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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2009001634A (es) | 2006-08-15 | 2009-02-25 | Novartis Ag | Compuestos heterociclicos adecuados para el tratamiento de enfermedades relacionadas con el nivel elevado de lipidos. |
| WO2008074835A1 (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 |
| WO2009073973A1 (en) * | 2007-12-11 | 2009-06-18 | Merck Frosst Canada Ltd. | Novel heteroaromatic compounds as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| WO2009103739A1 (en) * | 2008-02-20 | 2009-08-27 | Novartis Ag | Heterocyclic inhibitors of stearoyl-coa desaturase |
| GB0810913D0 (en) * | 2008-06-13 | 2008-07-23 | Smithkline Beecham Corp | Comppounds |
| US20110184027A1 (en) * | 2008-09-25 | 2011-07-28 | Glenmark Pharmaceuticals S.A. | Tissue selective stearoyl-coa desaturase 1 inhibitors and cell based screening assay for their identification |
| DE102008057344A1 (de) | 2008-11-14 | 2010-05-20 | Bayer Schering Pharma Aktiengesellschaft | Aminoalkyl-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 |
| DE102008057343A1 (de) | 2008-11-14 | 2010-05-20 | Bayer Schering Pharma Aktiengesellschaft | Heterocyclisch substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102009041242A1 (de) | 2009-09-11 | 2011-12-15 | Bayer Schering Pharma Aktiengesellschaft | Heterocyclisch substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102008057364A1 (de) | 2008-11-14 | 2010-05-20 | Bayer Schering Pharma Aktiengesellschaft | 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 |
| EP2398809B1 (en) | 2009-02-17 | 2015-07-08 | Merck Canada Inc. | Novel spiro compounds useful as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| EP2459568A4 (en) | 2009-07-28 | 2013-02-27 | Merck Frosst Canada Ltd | NEW SPIRO COMPOUNDS AS AN 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 |
| CN107266433A (zh) | 2010-11-09 | 2017-10-20 | 铁木医药有限公司 | sGC刺激剂 |
| US9358250B2 (en) | 2011-10-15 | 2016-06-07 | Genentech, Inc. | Methods of using SCD1 antagonists |
| CN106117194A (zh) | 2011-12-27 | 2016-11-16 | 铁木医药有限公司 | 可用作sgc刺激剂的2‑苄基、3‑(嘧啶‑2‑基)取代的吡唑类 |
| US9233102B2 (en) | 2012-03-07 | 2016-01-12 | Mayo Foundation For Medical Education And Research | Methods and materials for treating cancer |
| MX2014014174A (es) | 2012-05-22 | 2015-07-06 | Hoffmann La Roche | Inhibidores selectivos de celulas no diferenciadas. |
| 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 |
| WO2016022955A1 (en) | 2014-08-07 | 2016-02-11 | 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 |
| JP2019533022A (ja) | 2016-10-24 | 2019-11-14 | ユマニティ セラピューティクス，インコーポレーテッド | 化合物及びその使用 |
| EP3566055B1 (en) | 2017-01-06 | 2025-03-12 | Janssen Pharmaceutica NV | Scd inhibitor for the treatment of neurological disorders |
| CA3083000A1 (en) | 2017-10-24 | 2019-05-02 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
| WO2019183587A1 (en) | 2018-03-23 | 2019-09-26 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
| GEP20227433B (en) | 2018-04-26 | 2022-10-25 | Pfizer | 2-amino-pyridine or 2-amino-pyrimidine derivatives as cyclin dependent kinase inhibitors |
| WO2020154571A1 (en) | 2019-01-24 | 2020-07-30 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
| 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. |
| WO1998054164A1 (en) | 1997-05-30 | 1998-12-03 | Takeda Chemical Industries, Ltd. | Sulfonamide derivatives, their production and use |
| AU751139B2 (en) * | 1997-10-13 | 2002-08-08 | Astellas Pharma Inc. | Amide derivative |
| CA2320167A1 (en) | 1998-03-19 | 1999-09-23 | Steven R. Turner | 1,3,4-thiadiazoles useful for the treatment of cmv infections |
| 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 |
| WO2000033836A1 (en) | 1998-12-04 | 2000-06-15 | Ontogen Corporation | 5-membered heterocycles for the treatment of human diseases involving modulators of selectins |
| KR20020008127A (ko) * | 1999-03-15 | 2002-01-29 | 스티븐 에프. 웨인스톡 | 항균 활성을 갖는 6-ｏ-치환된 매크롤라이드 |
| US6054435A (en) | 1999-03-19 | 2000-04-25 | Abbott Laboratories | 6-O-substituted macrolides having antibacterial activity |
| WO2001060458A2 (en) | 2000-02-18 | 2001-08-23 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferase |
| AU2001243158A1 (en) | 2000-02-18 | 2001-08-27 | Merck And Co., Inc. | Inhibitors of prenyl-protein transferase |
| WO2001062954A2 (en) | 2000-02-24 | 2001-08-30 | Xenon Genetics, Inc. | Stearoyl-coa desaturase to identify triglyceride reducing therapeutic agents |
| EP1184442A1 (en) | 2000-08-30 | 2002-03-06 | Clariant International Ltd. | Liquid crystal mixture |
| ATE402262T1 (de) | 2000-09-26 | 2008-08-15 | Xenon Pharmaceuticals Inc | Verfahren und zusammensetzungen, die eine stearoyl-coa desuturase-hscd5 verwenden |
| EP1324990B1 (en) | 2000-09-29 | 2014-10-29 | Glaxo Group Limited | Morpholin-acetamide derivatives for the treatment of inflammatory diseases |
| 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 |
| US20040077557A1 (en) | 2000-12-21 | 2004-04-22 | Sulejman Ali | Macrolide antibiotics |
| 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 |
| HRP20040311A2 (en) | 2001-10-01 | 2005-02-28 | Bristol-Myers Squibb Company Cerep SA | Spiro-hydantoin compounds useful as anti-inflammatory agents |
| 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 |
| WO2004032848A2 (en) | 2002-10-04 | 2004-04-22 | Millennium Pharmaceuticals, Inc. | Pgd2 receptor antagonists 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 |
| WO2004062665A1 (en) | 2003-01-16 | 2004-07-29 | Sb Pharmco Puerto Rico Inc | Heteroaryl- substituted pyrrolo` 2, 3- b! pyridine derivatives as crf receptor antagonists |
| 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 |
| WO2004092177A1 (en) | 2003-04-09 | 2004-10-28 | Biogen Idec Ma Inc. | Triazolopyrazines and methods of making and using the same |
| WO2004089416A2 (en) | 2003-04-11 | 2004-10-21 | Novo Nordisk A/S | Combination of an 11beta-hydroxysteroid dehydrogenase type 1 inhibitor and an antihypertensive agent |
| ATE482747T1 (de) | 2003-04-11 | 2010-10-15 | High Point Pharmaceuticals Llc | Neue amide derivate und deren pharmazeutische verwendungen |
| JP2006522744A (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 | グルココルチコイド受容体アゴニスト療法に伴う副作用を最小化するための、１１β−ヒドロキシステロイドデヒドロゲナーゼ１型阻害剤およびグルココルチコイド受容体アゴニストを使用する併用療法 |
| CA2523336A1 (en) | 2003-04-30 | 2004-11-11 | Merck Frosst Canada Ltd. | 8-(3-biaryl)phenylquinoline phosphodiesterase-4-inhibitors |
| 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 |
| MXPA06001202A (es) | 2003-07-29 | 2006-08-31 | Xenon Pharmaceuticals Inc | Derivados piridilo y su uso como agentes terapeuticos. |
| CA2533900A1 (en) | 2003-07-30 | 2005-02-10 | Xenon Pharmaceuticals Inc. | Pyridyl derivatives and their use as therapeutic agents |
| US7456180B2 (en) | 2003-07-30 | 2008-11-25 | Xenon Pharmaceuticals Inc. | Piperazine derivatives and their use as therapeutic agents |
| CA2533897A1 (en) | 2003-07-30 | 2005-02-10 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
| US7754711B2 (en) | 2003-07-30 | 2010-07-13 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
| PL1648874T3 (pl) | 2003-07-30 | 2012-04-30 | Xenon Pharmaceuticals Inc | Pochodne piperazyny i ich zastosowanie jako środków leczniczych |
| 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 |
| NZ551468A (en) | 2003-12-24 | 2010-05-28 | Biota Scient Management | Polycyclic agents for the treatment of respiratory syncytial virus infections |
| 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 |
| 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 |
| GB0406279D0 (en) | 2004-03-19 | 2004-04-21 | Arrow Therapeutics Ltd | Therapeutic compounds |
| CA2561564A1 (en) | 2004-04-07 | 2005-10-27 | Millennium Pharmaceuticals, Inc. | Pgd2 receptor antagonists for the treatment of inflammatory diseases |
| US8134010B2 (en) * | 2004-05-05 | 2012-03-13 | Renopharm Ltd. | Thiazole-based nitric oxide donors having aryl substituent(s) and uses thereof |
| EP1753734A1 (en) | 2004-05-05 | 2007-02-21 | Renopharm Ltd. | Nitric oxide donors and uses thereof |
| EP1742627A4 (en) * | 2004-05-06 | 2009-08-26 | Plexxikon Inc | PDE4B HEMMER AND ITS USE |
| US20050256118A1 (en) * | 2004-05-12 | 2005-11-17 | Altenbach Robert J | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
| US7098222B2 (en) * | 2004-05-12 | 2006-08-29 | Abbott Laboratories | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
| KR100984459B1 (ko) * | 2004-07-02 | 2010-09-29 | 제넨테크, 인크. | Ｉａｐ의 억제제 |
| ATE537830T1 (de) | 2004-07-06 | 2012-01-15 | Xenon Pharmaceuticals Inc | Nicotinamid derivate und ihre verwendung als therapeutika |
| CA2575466A1 (en) | 2004-08-13 | 2006-02-23 | Genentech, Inc. | Thiazole based inhibitors of atp-utilizing enzymes |
| WO2006023931A2 (en) * | 2004-08-18 | 2006-03-02 | Takeda San Diego, Inc. | Kinase inhibitors |
| AU2005286728A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as mediators of stearoyl-CoA desaturase |
| AU2005286790A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Bicyclic heterocyclic derivatives and their use as inhibitors of stearoyl-CoA-desaturase (SCD) |
| MX2007003318A (es) | 2004-09-20 | 2007-05-18 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como agentes terapeuticos. |
| BRPI0515482A (pt) | 2004-09-20 | 2008-07-22 | Xenon Pharmaceuticals Inc | derivados heterocìclicos e seus usos como agentes terapêuticos |
| AU2005286647A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| MX2007003332A (es) | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de estearoil-coa-desaturasa. |
| EP1827438B2 (en) | 2004-09-20 | 2014-12-10 | Xenon Pharmaceuticals Inc. | Piperazin derivatives for inhibiting human stearoyl-coa-desaturase |
| 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 |
| BRPI0515500A (pt) | 2004-09-20 | 2008-07-29 | Xenon Pharmaceuticals Inc | derivados piridazina para inibição de estearoil-coa-desaturase |
| WO2006051704A1 (ja) * | 2004-11-15 | 2006-05-18 | Taisho Pharmaceutical Co., Ltd. | 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 |
| UA92746C2 (en) | 2005-05-09 | 2010-12-10 | Акилайон Фармасьютикалз, Инк. | Thiazole compounds and methods of use |
| PL1879573T3 (pl) | 2005-05-10 | 2013-05-31 | Incyte Holdings Corp | Modulatory 2,3-dioksygenazy indoloaminy i sposoby ich zastosowania |
| WO2006125180A1 (en) | 2005-05-19 | 2006-11-23 | Xenon Pharmaceuticals Inc. | Piperazine derivatives and their uses as therapeutic agents |
| WO2007046868A2 (en) | 2005-05-19 | 2007-04-26 | Xenon Pharmaceuticals Inc. | Thiazolidine derivatives 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 |
| WO2007050124A1 (en) | 2005-05-19 | 2007-05-03 | Xenon Pharmaceuticals Inc. | Fused piperidine derivatives and their uses as therapeutic agents |
| WO2007044085A2 (en) | 2005-05-19 | 2007-04-19 | Xenon Pharmaceuticals Inc. | Heteroaryl 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 |
| WO2006125194A2 (en) | 2005-05-19 | 2006-11-23 | Xenon Pharmaceuticals Inc. | Piperazine 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 |
| WO2007046867A2 (en) | 2005-05-19 | 2007-04-26 | Xenon Pharmaceuticals Inc. | Piperidine 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 |
| EP1894930A4 (en) | 2005-06-23 | 2010-06-23 | Kyowa Hakko Kirin Co Ltd | THIAZOLE DERIVATIVE |
| US20090118296A1 (en) | 2005-07-20 | 2009-05-07 | Merck Frosst Canada Ltd. | Heteroaromatic Compounds As Inhibitors Of Stearoyl-Coenzyme A Delta-9 Desaturase |
| US7928098B2 (en) | 2005-08-02 | 2011-04-19 | Kyowa Hakko Kirin Co., Ltd. | Therapeutic and/or preventive agents for a sleep disorder |
| JP2007126454A (ja) | 2005-10-06 | 2007-05-24 | Taisho Pharmaceut Co Ltd | アニリド誘導体 |
| AU2006315025A1 (en) | 2005-11-15 | 2007-05-24 | Merck Frosst Canada Ltd. | Azacyclohexane derivatives as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| CA2632021A1 (en) | 2005-12-23 | 2007-06-28 | Astrazeneca Ab | Gaba-b receptor modulators |
| WO2007087429A2 (en) | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Phenyl and pyridyl compounds for inflammation and immune-related uses |
| SG176477A1 (en) * | 2006-08-07 | 2011-12-29 | Ironwood Pharmaceuticals Inc | Indole compounds |
-
2007
- 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 JP JP2009525617A patent/JP2010501567A/ja active Pending
- 2007-08-22 AU AU2007288245A patent/AU2007288245A1/en not_active Abandoned
- 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 CN CN200780031571XA patent/CN101506203B/zh not_active Expired - Fee Related
- 2007-08-22 RU RU2009110254/04A patent/RU2009110254A/ru not_active Application Discontinuation
- 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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