JP2011518192A5 - - Google Patents
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- JP2011518192A5 JP2011518192A5 JP2011505260A JP2011505260A JP2011518192A5 JP 2011518192 A5 JP2011518192 A5 JP 2011518192A5 JP 2011505260 A JP2011505260 A JP 2011505260A JP 2011505260 A JP2011505260 A JP 2011505260A JP 2011518192 A5 JP2011518192 A5 JP 2011518192A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- groups
- acyl
- hydrogen
- aryl
- Prior art date
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 181
- 125000002252 acyl group Chemical group 0.000 claims description 92
- -1 tautomer Substances 0.000 claims description 90
- 229910052739 hydrogen Inorganic materials 0.000 claims description 84
- 239000001257 hydrogen Substances 0.000 claims description 84
- 230000003287 optical effect Effects 0.000 claims description 83
- 150000003839 salts Chemical class 0.000 claims description 83
- 239000012453 solvate Substances 0.000 claims description 74
- 125000003118 aryl group Chemical group 0.000 claims description 69
- 125000004423 acyloxy group Chemical group 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 63
- 229910019142 PO4 Inorganic materials 0.000 claims description 59
- 238000006467 substitution reaction Methods 0.000 claims description 59
- 239000010452 phosphate Substances 0.000 claims description 58
- 125000003545 alkoxy group Chemical group 0.000 claims description 57
- 125000004104 aryloxy group Chemical group 0.000 claims description 57
- 125000003282 alkyl amino group Chemical group 0.000 claims description 56
- 125000001769 aryl amino group Chemical group 0.000 claims description 56
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 55
- 125000000304 alkynyl group Chemical group 0.000 claims description 52
- 150000001408 amides Chemical class 0.000 claims description 52
- 125000003342 alkenyl group Chemical group 0.000 claims description 51
- 125000005843 halogen group Chemical group 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 51
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 51
- 150000002431 hydrogen Chemical class 0.000 claims description 45
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 39
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 26
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 26
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 26
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 26
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 26
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 24
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 23
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 23
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 23
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 18
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 18
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 15
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 14
- 238000001727 in vivo Methods 0.000 claims description 14
- 229940002612 prodrug Drugs 0.000 claims description 14
- 239000000651 prodrug Substances 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 125000005035 acylthio group Chemical group 0.000 claims description 11
- 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 11
- 125000005108 alkenylthio group Chemical group 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000005139 alkynylsulfonyl group Chemical group 0.000 claims description 11
- 125000005109 alkynylthio group Chemical group 0.000 claims description 11
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 11
- 125000005110 aryl thio group Chemical group 0.000 claims description 11
- 125000003441 thioacyl group Chemical group 0.000 claims description 11
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 9
- 230000002757 inflammatory effect Effects 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000005136 alkenylsulfinyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 5
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
- 125000005134 alkynylsulfinyl group Chemical group 0.000 claims description 3
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical group [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 235000021317 phosphate Nutrition 0.000 claims 23
- 125000003368 amide group Chemical group 0.000 claims 8
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims 6
- 241000277306 Esocidae Species 0.000 claims 2
- 241001024304 Mino Species 0.000 claims 2
- 125000005549 heteroarylene group Chemical group 0.000 claims 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 150000001345 alkine derivatives Chemical class 0.000 description 7
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- SHGAZHPCJJPHSC-ZVCIMWCZSA-N 9-cis-retinoic acid Chemical compound OC(=O)/C=C(\C)/C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-ZVCIMWCZSA-N 0.000 description 2
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