DK1934238T3 - TRIAZOL COMPOUNDS AND METHODS FOR THE PREPARATION AND USE OF THESE - Google Patents
TRIAZOL COMPOUNDS AND METHODS FOR THE PREPARATION AND USE OF THESE Download PDFInfo
- Publication number
- DK1934238T3 DK1934238T3 DK06802533.7T DK06802533T DK1934238T3 DK 1934238 T3 DK1934238 T3 DK 1934238T3 DK 06802533 T DK06802533 T DK 06802533T DK 1934238 T3 DK1934238 T3 DK 1934238T3
- Authority
- DK
- Denmark
- Prior art keywords
- unsaturated
- saturated
- alkyl
- aromatic
- cr116r116
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 47
- 238000002360 preparation method Methods 0.000 title description 10
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical class C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 204
- 229920006395 saturated elastomer Polymers 0.000 claims description 150
- 229910052757 nitrogen Inorganic materials 0.000 claims description 105
- 125000000304 alkynyl group Chemical group 0.000 claims description 99
- 125000003118 aryl group Chemical group 0.000 claims description 97
- 125000000217 alkyl group Chemical group 0.000 claims description 91
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 88
- 229910052760 oxygen Inorganic materials 0.000 claims description 82
- 239000001301 oxygen Substances 0.000 claims description 74
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 71
- 229910052717 sulfur Chemical group 0.000 claims description 67
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 62
- 125000005842 heteroatom Chemical group 0.000 claims description 62
- 239000011593 sulfur Chemical group 0.000 claims description 59
- -1 halogen sugars Chemical class 0.000 claims description 58
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 55
- 239000003814 drug Substances 0.000 claims description 38
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 37
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 35
- 125000004429 atom Chemical group 0.000 claims description 33
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 150000002148 esters Chemical class 0.000 claims description 25
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 201000010099 disease Diseases 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 150000001204 N-oxides Chemical class 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 150000001721 carbon Chemical group 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 235000000346 sugar Nutrition 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 5
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 5
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 5
- 150000001336 alkenes Chemical class 0.000 claims description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 4
- 238000007911 parenteral administration Methods 0.000 claims description 4
- 125000003003 spiro group Chemical group 0.000 claims description 4
- 238000011200 topical administration Methods 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- 206010017533 Fungal infection Diseases 0.000 claims description 3
- 208000031888 Mycoses Diseases 0.000 claims description 3
- 208000030852 Parasitic disease Diseases 0.000 claims description 3
- 208000036142 Viral infection Diseases 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 230000002062 proliferating effect Effects 0.000 claims description 3
- 230000009385 viral infection Effects 0.000 claims description 3
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000002016 disaccharides Chemical class 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims description 2
- 150000002337 glycosamines Chemical class 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 150000002772 monosaccharides Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000008163 sugars Chemical class 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 125000004452 carbocyclyl group Chemical group 0.000 claims 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 230000005176 gastrointestinal motility Effects 0.000 claims 1
- 102200080066 rs122460151 Human genes 0.000 claims 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 144
- 239000000203 mixture Substances 0.000 description 84
- 230000015572 biosynthetic process Effects 0.000 description 62
- 238000003786 synthesis reaction Methods 0.000 description 62
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 50
- 239000000243 solution Substances 0.000 description 48
- 241000124008 Mammalia Species 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
- 238000009472 formulation Methods 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 229940079593 drug Drugs 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- 210000001519 tissue Anatomy 0.000 description 18
- 229940041033 macrolides Drugs 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 16
- 235000011114 ammonium hydroxide Nutrition 0.000 description 16
- 239000003242 anti bacterial agent Substances 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 14
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000006352 cycloaddition reaction Methods 0.000 description 12
- 238000003818 flash chromatography Methods 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 230000001028 anti-proliverative effect Effects 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- 238000001243 protein synthesis Methods 0.000 description 11
- 230000014616 translation Effects 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000001345 alkine derivatives Chemical class 0.000 description 9
- 125000004414 alkyl thio group Chemical group 0.000 description 9
- 239000004599 antimicrobial Substances 0.000 description 9
- 229960003276 erythromycin Drugs 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 230000035772 mutation Effects 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- LJVAJPDWBABPEJ-PNUFFHFMSA-N telithromycin Chemical group O([C@@H]1[C@@H](C)C(=O)[C@@H](C)C(=O)O[C@@H]([C@]2(OC(=O)N(CCCCN3C=C(N=C3)C=3C=NC=CC=3)[C@@H]2[C@@H](C)C(=O)[C@H](C)C[C@@]1(C)OC)C)CC)[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O LJVAJPDWBABPEJ-PNUFFHFMSA-N 0.000 description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 9
- 241000894006 Bacteria Species 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 241000282414 Homo sapiens Species 0.000 description 8
- 238000003556 assay Methods 0.000 description 8
- 239000013058 crude material Substances 0.000 description 8
- 125000002950 monocyclic group Chemical group 0.000 description 8
- 150000002923 oximes Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 229960003250 telithromycin Drugs 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 230000000875 corresponding effect Effects 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
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- 229940088710 antibiotic agent Drugs 0.000 description 6
- 229960004099 azithromycin Drugs 0.000 description 6
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- 230000003115 biocidal effect Effects 0.000 description 6
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- 239000004615 ingredient Substances 0.000 description 6
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- 125000002346 iodo group Chemical group I* 0.000 description 6
- TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 210000004708 ribosome subunit Anatomy 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 5
- 239000002260 anti-inflammatory agent Substances 0.000 description 5
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- 239000003429 antifungal agent Substances 0.000 description 5
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- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 5
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- 238000001228 spectrum Methods 0.000 description 5
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- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
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- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 description 4
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- QJGDGUBLGKFNDB-UHFFFAOYSA-N 1-azido-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1N=[N+]=[N-] QJGDGUBLGKFNDB-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 3
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
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- 241000282412 Homo Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
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- 239000007864 aqueous solution Substances 0.000 description 3
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Classifications
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- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
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- A—HUMAN NECESSITIES
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
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- Tropical Medicine & Parasitology (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (3)
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| US71144305P | 2005-08-24 | 2005-08-24 | |
| US76290706P | 2006-01-26 | 2006-01-26 | |
| PCT/US2006/033645 WO2007025284A1 (en) | 2005-08-24 | 2006-08-24 | Triazole compounds and methods of making and using the same |
Publications (1)
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| DK1934238T3 true DK1934238T3 (en) | 2017-09-18 |
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| DK06802533.7T DK1934238T3 (en) | 2005-08-24 | 2006-08-24 | TRIAZOL COMPOUNDS AND METHODS FOR THE PREPARATION AND USE OF THESE |
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| EP (3) | EP3290427A1 (https=) |
| JP (6) | JP5395432B2 (https=) |
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| ES (1) | ES2638427T3 (https=) |
| HR (1) | HRP20171285T1 (https=) |
| WO (2) | WO2007025284A1 (https=) |
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| JP5383037B2 (ja) | 2004-02-27 | 2014-01-08 | リブ−エックス ファーマシューティカルズ，インコーポレイテッド | 大環状化合物およびそれらを製造し使用する方法 |
| JP2009506063A (ja) | 2005-08-24 | 2009-02-12 | リブ−エックス ファーマシューティカルズ，インコーポレイテッド | トリアゾール化合物ならびにこれを作製する方法および使用する方法 |
| EP3290427A1 (en) * | 2005-08-24 | 2018-03-07 | Melinta Therapeutics, Inc. | Triazole compounds and methods of making and using the same |
| WO2008106224A1 (en) * | 2007-02-28 | 2008-09-04 | Rib-X Pharmaceuticals, Inc. | Macrolide compounds and methods of making and using the same |
| EP2176216B1 (en) * | 2007-07-06 | 2012-04-25 | Paratek Pharmaceuticals, Inc. | Methods for synthesizing 9-substituted minocycline |
| JP2011026260A (ja) * | 2009-07-28 | 2011-02-10 | Central Glass Co Ltd | ３位に脱離基を有する２−フルオロプロピルアミン保護体または該アミンｎ−アルキル保護体 |
| CN101619085B (zh) * | 2009-08-11 | 2015-04-22 | 沈阳药科大学 | 红霉素衍生物及其作为肿瘤细胞增殖抑制剂的用途 |
| AR092278A1 (es) * | 2012-08-31 | 2015-04-08 | Novartis Ag | Proceso de obtencion de derivados n-acilicos de bifenil-alanina e intermediarios relacionados |
| HK1244211A1 (zh) | 2014-11-14 | 2018-08-03 | Melinta Therapeutics, Inc. | 治疗、预防或降低皮肤感染风险的方法 |
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| CN110108826A (zh) * | 2019-05-24 | 2019-08-09 | 内蒙古蒙牛乳业（集团）股份有限公司 | 乳或乳制品中氟苯尼考胺的检测方法 |
| US20210371389A1 (en) * | 2020-04-24 | 2021-12-02 | Kansas Soybean Commission | One-step synthesis of soybean polyols |
| WO2022146980A1 (en) | 2020-12-28 | 2022-07-07 | Georgia Tech Research Corporation | Compositions and methods for inhibiting fibrosis, inflammation and cancer |
| CN115745823B (zh) * | 2022-11-03 | 2024-02-23 | 武夷学院 | 一种化合物的制备方法及其应用 |
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| US3725385A (en) | 1970-11-02 | 1973-04-03 | Abbott Lab | Process for the demethylation of 3-amino macrolides |
| US4522811A (en) | 1982-07-08 | 1985-06-11 | Syntex (U.S.A.) Inc. | Serial injection of muramyldipeptides and liposomes enhances the anti-infective activity of muramyldipeptides |
| MY113693A (en) | 1992-05-26 | 2002-05-31 | Chugai Pharmaceutical Co Ltd | Erythromycin derivatives having an enterokinesis stimulating action |
| US6927057B2 (en) | 1993-09-20 | 2005-08-09 | Kosan Biosciences | Macrolide analogs |
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| DK1025114T3 (da) * | 1997-09-30 | 2004-07-05 | Abbott Lab | 3'-N-modificerede 6-O-substituerede erythromycin-ketolidderivater med antibakteriel aktivitet |
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| ZA989885B (en) | 1997-10-31 | 1999-05-05 | Abbott Lab | Use of macrolides for the treatment of cancer and macular degeneration |
| WO1999063929A2 (en) | 1998-06-08 | 1999-12-16 | Advanced Medicine, Inc. | Multibinding inhibitors of microsomal triglyceride transferase protein |
| IT1301968B1 (it) | 1998-07-30 | 2000-07-20 | Zambon Spa | Derivati di eritromicina ad attivita' antibiotica |
| GB9821938D0 (en) | 1998-10-09 | 1998-12-02 | Zeneca Ltd | Chemical compounds |
| HRP980646B1 (en) | 1998-12-30 | 2008-02-29 | GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o. | Novel oleandomycin derivatives |
| US6514944B2 (en) | 1999-04-16 | 2003-02-04 | Kosan Biosciences, Inc. | Macrolide antiinfective agents |
| US6939861B2 (en) | 1999-04-16 | 2005-09-06 | Kosan Biosciences, Inc. | Amido macrolides |
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| EP1101769A3 (en) | 1999-11-18 | 2001-10-24 | Pfizer Products Inc. | Nitrogen containing erythromycin derivatives |
| GB9928568D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
| JP2003522763A (ja) | 2000-02-10 | 2003-07-29 | ファルマシア・アンド・アップジョン・カンパニー | ピペラジンアミド置換基を持つオキサゾリジノンチオアミド |
| CA2399198A1 (en) | 2000-02-18 | 2001-08-23 | Christopher Carreras | Motilide compounds |
| GB0009803D0 (en) | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| ATE321770T1 (de) | 2000-08-17 | 2006-04-15 | Kitasato Inst | Pseudoerythromycin-derivate |
| BR0113472A (pt) | 2000-08-22 | 2003-07-01 | Basilea Pharmaceutica Ag | Macrolìdeos com atividade antibacteriana |
| AU2002225724A1 (en) | 2000-12-01 | 2002-07-08 | Kosan Biosciences, Inc. | Motilide compounds |
| WO2003004509A2 (en) | 2001-07-03 | 2003-01-16 | Chiron Corporation | C12 modified erythromycin macrolides and ketolides having antibacterial activity |
| US7396847B2 (en) | 2001-09-11 | 2008-07-08 | Astrazeneca Ab | Oxazolidinone and/or isoxazoline as antibacterial agents |
| EP1443930A1 (en) | 2001-10-25 | 2004-08-11 | AstraZeneca AB | Isoxazoline derivatives useful as antimicrobials |
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-
2006
- 2006-08-24 EP EP17178221.2A patent/EP3290427A1/en not_active Withdrawn
- 2006-08-24 EP EP06824847A patent/EP1928893A2/en not_active Withdrawn
- 2006-08-24 HR HRP20171285TT patent/HRP20171285T1/hr unknown
- 2006-08-24 DK DK06802533.7T patent/DK1934238T3/en active
- 2006-08-24 WO PCT/US2006/033645 patent/WO2007025284A1/en not_active Ceased
- 2006-08-24 JP JP2008528247A patent/JP5395432B2/ja not_active Expired - Fee Related
- 2006-08-24 ES ES06802533T patent/ES2638427T3/es active Active
- 2006-08-24 JP JP2008528168A patent/JP2009506066A/ja not_active Withdrawn
- 2006-08-24 EP EP06802533.7A patent/EP1934238B1/en not_active Not-in-force
- 2006-08-24 US US11/990,883 patent/US8278281B2/en not_active Expired - Fee Related
- 2006-08-24 WO PCT/US2006/033170 patent/WO2007025098A2/en not_active Ceased
-
2012
- 2012-09-14 US US13/616,962 patent/US20130065845A1/en not_active Abandoned
-
2013
- 2013-08-19 JP JP2013169594A patent/JP5981401B2/ja not_active Expired - Fee Related
- 2013-08-21 US US13/972,732 patent/US9006189B2/en not_active Expired - Fee Related
-
2015
- 2015-03-18 US US14/661,863 patent/US20160031926A1/en not_active Abandoned
- 2015-11-16 JP JP2015223733A patent/JP2016094421A/ja active Pending
-
2017
- 2017-05-17 US US15/597,701 patent/US20180094016A1/en not_active Abandoned
- 2017-07-21 JP JP2017141745A patent/JP2018008970A/ja active Pending
-
2018
- 2018-09-11 JP JP2018169395A patent/JP2019023194A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP5981401B2 (ja) | 2016-08-31 |
| US20100016956A1 (en) | 2010-01-21 |
| WO2007025098A2 (en) | 2007-03-01 |
| JP2019023194A (ja) | 2019-02-14 |
| WO2007025098A3 (en) | 2007-04-26 |
| US20130065845A1 (en) | 2013-03-14 |
| JP5395432B2 (ja) | 2014-01-22 |
| US20160031926A1 (en) | 2016-02-04 |
| US9006189B2 (en) | 2015-04-14 |
| EP1934238A1 (en) | 2008-06-25 |
| JP2009506075A (ja) | 2009-02-12 |
| EP3290427A1 (en) | 2018-03-07 |
| US20180094016A1 (en) | 2018-04-05 |
| US8278281B2 (en) | 2012-10-02 |
| ES2638427T3 (es) | 2017-10-20 |
| EP1928893A2 (en) | 2008-06-11 |
| WO2007025284A1 (en) | 2007-03-01 |
| JP2016094421A (ja) | 2016-05-26 |
| EP1934238B1 (en) | 2017-06-28 |
| HRP20171285T1 (hr) | 2017-10-20 |
| JP2013256517A (ja) | 2013-12-26 |
| JP2018008970A (ja) | 2018-01-18 |
| US20140088031A1 (en) | 2014-03-27 |
| WO2007025284A8 (en) | 2007-04-26 |
| JP2009506066A (ja) | 2009-02-12 |
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