RU2604062C2 - ПРОИЗВОДНЫЕ ПИРАЗОЛО[1,5-a]ПИРИМИДИНА И ТИЕНО[3,2-b]ПИРИМИДИНА В КАЧЕСТВЕ МОДУЛЯТОРОВ IRAK-4 - Google Patents

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Publication number

RU2604062C2

RU2604062C2 RU2013103539/04A RU2013103539A RU2604062C2 RU 2604062 C2 RU2604062 C2 RU 2604062C2 RU 2013103539/04 A RU2013103539/04 A RU 2013103539/04A RU 2013103539 A RU2013103539 A RU 2013103539A RU 2604062 C2 RU2604062 C2 RU 2604062C2

Authority

RU

Russia

Prior art keywords

hydroxy

phenyl

chloro

amide

amino

Prior art date

2010-07-13

Links

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• 102100023533 Interleukin-1 receptor-associated kinase 4 Human genes 0.000 title abstract description 10
• 101710199010 Interleukin-1 receptor-associated kinase 4 Proteins 0.000 title abstract description 9
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 2
• LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 title 1
• 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
• 239000000203 mixture Substances 0.000 claims abstract description 244
• 150000001875 compounds Chemical class 0.000 claims abstract description 92
• 230000002757 inflammatory effect Effects 0.000 claims abstract description 9
• 239000003814 drug Substances 0.000 claims abstract description 7
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 7
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 6
• 230000001363 autoimmune Effects 0.000 claims abstract description 6
• -1 hydroxy, amino Chemical group 0.000 claims description 793
• 125000000217 alkyl group Chemical group 0.000 claims description 193
• 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 173
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 135
• 125000003545 alkoxy group Chemical group 0.000 claims description 123
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 66
• 125000003386 piperidinyl group Chemical group 0.000 claims description 64
• 229910052739 hydrogen Inorganic materials 0.000 claims description 51
• 239000001257 hydrogen Substances 0.000 claims description 51
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 46
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
• 125000003342 alkenyl group Chemical group 0.000 claims description 26
• 125000004193 piperazinyl group Chemical group 0.000 claims description 25
• 229910052736 halogen Inorganic materials 0.000 claims description 23
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 22
• 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 22
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 22
• 150000002367 halogens Chemical class 0.000 claims description 22
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
• 125000003725 azepanyl group Chemical group 0.000 claims description 21
• 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 21
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 20
• 150000001408 amides Chemical class 0.000 claims description 17
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 13
• 125000004414 alkyl thio 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
• 125000002757 morpholinyl group Chemical group 0.000 claims description 13
• 125000002971 oxazolyl group Chemical group 0.000 claims description 13
• 238000011282 treatment Methods 0.000 claims description 13
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 12
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 10
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 10
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
• KHQQFZLUDBLSCR-UHFFFAOYSA-N N-[5-chloro-2-(4-hydroxycyclohexyl)oxyphenyl]-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OC1CCC(CC1)O KHQQFZLUDBLSCR-UHFFFAOYSA-N 0.000 claims description 8
• 208000006673 asthma Diseases 0.000 claims description 8
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 6
• OKAAFIKHHROVHN-UHFFFAOYSA-N 6-bromopyrazolo[1,5-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(Br)C=NC2=C(C(=O)O)C=NN21 OKAAFIKHHROVHN-UHFFFAOYSA-N 0.000 claims description 5
• YNSSRWJHTRRYLL-UHFFFAOYSA-N N-[2-[4-(aminomethyl)piperidin-1-yl]-5-chlorophenyl]-2H-pyrimidine-1-carboxamide Chemical compound C1CC(CN)CCN1C1=CC=C(Cl)C=C1NC(=O)N1C=CC=NC1 YNSSRWJHTRRYLL-UHFFFAOYSA-N 0.000 claims description 5
• NLNGTEGRUVLYBX-UHFFFAOYSA-N 2h-pyrimidine-1,4-dicarboxylic acid Chemical compound OC(=O)N1CN=C(C(O)=O)C=C1 NLNGTEGRUVLYBX-UHFFFAOYSA-N 0.000 claims description 4
• CSOYDALHEQEMAK-UHFFFAOYSA-N 2h-pyrimidine-1-carboxylic acid Chemical compound OC(=O)N1CN=CC=C1 CSOYDALHEQEMAK-UHFFFAOYSA-N 0.000 claims description 4
• 125000001246 bromo group Chemical group Br* 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 208000009079 Bronchial Spasm Diseases 0.000 claims description 3
• 208000014181 Bronchial disease Diseases 0.000 claims description 3
• 206010006482 Bronchospasm Diseases 0.000 claims description 3
• IABLBDLMCQDMBV-UHFFFAOYSA-N N-(5-chloro-2-piperidin-1-ylphenyl)-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C1)NC(=O)N1CN=CC=C1)N1CCCCC1 IABLBDLMCQDMBV-UHFFFAOYSA-N 0.000 claims description 3
• HXHLZEHIILHFHN-UHFFFAOYSA-N N-[5-chloro-2-(2,3-dihydroxypropoxy)phenyl]-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OCC(CO)O HXHLZEHIILHFHN-UHFFFAOYSA-N 0.000 claims description 3
• 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• NMWMSILCMHNULF-UHFFFAOYSA-N n-[5-chloro-2-(4-hydroxy-2-methylbutan-2-yl)oxyphenyl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound OCCC(C)(C)OC1=CC=C(Cl)C=C1NC(=O)C1=CSC2=CN=CN=C12 NMWMSILCMHNULF-UHFFFAOYSA-N 0.000 claims description 3
• WRORDPRTLRAARE-UHFFFAOYSA-N n-[5-chloro-2-[(4-methyl-1,3-oxazol-5-yl)methoxy]phenyl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N1=COC(COC=2C(=CC(Cl)=CC=2)NC(=O)C=2C3=NC=NC=C3SC=2)=C1C WRORDPRTLRAARE-UHFFFAOYSA-N 0.000 claims description 3
• RAIGSWRYTFZVQJ-UHFFFAOYSA-N n-[5-chloro-2-[4-(hydroxymethyl)piperidin-1-yl]phenyl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound C1CC(CO)CCN1C1=CC=C(Cl)C=C1NC(=O)C1=CSC2=CN=CN=C12 RAIGSWRYTFZVQJ-UHFFFAOYSA-N 0.000 claims description 3
• SWVJRCQTLUOVCN-UHFFFAOYSA-N C(C)C=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OC Chemical compound C(C)C=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OC SWVJRCQTLUOVCN-UHFFFAOYSA-N 0.000 claims description 2
• BXYPCUCWCDMUAB-UHFFFAOYSA-N COC1=C(C=C(C=C1)C)NC(=O)N1CN=CC=C1 Chemical compound COC1=C(C=C(C=C1)C)NC(=O)N1CN=CC=C1 BXYPCUCWCDMUAB-UHFFFAOYSA-N 0.000 claims description 2
• CYGJWTHMWINNRM-UHFFFAOYSA-N Cl.ClC=1C=CC(=C(C1)NC(=O)N1CN=CC=C1)OC1CCNCC1 Chemical compound Cl.ClC=1C=CC(=C(C1)NC(=O)N1CN=CC=C1)OC1CCNCC1 CYGJWTHMWINNRM-UHFFFAOYSA-N 0.000 claims description 2
• GHQWZTNVEILGIJ-UHFFFAOYSA-N Cl.NC(C)C1CN(CC1)C1=C(C=C(C=C1)Cl)NC(=O)N1CN=CC=C1 Chemical compound Cl.NC(C)C1CN(CC1)C1=C(C=C(C=C1)Cl)NC(=O)N1CN=CC=C1 GHQWZTNVEILGIJ-UHFFFAOYSA-N 0.000 claims description 2
• YKTYDDAHJDCDDC-UHFFFAOYSA-N ClC1=CC(=C(C=C1)C1=CC=C(C=C1)CO)NC(=O)N1CN=CC=C1 Chemical compound ClC1=CC(=C(C=C1)C1=CC=C(C=C1)CO)NC(=O)N1CN=CC=C1 YKTYDDAHJDCDDC-UHFFFAOYSA-N 0.000 claims description 2
• HIRNMXZCWWDBMF-UHFFFAOYSA-N ClC1=CC(=C(C=C1)C1=CC=C(C=C1)O)NC(=O)N1CN=CC=C1 Chemical compound ClC1=CC(=C(C=C1)C1=CC=C(C=C1)O)NC(=O)N1CN=CC=C1 HIRNMXZCWWDBMF-UHFFFAOYSA-N 0.000 claims description 2
• GRAJONPUKMZGOT-UHFFFAOYSA-N ClC1=CC(=C(C=C1)C1=CC=CC=C1)NC(=O)N1CN=CC=C1 Chemical compound ClC1=CC(=C(C=C1)C1=CC=CC=C1)NC(=O)N1CN=CC=C1 GRAJONPUKMZGOT-UHFFFAOYSA-N 0.000 claims description 2
• BVBZOMVGHMAKFY-UHFFFAOYSA-N ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)N1CC(CC1)O Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)N1CC(CC1)O BVBZOMVGHMAKFY-UHFFFAOYSA-N 0.000 claims description 2
• DWLJBSMVZPSGDZ-UHFFFAOYSA-N ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)N1CCOCC1 Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)N1CCOCC1 DWLJBSMVZPSGDZ-UHFFFAOYSA-N 0.000 claims description 2
• QJJHYGCRSQDVOU-UHFFFAOYSA-N ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OC(F)F Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OC(F)F QJJHYGCRSQDVOU-UHFFFAOYSA-N 0.000 claims description 2
• JFTAXQZLXAHLFM-UHFFFAOYSA-N ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OC1CC(CCC1)O Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OC1CC(CCC1)O JFTAXQZLXAHLFM-UHFFFAOYSA-N 0.000 claims description 2
• QIKXTLZJSYSATO-UHFFFAOYSA-N ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OCC1=C(N=CO1)C Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OCC1=C(N=CO1)C QIKXTLZJSYSATO-UHFFFAOYSA-N 0.000 claims description 2
• BVMQCMDBQFXFNL-UHFFFAOYSA-N ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OCCO Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OCCO BVMQCMDBQFXFNL-UHFFFAOYSA-N 0.000 claims description 2
• PIYBZZSSEMZXRZ-UHFFFAOYSA-N ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OCCOC Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OCCOC PIYBZZSSEMZXRZ-UHFFFAOYSA-N 0.000 claims description 2
• BEXFPKPGYNNVBB-UHFFFAOYSA-N ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)SC Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)SC BEXFPKPGYNNVBB-UHFFFAOYSA-N 0.000 claims description 2
• PBGFHCXYSGFSOE-UHFFFAOYSA-N N-(5-acetamido-2-methoxyphenyl)-2H-pyrimidine-1-carboxamide Chemical compound C(C)(=O)NC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OC PBGFHCXYSGFSOE-UHFFFAOYSA-N 0.000 claims description 2
• WIXLXFBNCAROTJ-UHFFFAOYSA-N N-(5-bromo-2-methoxyphenyl)-2H-pyrimidine-1-carboxamide Chemical compound BrC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OC WIXLXFBNCAROTJ-UHFFFAOYSA-N 0.000 claims description 2
• VIAQRSFFBKFJAB-UHFFFAOYSA-N N-(5-chloro-2-cyclohexylphenyl)-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)C1CCCCC1 VIAQRSFFBKFJAB-UHFFFAOYSA-N 0.000 claims description 2
• OWLASDDNWNYAKI-UHFFFAOYSA-N N-(5-chloro-2-ethylphenyl)-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)CC OWLASDDNWNYAKI-UHFFFAOYSA-N 0.000 claims description 2
• KBNXAWHMYUXGEW-UHFFFAOYSA-N N-(5-chloro-2-methoxyphenyl)-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OC KBNXAWHMYUXGEW-UHFFFAOYSA-N 0.000 claims description 2
• UEZBCAVEKIDTPV-UHFFFAOYSA-N N-(5-chloro-2-pyrrolidin-1-ylphenyl)-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)N1CCCC1 UEZBCAVEKIDTPV-UHFFFAOYSA-N 0.000 claims description 2
• UHHKLZQAWKRIFU-UHFFFAOYSA-N N-(5-ethenyl-2-methoxyphenyl)-2H-pyrimidine-1-carboxamide Chemical compound COC1=C(C=C(C=C1)C=C)NC(=O)N1CN=CC=C1 UHHKLZQAWKRIFU-UHFFFAOYSA-N 0.000 claims description 2
• UYPGXEQTFFJFEK-UHFFFAOYSA-N N-(5-fluoro-2-methoxyphenyl)-2H-pyrimidine-1-carboxamide Chemical compound FC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OC UYPGXEQTFFJFEK-UHFFFAOYSA-N 0.000 claims description 2
• GKWWIVHUHKSBSR-UHFFFAOYSA-N N-[2-(3-aminopyrrolidin-1-yl)-5-chlorophenyl]-2H-pyrimidine-1-carboxamide Chemical compound NC1CN(CC1)C1=C(C=C(C=C1)Cl)NC(=O)N1CN=CC=C1 GKWWIVHUHKSBSR-UHFFFAOYSA-N 0.000 claims description 2
• JKWSLYOZTLFZEG-UHFFFAOYSA-N N-[2-(4-aminopiperidin-1-yl)-5-chlorophenyl]-2H-pyrimidine-1-carboxamide Chemical compound C1CC(N)CCN1C1=CC=C(Cl)C=C1NC(=O)N1C=CC=NC1 JKWSLYOZTLFZEG-UHFFFAOYSA-N 0.000 claims description 2
• ZRLBHFOTIRAVKX-UHFFFAOYSA-N N-[2-(azepan-1-yl)-5-chlorophenyl]-2H-pyrimidine-1-carboxamide Chemical compound N1(CCCCCC1)C1=C(C=C(C=C1)Cl)NC(=O)N1CN=CC=C1 ZRLBHFOTIRAVKX-UHFFFAOYSA-N 0.000 claims description 2
• AXPFDGVEQJDSQV-UHFFFAOYSA-N N-[2-[3-(aminomethyl)pyrrolidin-1-yl]-5-chlorophenyl]-2H-pyrimidine-1-carboxamide Chemical compound NCC1CN(CC1)C1=C(C=C(C=C1)Cl)NC(=O)N1CN=CC=C1 AXPFDGVEQJDSQV-UHFFFAOYSA-N 0.000 claims description 2
• SLRVNQHPAHEGOZ-UHFFFAOYSA-N N-[2-[4-(aminomethyl)phenyl]-5-chlorophenyl]-2H-pyrimidine-1-carboxamide Chemical compound C1=CC(CN)=CC=C1C1=CC=C(Cl)C=C1NC(=O)N1C=CC=NC1 SLRVNQHPAHEGOZ-UHFFFAOYSA-N 0.000 claims description 2
• WGHLXMHYLSDIDI-UHFFFAOYSA-N N-[5-(hydroxymethyl)-2-piperidin-1-ylphenyl]-2H-pyrimidine-1-carboxamide Chemical compound OCC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)N1CCCCC1 WGHLXMHYLSDIDI-UHFFFAOYSA-N 0.000 claims description 2
• WWIYLIQDDFFKPW-UHFFFAOYSA-N N-[5-chloro-2-(1,3-oxazol-5-ylmethoxy)phenyl]-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OCC1=CN=CO1 WWIYLIQDDFFKPW-UHFFFAOYSA-N 0.000 claims description 2
• ANQIJSPPWDUIGX-UHFFFAOYSA-N N-[5-chloro-2-(2-methylpropoxy)phenyl]-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OCC(C)C ANQIJSPPWDUIGX-UHFFFAOYSA-N 0.000 claims description 2
• WPNWGHSGQAFJRX-UHFFFAOYSA-N N-[5-chloro-2-(3,4-dihydroxybutoxy)phenyl]-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OCCC(CO)O WPNWGHSGQAFJRX-UHFFFAOYSA-N 0.000 claims description 2
• SAGALGWMZKMNIE-UHFFFAOYSA-N N-[5-chloro-2-(3-hydroxycyclopentyl)oxyphenyl]-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OC1CC(CC1)O SAGALGWMZKMNIE-UHFFFAOYSA-N 0.000 claims description 2
• SSQCTAKADIEAAD-UHFFFAOYSA-N N-[5-chloro-2-(3-hydroxypiperidin-1-yl)phenyl]-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)N1CC(CCC1)O SSQCTAKADIEAAD-UHFFFAOYSA-N 0.000 claims description 2
• JUGFBOJZVPMGHH-UHFFFAOYSA-N N-[5-chloro-2-(3-hydroxypropoxy)phenyl]-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OCCCO JUGFBOJZVPMGHH-UHFFFAOYSA-N 0.000 claims description 2
• ZDXCQQXBVUQNOJ-UHFFFAOYSA-N N-[5-chloro-2-(3-methoxypropoxy)phenyl]-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OCCCOC ZDXCQQXBVUQNOJ-UHFFFAOYSA-N 0.000 claims description 2
• XXZFZSBBNGYWPF-UHFFFAOYSA-N N-[5-chloro-2-(4-hydroxybutoxy)phenyl]-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OCCCCO XXZFZSBBNGYWPF-UHFFFAOYSA-N 0.000 claims description 2
• IOXDHPAOXNHTCB-UHFFFAOYSA-N N-[5-chloro-2-(4-hydroxybutyl)phenyl]-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)CCCCO IOXDHPAOXNHTCB-UHFFFAOYSA-N 0.000 claims description 2
• FZZPRIRBQSINHR-UHFFFAOYSA-N N-[5-chloro-2-(4-hydroxypiperidin-1-yl)phenyl]-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)N1CCC(CC1)O FZZPRIRBQSINHR-UHFFFAOYSA-N 0.000 claims description 2
• WDQLHENJOVTMPH-UHFFFAOYSA-N N-[5-chloro-2-(4-methylpiperazin-1-yl)phenyl]-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)N1CCN(CC1)C WDQLHENJOVTMPH-UHFFFAOYSA-N 0.000 claims description 2
• PCDGEZRBAKSDAW-UHFFFAOYSA-N N-[5-chloro-2-[(3-hydroxyphenyl)methoxy]phenyl]-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OCC1=CC(=CC=C1)O PCDGEZRBAKSDAW-UHFFFAOYSA-N 0.000 claims description 2
• IZWNDERLLMMUDF-UHFFFAOYSA-N N-[5-chloro-2-[2-(hydroxymethyl)piperidin-1-yl]phenyl]-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)N1C(CCCC1)CO IZWNDERLLMMUDF-UHFFFAOYSA-N 0.000 claims description 2
• FEQOIQVLCYKDKM-UHFFFAOYSA-N N-[5-chloro-2-[2-hydroxyethyl(methyl)amino]phenyl]-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)N(C)CCO FEQOIQVLCYKDKM-UHFFFAOYSA-N 0.000 claims description 2
• PMLZVNRPAOSQHJ-UHFFFAOYSA-N N-[5-chloro-2-[3-(hydroxymethyl)cyclopentyl]oxyphenyl]-2H-pyrimidine-1-carboxamide Chemical compound ClC=1C=CC(=C(C=1)NC(=O)N1CN=CC=C1)OC1CC(CC1)CO PMLZVNRPAOSQHJ-UHFFFAOYSA-N 0.000 claims description 2
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