JP2011520915A5 - - Google Patents

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Publication number

JP2011520915A5

JP2011520915A5 JP2011509762A JP2011509762A JP2011520915A5 JP 2011520915 A5 JP2011520915 A5 JP 2011520915A5 JP 2011509762 A JP2011509762 A JP 2011509762A JP 2011509762 A JP2011509762 A JP 2011509762A JP 2011520915 A5 JP2011520915 A5 JP 2011520915A5

Authority

JP

Japan

Prior art keywords

alkyl

pyran

tetrahydro

cyclopropylsulfonyl

propanamide

Prior art date

2009-05-15

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.)

Granted

Links

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• -1 aryl (C 1-10 ) alkyl Chemical group 0.000 claims description 283
• 150000001875 compounds Chemical class 0.000 claims description 35
• HAMZIZRSAJARRH-UHFFFAOYSA-N 4-cyclopropylsulfonyl-1-[1-[(5-fluoro-1,3-thiazol-2-yl)amino]-3-(oxan-4-yl)-1-oxopropan-2-yl]indazole-6-carboxylic acid Chemical compound C12=CC(C(=O)O)=CC(S(=O)(=O)C3CC3)=C2C=NN1C(C(=O)NC=1SC(F)=CN=1)CC1CCOCC1 HAMZIZRSAJARRH-UHFFFAOYSA-N 0.000 claims description 2
• 125000000217 alkyl group Chemical group 0.000 claims 132
• 125000005842 heteroatom Chemical group 0.000 claims 102
• 125000000753 cycloalkyl group Chemical group 0.000 claims 60
• 125000003118 aryl group Chemical group 0.000 claims 38
• 150000001602 bicycloalkyls Chemical group 0.000 claims 29
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 25
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 25
• 229910052739 hydrogen Inorganic materials 0.000 claims 23
• 239000001257 hydrogen Substances 0.000 claims 23
• 125000004104 aryloxy group Chemical group 0.000 claims 22
• 150000002431 hydrogen Chemical class 0.000 claims 21
• 125000001072 heteroaryl group Chemical group 0.000 claims 20
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 17
• 125000003282 alkyl amino group Chemical group 0.000 claims 16
• 125000005843 halogen group Chemical group 0.000 claims 16
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 16
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 13
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 12
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 12
• 239000003814 drug Substances 0.000 claims 11
• 125000001841 imino group Chemical group [H]N=* 0.000 claims 11
• 238000004519 manufacturing process Methods 0.000 claims 10
• 125000003545 alkoxy group Chemical group 0.000 claims 9
• 125000005553 heteroaryloxy group Chemical group 0.000 claims 9
• 229940124530 sulfonamide Drugs 0.000 claims 9
• 150000003456 sulfonamides Chemical class 0.000 claims 9
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 8
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 8
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 7
• 150000001408 amides Chemical class 0.000 claims 7
• 125000005188 oxoalkyl group Chemical group 0.000 claims 7
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 7
• 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims 5
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
• 150000003839 salts Chemical class 0.000 claims 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
• 125000004429 atom Chemical group 0.000 claims 2
• 150000003857 carboxamides Chemical class 0.000 claims 2
• KUFXUEYIWPFSHN-HNNXBMFYSA-N (2s)-2-(4-cyclopropylsulfonylpyrazolo[3,4-c]pyridin-1-yl)-n-(5-fluoro-1,3-thiazol-2-yl)-3-(oxan-4-yl)propanamide Chemical compound S1C(F)=CN=C1NC(=O)[C@@H](N1C2=CN=CC(=C2C=N1)S(=O)(=O)C1CC1)CC1CCOCC1 KUFXUEYIWPFSHN-HNNXBMFYSA-N 0.000 claims 1
• QAVCBIQSDBRVDD-UHFFFAOYSA-N 4-chloro-1-[1-[(5-chloro-1,3-thiazol-2-yl)amino]-3-(oxan-4-yl)-1-oxopropan-2-yl]-n-cyclopropylpyrazole-3-carboxamide Chemical compound S1C(Cl)=CN=C1NC(=O)C(N1N=C(C(Cl)=C1)C(=O)NC1CC1)CC1CCOCC1 QAVCBIQSDBRVDD-UHFFFAOYSA-N 0.000 claims 1
• 208000024172 Cardiovascular disease Diseases 0.000 claims 1
• 208000032928 Dyslipidaemia Diseases 0.000 claims 1
• 102000030595 Glucokinase Human genes 0.000 claims 1
• 108010021582 Glucokinase Proteins 0.000 claims 1
• 208000002705 Glucose Intolerance Diseases 0.000 claims 1
• 206010022489 Insulin Resistance Diseases 0.000 claims 1
• 208000017170 Lipid metabolism disease Diseases 0.000 claims 1
• 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
• 208000008589 Obesity Diseases 0.000 claims 1
• 201000010390 abdominal obesity-metabolic syndrome 1 Diseases 0.000 claims 1
• 230000003213 activating effect Effects 0.000 claims 1
• 239000004480 active ingredient Substances 0.000 claims 1
• 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
• 206010012601 diabetes mellitus Diseases 0.000 claims 1
• 201000001421 hyperglycemia Diseases 0.000 claims 1
• 125000004536 indazol-1-yl group Chemical group N1(N=CC2=CC=CC=C12)* 0.000 claims 1
• 208000011661 metabolic syndrome X Diseases 0.000 claims 1
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
• NPMMXKUVLURCMA-UHFFFAOYSA-N n-(oxan-4-yl)propanamide Chemical compound CCC(=O)NC1CCOCC1 NPMMXKUVLURCMA-UHFFFAOYSA-N 0.000 claims 1
• 235000020824 obesity Nutrition 0.000 claims 1
• 239000008194 pharmaceutical composition Substances 0.000 claims 1
• 239000000546 pharmaceutical excipient Substances 0.000 claims 1
• 201000010065 polycystic ovary syndrome Diseases 0.000 claims 1
• 201000009104 prediabetes syndrome Diseases 0.000 claims 1
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
• SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 1
• KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
• 229940126208 compound 22 Drugs 0.000 description 1
• 229940125833 compound 23 Drugs 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• 238000002953 preparative HPLC Methods 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• 239000003643 water by type Substances 0.000 description 1