BG65128B1 - Заместени пирамидинови съединения и тяхното използване - Google Patents
Заместени пирамидинови съединения и тяхното използване Download PDFInfo
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- BG65128B1 BG65128B1 BG103512A BG10351299A BG65128B1 BG 65128 B1 BG65128 B1 BG 65128B1 BG 103512 A BG103512 A BG 103512A BG 10351299 A BG10351299 A BG 10351299A BG 65128 B1 BG65128 B1 BG 65128B1
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- Prior art keywords
- amino
- alkyl
- radicals
- pyridyl
- alkoxy
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- 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
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- 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
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- 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
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- 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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US3212896P | 1996-12-05 | 1996-12-05 | |
US5095097P | 1997-06-13 | 1997-06-13 | |
US97605497A | 1997-11-21 | 1997-11-21 |
Publications (2)
Publication Number | Publication Date |
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BG103512A BG103512A (en) | 2000-07-31 |
BG65128B1 true BG65128B1 (bg) | 2007-03-30 |
Family
ID=27364030
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BG103512A BG65128B1 (bg) | 1996-12-05 | 1999-06-22 | Заместени пирамидинови съединения и тяхното използване |
Country Status (11)
Country | Link |
---|---|
EP (1) | EP0948497A2 (cs) |
CN (1) | CN1246858A (cs) |
AR (1) | AR048564A1 (cs) |
AU (1) | AU733877C (cs) |
BG (1) | BG65128B1 (cs) |
BR (1) | BR9713850A (cs) |
CA (1) | CA2274063C (cs) |
CZ (1) | CZ296911B6 (cs) |
HU (1) | HUP0001698A3 (cs) |
IL (1) | IL130180A0 (cs) |
NZ (1) | NZ335997A (cs) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100860827B1 (ko) * | 2000-09-06 | 2008-09-30 | 노바티스 백신즈 앤드 다이아그노스틱스 인코포레이티드 | 글리코겐 합성효소 키나아제 3의 억제제 |
DE60231414D1 (de) | 2001-09-21 | 2009-04-16 | Braband Friedrich Wilhelm | 3-substituierte 4-pyrimidonderivate |
DK1427709T3 (da) | 2001-09-21 | 2006-04-03 | Mitsubishi Pharma Corp | 3-substituerede 4-pyrimidonderivater |
TWI330183B (cs) * | 2001-10-22 | 2010-09-11 | Eisai R&D Man Co Ltd | |
EP1340759A1 (en) * | 2002-02-28 | 2003-09-03 | Sanofi-Synthelabo | 1-[alkyl], 1-[(heteroaryl)alkyl] and 1-[(aryl)alkyl]-7-(pyrimidin-4-yl)-imidazo[1,2-a]pyrimidin-5(1H)-one derivatives |
CA2510170C (en) | 2002-12-16 | 2011-05-24 | Mitsubishi Pharma Corporation | 3-substituted-4-pyrimidone derivatives |
TWI357408B (en) | 2003-03-26 | 2012-02-01 | Mitsubishi Tanabe Pharma Corp | 3-substituted-4-pyrimidone derivatives |
MX337179B (es) * | 2010-10-18 | 2016-02-15 | Cerenis Therapeutics Holding Sa | Compuestos, composiciones y metodos utiles para la movilizacion de colesterol. |
TWI651310B (zh) * | 2014-02-20 | 2019-02-21 | 日商日本煙草產業股份有限公司 | 三化合物及其醫藥用途 |
KR102649802B1 (ko) * | 2015-10-29 | 2024-03-20 | 아스카 세이야쿠 가부시키가이샤 | 피리미딘 유도체 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE759176A (fr) * | 1969-11-20 | 1971-05-19 | Sandoz Sa | Derives de la pyrimidine, leur preparation et medicaments contenant cesderives |
US4438117A (en) * | 1980-09-03 | 1984-03-20 | E. I. Du Pont De Nemours And Company | 2-Substituted thio-4,5-diarylpyrimidines |
DE3319843A1 (de) * | 1983-06-01 | 1984-12-06 | Ali-Akbar Dipl.-Chem. Dr. 4300 Mülheim Pourzal | Verfahren zur herstellung von pyrimidinen aus nitrilen und alkinen |
US4500533A (en) * | 1983-06-22 | 1985-02-19 | Eli Lilly And Company | 2,4,5-Triaryl pyrimidines and a method of treating pain, fever, thrombosis, inflammation and arthritis |
US5077142A (en) * | 1989-04-20 | 1991-12-31 | Ricoh Company, Ltd. | Electroluminescent devices |
US5620999A (en) * | 1994-07-28 | 1997-04-15 | Weier; Richard M. | Benzenesulfonamide subtituted imidazolyl compounds for the treatment of inflammation |
-
1997
- 1997-12-04 CZ CZ0201599A patent/CZ296911B6/cs not_active IP Right Cessation
- 1997-12-04 CA CA002274063A patent/CA2274063C/en not_active Expired - Fee Related
- 1997-12-04 CN CN97181563A patent/CN1246858A/zh active Pending
- 1997-12-04 AU AU60120/98A patent/AU733877C/en not_active Ceased
- 1997-12-04 AR ARP970105689A patent/AR048564A1/es not_active Application Discontinuation
- 1997-12-04 HU HU0001698A patent/HUP0001698A3/hu unknown
- 1997-12-04 NZ NZ335997A patent/NZ335997A/xx unknown
- 1997-12-04 IL IL13018097A patent/IL130180A0/xx unknown
- 1997-12-04 BR BR9713850-9A patent/BR9713850A/pt not_active Application Discontinuation
- 1997-12-04 EP EP97954778A patent/EP0948497A2/en not_active Withdrawn
-
1999
- 1999-06-22 BG BG103512A patent/BG65128B1/bg unknown
Also Published As
Publication number | Publication date |
---|---|
EP0948497A2 (en) | 1999-10-13 |
BR9713850A (pt) | 2000-02-29 |
CA2274063A1 (en) | 1998-06-11 |
AU733877C (en) | 2003-05-08 |
CZ296911B6 (cs) | 2006-07-12 |
NZ335997A (en) | 2001-08-31 |
AU6012098A (en) | 1998-06-29 |
AU733877B2 (en) | 2001-05-31 |
BG103512A (en) | 2000-07-31 |
HUP0001698A2 (hu) | 2001-04-28 |
CA2274063C (en) | 2007-09-04 |
HUP0001698A3 (en) | 2002-07-29 |
AR048564A1 (es) | 2006-05-10 |
IL130180A0 (en) | 2000-06-01 |
CZ9902015A3 (cs) | 1999-11-17 |
CN1246858A (zh) | 2000-03-08 |
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