AU2014278172B2 - Metalloenzyme inhibitor compounds - Google Patents
Metalloenzyme inhibitor compounds Download PDFInfo
- Publication number
- AU2014278172B2 AU2014278172B2 AU2014278172A AU2014278172A AU2014278172B2 AU 2014278172 B2 AU2014278172 B2 AU 2014278172B2 AU 2014278172 A AU2014278172 A AU 2014278172A AU 2014278172 A AU2014278172 A AU 2014278172A AU 2014278172 B2 AU2014278172 B2 AU 2014278172B2
- Authority
- AU
- Australia
- Prior art keywords
- optionally substituted
- difluoro
- ethynyl
- tetrazol
- 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.)
- Ceased
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 285
- 229940125956 metalloenzyme inhibitor Drugs 0.000 title description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 123
- 238000000034 method Methods 0.000 claims abstract description 85
- 201000010099 disease Diseases 0.000 claims abstract description 67
- 208000035475 disorder Diseases 0.000 claims abstract description 55
- 230000000694 effects Effects 0.000 claims abstract description 30
- 125000001188 haloalkyl group Chemical group 0.000 claims description 180
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 164
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 156
- -1 -CH2CF2CF3 Chemical group 0.000 claims description 152
- 125000000217 alkyl group Chemical group 0.000 claims description 146
- 125000005843 halogen group Chemical group 0.000 claims description 111
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 107
- 125000001072 heteroaryl group Chemical group 0.000 claims description 96
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 82
- 125000003545 alkoxy group Chemical group 0.000 claims description 78
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 72
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 71
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 70
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
- 125000003107 substituted aryl group Chemical group 0.000 claims description 61
- 125000000623 heterocyclic group Chemical group 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 54
- 150000003839 salts Chemical class 0.000 claims description 41
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 37
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 36
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 35
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 33
- 239000003795 chemical substances by application Substances 0.000 claims description 29
- 125000001153 fluoro group Chemical group F* 0.000 claims description 29
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 29
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 22
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 22
- KWZYOTGGTDCHLM-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[2-[4-[[5-(trifluoromethyl)thiophen-2-yl]methoxy]phenyl]ethynyl]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#CC=1C=CC(OCC=2SC(=CC=2)C(F)(F)F)=CC=1)(O)CN1C=NN=N1 KWZYOTGGTDCHLM-UHFFFAOYSA-N 0.000 claims description 20
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 15
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 14
- 210000003169 central nervous system Anatomy 0.000 claims description 14
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 12
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 11
- 230000002401 inhibitory effect Effects 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 9
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 9
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 8
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 8
- 239000002246 antineoplastic agent Substances 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 229940127089 cytotoxic agent Drugs 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 8
- 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 8
- 125000004963 sulfonylalkyl group Chemical group 0.000 claims description 8
- MWJTXCAJFGPQPZ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[(5-fluorothiophen-2-yl)methoxy]phenyl]ethynyl]pyridin-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#CC=1C=CC(OCC=2SC(F)=CC=2)=CC=1)(O)CN1C=NN=N1 MWJTXCAJFGPQPZ-UHFFFAOYSA-N 0.000 claims description 7
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 7
- 208000012931 Urologic disease Diseases 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 7
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 7
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 7
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 7
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 7
- 125000003368 amide group Chemical group 0.000 claims description 7
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 7
- 125000001769 aryl amino group Chemical group 0.000 claims description 7
- 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims description 7
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 7
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 7
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 125000005518 carboxamido group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 7
- 125000004986 diarylamino group Chemical group 0.000 claims description 7
- 208000010643 digestive system disease Diseases 0.000 claims description 7
- 208000016097 disease of metabolism Diseases 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 208000018685 gastrointestinal system disease Diseases 0.000 claims description 7
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 7
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
- 208000030159 metabolic disease Diseases 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 7
- 229940124597 therapeutic agent Drugs 0.000 claims description 7
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims description 7
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 7
- 208000014001 urinary system disease Diseases 0.000 claims description 7
- HOOPTQYPCOZSOB-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-(pyrazol-1-ylmethyl)phenyl]methoxy]phenyl]ethynyl]pyridin-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#CC=1C=CC(OCC=2C=CC(CN3N=CC=C3)=CC=2)=CC=1)(O)CN1C=NN=N1 HOOPTQYPCOZSOB-UHFFFAOYSA-N 0.000 claims description 6
- 125000005094 alkyl carbonyl amino alkyl group Chemical group 0.000 claims description 6
- 238000001727 in vivo Methods 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- ARADWGQKFCFEJC-UHFFFAOYSA-N 4-[2-[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenyl]-2-oxoethyl]benzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(=CC=1)C(=O)CC=1C=CC(=CC=1)C#N)(O)CN1C=NN=N1 ARADWGQKFCFEJC-UHFFFAOYSA-N 0.000 claims description 5
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- JDLIGMDIPUEOPH-UHFFFAOYSA-N n-[[4-[[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenoxy]methyl]phenyl]methyl]acetamide Chemical compound C1=CC(CNC(=O)C)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 JDLIGMDIPUEOPH-UHFFFAOYSA-N 0.000 claims description 5
- LBSOYTIILZKBBF-UHFFFAOYSA-N 1-[5-[2-[4-[(4-chlorophenyl)-hydroxymethyl]phenyl]ethynyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=CC=1C(O)C1=CC=C(Cl)C=C1 LBSOYTIILZKBBF-UHFFFAOYSA-N 0.000 claims description 4
- HZTPLXQVUPNTOW-UHFFFAOYSA-N 1-[[4-[[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenoxy]methyl]phenyl]methyl]pyrazole-4-carbonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=CC(CN3N=CC(=C3)C#N)=CC=2)=CC=1)(O)CN1C=NN=N1 HZTPLXQVUPNTOW-UHFFFAOYSA-N 0.000 claims description 4
- GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 claims description 4
- DOAOCQOFMHKDBN-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[1-hydroxy-2-(2,2,2-trifluoroethoxy)ethyl]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(C(COCC(F)(F)F)O)=CC=C1C#CC1=CC=C(C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)N=C1 DOAOCQOFMHKDBN-UHFFFAOYSA-N 0.000 claims description 4
- AITXUEMRKLKEAL-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-(1-hydroxyethyl)phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(C(O)C)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 AITXUEMRKLKEAL-UHFFFAOYSA-N 0.000 claims description 4
- XHRXWJSVLIERAL-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-(hydroxymethyl)phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(CO)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 XHRXWJSVLIERAL-UHFFFAOYSA-N 0.000 claims description 4
- WYOMUWIPXVJIQO-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-(morpholin-4-ylmethyl)phenyl]methoxy]phenyl]ethynyl]pyridin-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#CC=1C=CC(OCC=2C=CC(CN3CCOCC3)=CC=2)=CC=1)(O)CN1C=NN=N1 WYOMUWIPXVJIQO-UHFFFAOYSA-N 0.000 claims description 4
- NLIRDJQZVTYAAB-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-(pyrrolidin-1-ylmethyl)phenyl]methoxy]phenyl]ethynyl]pyridin-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#CC=1C=CC(OCC=2C=CC(CN3CCCC3)=CC=2)=CC=1)(O)CN1C=NN=N1 NLIRDJQZVTYAAB-UHFFFAOYSA-N 0.000 claims description 4
- JUJDSXNXSGENHH-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-[(1,3-oxazol-2-ylamino)methyl]phenyl]methoxy]phenyl]ethynyl]pyridin-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#CC=1C=CC(OCC=2C=CC(CNC=3OC=CN=3)=CC=2)=CC=1)(O)CN1C=NN=N1 JUJDSXNXSGENHH-UHFFFAOYSA-N 0.000 claims description 4
- IAKDRXVYNVLKES-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-[(4-fluoropyrazol-1-yl)methyl]phenyl]methoxy]phenyl]ethynyl]pyridin-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#CC=1C=CC(OCC=2C=CC(CN3N=CC(F)=C3)=CC=2)=CC=1)(O)CN1C=NN=N1 IAKDRXVYNVLKES-UHFFFAOYSA-N 0.000 claims description 4
- WRAJGSYVOCAYCT-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-[[4-(2-hydroxypropan-2-yl)pyrazol-1-yl]methyl]phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=C(C(C)(O)C)C=NN1CC(C=C1)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 WRAJGSYVOCAYCT-UHFFFAOYSA-N 0.000 claims description 4
- VBRIDLUYWZVABY-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-[[4-(2-methoxyethyl)pyrazol-1-yl]methyl]phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=C(CCOC)C=NN1CC(C=C1)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 VBRIDLUYWZVABY-UHFFFAOYSA-N 0.000 claims description 4
- NWHWQSRZKIFCTF-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[2-[4-[[4-(2,2,2-trifluoro-1-hydroxyethyl)phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]propan-2-ol Chemical compound C1=CC(C(O)C(F)(F)F)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 NWHWQSRZKIFCTF-UHFFFAOYSA-N 0.000 claims description 4
- JSLLQSWHQWTAQR-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[2-[4-[[4-(2,2,2-trifluoroethoxymethyl)phenyl]methoxy]phenyl]ethynyl]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#CC=1C=CC(OCC=2C=CC(COCC(F)(F)F)=CC=2)=CC=1)(O)CN1C=NN=N1 JSLLQSWHQWTAQR-UHFFFAOYSA-N 0.000 claims description 4
- FCKZXSSBYARFPX-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[2-[4-[[4-[(2,2,2-trifluoroethylamino)methyl]phenyl]methoxy]phenyl]ethynyl]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#CC=1C=CC(OCC=2C=CC(CNCC(F)(F)F)=CC=2)=CC=1)(O)CN1C=NN=N1 FCKZXSSBYARFPX-UHFFFAOYSA-N 0.000 claims description 4
- NKYSEDLJBNZIFT-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound OC(Cn1cnnn1)(C(F)F)c1ccc(F)cc1F NKYSEDLJBNZIFT-UHFFFAOYSA-N 0.000 claims description 4
- LUOXUHROCRVTTE-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-[2-[4-[[3-[1-(dimethylamino)-2-hydroxyethyl]phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound CN(C)C(CO)C1=CC=CC(COC=2C=CC(=CC=2)C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)=C1 LUOXUHROCRVTTE-UHFFFAOYSA-N 0.000 claims description 4
- QXRBUKMCPDVWEJ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-[2-[4-[[4-[(dimethylamino)methyl]-3-fluorophenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=C(F)C(CN(C)C)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 QXRBUKMCPDVWEJ-UHFFFAOYSA-N 0.000 claims description 4
- CHWQBIXLDCSMPI-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-[2-[4-[[4-[1-(dimethylamino)-2-hydroxyethyl]phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(C(CO)N(C)C)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 CHWQBIXLDCSMPI-UHFFFAOYSA-N 0.000 claims description 4
- SJSHIOIEIZPUGH-UHFFFAOYSA-N 2-[4-[[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenoxy]methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 SJSHIOIEIZPUGH-UHFFFAOYSA-N 0.000 claims description 4
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- ZIRBHNQVPBFJGX-UHFFFAOYSA-N 2-[[4-[[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenoxy]methyl]phenyl]methyl-methylamino]acetonitrile Chemical compound C1=CC(CN(CC#N)C)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 ZIRBHNQVPBFJGX-UHFFFAOYSA-N 0.000 claims description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- 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
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- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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| US201361834324P | 2013-06-12 | 2013-06-12 | |
| US61/834,324 | 2013-06-12 | ||
| PCT/US2014/041984 WO2014201161A1 (en) | 2013-06-12 | 2014-06-11 | Metalloenzyme inhibitor compounds |
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| AU2014278172A1 AU2014278172A1 (en) | 2016-01-28 |
| AU2014278172B2 true AU2014278172B2 (en) | 2018-08-09 |
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| EA (1) | EA201690007A1 (https=) |
| WO (1) | WO2014201161A1 (https=) |
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| EP3351541A1 (en) | 2011-12-11 | 2018-07-25 | Viamet Pharmaceuticals (NC), Inc. | Metalloenzyme inhibitor compounds |
| ES2774267T3 (es) * | 2012-01-20 | 2020-07-20 | Mycovia Pharmaceuticals Inc | Compuestos inhibidores de metaloenzimas |
| AU2015231226B2 (en) | 2014-03-19 | 2019-04-04 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| JP6633539B2 (ja) | 2014-03-19 | 2020-01-22 | ダウ アグロサイエンシィズ エルエルシー | ２−（２，４−ジフルオロフェニル）−１，１−ジフルオロ−１−（５−置換−ピリジン−２−イル）−３−（１ｈ−テトラゾール−１−イル）プロパン−２−オールおよびその調製工程 |
| ES2800905T3 (es) | 2014-03-19 | 2021-01-05 | Mycovia Pharmaceuticals Inc | Procedimiento para compuesto antifúngico |
| CA2942972A1 (en) | 2014-03-19 | 2015-09-24 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Antifungal compound process |
| BR112016021257B1 (pt) | 2014-03-19 | 2021-03-02 | Viamet Pharmaceuticals (NC), Inc. | 2-(2,4- difluorofenil-1,1-diflúor-1-(5-substituído-piridin-2-il)-3- (1h-tetrazol-1-il)propan-2-óis e processos para preparação e uso dos mesmos |
| CA2942231A1 (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 |
| 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 |
| MA40943A (fr) | 2014-11-10 | 2017-09-19 | Constellation Pharmaceuticals Inc | Pyrrolopyridines substituées utilisées en tant qu'inhibiteurs de bromodomaines |
| MA40940A (fr) | 2014-11-10 | 2017-09-19 | Constellation Pharmaceuticals Inc | Pyrrolopyridines substituées utilisées en tant qu'inhibiteurs de bromodomaines |
| WO2016077375A1 (en) | 2014-11-10 | 2016-05-19 | Genentech, Inc. | Bromodomain inhibitors and uses thereof |
| EP3250571B1 (en) * | 2015-01-29 | 2022-11-30 | Genentech, Inc. | Therapeutic compounds and uses thereof |
| JP6847458B2 (ja) | 2015-09-18 | 2021-03-24 | 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 | 抗真菌化合物のプロセス |
| KR102240920B1 (ko) | 2015-12-30 | 2021-04-16 | 브이피에스-3, 엘엘씨 | 금속 효소 억제 화합물 |
| CN111818928A (zh) | 2018-03-05 | 2020-10-23 | 艾库斯生物科学有限公司 | 精氨酸酶抑制剂 |
| EP3873916B8 (en) * | 2018-10-29 | 2025-03-26 | Shanghai Synergy Pharmaceutical Sciences, Ltd. | Novel dipeptide compounds and uses thereof |
| ES3034676T3 (en) | 2018-11-16 | 2025-08-21 | Arcus Biosciences Inc | Inhibitors of arg1 and/or arg2 |
| WO2020263191A1 (en) | 2019-06-27 | 2020-12-30 | Nanyang Technological University | Compounds having antimalarial activity |
| CN110885323A (zh) * | 2019-12-02 | 2020-03-17 | 中国人民解放军第二军医大学 | 一种三氮唑醇类衍生物、其制备方法及应用 |
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| KR20080062876A (ko) | 2006-12-29 | 2008-07-03 | 주식회사 대웅제약 | 신규한 항진균성 트리아졸 유도체 |
| AU2011242562B2 (en) * | 2010-04-24 | 2016-10-13 | Mycovia Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| WO2012177635A1 (en) * | 2011-06-19 | 2012-12-27 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| IN2014MN00093A (https=) * | 2011-06-19 | 2015-06-19 | Viamet Pharmaceuticals Inc | |
| EA025266B1 (ru) | 2011-06-23 | 2016-12-30 | Ваймет Фармасьютикалс, Инк. | Соединения, ингибирующие металлоферменты |
| EP3351541A1 (en) * | 2011-12-11 | 2018-07-25 | Viamet Pharmaceuticals (NC), Inc. | Metalloenzyme inhibitor compounds |
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| US9688671B2 (en) | 2017-06-27 |
| CA2915054A1 (en) | 2014-12-18 |
| EA201690007A1 (ru) | 2016-04-29 |
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| WO2014201161A1 (en) | 2014-12-18 |
| AU2014278172A1 (en) | 2016-01-28 |
| EP3008051A4 (en) | 2017-03-01 |
| JP6386035B2 (ja) | 2018-09-05 |
| JP2016526535A (ja) | 2016-09-05 |
| CN105431418A (zh) | 2016-03-23 |
| US20160130263A1 (en) | 2016-05-12 |
| CN105431418B (zh) | 2019-02-05 |
| EP3008051A1 (en) | 2016-04-20 |
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| Date | Code | Title | Description |
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| HB | Alteration of name in register |
Owner name: VIAMET PHARMACEUTICALS (NC), INC. Free format text: FORMER NAME(S): VIAMET PHARMACEUTICALS, INC. |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| HB | Alteration of name in register |
Owner name: MYCOVIA PHARMACEUTICALS, INC. Free format text: FORMER NAME(S): VIAMET PHARMACEUTICALS (NC), INC. |
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| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |