JP2010501567A5 - - Google Patents
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- JP2010501567A5 JP2010501567A5 JP2009525617A JP2009525617A JP2010501567A5 JP 2010501567 A5 JP2010501567 A5 JP 2010501567A5 JP 2009525617 A JP2009525617 A JP 2009525617A JP 2009525617 A JP2009525617 A JP 2009525617A JP 2010501567 A5 JP2010501567 A5 JP 2010501567A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- thiazole
- carboxylic acid
- pyrazol
- alkyl
- 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 54
- 125000003118 aryl group Chemical group 0.000 claims description 53
- 125000001072 heteroaryl group Chemical group 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 43
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 40
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 37
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 26
- 201000010099 disease Diseases 0.000 claims description 22
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 21
- 125000000304 alkynyl group Chemical group 0.000 claims description 20
- 108010087894 Fatty acid desaturases Proteins 0.000 claims description 18
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 16
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 16
- -1 trifluoromethoxyl Chemical group 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000001475 halogen functional group Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 125000004450 alkenylene group Chemical group 0.000 claims description 10
- 125000004419 alkynylene group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000003367 polycyclic group Chemical group 0.000 claims description 10
- 208000035475 disorder Diseases 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 4
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 102000016553 Stearoyl-CoA Desaturase Human genes 0.000 claims 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 4
- 101000631826 Homo sapiens Stearoyl-CoA desaturase Proteins 0.000 claims 3
- 102000055981 human SCD1 Human genes 0.000 claims 3
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 3
- 239000003446 ligand Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- BOSVIHWMSQFDEA-UHFFFAOYSA-N n-benzyl-2-[1-[2-(4-methoxyphenyl)ethyl]pyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1CCN1N=C(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC=CC=2)C=C1 BOSVIHWMSQFDEA-UHFFFAOYSA-N 0.000 claims 2
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 208000017520 skin disease Diseases 0.000 claims 2
- COFXNWIKPNAICQ-UHFFFAOYSA-N 2-[1-(2-anilinoethyl)pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCNC=3C=CC=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 COFXNWIKPNAICQ-UHFFFAOYSA-N 0.000 claims 1
- DESUOBUOHOUZSF-UHFFFAOYSA-N 2-[1-(2-cyclopropylethyl)pyrazol-3-yl]-n-[(4-fluorophenyl)methyl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCC3CC3)C=C2)SC=1C(=O)NCC1=CC=C(F)C=C1 DESUOBUOHOUZSF-UHFFFAOYSA-N 0.000 claims 1
- JROCFBGRHZCVEM-UHFFFAOYSA-N 2-[1-(2-hydroxyethyl)pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCO)C=C2)SC=1C(=O)NCC1=CC=CN=C1 JROCFBGRHZCVEM-UHFFFAOYSA-N 0.000 claims 1
- PASYEHCKCRQQPU-UHFFFAOYSA-N 2-[1-[(3,5-difluorophenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=C(F)C=C(F)C=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 PASYEHCKCRQQPU-UHFFFAOYSA-N 0.000 claims 1
- OGBAAAIKRBXTIV-UHFFFAOYSA-N 2-[1-[(3-chlorophenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=C(Cl)C=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 OGBAAAIKRBXTIV-UHFFFAOYSA-N 0.000 claims 1
- OKMKIHSFKTXQHZ-UHFFFAOYSA-N 2-[1-[(3-cyanophenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=C(C=CC=3)C#N)C=C2)SC=1C(=O)NCC1=CC=CN=C1 OKMKIHSFKTXQHZ-UHFFFAOYSA-N 0.000 claims 1
- FUJCGBTZOLHJSE-UHFFFAOYSA-N 2-[1-[(3-fluorophenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=C(F)C=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 FUJCGBTZOLHJSE-UHFFFAOYSA-N 0.000 claims 1
- WDABMXCIUPNKCF-UHFFFAOYSA-N 2-[1-[(4-chloro-2-fluorophenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C(=CC(Cl)=CC=3)F)C=C2)SC=1C(=O)NCC1=CC=CN=C1 WDABMXCIUPNKCF-UHFFFAOYSA-N 0.000 claims 1
- NVNBSOWRMZEZCP-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=CC(Cl)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 NVNBSOWRMZEZCP-UHFFFAOYSA-N 0.000 claims 1
- AKWDNTBINCFIOL-UHFFFAOYSA-N 2-[1-[(4-cyanophenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=CC(=CC=3)C#N)C=C2)SC=1C(=O)NCC1=CC=CN=C1 AKWDNTBINCFIOL-UHFFFAOYSA-N 0.000 claims 1
- UNFYXLDSTKSWOV-UHFFFAOYSA-N 2-[1-[(4-ethylphenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C1=CC(CC)=CC=C1CN1N=C(C=2SC(=C(C)N=2)C(=O)NCC=2C=NC=CC=2)C=C1 UNFYXLDSTKSWOV-UHFFFAOYSA-N 0.000 claims 1
- LJCCIMKJGXIMGS-UHFFFAOYSA-N 2-[1-[(4-fluorophenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 LJCCIMKJGXIMGS-UHFFFAOYSA-N 0.000 claims 1
- HUPGKCGSDFOLNY-UHFFFAOYSA-N 2-[1-[(4-tert-butylphenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=CC(=CC=3)C(C)(C)C)C=C2)SC=1C(=O)NCC1=CC=CN=C1 HUPGKCGSDFOLNY-UHFFFAOYSA-N 0.000 claims 1
- LYHDTGAYMNXTQQ-UHFFFAOYSA-N 2-[1-[2-(4-fluoroanilino)ethyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCNC=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 LYHDTGAYMNXTQQ-UHFFFAOYSA-N 0.000 claims 1
- ZLTCYIDFMSNXKL-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenoxy)ethyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCOC=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 ZLTCYIDFMSNXKL-UHFFFAOYSA-N 0.000 claims 1
- IBJROADCWLUKIU-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]-5-methylpyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC1=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=NC=CC=2)=NN1CCC1=CC=C(F)C=C1 IBJROADCWLUKIU-UHFFFAOYSA-N 0.000 claims 1
- CGTPBDCTPXABEE-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]-5-methylpyrazol-3-yl]-n-[(4-fluorophenyl)methyl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC1=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC(F)=CC=2)=NN1CCC1=CC=C(F)C=C1 CGTPBDCTPXABEE-UHFFFAOYSA-N 0.000 claims 1
- QLUWINQMTXITCQ-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]pyrazol-3-yl]-4-methyl-n-(2-pyridin-3-ylethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCC=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NCCC1=CC=CN=C1 QLUWINQMTXITCQ-UHFFFAOYSA-N 0.000 claims 1
- LWOSUYHAPVQEBO-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCC=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 LWOSUYHAPVQEBO-UHFFFAOYSA-N 0.000 claims 1
- XOHQYXIUZYTVJI-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]pyrazol-3-yl]-4-methyl-n-pyridin-3-yl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCC=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NC1=CC=CN=C1 XOHQYXIUZYTVJI-UHFFFAOYSA-N 0.000 claims 1
- LUBYVOZPGKDWPF-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]pyrazol-3-yl]-n-[(4-fluorophenyl)methyl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCC=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NCC1=CC=C(F)C=C1 LUBYVOZPGKDWPF-UHFFFAOYSA-N 0.000 claims 1
- IMFXAWNWSAISIS-UHFFFAOYSA-N 2-[1-[2-(4-methoxyphenyl)ethyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1CCN1N=C(C=2SC(=C(C)N=2)C(=O)NCC=2C=NC=CC=2)C=C1 IMFXAWNWSAISIS-UHFFFAOYSA-N 0.000 claims 1
- QTKLPOWQQUEGNX-UHFFFAOYSA-N 2-[1-[2-[(4-fluorobenzoyl)amino]ethyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCNC(=O)C=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 QTKLPOWQQUEGNX-UHFFFAOYSA-N 0.000 claims 1
- GSMOTFYLIZJFSZ-UHFFFAOYSA-N 2-[1-[2-[(4-fluorophenyl)sulfonylamino]ethyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCNS(=O)(=O)C=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 GSMOTFYLIZJFSZ-UHFFFAOYSA-N 0.000 claims 1
- WVYLATFUURTLHK-UHFFFAOYSA-N 2-[3-[4-methyl-5-(pyridin-3-ylmethylcarbamoyl)-1,3-thiazol-2-yl]pyrazol-1-yl]ethyl methanesulfonate Chemical compound CC=1N=C(C2=NN(CCOS(C)(=O)=O)C=C2)SC=1C(=O)NCC1=CC=CN=C1 WVYLATFUURTLHK-UHFFFAOYSA-N 0.000 claims 1
- FBQDWBGOZONRTQ-UHFFFAOYSA-N 2-[6-[(4-fluorophenyl)methyl-methylamino]pyrazin-2-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C=1N=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=NC=CC=2)=NC=1N(C)CC1=CC=C(F)C=C1 FBQDWBGOZONRTQ-UHFFFAOYSA-N 0.000 claims 1
- IHQVUTRLMXEZMM-UHFFFAOYSA-N 2-[6-[2-(4-fluorophenoxy)ethyl-methylamino]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound C=1N=CC(C=2SC(=C(C)N=2)C(O)=O)=NC=1N(C)CCOC1=CC=C(F)C=C1 IHQVUTRLMXEZMM-UHFFFAOYSA-N 0.000 claims 1
- COHIABZYSSAWPB-UHFFFAOYSA-N 2-[6-[2-(4-fluorophenyl)ethyl]pyrazin-2-yl]-n-[(4-fluorophenyl)methyl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(CCC=3C=CC(F)=CC=3)C=NC=2)SC=1C(=O)NCC1=CC=C(F)C=C1 COHIABZYSSAWPB-UHFFFAOYSA-N 0.000 claims 1
- LFQXILYITNIVCS-UHFFFAOYSA-N 2-[6-[[4-(difluoromethoxy)phenyl]methyl-methylamino]pyrazin-2-yl]-n-[(4-fluorophenyl)methyl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C=1N=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC(F)=CC=2)=NC=1N(C)CC1=CC=C(OC(F)F)C=C1 LFQXILYITNIVCS-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- NWAKIDXIIAQAQW-UHFFFAOYSA-N 4-methyl-2-[1-(2-phenoxyethyl)pyrazol-3-yl]-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCOC=3C=CC=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 NWAKIDXIIAQAQW-UHFFFAOYSA-N 0.000 claims 1
- XCNRBOGRGUYICM-UHFFFAOYSA-N 4-methyl-2-[1-(2-phenylpropyl)pyrazol-3-yl]-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C=1C=CC=CC=1C(C)CN(N=1)C=CC=1C(S1)=NC(C)=C1C(=O)NCC1=CC=CN=C1 XCNRBOGRGUYICM-UHFFFAOYSA-N 0.000 claims 1
- XCNRBOGRGUYICM-INIZCTEOSA-N 4-methyl-2-[1-[(2r)-2-phenylpropyl]pyrazol-3-yl]-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C([C@H](C)C=1C=CC=CC=1)N(N=1)C=CC=1C(S1)=NC(C)=C1C(=O)NCC1=CC=CN=C1 XCNRBOGRGUYICM-INIZCTEOSA-N 0.000 claims 1
- XCNRBOGRGUYICM-MRXNPFEDSA-N 4-methyl-2-[1-[(2s)-2-phenylpropyl]pyrazol-3-yl]-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C([C@@H](C)C=1C=CC=CC=1)N(N=1)C=CC=1C(S1)=NC(C)=C1C(=O)NCC1=CC=CN=C1 XCNRBOGRGUYICM-MRXNPFEDSA-N 0.000 claims 1
- ANIJWYCYCAMXLW-UHFFFAOYSA-N 4-methyl-2-[1-[(4-methylsulfonylphenyl)methyl]pyrazol-3-yl]-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=CC(=CC=3)S(C)(=O)=O)C=C2)SC=1C(=O)NCC1=CC=CN=C1 ANIJWYCYCAMXLW-UHFFFAOYSA-N 0.000 claims 1
- GRCRTBQDOQHLNV-UHFFFAOYSA-N 4-methyl-2-[1-[(4-pyrazol-1-ylphenyl)methyl]pyrazol-3-yl]-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=CC(=CC=3)N3N=CC=C3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 GRCRTBQDOQHLNV-UHFFFAOYSA-N 0.000 claims 1
- SVALBOALYAAMBS-UHFFFAOYSA-N 4-methyl-2-[1-[2-(n-methylanilino)ethyl]pyrazol-3-yl]-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C=1C=CC=CC=1N(C)CCN(N=1)C=CC=1C(S1)=NC(C)=C1C(=O)NCC1=CC=CN=C1 SVALBOALYAAMBS-UHFFFAOYSA-N 0.000 claims 1
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Families Citing this family (32)
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|---|---|---|---|---|
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| CA2672776A1 (en) * | 2006-12-20 | 2008-06-26 | Novartis Ag | 2-substituted 5-membered heterocycles as scd inhibitors |
| WO2008128335A1 (en) * | 2007-04-20 | 2008-10-30 | Merck Frosst Canada Ltd. | Novel heteroaromatic compounds as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| EP2231649A4 (en) * | 2007-12-11 | 2010-12-22 | Merck Frosst Canada Ltd | NEW HETEROAROMATIC COMPOUNDS AS INHIBITORS OF STEAROYL-COENZYME-A-DELTA-9-DESATURASE |
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| GB0810913D0 (en) * | 2008-06-13 | 2008-07-23 | Smithkline Beecham Corp | Comppounds |
| WO2010035052A1 (en) * | 2008-09-25 | 2010-04-01 | Glenmark Pharmaceuticals, S.A. | Tissue selective stearoyl-coa desaturase 1 inhibitors and cell based screening assay for their identification |
| DE102009041242A1 (de) | 2009-09-11 | 2011-12-15 | Bayer Schering Pharma Aktiengesellschaft | Heterocyclisch substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102008057343A1 (de) | 2008-11-14 | 2010-05-20 | Bayer Schering Pharma Aktiengesellschaft | Heterocyclisch substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102008057344A1 (de) | 2008-11-14 | 2010-05-20 | Bayer Schering Pharma Aktiengesellschaft | Aminoalkyl-substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102008057364A1 (de) | 2008-11-14 | 2010-05-20 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102009041241A1 (de) | 2009-09-11 | 2011-08-04 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Substituierte Aryl-Verbindungen und ihre Verwendung |
| FR2938538B1 (fr) * | 2008-11-17 | 2011-08-05 | Univ Nice Sophia Antipolis | Procede de preparation d'acides et d'esters boroniques en presence de magnesium metallique |
| WO2010094120A1 (en) | 2009-02-17 | 2010-08-26 | Merck Frosst Canada Ltd. | Novel spiro compounds useful as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| WO2011011872A1 (en) | 2009-07-28 | 2011-02-03 | Merck Frosst Canada Ltd. | Novel spiro compounds useful as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| BR112012007509A2 (pt) * | 2009-10-01 | 2016-11-22 | Novartis Ag | derivados pirazóis que modulam estearoil-coa dessaturase |
| EP2588465B1 (en) | 2010-06-30 | 2017-01-25 | Ironwood Pharmaceuticals, Inc. | Sgc stimulators |
| CN103402515B (zh) | 2010-11-09 | 2017-05-17 | 铁木医药有限公司 | sGC刺激剂 |
| CA2850836A1 (en) | 2011-10-15 | 2013-04-18 | Genentech, Inc. | Methods of using scd1 antagonists |
| CA2861804C (en) | 2011-12-27 | 2021-10-26 | Ironwood Pharmaceuticals, Inc. | 2-benzyl,3(pyrimidin-2-yl)substituted pyrazoles useful as sgc stimulators |
| WO2013134546A1 (en) | 2012-03-07 | 2013-09-12 | Mayo Foundation For Medical Education And Research | Methods and materials for treating cancer |
| BR112014029365A2 (pt) | 2012-05-22 | 2017-06-27 | Hoffmann La Roche | inibidores seletivos de células indiferenciadas |
| CN103694195B (zh) * | 2013-09-18 | 2016-04-06 | 华东师范大学 | 芳香杂环类小分子有机化合物及衍生物、制备方法及医药用途 |
| EP3177292B1 (en) | 2014-08-07 | 2020-11-25 | Mayo Foundation for Medical Education and Research | Compounds and methods for treating cancer |
| WO2016101118A1 (en) * | 2014-12-23 | 2016-06-30 | Merck Sharp & Dohme Corp. | Amidoethyl azole orexin receptor antagonists |
| CN110099898B (zh) | 2016-10-24 | 2023-07-25 | 优曼尼蒂治疗公司 | 化合物及其用途 |
| CN110392833A (zh) | 2017-01-06 | 2019-10-29 | 优曼尼蒂治疗公司 | 治疗神经病症的方法 |
| WO2019084157A1 (en) | 2017-10-24 | 2019-05-02 | Yumanity Therapeutics, Inc. | COMPOUNDS AND USES THEREOF |
| CN112312913B (zh) | 2018-03-23 | 2024-03-08 | 詹森药业有限公司 | 化合物和其用途 |
| EP3784664B1 (en) | 2018-04-26 | 2025-02-19 | Pfizer Inc. | 2-amino-pyridine or 2-amino-pyrimidine derivatives as cyclin dependent kinase inhibitors |
| CN113906019A (zh) | 2019-01-24 | 2022-01-07 | 优曼尼蒂治疗公司 | 化合物及其用途 |
| EA202192047A1 (ru) | 2019-11-13 | 2021-12-08 | Юманити Терапьютикс, Инк. | Соединения и их применение |
Family Cites Families (100)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4659726A (en) | 1984-04-19 | 1987-04-21 | Kanebo, Ltd. | Novel 4,5-Bis (4-methoxyphenyl)-2-(pyrrol-2-yl) thiazoles and pharmaceutical composition containing the same |
| IL96891A0 (en) | 1990-01-17 | 1992-03-29 | Merck Sharp & Dohme | Indole-substituted five-membered heteroaromatic compounds,their preparation and pharmaceutical compositions containing them |
| EP0471201A1 (de) | 1990-07-21 | 1992-02-19 | Hoechst Aktiengesellschaft | Neue Oxazolidinon-Derivate und ihre Verwendung als Dotierstoffe in Flüssigkristallmischungen |
| JPH04247076A (ja) | 1991-02-01 | 1992-09-03 | Canon Inc | 液晶性化合物、これを含む液晶組成物、およびその使用方法、それを使用した液晶素子、表示装置 |
| EP0520292A1 (de) | 1991-06-19 | 1992-12-30 | Hoechst Aktiengesellschaft | Chirale Azetidinon-Derivate und ihre Verwendung als Dotierstoffe in Flüssigkristallmischungen |
| IT1254199B (it) | 1992-02-06 | 1995-09-14 | Ministero Dell Uni E Della | Tiazolilpirroli ad attivita' fungicida |
| US5254576A (en) * | 1992-04-03 | 1993-10-19 | Bristol-Myers Squibb Company | Diphenyl-heterocyclic-oxazole as platelet aggregation inhibitors |
| DE4302051A1 (de) | 1993-01-26 | 1994-07-28 | Thomae Gmbh Dr K | 5-gliedrige Heterocyclen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| JP3377826B2 (ja) | 1993-05-06 | 2003-02-17 | ヘキスト・アクチェンゲゼルシャフト | 液晶組成物に使用するための新規化合物 |
| FR2707295A1 (fr) * | 1993-06-07 | 1995-01-13 | Rhone Poulenc Agrochimie | Fongicides pyrazoles substitués en position 3 par un hétérocycle. |
| EP0986551B1 (en) | 1997-05-30 | 2006-08-02 | Takeda Pharmaceutical Company Limited | Sulfonamide derivatives, their production and use |
| AU751139B2 (en) * | 1997-10-13 | 2002-08-08 | Astellas Pharma Inc. | Amide derivative |
| DK1064273T3 (da) | 1998-03-19 | 2003-03-31 | Upjohn Co | 1,3,4-Thiadiazoler, som er nyttige til behandling af CMV-infektioner |
| US6399656B1 (en) * | 1998-07-28 | 2002-06-04 | Smithkline Beecham Corporation | Compounds and methods |
| EP1126833A4 (en) | 1998-10-29 | 2004-09-08 | Trega Biosciences Inc | OXADIAZOLE, THIADIAZOLE AND TRIAZOLE DERIVATIVES AND COMBINATORIAL LIBRARIES CONTAINING THESE DERIVATIVES |
| AU2039800A (en) | 1998-12-04 | 2000-06-26 | Ontogen Corporation | 5-membered heterocycles for the treatment of human diseases involving modulatorsof selectins |
| WO2000055168A1 (en) * | 1999-03-15 | 2000-09-21 | Abbott Laboratories | 6-o-substituted macrolides having antibacterial activity |
| US6054435A (en) * | 1999-03-19 | 2000-04-25 | Abbott Laboratories | 6-O-substituted macrolides having antibacterial activity |
| AU2001238424A1 (en) | 2000-02-18 | 2001-08-27 | Merck And Co., Inc. | Inhibitors of prenyl-protein transferase |
| AU2001243158A1 (en) | 2000-02-18 | 2001-08-27 | Merck And Co., Inc. | Inhibitors of prenyl-protein transferase |
| ATE475718T1 (de) | 2000-02-24 | 2010-08-15 | Xenon Pharmaceuticals Inc | Stearoyl-coa-desaturase zur identifizierung von triglyceridreduktionstherapeutika |
| EP1184442A1 (en) | 2000-08-30 | 2002-03-06 | Clariant International Ltd. | Liquid crystal mixture |
| US7232662B2 (en) | 2000-09-26 | 2007-06-19 | Xenon Pharmaceuticals Inc. | Methods and compositions employing a novel stearoyl-CoA desaturase-hSCD5 |
| KR20030031198A (ko) | 2000-09-29 | 2003-04-18 | 글락소 그룹 리미티드 | 염증 질환 치료용 모르폴린-아세트아미드 유도체 |
| JP2002114784A (ja) * | 2000-10-06 | 2002-04-16 | Nissan Chem Ind Ltd | イソキサゾール誘導体および有害生物防除剤 |
| KR20030068189A (ko) | 2000-12-21 | 2003-08-19 | 글락소 그룹 리미티드 | 마크롤라이드계 항생제 |
| TWI243164B (en) * | 2001-02-13 | 2005-11-11 | Aventis Pharma Gmbh | Acylated indanyl amines and their use as pharmaceuticals |
| GB0122503D0 (en) | 2001-09-18 | 2001-11-07 | Astrazeneca Ab | Chemical compounds |
| BR0213025A (pt) | 2001-10-01 | 2004-10-05 | Bristol Myers Squibb Co | Compostos de espiro-hidantoìna úteis como agentes antiinflamatórios |
| US6824707B2 (en) | 2001-10-23 | 2004-11-30 | Clariant International Ltd. | Active matrix liquid crystal device and smectic liquid crystal mixture |
| GB0208579D0 (en) * | 2002-04-13 | 2002-05-22 | British Biotech Pharm | Antibacterial agents |
| TWI329111B (en) | 2002-05-24 | 2010-08-21 | X Ceptor Therapeutics Inc | Azepinoindole and pyridoindole derivatives as pharmaceutical agents |
| US7595311B2 (en) * | 2002-05-24 | 2009-09-29 | Exelixis, Inc. | Azepinoindole derivatives as pharmaceutical agents |
| EP1556047A4 (en) | 2002-10-04 | 2009-09-30 | Millennium Pharm Inc | ANTAGONISTS AGAINST THE PGD2 RECEPTOR FOR THE TREATMENT OF INFLAMMATORY DISEASES |
| US7504508B2 (en) * | 2002-10-04 | 2009-03-17 | Millennium Pharmaceuticals, Inc. | PGD2 receptor antagonists for the treatment of inflammatory diseases |
| ATE359782T1 (de) | 2003-01-16 | 2007-05-15 | Sb Pharmco Inc | Heteroaryl-substituierte pyrrol(2, 3- b)pyridin- derivate als crf-rezeptor-antagonisten |
| DE10306250A1 (de) * | 2003-02-14 | 2004-09-09 | Aventis Pharma Deutschland Gmbh | Substituierte N-Arylheterozyklen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| WO2004080972A1 (en) | 2003-03-12 | 2004-09-23 | Vertex Pharmaceuticals Incorporated | Pirazole modulators of atp-binding cassette transporters |
| US7674791B2 (en) | 2003-04-09 | 2010-03-09 | Biogen Idec Ma Inc. | Triazolopyrazines and methods of making and using the same |
| EP1615667A2 (en) | 2003-04-11 | 2006-01-18 | Novo Nordisk A/S | Combinations of an 11-beta-hydroxysteroid dehydrogenase type 1 inhibitor and a glucocorticoid receptor agonist |
| JP4629657B2 (ja) | 2003-04-11 | 2011-02-09 | ハイ・ポイント・ファーマスーティカルズ、エルエルシー | １１β−ヒドロキシステロイドデヒドロゲナーゼ１型化活性化合物 |
| JP2006522750A (ja) | 2003-04-11 | 2006-10-05 | ノボ ノルディスク アクティーゼルスカブ | 代謝性症候群ならびに関連の疾患および障害を治療するために、１１β−ヒドロキシステロイドデヒドロゲナーゼ１型阻害剤および抗高血圧剤を使用する併用療法 |
| JP2006524638A (ja) | 2003-04-30 | 2006-11-02 | メルク フロスト カナダ リミテツド | ８−（３−ビアリール）フェニルキノリン系ホスホジエステラーゼ−４阻害薬 |
| GB0320244D0 (en) | 2003-05-06 | 2003-10-01 | Aventis Pharma Inc | Pyrazoles as inhibitors of tumour necrosis factor |
| TWI372050B (en) | 2003-07-03 | 2012-09-11 | Astex Therapeutics Ltd | (morpholin-4-ylmethyl-1h-benzimidazol-2-yl)-1h-pyrazoles |
| BRPI0413059A (pt) | 2003-07-29 | 2006-10-31 | Xenon Pharmaceuticals Inc | derivados de piridila e seu uso como agentes terapêuticos |
| US7754711B2 (en) | 2003-07-30 | 2010-07-13 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
| CN101712653A (zh) | 2003-07-30 | 2010-05-26 | 泽农医药公司 | 哒嗪衍生物和它们作为治疗剂的用途 |
| CA2533899C (en) | 2003-07-30 | 2011-01-04 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
| AU2004261267B9 (en) | 2003-07-30 | 2009-04-09 | Xenon Pharmaceuticals Inc. | Pyridyl derivatives and their use as therapeutic agents |
| BRPI0412348A (pt) | 2003-07-30 | 2006-09-05 | Xenon Pharmaceuticals Inc | derivados de piperazina e seu uso como agentes terapêuticos |
| GB0325956D0 (en) | 2003-11-06 | 2003-12-10 | Addex Pharmaceuticals Sa | Novel compounds |
| CN1618796A (zh) | 2003-11-21 | 2005-05-25 | 吉林省药物研究所 | 4，5－二取代－2－（1－取代－1h－吡咯－2－基）－噻唑衍生物 |
| CN101723949B (zh) | 2003-12-24 | 2013-10-23 | 生物区科学管理控股有限公司 | 用于治疗呼吸道合胞体病毒感染的多环试剂 |
| GB0402496D0 (en) | 2004-02-04 | 2004-03-10 | Argenta Discovery Ltd | Novel compounds |
| RU2367661C2 (ru) | 2004-03-05 | 2009-09-20 | Тайсо Фармасьютикал Ко., Лтд. | Производные тиазола |
| GB0406279D0 (en) * | 2004-03-19 | 2004-04-21 | Arrow Therapeutics Ltd | Therapeutic compounds |
| GB0406280D0 (en) | 2004-03-19 | 2004-04-21 | Arrow Therapeutics Ltd | Chemical compounds |
| WO2005090319A1 (en) | 2004-03-19 | 2005-09-29 | Arrow Therapeutics Limited | Process for preparing benzodiazepines |
| EP1740547A1 (en) | 2004-04-07 | 2007-01-10 | Millennium Pharmaceuticals, Inc. | Pgd2 receptor antagonists for the treatment of inflammatory diseases |
| EP1753734A1 (en) | 2004-05-05 | 2007-02-21 | Renopharm Ltd. | Nitric oxide donors and uses thereof |
| US8134010B2 (en) * | 2004-05-05 | 2012-03-13 | Renopharm Ltd. | Thiazole-based nitric oxide donors having aryl substituent(s) and uses thereof |
| WO2006078287A2 (en) * | 2004-05-06 | 2006-07-27 | Plexxikon, Inc. | Pde4b inhibitors and uses therefor |
| US7098222B2 (en) * | 2004-05-12 | 2006-08-29 | Abbott Laboratories | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
| US20050256118A1 (en) * | 2004-05-12 | 2005-11-17 | Altenbach Robert J | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
| SI1778718T1 (sl) * | 2004-07-02 | 2015-01-30 | Genentech, Inc. | Inhibitorji IAP |
| WO2006014168A1 (en) | 2004-07-06 | 2006-02-09 | Xenon Pharmaceuticals Inc. | Nicotinamide derivatives and their use as therapeutic agents |
| CA2575466A1 (en) | 2004-08-13 | 2006-02-23 | Genentech, Inc. | Thiazole based inhibitors of atp-utilizing enzymes |
| EP1778669A2 (en) * | 2004-08-18 | 2007-05-02 | Takeda San Diego, Inc. | Kinase inhibitors |
| BRPI0515482A (pt) | 2004-09-20 | 2008-07-22 | Xenon Pharmaceuticals Inc | derivados heterocìclicos e seus usos como agentes terapêuticos |
| US7951805B2 (en) | 2004-09-20 | 2011-05-31 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as mediators of stearoyl-CoA desaturase |
| JP4958784B2 (ja) | 2004-09-20 | 2012-06-20 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | ステアロイル−ＣｏＡデサチュラーゼ酵素によって媒介される疾患の処置のための複素環誘導体 |
| MX2007003332A (es) | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de estearoil-coa-desaturasa. |
| AR051094A1 (es) | 2004-09-20 | 2006-12-20 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de la estearoil-coa desaturasa |
| JP4958787B2 (ja) | 2004-09-20 | 2012-06-20 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | ヒトステアロイル−ＣｏＡデサチュラーゼを阻害するためのピリジン誘導体 |
| CN101084211A (zh) | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 杂环衍生物及其作为治疗剂的用途 |
| CA2580855A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| BRPI0515477A (pt) | 2004-09-20 | 2008-07-22 | Xenon Pharmaceuticals Inc | derivados heterocìclicos bicìclicos e o uso dos mesmos como inibidores de estaroil-coa-desaturase (scd) |
| JPWO2006051704A1 (ja) * | 2004-11-15 | 2008-05-29 | 大正製薬株式会社 | イミン化合物 |
| CN1834095B (zh) * | 2005-03-18 | 2011-04-20 | 中国科学院上海药物研究所 | 一类非核苷类抗病毒抑制剂及其制备方法和用途 |
| AP2358A (en) | 2005-05-09 | 2012-01-30 | Achillion Pharmaceuticals Inc | Thiazole compounds and methods of use. |
| SG10201809390QA (en) * | 2005-05-10 | 2018-11-29 | Incyte Holdings Corp | Modulators of indoleamine 2,3-dioxygenase and methods of using the same |
| WO2007044085A2 (en) | 2005-05-19 | 2007-04-19 | Xenon Pharmaceuticals Inc. | Heteroaryl compounds and their uses as therapeutic agents |
| WO2007050124A1 (en) | 2005-05-19 | 2007-05-03 | Xenon Pharmaceuticals Inc. | Fused piperidine derivatives and their uses as therapeutic agents |
| WO2006125180A1 (en) | 2005-05-19 | 2006-11-23 | Xenon Pharmaceuticals Inc. | Piperazine derivatives and their uses as therapeutic agents |
| WO2007046867A2 (en) | 2005-05-19 | 2007-04-26 | Xenon Pharmaceuticals Inc. | Piperidine derivatives and their uses as therapeutic agents |
| WO2006125178A2 (en) | 2005-05-19 | 2006-11-23 | Xenon Pharmaceuticals Inc. | Tricyclic pyridazine compounds and their uses as therapeutic agents |
| WO2006125179A1 (en) | 2005-05-19 | 2006-11-23 | Xenon Pharmaceuticals Inc. | Tricyclic compounds and their uses as therapeutic agents |
| WO2006125181A2 (en) | 2005-05-19 | 2006-11-23 | Xenon Pharmaceuticals Inc. | Piperidine derivatives and their use as stearoyl-coa desaturase modulators |
| WO2007046868A2 (en) | 2005-05-19 | 2007-04-26 | Xenon Pharmaceuticals Inc. | Thiazolidine derivatives and their uses as therapeutic agents |
| WO2006125194A2 (en) | 2005-05-19 | 2006-11-23 | Xenon Pharmaceuticals Inc. | Piperazine derivatives and their uses as therapeutic agents |
| CA2610196A1 (en) | 2005-06-09 | 2006-12-14 | Merck Frosst Canada Ltd. | Azacyclohexane derivatives as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| WO2006137527A1 (ja) | 2005-06-23 | 2006-12-28 | Kyowa Hakko Kogyo Co., Ltd. | チアゾール誘導体 |
| WO2007009236A1 (en) | 2005-07-20 | 2007-01-25 | Merck Frosst Canada Ltd. | Heteroaromatic compounds as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| DK1921077T3 (en) | 2005-08-02 | 2017-10-23 | Kyowa Hakko Kirin Co Ltd | Means for treating and / or preventing sleep disorders |
| JP2007126454A (ja) * | 2005-10-06 | 2007-05-24 | Taisho Pharmaceut Co Ltd | アニリド誘導体 |
| WO2007056846A1 (en) | 2005-11-15 | 2007-05-24 | Merck Frosst Canada Ltd. | Azacyclohexane derivatives as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| BRPI0620464A2 (pt) * | 2005-12-23 | 2011-11-16 | Astrazeneca Ab | composto, composição farmacêutica, uso de um composto, e, método para o tratamento de uma doença |
| EP1983831A4 (en) | 2006-01-25 | 2010-11-24 | Synta Pharmaceuticals Corp | PHENYL AND PYRIDIL COMPOUNDS FOR INFLAMMATION AND IMMUNOUS USE |
| EP2049520A4 (en) * | 2006-08-07 | 2011-01-05 | Ironwood Pharmaceuticals Inc | indole compounds |
-
2007
- 2007-08-22 RU RU2009110254/04A patent/RU2009110254A/ru not_active Application Discontinuation
- 2007-08-22 AU AU2007288245A patent/AU2007288245A1/en not_active Abandoned
- 2007-08-22 MX MX2009002019A patent/MX2009002019A/es not_active Application Discontinuation
- 2007-08-22 WO PCT/US2007/018554 patent/WO2008024390A2/en not_active Ceased
- 2007-08-22 BR BRPI0719122-7A patent/BRPI0719122A2/pt not_active Application Discontinuation
- 2007-08-22 CN CN200780031571XA patent/CN101506203B/zh not_active Expired - Fee Related
- 2007-08-22 JP JP2009525617A patent/JP2010501567A/ja active Pending
- 2007-08-22 EP EP07811474.1A patent/EP2086970B1/en not_active Not-in-force
- 2007-08-22 KR KR1020097005864A patent/KR20090040478A/ko not_active Withdrawn
- 2007-08-22 US US12/438,654 patent/US8314138B2/en not_active Expired - Fee Related
- 2007-08-22 CA CA002661017A patent/CA2661017A1/en not_active Abandoned
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