JP2015504095A5 - - Google Patents
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- Publication number
- JP2015504095A5 JP2015504095A5 JP2014553491A JP2014553491A JP2015504095A5 JP 2015504095 A5 JP2015504095 A5 JP 2015504095A5 JP 2014553491 A JP2014553491 A JP 2014553491A JP 2014553491 A JP2014553491 A JP 2014553491A JP 2015504095 A5 JP2015504095 A5 JP 2015504095A5
- Authority
- JP
- Japan
- Prior art keywords
- disease
- tetrazol
- difluorophenyl
- alkyl
- pyridin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 36
- 125000000217 alkyl group Chemical group 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 22
- 201000010099 disease Diseases 0.000 claims 20
- 238000000034 method Methods 0.000 claims 19
- 125000001188 haloalkyl group Chemical group 0.000 claims 14
- 208000035475 disorder Diseases 0.000 claims 13
- 125000005843 halogen group Chemical group 0.000 claims 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- 210000003169 central nervous system Anatomy 0.000 claims 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- 239000003795 chemical substances by application Substances 0.000 claims 7
- -1 1H-tetrazol-1-yl Chemical group 0.000 claims 6
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 5
- 241000222122 Candida albicans Species 0.000 claims 4
- 201000007336 Cryptococcosis Diseases 0.000 claims 4
- 241000221204 Cryptococcus neoformans Species 0.000 claims 4
- 206010017533 Fungal infection Diseases 0.000 claims 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims 4
- 241000223230 Trichosporon Species 0.000 claims 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 208000030159 metabolic disease Diseases 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims 4
- 229940124597 therapeutic agent Drugs 0.000 claims 4
- 125000004001 thioalkyl group Chemical group 0.000 claims 4
- 125000001425 triazolyl group Chemical group 0.000 claims 4
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 3
- 229940127089 cytotoxic agent Drugs 0.000 claims 3
- 208000010643 digestive system disease Diseases 0.000 claims 3
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 3
- 208000015181 infectious disease Diseases 0.000 claims 3
- 201000000317 pneumocystosis Diseases 0.000 claims 3
- 208000014001 urinary system disease Diseases 0.000 claims 3
- IEYCWUALSWPHDI-UHFFFAOYSA-N 1-[4-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]phenyl]-2,2,2-trifluoroethanone Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(=CC=1)C(=O)C(F)(F)F)(O)CN1C=NN=N1 IEYCWUALSWPHDI-UHFFFAOYSA-N 0.000 claims 2
- QFSIEMVDJIQESH-UHFFFAOYSA-N 1-[5-(4-chloro-3-fluorophenyl)pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-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=C(F)C(Cl)=CC=1)(O)CN1C=NN=N1 QFSIEMVDJIQESH-UHFFFAOYSA-N 0.000 claims 2
- LTGBNLMVVAFZGT-UHFFFAOYSA-N 1-[5-[4-(difluoromethoxy)phenyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-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(OC(F)F)=CC=1)(O)CN1C=NN=N1 LTGBNLMVVAFZGT-UHFFFAOYSA-N 0.000 claims 2
- GSIBKGBPHNSCOU-UHFFFAOYSA-N 1-[5-[4-(difluoromethylsulfanyl)phenyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-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(SC(F)F)=CC=1)(O)CN1C=NN=N1 GSIBKGBPHNSCOU-UHFFFAOYSA-N 0.000 claims 2
- BLPPSIFFRCQAID-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-phenylpyridin-2-yl)-3-(tetrazol-1-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=CC=1)(O)CN1C=NN=N1 BLPPSIFFRCQAID-UHFFFAOYSA-N 0.000 claims 2
- YQTJCWNNHNJRAY-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[4-[(2-methylpropan-2-yl)oxy]phenyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(OC(C)(C)C)=CC=C1C1=CC=C(C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)N=C1 YQTJCWNNHNJRAY-UHFFFAOYSA-N 0.000 claims 2
- CAXYCUMJWGYZCQ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[3-(trifluoromethyl)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=C(C=CC=1)C(F)(F)F)(O)CN1C=NN=N1 CAXYCUMJWGYZCQ-UHFFFAOYSA-N 0.000 claims 2
- NGSZMSSFJMJEPD-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethyl)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(CC(F)(F)F)=CC=1)(O)CN1C=NN=N1 NGSZMSSFJMJEPD-UHFFFAOYSA-N 0.000 claims 2
- IBQKNYMGTNJJGD-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethylsulfanyl)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(SCC(F)(F)F)=CC=1)(O)CN1C=NN=N1 IBQKNYMGTNJJGD-UHFFFAOYSA-N 0.000 claims 2
- JBDKQTLQCWIBHU-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(3,3,3-trifluoropropoxy)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(OCCC(F)(F)F)=CC=1)(O)CN1C=NN=N1 JBDKQTLQCWIBHU-UHFFFAOYSA-N 0.000 claims 2
- QBUDANSQCYSGLX-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(Cl)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(OC(F)(F)F)=CC=1)(O)CN1C=NN=N1 QBUDANSQCYSGLX-UHFFFAOYSA-N 0.000 claims 2
- PDUNABKLLIZVMV-UHFFFAOYSA-N 3-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]phenol Chemical compound OC1=CC=CC(C=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)=C1 PDUNABKLLIZVMV-UHFFFAOYSA-N 0.000 claims 2
- 201000002909 Aspergillosis Diseases 0.000 claims 2
- 208000036641 Aspergillus infections Diseases 0.000 claims 2
- 241000228245 Aspergillus niger Species 0.000 claims 2
- 206010007134 Candida infections Diseases 0.000 claims 2
- 241000222178 Candida tropicalis Species 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 241000223203 Coccidioides Species 0.000 claims 2
- 241000223205 Coccidioides immitis Species 0.000 claims 2
- 208000035473 Communicable disease Diseases 0.000 claims 2
- 241001634927 Cutaneotrichosporon mucoides Species 0.000 claims 2
- 206010012504 Dermatophytosis Diseases 0.000 claims 2
- 241000427940 Fusarium solani Species 0.000 claims 2
- 244000286779 Hansenula anomala Species 0.000 claims 2
- 235000014683 Hansenula anomala Nutrition 0.000 claims 2
- 241000228402 Histoplasma Species 0.000 claims 2
- 201000002563 Histoplasmosis Diseases 0.000 claims 2
- 241000893980 Microsporum canis Species 0.000 claims 2
- 241001460074 Microsporum distortum Species 0.000 claims 2
- 208000031888 Mycoses Diseases 0.000 claims 2
- 241000893974 Nannizzia fulva Species 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000010195 Onychomycosis Diseases 0.000 claims 2
- 206010033767 Paracoccidioides infections Diseases 0.000 claims 2
- 201000000301 Paracoccidioidomycosis Diseases 0.000 claims 2
- 241000228143 Penicillium Species 0.000 claims 2
- 241000235648 Pichia Species 0.000 claims 2
- 208000005384 Pneumocystis Pneumonia Diseases 0.000 claims 2
- 206010073755 Pneumocystis jirovecii pneumonia Diseases 0.000 claims 2
- 208000004364 Rhinosporidiosis Diseases 0.000 claims 2
- 241000223254 Rhodotorula mucilaginosa Species 0.000 claims 2
- 208000002474 Tinea Diseases 0.000 claims 2
- 206010056131 Tinea versicolour Diseases 0.000 claims 2
- 241000223238 Trichophyton Species 0.000 claims 2
- 241001045770 Trichophyton mentagrophytes Species 0.000 claims 2
- 241000223229 Trichophyton rubrum Species 0.000 claims 2
- 241001480050 Trichophyton violaceum Species 0.000 claims 2
- 241001634942 Trichosporon inkin Species 0.000 claims 2
- 208000012931 Urologic disease Diseases 0.000 claims 2
- 206010061418 Zygomycosis Diseases 0.000 claims 2
- 241000222126 [Candida] glabrata Species 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 2
- 230000001028 anti-proliverative effect Effects 0.000 claims 2
- 239000003429 antifungal agent Substances 0.000 claims 2
- 229940121375 antifungal agent Drugs 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 229940095731 candida albicans Drugs 0.000 claims 2
- 208000032343 candida glabrata infection Diseases 0.000 claims 2
- 201000003984 candidiasis Diseases 0.000 claims 2
- 239000002327 cardiovascular agent Substances 0.000 claims 2
- 229940125692 cardiovascular agent Drugs 0.000 claims 2
- 201000003486 coccidioidomycosis Diseases 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 239000002254 cytotoxic agent Substances 0.000 claims 2
- 231100000599 cytotoxic agent Toxicity 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 208000030172 endocrine system disease Diseases 0.000 claims 2
- HZLNQXPXQPWTKY-UHFFFAOYSA-N ethyl 2-[4-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]phenoxy]-2,2-difluoroacetate Chemical compound C1=CC(OC(F)(F)C(=O)OCC)=CC=C1C1=CC=C(C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)N=C1 HZLNQXPXQPWTKY-UHFFFAOYSA-N 0.000 claims 2
- 208000024386 fungal infectious disease Diseases 0.000 claims 2
- 244000053095 fungal pathogen Species 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 201000007524 mucormycosis Diseases 0.000 claims 2
- ZLJNVYHHBJHWCQ-UHFFFAOYSA-N n-[4-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]phenyl]-2,2,2-trifluoroacetamide Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(NC(=O)C(F)(F)F)=CC=1)(O)CN1C=NN=N1 ZLJNVYHHBJHWCQ-UHFFFAOYSA-N 0.000 claims 2
- 241000894007 species Species 0.000 claims 2
- 230000009885 systemic effect Effects 0.000 claims 2
- IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 claims 2
- 201000005882 tinea unguium Diseases 0.000 claims 2
- 230000002485 urinary effect Effects 0.000 claims 2
- FMHFVGODKSOEKV-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-3-fluoro-1-(tetrazol-1-yl)-3-[5-[4-(2,2,2-trifluoroethoxy)phenyl]pyridin-2-yl]butan-2-ol Chemical compound C1=NN=NN1CC(O)(C=1C(=CC(F)=CC=1)F)C(F)(C)C(N=C1)=CC=C1C1=CC=C(OCC(F)(F)F)C=C1 FMHFVGODKSOEKV-UHFFFAOYSA-N 0.000 claims 1
- HSUXUELXFIFBIT-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-3-fluoro-1-(tetrazol-1-yl)-3-[5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl]butan-2-ol Chemical compound C1=NN=NN1CC(O)(C=1C(=CC(F)=CC=1)F)C(F)(C)C(N=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 HSUXUELXFIFBIT-UHFFFAOYSA-N 0.000 claims 1
- JVHZFKDSOUQLNB-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-3-fluoro-1-(tetrazol-1-yl)-3-[5-[4-(trifluoromethyl)phenyl]pyridin-2-yl]butan-2-ol Chemical compound C1=NN=NN1CC(O)(C=1C(=CC(F)=CC=1)F)C(F)(C)C(N=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 JVHZFKDSOUQLNB-UHFFFAOYSA-N 0.000 claims 1
- XAFSRHUAOWTMSL-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-3-fluoro-3-[5-(4-fluorophenyl)pyridin-2-yl]-1-(tetrazol-1-yl)butan-2-ol Chemical compound C1=NN=NN1CC(O)(C=1C(=CC(F)=CC=1)F)C(F)(C)C(N=C1)=CC=C1C1=CC=C(F)C=C1 XAFSRHUAOWTMSL-UHFFFAOYSA-N 0.000 claims 1
- KYMREFHKHDOGRO-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-3-fluoro-3-[5-(4-fluorophenyl)pyridin-2-yl]-1-(tetrazol-2-yl)butan-2-ol Chemical compound N1=CN=NN1CC(O)(C=1C(=CC(F)=CC=1)F)C(F)(C)C(N=C1)=CC=C1C1=CC=C(F)C=C1 KYMREFHKHDOGRO-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- PQEHIYKEYOVAFU-UHFFFAOYSA-N 3-[5-(4-chlorophenyl)pyridin-2-yl]-2-(2,4-difluorophenyl)-3-fluoro-1-(tetrazol-1-yl)butan-2-ol Chemical compound C1=NN=NN1CC(O)(C=1C(=CC(F)=CC=1)F)C(F)(C)C(N=C1)=CC=C1C1=CC=C(Cl)C=C1 PQEHIYKEYOVAFU-UHFFFAOYSA-N 0.000 claims 1
- 241000235389 Absidia Species 0.000 claims 1
- 241000228212 Aspergillus Species 0.000 claims 1
- 241001225321 Aspergillus fumigatus Species 0.000 claims 1
- 241000228405 Blastomyces dermatitidis Species 0.000 claims 1
- 241000222173 Candida parapsilosis Species 0.000 claims 1
- 241000233001 Carios Species 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 206010008803 Chromoblastomycosis Diseases 0.000 claims 1
- 208000015116 Chromomycosis Diseases 0.000 claims 1
- 241000543381 Cliftonia monophylla Species 0.000 claims 1
- 208000017701 Endocrine disease Diseases 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- LFVLUOAHQIVABZ-UHFFFAOYSA-N Iodofenphos Chemical compound COP(=S)(OC)OC1=CC(Cl)=C(I)C=C1Cl LFVLUOAHQIVABZ-UHFFFAOYSA-N 0.000 claims 1
- 241000235645 Pichia kudriavzevii Species 0.000 claims 1
- 241000233870 Pneumocystis Species 0.000 claims 1
- 241000233872 Pneumocystis carinii Species 0.000 claims 1
- 241000235527 Rhizopus Species 0.000 claims 1
- 240000005384 Rhizopus oryzae Species 0.000 claims 1
- 235000013752 Rhizopus oryzae Nutrition 0.000 claims 1
- 241000222481 Schizophyllum commune Species 0.000 claims 1
- 239000004037 angiogenesis inhibitor Substances 0.000 claims 1
- 230000001772 anti-angiogenic effect Effects 0.000 claims 1
- 230000001093 anti-cancer Effects 0.000 claims 1
- 229940091771 aspergillus fumigatus Drugs 0.000 claims 1
- 229940055022 candida parapsilosis Drugs 0.000 claims 1
- 230000029087 digestion Effects 0.000 claims 1
- 208000016097 disease of metabolism Diseases 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000007665 sagging Methods 0.000 claims 1
- 235000021419 vinegar Nutrition 0.000 claims 1
- 239000000052 vinegar Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261589076P | 2012-01-20 | 2012-01-20 | |
| US61/589,076 | 2012-01-20 | ||
| PCT/US2013/022313 WO2013109998A1 (en) | 2012-01-20 | 2013-01-18 | Metalloenzyme inhibitor compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015504095A JP2015504095A (ja) | 2015-02-05 |
| JP2015504095A5 true JP2015504095A5 (OSRAM) | 2016-03-03 |
| JP6189865B2 JP6189865B2 (ja) | 2017-08-30 |
Family
ID=48799718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014553491A Active JP6189865B2 (ja) | 2012-01-20 | 2013-01-18 | 金属酵素阻害薬化合物 |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US10221160B2 (OSRAM) |
| EP (1) | EP2804858B1 (OSRAM) |
| JP (1) | JP6189865B2 (OSRAM) |
| KR (1) | KR102061137B1 (OSRAM) |
| CN (1) | CN104136427B (OSRAM) |
| AU (2) | AU2013209516A1 (OSRAM) |
| BR (1) | BR112014017751B1 (OSRAM) |
| CA (1) | CA2861339C (OSRAM) |
| DK (1) | DK2804858T3 (OSRAM) |
| EA (1) | EA026209B1 (OSRAM) |
| ES (1) | ES2774267T3 (OSRAM) |
| IN (1) | IN2014DN06792A (OSRAM) |
| PL (1) | PL2804858T3 (OSRAM) |
| WO (1) | WO2013109998A1 (OSRAM) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2839769A1 (en) * | 2011-06-19 | 2012-12-27 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| AU2013209516A1 (en) * | 2012-01-20 | 2014-08-28 | Viamet Pharmaceuticals (NC), Inc. | Metalloenzyme inhibitor compounds |
| AU2015231234B2 (en) * | 2014-03-19 | 2019-04-04 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| JP6606508B2 (ja) * | 2014-03-19 | 2019-11-13 | マイコヴィア ファーマシューティカルズ，インコーポレイテッド | 抗真菌化合物の調製方法 |
| MX371291B (es) | 2014-03-19 | 2020-01-24 | Viamet Pharmaceuticals Nc Inc | 2-(2,4-difluorofenil)-1,1-difluoro-1-(5-sustituido-piridin-2-il)- 3-(1h-tetrazol-1-il)propan-2-oles y procedimientos para su preparacion. |
| AU2015231220B2 (en) * | 2014-03-19 | 2019-04-04 | The United States Of America, As Represented By The Secretary, Department Of Health & Human Services | 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 |
| EA037587B1 (ru) | 2014-03-19 | 2021-04-19 | Майковиа Фармасьютикалс, Инк. | Способ получения противогрибковых соединений |
| JP6518683B2 (ja) * | 2014-03-19 | 2019-05-22 | 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 |
| MX382905B (es) | 2014-03-19 | 2025-03-13 | Viamet Pharmaceuticals Nc Inc | 2-(2,4-difluorofenil)-1,1-difluoro-1-(5-sustituido-piridin-2-il)-3-(1h-tetrazol-1-il)propan-2-oles y procesos para su preparacion. |
| JP2017514790A (ja) * | 2014-03-19 | 2017-06-08 | ヴィアメット ファーマスーティカルズ，インコーポレイテッド | 抗真菌化合物の調製方法 |
| AU2015231270B2 (en) * | 2014-03-19 | 2019-03-07 | Viamet Pharmaceuticals (NC), Inc. | Antifungal compound process |
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2013
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- 2013-01-18 JP JP2014553491A patent/JP6189865B2/ja active Active
- 2013-01-18 US US14/373,314 patent/US10221160B2/en active Active
- 2013-01-18 PL PL13738427T patent/PL2804858T3/pl unknown
- 2013-01-18 EP EP13738427.7A patent/EP2804858B1/en active Active
- 2013-01-18 WO PCT/US2013/022313 patent/WO2013109998A1/en not_active Ceased
- 2013-01-18 ES ES13738427T patent/ES2774267T3/es active Active
- 2013-01-18 KR KR1020147023020A patent/KR102061137B1/ko active Active
- 2013-01-18 IN IN6792DEN2014 patent/IN2014DN06792A/en unknown
- 2013-01-18 CA CA2861339A patent/CA2861339C/en active Active
- 2013-01-18 DK DK13738427.7T patent/DK2804858T3/da active
- 2013-01-18 CN CN201380010231.4A patent/CN104136427B/zh active Active
- 2013-01-18 BR BR112014017751-1A patent/BR112014017751B1/pt active IP Right Grant
-
2017
- 2017-09-20 AU AU2017232080A patent/AU2017232080B2/en active Active
-
2019
- 2019-01-28 US US16/259,096 patent/US10526312B2/en active Active
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2020
- 2020-01-06 US US16/735,094 patent/US11247981B2/en active Active
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