MXPA06003997A - Derivados de 3-(4-aminofenil) tienopirimid-4-ona como antagonistas mch r1 para el tratamiento de obesidad, diabetes, depresion y ansiedad. - Google Patents

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Publication number

MXPA06003997A

MXPA06003997A MXPA06003997A MXPA06003997A MXPA06003997A MX PA06003997 A MXPA06003997 A MX PA06003997A MX PA06003997 A MXPA06003997 A MX PA06003997A MX PA06003997 A MXPA06003997 A MX PA06003997A MX PA06003997 A MXPA06003997 A MX PA06003997A

Authority

MX

Mexico

Prior art keywords

formula

compound

group

ring

alkyl

Prior art date

2003-10-23

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• 208000008589 Obesity Diseases 0.000 title claims abstract description 25
• 235000020824 obesity Nutrition 0.000 title claims abstract description 25
• 238000011282 treatment Methods 0.000 title claims abstract description 22
• 206010012601 diabetes mellitus Diseases 0.000 title claims abstract description 15
• 239000005557 antagonist Substances 0.000 title claims abstract description 14
• 208000019901 Anxiety disease Diseases 0.000 title claims abstract description 13
• 230000036506 anxiety Effects 0.000 title claims abstract description 13
• LVAGVGLOKJYPSZ-UHFFFAOYSA-N 3-(4-aminophenyl)thieno[3,2-d]pyrimidin-4-one Chemical class C1=CC(N)=CC=C1N1C(=O)C(SC=C2)=C2N=C1 LVAGVGLOKJYPSZ-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 144
• 238000000034 method Methods 0.000 claims abstract description 53
• 230000008569 process Effects 0.000 claims abstract description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
• 239000003814 drug Substances 0.000 claims abstract description 14
• 238000002360 preparation method Methods 0.000 claims abstract description 14
• -1 d_3alkyl Chemical group 0.000 claims description 59
• 150000003839 salts Chemical class 0.000 claims description 38
• 239000012453 solvate Substances 0.000 claims description 32
• 125000000217 alkyl group Chemical group 0.000 claims description 31
• 125000005843 halogen group Chemical group 0.000 claims description 31
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 29
• 125000003118 aryl group Chemical group 0.000 claims description 18
• 239000003795 chemical substances by application Substances 0.000 claims description 17
• 239000001257 hydrogen Substances 0.000 claims description 17
• 229910052739 hydrogen Inorganic materials 0.000 claims description 17
• 239000002904 solvent Substances 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 238000006243 chemical reaction Methods 0.000 claims description 15
• 125000000623 heterocyclic group Chemical group 0.000 claims description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
• 241000124008 Mammalia Species 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 125000001424 substituent group Chemical group 0.000 claims description 14
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 10
• 125000004953 trihalomethyl group Chemical group 0.000 claims description 9
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
• 229910052757 nitrogen Inorganic materials 0.000 claims description 6
• 125000004043 oxo group Chemical group O=* 0.000 claims description 6
• 125000004951 trihalomethoxy group Chemical group 0.000 claims description 6
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• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
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• 125000005842 heteroatom Chemical group 0.000 claims description 5
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• 229910052760 oxygen Inorganic materials 0.000 claims description 5
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• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
• 125000003282 alkyl amino group Chemical group 0.000 claims description 4
• 150000002148 esters Chemical class 0.000 claims description 4
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• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
• 239000000556 agonist Substances 0.000 claims description 3
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• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 2
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
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• 239000007868 Raney catalyst Substances 0.000 claims description 2
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
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• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
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• 150000001413 amino acids Chemical class 0.000 claims description 2
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 2
• 230000008878 coupling Effects 0.000 claims description 2
• 239000007822 coupling agent Substances 0.000 claims description 2
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• 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 2
• 239000003112 inhibitor Substances 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 230000001561 neurotransmitter reuptake Effects 0.000 claims description 2
• JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical group OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims description 2
• 239000002485 serotonin 2C agonist Substances 0.000 claims description 2
• WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 claims description 2
• 239000011593 sulfur Substances 0.000 claims description 2
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
• SYEXCHNVDLNLJK-UHFFFAOYSA-N 6-(4-chlorophenyl)-3-(3-methoxy-4-pyrrolidin-1-ylphenyl)thieno[3,2-d]pyrimidin-4-one Chemical compound COC1=CC(N2C(C=3SC(=CC=3N=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1N1CCCC1 SYEXCHNVDLNLJK-UHFFFAOYSA-N 0.000 claims 1
• 108010016122 Ghrelin Receptors Proteins 0.000 claims 1
• 102100039256 Growth hormone secretagogue receptor type 1 Human genes 0.000 claims 1
• 229940125425 inverse agonist Drugs 0.000 claims 1
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• 239000002464 receptor antagonist Substances 0.000 claims 1
• JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims 1
• 101800002739 Melanin-concentrating hormone Proteins 0.000 abstract description 18
• 102400001132 Melanin-concentrating hormone Human genes 0.000 abstract description 17
• 229940079593 drug Drugs 0.000 abstract description 7
• 150000004982 aromatic amines Chemical class 0.000 abstract description 3
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• 235000002639 sodium chloride Nutrition 0.000 description 37
• 239000000203 mixture Substances 0.000 description 30
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