JP2009519280A - 有機化合物 - Google Patents
有機化合物 Download PDFInfo
- Publication number
- JP2009519280A JP2009519280A JP2008544872A JP2008544872A JP2009519280A JP 2009519280 A JP2009519280 A JP 2009519280A JP 2008544872 A JP2008544872 A JP 2008544872A JP 2008544872 A JP2008544872 A JP 2008544872A JP 2009519280 A JP2009519280 A JP 2009519280A
- Authority
- JP
- Japan
- Prior art keywords
- methylthiazol
- ethyl
- ureido
- alkyl
- imidazol
- 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
Links
- 150000002894 organic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 150000003839 salts Chemical group 0.000 claims abstract description 24
- 238000011282 treatment Methods 0.000 claims abstract description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- -1 C 1 -C 6 -alkyl Chemical group 0.000 claims description 30
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 230000002757 inflammatory effect Effects 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 230000000414 obstructive effect Effects 0.000 claims description 8
- 208000023504 respiratory system disease Diseases 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 3
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- CWYLZQIDGLGCJD-UHFFFAOYSA-N 1-[2-[1-(2-fluoroethyl)imidazol-4-yl]ethyl]-3-[4-methyl-5-(1-oxo-2,3-dihydroinden-5-yl)-1,3-thiazol-2-yl]urea Chemical compound S1C(C=2C=C3CCC(=O)C3=CC=2)=C(C)N=C1NC(=O)NCCC1=CN(CCF)C=N1 CWYLZQIDGLGCJD-UHFFFAOYSA-N 0.000 claims 1
- ZKRXLRXFCAKXLW-UHFFFAOYSA-N 1-[2-[1-(2-fluoroethyl)imidazol-4-yl]ethyl]-3-[4-methyl-5-(4-propanoylphenyl)-1,3-thiazol-2-yl]urea Chemical compound C1=CC(C(=O)CC)=CC=C1C1=C(C)N=C(NC(=O)NCCC=2N=CN(CCF)C=2)S1 ZKRXLRXFCAKXLW-UHFFFAOYSA-N 0.000 claims 1
- PYVYLRHVTDAIGH-UHFFFAOYSA-N 1-[4-methyl-5-(1-oxo-2,3-dihydroinden-5-yl)-1,3-thiazol-2-yl]-3-[2-(1-propan-2-ylimidazol-4-yl)ethyl]urea Chemical compound CC(C)N1C=NC(CCNC(=O)NC=2SC(=C(C)N=2)C=2C=C3CCC(=O)C3=CC=2)=C1 PYVYLRHVTDAIGH-UHFFFAOYSA-N 0.000 claims 1
- MNKNOCSQSUDKEJ-UHFFFAOYSA-N 1-[5-(4-acetyl-3-fluorophenyl)-4-methyl-1,3-thiazol-2-yl]-3-[2-(1-propan-2-ylimidazol-4-yl)ethyl]urea Chemical compound CC(C)N1C=NC(CCNC(=O)NC=2SC(=C(C)N=2)C=2C=C(F)C(C(C)=O)=CC=2)=C1 MNKNOCSQSUDKEJ-UHFFFAOYSA-N 0.000 claims 1
- RPOXUABUWOJEDY-UHFFFAOYSA-N 1-[5-(4-acetylphenyl)-4-methyl-1,3-thiazol-2-yl]-3-[2-(1-propan-2-ylimidazol-4-yl)ethyl]urea Chemical compound CC(C)N1C=NC(CCNC(=O)NC=2SC(=C(C)N=2)C=2C=CC(=CC=2)C(C)=O)=C1 RPOXUABUWOJEDY-UHFFFAOYSA-N 0.000 claims 1
- CJTKMGNPIIKPFA-UHFFFAOYSA-N 1-[5-(4-acetylphenyl)-4-methyl-1,3-thiazol-2-yl]-3-[2-[1-(2-fluoroethyl)imidazol-4-yl]ethyl]urea Chemical compound C1=CC(C(=O)C)=CC=C1C1=C(C)N=C(NC(=O)NCCC=2N=CN(CCF)C=2)S1 CJTKMGNPIIKPFA-UHFFFAOYSA-N 0.000 claims 1
- NMMZFFWBGGSURC-UHFFFAOYSA-N 1-[5-[4-(cyclopropanecarbonyl)phenyl]-4-methyl-1,3-thiazol-2-yl]-3-[2-(1-ethylimidazol-4-yl)ethyl]urea Chemical compound CCN1C=NC(CCNC(=O)NC=2SC(=C(C)N=2)C=2C=CC(=CC=2)C(=O)C2CC2)=C1 NMMZFFWBGGSURC-UHFFFAOYSA-N 0.000 claims 1
- VKWPXIDILHROAB-UHFFFAOYSA-N 1-[5-[4-(cyclopropanecarbonyl)phenyl]-4-methyl-1,3-thiazol-2-yl]-3-[2-(1-propan-2-ylimidazol-4-yl)ethyl]urea Chemical compound CC(C)N1C=NC(CCNC(=O)NC=2SC(=C(C)N=2)C=2C=CC(=CC=2)C(=O)C2CC2)=C1 VKWPXIDILHROAB-UHFFFAOYSA-N 0.000 claims 1
- VYPSAQSZIROLAK-UHFFFAOYSA-N 1-[5-[4-(cyclopropanecarbonyl)phenyl]-4-methyl-1,3-thiazol-2-yl]-3-[2-(2-ethyltetrazol-5-yl)ethyl]urea Chemical compound CCN1N=NC(CCNC(=O)NC=2SC(=C(C)N=2)C=2C=CC(=CC=2)C(=O)C2CC2)=N1 VYPSAQSZIROLAK-UHFFFAOYSA-N 0.000 claims 1
- VRUVUFCYFJOXRL-UHFFFAOYSA-N 1-[5-[4-(cyclopropanecarbonyl)phenyl]-4-methyl-1,3-thiazol-2-yl]-3-[2-(5-ethyl-1,3-oxazol-2-yl)ethyl]urea Chemical compound O1C(CC)=CN=C1CCNC(=O)NC1=NC(C)=C(C=2C=CC(=CC=2)C(=O)C2CC2)S1 VRUVUFCYFJOXRL-UHFFFAOYSA-N 0.000 claims 1
- NLFCZOFIDQUBGP-UHFFFAOYSA-N 1-[5-[4-(cyclopropanecarbonyl)phenyl]-4-methyl-1,3-thiazol-2-yl]-3-[2-[1-(2-fluoroethyl)imidazol-4-yl]ethyl]urea Chemical compound S1C(C=2C=CC(=CC=2)C(=O)C2CC2)=C(C)N=C1NC(=O)NCCC1=CN(CCF)C=N1 NLFCZOFIDQUBGP-UHFFFAOYSA-N 0.000 claims 1
- NXVAEVHJWOBXKG-UHFFFAOYSA-N 2-methoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1OC NXVAEVHJWOBXKG-UHFFFAOYSA-N 0.000 claims 1
- UTPZCQJADKDEAD-UHFFFAOYSA-N 3-[[5-(4-acetyl-3-fluorophenyl)-4-methyl-1,3-thiazol-2-yl]carbamoylamino]-n-(2,2-difluoroethyl)propanamide Chemical compound C1=C(F)C(C(=O)C)=CC=C1C1=C(C)N=C(NC(=O)NCCC(=O)NCC(F)F)S1 UTPZCQJADKDEAD-UHFFFAOYSA-N 0.000 claims 1
- RSAKNICQGBYLTQ-UHFFFAOYSA-N 3-[[5-(4-acetyl-3-fluorophenyl)-4-methyl-1,3-thiazol-2-yl]carbamoylamino]-n-tert-butylpropanamide Chemical compound C1=C(F)C(C(=O)C)=CC=C1C1=C(C)N=C(NC(=O)NCCC(=O)NC(C)(C)C)S1 RSAKNICQGBYLTQ-UHFFFAOYSA-N 0.000 claims 1
- HORKAZVGIMOKJE-UHFFFAOYSA-N 3-[[5-(4-acetylphenyl)-4-methyl-1,3-thiazol-2-yl]carbamoylamino]-n-(2,2-difluoroethyl)propanamide Chemical compound C1=CC(C(=O)C)=CC=C1C1=C(C)N=C(NC(=O)NCCC(=O)NCC(F)F)S1 HORKAZVGIMOKJE-UHFFFAOYSA-N 0.000 claims 1
- KMDWTTDOKGHNBI-UHFFFAOYSA-N 3-[[5-(4-acetylphenyl)-4-methyl-1,3-thiazol-2-yl]carbamoylamino]-n-(2-fluoroethyl)propanamide Chemical compound C1=CC(C(=O)C)=CC=C1C1=C(C)N=C(NC(=O)NCCC(=O)NCCF)S1 KMDWTTDOKGHNBI-UHFFFAOYSA-N 0.000 claims 1
- IUPXLLWDLOWEBR-UHFFFAOYSA-N 3-[[5-(4-acetylphenyl)-4-methyl-1,3-thiazol-2-yl]carbamoylamino]-n-tert-butylpropanamide Chemical compound C1=CC(C(=O)C)=CC=C1C1=C(C)N=C(NC(=O)NCCC(=O)NC(C)(C)C)S1 IUPXLLWDLOWEBR-UHFFFAOYSA-N 0.000 claims 1
- BBSGKSPDODSHFS-UHFFFAOYSA-N 3-[[5-[4-(cyclopropanecarbonyl)phenyl]-4-methyl-1,3-thiazol-2-yl]carbamoylamino]-n-(2,2-difluoroethyl)propanamide Chemical compound N1=C(NC(=O)NCCC(=O)NCC(F)F)SC(C=2C=CC(=CC=2)C(=O)C2CC2)=C1C BBSGKSPDODSHFS-UHFFFAOYSA-N 0.000 claims 1
- KCNPDWFYWXQCJW-UHFFFAOYSA-N 4-[2-[2-[1-(2-fluoroethyl)imidazol-4-yl]ethylcarbamoylamino]-4-methyl-1,3-thiazol-5-yl]benzoic acid Chemical compound S1C(C=2C=CC(=CC=2)C(O)=O)=C(C)N=C1NC(=O)NCCC1=CN(CCF)C=N1 KCNPDWFYWXQCJW-UHFFFAOYSA-N 0.000 claims 1
- OALZNYWZZBMGQA-UHFFFAOYSA-N 4-[2-[[3-(2,2-difluoroethylamino)-3-oxopropyl]carbamoylamino]-4-methyl-1,3-thiazol-5-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C(C)N=C(NC(=O)NCCC(=O)NCC(F)F)S1 OALZNYWZZBMGQA-UHFFFAOYSA-N 0.000 claims 1
- BSLJRDPOEHSLBF-UHFFFAOYSA-N 4-[2-[[3-(2,2-difluoroethylamino)-3-oxopropyl]carbamoylamino]-4-methyl-1,3-thiazol-5-yl]-n-propan-2-ylbenzamide Chemical compound C1=CC(C(=O)NC(C)C)=CC=C1C1=C(C)N=C(NC(=O)NCCC(=O)NCC(F)F)S1 BSLJRDPOEHSLBF-UHFFFAOYSA-N 0.000 claims 1
- LNWFXNTXTWTRNE-UHFFFAOYSA-N 4-[2-[[3-(2,2-difluoroethylamino)-3-oxopropyl]carbamoylamino]-4-methyl-1,3-thiazol-5-yl]benzoic acid Chemical compound N1=C(NC(=O)NCCC(=O)NCC(F)F)SC(C=2C=CC(=CC=2)C(O)=O)=C1C LNWFXNTXTWTRNE-UHFFFAOYSA-N 0.000 claims 1
- OGBKHHMGFLWINA-UHFFFAOYSA-N 4-[2-[[3-(2-fluoroethylamino)-3-oxopropyl]carbamoylamino]-4-methyl-1,3-thiazol-5-yl]-n-propan-2-ylbenzamide Chemical compound C1=CC(C(=O)NC(C)C)=CC=C1C1=C(C)N=C(NC(=O)NCCC(=O)NCCF)S1 OGBKHHMGFLWINA-UHFFFAOYSA-N 0.000 claims 1
- DPYGNZMGVAZQAV-UHFFFAOYSA-N 4-[2-[[3-(tert-butylamino)-3-oxopropyl]carbamoylamino]-4-methyl-1,3-thiazol-5-yl]-n-cyclopropylbenzamide Chemical compound N1=C(NC(=O)NCCC(=O)NC(C)(C)C)SC(C=2C=CC(=CC=2)C(=O)NC2CC2)=C1C DPYGNZMGVAZQAV-UHFFFAOYSA-N 0.000 claims 1
- TWSZFZSXMHWVBV-UHFFFAOYSA-N 4-[2-[[3-(tert-butylamino)-3-oxopropyl]carbamoylamino]-4-methyl-1,3-thiazol-5-yl]-n-methoxy-n-methylbenzamide Chemical compound C1=CC(C(=O)N(C)OC)=CC=C1C1=C(C)N=C(NC(=O)NCCC(=O)NC(C)(C)C)S1 TWSZFZSXMHWVBV-UHFFFAOYSA-N 0.000 claims 1
- MISXDFDEKUBLSR-UHFFFAOYSA-N 4-[2-[[3-(tert-butylamino)-3-oxopropyl]carbamoylamino]-4-methyl-1,3-thiazol-5-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C(C)N=C(NC(=O)NCCC(=O)NC(C)(C)C)S1 MISXDFDEKUBLSR-UHFFFAOYSA-N 0.000 claims 1
- OZYOQJOFKGBOCY-UHFFFAOYSA-N 4-[2-[[3-(tert-butylamino)-3-oxopropyl]carbamoylamino]-4-methyl-1,3-thiazol-5-yl]-n-propan-2-ylbenzamide Chemical compound C1=CC(C(=O)NC(C)C)=CC=C1C1=C(C)N=C(NC(=O)NCCC(=O)NC(C)(C)C)S1 OZYOQJOFKGBOCY-UHFFFAOYSA-N 0.000 claims 1
- UECFUHQWPPIZCW-UHFFFAOYSA-N 4-[4-methyl-2-[2-(1-propan-2-ylimidazol-4-yl)ethylcarbamoylamino]-1,3-thiazol-5-yl]benzoic acid Chemical compound CC(C)N1C=NC(CCNC(=O)NC=2SC(=C(C)N=2)C=2C=CC(=CC=2)C(O)=O)=C1 UECFUHQWPPIZCW-UHFFFAOYSA-N 0.000 claims 1
- DSGSUZZCLFHSGV-UHFFFAOYSA-N N1=C(NC(=O)NCCC(=O)NCC(F)(F)F)SC(C=2C(=CC=CC=2)C(N)=O)=C1C Chemical compound N1=C(NC(=O)NCCC(=O)NCC(F)(F)F)SC(C=2C(=CC=CC=2)C(N)=O)=C1C DSGSUZZCLFHSGV-UHFFFAOYSA-N 0.000 claims 1
- AALZBACZJIVTBU-UHFFFAOYSA-N ethyl 4-[2-[2-[1-(2-fluoroethyl)imidazol-4-yl]ethylcarbamoylamino]-4-methyl-1,3-thiazol-5-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C1=C(C)N=C(NC(=O)NCCC=2N=CN(CCF)C=2)S1 AALZBACZJIVTBU-UHFFFAOYSA-N 0.000 claims 1
- WSOGLOXRGUXGJK-UHFFFAOYSA-N ethyl 4-[2-[[3-(2,2-difluoroethylamino)-3-oxopropyl]carbamoylamino]-4-methyl-1,3-thiazol-5-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C1=C(C)N=C(NC(=O)NCCC(=O)NCC(F)F)S1 WSOGLOXRGUXGJK-UHFFFAOYSA-N 0.000 claims 1
- QXSZDKNSLIKNSC-UHFFFAOYSA-N methyl 4-[2-[2-[1-(2-fluoroethyl)imidazol-4-yl]ethylcarbamoylamino]-4-methyl-1,3-thiazol-5-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=C(C)N=C(NC(=O)NCCC=2N=CN(CCF)C=2)S1 QXSZDKNSLIKNSC-UHFFFAOYSA-N 0.000 claims 1
- PSVYRZCYNDFRFY-UHFFFAOYSA-N methyl 4-[2-[[3-(2,2-difluoroethylamino)-3-oxopropyl]carbamoylamino]-4-methyl-1,3-thiazol-5-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=C(C)N=C(NC(=O)NCCC(=O)NCC(F)F)S1 PSVYRZCYNDFRFY-UHFFFAOYSA-N 0.000 claims 1
- CLMRTFRKPSDGLU-UHFFFAOYSA-N methyl 4-[4-methyl-2-[2-(1-propan-2-ylimidazol-4-yl)ethylcarbamoylamino]-1,3-thiazol-5-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=C(C)N=C(NC(=O)NCCC=2N=CN(C=2)C(C)C)S1 CLMRTFRKPSDGLU-UHFFFAOYSA-N 0.000 claims 1
- PDLKZEZWUXCZHQ-UHFFFAOYSA-N n-(2,2-difluoroethyl)-3-[[4-methyl-5-(1-oxo-2,3-dihydroinden-5-yl)-1,3-thiazol-2-yl]carbamoylamino]propanamide Chemical compound N1=C(NC(=O)NCCC(=O)NCC(F)F)SC(C=2C=C3CCC(=O)C3=CC=2)=C1C PDLKZEZWUXCZHQ-UHFFFAOYSA-N 0.000 claims 1
- LGAUHUITMSZZSU-UHFFFAOYSA-N n-(2,2-difluoroethyl)-3-[[4-methyl-5-(4-propanoylphenyl)-1,3-thiazol-2-yl]carbamoylamino]propanamide Chemical compound C1=CC(C(=O)CC)=CC=C1C1=C(C)N=C(NC(=O)NCCC(=O)NCC(F)F)S1 LGAUHUITMSZZSU-UHFFFAOYSA-N 0.000 claims 1
- XWBAXCSCOCLNLL-UHFFFAOYSA-N n-cyclopropyl-4-[2-[[3-(2-fluoroethylamino)-3-oxopropyl]carbamoylamino]-4-methyl-1,3-thiazol-5-yl]benzamide Chemical compound N1=C(NC(=O)NCCC(=O)NCCF)SC(C=2C=CC(=CC=2)C(=O)NC2CC2)=C1C XWBAXCSCOCLNLL-UHFFFAOYSA-N 0.000 claims 1
- BCJZOLIKFRGVGG-UHFFFAOYSA-N n-cyclopropyl-4-[4-methyl-2-[[3-oxo-3-(2,2,2-trifluoroethylamino)propyl]carbamoylamino]-1,3-thiazol-5-yl]benzamide Chemical compound N1=C(NC(=O)NCCC(=O)NCC(F)(F)F)SC(C=2C=CC(=CC=2)C(=O)NC2CC2)=C1C BCJZOLIKFRGVGG-UHFFFAOYSA-N 0.000 claims 1
- IACWHOXYPATOQV-UHFFFAOYSA-N n-methoxy-n-methyl-4-[4-methyl-2-[2-(1-propan-2-ylimidazol-4-yl)ethylcarbamoylamino]-1,3-thiazol-5-yl]benzamide Chemical compound C1=CC(C(=O)N(C)OC)=CC=C1C1=C(C)N=C(NC(=O)NCCC=2N=CN(C=2)C(C)C)S1 IACWHOXYPATOQV-UHFFFAOYSA-N 0.000 claims 1
- HCJXZXZUBLJWGS-UHFFFAOYSA-N n-tert-butyl-3-[[4-methyl-5-(4-propanoylphenyl)-1,3-thiazol-2-yl]carbamoylamino]propanamide Chemical compound C1=CC(C(=O)CC)=CC=C1C1=C(C)N=C(NC(=O)NCCC(=O)NC(C)(C)C)S1 HCJXZXZUBLJWGS-UHFFFAOYSA-N 0.000 claims 1
- OJHJYNHUZGMLMB-UHFFFAOYSA-N n-tert-butyl-3-[[5-[4-(cyclopropanecarbonyl)phenyl]-4-methyl-1,3-thiazol-2-yl]carbamoylamino]propanamide Chemical compound N1=C(NC(=O)NCCC(=O)NC(C)(C)C)SC(C=2C=CC(=CC=2)C(=O)C2CC2)=C1C OJHJYNHUZGMLMB-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 12
- 201000010099 disease Diseases 0.000 abstract description 11
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 abstract description 5
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 5
- 108091007960 PI3Ks Proteins 0.000 abstract description 3
- 230000001404 mediated effect Effects 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 38
- 239000000203 mixture Substances 0.000 description 26
- 208000006673 asthma Diseases 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 16
- 239000003814 drug Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000005557 antagonist Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 5
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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| GBGB0525671.4A GB0525671D0 (en) | 2005-12-16 | 2005-12-16 | Organic compounds |
| PCT/EP2006/012018 WO2007068473A2 (en) | 2005-12-16 | 2006-12-13 | Organic compounds |
Publications (2)
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| JP2009519280A true JP2009519280A (ja) | 2009-05-14 |
| JP2009519280A5 JP2009519280A5 (enExample) | 2012-02-02 |
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| US (1) | US7754746B2 (enExample) |
| EP (2) | EP1966175A2 (enExample) |
| JP (1) | JP2009519280A (enExample) |
| KR (1) | KR20080068744A (enExample) |
| CN (1) | CN101374823A (enExample) |
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| GB (1) | GB0525671D0 (enExample) |
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| WO (1) | WO2007068473A2 (enExample) |
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| MY156407A (en) * | 2002-02-28 | 2016-02-26 | Novartis Ag | 5-phenylthiazole derivatives and use as p13 kinase inhibitors |
| TW200519106A (en) | 2003-05-02 | 2005-06-16 | Novartis Ag | Organic compounds |
| GB0610243D0 (en) | 2006-05-23 | 2006-07-05 | Novartis Ag | Organic compounds |
| WO2009080694A1 (en) * | 2007-12-20 | 2009-07-02 | Novartis Ag | Thiazole derivatives used as pi 3 kinase inhibitors |
| CN102186822A (zh) | 2008-08-29 | 2011-09-14 | 顶标公司 | 新脲和硫脲衍生物 |
| UA104147C2 (uk) | 2008-09-10 | 2014-01-10 | Новартис Аг | Похідна піролідиндикарбонової кислоти та її застосування у лікуванні проліферативних захворювань |
| US8293753B2 (en) | 2009-07-02 | 2012-10-23 | Novartis Ag | Substituted 2-carboxamide cycloamino ureas |
| EA201200087A1 (ru) | 2009-07-02 | 2012-07-30 | Новартис Аг | 2-карбоксамиды циклоаминомочевин, которые являются ингибиторами pi3k |
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| WO2003072557A1 (en) * | 2002-02-28 | 2003-09-04 | Novartis Ag | 5-phenylthiazole derivatives and use as pi3 kinase inhibitors |
| WO2005021519A2 (en) * | 2003-08-28 | 2005-03-10 | Novartis Ag | 5-phenyl-4-methyl-thiazol-2-yl-amine derivatives as inhibitors of phosphatidylinositol 3 kinase enzymes (pi3) for the treatment of inflammatory airway diseases |
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| US5451700A (en) | 1991-06-11 | 1995-09-19 | Ciba-Geigy Corporation | Amidino compounds, their manufacture and methods of treatment |
| US6166037A (en) | 1997-08-28 | 2000-12-26 | Merck & Co., Inc. | Pyrrolidine and piperidine modulators of chemokine receptor activity |
| GB9913083D0 (en) | 1999-06-04 | 1999-08-04 | Novartis Ag | Organic compounds |
| PT1175402E (pt) | 1999-05-04 | 2005-11-30 | Schering Corp | Derivados da piperidina uteis como antagonistas ccr5 |
| CA2371583C (en) | 1999-05-04 | 2005-09-13 | Schering Corporation | Piperazine derivatives useful as ccr5 antagonists |
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2005
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2006
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- 2006-12-13 EP EP06840974A patent/EP1966175A2/en not_active Withdrawn
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- 2006-12-13 WO PCT/EP2006/012018 patent/WO2007068473A2/en not_active Ceased
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- 2006-12-13 JP JP2008544872A patent/JP2009519280A/ja active Pending
- 2006-12-13 CA CA002631051A patent/CA2631051A1/en not_active Abandoned
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2003072557A1 (en) * | 2002-02-28 | 2003-09-04 | Novartis Ag | 5-phenylthiazole derivatives and use as pi3 kinase inhibitors |
| WO2005021519A2 (en) * | 2003-08-28 | 2005-03-10 | Novartis Ag | 5-phenyl-4-methyl-thiazol-2-yl-amine derivatives as inhibitors of phosphatidylinositol 3 kinase enzymes (pi3) for the treatment of inflammatory airway diseases |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2008128566A (ru) | 2010-01-27 |
| AU2006326255A1 (en) | 2007-06-21 |
| GB0525671D0 (en) | 2006-01-25 |
| BRPI0619835A2 (pt) | 2011-10-18 |
| CA2631051A1 (en) | 2007-06-21 |
| EP1966175A2 (en) | 2008-09-10 |
| EP2357179A1 (en) | 2011-08-17 |
| WO2007068473A3 (en) | 2007-08-23 |
| CN101374823A (zh) | 2009-02-25 |
| US7754746B2 (en) | 2010-07-13 |
| KR20080068744A (ko) | 2008-07-23 |
| WO2007068473A2 (en) | 2007-06-21 |
| US20080319033A1 (en) | 2008-12-25 |
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