ES2391107T3 - Compuestos que tienen actividad en el receptor M1 y sus usos en medicina - Google Patents

Info

Publication number

ES2391107T3

ES2391107T3 ES06794587T ES06794587T ES2391107T3 ES 2391107 T3 ES2391107 T3 ES 2391107T3 ES 06794587 T ES06794587 T ES 06794587T ES 06794587 T ES06794587 T ES 06794587T ES 2391107 T3 ES2391107 T3 ES 2391107T3

Authority

ES

Spain

Prior art keywords

dihydro

benzimidazol

piperidinyl

group

compound

Prior art date

2005-09-30

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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• 239000003814 drug Substances 0.000 title claims description 46
• 230000000694 effects Effects 0.000 title description 34
• 102000017927 CHRM1 Human genes 0.000 title description 8
• 101150073075 Chrm1 gene Proteins 0.000 title description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 60
• 150000003839 salts Chemical class 0.000 claims abstract description 58
• 239000012453 solvate Substances 0.000 claims abstract description 46
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 44
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 43
• 239000001257 hydrogen Substances 0.000 claims abstract description 33
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 27
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 21
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 20
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
• -1 methoxy, methylethyloxy Chemical group 0.000 claims description 127
• 238000000034 method Methods 0.000 claims description 53
• 238000011282 treatment Methods 0.000 claims description 53
• 208000028017 Psychotic disease Diseases 0.000 claims description 52
• 238000006243 chemical reaction Methods 0.000 claims description 30
• 239000000460 chlorine Chemical group 0.000 claims description 29
• 229910052801 chlorine Inorganic materials 0.000 claims description 29
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 28
• 125000000217 alkyl group Chemical group 0.000 claims description 28
• 230000008569 process Effects 0.000 claims description 27
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 26
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 26
• 229910052794 bromium Inorganic materials 0.000 claims description 26
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
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• 229910052731 fluorine Inorganic materials 0.000 claims description 12
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• 239000007818 Grignard reagent Substances 0.000 claims description 3
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• SUDVDXLERRETAJ-UHFFFAOYSA-N 5-chloro-6-fluoro-3-[1-(oxan-4-yl)piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C1=2C=C(Cl)C(F)=CC=2NC(=O)N1C(CC1)CCN1C1CCOCC1 SUDVDXLERRETAJ-UHFFFAOYSA-N 0.000 claims description 2
• DNAMLMXAUGCMQJ-UHFFFAOYSA-N 5-ethyl-6-fluoro-3-[1-(oxan-4-yl)piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound O=C1NC=2C=C(F)C(CC)=CC=2N1C(CC1)CCN1C1CCOCC1 DNAMLMXAUGCMQJ-UHFFFAOYSA-N 0.000 claims description 2
• ZJUVGPGEGBOBEP-UHFFFAOYSA-N 5-methyl-3-[1-(oxan-4-yl)piperidin-4-yl]-6-propan-2-yloxy-1h-benzimidazol-2-one Chemical compound C1=2C=C(C)C(OC(C)C)=CC=2NC(=O)N1C(CC1)CCN1C1CCOCC1 ZJUVGPGEGBOBEP-UHFFFAOYSA-N 0.000 claims description 2
• TVQAYNDIQSTXAD-UHFFFAOYSA-N 6-fluoro-5-methyl-3-[1-(4-methyloxan-4-yl)piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound O=C1NC=2C=C(F)C(C)=CC=2N1C(CC1)CCN1C1(C)CCOCC1 TVQAYNDIQSTXAD-UHFFFAOYSA-N 0.000 claims description 2
• NGWDIPICBHGGLN-UHFFFAOYSA-N 6-methoxy-5-methyl-3-[1-(oxan-4-yl)piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C1=2C=C(C)C(OC)=CC=2NC(=O)N1C(CC1)CCN1C1CCOCC1 NGWDIPICBHGGLN-UHFFFAOYSA-N 0.000 claims description 2
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
• SQAKCMJNCAVKOS-UHFFFAOYSA-N 6-chloro-5-methoxy-3-[1-(oxan-4-yl)piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound O=C1NC=2C=C(Cl)C(OC)=CC=2N1C(CC1)CCN1C1CCOCC1 SQAKCMJNCAVKOS-UHFFFAOYSA-N 0.000 claims 1
• 238000003747 Grignard reaction Methods 0.000 claims 1
• 125000005843 halogen group Chemical group 0.000 abstract description 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 239
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