EA025380B1 - Новые циклические производные азабензимидазола, используемые в качестве антидиабетических агентов - Google Patents

Info

Publication number

EA025380B1

EA025380B1 EA201391236A EA201391236A EA025380B1 EA 025380 B1 EA025380 B1 EA 025380B1 EA 201391236 A EA201391236 A EA 201391236A EA 201391236 A EA201391236 A EA 201391236A EA 025380 B1 EA025380 B1 EA 025380B1

Authority

EA

Eurasian Patent Office

Prior art keywords

alkyl

phenyl

heteroaryl

cycloalkyl

unsubstituted

Prior art date

2011-02-25

Links

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• -1 cyclic azabenzimidazole derivatives Chemical class 0.000 title claims description 178
• 239000003472 antidiabetic agent Substances 0.000 title description 3
• 229940125708 antidiabetic agent Drugs 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 267
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 99
• 208000008589 Obesity Diseases 0.000 claims abstract description 70
• 235000020824 obesity Nutrition 0.000 claims abstract description 70
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 55
• 206010020772 Hypertension Diseases 0.000 claims abstract description 47
• 201000010099 disease Diseases 0.000 claims abstract description 41
• 208000001145 Metabolic Syndrome Diseases 0.000 claims abstract description 27
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims abstract description 27
• 201000001421 hyperglycemia Diseases 0.000 claims abstract description 13
• 208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 12
• 102000001253 Protein Kinase Human genes 0.000 claims abstract description 7
• 108060006633 protein kinase Proteins 0.000 claims abstract description 7
• 125000000217 alkyl group Chemical group 0.000 claims description 1006
• 125000001424 substituent group Chemical group 0.000 claims description 325
• 229910052736 halogen Inorganic materials 0.000 claims description 292
• 150000002367 halogens Chemical class 0.000 claims description 272
• 125000001072 heteroaryl group Chemical group 0.000 claims description 242
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 195
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 170
• 239000013256 coordination polymer Substances 0.000 claims description 130
• 229910052739 hydrogen Inorganic materials 0.000 claims description 121
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 107
• 239000001257 hydrogen Substances 0.000 claims description 107
• 125000003118 aryl group Chemical group 0.000 claims description 103
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 102
• 150000003839 salts Chemical class 0.000 claims description 82
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 78
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 65
• 238000000034 method Methods 0.000 claims description 53
• 125000004432 carbon atom Chemical group C* 0.000 claims description 51
• 125000000304 alkynyl group Chemical group 0.000 claims description 46
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 46
• 108010011376 AMP-Activated Protein Kinases Proteins 0.000 claims description 45
• 102000014156 AMP-Activated Protein Kinases Human genes 0.000 claims description 45
• 239000003814 drug Substances 0.000 claims description 45
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
• 125000002619 bicyclic group Chemical group 0.000 claims description 38
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 37
• 125000005842 heteroatom Chemical group 0.000 claims description 30
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 29
• 125000002837 carbocyclic group Chemical group 0.000 claims description 27
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 25
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 25
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 24
• 239000004305 biphenyl Substances 0.000 claims description 24
• 235000010290 biphenyl Nutrition 0.000 claims description 23
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
• 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 20
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 19
• UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 18
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 18
• 125000002950 monocyclic group Chemical group 0.000 claims description 18
• 230000004913 activation Effects 0.000 claims description 17
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 16
• 238000002360 preparation method Methods 0.000 claims description 15
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 12
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 12
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 10
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 10
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 10
• 150000003536 tetrazoles Chemical class 0.000 claims description 10
• RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 9
• 125000004122 cyclic group Chemical group 0.000 claims description 9
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 9
• 150000003852 triazoles Chemical class 0.000 claims description 9
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
• VDQQJMHXZCMNMU-UHFFFAOYSA-N 1-phenylpyrrolidine Chemical compound C1CCCN1C1=CC=CC=C1 VDQQJMHXZCMNMU-UHFFFAOYSA-N 0.000 claims description 8
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 8
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
• WYKHSBAVLOPISI-UHFFFAOYSA-N 2-phenyl-1,3-thiazole Chemical compound C1=CSC(C=2C=CC=CC=2)=N1 WYKHSBAVLOPISI-UHFFFAOYSA-N 0.000 claims description 7
• GCXNJAXHHFZVIM-UHFFFAOYSA-N 2-phenylfuran Chemical compound C1=COC(C=2C=CC=CC=2)=C1 GCXNJAXHHFZVIM-UHFFFAOYSA-N 0.000 claims description 7
• VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims description 7
• LUEYUHCBBXWTQT-UHFFFAOYSA-N 4-phenyl-2h-triazole Chemical compound C1=NNN=C1C1=CC=CC=C1 LUEYUHCBBXWTQT-UHFFFAOYSA-N 0.000 claims description 7
• HTDLSAGEOYDVSJ-UHFFFAOYSA-N 4-phenyloxadiazole Chemical compound O1N=NC(C=2C=CC=CC=2)=C1 HTDLSAGEOYDVSJ-UHFFFAOYSA-N 0.000 claims description 7
• OEDUIFSDODUDRK-UHFFFAOYSA-N 5-phenyl-1h-pyrazole Chemical compound N1N=CC=C1C1=CC=CC=C1 OEDUIFSDODUDRK-UHFFFAOYSA-N 0.000 claims description 7
• 241001510512 Chlamydia phage 2 Species 0.000 claims description 7
• 241000124008 Mammalia Species 0.000 claims description 7
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 7
• YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims description 7
• LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 claims description 7
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
• 102100031272 Calcineurin B homologous protein 2 Human genes 0.000 claims description 6
• 101000777239 Homo sapiens Calcineurin B homologous protein 2 Proteins 0.000 claims description 6
• 206010028980 Neoplasm Diseases 0.000 claims description 6
• 201000011510 cancer Diseases 0.000 claims description 6
• 230000001419 dependent effect Effects 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• VBXZSFNZVNDOPB-UHFFFAOYSA-N 1,4,5,6-tetrahydropyrimidine Chemical compound C1CNC=NC1 VBXZSFNZVNDOPB-UHFFFAOYSA-N 0.000 claims description 4
• FFMBYMANYCDCMK-UHFFFAOYSA-N 2,5-dihydro-1h-imidazole Chemical compound C1NCN=C1 FFMBYMANYCDCMK-UHFFFAOYSA-N 0.000 claims description 4
• XXOKRPMJWBWION-UHFFFAOYSA-N 3-phenyl-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole Chemical compound C1NCC=2C1=NNC=2C1=CC=CC=C1 XXOKRPMJWBWION-UHFFFAOYSA-N 0.000 claims description 4
• 239000000594 mannitol Substances 0.000 claims description 4
• OVFAVILXKKMJII-UHFFFAOYSA-N 1,1'-biphenyl;1,3-thiazole Chemical compound C1=CSC=N1.C1=CC=CC=C1C1=CC=CC=C1 OVFAVILXKKMJII-UHFFFAOYSA-N 0.000 claims description 3
• REUDPRVPPDWOKE-UHFFFAOYSA-N 1,1'-biphenyl;1h-imidazole Chemical compound C1=CNC=N1.C1=CC=CC=C1C1=CC=CC=C1 REUDPRVPPDWOKE-UHFFFAOYSA-N 0.000 claims description 3
• ACGSIYWQEKAUJY-UHFFFAOYSA-N 1,1'-biphenyl;1h-pyrazole Chemical compound C=1C=NNC=1.C1=CC=CC=C1C1=CC=CC=C1 ACGSIYWQEKAUJY-UHFFFAOYSA-N 0.000 claims description 3
• NWAUPHAHIDQCHS-UHFFFAOYSA-N 1,1'-biphenyl;2h-tetrazole Chemical compound C1=NN=NN1.C1=CC=CC=C1C1=CC=CC=C1 NWAUPHAHIDQCHS-UHFFFAOYSA-N 0.000 claims description 3
• DADCHRIIDRATMM-UHFFFAOYSA-N 1,1'-biphenyl;2h-triazole Chemical compound C1=CNN=N1.C1=CC=CC=C1C1=CC=CC=C1 DADCHRIIDRATMM-UHFFFAOYSA-N 0.000 claims description 3
• VIYYJNULAUUYDE-UHFFFAOYSA-N 1,1'-biphenyl;oxadiazole Chemical compound C1=CON=N1.C1=CC=CC=C1C1=CC=CC=C1 VIYYJNULAUUYDE-UHFFFAOYSA-N 0.000 claims description 3
• DZSJSINILAREKA-UHFFFAOYSA-N 1,5-dihydropyrrolo[3,4-c]pyrazole Chemical compound N1C=C2NN=CC2=C1 DZSJSINILAREKA-UHFFFAOYSA-N 0.000 claims description 3
• MOPJTVJSWFNKEW-UHFFFAOYSA-N 2-phenylpyridine;1h-pyrazole Chemical compound C=1C=NNC=1.C1=CC=CC=C1C1=CC=CC=N1 MOPJTVJSWFNKEW-UHFFFAOYSA-N 0.000 claims description 3
• SDNQEQRONOHSEB-UHFFFAOYSA-N C1NC=CN1.C1=CC=CC=C1C1=CC=CC=C1 Chemical compound C1NC=CN1.C1=CC=CC=C1C1=CC=CC=C1 SDNQEQRONOHSEB-UHFFFAOYSA-N 0.000 claims description 3
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