OA11914A - Substitutez pyrazoles as p38 kinase inhibitors. - Google Patents

Info

Publication number

OA11914A

OA11914A OA00100123A OA00100123A OA11914A OA 11914 A OA11914 A OA 11914A OA 00100123 A OA00100123 A OA 00100123A OA 00100123 A OA00100123 A OA 00100123A OA 11914 A OA11914 A OA 11914A

Authority

OA

OAPI

Prior art keywords

alkyl

aryl

amino

hydroxy

heterocyclyl

Prior art date

1998-11-20

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• 150000003217 pyrazoles Chemical class 0.000 title claims abstract description 12
• 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 title abstract description 14
• 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 title abstract description 14
• 229940043355 kinase inhibitor Drugs 0.000 title description 2
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 216
• -1 hydrido, hydroxy Chemical group 0.000 claims description 1522
• 125000000217 alkyl group Chemical group 0.000 claims description 362
• 125000003118 aryl group Chemical group 0.000 claims description 259
• 125000000623 heterocyclic group Chemical group 0.000 claims description 210
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 207
• 125000003545 alkoxy group Chemical group 0.000 claims description 173
• 125000001188 haloalkyl group Chemical group 0.000 claims description 163
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 161
• 125000001145 hydrido group Chemical group *[H] 0.000 claims description 142
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 142
• 125000005843 halogen group Chemical group 0.000 claims description 125
• 125000003282 alkyl amino group Chemical group 0.000 claims description 119
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 118
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 115
• 125000000304 alkynyl group Chemical group 0.000 claims description 114
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 112
• 125000003342 alkenyl group Chemical group 0.000 claims description 101
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 101
• 125000001153 fluoro group Chemical group F* 0.000 claims description 99
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 95
• 125000004414 alkyl thio group Chemical group 0.000 claims description 90
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 90
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 89
• 229910052739 hydrogen Inorganic materials 0.000 claims description 88
• 239000001257 hydrogen Substances 0.000 claims description 88
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 84
• 125000004104 aryloxy group Chemical group 0.000 claims description 83
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 83
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 76
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 67
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 65
• 125000001769 aryl amino group Chemical group 0.000 claims description 59
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 53
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 52
• 150000003254 radicals Chemical class 0.000 claims description 52
• 125000004076 pyridyl group Chemical group 0.000 claims description 51
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 48
• 125000006319 alkynyl amino group Chemical group 0.000 claims description 47
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 46
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 46
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 45
• 125000005110 aryl thio group Chemical group 0.000 claims description 44
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 42
• 229930194542 Keto Chemical group 0.000 claims description 41
• 125000000468 ketone group Chemical group 0.000 claims description 41
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 37
• 125000001246 bromo group Chemical group Br* 0.000 claims description 35
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 34
• 229910052757 nitrogen Inorganic materials 0.000 claims description 34
• 125000001424 substituent group Chemical group 0.000 claims description 34
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 32
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 32
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 32
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 31
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 31
• 125000006323 alkenyl amino group Chemical group 0.000 claims description 30
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 30
• 229910052736 halogen Inorganic materials 0.000 claims description 29
• 150000002367 halogens Chemical class 0.000 claims description 29
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 29
• 125000000335 thiazolyl group Chemical group 0.000 claims description 29
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 27
• 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 27
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 27
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 26
• 125000003386 piperidinyl group Chemical group 0.000 claims description 26
• 125000005494 pyridonyl group Chemical group 0.000 claims description 26
• 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 25
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 24
• 125000005182 hydroxyalkylcarbonyl group Chemical group 0.000 claims description 23
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 22
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 22
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 22
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 21
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 21
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 21
• 125000001624 naphthyl group Chemical group 0.000 claims description 21
• 125000005122 aminoalkylamino group Chemical group 0.000 claims description 20
• 125000005020 hydroxyalkenyl group Chemical group 0.000 claims description 20
• 125000005128 aryl amino alkyl group Chemical group 0.000 claims description 19
• 150000001721 carbon Chemical group 0.000 claims description 19
• 229910052799 carbon Inorganic materials 0.000 claims description 19
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 18
• 125000005016 hydroxyalkynyl group Chemical group 0.000 claims description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 17
• 125000004193 piperazinyl group Chemical group 0.000 claims description 17
• 125000002252 acyl group Chemical group 0.000 claims description 16
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 16
• 125000004429 atom Chemical group 0.000 claims description 16
• 125000005136 alkenylsulfinyl group Chemical group 0.000 claims description 15
• 125000005139 alkynylsulfonyl group Chemical group 0.000 claims description 15
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 15
• 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 15
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 14
• 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims description 14
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 14
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 14
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 14
• 125000004171 alkoxy aryl group Chemical group 0.000 claims description 13
• 125000005134 alkynylsulfinyl group Chemical group 0.000 claims description 13
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 13
• 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 13
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 13
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 12
• 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 12
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 12
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 12
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 12
• JSBBMMHTNIUVTC-UHFFFAOYSA-N 2-hydroxyethanone Chemical group OC[C]=O JSBBMMHTNIUVTC-UHFFFAOYSA-N 0.000 claims description 11
• 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 claims description 11
• 125000003418 alkyl amino alkoxy group Chemical group 0.000 claims description 11
• 125000006326 aryl hydrazinyl group Chemical group 0.000 claims description 11
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 11
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 11
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 10
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
• RXBMEHOLQJITJI-LEOXJPRUSA-N (4s)-5-amino-4-[[(2s)-2-[[(2s)-2-[[(4-bromophenyl)-hydroxyphosphoryl]methyl]-3-(3-phenyl-1,2-oxazol-5-yl)propanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoic acid Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N)CP(O)(=O)C=1C=CC(Br)=CC=1)C(ON=1)=CC=1C1=CC=CC=C1 RXBMEHOLQJITJI-LEOXJPRUSA-N 0.000 claims description 9
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 9
• 125000001091 aminosulfinyl group Chemical group [H]N([H])S(*)=O 0.000 claims description 9
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 9
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 9
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 9
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 8
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 8
• 238000000034 method Methods 0.000 claims description 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
• 125000005108 alkenylthio group Chemical group 0.000 claims description 7
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 7
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 7
• 125000005109 alkynylthio group Chemical group 0.000 claims description 7
• 125000002431 aminoalkoxy group Chemical group 0.000 claims description 7
• 125000005111 carboxyalkoxy group Chemical group 0.000 claims description 7
• 125000005159 cyanoalkoxy group Chemical group 0.000 claims description 7
• 125000006627 ethoxycarbonylamino group Chemical group 0.000 claims description 7
• 125000006332 fluoro benzoyl group Chemical group 0.000 claims description 7
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
• 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 6
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 6
• 125000005352 carboxycycloalkyl group Chemical group 0.000 claims description 6
• 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims description 6
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 6
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 6
• 125000004468 heterocyclylthio group Chemical group 0.000 claims description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 5
• DBGOOVYOTHGFFZ-UHFFFAOYSA-N C(N)(=N)N(C(N(C(=C=CNC(=N)N)NC(=N)N)C(NCC1=CC=CC=C1)=N)=NC(NC)=N)C(NC)=N Chemical group C(N)(=N)N(C(N(C(=C=CNC(=N)N)NC(=N)N)C(NCC1=CC=CC=C1)=N)=NC(NC)=N)C(NC)=N DBGOOVYOTHGFFZ-UHFFFAOYSA-N 0.000 claims description 5
• 239000004215 Carbon black (E152) Substances 0.000 claims description 5
• 125000005001 aminoaryl group Chemical group 0.000 claims description 5
• 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 5
• 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 5
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
• 229930195733 hydrocarbon Natural products 0.000 claims description 5
• 150000002430 hydrocarbons Chemical class 0.000 claims description 5
• 125000006626 methoxycarbonylamino group Chemical group 0.000 claims description 5
• OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 claims description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
• 239000002253 acid Substances 0.000 claims description 2
• 125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 43
• 125000002947 alkylene group Chemical group 0.000 claims 29
• 125000002346 iodo group Chemical group I* 0.000 claims 25
• 125000004450 alkenylene group Chemical group 0.000 claims 24
• 125000004419 alkynylene group Chemical group 0.000 claims 22
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims 11
• 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 5
• 125000005350 hydroxycycloalkyl group Chemical group 0.000 claims 5
• 125000002071 phenylalkoxy group Chemical group 0.000 claims 5
• 102220498322 HLA class II histocompatibility antigen, DR beta 3 chain_R40S_mutation Human genes 0.000 claims 4
• 101150052863 THY1 gene Proteins 0.000 claims 4
• WVXDALCQQYPHCG-UHFFFAOYSA-N CNC=CNC=C=CNCC Chemical group CNC=CNC=C=CNCC WVXDALCQQYPHCG-UHFFFAOYSA-N 0.000 claims 2
• GYRPAYDYHMZXQT-KZULUSFZSA-N N-[(1S,5R)-3-[5-fluoro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]-3-azabicyclo[3.1.0]hexan-1-yl]cyclopropanecarboxamide Chemical compound C1CC1C(=O)N[C@@]23C[C@@H]2CN(C3)C4=NC(=NC=C4F)NC5=CN(N=C5)CCO GYRPAYDYHMZXQT-KZULUSFZSA-N 0.000 claims 2
• 125000005325 aryloxy aryl group Chemical group 0.000 claims 2
• ZUCWUADHUDQXHX-UHFFFAOYSA-N but-1-en-2-amine Chemical group CCC(N)=C ZUCWUADHUDQXHX-UHFFFAOYSA-N 0.000 claims 2
• 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
• 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
• 229910052760 oxygen Inorganic materials 0.000 claims 2
• LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims 1
• XDHOEHJVXXTEDV-UHFFFAOYSA-N 1-ethoxyprop-1-ene Chemical group CCOC=CC XDHOEHJVXXTEDV-UHFFFAOYSA-N 0.000 claims 1
• YBVDBOSCTLHEBH-UHFFFAOYSA-N C(C)OC=C=COCC Chemical group C(C)OC=C=COCC YBVDBOSCTLHEBH-UHFFFAOYSA-N 0.000 claims 1
• HSPRAJKYYHMMLK-UHFFFAOYSA-N C(C1=CC=CC=C1)NC(=N)N(C(=N)N)C(=C=CNC(=N)N)NC(=N)N Chemical group C(C1=CC=CC=C1)NC(=N)N(C(=N)N)C(=C=CNC(=N)N)NC(=N)N HSPRAJKYYHMMLK-UHFFFAOYSA-N 0.000 claims 1
• HWBVBFFFIWILID-UHFFFAOYSA-N CNC(=N)N=C(N(C(=C=CNC(=N)N)NC(=N)N)C(NCC1=CC=CC=C1)=N)N Chemical group CNC(=N)N=C(N(C(=C=CNC(=N)N)NC(=N)N)C(NCC1=CC=CC=C1)=N)N HWBVBFFFIWILID-UHFFFAOYSA-N 0.000 claims 1
• 101100062121 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cyc-1 gene Proteins 0.000 claims 1
• 230000002378 acidificating effect Effects 0.000 claims 1
• 125000002877 alkyl aryl group Chemical group 0.000 claims 1
• 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 claims 1
• 125000000732 arylene group Chemical group 0.000 claims 1
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims 1
• 125000006317 cyclopropyl amino group Chemical group 0.000 claims 1
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
• 150000002576 ketones Chemical class 0.000 claims 1
• XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical group COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 claims 1
• NEYAGKMQJMQQLW-UHFFFAOYSA-N n-prop-1-enyl-n-propylpropan-1-amine Chemical group CCCN(CCC)C=CC NEYAGKMQJMQQLW-UHFFFAOYSA-N 0.000 claims 1
• 239000003960 organic solvent Substances 0.000 claims 1
• 239000008194 pharmaceutical composition Substances 0.000 claims 1
• 125000006513 pyridinyl methyl group Chemical group 0.000 claims 1
• 150000003839 salts Chemical class 0.000 claims 1
• 239000002904 solvent Substances 0.000 claims 1
• 230000001404 mediated effect Effects 0.000 abstract description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 105
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 64
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• 235000010290 biphenyl Nutrition 0.000 description 32
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• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 29
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• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 13
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• 102000000589 Interleukin-1 Human genes 0.000 description 10
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• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 10
• 125000002883 imidazolyl group Chemical group 0.000 description 10
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• 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 7
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• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 7
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• 125000001544 thienyl group Chemical group 0.000 description 7
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• 125000006125 ethylsulfonyl group Chemical group 0.000 description 6
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• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 5
• 230000003110 anti-inflammatory effect Effects 0.000 description 5
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 5
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• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 5
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• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
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