JP2002514195A

JP2002514195A - 置換ピリミジン化合物およびそれの使用

置換ピリミジン化合物およびそれの使用

Info

Publication number: JP2002514195A
Authority: JP; Japan
Prior art keywords: amino; alkyl; alkoxy; twenty; halogen
Prior art date: 1996-12-05
Legal status : Pending

Application number

JP52585098A

Other languages

English (en)

Japanese (ja)

Other versions

JP2002514195A5 (https=

Inventor

スポール、ウルリケ・デイー

マローネ，マイケル・ジエイ

マントロ，ネイサン・ビー

Original Assignee

アムジエン・インコーポレーテツド

Priority date

1996-12-05

Filing date

1997-12-04

Publication date

2002-05-14

1997-12-04 Application filed by アムジエン・インコーポレーテツド filed Critical アムジエン・インコーポレーテツド

2002-05-14 Publication of JP2002514195A publication Critical patent/JP2002514195A/ja

2005-05-12 Publication of JP2002514195A5 publication Critical patent/JP2002514195A5/ja

Status Pending legal-status Critical Current

Links

150000003230 pyrimidines Chemical class 0.000 title abstract description 13
-1 IL-1β Proteins 0.000 claims abstract description 439
150000001875 compounds Chemical class 0.000 claims abstract description 193
238000000034 method Methods 0.000 claims abstract description 133
108060008682 Tumor Necrosis Factor Proteins 0.000 claims abstract description 47
102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims abstract description 47
150000003839 salts Chemical class 0.000 claims abstract description 35
108090001007 Interleukin-8 Proteins 0.000 claims abstract description 27
108090001005 Interleukin-6 Proteins 0.000 claims abstract description 25
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 7
MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 claims abstract 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 301
229910052736 halogen Inorganic materials 0.000 claims description 245
150000002367 halogens Chemical class 0.000 claims description 241
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 162
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 151
125000001072 heteroaryl group Chemical group 0.000 claims description 137
125000000217 alkyl group Chemical group 0.000 claims description 129
125000000623 heterocyclic group Chemical group 0.000 claims description 117
125000003118 aryl group Chemical group 0.000 claims description 109
229910052739 hydrogen Inorganic materials 0.000 claims description 102
239000001257 hydrogen Substances 0.000 claims description 95
125000004093 cyano group Chemical group *C#N 0.000 claims description 93
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 89
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 87
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 84
239000000203 mixture Substances 0.000 claims description 76
125000001188 haloalkyl group Chemical group 0.000 claims description 66
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 63
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
125000004414 alkyl thio group Chemical group 0.000 claims description 45
125000003545 alkoxy group Chemical group 0.000 claims description 41
125000003282 alkyl amino group Chemical group 0.000 claims description 41
125000004663 dialkyl amino group Chemical group 0.000 claims description 40
125000005236 alkanoylamino group Chemical group 0.000 claims description 36
238000004519 manufacturing process Methods 0.000 claims description 36
229910052757 nitrogen Inorganic materials 0.000 claims description 36
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 35
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 35
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 33
229910052799 carbon Inorganic materials 0.000 claims description 33
125000000753 cycloalkyl group Chemical group 0.000 claims description 33
108010002352 Interleukin-1 Proteins 0.000 claims description 28
230000027455 binding Effects 0.000 claims description 23
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 23
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
229910052717 sulfur Inorganic materials 0.000 claims description 18
125000003710 aryl alkyl group Chemical group 0.000 claims description 16
125000005842 heteroatom Chemical group 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 15
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 14
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
241000124008 Mammalia Species 0.000 claims description 13
229960004666 glucagon Drugs 0.000 claims description 13
125000006492 halo alkyl aryl group Chemical group 0.000 claims description 12
125000002950 monocyclic group Chemical group 0.000 claims description 12
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 12
206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 11
208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 11
208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 11
201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
241000701022 Cytomegalovirus Species 0.000 claims description 10
102000051325 Glucagon Human genes 0.000 claims description 10
108060003199 Glucagon Proteins 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 10
230000006378 damage Effects 0.000 claims description 10
230000000694 effects Effects 0.000 claims description 10
MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 claims description 10
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 10
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 10
239000001301 oxygen Substances 0.000 claims description 10
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 9
206010061218 Inflammation Diseases 0.000 claims description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
230000004054 inflammatory process Effects 0.000 claims description 9
125000001624 naphthyl group Chemical group 0.000 claims description 9
206010039073 rheumatoid arthritis Diseases 0.000 claims description 9
229920006395 saturated elastomer Polymers 0.000 claims description 9
210000002237 B-cell of pancreatic islet Anatomy 0.000 claims description 8
206010028289 Muscle atrophy Diseases 0.000 claims description 8
206010040070 Septic Shock Diseases 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
125000003107 substituted aryl group Chemical group 0.000 claims description 8
239000011593 sulfur Substances 0.000 claims description 8
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 7
206010006895 Cachexia Diseases 0.000 claims description 7
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 7
201000004681 Psoriasis Diseases 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
150000001540 azides Chemical class 0.000 claims description 7
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 7
206010002198 Anaphylactic reaction Diseases 0.000 claims description 6
201000001320 Atherosclerosis Diseases 0.000 claims description 6
201000005569 Gout Diseases 0.000 claims description 6
206010018634 Gouty Arthritis Diseases 0.000 claims description 6
241001024304 Mino Species 0.000 claims description 6
102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 claims description 6
108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 claims description 6
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 claims description 6
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 claims description 6
206010063837 Reperfusion injury Diseases 0.000 claims description 6
206010040047 Sepsis Diseases 0.000 claims description 6
230000001154 acute effect Effects 0.000 claims description 6
230000036783 anaphylactic response Effects 0.000 claims description 6
208000003455 anaphylaxis Diseases 0.000 claims description 6
208000006673 asthma Diseases 0.000 claims description 6
125000002619 bicyclic group Chemical group 0.000 claims description 6
208000029028 brain injury Diseases 0.000 claims description 6
230000001684 chronic effect Effects 0.000 claims description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
201000008968 osteosarcoma Diseases 0.000 claims description 6
150000003180 prostaglandins Chemical class 0.000 claims description 6
230000036303 septic shock Effects 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000003396 thiol group Chemical class [H]S* 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
206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 5
206010063094 Cerebral malaria Diseases 0.000 claims description 5
206010009900 Colitis ulcerative Diseases 0.000 claims description 5
208000011231 Crohn disease Diseases 0.000 claims description 5
208000031886 HIV Infections Diseases 0.000 claims description 5
206010020164 HIV infection CDC Group III Diseases 0.000 claims description 5
241000713772 Human immunodeficiency virus 1 Species 0.000 claims description 5
241000713340 Human immunodeficiency virus 2 Species 0.000 claims description 5
241000257303 Hymenoptera Species 0.000 claims description 5
208000034578 Multiple myelomas Diseases 0.000 claims description 5
208000010191 Osteitis Deformans Diseases 0.000 claims description 5
208000001132 Osteoporosis Diseases 0.000 claims description 5
208000027868 Paget disease Diseases 0.000 claims description 5
206010035226 Plasma cell myeloma Diseases 0.000 claims description 5
206010037660 Pyrexia Diseases 0.000 claims description 5
208000033464 Reiter syndrome Diseases 0.000 claims description 5
206010039085 Rhinitis allergic Diseases 0.000 claims description 5
206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 5
201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
201000010105 allergic rhinitis Diseases 0.000 claims description 5
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
125000005418 aryl aryl group Chemical group 0.000 claims description 5
208000019664 bone resorption disease Diseases 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
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125000004475 heteroaralkyl group Chemical group 0.000 claims description 5
208000012947 ischemia reperfusion injury Diseases 0.000 claims description 5
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125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 5
201000008482 osteoarthritis Diseases 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
208000002574 reactive arthritis Diseases 0.000 claims description 5
208000011580 syndromic disease Diseases 0.000 claims description 5
241000701161 unidentified adenovirus Species 0.000 claims description 5
241001529453 unidentified herpesvirus Species 0.000 claims description 5
YYJDOTHPRUHPFR-IBGZPJMESA-N (2s)-1-n-[5-(3-chloro-4-fluorophenyl)-4-pyridin-4-ylpyrimidin-2-yl]-3-phenylpropane-1,2-diamine Chemical compound C([C@@H](N)CC=1C=CC=CC=1)NC(N=C1C=2C=CN=CC=2)=NC=C1C1=CC=C(F)C(Cl)=C1 YYJDOTHPRUHPFR-IBGZPJMESA-N 0.000 claims description 4
LRKOFWQOUAPPDT-NRFANRHFSA-N (2s)-3-phenyl-1-n-[4-pyridin-4-yl-5-[3-(trifluoromethyl)phenyl]pyrimidin-2-yl]propane-1,2-diamine Chemical compound C([C@@H](N)CC=1C=CC=CC=1)NC(N=C1C=2C=CN=CC=2)=NC=C1C1=CC=CC(C(F)(F)F)=C1 LRKOFWQOUAPPDT-NRFANRHFSA-N 0.000 claims description 4
YFPNLHNUUOEDCA-FQEVSTJZSA-N 2-[[(2s)-2-amino-3-phenylpropyl]amino]-5-(4-fluorophenyl)-6-pyridin-4-yl-1h-pyrimidin-4-one Chemical compound C([C@@H](N)CC=1C=CC=CC=1)NC(NC(=O)C=1C=2C=CC(F)=CC=2)=NC=1C1=CC=NC=C1 YFPNLHNUUOEDCA-FQEVSTJZSA-N 0.000 claims description 4
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
WAUSKYGFULPCPY-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-(2-phenylethyl)-4-pyridin-4-ylpyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C(C(=N1)C=2C=CN=CC=2)=CN=C1NCCC1=CC=CC=C1 WAUSKYGFULPCPY-UHFFFAOYSA-N 0.000 claims description 4
BGUNEQJBAXZMFT-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-[2-(2-fluorophenyl)ethyl]-4-pyridin-4-ylpyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C(C(=N1)C=2C=CN=CC=2)=CN=C1NCCC1=CC=CC=C1F BGUNEQJBAXZMFT-UHFFFAOYSA-N 0.000 claims description 4
MVEFUUAXUGCKDO-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-[2-(4-fluorophenyl)ethyl]-4-pyridin-4-ylpyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1CCNC(N=C1C=2C=CN=CC=2)=NC=C1C1=CC=C(F)C=C1 MVEFUUAXUGCKDO-UHFFFAOYSA-N 0.000 claims description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
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208000000112 Myalgia Diseases 0.000 claims description 4
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125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 4
208000015181 infectious disease Diseases 0.000 claims description 4
206010022000 influenza Diseases 0.000 claims description 4
208000010125 myocardial infarction Diseases 0.000 claims description 4
AEIYIQXHUVFPDN-UHFFFAOYSA-N n'-[5-(4-fluorophenyl)-4-pyridin-4-ylpyrimidin-2-yl]-n-phenylethane-1,2-diamine Chemical compound C1=CC(F)=CC=C1C(C(=N1)C=2C=CN=CC=2)=CN=C1NCCNC1=CC=CC=C1 AEIYIQXHUVFPDN-UHFFFAOYSA-N 0.000 claims description 4
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 4
229940094443 oxytocics prostaglandins Drugs 0.000 claims description 4
208000027753 pain disease Diseases 0.000 claims description 4
230000035939 shock Effects 0.000 claims description 4
125000000547 substituted alkyl group Chemical group 0.000 claims description 4
125000000464 thioxo group Chemical group S=* 0.000 claims description 4
DFJPVWXPUBOYIA-UZUQRXQVSA-N (1r,2r)-2-methyl-1-phenyl-n'-[4-pyridin-4-yl-5-[3-(trifluoromethyl)phenyl]pyrimidin-2-yl]propane-1,3-diamine Chemical compound C([C@@H](C)[C@@H](N)C=1C=CC=CC=1)NC(N=C1C=2C=CN=CC=2)=NC=C1C1=CC=CC(C(F)(F)F)=C1 DFJPVWXPUBOYIA-UZUQRXQVSA-N 0.000 claims description 3
OIYZGMOESXFTFS-VWLOTQADSA-N (2s)-1-n-(5-naphthalen-2-yl-4-pyridin-4-ylpyrimidin-2-yl)-3-phenylpropane-1,2-diamine Chemical compound C([C@@H](N)CC=1C=CC=CC=1)NC(N=1)=NC=C(C=2C=C3C=CC=CC3=CC=2)C=1C1=CC=NC=C1 OIYZGMOESXFTFS-VWLOTQADSA-N 0.000 claims description 3
XPMCPFMKOICLQX-QFIPXVFZSA-N (2s)-1-n-[5-(3-methylphenyl)-4-pyridin-4-ylpyrimidin-2-yl]-3-phenylpropane-1,2-diamine Chemical compound CC1=CC=CC(C=2C(=NC(NC[C@@H](N)CC=3C=CC=CC=3)=NC=2)C=2C=CN=CC=2)=C1 XPMCPFMKOICLQX-QFIPXVFZSA-N 0.000 claims description 3
BAMCVKIZRNLYJR-NRFANRHFSA-N (2s)-1-n-[5-(4-chlorophenyl)-4-pyridin-4-ylpyrimidin-2-yl]-3-phenylpropane-1,2-diamine Chemical compound C([C@@H](N)CC=1C=CC=CC=1)NC(N=C1C=2C=CN=CC=2)=NC=C1C1=CC=C(Cl)C=C1 BAMCVKIZRNLYJR-NRFANRHFSA-N 0.000 claims description 3
RNQWVOOLFRZKTH-UHFFFAOYSA-N 1-(2-fluorophenyl)-n'-[4-pyridin-4-yl-5-[3-(trifluoromethyl)phenyl]pyrimidin-2-yl]propane-1,3-diamine Chemical compound C=1C=CC=C(F)C=1C(N)CCNC(N=C1C=2C=CN=CC=2)=NC=C1C1=CC=CC(C(F)(F)F)=C1 RNQWVOOLFRZKTH-UHFFFAOYSA-N 0.000 claims description 3
DLUYDWMBZSEZCU-UHFFFAOYSA-N 2-[(2,6-dichlorophenyl)methyl]-5-(4-fluorophenyl)-4-pyridin-4-ylpyrimidine Chemical compound C1=CC(F)=CC=C1C(C(=N1)C=2C=CN=CC=2)=CN=C1CC1=C(Cl)C=CC=C1Cl DLUYDWMBZSEZCU-UHFFFAOYSA-N 0.000 claims description 3
HAOYRMOYPXUUBE-UHFFFAOYSA-N 2-[(2,6-dichlorophenyl)methyl]-5-(4-fluorophenyl)-6-pyridin-4-yl-1h-pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1C(C(N1)=O)=C(C=2C=CN=CC=2)N=C1CC1=C(Cl)C=CC=C1Cl HAOYRMOYPXUUBE-UHFFFAOYSA-N 0.000 claims description 3
PVRJMMJYIVUKPN-UHFFFAOYSA-N 2-methyl-1-n-[5-(3-methylphenyl)-4-pyridin-4-ylpyrimidin-2-yl]-3-phenylpropane-1,2-diamine Chemical compound CC1=CC=CC(C=2C(=NC(NCC(C)(N)CC=3C=CC=CC=3)=NC=2)C=2C=CN=CC=2)=C1 PVRJMMJYIVUKPN-UHFFFAOYSA-N 0.000 claims description 3
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IQTQTQWGNBHXGU-UHFFFAOYSA-N 5-(4-fluorophenyl)-2,4-dipyridin-4-ylpyrimidine Chemical compound C1=CC(F)=CC=C1C1=CN=C(C=2C=CN=CC=2)N=C1C1=CC=NC=C1 IQTQTQWGNBHXGU-UHFFFAOYSA-N 0.000 claims description 3
BRYBZPBPVDEMJR-UHFFFAOYSA-N 5-(4-fluorophenyl)-2-(4-phenylbutan-2-ylamino)-6-pyridin-4-yl-1h-pyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=C(C=2C=CC(F)=CC=2)C(=O)NC=1NC(C)CCC1=CC=CC=C1 BRYBZPBPVDEMJR-UHFFFAOYSA-N 0.000 claims description 3
HOPCLZFUVJYHMS-UHFFFAOYSA-N 5-(4-fluorophenyl)-4-pyridin-4-yl-2-thiophen-2-ylpyrimidine Chemical compound C1=CC(F)=CC=C1C1=CN=C(C=2SC=CC=2)N=C1C1=CC=NC=C1 HOPCLZFUVJYHMS-UHFFFAOYSA-N 0.000 claims description 3
HYLBZJAJPJJGPF-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-(2-morpholin-4-ylethyl)-4-pyridin-4-ylpyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C(C(=N1)C=2C=CN=CC=2)=CN=C1NCCN1CCOCC1 HYLBZJAJPJJGPF-UHFFFAOYSA-N 0.000 claims description 3
ZKPQAGXFGKQHDM-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-(2-piperidin-1-ylethyl)-4-pyridin-4-ylpyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C(C(=N1)C=2C=CN=CC=2)=CN=C1NCCN1CCCCC1 ZKPQAGXFGKQHDM-UHFFFAOYSA-N 0.000 claims description 3
QCANDZGZNIXHRH-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-(3-phenylpropyl)-4-pyridin-4-ylpyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C(C(=N1)C=2C=CN=CC=2)=CN=C1NCCCC1=CC=CC=C1 QCANDZGZNIXHRH-UHFFFAOYSA-N 0.000 claims description 3
USYITSDDXIKXSG-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-(4-phenylbutan-2-yl)-4-pyridin-4-ylpyrimidin-2-amine Chemical compound N=1C=C(C=2C=CC(F)=CC=2)C(C=2C=CN=CC=2)=NC=1NC(C)CCC1=CC=CC=C1 USYITSDDXIKXSG-UHFFFAOYSA-N 0.000 claims description 3
MVXWNCISMXKKFT-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-(4-phenylbutyl)-4-pyridin-4-ylpyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C(C(=N1)C=2C=CN=CC=2)=CN=C1NCCCCC1=CC=CC=C1 MVXWNCISMXKKFT-UHFFFAOYSA-N 0.000 claims description 3
GCJQPTUOPLERKD-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-[2-(3-methoxyphenyl)ethyl]-4-pyridin-4-ylpyrimidin-2-amine Chemical compound COC1=CC=CC(CCNC=2N=C(C(C=3C=CC(F)=CC=3)=CN=2)C=2C=CN=CC=2)=C1 GCJQPTUOPLERKD-UHFFFAOYSA-N 0.000 claims description 3
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