TW201016707A - Oxazolopyrimidines as Edg-1 receptor agonists - Google Patents

Info

Publication number

TW201016707A

TW201016707A TW098123561A TW98123561A TW201016707A TW 201016707 A TW201016707 A TW 201016707A TW 098123561 A TW098123561 A TW 098123561A TW 98123561 A TW98123561 A TW 98123561A TW 201016707 A TW201016707 A TW 201016707A

Authority

TW

Taiwan

Prior art keywords

group

alkyl

ring

crc4

phenyl

Prior art date

2008-07-15

Links

• Espacenet
• Global Dossier
• Discuss

• 102100025750 Sphingosine 1-phosphate receptor 1 Human genes 0.000 title abstract description 10
• 101000693265 Homo sapiens Sphingosine 1-phosphate receptor 1 Proteins 0.000 title abstract description 9
• BRIOKNPDCPJCOD-UHFFFAOYSA-N [1,3]oxazolo[5,4-d]pyrimidine Chemical class N1=CN=C2OC=NC2=C1 BRIOKNPDCPJCOD-UHFFFAOYSA-N 0.000 title abstract description 5
• 239000000018 receptor agonist Substances 0.000 title description 4
• 229940044601 receptor agonist Drugs 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 322
• 238000000034 method Methods 0.000 claims abstract description 90
• 239000003814 drug Substances 0.000 claims abstract description 18
• 238000002360 preparation method Methods 0.000 claims abstract description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 10
• 206010019280 Heart failures Diseases 0.000 claims abstract description 9
• 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims abstract description 7
• -1 cyano, Hydroxycarbonyl Chemical group 0.000 claims description 431
• 125000001424 substituent group Chemical group 0.000 claims description 405
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 182
• 229910052736 halogen Inorganic materials 0.000 claims description 165
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 155
• 125000000217 alkyl group Chemical group 0.000 claims description 151
• 150000002367 halogens Chemical class 0.000 claims description 150
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 133
• 150000001412 amines Chemical class 0.000 claims description 131
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 130
• 125000004432 carbon atom Chemical group C* 0.000 claims description 122
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 117
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 110
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 101
• 125000003277 amino group Chemical group 0.000 claims description 91
• 229910052757 nitrogen Inorganic materials 0.000 claims description 89
• 239000000203 mixture Substances 0.000 claims description 83
• 150000003839 salts Chemical class 0.000 claims description 82
• 229920006395 saturated elastomer Polymers 0.000 claims description 79
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 76
• 125000005842 heteroatom Chemical group 0.000 claims description 63
• 125000000623 heterocyclic group Chemical group 0.000 claims description 62
• 125000003118 aryl group Chemical group 0.000 claims description 61
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 60
• 239000011737 fluorine Substances 0.000 claims description 60
• 229910052731 fluorine Inorganic materials 0.000 claims description 60
• 125000002950 monocyclic group Chemical group 0.000 claims description 60
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 58
• 125000004434 sulfur atom Chemical group 0.000 claims description 58
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 52
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 51
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 50
• 125000002619 bicyclic group Chemical group 0.000 claims description 49
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 47
• 229910052799 carbon Inorganic materials 0.000 claims description 45
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 45
• 239000012453 solvate Substances 0.000 claims description 42
• 150000001721 carbon Chemical group 0.000 claims description 41
• 125000004429 atom Chemical group 0.000 claims description 40
• 229910052739 hydrogen Inorganic materials 0.000 claims description 39
• 239000001257 hydrogen Substances 0.000 claims description 39
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 37
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 36
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
• 238000006467 substitution reaction Methods 0.000 claims description 32
• 229910052760 oxygen Inorganic materials 0.000 claims description 31
• 239000001301 oxygen Substances 0.000 claims description 31
• 239000007789 gas Substances 0.000 claims description 26
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
• 125000003545 alkoxy group Chemical group 0.000 claims description 23
• 125000005843 halogen group Chemical group 0.000 claims description 23
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 22
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 21
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 21
• 229910052707 ruthenium Inorganic materials 0.000 claims description 21
• 229910052717 sulfur Inorganic materials 0.000 claims description 19
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• 206010028980 Neoplasm Diseases 0.000 claims description 16
• 239000002253 acid Substances 0.000 claims description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• 125000001153 fluoro group Chemical group F* 0.000 claims description 15
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 14
• 125000004122 cyclic group Chemical group 0.000 claims description 14
• 125000000524 functional group Chemical group 0.000 claims description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
• 201000011510 cancer Diseases 0.000 claims description 12
• 150000003254 radicals Chemical class 0.000 claims description 12
• 125000003342 alkenyl group Chemical group 0.000 claims description 10
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 9
• 125000001624 naphthyl group Chemical group 0.000 claims description 9
• 229910052762 osmium Inorganic materials 0.000 claims description 9
• SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
• 229910052786 argon Inorganic materials 0.000 claims description 8
• 239000000126 substance Substances 0.000 claims description 8
• 230000008728 vascular permeability Effects 0.000 claims description 8
• 239000000654 additive Substances 0.000 claims description 7
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
• 125000003282 alkyl amino group Chemical group 0.000 claims description 7
• 229940079593 drug Drugs 0.000 claims description 7
• 125000002541 furyl group Chemical group 0.000 claims description 7
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 206010036790 Productive cough Diseases 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 206010012601 diabetes mellitus Diseases 0.000 claims description 6
• 210000003734 kidney Anatomy 0.000 claims description 6
• 208000017169 kidney disease Diseases 0.000 claims description 6
• 208000024794 sputum Diseases 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 5
• 230000006378 damage Effects 0.000 claims description 5
• 208000027866 inflammatory disease Diseases 0.000 claims description 5
• 229910052747 lanthanoid Inorganic materials 0.000 claims description 5
• 150000002602 lanthanoids Chemical class 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 5
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• 208000023504 respiratory system disease Diseases 0.000 claims description 5
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• 208000023275 Autoimmune disease Diseases 0.000 claims description 4
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• 208000027418 Wounds and injury Diseases 0.000 claims description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
• 208000029078 coronary artery disease Diseases 0.000 claims description 4
• 229910052805 deuterium Inorganic materials 0.000 claims description 4
• 208000014674 injury Diseases 0.000 claims description 4
• 208000010125 myocardial infarction Diseases 0.000 claims description 4
• 206010002383 Angina Pectoris Diseases 0.000 claims description 3
• 206010030113 Oedema Diseases 0.000 claims description 3
• 230000000996 additive effect Effects 0.000 claims description 3
• 150000001408 amides Chemical class 0.000 claims description 3
• 230000033115 angiogenesis Effects 0.000 claims description 3
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 3
• 230000035479 physiological effects, processes and functions Effects 0.000 claims description 3
• 208000037803 restenosis Diseases 0.000 claims description 3
• GQXURJDNDYACGE-UHFFFAOYSA-N 1-hydroxycyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(O)CC1 GQXURJDNDYACGE-UHFFFAOYSA-N 0.000 claims description 2
• 208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 2
• 208000002249 Diabetes Complications Diseases 0.000 claims description 2
• 208000032781 Diabetic cardiomyopathy Diseases 0.000 claims description 2
• 206010048554 Endothelial dysfunction Diseases 0.000 claims description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
• 206010040047 Sepsis Diseases 0.000 claims description 2
• 208000006011 Stroke Diseases 0.000 claims description 2
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• 230000002159 abnormal effect Effects 0.000 claims description 2
• 230000037429 base substitution Effects 0.000 claims description 2
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
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• 241000219112 Cucumis Species 0.000 claims 2
• 235000015510 Cucumis melo subsp melo Nutrition 0.000 claims 2
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 2
• KKJUPNGICOCCDW-UHFFFAOYSA-N 7-N,N-Dimethylamino-1,2,3,4,5-pentathiocyclooctane Chemical compound CN(C)C1CSSSSSC1 KKJUPNGICOCCDW-UHFFFAOYSA-N 0.000 claims 1
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• 208000034189 Sclerosis Diseases 0.000 claims 1
• FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims 1
• 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims 1
• HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims 1
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• DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 1
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