EA037587B1 - Способ получения противогрибковых соединений - Google Patents
Способ получения противогрибковых соединений Download PDFInfo
- Publication number
- EA037587B1 EA037587B1 EA201691649A EA201691649A EA037587B1 EA 037587 B1 EA037587 B1 EA 037587B1 EA 201691649 A EA201691649 A EA 201691649A EA 201691649 A EA201691649 A EA 201691649A EA 037587 B1 EA037587 B1 EA 037587B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- compound
- mixture
- halogen
- amino alcohol
- mixtures
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 title claims description 144
- 229940121375 antifungal agent Drugs 0.000 title abstract description 6
- 230000000843 anti-fungal effect Effects 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 130
- 229940125904 compound 1 Drugs 0.000 claims abstract description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 62
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 45
- 229910052736 halogen Inorganic materials 0.000 claims description 41
- 150000002367 halogens Chemical group 0.000 claims description 41
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 39
- 150000001414 amino alcohols Chemical class 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 34
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 30
- -1 4- (2,2,2-trifluoroethoxy) phenyl Chemical group 0.000 claims description 26
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 25
- 230000003993 interaction Effects 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 24
- 230000015572 biosynthetic process Effects 0.000 claims description 22
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 claims description 20
- 150000002576 ketones Chemical class 0.000 claims description 19
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 16
- ZKWFSTHEYLJLEL-UHFFFAOYSA-N morpholine-4-carboxamide Chemical compound NC(=O)N1CCOCC1 ZKWFSTHEYLJLEL-UHFFFAOYSA-N 0.000 claims description 16
- 238000002425 crystallisation Methods 0.000 claims description 14
- 230000008025 crystallization Effects 0.000 claims description 14
- 150000003536 tetrazoles Chemical class 0.000 claims description 12
- FMASTXATFLPSON-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-[4-(2,2,2-trifluoroethoxy)phenyl]-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(OCC(F)(F)F)C=C1 FMASTXATFLPSON-UHFFFAOYSA-N 0.000 claims description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- 229910021529 ammonia Inorganic materials 0.000 claims description 10
- 239000006184 cosolvent Substances 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical group OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 8
- 238000006254 arylation reaction Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 238000010790 dilution Methods 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
- 229940011051 isopropyl acetate Drugs 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims 6
- 150000001412 amines Chemical class 0.000 claims 1
- ZVQXQPNJHRNGID-UHFFFAOYSA-N tetramethylsuccinonitrile Chemical compound N#CC(C)(C)C(C)(C)C#N ZVQXQPNJHRNGID-UHFFFAOYSA-N 0.000 claims 1
- 239000003429 antifungal agent Substances 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 85
- 239000011541 reaction mixture Substances 0.000 description 79
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 39
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 28
- 239000012044 organic layer Substances 0.000 description 28
- 238000004128 high performance liquid chromatography Methods 0.000 description 25
- 239000007787 solid Substances 0.000 description 25
- 102000004190 Enzymes Human genes 0.000 description 24
- 108090000790 Enzymes Proteins 0.000 description 24
- 239000010410 layer Substances 0.000 description 24
- 201000010099 disease Diseases 0.000 description 23
- 239000000651 prodrug Substances 0.000 description 22
- 229940002612 prodrug Drugs 0.000 description 22
- 235000019439 ethyl acetate Nutrition 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 18
- 239000000725 suspension Substances 0.000 description 18
- 230000000694 effects Effects 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 235000019441 ethanol Nutrition 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
- 238000011282 treatment Methods 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 15
- 239000008194 pharmaceutical composition Substances 0.000 description 15
- 239000000523 sample Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 208000035475 disorder Diseases 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 230000002829 reductive effect Effects 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000011780 sodium chloride Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 11
- 239000003814 drug Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 230000008901 benefit Effects 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 150000002924 oxiranes Chemical class 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 239000003937 drug carrier Substances 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
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- 230000005764 inhibitory process Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 230000001225 therapeutic effect Effects 0.000 description 8
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 8
- 125000000304 alkynyl group Chemical group 0.000 description 7
- 229910052786 argon Inorganic materials 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
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- 230000000069 prophylactic effect Effects 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 125000005907 alkyl ester group Chemical group 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 235000011181 potassium carbonates Nutrition 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 229940124597 therapeutic agent Drugs 0.000 description 6
- MGHBDQZXPCTTIH-UHFFFAOYSA-N 1-bromo-2,4-difluorobenzene Chemical compound FC1=CC=C(Br)C(F)=C1 MGHBDQZXPCTTIH-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- 125000002619 bicyclic group Chemical group 0.000 description 5
- 239000007853 buffer solution Substances 0.000 description 5
- 238000004296 chiral HPLC Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000007818 Grignard reagent Substances 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 230000005587 bubbling Effects 0.000 description 4
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- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 210000003169 central nervous system Anatomy 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
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- 125000000524 functional group Chemical group 0.000 description 4
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- 150000004795 grignard reagents Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
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- 238000005406 washing Methods 0.000 description 4
- IDUYJRXRDSPPRC-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(OCC(F)(F)F)=CC=1)(O)CN1C=NN=N1 IDUYJRXRDSPPRC-UHFFFAOYSA-N 0.000 description 3
- FAUXJAGOYAFCKE-UHFFFAOYSA-N 5-bromo-2-[[2-(2,4-difluorophenyl)oxiran-2-yl]-difluoromethyl]pyridine Chemical compound FC1=CC(F)=CC=C1C1(C(F)(F)C=2N=CC(Br)=CC=2)OC1 FAUXJAGOYAFCKE-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
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- CCNNVRZLXOPTID-UHFFFAOYSA-N ethyl 2-(5-bromopyridin-2-yl)-2,2-difluoroacetate Chemical compound CCOC(=O)C(F)(F)C1=CC=C(Br)C=N1 CCNNVRZLXOPTID-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 238000011200 topical administration Methods 0.000 description 3
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- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 description 3
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- 239000011701 zinc Substances 0.000 description 3
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- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 235000008476 powdered milk Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical class CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- OPAHEYNNJWPQPX-RCDICMHDSA-N ravuconazole Chemical compound C=1SC([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=1C1=CC=C(C#N)C=C1 OPAHEYNNJWPQPX-RCDICMHDSA-N 0.000 description 1
- 229950004154 ravuconazole Drugs 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- VEMKTZHHVJILDY-UHFFFAOYSA-N resmethrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UHFFFAOYSA-N 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000004963 sulfonylalkyl group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001395 thiirenyl group Chemical group 0.000 description 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Artificial Filaments (AREA)
Applications Claiming Priority (2)
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|---|---|---|---|
| US201461955615P | 2014-03-19 | 2014-03-19 | |
| PCT/US2015/021491 WO2015143172A1 (en) | 2014-03-19 | 2015-03-19 | Antifungal compound process |
Publications (2)
| Publication Number | Publication Date |
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| EA201691649A1 EA201691649A1 (ru) | 2016-12-30 |
| EA037587B1 true EA037587B1 (ru) | 2021-04-19 |
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| EA201691649A EA037587B1 (ru) | 2014-03-19 | 2015-03-19 | Способ получения противогрибковых соединений |
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| US (2) | US10173998B2 (enExample) |
| EP (1) | EP3119745B1 (enExample) |
| JP (1) | JP6509897B2 (enExample) |
| KR (1) | KR102151082B1 (enExample) |
| CN (2) | CN106458900B (enExample) |
| AU (1) | AU2015231226B2 (enExample) |
| BR (1) | BR112016020937B1 (enExample) |
| CA (1) | CA2942968C (enExample) |
| EA (1) | EA037587B1 (enExample) |
| ES (1) | ES2815373T3 (enExample) |
| HU (1) | HUE052446T2 (enExample) |
| MX (1) | MX365494B (enExample) |
| PL (1) | PL3119745T3 (enExample) |
| WO (1) | WO2015143172A1 (enExample) |
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| JP6572234B2 (ja) * | 2014-03-19 | 2019-09-04 | ヴィアメット ファーマスーティカルズ（エヌシー），インコーポレイテッド | 抗真菌化合物の調製方法 |
| AU2015231275B2 (en) | 2014-03-19 | 2019-03-07 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| KR102441243B1 (ko) | 2014-03-19 | 2022-09-07 | 브이피에스-3, 엘엘씨 | 2-(2,4-디플루오르페닐)-1,1-디플루오르-1-(5-치환된-피리딘-2-일)-3-(1h-테트라졸-1-일)프로판-2-올 및 이의 제조방법 |
| AU2015231208B2 (en) * | 2014-03-19 | 2019-04-04 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| CA2942936A1 (en) | 2014-03-19 | 2015-09-24 | Viamet Pharmaceuticals, Inc. | Antifungal compound process |
| EP3119753B1 (en) | 2014-03-19 | 2020-11-04 | Dow AgroSciences LLC | 2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-substituted-pyridin-2-yl)-3-(1h-tetrazol-1-yl)propan-2-ols and processes for their preparation |
| WO2015143180A1 (en) | 2014-03-19 | 2015-09-24 | Viamet Pharmaceuticals, Inc. | Antifungal compound process |
| CA2942231A1 (en) | 2014-03-19 | 2015-09-24 | Viamet Pharmaceuticals, Inc. | Antifungal compound process |
| DK3271347T3 (da) * | 2015-03-19 | 2022-07-18 | Mycovia Pharmaceuticals Inc | Antifungale forbindelser og fremstillingsfremgangsmåder |
| HK1263287A1 (zh) * | 2015-09-18 | 2020-03-20 | Nqp 1598, Ltd. | 抗真菌化合物和制备方法 |
| US11213031B2 (en) | 2017-11-13 | 2022-01-04 | Bayer Aktiengesellschaft | Tetrazolylpropyl derivatives and their use as fungicides |
| AU2019325436B2 (en) * | 2018-08-18 | 2023-10-26 | 5Metis, Inc. | Solid forms of substituted benzoxaborole and compositions thereof |
| CN114573557B (zh) * | 2022-03-28 | 2024-03-08 | 浙江天宇药业股份有限公司 | 一种奥特康唑的制备方法 |
| CN116621816B (zh) * | 2022-09-23 | 2025-07-04 | 北京莱瑞森医药科技有限公司 | 一种伏立康唑对映异构对b的拆分方法 |
| CN116675672B (zh) * | 2023-06-05 | 2025-04-25 | 北京康立生医药技术开发有限公司 | 一种抗真菌药物的制备方法 |
| CN119798219B (zh) * | 2025-01-13 | 2025-07-18 | 长治医学院 | 一种奥特康唑的制备方法 |
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| WO2011133875A2 (en) * | 2010-04-24 | 2011-10-27 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| WO2013109998A1 (en) * | 2012-01-20 | 2013-07-25 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| WO2013110002A1 (en) * | 2012-01-20 | 2013-07-25 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
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| DE2854015B2 (de) | 1978-12-14 | 1980-10-09 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von !H-TetrazoI-1-essigsauren und bestimmter Ester derselben |
| JP2000344744A (ja) | 1999-06-04 | 2000-12-12 | Ss Pharmaceut Co Ltd | アセトフェノン誘導体およびその製法 |
| US8198448B2 (en) | 2006-07-14 | 2012-06-12 | Amgen Inc. | Fused heterocyclic derivatives and methods of use |
| KR100889937B1 (ko) | 2007-08-06 | 2009-03-20 | 한미약품 주식회사 | 보리코나졸의 제조방법 |
| KR101109215B1 (ko) | 2009-06-17 | 2012-01-30 | 보령제약 주식회사 | 보리코나졸의 신규 중간체 및 이를 이용한 보리코나졸의 제조방법 |
| CN102803232A (zh) | 2009-06-18 | 2012-11-28 | 巴斯夫欧洲公司 | 杀真菌的具有5-硫取代基的1,2,4-三唑衍生物 |
| BR122020013521B1 (pt) | 2011-06-19 | 2021-05-25 | Viamet Pharmaceuticals (NC), Inc | compostos inibidores de metaloenzima |
| EP2721021B1 (en) * | 2011-06-19 | 2019-01-23 | Viamet Pharmaceuticals (NC), Inc. | Metalloenzyme inhibitor compounds |
| CN103930418A (zh) | 2011-06-23 | 2014-07-16 | 威尔金制药有限公司 | 金属酶抑制剂化合物 |
| BR112014013963B1 (pt) * | 2011-12-11 | 2021-06-22 | Nqp 1598, Ltd | Compostos inibidores de metaloenzimas, composições compreendendo os ditos compostos, uso terapêutico dos mesmos e métodos para inibir a atividade de metaloenzimas e para tratar ou prevenir o crescimento de fungos em plantas |
| WO2014043376A1 (en) | 2012-09-12 | 2014-03-20 | Dow Agrosciences Llc | Metalloenzyme inhibitor compounds |
| WO2014117090A1 (en) | 2013-01-28 | 2014-07-31 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
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| CA2942936A1 (en) | 2014-03-19 | 2015-09-24 | Viamet Pharmaceuticals, Inc. | Antifungal compound process |
| JP6572234B2 (ja) | 2014-03-19 | 2019-09-04 | ヴィアメット ファーマスーティカルズ（エヌシー），インコーポレイテッド | 抗真菌化合物の調製方法 |
| WO2015143180A1 (en) | 2014-03-19 | 2015-09-24 | Viamet Pharmaceuticals, Inc. | Antifungal compound process |
| AU2015231275B2 (en) | 2014-03-19 | 2019-03-07 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| CA2942231A1 (en) | 2014-03-19 | 2015-09-24 | Viamet Pharmaceuticals, Inc. | Antifungal compound process |
| KR102441243B1 (ko) | 2014-03-19 | 2022-09-07 | 브이피에스-3, 엘엘씨 | 2-(2,4-디플루오르페닐)-1,1-디플루오르-1-(5-치환된-피리딘-2-일)-3-(1h-테트라졸-1-일)프로판-2-올 및 이의 제조방법 |
| AU2015231208B2 (en) | 2014-03-19 | 2019-04-04 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| US9802914B2 (en) | 2014-03-19 | 2017-10-31 | Viamet Pharmaceuticals, Inc. | Antifungal compound process |
| EP3119753B1 (en) | 2014-03-19 | 2020-11-04 | Dow AgroSciences LLC | 2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-substituted-pyridin-2-yl)-3-(1h-tetrazol-1-yl)propan-2-ols and processes for their preparation |
| DK3271347T3 (da) | 2015-03-19 | 2022-07-18 | Mycovia Pharmaceuticals Inc | Antifungale forbindelser og fremstillingsfremgangsmåder |
| KR20180000731A (ko) | 2015-05-18 | 2018-01-03 | 비아멧 파마슈티컬즈, 인코포레이티드 | 항진균성 화합물 |
| HK1263287A1 (zh) | 2015-09-18 | 2020-03-20 | Nqp 1598, Ltd. | 抗真菌化合物和制备方法 |
| CA3005743A1 (en) | 2015-11-17 | 2017-05-26 | Dow Agrosciences Llc | 4-((6-(2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1h-1,2,4-triazol-1-yl)propyl)pyridin-3-yl)oxy)benzonitrile and processes of preparation |
| JP6963557B2 (ja) | 2015-11-17 | 2021-11-10 | コルテバ アグリサイエンス エルエルシー | ４−（（６−（２−（２，４−ジフルオロフェニル）−１，１−ジフルオロ−２−ヒドロキシ−３−（１ｈ−１，２，４−トリアゾール−１−イル）プロピル）ピリジン−３−イル）オキシ）ベンゾニトリル及び調製方法 |
| KR20180101343A (ko) | 2015-11-17 | 2018-09-12 | 다우 아그로사이언시즈 엘엘씨 | 4-((6-(2-(2,4-디플루오로페닐)-1,1-디플루오로-2-옥소에틸)피리딘-3-일)옥시)벤조니트릴 및 제조방법 |
| EP3377475A4 (en) | 2015-11-17 | 2019-04-10 | Dow Agrosciences Llc | 4 - ((6-2- (2,4-difluorophenyl) -1,1-difluoro-2-hydroxy-3- (1H-1,2,4-triazol-1-YL) PROPYL) PYRIDINE-3-YL ) OXY) BENZONITRIL AND METHOD OF PREPARING THEREOF |
| EA038421B1 (ru) | 2015-12-30 | 2021-08-26 | ВиПиЭс-3, ИНК. | Соединения, ингибирующие металлоферменты |
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2015
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- 2015-03-19 CN CN201580014076.2A patent/CN106458900B/zh active Active
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- 2015-03-19 JP JP2016557968A patent/JP6509897B2/ja active Active
- 2015-03-19 HU HUE15764743A patent/HUE052446T2/hu unknown
- 2015-03-19 PL PL15764743T patent/PL3119745T3/pl unknown
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- 2015-03-19 MX MX2016012056A patent/MX365494B/es active IP Right Grant
- 2015-03-19 EA EA201691649A patent/EA037587B1/ru unknown
- 2015-03-19 AU AU2015231226A patent/AU2015231226B2/en not_active Ceased
- 2015-03-19 ES ES15764743T patent/ES2815373T3/es active Active
- 2015-03-19 CN CN201811509148.2A patent/CN109970629B/zh active Active
- 2015-03-19 KR KR1020167025607A patent/KR102151082B1/ko active Active
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2019
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Patent Citations (3)
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| WO2011133875A2 (en) * | 2010-04-24 | 2011-10-27 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| WO2013109998A1 (en) * | 2012-01-20 | 2013-07-25 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| WO2013110002A1 (en) * | 2012-01-20 | 2013-07-25 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
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|---|---|
| EP3119745A1 (en) | 2017-01-25 |
| MX2016012056A (es) | 2017-04-27 |
| HUE052446T2 (hu) | 2021-04-28 |
| JP6509897B2 (ja) | 2019-05-08 |
| WO2015143172A1 (en) | 2015-09-24 |
| CN106458900A (zh) | 2017-02-22 |
| US10392365B2 (en) | 2019-08-27 |
| CA2942968A1 (en) | 2015-09-24 |
| EP3119745A4 (en) | 2017-08-23 |
| BR112016020937B1 (pt) | 2022-09-20 |
| AU2015231226A1 (en) | 2016-10-06 |
| AU2015231226B2 (en) | 2019-04-04 |
| PL3119745T3 (pl) | 2021-01-25 |
| BR112016020937A2 (enExample) | 2017-08-15 |
| EA201691649A1 (ru) | 2016-12-30 |
| US20170088539A1 (en) | 2017-03-30 |
| US10173998B2 (en) | 2019-01-08 |
| MX365494B (es) | 2019-06-05 |
| US20190161469A1 (en) | 2019-05-30 |
| JP2017509644A (ja) | 2017-04-06 |
| CN106458900B (zh) | 2019-01-01 |
| KR102151082B1 (ko) | 2020-09-03 |
| CA2942968C (en) | 2022-03-15 |
| KR20160138012A (ko) | 2016-12-02 |
| ES2815373T3 (es) | 2021-03-29 |
| EP3119745B1 (en) | 2020-08-05 |
| CN109970629A (zh) | 2019-07-05 |
| CN109970629B (zh) | 2023-04-11 |
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