TW200540142A - New β-ketoamide compounds with MCH receptor antagonistic activity and medicaments comprising them - Google Patents

Info

Publication number

TW200540142A

TW200540142A TW094106522A TW94106522A TW200540142A TW 200540142 A TW200540142 A TW 200540142A TW 094106522 A TW094106522 A TW 094106522A TW 94106522 A TW94106522 A TW 94106522A TW 200540142 A TW200540142 A TW 200540142A

Authority

TW

Taiwan

Prior art keywords

alkyl

group

substituted

atoms

amino

Prior art date

2004-03-06

Links

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• Global Dossier
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• -1 β-ketoamide compounds Chemical class 0.000 title claims abstract description 250
• 230000003042 antagnostic effect Effects 0.000 title claims abstract description 9
• 239000003814 drug Substances 0.000 title claims abstract description 8
• 108010047068 Melanin-concentrating hormone receptor Proteins 0.000 title abstract description 15
• 102000006953 melanin-concentrating hormone receptor activity proteins Human genes 0.000 title abstract 2
• 208000008589 Obesity Diseases 0.000 claims abstract description 43
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 22
• 206010006550 Bulimia nervosa Diseases 0.000 claims abstract description 10
• 206010061428 decreased appetite Diseases 0.000 claims abstract description 10
• 208000032841 Bulimia Diseases 0.000 claims abstract description 8
• 208000022531 anorexia Diseases 0.000 claims abstract description 6
• 208000030159 metabolic disease Diseases 0.000 claims abstract description 5
• 150000001408 amides Chemical class 0.000 claims abstract 2
• 125000000217 alkyl group Chemical group 0.000 claims description 225
• 150000001875 compounds Chemical class 0.000 claims description 110
• 125000004432 carbon atom Chemical group C* 0.000 claims description 92
• 239000013543 active substance Substances 0.000 claims description 90
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 74
• 239000000203 mixture Substances 0.000 claims description 65
• 150000003839 salts Chemical class 0.000 claims description 56
• 125000004429 atom Chemical group 0.000 claims description 53
• 125000000623 heterocyclic group Chemical group 0.000 claims description 47
• 235000020824 obesity Nutrition 0.000 claims description 42
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 39
• 239000002904 solvent Substances 0.000 claims description 39
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
• 238000002360 preparation method Methods 0.000 claims description 34
• 238000011282 treatment Methods 0.000 claims description 33
• 239000000126 substance Substances 0.000 claims description 32
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
• 229910052731 fluorine Inorganic materials 0.000 claims description 29
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
• 125000003545 alkoxy group Chemical group 0.000 claims description 26
• 150000001412 amines Chemical class 0.000 claims description 26
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 26
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
• 239000005557 antagonist Substances 0.000 claims description 25
• 125000004122 cyclic group Chemical group 0.000 claims description 25
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
• 238000000034 method Methods 0.000 claims description 25
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 24
• 239000002253 acid Substances 0.000 claims description 24
• 229960003299 ketamine Drugs 0.000 claims description 21
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims description 21
• 229910052794 bromium Inorganic materials 0.000 claims description 20
• 201000010099 disease Diseases 0.000 claims description 19
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
• 125000003342 alkenyl group Chemical group 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
• 125000005842 heteroatom Chemical group 0.000 claims description 18
• 125000002837 carbocyclic group Chemical group 0.000 claims description 17
• 208000035475 disorder Diseases 0.000 claims description 17
• 238000006467 substitution reaction Methods 0.000 claims description 17
• 125000003277 amino group Chemical group 0.000 claims description 16
• 125000003118 aryl group Chemical group 0.000 claims description 16
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 16
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
• 230000002265 prevention Effects 0.000 claims description 15
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 14
• 230000000694 effects Effects 0.000 claims description 14
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
• 125000004076 pyridyl group Chemical group 0.000 claims description 14
• 125000000304 alkynyl group Chemical group 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 125000003282 alkyl amino group Chemical group 0.000 claims description 11
• 206010003246 arthritis Diseases 0.000 claims description 11
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
• 241001465754 Metazoa Species 0.000 claims description 10
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
• 229910052757 nitrogen Inorganic materials 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• 229920006395 saturated elastomer Polymers 0.000 claims description 10
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
• 241000124008 Mammalia Species 0.000 claims description 9
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
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• 150000003254 radicals Chemical class 0.000 claims description 9
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• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
• 125000000879 imine group Chemical group 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 206010020772 Hypertension Diseases 0.000 claims description 7
• 229910052740 iodine Inorganic materials 0.000 claims description 7
• 239000011877 solvent mixture Substances 0.000 claims description 7
• 208000019901 Anxiety disease Diseases 0.000 claims description 6
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 6
• 235000005911 diet Nutrition 0.000 claims description 6
• 125000001624 naphthyl group Chemical group 0.000 claims description 6
• 230000004584 weight gain Effects 0.000 claims description 6
• 235000019786 weight gain Nutrition 0.000 claims description 6
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 5
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• 208000019022 Mood disease Diseases 0.000 claims description 5
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• 239000000969 carrier Substances 0.000 claims description 5
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
• 230000020595 eating behavior Effects 0.000 claims description 5
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 238000001727 in vivo Methods 0.000 claims description 5
• 125000001041 indolyl group Chemical group 0.000 claims description 5
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
• 125000004434 sulfur atom Chemical group 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 4
• 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 4
• 206010046543 Urinary incontinence Diseases 0.000 claims description 4
• 150000001335 aliphatic alkanes Chemical group 0.000 claims description 4
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
• 125000002947 alkylene group Chemical group 0.000 claims description 4
• 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 4
• 229960001058 bupropion Drugs 0.000 claims description 4
• 208000033679 diabetic kidney disease Diseases 0.000 claims description 4
• 230000037213 diet Effects 0.000 claims description 4
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
• 150000002367 halogens Chemical class 0.000 claims description 4
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• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
• 206010006895 Cachexia Diseases 0.000 claims description 3
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• 208000008967 Enuresis Diseases 0.000 claims description 3
• 206010022489 Insulin Resistance Diseases 0.000 claims description 3
• 229930194542 Keto Natural products 0.000 claims description 3
• 208000026139 Memory disease Diseases 0.000 claims description 3
• 201000001880 Sexual dysfunction Diseases 0.000 claims description 3
• 238000009825 accumulation Methods 0.000 claims description 3
• 125000002619 bicyclic group Chemical group 0.000 claims description 3
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
• 206010015037 epilepsy Diseases 0.000 claims description 3
• 230000003054 hormonal effect Effects 0.000 claims description 3
• 208000008585 mastocytosis Diseases 0.000 claims description 3
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 3
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
• 230000001850 reproductive effect Effects 0.000 claims description 3
• 231100000872 sexual dysfunction Toxicity 0.000 claims description 3
• 125000003003 spiro group Chemical group 0.000 claims description 3
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 3
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
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• 241000283973 Oryctolagus cuniculus Species 0.000 claims description 2
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• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
• 125000004414 alkyl thio group Chemical group 0.000 claims description 2
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
• 230000004064 dysfunction Effects 0.000 claims description 2
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims description 2
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• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 2
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• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
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• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
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