 2019-10-20 | Anacor Pharmaceuticals Inc | جزيئات صغيرة تحتوي على البورون |
| KR100895300B1 (ko) | 2007-07-20 | 2009-05-07 | 한국전자통신연구원 | 생체신호 측정의복과 생체신호 처리시스템 |
| WO2009111676A2 (en) | 2008-03-06 | 2009-09-11 | Anacor Pharmaceuticals, Inc | Boron-containing small molecules as anti-inflammatory agents |
| KR101672511B1 (ko) | 2008-03-06 | 2016-11-03 | 아나코르 파마슈티칼스 인코포레이티드 | 소염제로써 붕소가 함유된 소분자 |
| WO2009140309A2 (en) | 2008-05-12 | 2009-11-19 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| US8461336B2 (en) | 2008-09-04 | 2013-06-11 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| EP2348863A4 (en) | 2008-09-04 | 2012-03-07 | Anacor Pharmaceuticals Inc | BORN SMALL MOLECULES |
| WO2010045505A1 (en) | 2008-10-15 | 2010-04-22 | Anacor Pharmaceuticals, Inc | Boron-containing small molecules as anti-protozoal agents |
| US9493489B2 (en) | 2008-10-15 | 2016-11-15 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules as anti-protozoal agents |
| KR20110111407A (ko) | 2008-12-17 | 2011-10-11 | 아나코르 파마슈티칼스 인코포레이티드 | (ｓ)-３-아미노메틸-７-(３-히드록시-프로폭시)-３ｈ-벤조〔ｃ〕〔１,２〕옥사보롤-１-올의 다형태 |
| WO2011017125A1 (en) | 2009-07-28 | 2011-02-10 | Anacor Pharmaceuticals, Inc. | Trisubstituted boron-containing molecules |
| WO2011060196A1 (en) | 2009-11-11 | 2011-05-19 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| WO2011094450A1 (en) | 2010-01-27 | 2011-08-04 | Anacor Pharmaceuticals, Inc | Boron-containing small molecules |
| WO2011127143A1 (en) | 2010-04-07 | 2011-10-13 | Glaxosmithkline Llc | Process for preparing benzoxaboroles |
| HRP20211762T1 (hr) | 2010-09-07 | 2022-02-18 | Anacor Pharmaceuticals, Inc. | Derivati benzoksaborola za liječenje bakterijskih infekcija |
| AR088669A1 (es) | 2011-11-21 | 2014-06-25 | Lilly Co Eli | Derivados de dihidrodibenzo[c][1,2]oxaborol y dihidroisoxazol utiles para el control de ectoparasitos |
| AR088668A1 (es) | 2011-11-21 | 2014-06-25 | Lilly Co Eli | Moleculas pequeñas que contienen boro |
| JP2015212249A (ja) | 2014-05-05 | 2015-11-26 | アナコール ファーマシューティカルズ，インコーポレイテッド | 化合物および爪光沢剤 |
-
2006
- 2006-08-16 CN CN201610328000.3A patent/CN106008583A/zh active Pending
- 2006-08-16 JP JP2008548499A patent/JP2009526751A/ja active Pending
- 2006-08-16 BR BRPI0621279-4A patent/BRPI0621279B1/pt active IP Right Grant
- 2006-08-16 RU RU2008131324/04A patent/RU2008131324A/ru not_active Application Discontinuation
- 2006-08-16 CA CA002635680A patent/CA2635680A1/en not_active Abandoned
- 2006-08-16 WO PCT/US2006/032238 patent/WO2007078340A2/en not_active Ceased
- 2006-08-16 CN CN201610328016.4A patent/CN106008571A/zh active Pending
- 2006-08-16 EP EP06801794A patent/EP1976536A4/en not_active Withdrawn
- 2006-08-16 KR KR1020087018808A patent/KR20080110984A/ko not_active Withdrawn
- 2006-08-16 AU AU2006333527A patent/AU2006333527B2/en active Active
- 2006-08-16 US US11/505,591 patent/US7767657B2/en active Active
- 2006-08-16 CN CN201610327999.XA patent/CN105949230A/zh active Pending
-
2008
- 2008-06-23 IL IL192402A patent/IL192402A/en active IP Right Grant
-
2009
- 2009-12-02 US US12/629,753 patent/US8115026B2/en active Active
-
2012
- 2012-01-23 US US13/356,488 patent/US8722917B2/en active Active
- 2012-09-07 US US13/607,250 patent/US20130059802A1/en not_active Abandoned
- 2012-09-07 US US13/607,321 patent/US20130059803A1/en not_active Abandoned
- 2012-09-07 US US13/607,405 patent/US20130064783A1/en not_active Abandoned
-
2013
- 2013-04-12 US US13/861,846 patent/US20130210770A1/en not_active Abandoned
-
2014
- 2014-03-07 US US14/201,459 patent/US9353133B2/en active Active
- 2014-11-10 US US14/537,771 patent/US20150119364A1/en not_active Abandoned
-
2016
- 2016-02-17 US US15/046,322 patent/US9566289B2/en not_active Expired - Fee Related
- 2016-03-11 US US15/068,352 patent/US9549938B2/en not_active Expired - Fee Related
- 2016-04-05 US US15/091,394 patent/US9572823B2/en not_active Expired - Fee Related
- 2016-04-20 US US15/134,286 patent/US9566290B2/en not_active Expired - Fee Related
- 2016-11-18 US US15/355,393 patent/US20170066787A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160146785A (ko) * | 2014-05-05 | 2016-12-21 | 아나코르 파마슈티칼스 인코포레이티드 | 화합물 및 매니큐어 |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20080110984A (ko) | 보론함유 소분자 | |
| EP3424932B1 (en) | Boronophthalides for therapeutic use | |
| CN101505603A (zh) | 含硼的小分子 | |
| JP6109140B2 (ja) | ホウ素含有小分子 | |
| HK1228916A1 (en) | Boron-containing small molecules | |
| HK1228916A (en) | Boron-containing small molecules | |
| HK1228915A1 (zh) | 含硼的小分子 | |
| HK1228915A (en) | Boron-containing small molecules | |
| MX2008008417A (en) | Boron-containing small molecules |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20080730 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |