HRP20010363A2 - SUBSTITUTED PYRAZOLES AS p38 KINASE INHIBITORS - Google Patents
SUBSTITUTED PYRAZOLES AS p38 KINASE INHIBITORS Download PDFInfo
- Publication number
- HRP20010363A2 HRP20010363A2 HR20010363A HRP20010363A HRP20010363A2 HR P20010363 A2 HRP20010363 A2 HR P20010363A2 HR 20010363 A HR20010363 A HR 20010363A HR P20010363 A HRP20010363 A HR P20010363A HR P20010363 A2 HRP20010363 A2 HR P20010363A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- aryl
- heterocyclyl
- hydroxy
- amino
- Prior art date
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- 150000003217 pyrazoles Chemical class 0.000 title description 14
- 229940043355 kinase inhibitor Drugs 0.000 title description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
- -1 hydrido, hydroxy Chemical group 0.000 claims description 1296
- 125000000217 alkyl group Chemical group 0.000 claims description 358
- 125000003118 aryl group Chemical group 0.000 claims description 248
- 150000001875 compounds Chemical class 0.000 claims description 243
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 226
- 125000000623 heterocyclic group Chemical group 0.000 claims description 214
- 150000003254 radicals Chemical group 0.000 claims description 211
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 169
- 125000001188 haloalkyl group Chemical group 0.000 claims description 163
- 125000003545 alkoxy group Chemical group 0.000 claims description 159
- 125000001145 hydrido group Chemical group *[H] 0.000 claims description 146
- 125000000304 alkynyl group Chemical group 0.000 claims description 120
- 125000005843 halogen group Chemical group 0.000 claims description 119
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 113
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 101
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 101
- 125000003342 alkenyl group Chemical group 0.000 claims description 99
- 229910052739 hydrogen Inorganic materials 0.000 claims description 99
- 239000001257 hydrogen Substances 0.000 claims description 99
- 125000003282 alkyl amino group Chemical group 0.000 claims description 96
- 125000001153 fluoro group Chemical group F* 0.000 claims description 93
- 150000003839 salts Chemical class 0.000 claims description 90
- 125000004414 alkyl thio group Chemical group 0.000 claims description 89
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 89
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 88
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 80
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 73
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 73
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 70
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 68
- 125000004104 aryloxy group Chemical group 0.000 claims description 65
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 62
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 62
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 60
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 57
- 125000004076 pyridyl group Chemical group 0.000 claims description 57
- 125000001424 substituent group Chemical group 0.000 claims description 55
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 53
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 53
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 51
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 45
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 45
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 44
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 43
- 125000001769 aryl amino group Chemical group 0.000 claims description 41
- 125000005110 aryl thio group Chemical group 0.000 claims description 41
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 40
- 235000010290 biphenyl Nutrition 0.000 claims description 37
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 37
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 36
- 239000004305 biphenyl Chemical group 0.000 claims description 36
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 36
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- 125000003386 piperidinyl group Chemical group 0.000 claims description 34
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 33
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 32
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 32
- 125000004193 piperazinyl group Chemical group 0.000 claims description 32
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 31
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 31
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 31
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 30
- 150000001721 carbon Chemical group 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 29
- 125000001246 bromo group Chemical group Br* 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 125000001624 naphthyl group Chemical group 0.000 claims description 28
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 125000000335 thiazolyl group Chemical group 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 26
- 229930194542 Keto Natural products 0.000 claims description 25
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 25
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 25
- 125000000468 ketone group Chemical group 0.000 claims description 25
- 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 24
- 208000035475 disorder Diseases 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 125000005494 pyridonyl group Chemical group 0.000 claims description 24
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 23
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 22
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 22
- 102100040247 Tumor necrosis factor Human genes 0.000 claims description 21
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 21
- 125000005182 hydroxyalkylcarbonyl group Chemical group 0.000 claims description 21
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims description 21
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims description 21
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 20
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims description 20
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000005122 aminoalkylamino group Chemical group 0.000 claims description 19
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 19
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 19
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 18
- 125000005128 aryl amino alkyl group Chemical group 0.000 claims description 18
- JSBBMMHTNIUVTC-UHFFFAOYSA-N 2-hydroxyethanone Chemical group OC[C]=O JSBBMMHTNIUVTC-UHFFFAOYSA-N 0.000 claims description 17
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 17
- 125000005016 hydroxyalkynyl group Chemical group 0.000 claims description 17
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 16
- 101000611183 Homo sapiens Tumor necrosis factor Proteins 0.000 claims description 15
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 15
- 125000006310 cycloalkyl amino 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 14
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 14
- 230000001404 mediated effect Effects 0.000 claims description 14
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims description 13
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 13
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 13
- 125000002252 acyl group Chemical group 0.000 claims description 12
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 12
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 12
- 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
- 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 11
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 11
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 11
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 11
- 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 10
- 125000005134 alkynylsulfinyl group Chemical group 0.000 claims description 10
- 125000005139 alkynylsulfonyl group Chemical group 0.000 claims description 10
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 10
- 125000006637 cyclobutyl carbonyl group Chemical group 0.000 claims description 10
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims description 10
- 125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims description 10
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 10
- 125000006332 fluoro benzoyl group Chemical group 0.000 claims description 10
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims description 10
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 10
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 9
- 125000006326 aryl hydrazinyl group Chemical group 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 125000005136 alkenylsulfinyl group Chemical group 0.000 claims description 8
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 8
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 7
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 7
- 230000004054 inflammatory process Effects 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 6
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 6
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 6
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 6
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 6
- 125000005352 carboxycycloalkyl group Chemical group 0.000 claims description 6
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 6
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000005001 aminoaryl group Chemical group 0.000 claims description 5
- 125000001091 aminosulfinyl group Chemical group [H]N([H])S(*)=O 0.000 claims description 5
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 5
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 5
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
- UNLBRWACURAHRZ-UHFFFAOYSA-N oxo-[[1-[[5-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methyl]thiophen-2-yl]methyl]pyridin-4-ylidene]methyl]azanium;diperchlorate Chemical compound [O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O.C1=CC(=C[NH+]=O)C=CN1CC(S1)=CC=C1CN1C=CC(=C[NH+]=O)C=C1 UNLBRWACURAHRZ-UHFFFAOYSA-N 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 206010063837 Reperfusion injury Diseases 0.000 claims description 4
- 125000005108 alkenylthio group Chemical group 0.000 claims description 4
- 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000005109 alkynylthio group Chemical group 0.000 claims description 4
- 206010003246 arthritis Diseases 0.000 claims description 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 4
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 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 description 3
- 206010006895 Cachexia Diseases 0.000 claims description 3
- 201000005569 Gout Diseases 0.000 claims description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
- 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 description 3
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 3
- 125000004468 heterocyclylthio group Chemical group 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical group CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 claims description 3
- UVIDMSMLNGZCSV-UHFFFAOYSA-N 2-ethenylguanidine Chemical group NC(=N)NC=C UVIDMSMLNGZCSV-UHFFFAOYSA-N 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 208000006386 Bone Resorption Diseases 0.000 claims description 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 2
- 208000011231 Crohn disease Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 208000007536 Thrombosis Diseases 0.000 claims description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 2
- 230000024279 bone resorption Effects 0.000 claims description 2
- 230000000747 cardiac effect Effects 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 2
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 claims description 2
- 208000024908 graft versus host disease Diseases 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000006626 methoxycarbonylamino group Chemical group 0.000 claims description 2
- 230000002685 pulmonary effect Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 52
- 125000002947 alkylene group Chemical group 0.000 claims 32
- 125000002346 iodo group Chemical group I* 0.000 claims 26
- 125000004450 alkenylene group Chemical group 0.000 claims 24
- 125000004419 alkynylene group Chemical group 0.000 claims 14
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 14
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 8
- 125000004171 alkoxy aryl group Chemical group 0.000 claims 7
- 238000006467 substitution reaction Methods 0.000 claims 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims 4
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 claims 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 4
- 230000002378 acidificating effect Effects 0.000 claims 3
- 125000003418 alkyl amino alkoxy group Chemical group 0.000 claims 3
- 125000002431 aminoalkoxy group Chemical group 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- 125000004659 aryl alkyl thio 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
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000006550 alkoxycarbonyl aryl group Chemical group 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 208000035474 group of disease Diseases 0.000 claims 1
- 150000002576 ketones Chemical class 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
- 125000003431 oxalo group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229920001281 polyalkylene Polymers 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 21
- 238000011282 treatment Methods 0.000 description 20
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 15
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 13
- 125000002883 imidazolyl group Chemical group 0.000 description 12
- 201000010099 disease Diseases 0.000 description 11
- 102000000589 Interleukin-1 Human genes 0.000 description 10
- 108010002352 Interleukin-1 Proteins 0.000 description 10
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 102000004127 Cytokines Human genes 0.000 description 9
- 108090000695 Cytokines Proteins 0.000 description 9
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 9
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 8
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 8
- 125000002541 furyl group Chemical group 0.000 description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 125000005493 quinolyl group Chemical group 0.000 description 8
- 125000001544 thienyl group Chemical group 0.000 description 8
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 7
- 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 7
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 7
- 206010028980 Neoplasm Diseases 0.000 description 6
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 6
- 125000004673 propylcarbonyl group Chemical group 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 5
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 5
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 4
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/196,623 US6514977B1 (en) | 1997-05-22 | 1998-11-20 | Substituted pyrazoles as p38 kinase inhibitors |
PCT/US1999/026007 WO2000031063A1 (en) | 1998-11-20 | 1999-11-17 | SUBSTITUTED PYRAZOLES AS p38 KINASE INHIBITORS |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20010363A2 true HRP20010363A2 (en) | 2005-02-28 |
Family
ID=22726159
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20010363A HRP20010363A2 (en) | 1998-11-20 | 2001-05-17 | SUBSTITUTED PYRAZOLES AS p38 KINASE INHIBITORS |
Country Status (35)
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US (5) | US6514977B1 (da) |
EP (2) | EP1500657B1 (da) |
JP (1) | JP2002530397A (da) |
KR (1) | KR20030002291A (da) |
CN (1) | CN1342157A (da) |
AP (1) | AP2001002172A0 (da) |
AR (1) | AR035836A1 (da) |
AT (2) | ATE373649T1 (da) |
AU (1) | AU774262B2 (da) |
BG (1) | BG105620A (da) |
BR (1) | BR9915420A (da) |
CA (1) | CA2351725A1 (da) |
CZ (1) | CZ20011714A3 (da) |
DE (2) | DE69937163T2 (da) |
DK (2) | DK1500657T3 (da) |
EA (1) | EA005205B1 (da) |
EE (1) | EE200100268A (da) |
ES (2) | ES2229809T3 (da) |
GE (1) | GEP20053421B (da) |
HK (1) | HK1040705B (da) |
HR (1) | HRP20010363A2 (da) |
HU (1) | HUP0200130A2 (da) |
ID (1) | ID29993A (da) |
IL (1) | IL143120A0 (da) |
IS (1) | IS5938A (da) |
NO (1) | NO20012456L (da) |
NZ (1) | NZ512344A (da) |
OA (1) | OA11914A (da) |
PL (1) | PL353853A1 (da) |
PT (2) | PT1500657E (da) |
SK (1) | SK6862001A3 (da) |
TR (1) | TR200102001T2 (da) |
WO (1) | WO2000031063A1 (da) |
YU (1) | YU35601A (da) |
ZA (1) | ZA200103882B (da) |
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