JP2006519846A5 - - Google Patents
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- JP2006519846A5 JP2006519846A5 JP2006507031A JP2006507031A JP2006519846A5 JP 2006519846 A5 JP2006519846 A5 JP 2006519846A5 JP 2006507031 A JP2006507031 A JP 2006507031A JP 2006507031 A JP2006507031 A JP 2006507031A JP 2006519846 A5 JP2006519846 A5 JP 2006519846A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- independently
- heterocyclyl
- heteroaryl
- halo
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims description 248
- 125000000623 heterocyclic group Chemical group 0.000 claims description 192
- 150000001875 compounds Chemical class 0.000 claims description 173
- 125000001072 heteroaryl group Chemical group 0.000 claims description 134
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 103
- 125000003118 aryl group Chemical group 0.000 claims description 102
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 101
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 82
- 239000000203 mixture Substances 0.000 claims description 74
- -1 R 5 O-alkyl Chemical group 0.000 claims description 65
- 125000003545 alkoxy group Chemical group 0.000 claims description 60
- 125000000304 alkynyl group Chemical group 0.000 claims description 49
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 45
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 41
- 125000004104 aryloxy group Chemical group 0.000 claims description 41
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 41
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims description 41
- 229920000728 polyester Polymers 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 22
- 102000007624 ZAP-70 Protein-Tyrosine Kinase Human genes 0.000 claims description 20
- 108010046882 ZAP-70 Protein-Tyrosine Kinase Proteins 0.000 claims description 20
- 125000004414 alkyl thio group Chemical group 0.000 claims description 20
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 20
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 16
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 239000007822 coupling agent Substances 0.000 claims description 13
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 11
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- OFOBLEOULBTSOW-UHFFFAOYSA-N malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- 125000001041 indolyl group Chemical group 0.000 claims description 7
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 7
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 206010052779 Transplant rejections Diseases 0.000 claims description 5
- 125000005418 aryl aryl group Chemical group 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
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- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
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- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
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- 150000003431 steroids Chemical class 0.000 claims description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 150000002475 indoles Chemical group 0.000 claims description 3
- 230000004073 interleukin-2 production Effects 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims 72
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 12
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- 125000005843 halogen group Chemical group 0.000 description 71
- 201000010099 disease Diseases 0.000 description 23
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- 0 CN1C(*)CCC1 Chemical compound CN1C(*)CCC1 0.000 description 15
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
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- 230000001404 mediated Effects 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
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- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-Bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 5
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- OFUFXTHGZWIDDB-UHFFFAOYSA-N 2-chloroquinoline Chemical compound C1=CC=CC2=NC(Cl)=CC=C21 OFUFXTHGZWIDDB-UHFFFAOYSA-N 0.000 description 3
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- DCWXELXMIBXGTH-UHFFFAOYSA-N O(4)-phosphotyrosine Chemical compound OC(=O)C(N)CC1=CC=C(OP(O)(O)=O)C=C1 DCWXELXMIBXGTH-UHFFFAOYSA-N 0.000 description 3
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| US2472066A (en) * | 1949-06-07 | Z-arylamino-x-halogenoqtjinolines | ||
| DE537104C (de) * | 1926-05-04 | 1933-03-17 | Chem Ind Basel | Verfahren zur Darstellung von substituierten Chinolincarbonsaeureamiden |
| DE858698C (de) * | 1951-02-09 | 1952-12-08 | Basf Ag | Verfahren zur Herstellung von Pyridin- und Chinolinderivaten |
| GB811957A (en) * | 1956-03-01 | 1959-04-15 | Geigy Ag J R | Improvements relating to 2-hydroxy-4-arylamino-quinolines |
| FR6103M (es) * | 1967-02-22 | 1968-06-10 | ||
| US3755332A (en) * | 1971-07-01 | 1973-08-28 | Ciba Geigy Corp | Substituted 4 indazolaminoquinolines |
| FR2538388B1 (fr) * | 1982-12-24 | 1985-06-21 | Pharmuka Lab | Nouveaux derives de naphtalene- ou azanaphtalenecarboxamide, leurs procedes de preparation et leur utilisation comme medicaments |
| JPH05310702A (ja) * | 1992-05-06 | 1993-11-22 | Kyowa Hakko Kogyo Co Ltd | 抗炎症剤、免疫調整剤およびキノリン−２，４−ジカルボン酸ジアミド誘導体 |
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2004
- 2004-03-10 MX MXPA05009722A patent/MXPA05009722A/es not_active Application Discontinuation
- 2004-03-10 EP EP04719237A patent/EP1601357A4/en not_active Withdrawn
- 2004-03-10 CA CA002518398A patent/CA2518398A1/en not_active Abandoned
- 2004-03-10 WO PCT/US2004/007286 patent/WO2004080463A1/en active Application Filing
- 2004-03-10 JP JP2006507031A patent/JP2006519846A/ja active Pending
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