RU2420519C2 - Пиримидинамидные соединения как ингибиторы pgds - Google Patents

Info

Publication number

RU2420519C2

RU2420519C2 RU2008117170/04A RU2008117170A RU2420519C2 RU 2420519 C2 RU2420519 C2 RU 2420519C2 RU 2008117170/04 A RU2008117170/04 A RU 2008117170/04A RU 2008117170 A RU2008117170 A RU 2008117170A RU 2420519 C2 RU2420519 C2 RU 2420519C2

Authority

RU

Russia

Prior art keywords

carboxylic acid

pyrimidine

fluorophenyl

phenylpyrimidine

amide

Prior art date

2005-10-04

Links

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• Global Dossier
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• 239000003112 inhibitor Substances 0.000 title description 7
• 101150020741 Hpgds gene 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 Chemical group 0.000 claims abstract description 244
• 150000001875 compounds Chemical class 0.000 claims abstract description 116
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 90
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 87
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 82
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 76
• 150000003839 salts Chemical class 0.000 claims abstract description 68
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 64
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 64
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 61
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 55
• 125000003118 aryl group Chemical group 0.000 claims abstract description 54
• 150000002367 halogens Chemical class 0.000 claims abstract description 53
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 43
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 40
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 37
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 30
• 239000001257 hydrogen Substances 0.000 claims abstract description 25
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 23
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 23
• 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 23
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 23
• 239000001301 oxygen Substances 0.000 claims abstract description 23
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 19
• 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 16
• 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 11
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims abstract description 7
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 6
• 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims abstract description 5
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract description 4
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
• 150000002431 hydrogen Chemical class 0.000 claims abstract 5
• 125000003831 tetrazolyl group Chemical group 0.000 claims abstract 2
• 125000001424 substituent group Chemical group 0.000 claims description 52
• 229910052717 sulfur Chemical group 0.000 claims description 45
• 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 30
• 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 27
• 239000011593 sulfur Chemical group 0.000 claims description 22
• 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 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 150000001408 amides Chemical class 0.000 claims description 13
• 125000002883 imidazolyl group Chemical group 0.000 claims description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• AHVQYHFYQWKUKB-UHFFFAOYSA-N oxan-4-amine Chemical compound NC1CCOCC1 AHVQYHFYQWKUKB-UHFFFAOYSA-N 0.000 claims description 9
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 8
• 125000003386 piperidinyl group Chemical group 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 8
• FMVLDCBNRZZNPH-UHFFFAOYSA-N 3-(aminomethyl)-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(CN)=C1 FMVLDCBNRZZNPH-UHFFFAOYSA-N 0.000 claims description 7
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 7
• OYAHSBDYBOBAAQ-UHFFFAOYSA-N 3-phenyl-1,2,4-thiadiazol-5-amine Chemical compound S1C(N)=NC(C=2C=CC=CC=2)=N1 OYAHSBDYBOBAAQ-UHFFFAOYSA-N 0.000 claims description 7
• 125000000335 thiazolyl group Chemical group 0.000 claims description 7
• 102000048176 Prostaglandin-D synthases Human genes 0.000 claims description 6
• 108030003866 Prostaglandin-D synthases Proteins 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• POAYTBQJGDPYTN-UHFFFAOYSA-N ethyl 4-methyl-2-[(2-phenylpyrimidine-5-carbonyl)amino]-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OCC)SC(NC(=O)C=2C=NC(=NC=2)C=2C=CC=CC=2)=N1 POAYTBQJGDPYTN-UHFFFAOYSA-N 0.000 claims description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• 125000001544 thienyl group Chemical group 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
• 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 5
• WNAVSKJKDPLWBD-UHFFFAOYSA-N 4-[(4-aminophenyl)methyl]-1,3-oxazolidin-2-one Chemical compound C1=CC(N)=CC=C1CC1NC(=O)OC1 WNAVSKJKDPLWBD-UHFFFAOYSA-N 0.000 claims description 5
• QGPXRYILXGJZLQ-UHFFFAOYSA-N CC(C)S(NCC1=CC=CC(CN)=C1)(=O)=O.CC1=NC(C2=CC(F)=CC=C2)=NC=C1C(O)=O Chemical compound CC(C)S(NCC1=CC=CC(CN)=C1)(=O)=O.CC1=NC(C2=CC(F)=CC=C2)=NC=C1C(O)=O QGPXRYILXGJZLQ-UHFFFAOYSA-N 0.000 claims description 5
• PNUFAGWBCNLWHU-UHFFFAOYSA-N CN(S(=O)(=O)CCC1=NC(=NC=C1C(=O)N)C1=CC=CC=C1)C Chemical compound CN(S(=O)(=O)CCC1=NC(=NC=C1C(=O)N)C1=CC=CC=C1)C PNUFAGWBCNLWHU-UHFFFAOYSA-N 0.000 claims description 5
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• HQXWLMHDYYSCOQ-UHFFFAOYSA-N methyl 6-[(2-phenylpyrimidine-5-carbonyl)amino]-1h-benzimidazole-2-carboxylate Chemical compound C1=C2NC(C(=O)OC)=NC2=CC=C1NC(=O)C(C=N1)=CN=C1C1=CC=CC=C1 HQXWLMHDYYSCOQ-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
• YFFOPYRVSFTEKX-UHFFFAOYSA-N 1-cyclohexyl-3-[(sulfamoylamino)methyl]benzene 2-(3-fluorophenyl)pyrimidine-5-carboxylic acid Chemical compound N1=CC(C(=O)O)=CN=C1C1=CC=CC(F)=C1.NS(=O)(=O)NCC1=CC=CC(C2CCCCC2)=C1 YFFOPYRVSFTEKX-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• AFIQCJGNOINCFJ-UHFFFAOYSA-N 2-(2-fluorophenyl)-n-phenylpyrimidine-5-carboxamide Chemical compound FC1=CC=CC=C1C1=NC=C(C(=O)NC=2C=CC=CC=2)C=N1 AFIQCJGNOINCFJ-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 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 4
• 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 4
• ORJYDEDAGKXIFL-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-phenylpyrimidine-5-carboxamide Chemical compound FC1=CC=CC(C=2N=CC(=CN=2)C(=O)NC=2C=CC=CC=2)=C1 ORJYDEDAGKXIFL-UHFFFAOYSA-N 0.000 claims description 4
• NPVIMKMVCZZRCG-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-phenylpyrimidine-5-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC=C(C(=O)NC=2C=CC=CC=2)C=N1 NPVIMKMVCZZRCG-UHFFFAOYSA-N 0.000 claims description 4
• RWMORAFKNKQOES-UHFFFAOYSA-N 2-[2-[(2-phenylpyrimidine-5-carbonyl)amino]-1,3-thiazol-4-yl]acetic acid Chemical compound OC(=O)CC1=CSC(NC(=O)C=2C=NC(=NC=2)C=2C=CC=CC=2)=N1 RWMORAFKNKQOES-UHFFFAOYSA-N 0.000 claims description 4
• KCGMHUJQPCHRQG-UHFFFAOYSA-N 2-cyclohexyl-n-phenylpyrimidine-5-carboxamide Chemical compound C=1N=C(C2CCCCC2)N=CC=1C(=O)NC1=CC=CC=C1 KCGMHUJQPCHRQG-UHFFFAOYSA-N 0.000 claims description 4
• JLMZQOWMYYLDAN-UHFFFAOYSA-N 2-phenyl-n-(1,3-thiazol-2-yl)pyrimidine-5-carboxamide Chemical compound C=1N=C(C=2C=CC=CC=2)N=CC=1C(=O)NC1=NC=CS1 JLMZQOWMYYLDAN-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
• XZUYMDLVCBBIBJ-UHFFFAOYSA-N 2-phenyl-n-pyridin-2-ylpyrimidine-5-carboxamide Chemical compound C=1N=C(C=2C=CC=CC=2)N=CC=1C(=O)NC1=CC=CC=N1 XZUYMDLVCBBIBJ-UHFFFAOYSA-N 0.000 claims description 4
• FSBIAEYLUOBHLG-UHFFFAOYSA-N 2-phenylpyrimidine-5-carboxamide Chemical compound N1=CC(C(=O)N)=CN=C1C1=CC=CC=C1 FSBIAEYLUOBHLG-UHFFFAOYSA-N 0.000 claims description 4
• BDZAKJITXGLLPO-UHFFFAOYSA-N 4-methyl-2-[(2-phenylpyrimidine-5-carbonyl)amino]-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(O)=O)=C(C)N=C1NC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1 BDZAKJITXGLLPO-UHFFFAOYSA-N 0.000 claims description 4
• VSHUWCDFDWUCLV-UHFFFAOYSA-N 4-methyl-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)C)=C1 VSHUWCDFDWUCLV-UHFFFAOYSA-N 0.000 claims description 4
• NHSBFQSDZXJQFL-UHFFFAOYSA-N 4-methyl-n-[[3-(methylsulfamoyl)phenyl]methyl]-2-pyridin-3-ylpyrimidine-5-carboxamide Chemical compound CNS(=O)(=O)C1=CC=CC(CNC(=O)C=2C(=NC(=NC=2)C=2C=NC=CC=2)C)=C1 NHSBFQSDZXJQFL-UHFFFAOYSA-N 0.000 claims description 4
• SBMKVOMWVWBYCZ-UHFFFAOYSA-N 6-[(2-phenylpyrimidine-5-carbonyl)amino]-1h-benzimidazole-2-carboxylic acid Chemical compound C1=C2NC(C(=O)O)=NC2=CC=C1NC(=O)C(C=N1)=CN=C1C1=CC=CC=C1 SBMKVOMWVWBYCZ-UHFFFAOYSA-N 0.000 claims description 4
• XKPUAMADWYXWMQ-UHFFFAOYSA-N CC(C)(CO)NS(C1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O Chemical compound CC(C)(CO)NS(C1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O XKPUAMADWYXWMQ-UHFFFAOYSA-N 0.000 claims description 4
• KJQBMNQCJPDFKD-UHFFFAOYSA-N CC(C)N(CCNS(C1=CC=CC(CN)=C1)(=O)=O)C(C)C.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O Chemical compound CC(C)N(CCNS(C1=CC=CC(CN)=C1)(=O)=O)C(C)C.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O KJQBMNQCJPDFKD-UHFFFAOYSA-N 0.000 claims description 4
• PEHXALGTCBNCNK-UHFFFAOYSA-N CCN(CC)CCNS(C1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O Chemical compound CCN(CC)CCNS(C1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O PEHXALGTCBNCNK-UHFFFAOYSA-N 0.000 claims description 4
• OHKVMUKIAHHHPF-UHFFFAOYSA-N CCN1C(CNS(C2=CC=CC(CN)=C2)(=O)=O)CCC1.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O Chemical compound CCN1C(CNS(C2=CC=CC(CN)=C2)(=O)=O)CCC1.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O OHKVMUKIAHHHPF-UHFFFAOYSA-N 0.000 claims description 4
• MYRLWNISPOMNRG-UHFFFAOYSA-N CCOCCNS(C1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O Chemical compound CCOCCNS(C1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O MYRLWNISPOMNRG-UHFFFAOYSA-N 0.000 claims description 4
• SNDYGWNJVHIJJQ-UHFFFAOYSA-N CN(C)CCCCCNS(C1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O Chemical compound CN(C)CCCCCNS(C1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O SNDYGWNJVHIJJQ-UHFFFAOYSA-N 0.000 claims description 4
• IEEVROFTZZCJCJ-UHFFFAOYSA-N CN(C)CCNS(C1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O Chemical compound CN(C)CCNS(C1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O IEEVROFTZZCJCJ-UHFFFAOYSA-N 0.000 claims description 4
• IORPFGWAYQRRMV-UHFFFAOYSA-N COCCCCNS(C1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O Chemical compound COCCCCNS(C1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O IORPFGWAYQRRMV-UHFFFAOYSA-N 0.000 claims description 4
• AREOLAOGFFWVGK-UHFFFAOYSA-N COCCCNS(C1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O Chemical compound COCCCNS(C1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O AREOLAOGFFWVGK-UHFFFAOYSA-N 0.000 claims description 4
• SKXHHZKDSRKNIH-UHFFFAOYSA-N COCCNS(C1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O Chemical compound COCCNS(C1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O SKXHHZKDSRKNIH-UHFFFAOYSA-N 0.000 claims description 4
• WUKMCCYMNVEMLE-UHFFFAOYSA-N CS(NCC1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O Chemical compound CS(NCC1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O WUKMCCYMNVEMLE-UHFFFAOYSA-N 0.000 claims description 4
• HGKSBJKEDBNJJX-UHFFFAOYSA-N NCC1=CC(S(N2CCOCC2)(=O)=O)=CC=C1.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O Chemical compound NCC1=CC(S(N2CCOCC2)(=O)=O)=CC=C1.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O HGKSBJKEDBNJJX-UHFFFAOYSA-N 0.000 claims description 4
• JKLWPYDWSVADQZ-UHFFFAOYSA-N NCC1=CC(S(NCCCO)(=O)=O)=CC=C1.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O Chemical compound NCC1=CC(S(NCCCO)(=O)=O)=CC=C1.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O JKLWPYDWSVADQZ-UHFFFAOYSA-N 0.000 claims description 4
• NSWYGCOSMLGLJC-UHFFFAOYSA-N NCC1=CC=CC=C1.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O Chemical compound NCC1=CC=CC=C1.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O NSWYGCOSMLGLJC-UHFFFAOYSA-N 0.000 claims description 4
• 125000005872 benzooxazolyl group Chemical group 0.000 claims description 4
• AYBYSKMPYHOYNK-UHFFFAOYSA-N ethyl 2-[2-[(2-phenylpyrimidine-5-carbonyl)amino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NC(=O)C=2C=NC(=NC=2)C=2C=CC=CC=2)=N1 AYBYSKMPYHOYNK-UHFFFAOYSA-N 0.000 claims description 4
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 claims description 4
• GDMRKZXEQGKMHO-UHFFFAOYSA-N n-(4-diethoxyphosphorylbutyl)-2-phenylpyrimidine-5-carboxamide Chemical compound N1=CC(C(=O)NCCCCP(=O)(OCC)OCC)=CN=C1C1=CC=CC=C1 GDMRKZXEQGKMHO-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• LPFBPRBNBAXHJV-UHFFFAOYSA-N n-[(4-carbamoylphenyl)methyl]-2-phenylpyrimidine-5-carboxamide Chemical compound C1=CC(C(=O)N)=CC=C1CNC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1 LPFBPRBNBAXHJV-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
• WJIBFJGHHNLCRV-UHFFFAOYSA-N n-[4-(aminomethyl)pyridin-2-yl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC(CN)=CC=N1 WJIBFJGHHNLCRV-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
• CYYKXHBGGOAQAZ-UHFFFAOYSA-N n-[[3-(cyclopropylsulfamoyl)phenyl]methyl]-2-(3-fluorophenyl)pyrimidine-5-carboxamide Chemical compound FC1=CC=CC(C=2N=CC(=CN=2)C(=O)NCC=2C=C(C=CC=2)S(=O)(=O)NC2CC2)=C1 CYYKXHBGGOAQAZ-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
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