JP2013527170A5 - - Google Patents
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- Publication number
- JP2013527170A5 JP2013527170A5 JP2013508570A JP2013508570A JP2013527170A5 JP 2013527170 A5 JP2013527170 A5 JP 2013527170A5 JP 2013508570 A JP2013508570 A JP 2013508570A JP 2013508570 A JP2013508570 A JP 2013508570A JP 2013527170 A5 JP2013527170 A5 JP 2013527170A5
- Authority
- JP
- Japan
- Prior art keywords
- ylcarbamoyl
- benzoic acid
- chloro
- difluorobiphenyl
- difluoro
- 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
- -1 2- (3-chlorobiphenyl-4-ylcarbamoyl) benzoic acid Chemical compound 0.000 claims description 113
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 67
- 150000001875 compounds Chemical class 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 5
- SBHJMNICVOXTQZ-UHFFFAOYSA-N 2-[[4-(3-ethylphenyl)-2,6-difluorophenyl]carbamoyl]benzoic acid Chemical compound CCC1=CC=CC(C=2C=C(F)C(NC(=O)C=3C(=CC=CC=3)C(O)=O)=C(F)C=2)=C1 SBHJMNICVOXTQZ-UHFFFAOYSA-N 0.000 claims description 3
- TWQHHHPXDZGCIG-UHFFFAOYSA-N ClC1=C(C=C(C=C1)OC)C1=CC(=C(C(=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1)Cl.ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)F)C1=CC(=C(C=C1)OC)OC Chemical compound ClC1=C(C=C(C=C1)OC)C1=CC(=C(C(=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1)Cl.ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)F)C1=CC(=C(C=C1)OC)OC TWQHHHPXDZGCIG-UHFFFAOYSA-N 0.000 claims description 3
- FICLAEURQAAHTA-UHFFFAOYSA-N FC1=C(C(=CC(=C1)C=1C=C2C(=CNC2=CC1)C)F)NC(=O)C1=C(C(=O)O)C=CC=C1.FC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)F)C1=CC(=C(C=C1)F)OC Chemical compound FC1=C(C(=CC(=C1)C=1C=C2C(=CNC2=CC1)C)F)NC(=O)C1=C(C(=O)O)C=CC=C1.FC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)F)C1=CC(=C(C=C1)F)OC FICLAEURQAAHTA-UHFFFAOYSA-N 0.000 claims description 3
- BMHUUYIRKGWQOG-UHFFFAOYSA-N 2-[[2,6-difluoro-4-(2-fluoro-5-methoxyphenyl)phenyl]carbamoyl]benzoic acid Chemical compound COC1=CC=C(F)C(C=2C=C(F)C(NC(=O)C=3C(=CC=CC=3)C(O)=O)=C(F)C=2)=C1 BMHUUYIRKGWQOG-UHFFFAOYSA-N 0.000 claims description 2
- QKVOWFUJEINWNQ-UHFFFAOYSA-N 2-[[2,6-difluoro-4-(3-methyl-2h-indazol-5-yl)phenyl]carbamoyl]benzoic acid Chemical compound C1=C2C(C)=NNC2=CC=C1C(C=C1F)=CC(F)=C1NC(=O)C1=CC=CC=C1C(O)=O QKVOWFUJEINWNQ-UHFFFAOYSA-N 0.000 claims description 2
- OIIQWCVDOBWRMJ-UHFFFAOYSA-N 2-[[2,6-difluoro-4-(3-propan-2-yloxyphenyl)phenyl]carbamoyl]benzoic acid Chemical compound CC(C)OC1=CC=CC(C=2C=C(F)C(NC(=O)C=3C(=CC=CC=3)C(O)=O)=C(F)C=2)=C1 OIIQWCVDOBWRMJ-UHFFFAOYSA-N 0.000 claims description 2
- UFDYYDSVVQSNDS-UHFFFAOYSA-N 2-[[2,6-difluoro-4-[3-(trifluoromethoxy)phenyl]phenyl]carbamoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=C(F)C=C(C=2C=C(OC(F)(F)F)C=CC=2)C=C1F UFDYYDSVVQSNDS-UHFFFAOYSA-N 0.000 claims description 2
- IQAORFMYZPKQBX-UHFFFAOYSA-N 2-[[4-(1,3-benzodioxol-5-yl)-2,6-difluorophenyl]carbamoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=C(F)C=C(C=2C=C3OCOC3=CC=2)C=C1F IQAORFMYZPKQBX-UHFFFAOYSA-N 0.000 claims description 2
- NCVIXOCOLVIPLS-UHFFFAOYSA-N 2-[[4-(3-cyclopropyloxyphenyl)-2-fluorophenyl]carbamoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=CC=C(C=2C=C(OC3CC3)C=CC=2)C=C1F NCVIXOCOLVIPLS-UHFFFAOYSA-N 0.000 claims description 2
- LEHLVDDUGIBISB-UHFFFAOYSA-N 2-[[4-(3-ethoxyphenyl)-2,6-difluorophenyl]carbamoyl]benzoic acid Chemical compound CCOC1=CC=CC(C=2C=C(F)C(NC(=O)C=3C(=CC=CC=3)C(O)=O)=C(F)C=2)=C1 LEHLVDDUGIBISB-UHFFFAOYSA-N 0.000 claims description 2
- JCCCPFBYVRGUPS-UHFFFAOYSA-N 2-[[4-(3-ethylphenyl)phenyl]carbamoyl]benzoic acid Chemical compound CCC1=CC=CC(C=2C=CC(NC(=O)C=3C(=CC=CC=3)C(O)=O)=CC=2)=C1 JCCCPFBYVRGUPS-UHFFFAOYSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims 29
- 235000010233 benzoic acid Nutrition 0.000 claims 27
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 150000002431 hydrogen Chemical group 0.000 claims 6
- 229920006395 saturated elastomer Polymers 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 150000001204 N-oxides Chemical class 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000006414 CCl Chemical group ClC* 0.000 claims 3
- 101000998146 Homo sapiens Interleukin-17A Proteins 0.000 claims 3
- 102100033461 Interleukin-17A Human genes 0.000 claims 3
- 206010040070 Septic Shock Diseases 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 230000005764 inhibitory process Effects 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 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 claims 2
- 208000020084 Bone disease Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010011831 Cytomegalovirus infection Diseases 0.000 claims 2
- 101710088194 Dehydrogenase Proteins 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 206010040047 Sepsis Diseases 0.000 claims 2
- 150000008065 acid anhydrides Chemical class 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- UFIVEPVSAGBUSI-UHFFFAOYSA-N dihydroorotic acid Chemical compound OC(=O)C1CC(=O)NC(=O)N1 UFIVEPVSAGBUSI-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 201000000306 sarcoidosis Diseases 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 150000003536 tetrazoles Chemical class 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 1
- YNVYQKPNYNUJGZ-UHFFFAOYSA-N 2-[[2,6-difluoro-4-(2-fluorophenyl)phenyl]carbamoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=C(F)C=C(C=2C(=CC=CC=2)F)C=C1F YNVYQKPNYNUJGZ-UHFFFAOYSA-N 0.000 claims 1
- HNRIJIAFLCALMB-UHFFFAOYSA-N 2-[[2-chloro-4-(3-cyclopentyloxyphenyl)-6-fluorophenyl]carbamoyl]benzoic acid 2-[[4-[3-(difluoromethoxy)phenyl]-2,6-difluorophenyl]carbamoyl]benzoic acid Chemical compound FC(OC=1C=C(C=CC1)C1=CC(=C(C(=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1)F)F.ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)F)C1=CC(=CC=C1)OC1CCCC1 HNRIJIAFLCALMB-UHFFFAOYSA-N 0.000 claims 1
- LHQYZGSHIDHMFV-UHFFFAOYSA-N 2-[[2-chloro-4-[3-(difluoromethoxy)phenyl]-6-fluorophenyl]carbamoyl]benzoic acid 2-[[4-(2-chloro-5-methoxyphenyl)-2,6-difluorophenyl]carbamoyl]benzoic acid Chemical compound ClC1=C(C=C(C=C1)OC)C1=CC(=C(C(=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1)F.ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)F)C1=CC(=CC=C1)OC(F)F LHQYZGSHIDHMFV-UHFFFAOYSA-N 0.000 claims 1
- OSZLNJXHFPFJIP-UHFFFAOYSA-N 2-[[2-chloro-4-[3-(difluoromethoxy)phenyl]-6-fluorophenyl]carbamoyl]benzoic acid 2-[[4-[3-(difluoromethoxy)phenyl]-2,6-difluorophenyl]carbamoyl]benzoic acid Chemical compound ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)F)C1=CC(=CC=C1)OC(F)F.FC(OC=1C=C(C=CC1)C1=CC(=C(C(=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1)F)F OSZLNJXHFPFJIP-UHFFFAOYSA-N 0.000 claims 1
- KJOYEPSKYFDKLM-UHFFFAOYSA-N 2-[[2-chloro-6-fluoro-4-[3-(trifluoromethoxy)phenyl]phenyl]carbamoyl]benzoic acid 2-[(2,6-difluoro-4-phenylmethoxyphenyl)carbamoyl]benzoic acid Chemical compound C(C1=CC=CC=C1)OC1=CC(=C(C(=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1)F.ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)F)C1=CC(=CC=C1)OC(F)(F)F KJOYEPSKYFDKLM-UHFFFAOYSA-N 0.000 claims 1
- GOVXKUCVZUROAN-UHFFFAOYSA-N 3-ethyl-1h-indole Chemical compound C1=CC=C2C(CC)=CNC2=C1 GOVXKUCVZUROAN-UHFFFAOYSA-N 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000027496 Behcet disease Diseases 0.000 claims 1
- 208000009137 Behcet syndrome Diseases 0.000 claims 1
- BONSAMLNNLHYSV-UHFFFAOYSA-N C1(CCCC1)OC=1C=C(C=CC1)C1=CC(=C(C(=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1)F.C(C1=CC=CC=C1)OC1=CC(=C(C(=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1)F Chemical compound C1(CCCC1)OC=1C=C(C=CC1)C1=CC(=C(C(=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1)F.C(C1=CC=CC=C1)OC1=CC(=C(C(=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1)F BONSAMLNNLHYSV-UHFFFAOYSA-N 0.000 claims 1
- OONOSCXDNGTQLB-UHFFFAOYSA-N CN1N=C(C2=CC(=CC=C12)C1=CC(=C(C(=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1)F)C.ClC1=C(C(=CC(=C1)C=1C=CC2=C(CCO2)C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1 Chemical compound CN1N=C(C2=CC(=CC=C12)C1=CC(=C(C(=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1)F)C.ClC1=C(C(=CC(=C1)C=1C=CC2=C(CCO2)C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1 OONOSCXDNGTQLB-UHFFFAOYSA-N 0.000 claims 1
- 208000000668 Chronic Pancreatitis Diseases 0.000 claims 1
- PSCJGWHQAIUEET-UHFFFAOYSA-N ClC1=C(C(=CC(=C1)C=1C=C2C(=CNC2=CC1)CC)F)NC(=O)C1=C(C(=O)O)C=CC=C1.FC1=C(C(=CC(=C1)C=1C=C2C(=CNC2=CC1)CCC)F)NC(=O)C1=C(C(=O)O)C=CC=C1 Chemical compound ClC1=C(C(=CC(=C1)C=1C=C2C(=CNC2=CC1)CC)F)NC(=O)C1=C(C(=O)O)C=CC=C1.FC1=C(C(=CC(=C1)C=1C=C2C(=CNC2=CC1)CCC)F)NC(=O)C1=C(C(=O)O)C=CC=C1 PSCJGWHQAIUEET-UHFFFAOYSA-N 0.000 claims 1
- QCIBXDQMEHXQID-UHFFFAOYSA-N ClC1=CC(=C(C(=O)O)C=C1Cl)C(NC1=C(C=C(C=C1F)C1=C(C=CC=C1)Cl)F)=O.C(CCC)OC=1C=C(C=CC1)C1=CC(=C(C(=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1)Cl Chemical compound ClC1=CC(=C(C(=O)O)C=C1Cl)C(NC1=C(C=C(C=C1F)C1=C(C=CC=C1)Cl)F)=O.C(CCC)OC=1C=C(C=CC1)C1=CC(=C(C(=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1)Cl QCIBXDQMEHXQID-UHFFFAOYSA-N 0.000 claims 1
- STKHSDVCMQFGCR-UHFFFAOYSA-N ClC1=CC(=C(C(=O)O)C=C1Cl)C(NC1=C(C=C(C=C1F)C1=CC(=CC=C1)OC)F)=O.ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)F)C1=CC(=CC=C1)OCC Chemical compound ClC1=CC(=C(C(=O)O)C=C1Cl)C(NC1=C(C=C(C=C1F)C1=CC(=CC=C1)OC)F)=O.ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)F)C1=CC(=CC=C1)OCC STKHSDVCMQFGCR-UHFFFAOYSA-N 0.000 claims 1
- TWQYMBDLIGHTGB-UHFFFAOYSA-N ClC=1C=C(C=C(C1)OC)C1=CC(=C(C(=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1)F.CN1N=C(C2=CC(=CC=C12)C1=CC(=C(C(=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1)F)C Chemical compound ClC=1C=C(C=C(C1)OC)C1=CC(=C(C(=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1)F.CN1N=C(C2=CC(=CC=C12)C1=CC(=C(C(=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1)F)C TWQYMBDLIGHTGB-UHFFFAOYSA-N 0.000 claims 1
- OLSRZNOBBAVTEO-UHFFFAOYSA-N ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)Cl)C1=CC(=CC=C1)OC.ClC1=CC(=C(C(=O)O)C=C1Cl)C(NC1=C(C=C(C=C1F)C1=CC(=CC=C1)OCC)F)=O Chemical compound ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)Cl)C1=CC(=CC=C1)OC.ClC1=CC(=C(C(=O)O)C=C1Cl)C(NC1=C(C=C(C=C1F)C1=CC(=CC=C1)OCC)F)=O OLSRZNOBBAVTEO-UHFFFAOYSA-N 0.000 claims 1
- FFARWXFJMDUFJF-UHFFFAOYSA-N ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)Cl)C1=CC(=CC=C1)OCC.ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)F)C1=C(C=CC=C1)F.ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)F)C1=CC(=CC=C1)OCCC Chemical compound ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)Cl)C1=CC(=CC=C1)OCC.ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)F)C1=C(C=CC=C1)F.ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)F)C1=CC(=CC=C1)OCCC FFARWXFJMDUFJF-UHFFFAOYSA-N 0.000 claims 1
- ZZMKIJZRUVUEDS-UHFFFAOYSA-N ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)F)C1=CC(=CC=C1)CC.FC1=C(C(=CC(=C1)C=1C=C2C(=NNC2=CC1)C)F)NC(=O)C1=C(C(=O)O)C=CC=C1 Chemical compound ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)F)C1=CC(=CC=C1)CC.FC1=C(C(=CC(=C1)C=1C=C2C(=NNC2=CC1)C)F)NC(=O)C1=C(C(=O)O)C=CC=C1 ZZMKIJZRUVUEDS-UHFFFAOYSA-N 0.000 claims 1
- DOLNZTDHFVFPEN-UHFFFAOYSA-N ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)F)C1=CC(=CC=C1)OC1CCCC1.C1(CCCC1)OC=1C=C(C=CC1)C1=CC(=C(C(=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1)F Chemical compound ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)F)C1=CC(=CC=C1)OC1CCCC1.C1(CCCC1)OC=1C=C(C=CC1)C1=CC(=C(C(=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1)F DOLNZTDHFVFPEN-UHFFFAOYSA-N 0.000 claims 1
- XNFJLRFEUNAXKE-UHFFFAOYSA-N ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)F)C1=CC(=CC=C1)OCC(F)(F)F.ClC1=C(C(=CC(=C1)C1=CC2=C(OCCO2)C=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1 Chemical compound ClC=1C=C(C=C(C1NC(=O)C1=C(C(=O)O)C=CC=C1)F)C1=CC(=CC=C1)OCC(F)(F)F.ClC1=C(C(=CC(=C1)C1=CC2=C(OCCO2)C=C1)F)NC(=O)C1=C(C(=O)O)C=CC=C1 XNFJLRFEUNAXKE-UHFFFAOYSA-N 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 206010012442 Dermatitis contact Diseases 0.000 claims 1
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| US9216983B2 (en) | 2007-12-21 | 2015-12-22 | Board Of Regents, University Of Texas System | Dihydroorotate dehydrogenase inhibitors with selective anti-malarial activity |
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