ES2516691T3 - Antagonistas del receptor de glucagón, preparación y usos terapéuticos - Google Patents

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Publication number

ES2516691T3

ES2516691T3 ES06850764.9T ES06850764T ES2516691T3 ES 2516691 T3 ES2516691 T3 ES 2516691T3 ES 06850764 T ES06850764 T ES 06850764T ES 2516691 T3 ES2516691 T3 ES 2516691T3

Authority

ES

Spain

Prior art keywords

alkyl

halogens

optionally substituted

cycloalkyl

independently

Prior art date

2005-11-22

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.)

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• 238000002360 preparation method Methods 0.000 title description 36
• 229940122904 Glucagon receptor antagonist Drugs 0.000 title description 8
• 230000001225 therapeutic effect Effects 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 178
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 106
• 150000002367 halogens Chemical class 0.000 claims abstract description 72
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 28
• 150000003839 salts Chemical class 0.000 claims abstract description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
• 239000001257 hydrogen Substances 0.000 claims abstract description 11
• 239000002243 precursor Substances 0.000 claims abstract description 9
• -1 3,3-dimethylbutyl Chemical group 0.000 claims description 55
• 238000011282 treatment Methods 0.000 claims description 37
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
• 206010012601 diabetes mellitus Diseases 0.000 claims description 25
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims description 18
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
• 239000011737 fluorine Substances 0.000 claims description 13
• 229910052731 fluorine Inorganic materials 0.000 claims description 13
• 229910052794 bromium Inorganic materials 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 11
• 208000008589 Obesity Diseases 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 10
• 201000001421 hyperglycemia Diseases 0.000 claims description 10
• 235000020824 obesity Nutrition 0.000 claims description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
• 239000000460 chlorine Substances 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 8
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
• 201000001320 Atherosclerosis Diseases 0.000 claims description 6
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 150000002431 hydrogen Chemical class 0.000 claims description 6
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• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
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• 208000032382 Ischaemic stroke Diseases 0.000 claims description 5
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 5
• 208000031225 myocardial ischemia Diseases 0.000 claims description 5
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• 125000000439 4-methylpentoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 2
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
• 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
• 125000003342 alkenyl group Chemical group 0.000 claims description 2
• 125000003545 alkoxy group Chemical group 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
• BIZGMTWBKDPTLH-UHFFFAOYSA-N propan-2-yl hypochlorite Chemical compound CC(C)OCl BIZGMTWBKDPTLH-UHFFFAOYSA-N 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
• 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims 2
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• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 49
• 238000000034 method Methods 0.000 description 49
• 108010063919 Glucagon Receptors Proteins 0.000 description 45
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• 238000006243 chemical reaction Methods 0.000 description 41
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