JP5452925B2 - Ｐｇｄｓ阻害剤としてのピリミジンアミド化合物 - Google Patents

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Publication number

JP5452925B2

JP5452925B2 JP2008534664A JP2008534664A JP5452925B2 JP 5452925 B2 JP5452925 B2 JP 5452925B2 JP 2008534664 A JP2008534664 A JP 2008534664A JP 2008534664 A JP2008534664 A JP 2008534664A JP 5452925 B2 JP5452925 B2 JP 5452925B2

Authority

JP

Japan

Prior art keywords

phenyl

pyrimidine

carboxylic acid

benzylamide

fluoro

Prior art date

2005-10-04

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.)

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• 239000003112 inhibitor Substances 0.000 title description 6
• 102100029100 Hematopoietic prostaglandin D synthase Human genes 0.000 title description 3
• 101710145576 Prostaglandin-H2 D-isomerase Proteins 0.000 title description 2
• FUXJMHXHGDAHPD-UHFFFAOYSA-N pyrimidine-2-carboxamide Chemical class NC(=O)C1=NC=CC=N1 FUXJMHXHGDAHPD-UHFFFAOYSA-N 0.000 title description 2
• -1 hydroxy, carboxy, amidino Chemical group 0.000 claims description 257
• 150000001875 compounds Chemical class 0.000 claims description 94
• 125000001072 heteroaryl group Chemical group 0.000 claims description 90
• 229910052757 nitrogen Inorganic materials 0.000 claims description 88
• 229910052739 hydrogen Inorganic materials 0.000 claims description 78
• 125000000217 alkyl group Chemical group 0.000 claims description 76
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 74
• 150000003839 salts Chemical class 0.000 claims description 74
• 125000003545 alkoxy group Chemical group 0.000 claims description 69
• 125000005843 halogen group Chemical group 0.000 claims description 69
• 125000000623 heterocyclic group Chemical group 0.000 claims description 69
• 125000003118 aryl group Chemical group 0.000 claims description 64
• 150000001204 N-oxides Chemical class 0.000 claims description 58
• 239000012453 solvate Substances 0.000 claims description 57
• 229910052717 sulfur Chemical group 0.000 claims description 47
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 43
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 42
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 36
• BOAIYSRFGWBZCF-UHFFFAOYSA-N 2-phenylpyrimidine-5-carboxylic acid Chemical compound N1=CC(C(=O)O)=CN=C1C1=CC=CC=C1 BOAIYSRFGWBZCF-UHFFFAOYSA-N 0.000 claims description 31
• DYPNEVXAPRDVCM-UHFFFAOYSA-N 2-(3-fluorophenyl)pyrimidine-5-carboxylic acid Chemical compound N1=CC(C(=O)O)=CN=C1C1=CC=CC(F)=C1 DYPNEVXAPRDVCM-UHFFFAOYSA-N 0.000 claims description 30
• 229910052760 oxygen Inorganic materials 0.000 claims description 22
• 239000001301 oxygen Substances 0.000 claims description 22
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 21
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 21
• 125000001188 haloalkyl group Chemical group 0.000 claims description 21
• 239000001257 hydrogen Substances 0.000 claims description 21
• 125000003282 alkyl amino group Chemical group 0.000 claims description 19
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 17
• 125000003342 alkenyl group Chemical group 0.000 claims description 15
• 125000000304 alkynyl group Chemical group 0.000 claims description 15
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 14
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 14
• 125000004414 alkyl thio group Chemical group 0.000 claims description 14
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
• 125000004076 pyridyl group Chemical group 0.000 claims description 12
• IOFQQZZRBFKEIF-UHFFFAOYSA-N 2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrimidine-5-carboxylic acid Chemical compound O1C(C)=NC(C=2N=CC(=CN=2)C(O)=O)=N1 IOFQQZZRBFKEIF-UHFFFAOYSA-N 0.000 claims description 11
• 125000002252 acyl group Chemical group 0.000 claims description 11
• 125000003435 aroyl group Chemical group 0.000 claims description 11
• 125000005842 heteroatom Chemical group 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 125000004104 aryloxy group Chemical group 0.000 claims description 10
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 10
• 208000006673 asthma Diseases 0.000 claims description 9
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 8
• 201000010105 allergic rhinitis Diseases 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 150000002431 hydrogen Chemical class 0.000 claims description 8
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 8
• 125000003386 piperidinyl group Chemical group 0.000 claims description 8
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 8
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 7
• 125000002883 imidazolyl group Chemical group 0.000 claims description 7
• 239000011593 sulfur Chemical group 0.000 claims description 7
• 125000000335 thiazolyl group Chemical group 0.000 claims description 7
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
• PRBPIPZPHABGIA-UHFFFAOYSA-N 2-(3-fluorophenyl)-4-methyl-n-[[3-[(propan-2-ylsulfonylamino)methyl]phenyl]methyl]pyrimidine-5-carboxamide Chemical compound CC(C)S(=O)(=O)NCC1=CC=CC(CNC(=O)C=2C(=NC(=NC=2)C=2C=C(F)C=CC=2)C)=C1 PRBPIPZPHABGIA-UHFFFAOYSA-N 0.000 claims description 6
• FMVLDCBNRZZNPH-UHFFFAOYSA-N 3-(aminomethyl)-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(CN)=C1 FMVLDCBNRZZNPH-UHFFFAOYSA-N 0.000 claims description 6
• 208000026935 allergic disease Diseases 0.000 claims description 6
• 230000000172 allergic effect Effects 0.000 claims description 6
• 208000027866 inflammatory disease Diseases 0.000 claims description 6
• 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 5
• 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 5
• AJHRVJDBJZHLOT-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[[3-(2-hydroxypropylsulfamoyl)phenyl]methyl]pyrimidine-5-carboxamide Chemical compound CC(O)CNS(=O)(=O)C1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2C=C(F)C=CC=2)=C1 AJHRVJDBJZHLOT-UHFFFAOYSA-N 0.000 claims description 5
• BTPMPSXYHSQPTQ-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[[3-(3-pyrrolidin-1-ylpropylsulfamoyl)phenyl]methyl]pyrimidine-5-carboxamide Chemical compound FC1=CC=CC(C=2N=CC(=CN=2)C(=O)NCC=2C=C(C=CC=2)S(=O)(=O)NCCCN2CCCC2)=C1 BTPMPSXYHSQPTQ-UHFFFAOYSA-N 0.000 claims description 5
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000001041 indolyl group Chemical group 0.000 claims description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• VAECNHCIFKAKQZ-UHFFFAOYSA-N n-[(3,4-dimethoxyphenyl)methyl]-2-phenylpyrimidine-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1CNC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1 VAECNHCIFKAKQZ-UHFFFAOYSA-N 0.000 claims description 5
• XTHAICUIEOFRFR-UHFFFAOYSA-N n-[(3-aminophenyl)methyl]-2-phenylpyrimidine-5-carboxamide Chemical compound NC1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2C=CC=CC=2)=C1 XTHAICUIEOFRFR-UHFFFAOYSA-N 0.000 claims description 5
• 125000002971 oxazolyl group Chemical group 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 4
• IPSZHIILJNFYHA-UHFFFAOYSA-N 2-(3-fluorophenyl)-4-methyl-n-[[3-(methylsulfamoylmethyl)phenyl]methyl]pyrimidine-5-carboxamide Chemical compound CNS(=O)(=O)CC1=CC=CC(CNC(=O)C=2C(=NC(=NC=2)C=2C=C(F)C=CC=2)C)=C1 IPSZHIILJNFYHA-UHFFFAOYSA-N 0.000 claims description 4
• VTYVJBLNCPQAMD-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[(1-methylsulfonylpiperidin-3-yl)methyl]pyrimidine-5-carboxamide Chemical compound C1N(S(=O)(=O)C)CCCC1CNC(=O)C1=CN=C(C=2C=C(F)C=CC=2)N=C1 VTYVJBLNCPQAMD-UHFFFAOYSA-N 0.000 claims description 4
• CVIVDDVYQNGPFI-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[(3-morpholin-4-ylsulfonylphenyl)methyl]pyrimidine-5-carboxamide Chemical compound FC1=CC=CC(C=2N=CC(=CN=2)C(=O)NCC=2C=C(C=CC=2)S(=O)(=O)N2CCOCC2)=C1 CVIVDDVYQNGPFI-UHFFFAOYSA-N 0.000 claims description 4
• AQEJAKJQPXKMBE-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[[3-(3-oxopiperazin-1-yl)sulfonylphenyl]methyl]pyrimidine-5-carboxamide Chemical compound FC1=CC=CC(C=2N=CC(=CN=2)C(=O)NCC=2C=C(C=CC=2)S(=O)(=O)N2CC(=O)NCC2)=C1 AQEJAKJQPXKMBE-UHFFFAOYSA-N 0.000 claims description 4
• MMFUHFAXUOPVJN-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[[3-(methanesulfonamidomethyl)phenyl]methyl]pyrimidine-5-carboxamide Chemical compound CS(=O)(=O)NCC1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2C=C(F)C=CC=2)=C1 MMFUHFAXUOPVJN-UHFFFAOYSA-N 0.000 claims description 4
• FHOQDCKZUYVRRR-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[[3-(methylsulfamoyl)phenyl]methyl]pyrimidine-5-carboxamide Chemical compound CNS(=O)(=O)C1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2C=C(F)C=CC=2)=C1 FHOQDCKZUYVRRR-UHFFFAOYSA-N 0.000 claims description 4
• MXULIDFRXJOTDY-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[[3-(methylsulfamoylmethyl)phenyl]methyl]pyrimidine-5-carboxamide Chemical compound CNS(=O)(=O)CC1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2C=C(F)C=CC=2)=C1 MXULIDFRXJOTDY-UHFFFAOYSA-N 0.000 claims description 4
• BWSJHYBIWIZWNA-UHFFFAOYSA-N 2-phenyl-n-(2-sulfamoylethyl)pyrimidine-5-carboxamide Chemical compound N1=CC(C(=O)NCCS(=O)(=O)N)=CN=C1C1=CC=CC=C1 BWSJHYBIWIZWNA-UHFFFAOYSA-N 0.000 claims description 4
• JSFAAXVTHOLLEY-UHFFFAOYSA-N 2-phenyl-n-[(4-sulfamoylphenyl)methyl]pyrimidine-5-carboxamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1 JSFAAXVTHOLLEY-UHFFFAOYSA-N 0.000 claims description 4
• 125000002947 alkylene group Chemical group 0.000 claims description 4
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• BUPURDLTPRTENO-UHFFFAOYSA-N n-(oxan-4-ylmethyl)-2-phenylpyrimidine-5-carboxamide Chemical compound C=1N=C(C=2C=CC=CC=2)N=CC=1C(=O)NCC1CCOCC1 BUPURDLTPRTENO-UHFFFAOYSA-N 0.000 claims description 4
• KAGFKCFKLSCARE-UHFFFAOYSA-N n-[(4-morpholin-4-ylphenyl)methyl]-2-phenylpyrimidine-5-carboxamide Chemical compound C=1N=C(C=2C=CC=CC=2)N=CC=1C(=O)NCC(C=C1)=CC=C1N1CCOCC1 KAGFKCFKLSCARE-UHFFFAOYSA-N 0.000 claims description 4
• PCZRNCUJIFEFSR-UHFFFAOYSA-N n-[2-(1,3-benzodioxol-5-yl)ethyl]-2-phenylpyrimidine-5-carboxamide Chemical compound C=1C=C2OCOC2=CC=1CCNC(=O)C(C=N1)=CN=C1C1=CC=CC=C1 PCZRNCUJIFEFSR-UHFFFAOYSA-N 0.000 claims description 4
• GJVUYZVCBGAFIX-UHFFFAOYSA-N n-[2-(dimethylsulfamoyl)ethyl]-2-phenylpyrimidine-5-carboxamide Chemical compound N1=CC(C(=O)NCCS(=O)(=O)N(C)C)=CN=C1C1=CC=CC=C1 GJVUYZVCBGAFIX-UHFFFAOYSA-N 0.000 claims description 4
• MJOYMGYUFBZHCX-UHFFFAOYSA-N n-[[3-(acetylsulfamoyl)phenyl]methyl]-2-(3-fluorophenyl)pyrimidine-5-carboxamide Chemical compound CC(=O)NS(=O)(=O)C1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2C=C(F)C=CC=2)=C1 MJOYMGYUFBZHCX-UHFFFAOYSA-N 0.000 claims description 4
• OLXYCBXQUUIXNV-UHFFFAOYSA-N n-[[3-(ethylsulfamoyl)phenyl]methyl]-2-(3-fluorophenyl)pyrimidine-5-carboxamide Chemical compound CCNS(=O)(=O)C1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2C=C(F)C=CC=2)=C1 OLXYCBXQUUIXNV-UHFFFAOYSA-N 0.000 claims description 4
• JMHUWRONXASJEL-UHFFFAOYSA-N n-[[3-(methanesulfonamido)phenyl]methyl]-2-phenylpyrimidine-5-carboxamide Chemical compound CS(=O)(=O)NC1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2C=CC=CC=2)=C1 JMHUWRONXASJEL-UHFFFAOYSA-N 0.000 claims description 4
• JRRRMJFMRDCDIQ-UHFFFAOYSA-N n-[[3-(methylsulfamoyl)phenyl]methyl]-2-pyridin-2-ylpyrimidine-5-carboxamide Chemical compound CNS(=O)(=O)C1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2N=CC=CC=2)=C1 JRRRMJFMRDCDIQ-UHFFFAOYSA-N 0.000 claims description 4
• VHEQYTMTTNZDND-UHFFFAOYSA-N n-[[3-[2-[di(propan-2-yl)amino]ethylsulfamoyl]phenyl]methyl]-2-(3-fluorophenyl)pyrimidine-5-carboxamide Chemical compound CC(C)N(C(C)C)CCNS(=O)(=O)C1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2C=C(F)C=CC=2)=C1 VHEQYTMTTNZDND-UHFFFAOYSA-N 0.000 claims description 4
• FMXRYQFMRGGKKX-UHFFFAOYSA-N n-[[4-(dimethylsulfamoyl)phenyl]methyl]-2-phenylpyrimidine-5-carboxamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1CNC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1 FMXRYQFMRGGKKX-UHFFFAOYSA-N 0.000 claims description 4
• CLIURAAZONMVBJ-UHFFFAOYSA-N n-[[4-(methylsulfamoyl)phenyl]methyl]-2-phenylpyrimidine-5-carboxamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1CNC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1 CLIURAAZONMVBJ-UHFFFAOYSA-N 0.000 claims description 4
• BWLPNCHALCXPLE-UHFFFAOYSA-N n-[[6-(dimethylamino)pyridin-3-yl]methyl]-2-phenylpyrimidine-5-carboxamide Chemical compound C1=NC(N(C)C)=CC=C1CNC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1 BWLPNCHALCXPLE-UHFFFAOYSA-N 0.000 claims description 4
• YPCIIIGVOPRGRW-UHFFFAOYSA-N n-benzyl-2-phenylpyrimidine-5-carboxamide Chemical compound C=1N=C(C=2C=CC=CC=2)N=CC=1C(=O)NCC1=CC=CC=C1 YPCIIIGVOPRGRW-UHFFFAOYSA-N 0.000 claims description 4
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
• UYGHNMQBWBFMFH-UHFFFAOYSA-N 2-(2,5-difluorophenyl)-n-[[3-(methylsulfamoyl)phenyl]methyl]pyrimidine-5-carboxamide Chemical compound CNS(=O)(=O)C1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2C(=CC=C(F)C=2)F)=C1 UYGHNMQBWBFMFH-UHFFFAOYSA-N 0.000 claims description 3
• XHISFJKGLCIDNI-UHFFFAOYSA-N 2-(3,5-difluorophenyl)-n-[[3-(methylsulfamoyl)phenyl]methyl]pyrimidine-5-carboxamide Chemical compound CNS(=O)(=O)C1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2C=C(F)C=C(F)C=2)=C1 XHISFJKGLCIDNI-UHFFFAOYSA-N 0.000 claims description 3
• SASJAUYABCWLAT-UHFFFAOYSA-N 2-(3-fluorophenyl)-4-methyl-n-[[2-(methylsulfamoyl)pyridin-4-yl]methyl]pyrimidine-5-carboxamide Chemical compound C1=NC(S(=O)(=O)NC)=CC(CNC(=O)C=2C(=NC(=NC=2)C=2C=C(F)C=CC=2)C)=C1 SASJAUYABCWLAT-UHFFFAOYSA-N 0.000 claims description 3
• WNRZAINOLZAVFD-UHFFFAOYSA-N 2-(3-fluorophenyl)-4-methyl-n-[[3-(methylsulfamoyl)phenyl]methyl]pyrimidine-5-carboxamide Chemical compound CNS(=O)(=O)C1=CC=CC(CNC(=O)C=2C(=NC(=NC=2)C=2C=C(F)C=CC=2)C)=C1 WNRZAINOLZAVFD-UHFFFAOYSA-N 0.000 claims description 3
• WYXDPWYXEMOUTL-UHFFFAOYSA-N 2-(3-fluorophenyl)-4-methyl-n-[[3-(propan-2-ylsulfamoylmethyl)phenyl]methyl]pyrimidine-5-carboxamide Chemical compound CC(C)NS(=O)(=O)CC1=CC=CC(CNC(=O)C=2C(=NC(=NC=2)C=2C=C(F)C=CC=2)C)=C1 WYXDPWYXEMOUTL-UHFFFAOYSA-N 0.000 claims description 3
• VQAMADLVRHLPNA-UHFFFAOYSA-N 2-(3-fluorophenyl)-4-methyl-n-[[5-(propan-2-ylsulfamoyl)pyridin-3-yl]methyl]pyrimidine-5-carboxamide Chemical compound CC(C)NS(=O)(=O)C1=CN=CC(CNC(=O)C=2C(=NC(=NC=2)C=2C=C(F)C=CC=2)C)=C1 VQAMADLVRHLPNA-UHFFFAOYSA-N 0.000 claims description 3
• NJPZIHDRWLSUDM-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-(2-pyrrolidin-1-ylsulfonylethyl)pyrimidine-5-carboxamide Chemical compound FC1=CC=CC(C=2N=CC(=CN=2)C(=O)NCCS(=O)(=O)N2CCCC2)=C1 NJPZIHDRWLSUDM-UHFFFAOYSA-N 0.000 claims description 3
• AIRAVOKVLAAGRU-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[(3-sulfamoylphenyl)methyl]pyrimidine-5-carboxamide Chemical compound NS(=O)(=O)C1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2C=C(F)C=CC=2)=C1 AIRAVOKVLAAGRU-UHFFFAOYSA-N 0.000 claims description 3
• HXCZMGZIWLVEJF-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[[2-(methylsulfamoyl)pyridin-4-yl]methyl]pyrimidine-5-carboxamide Chemical compound C1=NC(S(=O)(=O)NC)=CC(CNC(=O)C=2C=NC(=NC=2)C=2C=C(F)C=CC=2)=C1 HXCZMGZIWLVEJF-UHFFFAOYSA-N 0.000 claims description 3
• BAZQUWLDLRQTCT-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[[3-(2-methoxyethylsulfamoyl)phenyl]methyl]pyrimidine-5-carboxamide Chemical compound COCCNS(=O)(=O)C1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2C=C(F)C=CC=2)=C1 BAZQUWLDLRQTCT-UHFFFAOYSA-N 0.000 claims description 3
• DLEMPWCUBOMJKZ-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[[3-(2-methylpropylsulfamoyl)phenyl]methyl]pyrimidine-5-carboxamide Chemical compound CC(C)CNS(=O)(=O)C1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2C=C(F)C=CC=2)=C1 DLEMPWCUBOMJKZ-UHFFFAOYSA-N 0.000 claims description 3
• GPOYAQUQFHVJNG-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[[3-(2-morpholin-4-ylethylsulfamoyl)phenyl]methyl]pyrimidine-5-carboxamide Chemical compound FC1=CC=CC(C=2N=CC(=CN=2)C(=O)NCC=2C=C(C=CC=2)S(=O)(=O)NCCN2CCOCC2)=C1 GPOYAQUQFHVJNG-UHFFFAOYSA-N 0.000 claims description 3
• HEKWOFBFVRSAJF-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[[3-(2-piperidin-1-ylethylsulfamoyl)phenyl]methyl]pyrimidine-5-carboxamide Chemical compound FC1=CC=CC(C=2N=CC(=CN=2)C(=O)NCC=2C=C(C=CC=2)S(=O)(=O)NCCN2CCCCC2)=C1 HEKWOFBFVRSAJF-UHFFFAOYSA-N 0.000 claims description 3
• CGJXBDISGFTPNS-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[[3-(3-hydroxypropylsulfamoyl)phenyl]methyl]pyrimidine-5-carboxamide Chemical compound OCCCNS(=O)(=O)C1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2C=C(F)C=CC=2)=C1 CGJXBDISGFTPNS-UHFFFAOYSA-N 0.000 claims description 3
• FELIRFROLUXSTQ-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[[3-(4-hydroxybutylsulfamoyl)phenyl]methyl]pyrimidine-5-carboxamide Chemical compound OCCCCNS(=O)(=O)C1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2C=C(F)C=CC=2)=C1 FELIRFROLUXSTQ-UHFFFAOYSA-N 0.000 claims description 3
• PKFGWAPLEXBYSX-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[[3-(4-methoxybutylsulfamoyl)phenyl]methyl]pyrimidine-5-carboxamide Chemical compound COCCCCNS(=O)(=O)C1=CC=CC(CNC(=O)C=2C=NC(=NC=2)C=2C=C(F)C=CC=2)=C1 PKFGWAPLEXBYSX-UHFFFAOYSA-N 0.000 claims description 3
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