JP2007505085A - ベンゾイミダゾールアセトニトリル - Google Patents

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Publication number

JP2007505085A

JP2007505085A JP2006525833A JP2006525833A JP2007505085A JP 2007505085 A JP2007505085 A JP 2007505085A JP 2006525833 A JP2006525833 A JP 2006525833A JP 2006525833 A JP2006525833 A JP 2006525833A JP 2007505085 A JP2007505085 A JP 2007505085A

Authority

JP

Japan

Prior art keywords

ethyl

benzimidazol

dihydro

acetonitrile

ylidene

Prior art date

2003-09-12

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.)

Pending

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• Espacenet
• Global Dossier
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• GVAAUBDAYOGTMQ-UHFFFAOYSA-N acetonitrile;1h-benzimidazole Chemical compound CC#N.C1=CC=C2NC=NC2=C1 GVAAUBDAYOGTMQ-UHFFFAOYSA-N 0.000 title claims abstract description 48
• -1 amino, carboxy, aminocarbonyl Chemical group 0.000 claims abstract description 177
• 238000000034 method Methods 0.000 claims abstract description 177
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 66
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 48
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 41
• 125000003118 aryl group Chemical group 0.000 claims abstract description 38
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 36
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
• 239000001257 hydrogen Substances 0.000 claims abstract description 21
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 20
• 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 20
• 239000008103 glucose Substances 0.000 claims abstract description 20
• 201000010065 polycystic ovary syndrome Diseases 0.000 claims abstract description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
• 201000001421 hyperglycemia Diseases 0.000 claims abstract description 9
• 208000008589 Obesity Diseases 0.000 claims abstract description 7
• 125000004442 acylamino group Chemical group 0.000 claims abstract description 7
• 208000030159 metabolic disease Diseases 0.000 claims abstract description 7
• 235000020824 obesity Nutrition 0.000 claims abstract description 7
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
• 230000001404 mediated effect Effects 0.000 claims abstract description 6
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 6
• 125000003277 amino group Chemical group 0.000 claims abstract description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 5
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
• 150000001875 compounds Chemical class 0.000 claims description 154
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 70
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 54
• WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 39
• 125000001072 heteroaryl group Chemical group 0.000 claims description 37
• 102000004877 Insulin Human genes 0.000 claims description 27
• 108090001061 Insulin Proteins 0.000 claims description 27
• 229940125396 insulin Drugs 0.000 claims description 27
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 20
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
• 239000000203 mixture Substances 0.000 claims description 20
• 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 claims description 17
• 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims description 17
• 150000003839 salts Chemical class 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 14
• 150000002431 hydrogen Chemical class 0.000 claims description 14
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• RRGGROIZKNSXNR-RELWKKBWSA-N tert-butyl 3-[[4-[(z)-cyano-(3-ethyl-1h-benzimidazol-2-ylidene)methyl]-5-methylpyrimidin-2-yl]carbamoyl]pyrrolidine-1-carboxylate Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NC(=O)C1CCN(C(=O)OC(C)(C)C)C1 RRGGROIZKNSXNR-RELWKKBWSA-N 0.000 claims description 9
• 229910052736 halogen Inorganic materials 0.000 claims description 8
• 150000002367 halogens Chemical class 0.000 claims description 8
• 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 7
• 229920006395 saturated elastomer Polymers 0.000 claims description 7
• YCVWINWKMLREOP-COYFKBPASA-N (4s)-n-[4-[(z)-cyano-(3-ethyl-1h-benzimidazol-2-ylidene)methyl]-5-methylpyrimidin-2-yl]-1,3-thiazolidine-4-carboxamide Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NC(=O)[C@H]1CSCN1 YCVWINWKMLREOP-COYFKBPASA-N 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• SEAQTHCVAGBRFY-INWYIAFRSA-N (2r,4s)-6-fluoro-2-methylspiro[2,3-dihydrochromene-4,5'-imidazolidine]-2',4'-dione Chemical compound C([C@H](OC1=CC=C(F)C=C11)C)[C@@]21NC(=O)NC2=O SEAQTHCVAGBRFY-INWYIAFRSA-N 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• CHNUOJQWGUIOLD-NFZZJPOKSA-N epalrestat Chemical compound C=1C=CC=CC=1\C=C(/C)\C=C1/SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-NFZZJPOKSA-N 0.000 claims description 5
• 229950010170 epalrestat Drugs 0.000 claims description 5
• 229910052757 nitrogen Inorganic materials 0.000 claims description 5
• JFPZAMGLUXPGJQ-CAPFRKAQSA-N (2z)-2-(3-ethyl-1h-benzimidazol-2-ylidene)-2-[2-(3-pyrazol-1-ylpropylamino)pyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(N=1)=CC=NC=1NCCCN1C=CC=N1 JFPZAMGLUXPGJQ-CAPFRKAQSA-N 0.000 claims description 4
• RHSQSWWCNGUHFC-HEHNFIMWSA-N (2z)-2-(3-ethyl-1h-benzimidazol-2-ylidene)-2-[5-methyl-2-[(1-methylpiperidin-4-yl)amino]pyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NC1CCN(C)CC1 RHSQSWWCNGUHFC-HEHNFIMWSA-N 0.000 claims description 4
• 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 4
• TUWHXVNPMWRVKR-UHFFFAOYSA-N 2-[2-[3-(2-oxopyrrolidin-1-yl)propylamino]pyrimidin-4-yl]acetonitrile Chemical compound O=C1CCCN1CCCNC1=NC=CC(CC#N)=N1 TUWHXVNPMWRVKR-UHFFFAOYSA-N 0.000 claims description 4
• OVKXDANNQWXYKF-UHFFFAOYSA-N 2-methyloctanamide Chemical compound CCCCCCC(C)C(N)=O OVKXDANNQWXYKF-UHFFFAOYSA-N 0.000 claims description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
• 229940100389 Sulfonylurea Drugs 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 239000003112 inhibitor Substances 0.000 claims description 4
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 4
• SXONDGSPUVNZLO-UHFFFAOYSA-N zenarestat Chemical compound O=C1N(CC(=O)O)C2=CC(Cl)=CC=C2C(=O)N1CC1=CC=C(Br)C=C1F SXONDGSPUVNZLO-UHFFFAOYSA-N 0.000 claims description 4
• 229950006343 zenarestat Drugs 0.000 claims description 4
• WMASQBHSXPTQIJ-ZAFFBPSHSA-N (1r,5r,7r)-n-[4-[(z)-cyano-(3-ethyl-1h-benzimidazol-2-ylidene)methyl]-5-methylpyrimidin-2-yl]-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-carboxamide Chemical compound N\1C2=CC=CC=C2N(CC)C/1=C(\C#N)C1=NC(NC(=O)[C@H]2[C@@]3([H])CNC[C@](O3)(O2)[H])=NC=C1C WMASQBHSXPTQIJ-ZAFFBPSHSA-N 0.000 claims description 3
• XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 claims description 3
• DDVNZPBCWLCHHP-CAPFRKAQSA-N (2z)-2-(3-ethyl-1h-benzimidazol-2-ylidene)-2-[2-(2-imidazol-1-ylethylamino)-5-methylpyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NCCN1C=CN=C1 DDVNZPBCWLCHHP-CAPFRKAQSA-N 0.000 claims description 3
• YQZPLFKEVGBUBM-CAPFRKAQSA-N (2z)-2-(3-ethyl-1h-benzimidazol-2-ylidene)-2-[2-[2-(1h-imidazol-5-yl)ethylamino]-5-methylpyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NCCC1=CNC=N1 YQZPLFKEVGBUBM-CAPFRKAQSA-N 0.000 claims description 3
• LZYUNMYBEZQFTD-XDJHFCHBSA-N (2z)-2-(3-ethyl-1h-benzimidazol-2-ylidene)-2-[2-[2-(1h-imidazol-5-yl)ethylamino]pyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(N=1)=CC=NC=1NCCC1=CNC=N1 LZYUNMYBEZQFTD-XDJHFCHBSA-N 0.000 claims description 3
• ZDACKGNFEATCSO-XDJHFCHBSA-N (2z)-2-(3-ethyl-1h-benzimidazol-2-ylidene)-2-[2-[3-(1,2,4-triazol-1-yl)propylamino]pyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(N=1)=CC=NC=1NCCCN1C=NC=N1 ZDACKGNFEATCSO-XDJHFCHBSA-N 0.000 claims description 3
• XRWHEPGKBFENFV-XDJHFCHBSA-N (2z)-2-(3-ethyl-1h-benzimidazol-2-ylidene)-2-[5-methyl-2-(2-methylpropylamino)pyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C1=NC(NCC(C)C)=NC=C1C XRWHEPGKBFENFV-XDJHFCHBSA-N 0.000 claims description 3
• AURMLXSMQYFGKW-RELWKKBWSA-N (2z)-2-(3-ethyl-1h-benzimidazol-2-ylidene)-2-[5-methyl-2-(2-piperidin-1-ylethylamino)pyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NCCN1CCCCC1 AURMLXSMQYFGKW-RELWKKBWSA-N 0.000 claims description 3
• PTZQHCCTCVQRJR-HEHNFIMWSA-N (2z)-2-(3-ethyl-1h-benzimidazol-2-ylidene)-2-[5-methyl-2-(3-pyrazol-1-ylpropylamino)pyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NCCCN1C=CC=N1 PTZQHCCTCVQRJR-HEHNFIMWSA-N 0.000 claims description 3
• LFWFNXNKIKCCOT-CAPFRKAQSA-N (2z)-2-(3-ethyl-1h-benzimidazol-2-ylidene)-2-[5-methyl-2-(piperidin-4-ylamino)pyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NC1CCNCC1 LFWFNXNKIKCCOT-CAPFRKAQSA-N 0.000 claims description 3
• RBNRLRZYGUTKBO-CAPFRKAQSA-N (2z)-2-(3-ethyl-1h-benzimidazol-2-ylidene)-2-[5-methyl-2-[3-(1,2,4-triazol-1-yl)propylamino]pyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NCCCN1C=NC=N1 RBNRLRZYGUTKBO-CAPFRKAQSA-N 0.000 claims description 3
• VCIMMQBMHZWKFT-OQKWZONESA-N (2z)-2-(3-ethyl-1h-benzimidazol-2-ylidene)-2-[5-methyl-2-[3-(2-oxopyrrolidin-1-yl)propylamino]pyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NCCCN1CCCC1=O VCIMMQBMHZWKFT-OQKWZONESA-N 0.000 claims description 3
• BFZLBFGOLMHLFP-XDJHFCHBSA-N (2z)-2-[2-(cyclobutylamino)-5-methylpyrimidin-4-yl]-2-(3-ethyl-1h-benzimidazol-2-ylidene)acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NC1CCC1 BFZLBFGOLMHLFP-XDJHFCHBSA-N 0.000 claims description 3
• GSZIQJGZEVBYIZ-NBVRZTHBSA-N (2z)-2-[2-(cyclobutylamino)pyrimidin-4-yl]-2-(3-ethyl-1h-benzimidazol-2-ylidene)acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(N=1)=CC=NC=1NC1CCC1 GSZIQJGZEVBYIZ-NBVRZTHBSA-N 0.000 claims description 3
• RYGLSICAFNZNMP-HEHNFIMWSA-N (2z)-2-[2-(cyclohexylamino)-5-methylpyrimidin-4-yl]-2-(3-ethyl-1h-benzimidazol-2-ylidene)acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NC1CCCCC1 RYGLSICAFNZNMP-HEHNFIMWSA-N 0.000 claims description 3
• VJSBFVAZJBHKHH-GHRIWEEISA-N (2z)-2-[2-(ethylamino)-5-methylpyrimidin-4-yl]-2-(3-ethyl-1h-benzimidazol-2-ylidene)acetonitrile Chemical compound CCNC1=NC=C(C)C(C(\C#N)=C/2N(C3=CC=CC=C3N\2)CC)=N1 VJSBFVAZJBHKHH-GHRIWEEISA-N 0.000 claims description 3
• ZGGNPKDLUKSQGX-RELWKKBWSA-N 1-acetyl-n-[4-[(z)-cyano-(3-ethyl-1h-benzimidazol-2-ylidene)methyl]-5-methylpyrimidin-2-yl]piperidine-4-carboxamide Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NC(=O)C1CCN(C(C)=O)CC1 ZGGNPKDLUKSQGX-RELWKKBWSA-N 0.000 claims description 3
• QCCHBHSAIQIQGO-UHFFFAOYSA-N 2,7-difluorospiro[fluorene-9,5'-imidazolidine]-2',4'-dione Chemical compound C12=CC(F)=CC=C2C2=CC=C(F)C=C2C21NC(=O)NC2=O QCCHBHSAIQIQGO-UHFFFAOYSA-N 0.000 claims description 3
• NRKMCUJASWHRQT-UHFFFAOYSA-N 2-(1,3-dihydrobenzimidazol-2-ylidene)-2-[5-methyl-2-[3-(2-oxopyrrolidin-1-yl)propylamino]pyrimidin-4-yl]acetonitrile Chemical compound N1=C(C(C#N)=C2NC3=CC=CC=C3N2)C(C)=CN=C1NCCCN1CCCC1=O NRKMCUJASWHRQT-UHFFFAOYSA-N 0.000 claims description 3
• HSQAVTQYJVNJDR-UHFFFAOYSA-N 2-(1-ethylbenzimidazol-2-yl)-2-[2-(furan-2-ylmethylamino)-5-methylpyrimidin-4-yl]acetonitrile Chemical compound N=1C2=CC=CC=C2N(CC)C=1C(C#N)C(C(=CN=1)C)=NC=1NCC1=CC=CO1 HSQAVTQYJVNJDR-UHFFFAOYSA-N 0.000 claims description 3
• HPNDCMCOYAJERV-UHFFFAOYSA-N 2-(1h-benzimidazol-2-yl)-2-[5-methyl-2-(2-pyridin-3-ylethylamino)pyrimidin-4-yl]acetonitrile Chemical compound N1=C(C(C#N)C=2NC3=CC=CC=C3N=2)C(C)=CN=C1NCCC1=CC=CN=C1 HPNDCMCOYAJERV-UHFFFAOYSA-N 0.000 claims description 3
• NMMDPTXPHURZBR-UHFFFAOYSA-N 2-[2-(cyclohexylamino)pyrimidin-4-yl]-2-(1-ethylbenzimidazol-2-yl)acetonitrile Chemical compound N=1C2=CC=CC=C2N(CC)C=1C(C#N)C(N=1)=CC=NC=1NC1CCCCC1 NMMDPTXPHURZBR-UHFFFAOYSA-N 0.000 claims description 3
• FQRCAUUSVDRERL-UHFFFAOYSA-N 2-[2-(cyclohexylmethylamino)-5-methylpyrimidin-4-yl]-2-(1-ethylbenzimidazol-2-yl)acetonitrile Chemical compound N=1C2=CC=CC=C2N(CC)C=1C(C#N)C(C(=CN=1)C)=NC=1NCC1CCCCC1 FQRCAUUSVDRERL-UHFFFAOYSA-N 0.000 claims description 3
• ZVHRVTZDDQMAJA-UHFFFAOYSA-N 2-[2-(cyclopentylamino)-5-methylpyrimidin-4-yl]-2-(1,3-diethylbenzimidazol-2-ylidene)acetonitrile Chemical compound CCN1C2=CC=CC=C2N(CC)C1=C(C#N)C(C(=CN=1)C)=NC=1NC1CCCC1 ZVHRVTZDDQMAJA-UHFFFAOYSA-N 0.000 claims description 3
• ONTIOJUGXBWDJB-UHFFFAOYSA-N 2-[2-(cyclopentylamino)-5-methylpyrimidin-4-yl]-2-(1-ethylbenzimidazol-2-yl)acetonitrile Chemical compound N=1C2=CC=CC=C2N(CC)C=1C(C#N)C(C(=CN=1)C)=NC=1NC1CCCC1 ONTIOJUGXBWDJB-UHFFFAOYSA-N 0.000 claims description 3
• DUZYLYSYBVQFFG-UHFFFAOYSA-N 2-[2-[2-[6-(dimethylamino)pyridin-3-yl]ethylamino]-5-methylpyrimidin-4-yl]-2-(1-ethylbenzimidazol-2-yl)acetonitrile Chemical compound N=1C2=CC=CC=C2N(CC)C=1C(C#N)C(C(=CN=1)C)=NC=1NCCC1=CC=C(N(C)C)N=C1 DUZYLYSYBVQFFG-UHFFFAOYSA-N 0.000 claims description 3
• VAEWDFXXHLHBTG-UHFFFAOYSA-N 2-[2-[2-[6-(dimethylamino)pyridin-3-yl]ethylamino]pyrimidin-4-yl]-2-(1-ethylbenzimidazol-2-yl)acetonitrile Chemical compound N=1C2=CC=CC=C2N(CC)C=1C(C#N)C(N=1)=CC=NC=1NCCC1=CC=C(N(C)C)N=C1 VAEWDFXXHLHBTG-UHFFFAOYSA-N 0.000 claims description 3
• BCSVCWVQNOXFGL-UHFFFAOYSA-N 3,4-dihydro-4-oxo-3-((5-trifluoromethyl-2-benzothiazolyl)methyl)-1-phthalazine acetic acid Chemical compound O=C1C2=CC=CC=C2C(CC(=O)O)=NN1CC1=NC2=CC(C(F)(F)F)=CC=C2S1 BCSVCWVQNOXFGL-UHFFFAOYSA-N 0.000 claims description 3
• XFVQELOCUVVHQJ-LTGZKZEYSA-N 4-acetyl-n-[4-[(z)-cyano-(3-ethyl-1h-benzimidazol-2-ylidene)methyl]-5-methylpyrimidin-2-yl]morpholine-2-carboxamide Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NC(=O)C1CN(C(C)=O)CCO1 XFVQELOCUVVHQJ-LTGZKZEYSA-N 0.000 claims description 3
• 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims description 3
• 229940123208 Biguanide Drugs 0.000 claims description 3
• 229940122254 Intermediate acting insulin Drugs 0.000 claims description 3
• 102000016261 Long-Acting Insulin Human genes 0.000 claims description 3
• 108010092217 Long-Acting Insulin Proteins 0.000 claims description 3
• 229940100066 Long-acting insulin Drugs 0.000 claims description 3
• IBAQFPQHRJAVAV-ULAWRXDQSA-N Miglitol Chemical compound OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO IBAQFPQHRJAVAV-ULAWRXDQSA-N 0.000 claims description 3
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