JP2010540438A5 - - Google Patents

Info

Publication number

JP2010540438A5

JP2010540438A5 JP2010525834A JP2010525834A JP2010540438A5 JP 2010540438 A5 JP2010540438 A5 JP 2010540438A5 JP 2010525834 A JP2010525834 A JP 2010525834A JP 2010525834 A JP2010525834 A JP 2010525834A JP 2010540438 A5 JP2010540438 A5 JP 2010540438A5

Authority

JP

Japan

Prior art keywords

alk

haloalk

phenyl

heteroaryl

compound

Prior art date

2008-09-19

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Pending

Links

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• 239000000203 mixture Substances 0.000 claims description 142
• 150000001875 compounds Chemical class 0.000 claims description 141
• 229910052799 carbon Inorganic materials 0.000 claims description 54
• 125000001072 heteroaryl group Chemical group 0.000 claims description 50
• 239000003814 drug Substances 0.000 claims description 48
• 229910052736 halogen Inorganic materials 0.000 claims description 48
• 150000002367 halogens Chemical class 0.000 claims description 48
• 229910052739 hydrogen Inorganic materials 0.000 claims description 48
• -1 1H-tetrazol-5-yl Chemical group 0.000 claims description 44
• 229910052717 sulfur Inorganic materials 0.000 claims description 44
• 239000001257 hydrogen Substances 0.000 claims description 42
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
• 125000001424 substituent group Chemical group 0.000 claims description 36
• 229910052760 oxygen Inorganic materials 0.000 claims description 35
• 229910052794 bromium Inorganic materials 0.000 claims description 34
• 229910052801 chlorine Inorganic materials 0.000 claims description 34
• 229910052731 fluorine Inorganic materials 0.000 claims description 34
• 125000003118 aryl group Chemical group 0.000 claims description 32
• 238000002360 preparation method Methods 0.000 claims description 31
• 238000011282 treatment Methods 0.000 claims description 29
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
• 150000003839 salts Chemical class 0.000 claims description 20
• 239000003937 drug carrier Substances 0.000 claims description 19
• 206010052779 Transplant rejections Diseases 0.000 claims description 16
• 125000005842 heteroatom Chemical group 0.000 claims description 15
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• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
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• 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 8
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 210000004738 parenchymal cell Anatomy 0.000 claims description 7
• 125000001769 aryl amino group Chemical group 0.000 claims description 6
• 210000004153 islets of langerhan Anatomy 0.000 claims description 6
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• 125000005241 heteroarylamino group Chemical group 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 238000006467 substitution reaction Methods 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 2
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• 238000009472 formulation Methods 0.000 description 40
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• 230000000694 effects Effects 0.000 description 33
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
• 239000002904 solvent Substances 0.000 description 28
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
• 150000002431 hydrogen Chemical class 0.000 description 27
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• 238000002347 injection Methods 0.000 description 18
• 239000007924 injection Substances 0.000 description 18
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• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
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• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
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• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
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• 125000000304 alkynyl group Chemical group 0.000 description 10
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• 239000008273 gelatin Substances 0.000 description 10
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• 235000011852 gelatine desserts Nutrition 0.000 description 10
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• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
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• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 125000003342 alkenyl group Chemical group 0.000 description 9
• 238000003556 assay Methods 0.000 description 9
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• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 8
• 229920002261 Corn starch Polymers 0.000 description 8
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• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 7
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