EA018709B1 - Пиридоновые агонисты сопряженного с g-белком рецептора gpr119 - Google Patents

Info

Publication number

EA018709B1

EA018709B1 EA201000210A EA201000210A EA018709B1 EA 018709 B1 EA018709 B1 EA 018709B1 EA 201000210 A EA201000210 A EA 201000210A EA 201000210 A EA201000210 A EA 201000210A EA 018709 B1 EA018709 B1 EA 018709B1

Authority

EA

Eurasian Patent Office

Prior art keywords

phenyl

4yloxy

methylsulfonyl

piperidin

pyridin

Prior art date

2007-07-17

Links

• Espacenet
• Global Dossier
• Discuss

• LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 title description 2
• 229940080349 GPR agonist Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 440
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 37
• 201000010099 disease Diseases 0.000 claims abstract description 23
• -1 (methylsulfonyl) phenyl Chemical group 0.000 claims description 486
• 238000000034 method Methods 0.000 claims description 271
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 164
• 229920006395 saturated elastomer Polymers 0.000 claims description 91
• 125000003118 aryl group Chemical group 0.000 claims description 88
• 229910052736 halogen Inorganic materials 0.000 claims description 79
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 74
• 150000002367 halogens Chemical class 0.000 claims description 70
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 69
• 125000001624 naphthyl group Chemical group 0.000 claims description 67
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 64
• 125000004076 pyridyl group Chemical group 0.000 claims description 63
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 60
• 229910052739 hydrogen Inorganic materials 0.000 claims description 57
• 239000001257 hydrogen Substances 0.000 claims description 56
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 56
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 54
• 150000003839 salts Chemical class 0.000 claims description 44
• 125000000217 alkyl group Chemical group 0.000 claims description 39
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 36
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 34
• 206010012601 diabetes mellitus Diseases 0.000 claims description 33
• 125000004122 cyclic group Chemical group 0.000 claims description 27
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 22
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 20
• 125000005842 heteroatom Chemical group 0.000 claims description 20
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 19
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 18
• 125000001072 heteroaryl group Chemical group 0.000 claims description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
• 208000008589 Obesity Diseases 0.000 claims description 15
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 15
• 235000020824 obesity Nutrition 0.000 claims description 15
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 14
• DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims description 14
• 208000035475 disorder Diseases 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
• 230000000694 effects Effects 0.000 claims description 12
• JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 claims description 12
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 11
• 208000001145 Metabolic Syndrome Diseases 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 206010022489 Insulin Resistance Diseases 0.000 claims description 8
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 8
• 125000001188 haloalkyl group Chemical group 0.000 claims description 8
• 125000001544 thienyl group Chemical group 0.000 claims description 8
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 7
• 241000124008 Mammalia Species 0.000 claims description 7
• 150000007942 carboxylates Chemical class 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 201000001421 hyperglycemia Diseases 0.000 claims description 7
• 208000017169 kidney disease Diseases 0.000 claims description 7
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• 206010020772 Hypertension Diseases 0.000 claims description 6
• 208000031225 myocardial ischemia Diseases 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 230000002792 vascular Effects 0.000 claims description 6
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 5
• VWKJOAPEYFYCKS-UHFFFAOYSA-N 4-[1-(5-propylpyrimidin-2-yl)piperidin-4-yl]oxy-1h-pyridin-2-one Chemical compound N1=CC(CCC)=CN=C1N1CCC(OC2=CC(=O)NC=C2)CC1 VWKJOAPEYFYCKS-UHFFFAOYSA-N 0.000 claims description 5
• 201000001320 Atherosclerosis Diseases 0.000 claims description 5
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• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 5
• 208000006011 Stroke Diseases 0.000 claims description 5
• KVVMXWRFYAGASO-UHFFFAOYSA-N azetidine-1-carboxylic acid Chemical compound OC(=O)N1CCC1 KVVMXWRFYAGASO-UHFFFAOYSA-N 0.000 claims description 5
• 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 5
• 201000008980 hyperinsulinism Diseases 0.000 claims description 5
• 229910052700 potassium Inorganic materials 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 208000020084 Bone disease Diseases 0.000 claims description 4
• 208000002705 Glucose Intolerance Diseases 0.000 claims description 4
• 208000035150 Hypercholesterolemia Diseases 0.000 claims description 4
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 4
• 102000007330 LDL Lipoproteins Human genes 0.000 claims description 4
• 206010028980 Neoplasm Diseases 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 201000011510 cancer Diseases 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• 208000006575 hypertriglyceridemia Diseases 0.000 claims description 4
• 208000015181 infectious disease Diseases 0.000 claims description 4
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• 230000007823 neuropathy Effects 0.000 claims description 4
• 208000033808 peripheral neuropathy Diseases 0.000 claims description 4
• 201000009104 prediabetes syndrome Diseases 0.000 claims description 4
• 208000037803 restenosis Diseases 0.000 claims description 4
• 239000012453 solvate Substances 0.000 claims description 4
• 230000029663 wound healing Effects 0.000 claims description 4
• 208000028698 Cognitive impairment Diseases 0.000 claims description 3
• 206010012289 Dementia Diseases 0.000 claims description 3
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 3
• 206010049287 Lipodystrophy acquired Diseases 0.000 claims description 3
• 206010033645 Pancreatitis Diseases 0.000 claims description 3
• MEOZFUYXLCDYGA-UHFFFAOYSA-N azepane-1-carboxylic acid Chemical compound OC(=O)N1CCCCCC1 MEOZFUYXLCDYGA-UHFFFAOYSA-N 0.000 claims description 3
• 125000005605 benzo group Chemical group 0.000 claims description 3
• 208000010877 cognitive disease Diseases 0.000 claims description 3
• 230000003111 delayed effect Effects 0.000 claims description 3
• 230000004217 heart function Effects 0.000 claims description 3
• 230000001771 impaired effect Effects 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 208000006132 lipodystrophy Diseases 0.000 claims description 3
• 230000004770 neurodegeneration Effects 0.000 claims description 3
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
• 230000002265 prevention Effects 0.000 claims description 3
• 102000004169 proteins and genes Human genes 0.000 claims description 3
• 108090000623 proteins and genes Proteins 0.000 claims description 3
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
• NRGKFNDKBDBBGY-UHFFFAOYSA-N 1h-pyridin-2-one;hydrochloride Chemical compound Cl.O=C1C=CC=CN1 NRGKFNDKBDBBGY-UHFFFAOYSA-N 0.000 claims description 2
• ZFJNSEQJNCTGMD-UHFFFAOYSA-N 2,3-difluoro-4-[2-oxo-4-[1-(5-propylpyrimidin-2-yl)piperidin-4-yl]oxypyridin-1-yl]benzonitrile Chemical compound N1=CC(CCC)=CN=C1N1CCC(OC2=CC(=O)N(C=3C(=C(F)C(C#N)=CC=3)F)C=C2)CC1 ZFJNSEQJNCTGMD-UHFFFAOYSA-N 0.000 claims description 2
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
• XIMHQHRHZSIVBJ-UHFFFAOYSA-N 3-fluoro-4-[2-oxo-4-[1-[5-(3,3,3-trifluoropropyl)pyrimidin-2-yl]piperidin-4-yl]oxypyridin-1-yl]benzonitrile Chemical compound FC1=CC(C#N)=CC=C1N1C(=O)C=C(OC2CCN(CC2)C=2N=CC(CCC(F)(F)F)=CN=2)C=C1 XIMHQHRHZSIVBJ-UHFFFAOYSA-N 0.000 claims description 2
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 2
• GTYSJWCJBDEETJ-UHFFFAOYSA-N 4-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]oxy-1-pyridin-3-ylpyridin-2-one Chemical compound N1=CC(CC)=CN=C1N1CCC(OC2=CC(=O)N(C=3C=NC=CC=3)C=C2)CC1 GTYSJWCJBDEETJ-UHFFFAOYSA-N 0.000 claims description 2
• SHZJSZGDKLPDPQ-UHFFFAOYSA-N 4-[1-(5-propylpyrimidin-2-yl)piperidin-4-yl]oxy-1-pyrimidin-5-ylpyridin-2-one Chemical compound N1=CC(CCC)=CN=C1N1CCC(OC2=CC(=O)N(C=3C=NC=NC=3)C=C2)CC1 SHZJSZGDKLPDPQ-UHFFFAOYSA-N 0.000 claims description 2
• 229940124213 Dipeptidyl peptidase 4 (DPP IV) inhibitor Drugs 0.000 claims description 2
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 2
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• YTVNJLOIDUGFHD-UHFFFAOYSA-N propan-2-yl 4-[1-(3-methoxyphenyl)-2-oxopyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound COC1=CC=CC(N2C(C=C(OC3CCN(CC3)C(=O)OC(C)C)C=C2)=O)=C1 YTVNJLOIDUGFHD-UHFFFAOYSA-N 0.000 claims description 2
• CPCJQCHFOAHMQF-UHFFFAOYSA-N propan-2-yl 4-[1-(4-cyano-2-fluorophenyl)-2-oxopyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1OC1=CC(=O)N(C=2C(=CC(=CC=2)C#N)F)C=C1 CPCJQCHFOAHMQF-UHFFFAOYSA-N 0.000 claims description 2
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 18
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 8
• NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 claims 3
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 2
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
• IKQORWCSZJKSFE-UHFFFAOYSA-N 2,2,2-trifluoro-n-(4-hydroxyphenyl)acetamide Chemical compound OC1=CC=C(NC(=O)C(F)(F)F)C=C1 IKQORWCSZJKSFE-UHFFFAOYSA-N 0.000 claims 1
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• CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 1
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