BG65128B1

BG65128B1 - Заместени пирамидинови съединения и тяхното използване

Заместени пирамидинови съединения и тяхното използване Download PDF

Info

Publication number: BG65128B1
Authority: BG; Bulgaria
Prior art keywords: amino; alkyl; radicals; pyridyl; alkoxy
Prior art date: 1996-12-05

Application number

BG103512A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG103512A (en

Inventor

Ulrike Spohr

Michael Malone

Nathan Mantlo

Original Assignee

Amgen Inc.

Priority date

1996-12-05

Filing date

1999-06-22

Publication date

2007-03-30

1999-06-22 Application filed by Amgen Inc. filed Critical Amgen Inc.

2000-07-31 Publication of BG103512A publication Critical patent/BG103512A/xx

2007-03-30 Publication of BG65128B1 publication Critical patent/BG65128B1/bg

Links

CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 91
-1 IL-beta Proteins 0.000 claims abstract description 1898
150000001875 compounds Chemical class 0.000 claims abstract description 148
238000002360 preparation method Methods 0.000 claims abstract description 64
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 36
201000010099 disease Diseases 0.000 claims abstract description 31
238000011282 treatment Methods 0.000 claims abstract description 27
150000003839 salts Chemical class 0.000 claims abstract description 25
108090001007 Interleukin-8 Proteins 0.000 claims abstract description 24
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
230000002265 prevention Effects 0.000 claims abstract description 15
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 12
108090001005 Interleukin-6 Proteins 0.000 claims abstract 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 257
150000003254 radicals Chemical class 0.000 claims description 225
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 150
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 137
125000003118 aryl group Chemical group 0.000 claims description 134
125000005843 halogen group Chemical group 0.000 claims description 119
125000003545 alkoxy group Chemical group 0.000 claims description 118
125000000217 alkyl group Chemical group 0.000 claims description 116
150000001412 amines Chemical class 0.000 claims description 77
229910052736 halogen Inorganic materials 0.000 claims description 77
125000000623 heterocyclic group Chemical group 0.000 claims description 71
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 65
125000004414 alkyl thio group Chemical group 0.000 claims description 64
125000004093 cyano group Chemical group *C#N 0.000 claims description 60
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 59
125000005236 alkanoylamino group Chemical group 0.000 claims description 51
125000001072 heteroaryl group Chemical group 0.000 claims description 50
150000002367 halogens Chemical class 0.000 claims description 48
125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 47
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
229910052739 hydrogen Inorganic materials 0.000 claims description 44
239000001257 hydrogen Substances 0.000 claims description 43
125000001188 haloalkyl group Chemical group 0.000 claims description 40
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 39
125000003282 alkyl amino group Chemical group 0.000 claims description 38
YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 37
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
239000003814 drug Substances 0.000 claims description 34
125000000753 cycloalkyl group Chemical group 0.000 claims description 33
238000006243 chemical reaction Methods 0.000 claims description 32
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 29
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 26
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 25
108010002352 Interleukin-1 Proteins 0.000 claims description 24
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 23
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 23
125000003277 amino group Chemical group 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 23
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
125000004663 dialkyl amino group Chemical group 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 18
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 17
230000000694 effects Effects 0.000 claims description 16
229960004666 glucagon Drugs 0.000 claims description 16
229910052717 sulfur Inorganic materials 0.000 claims description 16
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 15
150000005840 aryl radicals Chemical class 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 15
230000004054 inflammatory process Effects 0.000 claims description 14
102000051325 Glucagon Human genes 0.000 claims description 13
108060003199 Glucagon Proteins 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
241000701022 Cytomegalovirus Species 0.000 claims description 12
206010061218 Inflammation Diseases 0.000 claims description 12
206010040070 Septic Shock Diseases 0.000 claims description 12
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 12
125000002950 monocyclic group Chemical group 0.000 claims description 11
241000124008 Mammalia Species 0.000 claims description 10
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 10
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
102000004190 Enzymes Human genes 0.000 claims description 9
108090000790 Enzymes Proteins 0.000 claims description 9
125000005842 heteroatom 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
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 8
206010006895 Cachexia Diseases 0.000 claims description 8
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 8
150000003230 pyrimidines Chemical class 0.000 claims description 8
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 7
102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 claims description 7
201000004681 Psoriasis Diseases 0.000 claims description 7
208000004756 Respiratory Insufficiency Diseases 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
230000001154 acute effect Effects 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
201000004193 respiratory failure Diseases 0.000 claims description 7
208000011580 syndromic disease Diseases 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 6
206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 6
210000002237 B-cell of pancreatic islet Anatomy 0.000 claims description 6
201000005569 Gout Diseases 0.000 claims description 6
206010020164 HIV infection CDC Group III Diseases 0.000 claims description 6
206010028289 Muscle atrophy Diseases 0.000 claims description 6
108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 claims description 6
208000033464 Reiter syndrome Diseases 0.000 claims description 6
206010040047 Sepsis Diseases 0.000 claims description 6
206010044248 Toxic shock syndrome Diseases 0.000 claims description 6
231100000650 Toxic shock syndrome Toxicity 0.000 claims description 6
201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
208000006673 asthma Diseases 0.000 claims description 6
150000001555 benzenes Chemical class 0.000 claims description 6
208000029028 brain injury Diseases 0.000 claims description 6
125000001589 carboacyl group Chemical group 0.000 claims description 6
201000006417 multiple sclerosis Diseases 0.000 claims description 6
201000008482 osteoarthritis Diseases 0.000 claims description 6
150000003180 prostaglandins Chemical class 0.000 claims description 6
208000002574 reactive arthritis Diseases 0.000 claims description 6
230000036303 septic shock Effects 0.000 claims description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
206010002198 Anaphylactic reaction Diseases 0.000 claims description 5
201000001320 Atherosclerosis Diseases 0.000 claims description 5
206010063094 Cerebral malaria Diseases 0.000 claims description 5
206010012442 Dermatitis contact Diseases 0.000 claims description 5
206010018634 Gouty Arthritis Diseases 0.000 claims description 5
208000031886 HIV Infections Diseases 0.000 claims description 5
208000007514 Herpes zoster 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
208000034578 Multiple myelomas Diseases 0.000 claims description 5
208000000112 Myalgia 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
206010046851 Uveitis Diseases 0.000 claims description 5
230000036783 anaphylactic response Effects 0.000 claims description 5
208000003455 anaphylaxis Diseases 0.000 claims description 5
208000010247 contact dermatitis Diseases 0.000 claims description 5
230000006378 damage Effects 0.000 claims description 5
208000015181 infectious disease Diseases 0.000 claims description 5
230000000302 ischemic effect Effects 0.000 claims description 5
208000027202 mammary Paget disease Diseases 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
150000003573 thiols Chemical class 0.000 claims description 5
241000701161 unidentified adenovirus Species 0.000 claims description 5
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 4
SLXNJBBOHVEGJT-UHFFFAOYSA-N 3-[[5-(3-methylphenyl)-4-pyridin-4-ylpyrimidin-2-yl]amino]-1-phenylpropan-1-ol Chemical compound CC1=CC=CC(C=2C(=NC(NCCC(O)C=3C=CC=CC=3)=NC=2)C=2C=CN=CC=2)=C1 SLXNJBBOHVEGJT-UHFFFAOYSA-N 0.000 claims description 4
KCCJWVIEGXBNAL-UHFFFAOYSA-N 4-[2-[[5-(4-fluorophenyl)-4-pyridin-4-ylpyrimidin-2-yl]amino]ethyl]phenol Chemical compound C1=CC(O)=CC=C1CCNC(N=C1C=2C=CN=CC=2)=NC=C1C1=CC=C(F)C=C1 KCCJWVIEGXBNAL-UHFFFAOYSA-N 0.000 claims description 4
RGIZQHDYGJLOHC-UHFFFAOYSA-N 5-(4-fluorophenyl)-2-piperazin-1-yl-4-pyridin-4-ylpyrimidine Chemical compound C1=CC(F)=CC=C1C1=CN=C(N2CCNCC2)N=C1C1=CC=NC=C1 RGIZQHDYGJLOHC-UHFFFAOYSA-N 0.000 claims description 4
208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 4
208000024827 Alzheimer disease Diseases 0.000 claims description 4
208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 4
208000006386 Bone Resorption Diseases 0.000 claims description 4
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 4
208000011231 Crohn disease Diseases 0.000 claims description 4
208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 4
208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 4
206010037660 Pyrexia Diseases 0.000 claims description 4
206010039085 Rhinitis allergic Diseases 0.000 claims description 4
208000006011 Stroke Diseases 0.000 claims description 4
150000001350 alkyl halides Chemical class 0.000 claims description 4
201000010105 allergic rhinitis Diseases 0.000 claims description 4
230000024279 bone resorption Effects 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
150000004656 dimethylamines Chemical class 0.000 claims description 4
208000035475 disorder Diseases 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
206010022000 influenza Diseases 0.000 claims description 4
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 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
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 4
230000004044 response Effects 0.000 claims description 4
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
CEPNYRGGEXJJAW-NRFANRHFSA-N (2s)-1-n-[5-(1-benzothiophen-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=2SC3=CC=CC=C3C=2)C=1C1=CC=NC=C1 CEPNYRGGEXJJAW-NRFANRHFSA-N 0.000 claims description 3
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 3
YOKPLKHJAZTBIF-NRFANRHFSA-N (2s)-1-n-[5-(3-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=CC(F)=C1 YOKPLKHJAZTBIF-NRFANRHFSA-N 0.000 claims description 3
IZTKLEPLPSFFRZ-UHFFFAOYSA-N 1-phenyl-n'-[4-pyridin-4-yl-5-[3-(trifluoromethyl)phenyl]pyrimidin-2-yl]propane-1,3-diamine Chemical compound C=1C=CC=CC=1C(N)CCNC(N=C1C=2C=CN=CC=2)=NC=C1C1=CC=CC(C(F)(F)F)=C1 IZTKLEPLPSFFRZ-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
NTIJEFXEWKCOHB-QHCPKHFHSA-N 2-[(3s)-3-benzylpiperazin-1-yl]-4-pyridin-4-yl-5-[3-(trifluoromethyl)phenyl]pyrimidine Chemical compound FC(F)(F)C1=CC=CC(C=2C(=NC(=NC=2)N2C[C@H](CC=3C=CC=CC=3)NCC2)C=2C=CN=CC=2)=C1 NTIJEFXEWKCOHB-QHCPKHFHSA-N 0.000 claims description 3
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 3
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 3
DTNJCGSDISUMCI-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-4-pyridin-4-ylpyrimidin-2-yl]-2-methyl-1,3-thiazole Chemical compound S1C(C)=NC(C=2N=C(C(C=3C=CC(F)=CC=3)=CN=2)C=2C=CN=CC=2)=C1 DTNJCGSDISUMCI-UHFFFAOYSA-N 0.000 claims description 3
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
NGPPAWIEXQPCQA-UHFFFAOYSA-N 5-(4-fluorophenyl)-4-pyridin-4-yl-2-pyrrolidin-1-ylpyrimidine Chemical compound C1=CC(F)=CC=C1C1=CN=C(N2CCCC2)N=C1C1=CC=NC=C1 NGPPAWIEXQPCQA-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
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 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
YVHODILVEWBIDZ-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-[3-(1h-imidazol-2-yl)propyl]-4-pyridin-4-ylpyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C(C(=N1)C=2C=CN=CC=2)=CN=C1NCCCC1=NC=CN1 YVHODILVEWBIDZ-UHFFFAOYSA-N 0.000 claims description 3
206010063837 Reperfusion injury Diseases 0.000 claims description 3
239000005557 antagonist Substances 0.000 claims description 3
125000002619 bicyclic group Chemical group 0.000 claims description 3
230000008993 bowel inflammation Effects 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
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