ZA200705471B - Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto - Google Patents

Info

Publication number

ZA200705471B

ZA200705471B ZA200705471A ZA200705471A ZA200705471B ZA 200705471 B ZA200705471 B ZA 200705471B ZA 200705471 A ZA200705471 A ZA 200705471A ZA 200705471 A ZA200705471 A ZA 200705471A ZA 200705471 B ZA200705471 B ZA 200705471B

Authority

ZA

South Africa

Prior art keywords

pyridin

methoxy

piperidine

yloxy

carboxylic acid

Prior art date

2005-01-10

Links

• Espacenet
• Global Dossier
• Discuss

• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 101
• 208000035475 disorder Diseases 0.000 title claims description 69
• 238000011282 treatment Methods 0.000 title claims description 47
• 125000000714 pyrimidinyl group Chemical group 0.000 title description 6
• 230000004060 metabolic process Effects 0.000 title description 4
• 125000004076 pyridyl group Chemical group 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims description 373
• -1 5-isopropyl-[1,2,4]oxadiazol-3-yl Chemical group 0.000 claims description 147
• 238000000034 method Methods 0.000 claims description 81
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 66
• 239000008103 glucose Substances 0.000 claims description 58
• 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 description 57
• 230000002503 metabolic effect Effects 0.000 claims description 49
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 47
• 239000008194 pharmaceutical composition Substances 0.000 claims description 38
• 125000000217 alkyl group Chemical group 0.000 claims description 34
• 150000003839 salts Chemical class 0.000 claims description 34
• 239000003814 drug Substances 0.000 claims description 32
• 125000003545 alkoxy group Chemical group 0.000 claims description 30
• 239000000556 agonist Substances 0.000 claims description 28
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims description 24
• 238000004519 manufacturing process Methods 0.000 claims description 24
• 150000002148 esters Chemical class 0.000 claims description 23
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
• 239000012453 solvate Substances 0.000 claims description 21
• 201000001421 hyperglycemia Diseases 0.000 claims description 20
• 208000011580 syndromic disease Diseases 0.000 claims description 20
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 19
• 206010022489 Insulin Resistance Diseases 0.000 claims description 19
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 241001465754 Metazoa Species 0.000 claims description 17
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 16
• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 16
• 229910052801 chlorine Inorganic materials 0.000 claims description 16
• 230000003247 decreasing effect Effects 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 229910052731 fluorine Inorganic materials 0.000 claims description 15
• 125000001424 substituent group Chemical group 0.000 claims description 14
• 239000003937 drug carrier Substances 0.000 claims description 13
• 208000006575 hypertriglyceridemia Diseases 0.000 claims description 13
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 13
• 230000037406 food intake Effects 0.000 claims description 12
• 235000012631 food intake Nutrition 0.000 claims description 12
• 230000036186 satiety Effects 0.000 claims description 11
• 235000019627 satiety Nutrition 0.000 claims description 11
• 208000035150 Hypercholesterolemia Diseases 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 10
• 150000002367 halogens Chemical class 0.000 claims description 10
• 230000004584 weight gain Effects 0.000 claims description 10
• 235000019786 weight gain Nutrition 0.000 claims description 10
• 125000000623 heterocyclic group Chemical group 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 230000001939 inductive effect Effects 0.000 claims description 8
• 125000005431 alkyl carboxamide group Chemical group 0.000 claims description 7
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 238000002560 therapeutic procedure Methods 0.000 claims description 7
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 6
• 125000003282 alkyl amino group Chemical group 0.000 claims description 5
• 125000004414 alkyl thio group Chemical group 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• WPDCHTSXOPUOII-UHFFFAOYSA-N propan-2-yl 4-[5-methoxy-6-[(2-methyl-6-methylsulfonylpyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(S(C)(=O)=O)N=C1C WPDCHTSXOPUOII-UHFFFAOYSA-N 0.000 claims description 4
• LMZNHYOLIUYJBZ-UHFFFAOYSA-N propan-2-yl 4-[5-methoxy-6-[[6-(2-methoxyethylamino)-2-methylpyridin-3-yl]amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound CC1=NC(NCCOC)=CC=C1NC1=NC=NC(OC2CCN(CC2)C(=O)OC(C)C)=C1OC LMZNHYOLIUYJBZ-UHFFFAOYSA-N 0.000 claims description 4
• 229940124530 sulfonamide Drugs 0.000 claims description 4
• 150000003456 sulfonamides Chemical class 0.000 claims description 4
• CDBFPJAYSVCXAU-UHFFFAOYSA-N propan-2-yl 4-[5-methoxy-6-(2-methoxy-4-methylsulfonylanilino)pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound COC1=CC(S(C)(=O)=O)=CC=C1NC1=NC=NC(OC2CCN(CC2)C(=O)OC(C)C)=C1OC CDBFPJAYSVCXAU-UHFFFAOYSA-N 0.000 claims description 3
• PLDNGZQJBABRGF-UHFFFAOYSA-N propan-2-yl 4-[6-[(2,4-dimethyl-6-methylsulfonylpyridin-3-yl)amino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=C(C)C=C(S(C)(=O)=O)N=C1C PLDNGZQJBABRGF-UHFFFAOYSA-N 0.000 claims description 3
• WQZACNXSRNOJLP-UHFFFAOYSA-N propan-2-yl 4-[6-[(2-methyl-6-methylsulfonylpyridin-3-yl)amino]-5-propoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OCCC)=C1NC1=CC=C(S(C)(=O)=O)N=C1C WQZACNXSRNOJLP-UHFFFAOYSA-N 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• 229910052791 calcium Inorganic materials 0.000 claims description 2
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
• BQBRAHFIBXQWOD-UHFFFAOYSA-N propan-2-yl 4-[5-methoxy-6-[(2-methyl-6-propylsulfonylpyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound CC1=NC(S(=O)(=O)CCC)=CC=C1NC1=NC=NC(OC2CCN(CC2)C(=O)OC(C)C)=C1OC BQBRAHFIBXQWOD-UHFFFAOYSA-N 0.000 claims description 2
• PXMWCGIHDBPCJK-UHFFFAOYSA-N propan-2-yl 4-[6-[(2-methyl-6-methylsulfonylpyridin-3-yl)amino]-5-propan-2-yloxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1OC1=NC=NC(NC=2C(=NC(=CC=2)S(C)(=O)=O)C)=C1OC(C)C PXMWCGIHDBPCJK-UHFFFAOYSA-N 0.000 claims description 2
• QOMDWSGBVDKXCL-UHFFFAOYSA-N propan-2-yl 4-[6-[(6-ethylsulfanyl-2-methylpyridin-3-yl)amino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound CC1=NC(SCC)=CC=C1NC1=NC=NC(OC2CCN(CC2)C(=O)OC(C)C)=C1OC QOMDWSGBVDKXCL-UHFFFAOYSA-N 0.000 claims description 2
• WSTZRNTYYSAKNN-UHFFFAOYSA-N propan-2-yl 4-[6-[(6-ethylsulfonyl-2-methylpyridin-3-yl)amino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound CC1=NC(S(=O)(=O)CC)=CC=C1NC1=NC=NC(OC2CCN(CC2)C(=O)OC(C)C)=C1OC WSTZRNTYYSAKNN-UHFFFAOYSA-N 0.000 claims description 2
• LTXALNIADPOIIN-UHFFFAOYSA-N propan-2-yl 4-[6-[[6-(2-hydroxyethyl)-2-methylpyridin-3-yl]amino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(CCO)N=C1C LTXALNIADPOIIN-UHFFFAOYSA-N 0.000 claims description 2
• GLGNFUFVRYHVPF-UHFFFAOYSA-N propan-2-yl 4-[6-[[6-(2-hydroxyethylsulfonyl)-2-methylpyridin-3-yl]amino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(S(=O)(=O)CCO)N=C1C GLGNFUFVRYHVPF-UHFFFAOYSA-N 0.000 claims description 2
• OSIPUASQVRYBFL-UHFFFAOYSA-N 1-cyclopropylethyl 4-[5-methoxy-6-[[2-methyl-6-(2-methylsulfonylethyl)pyridin-3-yl]amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C2CC2)C(OC)=C1NC1=CC=C(CCS(C)(=O)=O)N=C1C OSIPUASQVRYBFL-UHFFFAOYSA-N 0.000 claims 1
• TYVVVLWZVDLMKH-UHFFFAOYSA-N 4-[5-hydroxy-6-[(2-methyl-6-methylsulfonylpyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylic acid Chemical compound CC1=NC(S(C)(=O)=O)=CC=C1NC1=NC=NC(OC2CCN(CC2)C(O)=O)=C1O TYVVVLWZVDLMKH-UHFFFAOYSA-N 0.000 claims 1
• OSDYPSRERYXGAL-UHFFFAOYSA-N OCCCOC1=CC=C(C(=N1)C)NC1=NC=CC(=C1OC)OC1CCN(CC1)C(=O)O Chemical compound OCCCOC1=CC=C(C(=N1)C)NC1=NC=CC(=C1OC)OC1CCN(CC1)C(=O)O OSDYPSRERYXGAL-UHFFFAOYSA-N 0.000 claims 1
• TZZSFQVNBOIXEM-UHFFFAOYSA-N butan-2-yl 4-[5-methoxy-6-[(2-methyl-6-methylsulfonylpyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)CC)CCC1OC1=NC=NC(NC=2C(=NC(=CC=2)S(C)(=O)=O)C)=C1OC TZZSFQVNBOIXEM-UHFFFAOYSA-N 0.000 claims 1
• WMHNUYUKWMFEBB-UHFFFAOYSA-N n-(2-fluoro-4-methylsulfonylphenyl)-3-methoxy-4-[1-(5-methoxypyrimidin-2-yl)piperidin-4-yl]oxypyridin-2-amine Chemical compound N1=CC(OC)=CN=C1N1CCC(OC=2C(=C(NC=3C(=CC(=CC=3)S(C)(=O)=O)F)N=CC=2)OC)CC1 WMHNUYUKWMFEBB-UHFFFAOYSA-N 0.000 claims 1
• MZTINHLSNWZIGX-UHFFFAOYSA-N propan-2-yl 4-[2-(2-chloro-4-cyanoanilino)-3-methoxypyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CC=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(C#N)C=C1Cl MZTINHLSNWZIGX-UHFFFAOYSA-N 0.000 claims 1
• SRFUCJDALAUAOF-UHFFFAOYSA-N propan-2-yl 4-[2-(2-chloro-4-methylsulfonylanilino)-5-fluoro-3-methoxypyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CC(F)=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(S(C)(=O)=O)C=C1Cl SRFUCJDALAUAOF-UHFFFAOYSA-N 0.000 claims 1
• LCVBRNXBVIFWEL-UHFFFAOYSA-N propan-2-yl 4-[2-(2-chloro-4-propoxyanilino)-3-methoxypyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound ClC1=CC(OCCC)=CC=C1NC1=NC=CC(OC2CCN(CC2)C(=O)OC(C)C)=C1OC LCVBRNXBVIFWEL-UHFFFAOYSA-N 0.000 claims 1
• WIQYJNMJAJKHDL-UHFFFAOYSA-N propan-2-yl 4-[2-(2-fluoro-4-methylsulfonylanilino)-3-hydroxypyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1OC1=CC=NC(NC=2C(=CC(=CC=2)S(C)(=O)=O)F)=C1O WIQYJNMJAJKHDL-UHFFFAOYSA-N 0.000 claims 1
• GLLYOXLYQNNITQ-UHFFFAOYSA-N propan-2-yl 4-[2-(4-cyano-2-fluoroanilino)-3-methoxypyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CC=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(C#N)C=C1F GLLYOXLYQNNITQ-UHFFFAOYSA-N 0.000 claims 1
• KLCSMIJBTGOTGD-UHFFFAOYSA-N propan-2-yl 4-[2-(5-fluoro-2-methyl-4-propoxyanilino)-3-methoxypyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=C(F)C(OCCC)=CC(C)=C1NC1=NC=CC(OC2CCN(CC2)C(=O)OC(C)C)=C1OC KLCSMIJBTGOTGD-UHFFFAOYSA-N 0.000 claims 1
• XWUUNOMDKUGWSZ-UHFFFAOYSA-N propan-2-yl 4-[2-[2-ethyl-4-(2-methylsulfonylethyl)anilino]-3-methoxypyridin-4-yl]oxy-2-methylpiperidine-1-carboxylate Chemical compound CCC1=CC(CCS(C)(=O)=O)=CC=C1NC1=NC=CC(OC2CC(C)N(CC2)C(=O)OC(C)C)=C1OC XWUUNOMDKUGWSZ-UHFFFAOYSA-N 0.000 claims 1
• XQQUPYUYDYQVIZ-UHFFFAOYSA-N propan-2-yl 4-[2-[2-fluoro-4-(2-hydroxyethoxy)anilino]-3-methoxypyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=CN=C(NC=2C(=CC(OCCO)=CC=2)F)C(OC)=C1OC1CCN(C(=O)OC(C)C)CC1 XQQUPYUYDYQVIZ-UHFFFAOYSA-N 0.000 claims 1
• CSMAWTDRUGNYDW-UHFFFAOYSA-N propan-2-yl 4-[2-[2-fluoro-4-(2-hydroxyethyl)anilino]-3-methoxypyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=CN=C(NC=2C(=CC(CCO)=CC=2)F)C(OC)=C1OC1CCN(C(=O)OC(C)C)CC1 CSMAWTDRUGNYDW-UHFFFAOYSA-N 0.000 claims 1
• PIFXDDDSSQRPQZ-UHFFFAOYSA-N propan-2-yl 4-[2-[2-fluoro-4-(2-hydroxyethylsulfonyl)anilino]-3-methoxypyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=CN=C(NC=2C(=CC(=CC=2)S(=O)(=O)CCO)F)C(OC)=C1OC1CCN(C(=O)OC(C)C)CC1 PIFXDDDSSQRPQZ-UHFFFAOYSA-N 0.000 claims 1
• HSJMHVOZSKQOTD-UHFFFAOYSA-N propan-2-yl 4-[2-[2-fluoro-4-(3-phosphonooxypropyl)anilino]-3-methoxypyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=CN=C(NC=2C(=CC(CCCOP(O)(O)=O)=CC=2)F)C(OC)=C1OC1CCN(C(=O)OC(C)C)CC1 HSJMHVOZSKQOTD-UHFFFAOYSA-N 0.000 claims 1
• GJKUZOONRDBIJI-UHFFFAOYSA-N propan-2-yl 4-[2-[[6-(2-cyclopropyloxyethyl)-2-methylpyridin-3-yl]amino]-3-methoxypyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CC=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC(C(=N1)C)=CC=C1CCOC1CC1 GJKUZOONRDBIJI-UHFFFAOYSA-N 0.000 claims 1
• AIIOSRIZUDWTOU-UHFFFAOYSA-N propan-2-yl 4-[2-[[6-(2-hydroxyethyl)-2-methylpyridin-3-yl]amino]-3-methoxypyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CC=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(CCO)N=C1C AIIOSRIZUDWTOU-UHFFFAOYSA-N 0.000 claims 1
• NQFFYUUJBUOFDJ-UHFFFAOYSA-N propan-2-yl 4-[2-[[6-(2-hydroxyethylamino)-2-methylpyridin-3-yl]amino]-3-methoxypyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CC=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(NCCO)N=C1C NQFFYUUJBUOFDJ-UHFFFAOYSA-N 0.000 claims 1
• RSSPXPXCXQDPLR-UHFFFAOYSA-N propan-2-yl 4-[2-[[6-(3-hydroxybutyl)-2-methoxypyridin-3-yl]amino]-3-methoxypyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound COC1=NC(CCC(C)O)=CC=C1NC1=NC=CC(OC2CCN(CC2)C(=O)OC(C)C)=C1OC RSSPXPXCXQDPLR-UHFFFAOYSA-N 0.000 claims 1
• RIFNEWHUCFYBII-UHFFFAOYSA-N propan-2-yl 4-[2-[[6-(3-hydroxypropyl)-2-methylpyridin-3-yl]amino]-3-methoxypyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CC=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(CCCO)N=C1C RIFNEWHUCFYBII-UHFFFAOYSA-N 0.000 claims 1
• HJZRHYQDPKMYOS-UHFFFAOYSA-N propan-2-yl 4-[3-ethoxy-2-(2-methoxy-4-methylsulfonylanilino)pyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=CN=C(NC=2C(=CC(=CC=2)S(C)(=O)=O)OC)C(OCC)=C1OC1CCN(C(=O)OC(C)C)CC1 HJZRHYQDPKMYOS-UHFFFAOYSA-N 0.000 claims 1
• UXRCHLREWYIIDR-UHFFFAOYSA-N propan-2-yl 4-[3-ethoxy-2-[2-fluoro-4-(2-phosphonooxyethyl)anilino]pyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=CN=C(NC=2C(=CC(CCOP(O)(O)=O)=CC=2)F)C(OCC)=C1OC1CCN(C(=O)OC(C)C)CC1 UXRCHLREWYIIDR-UHFFFAOYSA-N 0.000 claims 1
• BQZVPWQKSDXLMF-UHFFFAOYSA-N propan-2-yl 4-[3-ethynoxy-2-(2-fluoro-4-methylsulfonylanilino)pyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1OC1=CC=NC(NC=2C(=CC(=CC=2)S(C)(=O)=O)F)=C1OC#C BQZVPWQKSDXLMF-UHFFFAOYSA-N 0.000 claims 1
• RORQBCKAEAOPME-UHFFFAOYSA-N propan-2-yl 4-[3-methoxy-2-(2-methoxy-4-sulfamoylanilino)pyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound COC1=CC(S(N)(=O)=O)=CC=C1NC1=NC=CC(OC2CCN(CC2)C(=O)OC(C)C)=C1OC RORQBCKAEAOPME-UHFFFAOYSA-N 0.000 claims 1
• ZHEZIIBNJVTFPZ-UHFFFAOYSA-N propan-2-yl 4-[3-methoxy-2-[[2-methyl-6-(2-methylsulfonylethylamino)pyridin-3-yl]amino]pyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=CN=C(NC=2C(=NC(NCCS(C)(=O)=O)=CC=2)C)C(OC)=C1OC1CCN(C(=O)OC(C)C)CC1 ZHEZIIBNJVTFPZ-UHFFFAOYSA-N 0.000 claims 1
• PRQVPUFMBXFSLY-UHFFFAOYSA-N propan-2-yl 4-[3-methoxy-2-[[2-methyl-6-(2-phosphonooxyethyl)pyridin-3-yl]amino]pyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CC=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(CCOP(O)(O)=O)N=C1C PRQVPUFMBXFSLY-UHFFFAOYSA-N 0.000 claims 1
• UQZOLHXALBIHLH-UHFFFAOYSA-N propan-2-yl 4-[3-methoxy-2-[[2-methyl-6-(3-methylsulfonylazetidin-1-yl)pyridin-3-yl]amino]pyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=CN=C(NC=2C(=NC(=CC=2)N2CC(C2)S(C)(=O)=O)C)C(OC)=C1OC1CCN(C(=O)OC(C)C)CC1 UQZOLHXALBIHLH-UHFFFAOYSA-N 0.000 claims 1
• LTRZQCLFNCHXCN-UHFFFAOYSA-N propan-2-yl 4-[3-methoxy-2-[[2-methyl-6-(3-methylsulfonylpyrrolidin-1-yl)pyridin-3-yl]amino]pyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=CN=C(NC=2C(=NC(=CC=2)N2CC(CC2)S(C)(=O)=O)C)C(OC)=C1OC1CCN(C(=O)OC(C)C)CC1 LTRZQCLFNCHXCN-UHFFFAOYSA-N 0.000 claims 1
• BIQILRSITQOMBX-UHFFFAOYSA-N propan-2-yl 4-[3-methoxy-2-[[2-methyl-6-(3-phosphonooxypropoxy)pyridin-3-yl]amino]pyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CC=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(OCCCOP(O)(O)=O)N=C1C BIQILRSITQOMBX-UHFFFAOYSA-N 0.000 claims 1
• OVHHEDXKLOXWIK-UHFFFAOYSA-N propan-2-yl 4-[3-methoxy-2-[[2-methyl-6-[methyl(2-methylsulfonylethyl)amino]pyridin-3-yl]amino]pyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=CN=C(NC=2C(=NC(=CC=2)N(C)CCS(C)(=O)=O)C)C(OC)=C1OC1CCN(C(=O)OC(C)C)CC1 OVHHEDXKLOXWIK-UHFFFAOYSA-N 0.000 claims 1
• APWQZAPNNAEDMQ-UHFFFAOYSA-N propan-2-yl 4-[5-ethoxy-6-[(2-methyl-6-methylsulfonylpyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OCC)=C1NC1=CC=C(S(C)(=O)=O)N=C1C APWQZAPNNAEDMQ-UHFFFAOYSA-N 0.000 claims 1
• FCQXQDDLSGFNLC-UHFFFAOYSA-N propan-2-yl 4-[5-fluoro-2-(2-fluoro-4-methylsulfonylanilino)-3-methoxypyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CC(F)=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(S(C)(=O)=O)C=C1F FCQXQDDLSGFNLC-UHFFFAOYSA-N 0.000 claims 1
• RYEXGNAIMKHPSM-UHFFFAOYSA-N propan-2-yl 4-[5-fluoro-2-[[6-(2-hydroxyethoxy)-2-methylpyridin-3-yl]amino]-3-methoxypyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CC(F)=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(OCCO)N=C1C RYEXGNAIMKHPSM-UHFFFAOYSA-N 0.000 claims 1
• QAKVOLNWVHWBRW-UHFFFAOYSA-N propan-2-yl 4-[5-methoxy-6-[[2-methoxy-6-(2-methylsulfonylethylamino)pyridin-3-yl]amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound COC1=NC(NCCS(C)(=O)=O)=CC=C1NC1=NC=NC(OC2CCN(CC2)C(=O)OC(C)C)=C1OC QAKVOLNWVHWBRW-UHFFFAOYSA-N 0.000 claims 1
• ISYCRXQAHKXMSF-UHFFFAOYSA-N propan-2-yl 4-[5-methoxy-6-[[2-methyl-6-(2-methylsulfonylethoxy)pyridin-3-yl]amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(OCCS(C)(=O)=O)N=C1C ISYCRXQAHKXMSF-UHFFFAOYSA-N 0.000 claims 1
• LIVAQPZPEFSSGN-UHFFFAOYSA-N propan-2-yl 4-[5-methoxy-6-[[2-methyl-6-(2-methylsulfonylpropylamino)pyridin-3-yl]amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(NCC(C)S(C)(=O)=O)N=C1C LIVAQPZPEFSSGN-UHFFFAOYSA-N 0.000 claims 1
• QUOZILNVPDNUDG-UHFFFAOYSA-N propan-2-yl 4-[5-methoxy-6-[[2-methyl-6-(3-phosphonooxypropoxy)pyridin-3-yl]amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(OCCCOP(O)(O)=O)N=C1C QUOZILNVPDNUDG-UHFFFAOYSA-N 0.000 claims 1
• YMUICTMDTRKVAK-UHFFFAOYSA-N propan-2-yl 4-[5-methoxy-6-[[2-methyl-6-(3-phosphonooxypropyl)pyridin-3-yl]amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(CCCOP(O)(O)=O)N=C1C YMUICTMDTRKVAK-UHFFFAOYSA-N 0.000 claims 1
• FWQOUXNRLTZHFO-UHFFFAOYSA-N propan-2-yl 4-[5-methoxy-6-[[6-(2-methoxyethyl)-2-methylpyridin-3-yl]amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound CC1=NC(CCOC)=CC=C1NC1=NC=NC(OC2CCN(CC2)C(=O)OC(C)C)=C1OC FWQOUXNRLTZHFO-UHFFFAOYSA-N 0.000 claims 1
• DFBLEIOADQBDEI-UHFFFAOYSA-N propan-2-yl 4-[5-methoxy-6-[[6-(2-methylsulfonylethylamino)pyridin-3-yl]amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(NCCS(C)(=O)=O)N=C1 DFBLEIOADQBDEI-UHFFFAOYSA-N 0.000 claims 1
• BKSQZPVFLTVZJG-UHFFFAOYSA-N propan-2-yl 4-[6-(2-fluoro-4-methylsulfonylanilino)-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(S(C)(=O)=O)C=C1F BKSQZPVFLTVZJG-UHFFFAOYSA-N 0.000 claims 1
• GQPSJNBXSRFSPK-UHFFFAOYSA-N propan-2-yl 4-[6-[2-fluoro-4-(2-hydroxyethylsulfanyl)anilino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(SCCO)C=C1F GQPSJNBXSRFSPK-UHFFFAOYSA-N 0.000 claims 1
• ZAKZNAHPDRFZFM-UHFFFAOYSA-N propan-2-yl 4-[6-[2-fluoro-4-[2-(2-hydroxyethylamino)-2-oxoethyl]anilino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(CC(=O)NCCO)C=C1F ZAKZNAHPDRFZFM-UHFFFAOYSA-N 0.000 claims 1
• KGNQERURYAHRQR-UHFFFAOYSA-N propan-2-yl 4-[6-[[6-(2,3-dihydroxypropylamino)-2-methylpyridin-3-yl]amino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(NCC(O)CO)N=C1C KGNQERURYAHRQR-UHFFFAOYSA-N 0.000 claims 1
• TXASOKBKHAJZRB-UHFFFAOYSA-N propan-2-yl 4-[6-[[6-(2-hydroxyethoxy)-2-methylpyridin-3-yl]amino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(OCCO)N=C1C TXASOKBKHAJZRB-UHFFFAOYSA-N 0.000 claims 1
• WVVQFOPXEZJNIZ-UHFFFAOYSA-N propan-2-yl 4-[6-[[6-(2-hydroxypropylamino)-2-methylpyridin-3-yl]amino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(NCC(C)O)N=C1C WVVQFOPXEZJNIZ-UHFFFAOYSA-N 0.000 claims 1
• YROGJKWYERNZNM-UHFFFAOYSA-N propan-2-yl 4-[6-[[6-(3-hydroxypropyl)-2-methylpyridin-3-yl]amino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(CCCO)N=C1C YROGJKWYERNZNM-UHFFFAOYSA-N 0.000 claims 1
• FVBFTBKDDQIIOG-UHFFFAOYSA-N propan-2-yl 4-[6-[[6-(hydroxymethyl)-4-methylpyridin-3-yl]amino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CN=C(CO)C=C1C FVBFTBKDDQIIOG-UHFFFAOYSA-N 0.000 claims 1
• MCTXGCJJOUDCHS-UHFFFAOYSA-N propan-2-yl 4-[6-[[6-[2-(dimethylamino)-2-oxoethyl]-2-methylpyridin-3-yl]amino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(CC(=O)N(C)C)N=C1C MCTXGCJJOUDCHS-UHFFFAOYSA-N 0.000 claims 1
• 238000002360 preparation method Methods 0.000 description 123
• 239000000203 mixture Substances 0.000 description 113
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 111
• 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 description 103
• 102000005962 receptors Human genes 0.000 description 79
• 108020003175 receptors Proteins 0.000 description 79
• 239000000243 solution Substances 0.000 description 74
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
• 239000007787 solid Substances 0.000 description 57
• 210000004027 cell Anatomy 0.000 description 55
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 54
• 229940125396 insulin Drugs 0.000 description 50
• 102000004877 Insulin Human genes 0.000 description 49
• 108090001061 Insulin Proteins 0.000 description 49
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
• 238000006243 chemical reaction Methods 0.000 description 43
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 36
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 35
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
• 206010012601 diabetes mellitus Diseases 0.000 description 34
• 239000003112 inhibitor Substances 0.000 description 34
• 239000000543 intermediate Substances 0.000 description 34
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
• 235000019439 ethyl acetate Nutrition 0.000 description 33
• 201000010099 disease Diseases 0.000 description 32
• 239000012074 organic phase Substances 0.000 description 32
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
• 238000003556 assay Methods 0.000 description 30
• 238000004128 high performance liquid chromatography Methods 0.000 description 30
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 28
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
• 241000124008 Mammalia Species 0.000 description 27
• 239000008177 pharmaceutical agent Substances 0.000 description 27
• 208000008589 Obesity Diseases 0.000 description 25
• 239000012528 membrane Substances 0.000 description 25
• 239000000047 product Substances 0.000 description 25
• 235000020824 obesity Nutrition 0.000 description 24
• 238000009739 binding Methods 0.000 description 23
• 230000000694 effects Effects 0.000 description 23
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
• 230000027455 binding Effects 0.000 description 22
• 230000015572 biosynthetic process Effects 0.000 description 21
• 239000002904 solvent Substances 0.000 description 21
• 239000003446 ligand Substances 0.000 description 20
• 239000003921 oil Substances 0.000 description 20
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 20
• 210000004369 blood Anatomy 0.000 description 19
• 239000008280 blood Substances 0.000 description 19
• 238000003786 synthesis reaction Methods 0.000 description 19
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
• 239000002585 base Substances 0.000 description 18
• NVMHDJQDTCMXLH-UHFFFAOYSA-N propan-2-yl piperidine-1-carboxylate Chemical compound CC(C)OC(=O)N1CCCCC1 NVMHDJQDTCMXLH-UHFFFAOYSA-N 0.000 description 18
• 230000004044 response Effects 0.000 description 18
• 238000012360 testing method Methods 0.000 description 18
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 17
• 239000004480 active ingredient Substances 0.000 description 17
• 238000004440 column chromatography Methods 0.000 description 17
• 210000001519 tissue Anatomy 0.000 description 17
• 229940079593 drug Drugs 0.000 description 16
• 239000000843 powder Substances 0.000 description 16
• 238000003756 stirring Methods 0.000 description 16
• 241000700159 Rattus Species 0.000 description 15
• 230000003914 insulin secretion Effects 0.000 description 15
• 239000007788 liquid Substances 0.000 description 15
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
• 239000000725 suspension Substances 0.000 description 14
• 239000003826 tablet Substances 0.000 description 14
• 230000001771 impaired effect Effects 0.000 description 13
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 13
• 108090000623 proteins and genes Proteins 0.000 description 13
• 239000000126 substance Substances 0.000 description 13
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
• 239000012267 brine Substances 0.000 description 12
• 239000002775 capsule Substances 0.000 description 12
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 12
• ZSTVVHDPLQWOHI-UHFFFAOYSA-N propan-2-yl 4-(6-chloro-5-methoxypyrimidin-4-yl)oxypiperidine-1-carboxylate Chemical compound COC1=C(Cl)N=CN=C1OC1CCN(C(=O)OC(C)C)CC1 ZSTVVHDPLQWOHI-UHFFFAOYSA-N 0.000 description 12
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
• 239000011701 zinc Substances 0.000 description 12
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
• 238000007792 addition Methods 0.000 description 11
• 239000000872 buffer Substances 0.000 description 11
• 230000001965 increasing effect Effects 0.000 description 11
• 102000004169 proteins and genes Human genes 0.000 description 11
• 238000006467 substitution reaction Methods 0.000 description 11
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
• 229940100389 Sulfonylurea Drugs 0.000 description 10
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 10
• 125000003118 aryl group Chemical group 0.000 description 10
• 238000010790 dilution Methods 0.000 description 10
• 239000012895 dilution Substances 0.000 description 10
• 238000009472 formulation Methods 0.000 description 10
• 239000001963 growth medium Substances 0.000 description 10
• 150000003840 hydrochlorides Chemical class 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• 235000018102 proteins Nutrition 0.000 description 10
• 238000010992 reflux Methods 0.000 description 10
• 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 description 9
• 208000002705 Glucose Intolerance Diseases 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 239000002253 acid Substances 0.000 description 9
• 238000004458 analytical method Methods 0.000 description 9
• 210000003719 b-lymphocyte Anatomy 0.000 description 9
• 239000002299 complementary DNA Substances 0.000 description 9
• 208000029078 coronary artery disease Diseases 0.000 description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
• 210000000496 pancreas Anatomy 0.000 description 9
• 201000009104 prediabetes syndrome Diseases 0.000 description 9
• 238000003757 reverse transcription PCR Methods 0.000 description 9
• 239000011734 sodium Substances 0.000 description 9
• 230000002792 vascular Effects 0.000 description 9
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 8
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• 229940125753 fibrate Drugs 0.000 description 8
• 230000003834 intracellular effect Effects 0.000 description 8
• 210000004153 islets of langerhan Anatomy 0.000 description 8
• 239000000523 sample Substances 0.000 description 8
• 230000000638 stimulation Effects 0.000 description 8
• 239000006228 supernatant Substances 0.000 description 8
• SWLAMJPTOQZTAE-UHFFFAOYSA-N 4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]benzoic acid Chemical class COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C(O)=O)C=C1 SWLAMJPTOQZTAE-UHFFFAOYSA-N 0.000 description 7
• 229940123208 Biguanide Drugs 0.000 description 7
• 108010067722 Dipeptidyl Peptidase 4 Proteins 0.000 description 7
• 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 description 7
• 206010033307 Overweight Diseases 0.000 description 7
• 239000002333 angiotensin II receptor antagonist Substances 0.000 description 7
• 239000000883 anti-obesity agent Substances 0.000 description 7
• 229940125710 antiobesity agent Drugs 0.000 description 7
• 150000004283 biguanides Chemical class 0.000 description 7
• 239000012148 binding buffer Substances 0.000 description 7
• 239000002552 dosage form Substances 0.000 description 7
• 230000002401 inhibitory effect Effects 0.000 description 7
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
• 235000019341 magnesium sulphate Nutrition 0.000 description 7
• 229950004994 meglitinide Drugs 0.000 description 7
• 229910052763 palladium Inorganic materials 0.000 description 7
• GEBSTOFBXOTNGG-UHFFFAOYSA-N propan-2-yl 4-[6-[[6-(2-hydroxyethylsulfanyl)-2-methylpyridin-3-yl]amino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(SCCO)N=C1C GEBSTOFBXOTNGG-UHFFFAOYSA-N 0.000 description 7
• 239000003981 vehicle Substances 0.000 description 7
• 239000005541 ACE inhibitor Substances 0.000 description 6
• 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 6
• 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 6
• 206010019280 Heart failures Diseases 0.000 description 6
• 206010020772 Hypertension Diseases 0.000 description 6
• 241000699670 Mus sp. Species 0.000 description 6
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
• YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 6
• 125000004429 atom Chemical group 0.000 description 6
• 125000003636 chemical group Chemical group 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• 238000002648 combination therapy Methods 0.000 description 6
• 230000001276 controlling effect Effects 0.000 description 6
• 230000000875 corresponding effect Effects 0.000 description 6
• 238000011161 development Methods 0.000 description 6
• 230000018109 developmental process Effects 0.000 description 6
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 6
• 210000003574 melanophore Anatomy 0.000 description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
• 208000010125 myocardial infarction Diseases 0.000 description 6
• 239000012044 organic layer Substances 0.000 description 6
• 239000003614 peroxisome proliferator Substances 0.000 description 6
• 239000002243 precursor Substances 0.000 description 6
• 238000000746 purification Methods 0.000 description 6
• 150000003230 pyrimidines Chemical class 0.000 description 6
• 208000037803 restenosis Diseases 0.000 description 6
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 6
• 239000000741 silica gel Substances 0.000 description 6
• 229910002027 silica gel Inorganic materials 0.000 description 6
• 239000000375 suspending agent Substances 0.000 description 6
• 238000010189 synthetic method Methods 0.000 description 6
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
• 229910052722 tritium Inorganic materials 0.000 description 6
• 241001430294 unidentified retrovirus Species 0.000 description 6
• YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 5
• CIIMDJCZOSHNGB-UHFFFAOYSA-N 2-(6-methyl-5-nitropyridin-2-yl)sulfanylethanol Chemical compound CC1=NC(SCCO)=CC=C1[N+]([O-])=O CIIMDJCZOSHNGB-UHFFFAOYSA-N 0.000 description 5
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 5
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
• 241000283973 Oryctolagus cuniculus Species 0.000 description 5
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
• BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 5
• 238000010521 absorption reaction Methods 0.000 description 5
• 150000001412 amines Chemical class 0.000 description 5
• 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 5
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
• 239000005557 antagonist Substances 0.000 description 5
• 239000002830 appetite depressant Substances 0.000 description 5
• 230000008901 benefit Effects 0.000 description 5
• 239000000969 carrier Substances 0.000 description 5
• 238000001816 cooling Methods 0.000 description 5
• 238000001514 detection method Methods 0.000 description 5
• 239000002270 dispersing agent Substances 0.000 description 5
• 239000006185 dispersion Substances 0.000 description 5
• PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 5
• 239000000839 emulsion Substances 0.000 description 5
• 238000000338 in vitro Methods 0.000 description 5
• 230000005764 inhibitory process Effects 0.000 description 5
• 229910052740 iodine Inorganic materials 0.000 description 5
• 208000017169 kidney disease Diseases 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 5
• 229910052757 nitrogen Inorganic materials 0.000 description 5
• 230000009871 nonspecific binding Effects 0.000 description 5
• AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 5
• 229960001243 orlistat Drugs 0.000 description 5
• 230000007170 pathology Effects 0.000 description 5
• 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 5
• 229910000027 potassium carbonate Inorganic materials 0.000 description 5
• 235000011181 potassium carbonates Nutrition 0.000 description 5
• 239000000651 prodrug Substances 0.000 description 5
• 229940002612 prodrug Drugs 0.000 description 5
• 238000011321 prophylaxis Methods 0.000 description 5
• 125000006239 protecting group Chemical group 0.000 description 5
• 150000003254 radicals Chemical class 0.000 description 5
• 230000009467 reduction Effects 0.000 description 5
• 238000006722 reduction reaction Methods 0.000 description 5
• 230000002829 reductive effect Effects 0.000 description 5
• 239000011780 sodium chloride Substances 0.000 description 5
• 229910000104 sodium hydride Inorganic materials 0.000 description 5
• 239000007921 spray Substances 0.000 description 5
• 229940031439 squalene Drugs 0.000 description 5
• TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 5
• WOQWWNJQZLYLMC-UHFFFAOYSA-N 2,5-difluoro-4-nitrophenol Chemical compound OC1=CC(F)=C([N+]([O-])=O)C=C1F WOQWWNJQZLYLMC-UHFFFAOYSA-N 0.000 description 4
• PNAYGNCLPYBJAL-UHFFFAOYSA-N 2-[[4-chloro-6-(2,3-dimethylanilino)pyrimidin-2-yl]amino]acetic acid Chemical compound CC1=CC=CC(NC=2N=C(NCC(O)=O)N=C(Cl)C=2)=C1C PNAYGNCLPYBJAL-UHFFFAOYSA-N 0.000 description 4
• LJNLOXQPMZAWIX-UHFFFAOYSA-N 2-chloro-3-methoxy-4-nitropyridine Chemical compound COC1=C(Cl)N=CC=C1[N+]([O-])=O LJNLOXQPMZAWIX-UHFFFAOYSA-N 0.000 description 4
• WFHPXSHLCFHEIA-UHFFFAOYSA-N 4,6,11-tris(2-methylpropyl)-1,4,6,11-tetraza-5-phosphabicyclo[3.3.3]undecane Chemical compound C1CN(CC(C)C)P2N(CC(C)C)CCN1CCN2CC(C)C WFHPXSHLCFHEIA-UHFFFAOYSA-N 0.000 description 4
• 201000001320 Atherosclerosis Diseases 0.000 description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
• 206010007559 Cardiac failure congestive Diseases 0.000 description 4
• 208000002177 Cataract Diseases 0.000 description 4
• 108020004635 Complementary DNA Proteins 0.000 description 4
• 108020004414 DNA Proteins 0.000 description 4
• OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 description 4
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
• 108010010803 Gelatin Proteins 0.000 description 4
• HEMJJKBWTPKOJG-UHFFFAOYSA-N Gemfibrozil Chemical compound CC1=CC=C(C)C(OCCCC(C)(C)C(O)=O)=C1 HEMJJKBWTPKOJG-UHFFFAOYSA-N 0.000 description 4
• 206010060378 Hyperinsulinaemia Diseases 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
• 239000005089 Luciferase Substances 0.000 description 4
• 208000035180 MODY Diseases 0.000 description 4
• 208000001145 Metabolic Syndrome Diseases 0.000 description 4
• GULNIHOSWFYMRN-UHFFFAOYSA-N N'-[(4-methoxyphenyl)methyl]-N,N-dimethyl-N'-(2-pyrimidinyl)ethane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=NC=CC=N1 GULNIHOSWFYMRN-UHFFFAOYSA-N 0.000 description 4
• DRBBFCLWYRJSJZ-UHFFFAOYSA-N N-phosphocreatine Chemical compound OC(=O)CN(C)C(=N)NP(O)(O)=O DRBBFCLWYRJSJZ-UHFFFAOYSA-N 0.000 description 4
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
• 238000010240 RT-PCR analysis Methods 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• 229920002472 Starch Polymers 0.000 description 4
• 208000006011 Stroke Diseases 0.000 description 4
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 4
• 230000005856 abnormality Effects 0.000 description 4
• 125000002252 acyl group Chemical group 0.000 description 4
• 239000000443 aerosol Substances 0.000 description 4
• 229910052783 alkali metal Inorganic materials 0.000 description 4
• 238000010171 animal model Methods 0.000 description 4
• 239000012131 assay buffer Substances 0.000 description 4
• 229960000516 bezafibrate Drugs 0.000 description 4
• IIBYAHWJQTYFKB-UHFFFAOYSA-N bezafibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 IIBYAHWJQTYFKB-UHFFFAOYSA-N 0.000 description 4
• 239000011230 binding agent Substances 0.000 description 4
• 230000037396 body weight Effects 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
• 239000011575 calcium Substances 0.000 description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
• 239000003054 catalyst Substances 0.000 description 4
• 229960001214 clofibrate Drugs 0.000 description 4
• KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 4
• 239000003086 colorant Substances 0.000 description 4
• 239000010949 copper Substances 0.000 description 4
• 238000010168 coupling process Methods 0.000 description 4
• 230000034994 death Effects 0.000 description 4
• 230000001419 dependent effect Effects 0.000 description 4
• 239000003085 diluting agent Substances 0.000 description 4
• CNXMDTWQWLGCPE-UHFFFAOYSA-N ditert-butyl-(2-phenylphenyl)phosphane Chemical compound CC(C)(C)P(C(C)(C)C)C1=CC=CC=C1C1=CC=CC=C1 CNXMDTWQWLGCPE-UHFFFAOYSA-N 0.000 description 4
• 239000013613 expression plasmid Substances 0.000 description 4
• 235000019197 fats Nutrition 0.000 description 4
• 229960002297 fenofibrate Drugs 0.000 description 4
• YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 description 4
• 239000000706 filtrate Substances 0.000 description 4
• 238000001914 filtration Methods 0.000 description 4
• 230000006870 function Effects 0.000 description 4
• 229920000159 gelatin Polymers 0.000 description 4
• 235000019322 gelatine Nutrition 0.000 description 4
• 235000011852 gelatine desserts Nutrition 0.000 description 4
• 229960003627 gemfibrozil Drugs 0.000 description 4
• 230000004153 glucose metabolism Effects 0.000 description 4
• 230000003451 hyperinsulinaemic effect Effects 0.000 description 4
• 201000008980 hyperinsulinism Diseases 0.000 description 4
• 239000005457 ice water Substances 0.000 description 4
• 238000001727 in vivo Methods 0.000 description 4
• 238000011534 incubation Methods 0.000 description 4
• 238000002347 injection Methods 0.000 description 4
• 239000007924 injection Substances 0.000 description 4
• 125000002346 iodo group Chemical group I* 0.000 description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
• 208000001921 latent autoimmune diabetes in adults Diseases 0.000 description 4
• 239000007937 lozenge Substances 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• 201000006950 maturity-onset diabetes of the young Diseases 0.000 description 4
• 231100000252 nontoxic Toxicity 0.000 description 4
• 230000003000 nontoxic effect Effects 0.000 description 4
• 239000008188 pellet Substances 0.000 description 4
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
• 230000000291 postprandial effect Effects 0.000 description 4
• 239000003755 preservative agent Substances 0.000 description 4
• 108090000765 processed proteins & peptides Proteins 0.000 description 4
• 239000012557 regeneration buffer Substances 0.000 description 4
• 230000028327 secretion Effects 0.000 description 4
• 229960004425 sibutramine Drugs 0.000 description 4
• UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 4
• 239000003381 stabilizer Substances 0.000 description 4
• 230000000087 stabilizing effect Effects 0.000 description 4
• 239000008107 starch Substances 0.000 description 4
• 235000019698 starch Nutrition 0.000 description 4
• 235000000346 sugar Nutrition 0.000 description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
• 150000003512 tertiary amines Chemical class 0.000 description 4
• 239000002562 thickening agent Substances 0.000 description 4
• 238000004809 thin layer chromatography Methods 0.000 description 4
• 229910052725 zinc Inorganic materials 0.000 description 4
• DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 4
• DCKIZMRDMKCGNI-UHFFFAOYSA-N (4-methyl-5-nitropyridin-2-yl)methanol Chemical compound CC1=CC(CO)=NC=C1[N+]([O-])=O DCKIZMRDMKCGNI-UHFFFAOYSA-N 0.000 description 3
• KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 3
• WYUIHXOCVSQXOX-UHFFFAOYSA-N 1-ethoxy-2,5-difluoro-4-nitrobenzene Chemical compound CCOC1=CC(F)=C([N+]([O-])=O)C=C1F WYUIHXOCVSQXOX-UHFFFAOYSA-N 0.000 description 3
• VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 3
• UWEVMHYTZHHEJG-UHFFFAOYSA-N 2-chloro-4-nitropyridin-3-ol Chemical compound OC1=C(Cl)N=CC=C1[N+]([O-])=O UWEVMHYTZHHEJG-UHFFFAOYSA-N 0.000 description 3
• UFMCZYUTXQRFKR-UHFFFAOYSA-N 2-methyl-6-methylsulfonylpyridin-3-amine Chemical compound CC1=NC(S(C)(=O)=O)=CC=C1N UFMCZYUTXQRFKR-UHFFFAOYSA-N 0.000 description 3
• PLCPELCHGBGDTF-UHFFFAOYSA-N 2-methyl-6-propylsulfanylpyridin-3-amine Chemical compound CCCSC1=CC=C(N)C(C)=N1 PLCPELCHGBGDTF-UHFFFAOYSA-N 0.000 description 3
• MPMKMQHJHDHPBE-RUZDIDTESA-N 4-[[(2r)-1-(1-benzothiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-[(3-chlorophenyl)methyl]amino]butanoic acid Chemical compound O=C([C@@]1(N(CC1)C(=O)C=1C2=CC=CC=C2SC=1)C)N(CCCC(O)=O)CC1=CC=CC(Cl)=C1 MPMKMQHJHDHPBE-RUZDIDTESA-N 0.000 description 3
• PLGUZQAFKLZXPW-UHFFFAOYSA-N 4-ethoxy-2,5-difluoroaniline Chemical compound CCOC1=CC(F)=C(N)C=C1F PLGUZQAFKLZXPW-UHFFFAOYSA-N 0.000 description 3
• YSDZRLVHRVMNBK-UHFFFAOYSA-N 6-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-methylpyridin-3-amine Chemical compound C1=C(N)C(C)=CC(CO[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C(C)(C)C)=N1 YSDZRLVHRVMNBK-UHFFFAOYSA-N 0.000 description 3
• FLDDNTAAWZHAOT-UHFFFAOYSA-N 6-bromo-2,4-dimethylpyridin-3-amine Chemical compound CC1=CC(Br)=NC(C)=C1N FLDDNTAAWZHAOT-UHFFFAOYSA-N 0.000 description 3
• JVLRFRZVCOWBDY-UHFFFAOYSA-N 6-fluoro-2-methyl-3-nitropyridine Chemical compound CC1=NC(F)=CC=C1[N+]([O-])=O JVLRFRZVCOWBDY-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• 208000010444 Acidosis Diseases 0.000 description 3
• 102000011690 Adiponectin Human genes 0.000 description 3
• 108010076365 Adiponectin Proteins 0.000 description 3
• 206010002383 Angina Pectoris Diseases 0.000 description 3
• BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 3
• 239000005552 B01AC04 - Clopidogrel Substances 0.000 description 3
• 239000005528 B01AC05 - Ticlopidine Substances 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
• 238000009010 Bradford assay Methods 0.000 description 3
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
• 208000024172 Cardiovascular disease Diseases 0.000 description 3
• 229920001268 Cholestyramine Polymers 0.000 description 3
• 229920002911 Colestipol Polymers 0.000 description 3
• 206010009900 Colitis ulcerative Diseases 0.000 description 3
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 3
• 208000007342 Diabetic Nephropathies Diseases 0.000 description 3
• 208000032131 Diabetic Neuropathies Diseases 0.000 description 3
• 206010012689 Diabetic retinopathy Diseases 0.000 description 3
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
• 206010048554 Endothelial dysfunction Diseases 0.000 description 3
• 241000283074 Equus asinus Species 0.000 description 3
• 208000010228 Erectile Dysfunction Diseases 0.000 description 3
• 241000282412 Homo Species 0.000 description 3
• 206010022562 Intermittent claudication Diseases 0.000 description 3
• 208000032382 Ischaemic stroke Diseases 0.000 description 3
• 208000007976 Ketosis Diseases 0.000 description 3
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
• 208000007177 Left Ventricular Hypertrophy Diseases 0.000 description 3
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 3
• 240000007472 Leucaena leucocephala Species 0.000 description 3
• 108060001084 Luciferase Proteins 0.000 description 3
• YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 description 3
• 206010027417 Metabolic acidosis Diseases 0.000 description 3
• 241000699666 Mus <mouse, genus> Species 0.000 description 3
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
• 238000005481 NMR spectroscopy Methods 0.000 description 3
• 206010028851 Necrosis Diseases 0.000 description 3
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 3
• 208000001132 Osteoporosis Diseases 0.000 description 3
• 208000005764 Peripheral Arterial Disease Diseases 0.000 description 3
• 208000030831 Peripheral arterial occlusive disease Diseases 0.000 description 3
• 208000018262 Peripheral vascular disease Diseases 0.000 description 3
• 206010036618 Premenstrual syndrome Diseases 0.000 description 3
• 241000283984 Rodentia Species 0.000 description 3
• 208000007536 Thrombosis Diseases 0.000 description 3
• 208000032109 Transient ischaemic attack Diseases 0.000 description 3
• 208000025865 Ulcer Diseases 0.000 description 3
• 201000006704 Ulcerative Colitis Diseases 0.000 description 3
• 238000002835 absorbance Methods 0.000 description 3
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
• 229960001138 acetylsalicylic acid Drugs 0.000 description 3
• 239000008186 active pharmaceutical agent Substances 0.000 description 3
• 239000000654 additive Substances 0.000 description 3
• 150000001299 aldehydes Chemical group 0.000 description 3
• 229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
• 150000008041 alkali metal carbonates Chemical class 0.000 description 3
• 238000002399 angioplasty Methods 0.000 description 3
• 229940125709 anorectic agent Drugs 0.000 description 3
• 230000000890 antigenic effect Effects 0.000 description 3
• 229940127218 antiplatelet drug Drugs 0.000 description 3
• 230000006907 apoptotic process Effects 0.000 description 3
• 238000013459 approach Methods 0.000 description 3
• 206010003246 arthritis Diseases 0.000 description 3
• 230000009286 beneficial effect Effects 0.000 description 3
• 229920000080 bile acid sequestrant Polymers 0.000 description 3
• 229940096699 bile acid sequestrants Drugs 0.000 description 3
• QWCRAEMEVRGPNT-UHFFFAOYSA-N buspirone Chemical compound C1C(=O)N(CCCCN2CCN(CC2)C=2N=CC=CN=2)C(=O)CC21CCCC2 QWCRAEMEVRGPNT-UHFFFAOYSA-N 0.000 description 3
• 229910002091 carbon monoxide Inorganic materials 0.000 description 3
• 239000001768 carboxy methyl cellulose Substances 0.000 description 3
• 230000001413 cellular effect Effects 0.000 description 3
• 239000001913 cellulose Substances 0.000 description 3
• 229920002678 cellulose Polymers 0.000 description 3
• 125000001309 chloro group Chemical group Cl* 0.000 description 3
• 235000012000 cholesterol Nutrition 0.000 description 3
• 208000020832 chronic kidney disease Diseases 0.000 description 3
• 208000022831 chronic renal failure syndrome Diseases 0.000 description 3
• GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 description 3
• 229960003009 clopidogrel Drugs 0.000 description 3
• GMRWGQCZJGVHKL-UHFFFAOYSA-N colestipol Chemical compound ClCC1CO1.NCCNCCNCCNCCN GMRWGQCZJGVHKL-UHFFFAOYSA-N 0.000 description 3
• 229960002604 colestipol Drugs 0.000 description 3
• 239000012230 colorless oil Substances 0.000 description 3
• 229940125773 compound 10 Drugs 0.000 description 3
• 229940125877 compound 31 Drugs 0.000 description 3
• 208000018631 connective tissue disease Diseases 0.000 description 3
• 229910052802 copper Inorganic materials 0.000 description 3
• 230000008878 coupling Effects 0.000 description 3
• 238000005859 coupling reaction Methods 0.000 description 3
• 239000006071 cream Substances 0.000 description 3
• 238000010511 deprotection reaction Methods 0.000 description 3
• 229910052805 deuterium Inorganic materials 0.000 description 3
• 208000033679 diabetic kidney disease Diseases 0.000 description 3
• 235000014113 dietary fatty acids Nutrition 0.000 description 3
• 231100000673 dose–response relationship Toxicity 0.000 description 3
• 238000004520 electroporation Methods 0.000 description 3
• 230000008694 endothelial dysfunction Effects 0.000 description 3
• 239000003623 enhancer Substances 0.000 description 3
• GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 3
• 239000000194 fatty acid Substances 0.000 description 3
• 229930195729 fatty acid Natural products 0.000 description 3
• 239000000796 flavoring agent Substances 0.000 description 3
• 239000007789 gas Substances 0.000 description 3
• 239000000499 gel Substances 0.000 description 3
• 239000008273 gelatin Substances 0.000 description 3
• 206010061989 glomerulosclerosis Diseases 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• 229940088597 hormone Drugs 0.000 description 3
• 239000005556 hormone Substances 0.000 description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
• 210000003016 hypothalamus Anatomy 0.000 description 3
• 201000001881 impotence Diseases 0.000 description 3
• 239000012442 inert solvent Substances 0.000 description 3
• 239000004615 ingredient Substances 0.000 description 3
• 208000021156 intermittent vascular claudication Diseases 0.000 description 3
• 229940125425 inverse agonist Drugs 0.000 description 3
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
• ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 3
• 230000004140 ketosis Effects 0.000 description 3
• 210000003734 kidney Anatomy 0.000 description 3
• 239000008101 lactose Substances 0.000 description 3
• 230000000670 limiting effect Effects 0.000 description 3
• 229910052744 lithium Inorganic materials 0.000 description 3
• 210000004185 liver Anatomy 0.000 description 3
• 208000002780 macular degeneration Diseases 0.000 description 3
• 238000005259 measurement Methods 0.000 description 3
• 230000001404 mediated effect Effects 0.000 description 3
• 239000002609 medium Substances 0.000 description 3
• 229960003987 melatonin Drugs 0.000 description 3
• DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 description 3
• 238000002156 mixing Methods 0.000 description 3
• 230000017074 necrotic cell death Effects 0.000 description 3
• 229960003512 nicotinic acid Drugs 0.000 description 3
• 235000001968 nicotinic acid Nutrition 0.000 description 3
• 239000011664 nicotinic acid Substances 0.000 description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
• 239000004031 partial agonist Substances 0.000 description 3
• 230000002093 peripheral effect Effects 0.000 description 3
• 230000000144 pharmacologic effect Effects 0.000 description 3
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 3
• 239000000106 platelet aggregation inhibitor Substances 0.000 description 3
• 239000013641 positive control Substances 0.000 description 3
• 229910052700 potassium Inorganic materials 0.000 description 3
• 239000011591 potassium Substances 0.000 description 3
• 229960003975 potassium Drugs 0.000 description 3
• 230000002265 prevention Effects 0.000 description 3
• 230000008569 process Effects 0.000 description 3
• MNOCEOLXVAGXCV-UHFFFAOYSA-N propan-2-yl 4-[6-(4-ethoxy-2,5-difluoroanilino)-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=C(F)C(OCC)=CC(F)=C1NC1=NC=NC(OC2CCN(CC2)C(=O)OC(C)C)=C1OC MNOCEOLXVAGXCV-UHFFFAOYSA-N 0.000 description 3
• UOQOAOXEFHQDOJ-UHFFFAOYSA-N propan-2-yl 4-[6-[(6-bromo-2,4-dimethylpyridin-3-yl)amino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=C(C)C=C(Br)N=C1C UOQOAOXEFHQDOJ-UHFFFAOYSA-N 0.000 description 3
• GZFNQYRKXRUCFP-UHFFFAOYSA-N propan-2-yl 4-[6-[(6-bromo-2-methylpyridin-3-yl)-[(2-methylpropan-2-yl)oxycarbonyl]amino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(N(C(=O)OC(C)(C)C)C=2C(=NC(Br)=CC=2)C)C(OC)=C1OC1CCN(C(=O)OC(C)C)CC1 GZFNQYRKXRUCFP-UHFFFAOYSA-N 0.000 description 3
• OCEAUJZASITDQC-UHFFFAOYSA-N propan-2-yl 4-[6-[[6-(2-hydroxyethylamino)-2-methylpyridin-3-yl]amino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(NCCO)N=C1C OCEAUJZASITDQC-UHFFFAOYSA-N 0.000 description 3
• 239000000719 purinergic P2Y receptor antagonist Substances 0.000 description 3
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
• 239000002464 receptor antagonist Substances 0.000 description 3
• 229940044551 receptor antagonist Drugs 0.000 description 3
• 230000002441 reversible effect Effects 0.000 description 3
• 230000011664 signaling Effects 0.000 description 3
• 210000003491 skin Anatomy 0.000 description 3
• 208000017520 skin disease Diseases 0.000 description 3
• 229910000033 sodium borohydride Inorganic materials 0.000 description 3
• 239000012279 sodium borohydride Substances 0.000 description 3
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 3
• LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 3
• 238000010186 staining Methods 0.000 description 3
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
• 239000000829 suppository Substances 0.000 description 3
• PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 description 3
• 229960005001 ticlopidine Drugs 0.000 description 3
• 201000010875 transient cerebral ischemia Diseases 0.000 description 3
• ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 3
• 230000036269 ulceration Effects 0.000 description 3
• 239000013598 vector Substances 0.000 description 3
• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
• KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
• STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 2
• YVGKDKNNONDERG-UHFFFAOYSA-N (6-methyl-5-nitropyridin-2-yl)methanol Chemical compound CC1=NC(CO)=CC=C1[N+]([O-])=O YVGKDKNNONDERG-UHFFFAOYSA-N 0.000 description 2
• VGORQVUQDIRURX-UHFFFAOYSA-N (6-methyl-5-nitropyridin-2-yl)methyl methanesulfonate Chemical compound CC1=NC(COS(C)(=O)=O)=CC=C1[N+]([O-])=O VGORQVUQDIRURX-UHFFFAOYSA-N 0.000 description 2
• WOEPXUKZDOTUPD-UHFFFAOYSA-N 1,4-difluoro-2-nitro-5-propoxybenzene Chemical compound CCCOC1=CC(F)=C([N+]([O-])=O)C=C1F WOEPXUKZDOTUPD-UHFFFAOYSA-N 0.000 description 2
• DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 description 2
• UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 2
• FSYHJEBPLDNXAM-UHFFFAOYSA-N 2,4-dimethylpyridin-3-amine Chemical compound CC1=CC=NC(C)=C1N FSYHJEBPLDNXAM-UHFFFAOYSA-N 0.000 description 2
• WISXXOGOMDYNSN-UHFFFAOYSA-N 2,6-dimethylpyridin-3-amine Chemical compound CC1=CC=C(N)C(C)=N1 WISXXOGOMDYNSN-UHFFFAOYSA-N 0.000 description 2
• MZURIURWHQSBMR-UHFFFAOYSA-N 2-(5-aminopyridin-2-yl)sulfanylethanol Chemical compound NC1=CC=C(SCCO)N=C1 MZURIURWHQSBMR-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• ZXTUWQSKUFIVIH-UHFFFAOYSA-N 2-[5-[[5-methoxy-6-(1-propan-2-yloxycarbonylpiperidin-4-yl)oxypyrimidin-4-yl]amino]-6-methylpyridin-2-yl]acetic acid Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(CC(O)=O)N=C1C ZXTUWQSKUFIVIH-UHFFFAOYSA-N 0.000 description 2
• RSOPTYAZDFSMTN-UHFFFAOYSA-N 2-chloropyridin-3-ol Chemical compound OC1=CC=CN=C1Cl RSOPTYAZDFSMTN-UHFFFAOYSA-N 0.000 description 2
• IYFALRRQRHZZMJ-UHFFFAOYSA-N 2-fluoro-4-(2-methoxyethoxy)aniline Chemical compound COCCOC1=CC=C(N)C(F)=C1 IYFALRRQRHZZMJ-UHFFFAOYSA-N 0.000 description 2
• UGUIBNHHDIEZJI-UHFFFAOYSA-N 2-fluoro-4-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=C(N)C(F)=C1 UGUIBNHHDIEZJI-UHFFFAOYSA-N 0.000 description 2
• UFVQEVWFMDBSCC-UHFFFAOYSA-N 2-methyl-6-(2-methylsulfonylpropan-2-yl)pyridin-3-amine Chemical compound CC1=NC(C(C)(C)S(C)(=O)=O)=CC=C1N UFVQEVWFMDBSCC-UHFFFAOYSA-N 0.000 description 2
• JLGJPKACXFDTFD-UHFFFAOYSA-N 2-methyl-6-propan-2-ylsulfanylpyridin-3-amine Chemical compound CC(C)SC1=CC=C(N)C(C)=N1 JLGJPKACXFDTFD-UHFFFAOYSA-N 0.000 description 2
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
• GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
• IJQIGKLDBGKSNT-UHFFFAOYSA-N 4,6-dichloro-5-methoxypyrimidine Chemical compound COC1=C(Cl)N=CN=C1Cl IJQIGKLDBGKSNT-UHFFFAOYSA-N 0.000 description 2
• DUFGYCAXVIUXIP-UHFFFAOYSA-N 4,6-dihydroxypyrimidine Chemical compound OC1=CC(O)=NC=N1 DUFGYCAXVIUXIP-UHFFFAOYSA-N 0.000 description 2
• MZLUZUNCYWMYAM-UHFFFAOYSA-N 4-chloro-5-methoxy-6-piperidin-4-yloxypyrimidine Chemical compound COC1=C(Cl)N=CN=C1OC1CCNCC1 MZLUZUNCYWMYAM-UHFFFAOYSA-N 0.000 description 2
• BATZHWWYNGQYHC-UHFFFAOYSA-N 4-methyl-5-nitropyridine-2-carbonitrile Chemical compound CC1=CC(C#N)=NC=C1[N+]([O-])=O BATZHWWYNGQYHC-UHFFFAOYSA-N 0.000 description 2
• VKLKXFOZNHEBSW-UHFFFAOYSA-N 5-[[3-[(4-morpholin-4-ylbenzoyl)amino]phenyl]methoxy]pyridine-3-carboxamide Chemical compound O1CCN(CC1)C1=CC=C(C(=O)NC=2C=C(COC=3C=NC=C(C(=O)N)C=3)C=CC=2)C=C1 VKLKXFOZNHEBSW-UHFFFAOYSA-N 0.000 description 2
• VFFZWMWTUSXDCB-ZDUSSCGKSA-N 6-[2-[[2-[(2s)-2-cyanopyrrolidin-1-yl]-2-oxoethyl]amino]ethylamino]pyridine-3-carbonitrile Chemical compound N1([C@@H](CCC1)C#N)C(=O)CNCCNC1=CC=C(C#N)C=N1 VFFZWMWTUSXDCB-ZDUSSCGKSA-N 0.000 description 2
• WWZPFSKUDCVXJR-UHFFFAOYSA-N 6-[2-[tert-butyl(dimethyl)silyl]oxyethylsulfanyl]-2-methylpyridin-3-amine Chemical compound CC1=NC(SCCO[Si](C)(C)C(C)(C)C)=CC=C1N WWZPFSKUDCVXJR-UHFFFAOYSA-N 0.000 description 2
• LHBNXJJBGJDOCG-UHFFFAOYSA-N 6-ethylsulfanyl-2-methylpyridin-3-amine Chemical compound CCSC1=CC=C(N)C(C)=N1 LHBNXJJBGJDOCG-UHFFFAOYSA-N 0.000 description 2
• OFUQFEHUVYXKJI-UHFFFAOYSA-N 6-methyl-2-n-(2-methylsulfonylethyl)pyridine-2,5-diamine Chemical compound CC1=NC(NCCS(C)(=O)=O)=CC=C1N OFUQFEHUVYXKJI-UHFFFAOYSA-N 0.000 description 2
• NKZIEDOFORWCFI-UHFFFAOYSA-N 6-methyl-5-nitropyridine-2-carbaldehyde Chemical compound CC1=NC(C=O)=CC=C1[N+]([O-])=O NKZIEDOFORWCFI-UHFFFAOYSA-N 0.000 description 2
• XASOHFCUIQARJT-UHFFFAOYSA-N 8-methoxy-6-[7-(2-morpholin-4-ylethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C(N1C(=O)C2=C(OC)C=C(C=3N4C(=NC=3)C=C(C=C4)OCCN3CCOCC3)C=C2CC1)C(F)(F)F XASOHFCUIQARJT-UHFFFAOYSA-N 0.000 description 2
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
• 208000030090 Acute Disease Diseases 0.000 description 2
• ZKHQWZAMYRWXGA-KQYNXXCUSA-N Adenosine triphosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-N 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
• 101710177589 Asp/Glu-specific dipeptidyl-peptidase Proteins 0.000 description 2
• 241000416162 Astragalus gummifer Species 0.000 description 2
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
• 241000283690 Bos taurus Species 0.000 description 2
• 241000282472 Canis lupus familiaris Species 0.000 description 2
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• 208000017667 Chronic Disease Diseases 0.000 description 2
• 229920002261 Corn starch Polymers 0.000 description 2
• 206010052895 Coronary artery insufficiency Diseases 0.000 description 2
• 102000004420 Creatine Kinase Human genes 0.000 description 2
• 108010042126 Creatine kinase Proteins 0.000 description 2
• 241000699800 Cricetinae Species 0.000 description 2
• 101710095468 Cyclase Proteins 0.000 description 2
• SUZLHDUTVMZSEV-UHFFFAOYSA-N Deoxycoleonol Natural products C12C(=O)CC(C)(C=C)OC2(C)C(OC(=O)C)C(O)C2C1(C)C(O)CCC2(C)C SUZLHDUTVMZSEV-UHFFFAOYSA-N 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
• 102100036968 Dipeptidyl peptidase 8 Human genes 0.000 description 2
• 102100036969 Dipeptidyl peptidase 9 Human genes 0.000 description 2
• 102000004190 Enzymes Human genes 0.000 description 2
• 108090000790 Enzymes Proteins 0.000 description 2
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
• 241000206602 Eukaryota Species 0.000 description 2
• 241000282326 Felis catus Species 0.000 description 2
• PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 2
• 108010004460 Gastric Inhibitory Polypeptide Proteins 0.000 description 2
• 102000003638 Glucose-6-Phosphatase Human genes 0.000 description 2
• 108010086800 Glucose-6-Phosphatase Proteins 0.000 description 2
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
• 102000007390 Glycogen Phosphorylase Human genes 0.000 description 2
• 108010046163 Glycogen Phosphorylase Proteins 0.000 description 2
• NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
• 101000804947 Homo sapiens Dipeptidyl peptidase 8 Proteins 0.000 description 2
• 101000804945 Homo sapiens Dipeptidyl peptidase 9 Proteins 0.000 description 2
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
• 229940122199 Insulin secretagogue Drugs 0.000 description 2
• 102000016924 KATP Channels Human genes 0.000 description 2
• 108010053914 KATP Channels Proteins 0.000 description 2
• ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 2
• 229930182821 L-proline Natural products 0.000 description 2
• 102000007330 LDL Lipoproteins Human genes 0.000 description 2
• 102000016267 Leptin Human genes 0.000 description 2
• 108010092277 Leptin Proteins 0.000 description 2
• 108010013563 Lipoprotein Lipase Proteins 0.000 description 2
• 102100022119 Lipoprotein lipase Human genes 0.000 description 2
• 208000002720 Malnutrition Diseases 0.000 description 2
• 101710151321 Melanostatin Proteins 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• 102100031545 Microsomal triglyceride transfer protein large subunit Human genes 0.000 description 2
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
• ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
• 102400000064 Neuropeptide Y Human genes 0.000 description 2
• 101100241454 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) nuc-2 gene Proteins 0.000 description 2
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
• 108091034117 Oligonucleotide Proteins 0.000 description 2
• 108090000854 Oxidoreductases Proteins 0.000 description 2
• 102000004316 Oxidoreductases Human genes 0.000 description 2
• 229930040373 Paraformaldehyde Natural products 0.000 description 2
• 102000035195 Peptidases Human genes 0.000 description 2
• 108091005804 Peptidases Proteins 0.000 description 2
• 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 2
• 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 2
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
• 239000004743 Polypropylene Substances 0.000 description 2
• 101710178372 Prolyl endopeptidase Proteins 0.000 description 2
• 102100023832 Prolyl endopeptidase FAP Human genes 0.000 description 2
• 101710129873 Prolyl endopeptidase FAP Proteins 0.000 description 2
• 102000002727 Protein Tyrosine Phosphatase Human genes 0.000 description 2
• 102000053067 Pyruvate Dehydrogenase Acetyl-Transferring Kinase Human genes 0.000 description 2
• 102000034527 Retinoid X Receptors Human genes 0.000 description 2
• 108010038912 Retinoid X Receptors Proteins 0.000 description 2
• YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
• 229930006000 Sucrose Natural products 0.000 description 2
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
• 229920001615 Tragacanth Polymers 0.000 description 2
• 239000007983 Tris buffer Substances 0.000 description 2
• ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
• FKCMADOPPWWGNZ-YUMQZZPRSA-N [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1B(O)O FKCMADOPPWWGNZ-YUMQZZPRSA-N 0.000 description 2
• JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 2
• 101710159466 [Pyruvate dehydrogenase (acetyl-transferring)] kinase, mitochondrial Proteins 0.000 description 2
• 230000002378 acidificating effect Effects 0.000 description 2
• 150000007513 acids Chemical class 0.000 description 2
• 230000009471 action Effects 0.000 description 2
• 239000013543 active substance Substances 0.000 description 2
• 230000001154 acute effect Effects 0.000 description 2
• 210000000577 adipose tissue Anatomy 0.000 description 2
• 239000011543 agarose gel Substances 0.000 description 2
• 230000001476 alcoholic effect Effects 0.000 description 2
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
• 150000004703 alkoxides Chemical class 0.000 description 2
• 125000005596 alkyl carboxamido group Chemical group 0.000 description 2
• 230000004075 alteration Effects 0.000 description 2
• 125000003368 amide group Chemical group 0.000 description 2
• 238000005576 amination reaction Methods 0.000 description 2
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 2
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
• 239000012911 assay medium Substances 0.000 description 2
• XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
• BYBIRLURVZSVME-UHFFFAOYSA-M benzene;copper(1+);trifluoromethanesulfonate Chemical compound [Cu+].C1=CC=CC=C1.[O-]S(=O)(=O)C(F)(F)F BYBIRLURVZSVME-UHFFFAOYSA-M 0.000 description 2
• 230000036772 blood pressure Effects 0.000 description 2
• 125000001246 bromo group Chemical group Br* 0.000 description 2
• OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 2
• 229960002802 bromocriptine Drugs 0.000 description 2
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
• 229910000024 caesium carbonate Inorganic materials 0.000 description 2
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
• 150000001768 cations Chemical class 0.000 description 2
• 239000013553 cell monolayer Substances 0.000 description 2
• 238000007385 chemical modification Methods 0.000 description 2
• 229940110456 cocoa butter Drugs 0.000 description 2
• 235000019868 cocoa butter Nutrition 0.000 description 2
• OHCQJHSOBUTRHG-UHFFFAOYSA-N colforsin Natural products OC12C(=O)CC(C)(C=C)OC1(C)C(OC(=O)C)C(O)C1C2(C)C(O)CCC1(C)C OHCQJHSOBUTRHG-UHFFFAOYSA-N 0.000 description 2
• 229940125961 compound 24 Drugs 0.000 description 2
• 239000008120 corn starch Substances 0.000 description 2
• KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 2
• 230000006378 damage Effects 0.000 description 2
• 230000002950 deficient Effects 0.000 description 2
• 239000008121 dextrose Substances 0.000 description 2
• 235000005911 diet Nutrition 0.000 description 2
• 230000037213 diet Effects 0.000 description 2
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
• IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
• 239000000428 dust Substances 0.000 description 2
• 230000002526 effect on cardiovascular system Effects 0.000 description 2
• 239000003995 emulsifying agent Substances 0.000 description 2
• 238000005516 engineering process Methods 0.000 description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
• 238000001704 evaporation Methods 0.000 description 2
• 238000013213 extrapolation Methods 0.000 description 2
• OLNTVTPDXPETLC-XPWALMASSA-N ezetimibe Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(O)=CC=1)C1=CC=C(F)C=C1 OLNTVTPDXPETLC-XPWALMASSA-N 0.000 description 2
• 229960000815 ezetimibe Drugs 0.000 description 2
• 150000004665 fatty acids Chemical class 0.000 description 2
• 235000019634 flavors Nutrition 0.000 description 2
• IRXSLJNXXZKURP-UHFFFAOYSA-N fluorenylmethyloxycarbonyl chloride Chemical compound C1=CC=C2C(COC(=O)Cl)C3=CC=CC=C3C2=C1 IRXSLJNXXZKURP-UHFFFAOYSA-N 0.000 description 2
• MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 description 2
• 239000012634 fragment Substances 0.000 description 2
• 239000000446 fuel Substances 0.000 description 2
• 230000005714 functional activity Effects 0.000 description 2
• 125000000524 functional group Chemical group 0.000 description 2
• 208000004104 gestational diabetes Diseases 0.000 description 2
• 239000008187 granular material Substances 0.000 description 2
• 230000012010 growth Effects 0.000 description 2
• 230000005802 health problem Effects 0.000 description 2
• 230000002440 hepatic effect Effects 0.000 description 2
• 235000003642 hunger Nutrition 0.000 description 2
• 238000003384 imaging method Methods 0.000 description 2
• 238000001802 infusion Methods 0.000 description 2
• 229910052500 inorganic mineral Inorganic materials 0.000 description 2
• 210000002660 insulin-secreting cell Anatomy 0.000 description 2
• 238000001990 intravenous administration Methods 0.000 description 2
• HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
• 238000002955 isolation Methods 0.000 description 2
• 150000002576 ketones Chemical group 0.000 description 2
• 238000002372 labelling Methods 0.000 description 2
• 150000002596 lactones Chemical group 0.000 description 2
• NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical class O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 2
• 239000012280 lithium aluminium hydride Substances 0.000 description 2
• 239000006210 lotion Substances 0.000 description 2
• 239000000314 lubricant Substances 0.000 description 2
• 235000019359 magnesium stearate Nutrition 0.000 description 2
• 230000007246 mechanism Effects 0.000 description 2
• 238000002844 melting Methods 0.000 description 2
• 230000008018 melting Effects 0.000 description 2
• 229920000609 methyl cellulose Polymers 0.000 description 2
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
• 239000001923 methylcellulose Substances 0.000 description 2
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
• 235000010755 mineral Nutrition 0.000 description 2
• 239000011707 mineral Substances 0.000 description 2
• KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 2
• KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 2
• 210000003928 nasal cavity Anatomy 0.000 description 2
• 239000006199 nebulizer Substances 0.000 description 2
• 229910017604 nitric acid Inorganic materials 0.000 description 2
• 239000000346 nonvolatile oil Substances 0.000 description 2
• 239000002767 noradrenalin uptake inhibitor Substances 0.000 description 2
• URPYMXQQVHTUDU-OFGSCBOVSA-N nucleopeptide y Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 URPYMXQQVHTUDU-OFGSCBOVSA-N 0.000 description 2
• 208000015380 nutritional deficiency disease Diseases 0.000 description 2
• 239000002674 ointment Substances 0.000 description 2
• 150000002894 organic compounds Chemical class 0.000 description 2
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
• 230000003647 oxidation Effects 0.000 description 2
• 238000007254 oxidation reaction Methods 0.000 description 2
• 239000001301 oxygen Substances 0.000 description 2
• 125000004430 oxygen atom Chemical group O* 0.000 description 2
• 229920002866 paraformaldehyde Polymers 0.000 description 2
• 239000006201 parenteral dosage form Substances 0.000 description 2
• 239000002245 particle Substances 0.000 description 2
• AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
• ZOIYGIYMRAFGGA-UHFFFAOYSA-N pentan-3-yl 4-(6-chloro-5-methoxypyrimidin-4-yl)oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(CC)CC)CCC1OC1=NC=NC(Cl)=C1OC ZOIYGIYMRAFGGA-UHFFFAOYSA-N 0.000 description 2
• 208000033808 peripheral neuropathy Diseases 0.000 description 2
• 239000000546 pharmaceutical excipient Substances 0.000 description 2
• DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 2
• RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
• 229950007002 phosphocreatine Drugs 0.000 description 2
• 239000000049 pigment Substances 0.000 description 2
• 239000006187 pill Substances 0.000 description 2
• HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 2
• 229960005235 piperonyl butoxide Drugs 0.000 description 2
• 229910052697 platinum Inorganic materials 0.000 description 2
• 239000002798 polar solvent Substances 0.000 description 2
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
• 230000029537 positive regulation of insulin secretion Effects 0.000 description 2
• 229920001592 potato starch Polymers 0.000 description 2
• 229960002429 proline Drugs 0.000 description 2
• 230000002035 prolonged effect Effects 0.000 description 2
• DOGIXZSTBWGSLC-UHFFFAOYSA-N propan-2-yl 4-(2-chloro-3-methoxypyridin-4-yl)oxypiperidine-1-carboxylate Chemical compound COC1=C(Cl)N=CC=C1OC1CCN(C(=O)OC(C)C)CC1 DOGIXZSTBWGSLC-UHFFFAOYSA-N 0.000 description 2
• SCNSHISVJKQLNR-UHFFFAOYSA-N propan-2-yl 4-[5-hydroxy-6-[(2-methyl-6-methylsulfonylpyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1OC1=NC=NC(NC=2C(=NC(=CC=2)S(C)(=O)=O)C)=C1O SCNSHISVJKQLNR-UHFFFAOYSA-N 0.000 description 2
• WRWBENIVDXGNIY-UHFFFAOYSA-N propan-2-yl 4-[5-methoxy-6-[(2-methyl-6-propan-2-ylsulfonylpyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(S(=O)(=O)C(C)C)N=C1C WRWBENIVDXGNIY-UHFFFAOYSA-N 0.000 description 2
• CHNODHSNXJVSEJ-UHFFFAOYSA-N propan-2-yl 4-[5-methoxy-6-[(2-methyl-6-propylsulfanylpyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound CC1=NC(SCCC)=CC=C1NC1=NC=NC(OC2CCN(CC2)C(=O)OC(C)C)=C1OC CHNODHSNXJVSEJ-UHFFFAOYSA-N 0.000 description 2
• TYWXJFBTQHXVJK-UHFFFAOYSA-N propan-2-yl 4-[5-methoxy-6-[(4-methyl-6-methylsulfonylpyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CN=C(S(C)(=O)=O)C=C1C TYWXJFBTQHXVJK-UHFFFAOYSA-N 0.000 description 2
• IRDWSTCTZIWYCR-UHFFFAOYSA-N propan-2-yl 4-[5-methoxy-6-[[2-methyl-6-(2-methylsulfanylethyl)pyridin-3-yl]amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(CCSC)N=C1C IRDWSTCTZIWYCR-UHFFFAOYSA-N 0.000 description 2
• JALXZXXHRMBIKH-UHFFFAOYSA-N propan-2-yl 4-[6-(2-fluoro-4-methylsulfonylphenoxy)-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC=2C(=CC(=CC=2)S(C)(=O)=O)F)C(OC)=C1OC1CCN(C(=O)OC(C)C)CC1 JALXZXXHRMBIKH-UHFFFAOYSA-N 0.000 description 2
• UAZKOSDHSWQLOJ-UHFFFAOYSA-N propan-2-yl 4-[6-(4-bromo-2-methoxyanilino)-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound COC1=CC(Br)=CC=C1NC1=NC=NC(OC2CCN(CC2)C(=O)OC(C)C)=C1OC UAZKOSDHSWQLOJ-UHFFFAOYSA-N 0.000 description 2
• OSGRSTPCRDHJAW-UHFFFAOYSA-N propan-2-yl 4-[6-[(6-cyano-4-methylpyridin-3-yl)amino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CN=C(C#N)C=C1C OSGRSTPCRDHJAW-UHFFFAOYSA-N 0.000 description 2
• UKVIBHRSFKWRPA-UHFFFAOYSA-N propan-2-yl 4-hydroxypiperidine-1-carboxylate Chemical compound CC(C)OC(=O)N1CCC(O)CC1 UKVIBHRSFKWRPA-UHFFFAOYSA-N 0.000 description 2
• SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
• 239000003380 propellant Substances 0.000 description 2
• 235000019833 protease Nutrition 0.000 description 2
• 238000000159 protein binding assay Methods 0.000 description 2
• 108020000494 protein-tyrosine phosphatase Proteins 0.000 description 2
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
• 150000003222 pyridines Chemical class 0.000 description 2
• 239000000700 radioactive tracer Substances 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• 229940044601 receptor agonist Drugs 0.000 description 2
• 239000000018 receptor agonist Substances 0.000 description 2
• 238000011160 research Methods 0.000 description 2
• 210000002345 respiratory system Anatomy 0.000 description 2
• 238000012552 review Methods 0.000 description 2
• 229910052702 rhenium Inorganic materials 0.000 description 2
• BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 description 2
• 229960000672 rosuvastatin Drugs 0.000 description 2
• FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
• 229920006395 saturated elastomer Polymers 0.000 description 2
• 238000007423 screening assay Methods 0.000 description 2
• 150000003335 secondary amines Chemical class 0.000 description 2
• 229940076279 serotonin Drugs 0.000 description 2
• 210000002966 serum Anatomy 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
• 235000017557 sodium bicarbonate Nutrition 0.000 description 2
• 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
• 239000012312 sodium hydride Substances 0.000 description 2
• 230000009870 specific binding Effects 0.000 description 2
• 238000007920 subcutaneous administration Methods 0.000 description 2
• 239000005720 sucrose Substances 0.000 description 2
• 239000000454 talc Substances 0.000 description 2
• 229910052623 talc Inorganic materials 0.000 description 2
• PMIIQVVRXQTGAG-UHFFFAOYSA-N tert-butyl 4-(6-chloro-5-methoxypyrimidin-4-yl)oxypiperidine-1-carboxylate Chemical compound COC1=C(Cl)N=CN=C1OC1CCN(C(=O)OC(C)(C)C)CC1 PMIIQVVRXQTGAG-UHFFFAOYSA-N 0.000 description 2
• PIVVWJQOODINOO-UHFFFAOYSA-N tert-butyl-[(4-methyl-5-nitropyridin-2-yl)methoxy]-diphenylsilane Chemical compound C1=C([N+]([O-])=O)C(C)=CC(CO[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C(C)(C)C)=N1 PIVVWJQOODINOO-UHFFFAOYSA-N 0.000 description 2
• MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 2
• QLAGGSISYQIPRW-UHFFFAOYSA-N tert-butyl-dimethyl-[2-(6-methyl-5-nitropyridin-2-yl)sulfanylethoxy]silane Chemical compound CC1=NC(SCCO[Si](C)(C)C(C)(C)C)=CC=C1[N+]([O-])=O QLAGGSISYQIPRW-UHFFFAOYSA-N 0.000 description 2
• HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
• 229940124597 therapeutic agent Drugs 0.000 description 2
• 238000011200 topical administration Methods 0.000 description 2
• 235000010487 tragacanth Nutrition 0.000 description 2
• 239000000196 tragacanth Substances 0.000 description 2
• 229940116362 tragacanth Drugs 0.000 description 2
• 230000009466 transformation Effects 0.000 description 2
• 229910052723 transition metal Inorganic materials 0.000 description 2
• 150000003624 transition metals Chemical class 0.000 description 2
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
• CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
• 239000000080 wetting agent Substances 0.000 description 2
• 238000010626 work up procedure Methods 0.000 description 2
• SKBXVAOMEVOTGJ-UHFFFAOYSA-N xi-Pinol Chemical compound CC1=CCC2C(C)(C)OC1C2 SKBXVAOMEVOTGJ-UHFFFAOYSA-N 0.000 description 2
• DBGIVFWFUFKIQN-VIFPVBQESA-N (+)-Fenfluramine Chemical compound CCN[C@@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-VIFPVBQESA-N 0.000 description 1
• DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 1
• VDLOJRUTNRJDJO-ZYNSJIGGSA-N (1s,2s,3r,4s,5s)-5-amino-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol Chemical compound N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O VDLOJRUTNRJDJO-ZYNSJIGGSA-N 0.000 description 1
• 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 description 1
• VXEVKSKAINMPFG-QWUNSSNDSA-N (2S)-5-[[(5S)-5-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S,3R)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]amino]propanoyl]amino]-4-carboxybutanoyl]amino]acetyl]amino]-3-hydroxybutanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-3-methylbutanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentanoyl]amino]-4-carboxybutanoyl]amino]acetyl]amino]-5-oxopentanoyl]amino]propanoyl]amino]propanoyl]amino]-6-[[(2S)-4-carboxy-1-[[(2S)-1-[[(2S,3S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-(carboxymethylamino)-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxobutan-2-yl]amino]-6-oxohexyl]amino]-2-(hexadecanoylamino)-5-hydroxypentanoic acid Chemical compound CCCCCCCCCCCCCCCC(=O)N[C@@H](CCC(NCCCC[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC2=CNC3=CC=CC=C32)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(=O)N)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC4=CC=C(C=C4)O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC5=CC=CC=C5)NC(=O)[C@H]([C@@H](C)O)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](CC6=CNC=N6)N)O)C(=O)O VXEVKSKAINMPFG-QWUNSSNDSA-N 0.000 description 1
• AMNXBQPRODZJQR-DITALETJSA-N (2s)-2-cyclopentyl-2-[3-[(2,4-dimethylpyrido[2,3-b]indol-9-yl)methyl]phenyl]-n-[(1r)-2-hydroxy-1-phenylethyl]acetamide Chemical compound C1([C@@H](C=2C=CC=C(C=2)CN2C3=CC=CC=C3C3=C(C)C=C(N=C32)C)C(=O)N[C@@H](CO)C=2C=CC=CC=2)CCCC1 AMNXBQPRODZJQR-DITALETJSA-N 0.000 description 1
• ZXEIEKDGPVTZLD-NDEPHWFRSA-N (2s)-2-dodecylsulfanyl-n-(4-hydroxy-2,3,5-trimethylphenyl)-2-phenylacetamide Chemical compound O=C([C@@H](SCCCCCCCCCCCC)C=1C=CC=CC=1)NC1=CC(C)=C(O)C(C)=C1C ZXEIEKDGPVTZLD-NDEPHWFRSA-N 0.000 description 1
• WCRLBFHWFPELKW-YUMQZZPRSA-N (2s,3s)-2-amino-3-methyl-1-(1,3-thiazolidin-3-yl)pentan-1-one Chemical compound CC[C@H](C)[C@H](N)C(=O)N1CCSC1 WCRLBFHWFPELKW-YUMQZZPRSA-N 0.000 description 1
• HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 description 1
• BIDNLKIUORFRQP-XYGFDPSESA-N (2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C(O)=O)CCCC1=CC=CC=C1 BIDNLKIUORFRQP-XYGFDPSESA-N 0.000 description 1
• ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 1
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
• DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
• WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
• PMGZJNCIQHGNLT-UHFFFAOYSA-N 1-[bis(2,2-dimethylpropanoyloxymethoxy)phosphoryl]-4-(3-phenoxyphenyl)butane-1-sulfonic acid Chemical compound CC(C)(C)C(=O)OCOP(=O)(OCOC(=O)C(C)(C)C)C(S(O)(=O)=O)CCCC1=CC=CC(OC=2C=CC=CC=2)=C1 PMGZJNCIQHGNLT-UHFFFAOYSA-N 0.000 description 1
• 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
• VZOPVKZLLGMDDG-UHFFFAOYSA-N 1-oxido-4-phenylpyridin-1-ium Chemical compound C1=C[N+]([O-])=CC=C1C1=CC=CC=C1 VZOPVKZLLGMDDG-UHFFFAOYSA-N 0.000 description 1
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
• 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical group CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
• GMAJNANLBOHCAU-UHFFFAOYSA-N 2,4-dimethyl-5-nitropyridine Chemical compound CC1=CC(C)=C([N+]([O-])=O)C=N1 GMAJNANLBOHCAU-UHFFFAOYSA-N 0.000 description 1
• WHXBGXNSIUVAAP-UHFFFAOYSA-N 2,5-difluoro-4-propoxyaniline Chemical compound CCCOC1=CC(F)=C(N)C=C1F WHXBGXNSIUVAAP-UHFFFAOYSA-N 0.000 description 1
• INXKVYFOWNAVMU-UHFFFAOYSA-N 2,5-difluorophenol Chemical compound OC1=CC(F)=CC=C1F INXKVYFOWNAVMU-UHFFFAOYSA-N 0.000 description 1
• AETHUDGJSSKZKT-UHFFFAOYSA-N 2,6-dimethyl-3-nitropyridine Chemical compound CC1=CC=C([N+]([O-])=O)C(C)=N1 AETHUDGJSSKZKT-UHFFFAOYSA-N 0.000 description 1
• QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 description 1
• 239000003315 2-(4-chlorophenoxy)-2-methylpropanoic acid Substances 0.000 description 1
• VHGKPULIEFXFLD-UHFFFAOYSA-N 2-(5-amino-6-methylpyridin-2-yl)sulfanylethanol Chemical compound CC1=NC(SCCO)=CC=C1N VHGKPULIEFXFLD-UHFFFAOYSA-N 0.000 description 1
• QRXFWNAZDAMHGI-UHFFFAOYSA-N 2-(5-nitropyridin-2-yl)sulfanylethanol Chemical compound OCCSC1=CC=C([N+]([O-])=O)C=N1 QRXFWNAZDAMHGI-UHFFFAOYSA-N 0.000 description 1
• XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
• IHBAVXVTGLANPI-QMMMGPOBSA-N 2-amino-3-methyl-1-pyrrolidin-1-yl-butan-1-one Chemical compound CC(C)[C@H](N)C(=O)N1CCCC1 IHBAVXVTGLANPI-QMMMGPOBSA-N 0.000 description 1
• TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
• OSYUAHGEDKTDOX-UHFFFAOYSA-N 2-bromo-4-methyl-5-nitropyridine Chemical compound CC1=CC(Br)=NC=C1[N+]([O-])=O OSYUAHGEDKTDOX-UHFFFAOYSA-N 0.000 description 1
• CUMTUBVTKOYYOU-UHFFFAOYSA-N 2-fluoro-4-iodoaniline Chemical compound NC1=CC=C(I)C=C1F CUMTUBVTKOYYOU-UHFFFAOYSA-N 0.000 description 1
• GRCLBOGXTPXNPL-UHFFFAOYSA-N 2-fluoropyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=C1F GRCLBOGXTPXNPL-UHFFFAOYSA-N 0.000 description 1
• ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
• CCFGTKQIRWHYTB-UHFFFAOYSA-N 2-methyl-3-nitropyridine Chemical compound CC1=NC=CC=C1[N+]([O-])=O CCFGTKQIRWHYTB-UHFFFAOYSA-N 0.000 description 1
• PYMDWPYHKGEXIB-UHFFFAOYSA-N 2-methyl-6-(2-methylsulfonylpropan-2-yl)-3-nitropyridine Chemical compound CC1=NC(C(C)(C)S(C)(=O)=O)=CC=C1[N+]([O-])=O PYMDWPYHKGEXIB-UHFFFAOYSA-N 0.000 description 1
• SUKKKMWTKKPGMY-UHFFFAOYSA-N 2-methyl-6-(methylsulfonylmethyl)-3-nitropyridine Chemical compound CC1=NC(CS(C)(=O)=O)=CC=C1[N+]([O-])=O SUKKKMWTKKPGMY-UHFFFAOYSA-N 0.000 description 1
• YZQLWPMZQVHJED-UHFFFAOYSA-N 2-methylpropanethioic acid S-[2-[[[1-(2-ethylbutyl)cyclohexyl]-oxomethyl]amino]phenyl] ester Chemical compound C=1C=CC=C(SC(=O)C(C)C)C=1NC(=O)C1(CC(CC)CC)CCCCC1 YZQLWPMZQVHJED-UHFFFAOYSA-N 0.000 description 1
• WAJVHEQRSWOOHH-UHFFFAOYSA-N 2-n-(2-methoxyethyl)-6-methylpyridine-2,5-diamine Chemical compound COCCNC1=CC=C(N)C(C)=N1 WAJVHEQRSWOOHH-UHFFFAOYSA-N 0.000 description 1
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
• VNDWQCSOSCCWIP-UHFFFAOYSA-N 2-tert-butyl-9-fluoro-1,6-dihydrobenzo[h]imidazo[4,5-f]isoquinolin-7-one Chemical compound C1=2C=CNC(=O)C=2C2=CC(F)=CC=C2C2=C1NC(C(C)(C)C)=N2 VNDWQCSOSCCWIP-UHFFFAOYSA-N 0.000 description 1
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
• DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 1
• WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 1
• 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• QXZBMSIDSOZZHK-DOPDSADYSA-N 31362-50-2 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1NC(=O)CC1)C(C)C)C1=CNC=N1 QXZBMSIDSOZZHK-DOPDSADYSA-N 0.000 description 1
• NRGYTONERIQIBW-UHFFFAOYSA-N 4,6-dimethyl-2-(6-phenylhexylamino)pyrimidin-5-ol Chemical compound CC1=C(O)C(C)=NC(NCCCCCCC=2C=CC=CC=2)=N1 NRGYTONERIQIBW-UHFFFAOYSA-N 0.000 description 1
• IJXOIJMLQCYEMI-UHFFFAOYSA-N 4-(6-chloro-5-methoxypyrimidin-4-yl)oxypiperidine-1-carboxylic acid Chemical compound COC1=C(Cl)N=CN=C1OC1CCN(C(O)=O)CC1 IJXOIJMLQCYEMI-UHFFFAOYSA-N 0.000 description 1
• BOHJNTZFJPIDAT-UHFFFAOYSA-N 4-[5-methoxy-6-[(2-methyl-6-propylsulfanylpyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylic acid Chemical compound COC=1C(=NC=NC=1NC=1C(=NC(=CC=1)SCCC)C)OC1CCN(CC1)C(=O)O BOHJNTZFJPIDAT-UHFFFAOYSA-N 0.000 description 1
• GOAZGYBNYKYOMP-UHFFFAOYSA-N 4-[6-[[6-(carboxymethyl)-2-methylpyridin-3-yl]amino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylic acid Chemical compound C(=O)(O)CC1=CC=C(C(=N1)C)NC1=C(C(=NC=N1)OC1CCN(CC1)C(=O)O)OC GOAZGYBNYKYOMP-UHFFFAOYSA-N 0.000 description 1
• RYVOZMPTISNBDB-UHFFFAOYSA-N 4-bromo-2-fluorophenol Chemical compound OC1=CC=C(Br)C=C1F RYVOZMPTISNBDB-UHFFFAOYSA-N 0.000 description 1
• WRFYIYOXJWKONR-UHFFFAOYSA-N 4-bromo-2-methoxyaniline Chemical compound COC1=CC(Br)=CC=C1N WRFYIYOXJWKONR-UHFFFAOYSA-N 0.000 description 1
• WUBYNMSQVOSTHI-UHFFFAOYSA-N 4-methyl-6-methylsulfonylpyridin-3-amine Chemical compound CC1=CC(S(C)(=O)=O)=NC=C1N WUBYNMSQVOSTHI-UHFFFAOYSA-N 0.000 description 1
• LLKFNPUXQZHIAE-UHFFFAOYSA-N 5-(3-aminopropyl)-8-bromo-3-methyl-2h-pyrazolo[4,3-c]quinolin-4-one Chemical compound O=C1N(CCCN)C2=CC=C(Br)C=C2C2=C1C(C)=NN2 LLKFNPUXQZHIAE-UHFFFAOYSA-N 0.000 description 1
• LNUZOTGDXSQBJP-UHFFFAOYSA-N 5-methoxy-n-(2-methyl-6-methylsulfonylpyridin-3-yl)-6-[1-(3-propan-2-yl-1,2,4-oxadiazol-5-yl)piperidin-4-yl]oxypyrimidin-4-amine Chemical compound N1=CN=C(OC2CCN(CC2)C=2ON=C(N=2)C(C)C)C(OC)=C1NC1=CC=C(S(C)(=O)=O)N=C1C LNUZOTGDXSQBJP-UHFFFAOYSA-N 0.000 description 1
• UBTQJSZELCWGCN-UHFFFAOYSA-N 6-bromo-2-methylpyridin-3-amine Chemical compound CC1=NC(Br)=CC=C1N UBTQJSZELCWGCN-UHFFFAOYSA-N 0.000 description 1
• GDUANFXPOZTYKS-UHFFFAOYSA-N 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid Chemical compound FC1=CC(OC)=CC(F)=C1C(=O)NC1=CC(Br)=CC2=C1OC(C(O)=O)=CC2=O GDUANFXPOZTYKS-UHFFFAOYSA-N 0.000 description 1
• GHSRMSJVYMITDX-UHFFFAOYSA-N 6-chloro-2-methyl-3-nitropyridine Chemical compound CC1=NC(Cl)=CC=C1[N+]([O-])=O GHSRMSJVYMITDX-UHFFFAOYSA-N 0.000 description 1
• PLSMBLIGZJWLEJ-UHFFFAOYSA-N 6-chloro-4-methylpyridin-3-amine Chemical compound CC1=CC(Cl)=NC=C1N PLSMBLIGZJWLEJ-UHFFFAOYSA-N 0.000 description 1
• XXWLHILHNANUFH-UHFFFAOYSA-N 6-fluoro-2-methylpyridin-3-amine Chemical compound CC1=NC(F)=CC=C1N XXWLHILHNANUFH-UHFFFAOYSA-N 0.000 description 1
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
• 208000011732 Abnormal glucose homeostasis Diseases 0.000 description 1
• 241000251468 Actinopterygii Species 0.000 description 1
• 239000000275 Adrenocorticotropic Hormone Substances 0.000 description 1
• 102000054930 Agouti-Related Human genes 0.000 description 1
• 101710127426 Agouti-related protein Proteins 0.000 description 1
• FHHHOYXPRDYHEZ-COXVUDFISA-N Alacepril Chemical compound CC(=O)SC[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 FHHHOYXPRDYHEZ-COXVUDFISA-N 0.000 description 1
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
• 239000004382 Amylase Substances 0.000 description 1
• 229940127438 Amylin Agonists Drugs 0.000 description 1
• 102000008873 Angiotensin II receptor Human genes 0.000 description 1
• 108050000824 Angiotensin II receptor Proteins 0.000 description 1
• 102000015427 Angiotensins Human genes 0.000 description 1
• 108010064733 Angiotensins Proteins 0.000 description 1
• 102000018616 Apolipoproteins B Human genes 0.000 description 1
• 108010027006 Apolipoproteins B Proteins 0.000 description 1
• 241001120493 Arene Species 0.000 description 1
• XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
• XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 1
• XPCFTKFZXHTYIP-PMACEKPBSA-N Benazepril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 XPCFTKFZXHTYIP-PMACEKPBSA-N 0.000 description 1
• 108010051479 Bombesin Proteins 0.000 description 1
• 102000013585 Bombesin Human genes 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
• FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
• 239000002083 C09CA01 - Losartan Substances 0.000 description 1
• UHXDMYCURGBQNC-UHFFFAOYSA-N CN(C(=O)CC1=CC=C(C(=N1)C)NC1=C(C(=NC=N1)OC1CCN(CC1)C(=O)O)OC)C Chemical compound CN(C(=O)CC1=CC=C(C(=N1)C)NC1=C(C(=NC=N1)OC1CCN(CC1)C(=O)O)OC)C UHXDMYCURGBQNC-UHFFFAOYSA-N 0.000 description 1
• 235000017399 Caesalpinia tinctoria Nutrition 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• 241000283707 Capra Species 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
• 102000014914 Carrier Proteins Human genes 0.000 description 1
• IFYLTXNCFVRALQ-OALUTQOASA-N Ceronapril Chemical compound O([C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)P(O)(=O)CCCCC1=CC=CC=C1 IFYLTXNCFVRALQ-OALUTQOASA-N 0.000 description 1
• BMOVQUBVGICXQN-UHFFFAOYSA-N Clinofibrate Chemical compound C1=CC(OC(C)(CC)C(O)=O)=CC=C1C1(C=2C=CC(OC(C)(CC)C(O)=O)=CC=2)CCCCC1 BMOVQUBVGICXQN-UHFFFAOYSA-N 0.000 description 1
• 108091026890 Coding region Proteins 0.000 description 1
• 102100025892 Complement C1q tumor necrosis factor-related protein 1 Human genes 0.000 description 1
• 101800000414 Corticotropin Proteins 0.000 description 1
• 102000036364 Cullin Ring E3 Ligases Human genes 0.000 description 1
• IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 1
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
• 108020003215 DNA Probes Proteins 0.000 description 1
• 239000003298 DNA probe Substances 0.000 description 1
• FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 description 1
• 239000004375 Dextrin Substances 0.000 description 1
• 229920001353 Dextrin Polymers 0.000 description 1
• 208000002249 Diabetes Complications Diseases 0.000 description 1
• 206010012735 Diarrhoea Diseases 0.000 description 1
• 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
• 238000002965 ELISA Methods 0.000 description 1
• 108010061435 Enalapril Proteins 0.000 description 1
• 108010066671 Enalaprilat Proteins 0.000 description 1
• 241000283086 Equidae Species 0.000 description 1
• 108700039887 Essential Genes Proteins 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• 108010011459 Exenatide Proteins 0.000 description 1
• 108090000331 Firefly luciferases Proteins 0.000 description 1
• 102000027487 Fructose-Bisphosphatase Human genes 0.000 description 1
• 108010017464 Fructose-Bisphosphatase Proteins 0.000 description 1
• 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 description 1
• GGUVRMBIEPYOKL-WMVCGJOFSA-N GW 409544 Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C=CC=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 GGUVRMBIEPYOKL-WMVCGJOFSA-N 0.000 description 1
• 102400001370 Galanin Human genes 0.000 description 1
• 101800002068 Galanin Proteins 0.000 description 1
• 241000287828 Gallus gallus Species 0.000 description 1
• 108010016122 Ghrelin Receptors Proteins 0.000 description 1
• 208000010412 Glaucoma Diseases 0.000 description 1
• 229940122904 Glucagon receptor antagonist Drugs 0.000 description 1
• DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 description 1
• 102400000322 Glucagon-like peptide 1 Human genes 0.000 description 1
• FAEKWTJYAYMJKF-QHCPKHFHSA-N GlucoNorm Chemical compound C1=C(C(O)=O)C(OCC)=CC(CC(=O)N[C@@H](CC(C)C)C=2C(=CC=CC=2)N2CCCCC2)=C1 FAEKWTJYAYMJKF-QHCPKHFHSA-N 0.000 description 1
• 102000004366 Glucosidases Human genes 0.000 description 1
• 108010056771 Glucosidases Proteins 0.000 description 1
• 102100031181 Glyceraldehyde-3-phosphate dehydrogenase Human genes 0.000 description 1
• 229920002527 Glycogen Polymers 0.000 description 1
• 102100039256 Growth hormone secretagogue receptor type 1 Human genes 0.000 description 1
• 239000007821 HATU Substances 0.000 description 1
• 229920000209 Hexadimethrine bromide Polymers 0.000 description 1
• 101000928179 Homo sapiens Agouti-related protein Proteins 0.000 description 1
• 102000004286 Hydroxymethylglutaryl CoA Reductases Human genes 0.000 description 1
• 108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 description 1
• 208000013016 Hypoglycemia Diseases 0.000 description 1
• ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
• 102000000853 LDL receptors Human genes 0.000 description 1
• 108010001831 LDL receptors Proteins 0.000 description 1
• 229940127470 Lipase Inhibitors Drugs 0.000 description 1
• 229940086609 Lipase inhibitor Drugs 0.000 description 1
• 108010007859 Lisinopril Proteins 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• 108010000410 MSH receptor Proteins 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• ZPXSCAKFGYXMGA-UHFFFAOYSA-N Mazindol Chemical compound N12CCN=C2C2=CC=CC=C2C1(O)C1=CC=C(Cl)C=C1 ZPXSCAKFGYXMGA-UHFFFAOYSA-N 0.000 description 1
• 102400001132 Melanin-concentrating hormone Human genes 0.000 description 1
• 101800002739 Melanin-concentrating hormone Proteins 0.000 description 1
• 102100034216 Melanocyte-stimulating hormone receptor Human genes 0.000 description 1
• 102000018697 Membrane Proteins Human genes 0.000 description 1
• 108010052285 Membrane Proteins Proteins 0.000 description 1
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
• 229940127308 Microsomal Triglyceride Transfer Protein Inhibitors Drugs 0.000 description 1
• IBAQFPQHRJAVAV-ULAWRXDQSA-N Miglitol Chemical compound OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO IBAQFPQHRJAVAV-ULAWRXDQSA-N 0.000 description 1
• 229920000881 Modified starch Polymers 0.000 description 1
• PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 1
• KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
• SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
• AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 1
• QQGNLKJAIVSNCO-UHFFFAOYSA-N N-butylformamide Chemical compound CCCCNC=O QQGNLKJAIVSNCO-UHFFFAOYSA-N 0.000 description 1
• AHLBNYSZXLDEJQ-UHFFFAOYSA-N N-formyl-L-leucylester Natural products CCCCCCCCCCCC(OC(=O)C(CC(C)C)NC=O)CC1OC(=O)C1CCCCCC AHLBNYSZXLDEJQ-UHFFFAOYSA-N 0.000 description 1
• 229920002274 Nalgene Polymers 0.000 description 1
• 206010028980 Neoplasm Diseases 0.000 description 1
• 208000028389 Nerve injury Diseases 0.000 description 1
• 102000030937 Neuromedin U receptor Human genes 0.000 description 1
• 108010002741 Neuromedin U receptor Proteins 0.000 description 1
• 238000000636 Northern blotting Methods 0.000 description 1
• 102000007399 Nuclear hormone receptor Human genes 0.000 description 1
• 108020005497 Nuclear hormone receptor Proteins 0.000 description 1
• 239000005642 Oleic acid Substances 0.000 description 1
• ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
• 229940123730 Orexin receptor antagonist Drugs 0.000 description 1
• 238000012408 PCR amplification Methods 0.000 description 1
• 208000002193 Pain Diseases 0.000 description 1
• 241001494479 Pecora Species 0.000 description 1
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
• 235000014676 Phragmites communis Nutrition 0.000 description 1
• 102000002808 Pituitary adenylate cyclase-activating polypeptide Human genes 0.000 description 1
• 108010004684 Pituitary adenylate cyclase-activating polypeptide Proteins 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 1
• 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
• 241000288906 Primates Species 0.000 description 1
• 102100040918 Pro-glucagon Human genes 0.000 description 1
• 101710184309 Probable sucrose-6-phosphate hydrolase Proteins 0.000 description 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
• 208000017442 Retinal disease Diseases 0.000 description 1
• 206010038923 Retinopathy Diseases 0.000 description 1
• 241000316848 Rhodococcus <scale insect> Species 0.000 description 1
• RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
• 108010077895 Sarcosine Proteins 0.000 description 1
• JLRNKCZRCMIVKA-UHFFFAOYSA-N Simfibrate Chemical compound C=1C=C(Cl)C=CC=1OC(C)(C)C(=O)OCCCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 JLRNKCZRCMIVKA-UHFFFAOYSA-N 0.000 description 1
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
• 102400000472 Sucrase Human genes 0.000 description 1
• 101710112652 Sucrose-6-phosphate hydrolase Proteins 0.000 description 1
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
• UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
• 241000282898 Sus scrofa Species 0.000 description 1
• 239000000150 Sympathomimetic Substances 0.000 description 1
• 241000388430 Tara Species 0.000 description 1
• 244000269722 Thea sinensis Species 0.000 description 1
• 241000473945 Theria <moth genus> Species 0.000 description 1
• VXFJYXUZANRPDJ-WTNASJBWSA-N Trandopril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@H]2CCCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 VXFJYXUZANRPDJ-WTNASJBWSA-N 0.000 description 1
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
• IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 1
• 108010059705 Urocortins Proteins 0.000 description 1
• 102000005630 Urocortins Human genes 0.000 description 1
• VDLOJRUTNRJDJO-UHFFFAOYSA-N Valiolamine Natural products NC1CC(O)(CO)C(O)C(O)C1O VDLOJRUTNRJDJO-UHFFFAOYSA-N 0.000 description 1
• 241000700605 Viruses Species 0.000 description 1
• FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical compound OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 description 1
• DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
• FIULGFJIHJJXMT-UHFFFAOYSA-N [C]1[N]C=CC=C1 Chemical class [C]1[N]C=CC=C1 FIULGFJIHJJXMT-UHFFFAOYSA-N 0.000 description 1
• 229960002632 acarbose Drugs 0.000 description 1
• XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 1
• 238000009825 accumulation Methods 0.000 description 1
• XPOLVIIHTDKJRY-UHFFFAOYSA-N acetic acid;methanimidamide Chemical compound NC=N.CC(O)=O XPOLVIIHTDKJRY-UHFFFAOYSA-N 0.000 description 1
• CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
• 108020002494 acetyltransferase Proteins 0.000 description 1
• 102000005421 acetyltransferase Human genes 0.000 description 1
• 239000003377 acid catalyst Substances 0.000 description 1
• 230000003213 activating effect Effects 0.000 description 1
• 230000004913 activation Effects 0.000 description 1
• 239000012190 activator Substances 0.000 description 1
• 238000007259 addition reaction Methods 0.000 description 1
• 108060000200 adenylate cyclase Proteins 0.000 description 1
• 102000030621 adenylate cyclase Human genes 0.000 description 1
• 239000002671 adjuvant Substances 0.000 description 1
• 239000000048 adrenergic agonist Substances 0.000 description 1
• 239000000674 adrenergic antagonist Substances 0.000 description 1
• 229940126157 adrenergic receptor agonist Drugs 0.000 description 1
• 238000013019 agitation Methods 0.000 description 1
• 229950007884 alacepril Drugs 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
• 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
• 150000008046 alkali metal hydrides Chemical class 0.000 description 1
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
• 150000001342 alkaline earth metals Chemical class 0.000 description 1
• ZSBOMTDTBDDKMP-OAHLLOKOSA-N alogliptin Chemical compound C=1C=CC=C(C#N)C=1CN1C(=O)N(C)C(=O)C=C1N1CCC[C@@H](N)C1 ZSBOMTDTBDDKMP-OAHLLOKOSA-N 0.000 description 1
• 102000016679 alpha-Glucosidases Human genes 0.000 description 1
• 108010028144 alpha-Glucosidases Proteins 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
• 150000001413 amino acids Chemical group 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 239000000908 ammonium hydroxide Substances 0.000 description 1
• 239000003708 ampul Substances 0.000 description 1
• 230000006538 anaerobic glycolysis Effects 0.000 description 1
• 239000013011 aqueous formulation Substances 0.000 description 1
• 239000007900 aqueous suspension Substances 0.000 description 1
• 239000008135 aqueous vehicle Substances 0.000 description 1
• 229910052786 argon Inorganic materials 0.000 description 1
• 150000004982 aromatic amines Chemical class 0.000 description 1
• 239000003849 aromatic solvent Substances 0.000 description 1
• 238000007080 aromatic substitution reaction Methods 0.000 description 1
• 229950002927 aronixil Drugs 0.000 description 1
• 235000021311 artificial sweeteners Nutrition 0.000 description 1
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
• 238000003149 assay kit Methods 0.000 description 1
• 239000012298 atmosphere Substances 0.000 description 1
• 229960005370 atorvastatin Drugs 0.000 description 1
• 230000006472 autoimmune response Effects 0.000 description 1
• 210000003403 autonomic nervous system Anatomy 0.000 description 1
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 description 1
• 125000004273 azetidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])C1([H])* 0.000 description 1
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 description 1
• 125000004266 aziridin-1-yl group Chemical group [H]C1([H])N(*)C1([H])[H] 0.000 description 1
• 229950009252 beclobrate Drugs 0.000 description 1
• YWQGBCXVCXMSLJ-UHFFFAOYSA-N beclobrate Chemical compound C1=CC(OC(C)(CC)C(=O)OCC)=CC=C1CC1=CC=C(Cl)C=C1 YWQGBCXVCXMSLJ-UHFFFAOYSA-N 0.000 description 1
• 229960004530 benazepril Drugs 0.000 description 1
• 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• 235000019445 benzyl alcohol Nutrition 0.000 description 1
• 239000003613 bile acid Substances 0.000 description 1
• MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 1
• 108091008324 binding proteins Proteins 0.000 description 1
• BFYRHDVAEJIBON-UHFFFAOYSA-N binifibrate Chemical compound C=1C=CN=CC=1C(=O)OCC(COC(=O)C=1C=NC=CC=1)OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 BFYRHDVAEJIBON-UHFFFAOYSA-N 0.000 description 1
• 229950004495 binifibrate Drugs 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• 230000036983 biotransformation Effects 0.000 description 1
• 210000004204 blood vessel Anatomy 0.000 description 1
• 210000004556 brain Anatomy 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
• 229960004111 buformin Drugs 0.000 description 1
• XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical compound CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 description 1
• SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 description 1
• 229960001058 bupropion Drugs 0.000 description 1
• 229960002495 buspirone Drugs 0.000 description 1
• 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
• 230000001593 cAMP accumulation Effects 0.000 description 1
• 230000011496 cAMP-mediated signaling Effects 0.000 description 1
• 235000019577 caloric intake Nutrition 0.000 description 1
• 201000011510 cancer Diseases 0.000 description 1
• 239000003555 cannabinoid 1 receptor antagonist Substances 0.000 description 1
• 229960000830 captopril Drugs 0.000 description 1
• FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 1
• 230000021235 carbamoylation Effects 0.000 description 1
• 150000001720 carbohydrates Chemical class 0.000 description 1
• 235000014633 carbohydrates Nutrition 0.000 description 1
• 125000004432 carbon atom Chemical group C* 0.000 description 1
• 239000001569 carbon dioxide Substances 0.000 description 1
• 229910002092 carbon dioxide Inorganic materials 0.000 description 1
• 235000011089 carbon dioxide Nutrition 0.000 description 1
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
• 150000001723 carbon free-radicals Chemical class 0.000 description 1
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
• 230000015556 catabolic process Effects 0.000 description 1
• 238000006555 catalytic reaction Methods 0.000 description 1
• 238000010531 catalytic reduction reaction Methods 0.000 description 1
• 230000003915 cell function Effects 0.000 description 1
• 210000000170 cell membrane Anatomy 0.000 description 1
• 230000019522 cellular metabolic process Effects 0.000 description 1
• 230000005754 cellular signaling Effects 0.000 description 1
• 230000002490 cerebral effect Effects 0.000 description 1
• SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 description 1
• 229960005110 cerivastatin Drugs 0.000 description 1
• 229950005749 ceronapril Drugs 0.000 description 1
• 230000008859 change Effects 0.000 description 1
• JUFFVKRROAPVBI-PVOYSMBESA-N chembl1210015 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(=O)N[C@H]1[C@@H]([C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO[C@]3(O[C@@H](C[C@H](O)[C@H](O)CO)[C@H](NC(C)=O)[C@@H](O)C3)C(O)=O)O2)O)[C@@H](CO)O1)NC(C)=O)C(=O)NCC(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 JUFFVKRROAPVBI-PVOYSMBESA-N 0.000 description 1
• SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 1
• 235000013330 chicken meat Nutrition 0.000 description 1
• 239000012320 chlorinating reagent Substances 0.000 description 1
• 238000005660 chlorination reaction Methods 0.000 description 1
• 230000001906 cholesterol absorption Effects 0.000 description 1
• 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 description 1
• 229960005025 cilazapril Drugs 0.000 description 1
• HHHKFGXWKKUNCY-FHWLQOOXSA-N cilazapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N2[C@@H](CCCN2CCC1)C(O)=O)=O)CC1=CC=CC=C1 HHHKFGXWKKUNCY-FHWLQOOXSA-N 0.000 description 1
• 230000001886 ciliary effect Effects 0.000 description 1
• 229950003072 clinofibrate Drugs 0.000 description 1
• 229950008441 clofibric acid Drugs 0.000 description 1
• TXCGAZHTZHNUAI-UHFFFAOYSA-N clofibric acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 TXCGAZHTZHNUAI-UHFFFAOYSA-N 0.000 description 1
• 239000000306 component Substances 0.000 description 1
• 229940125810 compound 20 Drugs 0.000 description 1
• 229940125851 compound 27 Drugs 0.000 description 1
• 238000010276 construction Methods 0.000 description 1
• 230000002596 correlated effect Effects 0.000 description 1
• IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 1
• 229960000258 corticotropin Drugs 0.000 description 1
• 238000004132 cross linking Methods 0.000 description 1
• 239000013058 crude material Substances 0.000 description 1
• 239000012043 crude product Substances 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 238000011461 current therapy Methods 0.000 description 1
• ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
• WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
• 229940095074 cyclic amp Drugs 0.000 description 1
• 125000000392 cycloalkenyl group Chemical group 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 1
• OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical class NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 1
• 230000007547 defect Effects 0.000 description 1
• 238000006731 degradation reaction Methods 0.000 description 1
• FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 description 1
• 229960005227 delapril Drugs 0.000 description 1
• WOUOLAUOZXOLJQ-MBSDFSHPSA-N delapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N(CC(O)=O)C1CC2=CC=CC=C2C1)CC1=CC=CC=C1 WOUOLAUOZXOLJQ-MBSDFSHPSA-N 0.000 description 1
• 230000002939 deleterious effect Effects 0.000 description 1
• 229960004597 dexfenfluramine Drugs 0.000 description 1
• 235000019425 dextrin Nutrition 0.000 description 1
• 238000003745 diagnosis Methods 0.000 description 1
• 125000005432 dialkylcarboxamide group Chemical group 0.000 description 1
• 239000012954 diazonium Substances 0.000 description 1
• 150000001989 diazonium salts Chemical class 0.000 description 1
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
• 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
• 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• 230000004069 differentiation Effects 0.000 description 1
• 230000029087 digestion Effects 0.000 description 1
• 102000038379 digestive enzymes Human genes 0.000 description 1
• 108091007734 digestive enzymes Proteins 0.000 description 1
• POCFBDFTJMJWLG-UHFFFAOYSA-N dihydrosinapic acid methyl ester Natural products COC(=O)CCC1=CC(OC)=C(O)C(OC)=C1 POCFBDFTJMJWLG-UHFFFAOYSA-N 0.000 description 1
• BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• BFMYDTVEBKDAKJ-UHFFFAOYSA-L disodium;(2',7'-dibromo-3',6'-dioxido-3-oxospiro[2-benzofuran-1,9'-xanthene]-4'-yl)mercury;hydrate Chemical compound O.[Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C([O-])C([Hg])=C1OC1=C2C=C(Br)C([O-])=C1 BFMYDTVEBKDAKJ-UHFFFAOYSA-L 0.000 description 1
• 238000006073 displacement reaction Methods 0.000 description 1
• 238000010494 dissociation reaction Methods 0.000 description 1
• 230000005593 dissociations Effects 0.000 description 1
• 239000012153 distilled water Substances 0.000 description 1
• 238000009826 distribution Methods 0.000 description 1
• 229940052760 dopamine agonists Drugs 0.000 description 1
• 239000003136 dopamine receptor stimulating agent Substances 0.000 description 1
• 239000000890 drug combination Substances 0.000 description 1
• 238000012377 drug delivery Methods 0.000 description 1
• 238000009510 drug design Methods 0.000 description 1
• 238000007876 drug discovery Methods 0.000 description 1
• 229940112141 dry powder inhaler Drugs 0.000 description 1
• 239000008157 edible vegetable oil Substances 0.000 description 1
• 229950005925 eflucimibe Drugs 0.000 description 1
• 229910001651 emery Inorganic materials 0.000 description 1
• 229960000873 enalapril Drugs 0.000 description 1
• GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 1
• 229960002680 enalaprilat Drugs 0.000 description 1
• MZYVOFLIPYDBGD-MLZQUWKJSA-N enalaprilat dihydrate Chemical compound O.O.C([C@H](N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 MZYVOFLIPYDBGD-MLZQUWKJSA-N 0.000 description 1
• 229950004732 enazadrem Drugs 0.000 description 1
• 239000006274 endogenous ligand Substances 0.000 description 1
• 229960002179 ephedrine Drugs 0.000 description 1
• 210000002615 epidermis Anatomy 0.000 description 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 229960003501 etofibrate Drugs 0.000 description 1
• XXRVYAFBUDSLJX-UHFFFAOYSA-N etofibrate Chemical compound C=1C=CN=CC=1C(=O)OCCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 XXRVYAFBUDSLJX-UHFFFAOYSA-N 0.000 description 1
• 229950009036 etofylline clofibrate Drugs 0.000 description 1
• KYAKGJDISSNVPZ-UHFFFAOYSA-N etofylline clofibrate Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2N=CN1CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KYAKGJDISSNVPZ-UHFFFAOYSA-N 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 229960001519 exenatide Drugs 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 239000013604 expression vector Substances 0.000 description 1
• 208000030533 eye disease Diseases 0.000 description 1
• 229960001582 fenfluramine Drugs 0.000 description 1
• 230000001605 fetal effect Effects 0.000 description 1
• 239000000945 filler Substances 0.000 description 1
• 238000011049 filling Methods 0.000 description 1
• 125000001153 fluoro group Chemical group F* 0.000 description 1
• 229960003765 fluvastatin Drugs 0.000 description 1
• 239000006260 foam Substances 0.000 description 1
• 239000011888 foil Substances 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 229960002490 fosinopril Drugs 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• 238000004108 freeze drying Methods 0.000 description 1
• 235000019525 fullness Nutrition 0.000 description 1
• 230000004927 fusion Effects 0.000 description 1
• 108020001507 fusion proteins Proteins 0.000 description 1
• 102000037865 fusion proteins Human genes 0.000 description 1
• 208000020694 gallbladder disease Diseases 0.000 description 1
• 230000030136 gastric emptying Effects 0.000 description 1
• 210000001035 gastrointestinal tract Anatomy 0.000 description 1
• 238000003304 gavage Methods 0.000 description 1
• 239000003349 gelling agent Substances 0.000 description 1
• 230000002068 genetic effect Effects 0.000 description 1
• 239000011521 glass Substances 0.000 description 1
• 229960004580 glibenclamide Drugs 0.000 description 1
• WIGIZIANZCJQQY-RUCARUNLSA-N glimepiride Chemical compound O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)C=C1 WIGIZIANZCJQQY-RUCARUNLSA-N 0.000 description 1
• 229960004346 glimepiride Drugs 0.000 description 1
• ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 description 1
• 229960001381 glipizide Drugs 0.000 description 1
• 229960004666 glucagon Drugs 0.000 description 1
• 239000003877 glucagon like peptide 1 receptor agonist Substances 0.000 description 1
• 229940124750 glucocorticoid receptor agonist Drugs 0.000 description 1
• 230000004110 gluconeogenesis Effects 0.000 description 1
• 230000009229 glucose formation Effects 0.000 description 1
• 230000014101 glucose homeostasis Effects 0.000 description 1
• 230000006377 glucose transport Effects 0.000 description 1
• ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
• ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 1
• 108020004445 glyceraldehyde-3-phosphate dehydrogenase Proteins 0.000 description 1
• 235000011187 glycerol Nutrition 0.000 description 1
• 229940096919 glycogen Drugs 0.000 description 1
• 208000035474 group of disease Diseases 0.000 description 1
• JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
• 150000004820 halides Chemical class 0.000 description 1
• 150000008282 halocarbons Chemical class 0.000 description 1
• 125000005843 halogen group Chemical group 0.000 description 1
• 208000019622 heart disease Diseases 0.000 description 1
• 210000003709 heart valve Anatomy 0.000 description 1
• 125000005241 heteroarylamino group Chemical group 0.000 description 1
• 125000005842 heteroatom Chemical group 0.000 description 1
• 229960001340 histamine Drugs 0.000 description 1
• 239000008240 homogeneous mixture Substances 0.000 description 1
• 239000003667 hormone antagonist Substances 0.000 description 1
• 102000055839 human AGRP Human genes 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• 239000001257 hydrogen Substances 0.000 description 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
• DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 1
• 230000003345 hyperglycaemic effect Effects 0.000 description 1
• 230000002218 hypoglycaemic effect Effects 0.000 description 1
• 230000002267 hypothalamic effect Effects 0.000 description 1
• 229960001195 imidapril Drugs 0.000 description 1
• KLZWOWYOHUKJIG-BPUTZDHNSA-N imidapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1C(N(C)C[C@H]1C(O)=O)=O)CC1=CC=CC=C1 KLZWOWYOHUKJIG-BPUTZDHNSA-N 0.000 description 1
• 238000003018 immunoassay Methods 0.000 description 1
• 229950005809 implitapide Drugs 0.000 description 1
• 238000011065 in-situ storage Methods 0.000 description 1
• 239000005414 inactive ingredient Substances 0.000 description 1
• 238000010348 incorporation Methods 0.000 description 1
• 208000015181 infectious disease Diseases 0.000 description 1
• 201000006747 infectious mononucleosis Diseases 0.000 description 1
• 229940102223 injectable solution Drugs 0.000 description 1
• 229940102213 injectable suspension Drugs 0.000 description 1
• 230000010354 integration Effects 0.000 description 1
• 210000000936 intestine Anatomy 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000003874 inverse correlation nuclear magnetic resonance spectroscopy Methods 0.000 description 1
• 235000011073 invertase Nutrition 0.000 description 1
• 238000011835 investigation Methods 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
• 125000005932 isopentyloxycarbonyl group Chemical group 0.000 description 1
• 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
• 239000010410 layer Substances 0.000 description 1
• 239000000787 lecithin Substances 0.000 description 1
• 235000010445 lecithin Nutrition 0.000 description 1
• 229940067606 lecithin Drugs 0.000 description 1
• 229940039781 leptin Drugs 0.000 description 1
• 102000005861 leptin receptors Human genes 0.000 description 1
• 108010019813 leptin receptors Proteins 0.000 description 1
• 230000003902 lesion Effects 0.000 description 1
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
• 229960002701 liraglutide Drugs 0.000 description 1
• 229960002394 lisinopril Drugs 0.000 description 1
• CZRQXSDBMCMPNJ-ZUIPZQNBSA-N lisinopril dihydrate Chemical compound O.O.C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 CZRQXSDBMCMPNJ-ZUIPZQNBSA-N 0.000 description 1
• KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 description 1
• 229960004773 losartan Drugs 0.000 description 1
• PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 1
• 229960004844 lovastatin Drugs 0.000 description 1
• QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
• 239000001095 magnesium carbonate Substances 0.000 description 1
• 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
• 235000014380 magnesium carbonate Nutrition 0.000 description 1
• 230000001071 malnutrition Effects 0.000 description 1
• 235000000824 malnutrition Nutrition 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 239000011159 matrix material Substances 0.000 description 1
• 229960000299 mazindol Drugs 0.000 description 1
• ORRDHOMWDPJSNL-UHFFFAOYSA-N melanin concentrating hormone Chemical compound N1C(=O)C(C(C)C)NC(=O)C(CCCNC(N)=N)NC(=O)CNC(=O)C(C(C)C)NC(=O)C(CCSC)NC(=O)C(NC(=O)C(CCCNC(N)=N)NC(=O)C(NC(=O)C(NC(=O)C(N)CC(O)=O)C(C)O)CCSC)CSSCC(C(=O)NC(CC=2C3=CC=CC=C3NC=2)C(=O)NC(CCC(O)=O)C(=O)NC(C(C)C)C(O)=O)NC(=O)C2CCCN2C(=O)C(CCCNC(N)=N)NC(=O)C1CC1=CC=C(O)C=C1 ORRDHOMWDPJSNL-UHFFFAOYSA-N 0.000 description 1
• QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
• 229910052753 mercury Inorganic materials 0.000 description 1
• 208000030159 metabolic disease Diseases 0.000 description 1
• 229910052751 metal Inorganic materials 0.000 description 1
• 239000002184 metal Substances 0.000 description 1
• XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
• 229960003105 metformin Drugs 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
• 238000007069 methylation reaction Methods 0.000 description 1
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
• 108010038232 microsomal triglyceride transfer protein Proteins 0.000 description 1
• 229960001110 miglitol Drugs 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 235000019426 modified starch Nutrition 0.000 description 1
• 230000009456 molecular mechanism Effects 0.000 description 1
• SLZIZIJTGAYEKK-CIJSCKBQSA-N molport-023-220-247 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)CN)[C@@H](C)O)C1=CNC=N1 SLZIZIJTGAYEKK-CIJSCKBQSA-N 0.000 description 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
• 239000002324 mouth wash Substances 0.000 description 1
• 210000003205 muscle Anatomy 0.000 description 1
• 210000004457 myocytus nodalis Anatomy 0.000 description 1
• DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
• NGNDHNHJYWNRMO-UHFFFAOYSA-N n-(2-methoxyethyl)-6-methyl-5-nitropyridin-2-amine Chemical compound COCCNC1=CC=C([N+]([O-])=O)C(C)=N1 NGNDHNHJYWNRMO-UHFFFAOYSA-N 0.000 description 1
• XCTTVNSXEHWZBI-UHFFFAOYSA-N n-(2-methylpropyl)formamide Chemical compound CC(C)CNC=O XCTTVNSXEHWZBI-UHFFFAOYSA-N 0.000 description 1
• YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 1
• NRMJMIGWXUCEEW-UHFFFAOYSA-N n-butan-2-ylformamide Chemical compound CCC(C)NC=O NRMJMIGWXUCEEW-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
• ZKTLKYRAZWGBDB-UHFFFAOYSA-N n-methyl-n-propan-2-ylformamide Chemical compound CC(C)N(C)C=O ZKTLKYRAZWGBDB-UHFFFAOYSA-N 0.000 description 1
• KVTGAKFJRLBHLU-UHFFFAOYSA-N n-propan-2-ylformamide Chemical compound CC(C)NC=O KVTGAKFJRLBHLU-UHFFFAOYSA-N 0.000 description 1
• PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
• 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
• SUUDTPGCUKBECW-UHFFFAOYSA-N n-propylformamide Chemical compound CCCNC=O SUUDTPGCUKBECW-UHFFFAOYSA-N 0.000 description 1
• SDLAKRCBYGZJRW-UHFFFAOYSA-N n-tert-butylformamide Chemical compound CC(C)(C)NC=O SDLAKRCBYGZJRW-UHFFFAOYSA-N 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 229960000698 nateglinide Drugs 0.000 description 1
• OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 description 1
• 235000021096 natural sweeteners Nutrition 0.000 description 1
• IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
• 125000005933 neopentyloxycarbonyl group Chemical group 0.000 description 1
• 230000008764 nerve damage Effects 0.000 description 1
• 210000000653 nervous system Anatomy 0.000 description 1
• 229940000041 nervous system drug Drugs 0.000 description 1
• PKWDZWYVIHVNKS-UHFFFAOYSA-N netoglitazone Chemical compound FC1=CC=CC=C1COC1=CC=C(C=C(CC2C(NC(=O)S2)=O)C=C2)C2=C1 PKWDZWYVIHVNKS-UHFFFAOYSA-N 0.000 description 1
• 229950001628 netoglitazone Drugs 0.000 description 1
• 230000002981 neuropathic effect Effects 0.000 description 1
• 201000001119 neuropathy Diseases 0.000 description 1
• 230000007823 neuropathy Effects 0.000 description 1
• 230000007935 neutral effect Effects 0.000 description 1
• 229950005171 nicofibrate Drugs 0.000 description 1
• RARQHAFNGNPQCZ-UHFFFAOYSA-N nicofibrate Chemical compound C=1C=CN=CC=1COC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 RARQHAFNGNPQCZ-UHFFFAOYSA-N 0.000 description 1
• 238000006396 nitration reaction Methods 0.000 description 1
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
• 125000004433 nitrogen atom Chemical group N* 0.000 description 1
• 239000002687 nonaqueous vehicle Substances 0.000 description 1
• 229940126569 noradrenaline reuptake inhibitor Drugs 0.000 description 1
• 230000002474 noradrenergic effect Effects 0.000 description 1
• 229940127221 norepinephrine reuptake inhibitor Drugs 0.000 description 1
• 238000010606 normalization Methods 0.000 description 1
• 108020004017 nuclear receptors Proteins 0.000 description 1
• 230000000269 nucleophilic effect Effects 0.000 description 1
• 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
• 239000002773 nucleotide Substances 0.000 description 1
• 125000003729 nucleotide group Chemical group 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 239000006186 oral dosage form Substances 0.000 description 1
• 238000007410 oral glucose tolerance test Methods 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 238000012261 overproduction Methods 0.000 description 1
• 239000007800 oxidant agent Substances 0.000 description 1
• 238000004806 packaging method and process Methods 0.000 description 1
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
• VWMZIGBYZQUQOA-QEEMJVPDSA-N pamaqueside Chemical compound O([C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4C[C@H]5[C@@H]([C@]4(CC(=O)[C@@H]3[C@@]2(C)CC1)C)[C@@H]([C@]1(OC[C@H](C)CC1)O5)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VWMZIGBYZQUQOA-QEEMJVPDSA-N 0.000 description 1
• 229950005482 pamaqueside Drugs 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 239000006072 paste Substances 0.000 description 1
• 235000010603 pastilles Nutrition 0.000 description 1
• 230000001717 pathogenic effect Effects 0.000 description 1
• 230000001575 pathological effect Effects 0.000 description 1
• 230000037361 pathway Effects 0.000 description 1
• 229920001277 pectin Polymers 0.000 description 1
• 239000001814 pectin Substances 0.000 description 1
• 235000010987 pectin Nutrition 0.000 description 1
• WTJYTMCYWSZWQB-UHFFFAOYSA-N pentan-3-yl 4-[5-methoxy-6-[(2-methyl-6-methylsulfonylpyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(CC)CC)CCC1OC1=NC=NC(NC=2C(=NC(=CC=2)S(C)(=O)=O)C)=C1OC WTJYTMCYWSZWQB-UHFFFAOYSA-N 0.000 description 1
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
• 229960002582 perindopril Drugs 0.000 description 1
• IPVQLZZIHOAWMC-QXKUPLGCSA-N perindopril Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 IPVQLZZIHOAWMC-QXKUPLGCSA-N 0.000 description 1
• 210000001428 peripheral nervous system Anatomy 0.000 description 1
• 239000000825 pharmaceutical preparation Substances 0.000 description 1
• 229960003243 phenformin Drugs 0.000 description 1
• ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 1
• 150000002989 phenols Chemical class 0.000 description 1
• 229960003562 phentermine Drugs 0.000 description 1
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
• 229930029653 phosphoenolpyruvate Natural products 0.000 description 1
• DTBNBXWJWCWCIK-UHFFFAOYSA-N phosphoenolpyruvic acid Chemical compound OC(=O)C(=C)OP(O)(O)=O DTBNBXWJWCWCIK-UHFFFAOYSA-N 0.000 description 1
• 150000003904 phospholipids Chemical class 0.000 description 1
• 210000004694 pigment cell Anatomy 0.000 description 1
• 229960005095 pioglitazone Drugs 0.000 description 1
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
• 229950000957 pirifibrate Drugs 0.000 description 1
• YJBIJSVYPHRVCI-UHFFFAOYSA-N pirifibrate Chemical compound C=1C=CC(CO)=NC=1COC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 YJBIJSVYPHRVCI-UHFFFAOYSA-N 0.000 description 1
• VGYFMXBACGZSIL-MCBHFWOFSA-N pitavastatin Chemical compound OC(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 VGYFMXBACGZSIL-MCBHFWOFSA-N 0.000 description 1
• 229960002797 pitavastatin Drugs 0.000 description 1
• 239000002985 plastic film Substances 0.000 description 1
• 229920006255 plastic film Polymers 0.000 description 1
• 229920000075 poly(4-vinylpyridine) Polymers 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 229920001155 polypropylene Polymers 0.000 description 1
• 230000008092 positive effect Effects 0.000 description 1
• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical group [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
• 235000015497 potassium bicarbonate Nutrition 0.000 description 1
• 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
• 239000011736 potassium bicarbonate Substances 0.000 description 1
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
• 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
• 229960003611 pramlintide Drugs 0.000 description 1
• 108010029667 pramlintide Proteins 0.000 description 1
• NRKVKVQDUCJPIZ-MKAGXXMWSA-N pramlintide acetate Chemical compound C([C@@H](C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CS)NC(=O)[C@@H](N)CCCCN)[C@@H](C)O)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 NRKVKVQDUCJPIZ-MKAGXXMWSA-N 0.000 description 1
• 229960002847 prasterone Drugs 0.000 description 1
• 229960002965 pravastatin Drugs 0.000 description 1
• TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
• 238000011533 pre-incubation Methods 0.000 description 1
• 238000002953 preparative HPLC Methods 0.000 description 1
• GCYXWQUSHADNBF-AAEALURTSA-N preproglucagon 78-108 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 GCYXWQUSHADNBF-AAEALURTSA-N 0.000 description 1
• 230000002335 preservative effect Effects 0.000 description 1
• 230000003449 preventive effect Effects 0.000 description 1
• 150000003141 primary amines Chemical class 0.000 description 1
• 230000035755 proliferation Effects 0.000 description 1
• ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
• VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 1
• JGVWWKPOYWTPQE-UHFFFAOYSA-N propan-2-yl 4-[2-(2,5-difluoro-4-propoxyanilino)-3-methoxypyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=C(F)C(OCCC)=CC(F)=C1NC1=NC=CC(OC2CCN(CC2)C(=O)OC(C)C)=C1OC JGVWWKPOYWTPQE-UHFFFAOYSA-N 0.000 description 1
• HHWSIELDHJJXNC-UHFFFAOYSA-N propan-2-yl 4-[2-(2-fluoro-4-methylsulfonylanilino)-3-methoxypyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=CN=C(NC=2C(=CC(=CC=2)S(C)(=O)=O)F)C(OC)=C1OC1CCN(C(=O)OC(C)C)CC1 HHWSIELDHJJXNC-UHFFFAOYSA-N 0.000 description 1
• WEPZUETUYBSYDA-UHFFFAOYSA-N propan-2-yl 4-[2-[2-fluoro-4-(2-methoxyethoxy)anilino]-3-methoxypyridin-4-yl]oxypiperidine-1-carboxylate Chemical compound FC1=CC(OCCOC)=CC=C1NC1=NC=CC(OC2CCN(CC2)C(=O)OC(C)C)=C1OC WEPZUETUYBSYDA-UHFFFAOYSA-N 0.000 description 1
• OPNSPEPBIJIVOS-UHFFFAOYSA-N propan-2-yl 4-[5-methoxy-6-[(2-methyl-6-propan-2-ylsulfanylpyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(SC(C)C)N=C1C OPNSPEPBIJIVOS-UHFFFAOYSA-N 0.000 description 1
• JFUSRSJDFSCPCF-UHFFFAOYSA-N propan-2-yl 4-[5-methoxy-6-[[2-methyl-6-(2-methylsulfonylpropan-2-yl)pyridin-3-yl]amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(C(C)(C)S(C)(=O)=O)N=C1C JFUSRSJDFSCPCF-UHFFFAOYSA-N 0.000 description 1
• QVCLPYCNDGYDGQ-UHFFFAOYSA-N propan-2-yl 4-[6-(2,5-difluoro-4-propoxyanilino)-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=C(F)C(OCCC)=CC(F)=C1NC1=NC=NC(OC2CCN(CC2)C(=O)OC(C)C)=C1OC QVCLPYCNDGYDGQ-UHFFFAOYSA-N 0.000 description 1
• UPEJYTIHLFSCES-UHFFFAOYSA-N propan-2-yl 4-[6-(4-bromo-2-fluorophenoxy)-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC=2C(=CC(Br)=CC=2)F)C(OC)=C1OC1CCN(C(=O)OC(C)C)CC1 UPEJYTIHLFSCES-UHFFFAOYSA-N 0.000 description 1
• ZQPHUXOXAMLPRT-UHFFFAOYSA-N propan-2-yl 4-[6-[(2,6-dimethylpyridin-3-yl)amino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(C)N=C1C ZQPHUXOXAMLPRT-UHFFFAOYSA-N 0.000 description 1
• HQQPWOYIVKQOOI-UHFFFAOYSA-N propan-2-yl 4-[6-[(6-bromo-2-methylpyridin-3-yl)amino]-5-methoxypyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=CN=C(OC2CCN(CC2)C(=O)OC(C)C)C(OC)=C1NC1=CC=C(Br)N=C1C HQQPWOYIVKQOOI-UHFFFAOYSA-N 0.000 description 1
• MTMWVFXQQDPXEB-UHFFFAOYSA-N propan-2-yl 4-[[6-[[6-(hydroxymethyl)-3-methylpyridin-2-yl]amino]-4-methoxy-1h-pyrimidin-4-yl]oxy]piperidine-1-carboxylate Chemical compound C=1C(OC)(OC2CCN(CC2)C(=O)OC(C)C)NC=NC=1NC1=NC(CO)=CC=C1C MTMWVFXQQDPXEB-UHFFFAOYSA-N 0.000 description 1
• 230000000069 prophylactic effect Effects 0.000 description 1
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
• 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
• 230000001681 protective effect Effects 0.000 description 1
• 239000011241 protective layer Substances 0.000 description 1
• 229940076372 protein antagonist Drugs 0.000 description 1
• 230000022558 protein metabolic process Effects 0.000 description 1
• KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 description 1
• 229960003908 pseudoephedrine Drugs 0.000 description 1
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
• 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
• 239000002719 pyrimidine nucleotide Substances 0.000 description 1
• 125000001453 quaternary ammonium group Chemical group 0.000 description 1
• 229960001455 quinapril Drugs 0.000 description 1
• JSDRRTOADPPCHY-HSQYWUDLSA-N quinapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 JSDRRTOADPPCHY-HSQYWUDLSA-N 0.000 description 1
• 229960003401 ramipril Drugs 0.000 description 1
• HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 description 1
• 230000035484 reaction time Effects 0.000 description 1
• 230000009257 reactivity Effects 0.000 description 1
• 238000001525 receptor binding assay Methods 0.000 description 1
• 230000013333 regulation of fatty acid metabolic process Effects 0.000 description 1
• 229960002354 repaglinide Drugs 0.000 description 1
• 239000013557 residual solvent Substances 0.000 description 1
• 239000011347 resin Substances 0.000 description 1
• 229920005989 resin Polymers 0.000 description 1
• 210000001525 retina Anatomy 0.000 description 1
• 230000002207 retinal effect Effects 0.000 description 1
• 230000001177 retroviral effect Effects 0.000 description 1
• 230000006965 reversible inhibition Effects 0.000 description 1
• 238000007363 ring formation reaction Methods 0.000 description 1
• 229960000804 ronifibrate Drugs 0.000 description 1
• AYJVGKWCGIYEAK-UHFFFAOYSA-N ronifibrate Chemical compound C=1C=CN=CC=1C(=O)OCCCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 AYJVGKWCGIYEAK-UHFFFAOYSA-N 0.000 description 1
• 229960004586 rosiglitazone Drugs 0.000 description 1
• 235000019553 satiation Nutrition 0.000 description 1
• 238000012216 screening Methods 0.000 description 1
• 238000007789 sealing Methods 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
• 208000037921 secondary disease Diseases 0.000 description 1
• 230000003248 secreting effect Effects 0.000 description 1
• JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 1
• 230000035945 sensitivity Effects 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 238000013207 serial dilution Methods 0.000 description 1
• 239000003772 serotonin uptake inhibitor Substances 0.000 description 1
• 230000019491 signal transduction Effects 0.000 description 1
• 229960004058 simfibrate Drugs 0.000 description 1
• RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
• 229960002855 simvastatin Drugs 0.000 description 1
• 238000009097 single-agent therapy Methods 0.000 description 1
• MFFMDFFZMYYVKS-SECBINFHSA-N sitagliptin Chemical compound C([C@H](CC(=O)N1CC=2N(C(=NN=2)C(F)(F)F)CC1)N)C1=CC(F)=C(F)C=C1F MFFMDFFZMYYVKS-SECBINFHSA-N 0.000 description 1
• 210000000813 small intestine Anatomy 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 159000000000 sodium salts Chemical class 0.000 description 1
• 229910052938 sodium sulfate Inorganic materials 0.000 description 1
• 235000011152 sodium sulphate Nutrition 0.000 description 1
• SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
• 239000008279 sol Substances 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 229960002909 spirapril Drugs 0.000 description 1
• HRWCVUIFMSZDJS-SZMVWBNQSA-N spirapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2(C1)SCCS2)C(O)=O)CC1=CC=CC=C1 HRWCVUIFMSZDJS-SZMVWBNQSA-N 0.000 description 1
• 108700035424 spirapril Proteins 0.000 description 1
• 230000001954 sterilising effect Effects 0.000 description 1
• 239000012258 stirred mixture Substances 0.000 description 1
• 125000003107 substituted aryl group Chemical group 0.000 description 1
• 239000000758 substrate Substances 0.000 description 1
• 150000008163 sugars Chemical class 0.000 description 1
• 150000003457 sulfones Chemical class 0.000 description 1
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
• 230000006103 sulfonylation Effects 0.000 description 1
• 238000005694 sulfonylation reaction Methods 0.000 description 1
• 239000011593 sulfur Substances 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 238000013268 sustained release Methods 0.000 description 1
• 239000012730 sustained-release form Substances 0.000 description 1
• 229940127230 sympathomimetic drug Drugs 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 239000002278 tabletting lubricant Substances 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 229960004084 temocapril Drugs 0.000 description 1
• FIQOFIRCTOWDOW-BJLQDIEVSA-N temocapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C[C@H](SC1)C=1SC=CC=1)=O)CC1=CC=CC=C1 FIQOFIRCTOWDOW-BJLQDIEVSA-N 0.000 description 1
• PWQLFIKTGRINFF-UHFFFAOYSA-N tert-butyl 4-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)CC1 PWQLFIKTGRINFF-UHFFFAOYSA-N 0.000 description 1
• MWRBWPQBGGARAY-UHFFFAOYSA-M tert-butyl acetate;chlorozinc(1+) Chemical compound [Zn+]Cl.CC(C)(C)OC([CH2-])=O MWRBWPQBGGARAY-UHFFFAOYSA-M 0.000 description 1
• BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
• CXGTZJYQWSUFET-IBGZPJMESA-N tesaglitazar Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=CC=C(OS(C)(=O)=O)C=C1 CXGTZJYQWSUFET-IBGZPJMESA-N 0.000 description 1
• 229950004704 tesaglitazar Drugs 0.000 description 1
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
• CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
• QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 230000008719 thickening Effects 0.000 description 1
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
• 150000003568 thioethers Chemical class 0.000 description 1
• 229960003785 thonzylamine Drugs 0.000 description 1
• 239000003749 thyromimetic agent Substances 0.000 description 1
• 238000003354 tissue distribution assay Methods 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• CMSGWTNRGKRWGS-NQIIRXRSSA-N torcetrapib Chemical compound COC(=O)N([C@H]1C[C@@H](CC)N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CMSGWTNRGKRWGS-NQIIRXRSSA-N 0.000 description 1
• 231100000027 toxicology Toxicity 0.000 description 1
• 229960002051 trandolapril Drugs 0.000 description 1
• 238000013518 transcription Methods 0.000 description 1
• 230000035897 transcription Effects 0.000 description 1
• 238000001890 transfection Methods 0.000 description 1
• 238000012546 transfer Methods 0.000 description 1
• 238000000844 transformation Methods 0.000 description 1
• 230000001052 transient effect Effects 0.000 description 1
• ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 1
• 150000003626 triacylglycerols Chemical class 0.000 description 1
• 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 1
• 229940035893 uracil Drugs 0.000 description 1
• 150000003673 urethanes Chemical class 0.000 description 1
• 210000002700 urine Anatomy 0.000 description 1
• 239000000777 urocortin Substances 0.000 description 1
• SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
• 230000003612 virological effect Effects 0.000 description 1
• 239000011345 viscous material Substances 0.000 description 1
• 229960001729 voglibose Drugs 0.000 description 1
• 102000008396 voltage-gated potassium channel activity proteins Human genes 0.000 description 1
• 108040002559 voltage-gated potassium channel activity proteins Proteins 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 238000005303 weighing Methods 0.000 description 1