CA2661017A1 - Organic compounds - Google Patents
Organic compounds Download PDFInfo
- Publication number
- CA2661017A1 CA2661017A1 CA002661017A CA2661017A CA2661017A1 CA 2661017 A1 CA2661017 A1 CA 2661017A1 CA 002661017 A CA002661017 A CA 002661017A CA 2661017 A CA2661017 A CA 2661017A CA 2661017 A1 CA2661017 A1 CA 2661017A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- thiazole
- carboxylic acid
- pyrazol
- fluoro
- 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.)
- Abandoned
Links
- 150000002894 organic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 276
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 107
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 104
- 108010087894 Fatty acid desaturases Proteins 0.000 claims abstract description 100
- 201000010099 disease Diseases 0.000 claims abstract description 74
- 230000001404 mediated effect Effects 0.000 claims abstract description 36
- 239000003112 inhibitor Substances 0.000 claims abstract description 22
- 208000008589 Obesity Diseases 0.000 claims abstract description 15
- 235000020824 obesity Nutrition 0.000 claims abstract description 15
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 12
- 208000001145 Metabolic Syndrome Diseases 0.000 claims abstract description 11
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 102000016553 Stearoyl-CoA Desaturase Human genes 0.000 claims abstract 8
- 125000000217 alkyl group Chemical group 0.000 claims description 169
- 125000003118 aryl group Chemical group 0.000 claims description 147
- -1 trifluoromethoxyl Chemical group 0.000 claims description 145
- 239000001257 hydrogen Substances 0.000 claims description 109
- 229910052739 hydrogen Inorganic materials 0.000 claims description 109
- 125000001072 heteroaryl group Chemical group 0.000 claims description 108
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 102
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 97
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 95
- 238000000034 method Methods 0.000 claims description 72
- 239000002253 acid Substances 0.000 claims description 61
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 57
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 54
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 53
- 230000000694 effects Effects 0.000 claims description 45
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 44
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 claims description 44
- 125000002947 alkylene group Chemical group 0.000 claims description 43
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 38
- 125000000304 alkynyl group Chemical group 0.000 claims description 38
- 125000003342 alkenyl group Chemical group 0.000 claims description 36
- 125000001188 haloalkyl group Chemical group 0.000 claims description 36
- 239000008194 pharmaceutical composition Substances 0.000 claims description 30
- 208000035475 disorder Diseases 0.000 claims description 29
- 125000004450 alkenylene group Chemical group 0.000 claims description 23
- 150000001408 amides Chemical class 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 229940002612 prodrug Drugs 0.000 claims description 20
- 239000000651 prodrug Substances 0.000 claims description 20
- 125000004419 alkynylene group Chemical group 0.000 claims description 19
- 241000124008 Mammalia Species 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- MBALKBRJRNEXCS-UHFFFAOYSA-N n-benzyl-4-methyl-2-(1h-pyrazol-5-yl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2NN=CC=2)SC=1C(=O)NCC1=CC=CC=C1 MBALKBRJRNEXCS-UHFFFAOYSA-N 0.000 claims description 12
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 230000005764 inhibitory process Effects 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 9
- 239000003446 ligand Substances 0.000 claims description 7
- 206010022489 Insulin Resistance Diseases 0.000 claims description 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 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 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 5
- 230000037396 body weight Effects 0.000 claims description 4
- 239000008103 glucose Substances 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 206010023330 Keloid scar Diseases 0.000 claims description 3
- 102000016267 Leptin Human genes 0.000 claims description 3
- 108010092277 Leptin Proteins 0.000 claims description 3
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 3
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 3
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 claims description 3
- 229940039781 leptin Drugs 0.000 claims description 3
- RRLZEMBDKSCPJD-UHFFFAOYSA-N n-benzyl-2-(5-bromopyrazin-2-yl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=CC(Br)=NC=2)SC=1C(=O)NCC1=CC=CC=C1 RRLZEMBDKSCPJD-UHFFFAOYSA-N 0.000 claims description 3
- JYLRTPHRXNYQKP-UHFFFAOYSA-N n-benzyl-2-[6-(dimethylamino)pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CN(C)C1=CN=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC=CC=2)=N1 JYLRTPHRXNYQKP-UHFFFAOYSA-N 0.000 claims description 3
- KQYPATXQBASHAJ-UHFFFAOYSA-N n-benzyl-4-methyl-2-[6-(3-phenylpropyl)pyrazin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(CCCC=3C=CC=CC=3)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 KQYPATXQBASHAJ-UHFFFAOYSA-N 0.000 claims description 3
- 235000001968 nicotinic acid Nutrition 0.000 claims description 3
- 239000011664 nicotinic acid Substances 0.000 claims description 3
- 229960003512 nicotinic acid Drugs 0.000 claims description 3
- 208000017520 skin disease Diseases 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- 201000005665 thrombophilia Diseases 0.000 claims description 3
- 208000016261 weight loss Diseases 0.000 claims description 3
- 230000004580 weight loss Effects 0.000 claims description 3
- 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 description 2
- 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 description 2
- SLZIHPKCNBTZQC-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]-5-methylpyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound CC1=CC(C=2SC(=C(C)N=2)C(O)=O)=NN1CCC1=CC=C(F)C=C1 SLZIHPKCNBTZQC-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- BSXIGERZJMTVML-UHFFFAOYSA-N 4-methyl-2-[5-methyl-1-[[4-(trifluoromethyl)phenyl]methyl]pyrazol-3-yl]-1,3-thiazole-5-carboxylic acid Chemical compound CC1=CC(C=2SC(=C(C)N=2)C(O)=O)=NN1CC1=CC=C(C(F)(F)F)C=C1 BSXIGERZJMTVML-UHFFFAOYSA-N 0.000 claims description 2
- VZBHCJJQVKGFSC-UHFFFAOYSA-N 4-methyl-n-(pyridin-3-ylmethyl)-2-[1-[[4-(1,2,4-triazol-1-yl)phenyl]methyl]pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=CC(=CC=3)N3N=CN=C3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 VZBHCJJQVKGFSC-UHFFFAOYSA-N 0.000 claims description 2
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 2
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 2
- 229940123208 Biguanide Drugs 0.000 claims description 2
- 206010006895 Cachexia Diseases 0.000 claims description 2
- 229920001268 Cholestyramine Polymers 0.000 claims description 2
- 201000004624 Dermatitis Diseases 0.000 claims description 2
- 201000001431 Hyperuricemia Diseases 0.000 claims description 2
- 102000004877 Insulin Human genes 0.000 claims description 2
- 108090001061 Insulin Proteins 0.000 claims description 2
- 229940122199 Insulin secretagogue Drugs 0.000 claims description 2
- 206010033307 Overweight Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 102000018692 Sulfonylurea Receptors Human genes 0.000 claims description 2
- 108010091821 Sulfonylurea Receptors Proteins 0.000 claims description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 2
- 206010000496 acne Diseases 0.000 claims description 2
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims description 2
- 208000022531 anorexia Diseases 0.000 claims description 2
- 208000010668 atopic eczema Diseases 0.000 claims description 2
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- 230000003247 decreasing effect Effects 0.000 claims description 2
- 229940125753 fibrate Drugs 0.000 claims description 2
- 229940125396 insulin Drugs 0.000 claims description 2
- 230000002473 insulinotropic effect Effects 0.000 claims description 2
- VBAAUGQBYHBVNT-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-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(F)=CC=2)C=C1 VBAAUGQBYHBVNT-UHFFFAOYSA-N 0.000 claims description 2
- GYTQYZNZOVHTSR-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-[6-[(4-fluorophenyl)methyl-methylamino]pyrazin-2-yl]-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(F)C=C1 GYTQYZNZOVHTSR-UHFFFAOYSA-N 0.000 claims description 2
- FWFCXCFSXJCUKS-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-[6-[(4-methoxyphenyl)methyl-methylamino]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1CN(C)C1=CN=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC(F)=CC=2)=N1 FWFCXCFSXJCUKS-UHFFFAOYSA-N 0.000 claims description 2
- PDHGYOLSCBGQBD-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-methyl-2-[1-(2-phenoxyethyl)pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCOC=3C=CC=CC=3)C=C2)SC=1C(=O)NCC1=CC=C(F)C=C1 PDHGYOLSCBGQBD-UHFFFAOYSA-N 0.000 claims description 2
- KOPOJJSSNIWROC-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-methyl-2-[6-[methyl(2-pyridin-2-ylethyl)amino]pyrazin-2-yl]-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)CCC1=CC=CC=N1 KOPOJJSSNIWROC-UHFFFAOYSA-N 0.000 claims description 2
- JJAPIHHTKWABOL-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-methyl-2-[6-[methyl(pyridin-4-ylmethyl)amino]pyrazin-2-yl]-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=NC=C1 JJAPIHHTKWABOL-UHFFFAOYSA-N 0.000 claims description 2
- SNSYNTMEUZSUJK-UHFFFAOYSA-N n-benzyl-2-(6-benzylpyrazin-2-yl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(CC=3C=CC=CC=3)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 SNSYNTMEUZSUJK-UHFFFAOYSA-N 0.000 claims description 2
- OHNWRCKCGSXMOS-UHFFFAOYSA-N n-benzyl-2-(6-chloropyrazin-2-yl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(Cl)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 OHNWRCKCGSXMOS-UHFFFAOYSA-N 0.000 claims description 2
- VAIMBEBJDMUXRS-UHFFFAOYSA-N n-benzyl-2-[1-[2-(3-fluorophenyl)ethyl]pyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCC=3C=C(F)C=CC=3)C=C2)SC=1C(=O)NCC1=CC=CC=C1 VAIMBEBJDMUXRS-UHFFFAOYSA-N 0.000 claims description 2
- AXBXPJURPLQSPM-UHFFFAOYSA-N n-benzyl-2-[1-[2-(4-fluorophenoxy)ethyl]pyrazol-3-yl]-4-methyl-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=CC=C1 AXBXPJURPLQSPM-UHFFFAOYSA-N 0.000 claims description 2
- HDSGUOKYJJDUFO-UHFFFAOYSA-N n-benzyl-2-[5-[2-(4-fluorophenyl)ethyl]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=CC(CCC=3C=CC(F)=CC=3)=NC=2)SC=1C(=O)NCC1=CC=CC=C1 HDSGUOKYJJDUFO-UHFFFAOYSA-N 0.000 claims description 2
- DUPJSRQEIOJXIB-FMIVXFBMSA-N n-benzyl-2-[6-[(e)-2-(4-fluorophenyl)ethenyl]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(\C=C\C=3C=CC(F)=CC=3)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 DUPJSRQEIOJXIB-FMIVXFBMSA-N 0.000 claims description 2
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Classifications
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- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D417/14—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 three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
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- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Nutrition Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US82342506P | 2006-08-24 | 2006-08-24 | |
| US60/823,425 | 2006-08-24 | ||
| PCT/US2007/018554 WO2008024390A2 (en) | 2006-08-24 | 2007-08-22 | 2- (pyrazin-2-yl) -thiazole and 2- (1h-pyraz0l-3-yl) -thiazole derivatives as well as related compounds as stearoyl-coa desaturase (scd) inhibitors for the treatment of metabolic, cardiovascular and other disorders |
Publications (1)
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| CA2661017A1 true CA2661017A1 (en) | 2008-02-28 |
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| JP (1) | JP2010501567A (enExample) |
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| MX (1) | MX2009002019A (enExample) |
| RU (1) | RU2009110254A (enExample) |
| WO (1) | WO2008024390A2 (enExample) |
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| RU2009109147A (ru) | 2006-08-15 | 2010-09-27 | Новартис АГ (CH) | Органические соединения |
| 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 |
| MX2010009158A (es) | 2008-02-20 | 2010-09-24 | Novartis Ag | Inhibidores heterociclicos de estearoil-coa-desaturasa. |
| 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 |
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| CN103402515B (zh) | 2010-11-09 | 2017-05-17 | 铁木医药有限公司 | sGC刺激剂 |
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| 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 |
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| 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 |
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| CN112312913B (zh) | 2018-03-23 | 2024-03-08 | 詹森药业有限公司 | 化合物和其用途 |
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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
Also Published As
| Publication number | Publication date |
|---|---|
| AU2007288245A1 (en) | 2008-02-28 |
| JP2010501567A (ja) | 2010-01-21 |
| KR20090040478A (ko) | 2009-04-24 |
| US20100239520A1 (en) | 2010-09-23 |
| MX2009002019A (es) | 2009-03-09 |
| US8314138B2 (en) | 2012-11-20 |
| EP2086970A2 (en) | 2009-08-12 |
| EP2086970B1 (en) | 2014-02-26 |
| BRPI0719122A2 (pt) | 2013-12-10 |
| WO2008024390A3 (en) | 2008-04-17 |
| RU2009110254A (ru) | 2010-09-27 |
| CN101506203B (zh) | 2013-10-16 |
| WO2008024390A2 (en) | 2008-02-28 |
| CN101506203A (zh) | 2009-08-12 |
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