CN1264377A - 用作p38激酶抑制剂的取代的吡唑化合物 - Google Patents

Info

Publication number

CN1264377A

CN1264377A CN98807369A CN98807369A CN1264377A CN 1264377 A CN1264377 A CN 1264377A CN 98807369 A CN98807369 A CN 98807369A CN 98807369 A CN98807369 A CN 98807369A CN 1264377 A CN1264377 A CN 1264377A

Authority

CN

China

Prior art keywords

alkyl

group

amino

heterocyclic radical

carbonyl

Prior art date

1997-05-22

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.)

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• 150000003217 pyrazoles Chemical class 0.000 title claims abstract description 10
• 108091000080 Phosphotransferase Proteins 0.000 title claims description 20
• 102000020233 phosphotransferase Human genes 0.000 title claims description 20
• 150000001875 compounds Chemical class 0.000 claims abstract description 170
• 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims abstract description 39
• 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims abstract description 39
• 230000001404 mediated effect Effects 0.000 claims abstract description 21
• -1 heterocyclic radical Chemical class 0.000 claims description 977
• 125000001118 alkylidene group Chemical group 0.000 claims description 505
• 125000000217 alkyl group Chemical group 0.000 claims description 414
• 125000003118 aryl group Chemical group 0.000 claims description 251
• 239000001257 hydrogen Substances 0.000 claims description 239
• 229910052739 hydrogen Inorganic materials 0.000 claims description 239
• 125000003545 alkoxy group Chemical group 0.000 claims description 204
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 186
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 163
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 153
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 139
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 136
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 136
• 125000003282 alkyl amino group Chemical group 0.000 claims description 126
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 122
• 229910052736 halogen Inorganic materials 0.000 claims description 105
• 150000002367 halogens Chemical class 0.000 claims description 105
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 102
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 94
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 93
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 92
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 88
• 125000003342 alkenyl group Chemical group 0.000 claims description 87
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 82
• 125000004414 alkyl thio group Chemical group 0.000 claims description 80
• 125000004104 aryloxy group Chemical group 0.000 claims description 80
• 125000000304 alkynyl group Chemical group 0.000 claims description 76
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 76
• 150000003839 salts Chemical class 0.000 claims description 75
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 74
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 72
• 125000001188 haloalkyl group Chemical group 0.000 claims description 66
• QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 66
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 57
• 125000000623 heterocyclic group Chemical group 0.000 claims description 53
• 125000000468 ketone group Chemical group 0.000 claims description 53
• 125000001769 aryl amino group Chemical group 0.000 claims description 52
• 125000004076 pyridyl group Chemical group 0.000 claims description 52
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 50
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 50
• 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims description 48
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 48
• 239000011737 fluorine Substances 0.000 claims description 47
• 229910052731 fluorine Inorganic materials 0.000 claims description 47
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 46
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 45
• 201000010099 disease Diseases 0.000 claims description 45
• 125000001624 naphthyl group Chemical group 0.000 claims description 45
• 238000000034 method Methods 0.000 claims description 44
• 125000006319 alkynyl amino group Chemical group 0.000 claims description 43
• 229910052760 oxygen Inorganic materials 0.000 claims description 41
• 239000001301 oxygen Substances 0.000 claims description 41
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 41
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 40
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 39
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 37
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 35
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 34
• 125000005493 quinolyl group Chemical group 0.000 claims description 33
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 32
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 32
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 31
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 30
• 239000004215 Carbon black (E152) Substances 0.000 claims description 28
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 28
• 229930195733 hydrocarbon Natural products 0.000 claims description 28
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 28
• 125000006323 alkenyl amino group Chemical group 0.000 claims description 26
• 125000005110 aryl thio group Chemical group 0.000 claims description 25
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
• KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 24
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 24
• 125000004193 piperazinyl group Chemical group 0.000 claims description 24
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 23
• 125000005248 alkyl aryloxy group Chemical group 0.000 claims description 23
• 125000002757 morpholinyl group Chemical group 0.000 claims description 22
• 238000011282 treatment Methods 0.000 claims description 22
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 20
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 20
• 125000005936 piperidyl group Chemical group 0.000 claims description 19
• 125000005452 alkenyloxyalkyl group Chemical group 0.000 claims description 18
• 125000005128 aryl amino alkyl group Chemical group 0.000 claims description 18
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 18
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 18
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 18
• 125000002883 imidazolyl group Chemical group 0.000 claims description 18
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 17
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 17
• 239000000203 mixture Substances 0.000 claims description 17
• ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical group CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 claims description 16
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 16
• 150000002430 hydrocarbons Chemical class 0.000 claims description 16
• NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 16
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 15
• 125000002541 furyl group Chemical group 0.000 claims description 15
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 14
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 14
• 206010061218 Inflammation Diseases 0.000 claims description 13
• 125000002252 acyl group Chemical group 0.000 claims description 13
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 230000004054 inflammatory process Effects 0.000 claims description 13
• 125000001544 thienyl group Chemical group 0.000 claims description 13
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 12
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 12
• 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 claims description 12
• 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
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 10
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 10
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 10
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 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
• 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 10
• 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 10
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 10
• 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 10
• 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 10
• 206010063837 Reperfusion injury Diseases 0.000 claims description 9
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
• 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 9
• 229920002554 vinyl polymer Polymers 0.000 claims description 9
• 125000004896 2-methylbutylamino group Chemical group CC(CN*)CC 0.000 claims description 8
• 125000005136 alkenylsulfinyl group Chemical group 0.000 claims description 8
• 125000005001 aminoaryl group Chemical group 0.000 claims description 8
• 125000001091 aminosulfinyl group Chemical group [H]N([H])S(*)=O 0.000 claims description 8
• 208000006673 asthma Diseases 0.000 claims description 8
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
• 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
• 125000006627 ethoxycarbonylamino group Chemical group 0.000 claims description 8
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 8
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 8
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 8
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
• 206010039361 Sacroiliitis Diseases 0.000 claims description 7
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 7
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
• 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 7
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 7
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 7
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 7
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 7
• 206010035664 Pneumonia Diseases 0.000 claims description 6
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
• CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 claims description 6
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 6
• UKPXULFIISGBHG-UHFFFAOYSA-N cyclopropene Chemical compound [CH]1C=C1 UKPXULFIISGBHG-UHFFFAOYSA-N 0.000 claims description 6
• 125000006003 dichloroethyl group Chemical group 0.000 claims description 6
• 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims description 6
• 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 6
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 6
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 6
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• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 5
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• 229910052757 nitrogen Inorganic materials 0.000 claims description 5
• WIHIUTUAHOZVLE-UHFFFAOYSA-N 1,3-diethoxypropan-2-ol Chemical compound CCOCC(O)COCC WIHIUTUAHOZVLE-UHFFFAOYSA-N 0.000 claims description 4
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• MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 4
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• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
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• 125000004367 cycloalkylaryl group Chemical group 0.000 claims description 4
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 4
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• YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 3
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• KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical class OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 claims description 2
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