OA12771A - Substituted pyridinones as modulators of P38 map kinase. - Google Patents
Substituted pyridinones as modulators of P38 map kinase. Download PDFInfo
- Publication number
- OA12771A OA12771A OA1200400210A OA1200400210A OA12771A OA 12771 A OA12771 A OA 12771A OA 1200400210 A OA1200400210 A OA 1200400210A OA 1200400210 A OA1200400210 A OA 1200400210A OA 12771 A OA12771 A OA 12771A
- Authority
- OA
- OAPI
- Prior art keywords
- alkyl
- oxy
- methyl
- pyridin
- bromo
- Prior art date
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- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 title abstract description 18
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 title abstract description 18
- 150000005299 pyridinones Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 215
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 24
- 201000010099 disease Diseases 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 1674
- 125000003545 alkoxy group Chemical group 0.000 claims description 510
- 229910052736 halogen Inorganic materials 0.000 claims description 489
- 150000002367 halogens Chemical class 0.000 claims description 488
- -1 -0S02-aryl Chemical group 0.000 claims description 325
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 261
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 249
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 224
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 202
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 158
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 153
- 125000001188 haloalkyl group Chemical group 0.000 claims description 134
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 132
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 95
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 89
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 87
- 125000004193 piperazinyl group Chemical group 0.000 claims description 87
- 229910052757 nitrogen Inorganic materials 0.000 claims description 82
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 78
- 125000004076 pyridyl group Chemical group 0.000 claims description 78
- 229910052739 hydrogen Inorganic materials 0.000 claims description 74
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 73
- 239000001257 hydrogen Substances 0.000 claims description 70
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 69
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 67
- 125000002757 morpholinyl group Chemical group 0.000 claims description 67
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 63
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 61
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 58
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 57
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 56
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 54
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 53
- 125000003386 piperidinyl group Chemical group 0.000 claims description 52
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 48
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 46
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 46
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- 125000003373 pyrazinyl group Chemical group 0.000 claims description 43
- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 41
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 41
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 41
- 125000001041 indolyl group Chemical group 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 35
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 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 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 125000000304 alkynyl group Chemical group 0.000 claims description 27
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
- 125000003282 alkyl amino group Chemical group 0.000 claims description 25
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 25
- 125000001544 thienyl group Chemical group 0.000 claims description 25
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 24
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 20
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 20
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 20
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 20
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- 125000004103 aminoalkyl group Chemical group 0.000 claims description 19
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 19
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 19
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 18
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- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
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- 125000002883 imidazolyl group Chemical group 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 12
- 125000004104 aryloxy group Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 12
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 12
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- 206010028980 Neoplasm Diseases 0.000 claims description 11
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 10
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
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- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 2
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-
2003
- 2003-02-14 PL PL371943A patent/PL218749B1/pl unknown
- 2003-02-14 DK DK03713478T patent/DK1490064T3/da active
- 2003-02-14 JP JP2003567412A patent/JP4164031B2/ja not_active Expired - Fee Related
- 2003-02-14 NZ NZ534395A patent/NZ534395A/en not_active IP Right Cessation
- 2003-02-14 SI SI200331709T patent/SI1490064T1/sl unknown
- 2003-02-14 PT PT03713478T patent/PT1490064E/pt unknown
- 2003-02-14 AT AT03713478T patent/ATE448784T1/de active
- 2003-02-14 MX MXPA04007470A patent/MXPA04007470A/es active IP Right Grant
- 2003-02-14 HR HRP20040707AA patent/HRP20040707B1/hr not_active IP Right Cessation
- 2003-02-14 RS YU74904A patent/RS52392B/sr unknown
- 2003-02-14 EA EA200400953A patent/EA008008B1/ru not_active IP Right Cessation
- 2003-02-14 BR BR0307631-8A patent/BR0307631A/pt not_active IP Right Cessation
- 2003-02-14 CN CNB038080427A patent/CN100486576C/zh not_active Expired - Fee Related
- 2003-02-14 OA OA1200400210A patent/OA12771A/en unknown
- 2003-02-14 DE DE60330126T patent/DE60330126D1/de not_active Expired - Lifetime
- 2003-02-14 CA CA2476012A patent/CA2476012C/en not_active Expired - Fee Related
- 2003-02-14 ES ES03713478T patent/ES2334990T3/es not_active Expired - Lifetime
- 2003-02-14 EP EP03713478A patent/EP1490064B1/en not_active Expired - Lifetime
- 2003-02-14 WO PCT/US2003/004634 patent/WO2003068230A1/en not_active Ceased
- 2003-02-14 AP APAP/P/2004/003105A patent/AP1822A/en active
- 2003-02-14 KR KR1020047012622A patent/KR100705519B1/ko not_active Expired - Fee Related
- 2003-02-14 US US10/367,987 patent/US7067540B2/en not_active Expired - Lifetime
- 2003-02-14 GE GEAP8358A patent/GEP20063937B/en unknown
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2004
- 2004-07-22 IL IL163162A patent/IL163162A/en not_active IP Right Cessation
- 2004-07-26 IS IS7374A patent/IS2735B/is unknown
- 2004-08-05 ZA ZA2004/06275A patent/ZA200406275B/en unknown
- 2004-08-06 CO CO04076760A patent/CO5640132A2/es active IP Right Grant
- 2004-08-09 MA MA27818A patent/MA27268A1/fr unknown
- 2004-08-12 EC EC2004005229A patent/ECSP045229A/es unknown
- 2004-08-12 TN TNP2004000156A patent/TNSN04156A1/fr unknown
- 2004-09-13 NO NO20043820A patent/NO327984B1/no not_active IP Right Cessation
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2005
- 2005-09-14 US US11/226,556 patent/US7629363B2/en not_active Expired - Fee Related
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2006
- 2006-09-13 US US11/531,492 patent/US20070088033A1/en not_active Abandoned
- 2006-09-28 JP JP2006263778A patent/JP5325380B2/ja not_active Expired - Fee Related
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