CA2420178A1 - Oxazolyl-aryloxyacetic acid derivatives and their use as ppar agonists - Google Patents

Info

Publication number

CA2420178A1

CA2420178A1 CA002420178A CA2420178A CA2420178A1 CA 2420178 A1 CA2420178 A1 CA 2420178A1 CA 002420178 A CA002420178 A CA 002420178A CA 2420178 A CA2420178 A CA 2420178A CA 2420178 A1 CA2420178 A1 CA 2420178A1

Authority

CA

Canada

Prior art keywords

methyl

alkyl

compound

phenoxy

ethoxy

Prior art date

2000-08-23

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 239000000556 agonist Substances 0.000 title description 7
• 229940083759 high-ceiling diuretics aryloxyacetic acid derivative Drugs 0.000 title description 2
• 101150014691 PPARA gene Proteins 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 224
• -1 R2 is H Chemical group 0.000 claims abstract description 77
• 150000003839 salts Chemical class 0.000 claims abstract description 60
• 239000012453 solvate Substances 0.000 claims abstract description 32
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims abstract description 30
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims abstract description 30
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 27
• 238000011282 treatment Methods 0.000 claims abstract description 21
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 20
• 150000004677 hydrates Chemical class 0.000 claims abstract description 16
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 14
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 12
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 5
• 125000004957 naphthylene group Chemical group 0.000 claims abstract description 4
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 3
• 125000003107 substituted aryl group Chemical group 0.000 claims abstract 3
• 238000000034 method Methods 0.000 claims description 107
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 52
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 37
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 31
• 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 30
• 241000124008 Mammalia Species 0.000 claims description 30
• 239000008103 glucose Substances 0.000 claims description 30
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 28
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 28
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 25
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 21
• 125000003118 aryl group Chemical group 0.000 claims description 18
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 102000005962 receptors Human genes 0.000 claims description 16
• 108020003175 receptors Proteins 0.000 claims description 16
• 210000004369 blood Anatomy 0.000 claims description 15
• 239000008280 blood Substances 0.000 claims description 15
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 14
• 210000002966 serum Anatomy 0.000 claims description 14
• 150000003626 triacylglycerols Chemical class 0.000 claims description 14
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 13
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 13
• 235000019260 propionic acid Nutrition 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 208000011580 syndromic disease Diseases 0.000 claims description 9
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 8
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 8
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 8
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• 108010007622 LDL Lipoproteins Proteins 0.000 claims description 7
• 102000007330 LDL Lipoproteins Human genes 0.000 claims description 7
• 125000001624 naphthyl group Chemical group 0.000 claims description 7
• 108010010234 HDL Lipoproteins Proteins 0.000 claims description 6
• 102000015779 HDL Lipoproteins Human genes 0.000 claims description 6
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
• 125000004104 aryloxy group Chemical group 0.000 claims description 4
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
• 239000003814 drug Substances 0.000 claims description 4
• 125000004470 heterocyclooxy group Chemical group 0.000 claims description 4
• VUWCWQJMPHAOGO-UHFFFAOYSA-N 2-[4-[[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methylsulfanyl]-2-propylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CCC)=CC(SCC2=C(OC(=N2)C=2C=CC(=CC=2)C(F)(F)F)C)=C1 VUWCWQJMPHAOGO-UHFFFAOYSA-N 0.000 claims description 3
• NFSZHNDIBOJZMH-UHFFFAOYSA-N 2-[2-(benzylcarbamoyloxymethyl)-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenoxy]-2-methylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=1)=CC=C(OC(C)(C)C(O)=O)C=1COC(=O)NCC1=CC=CC=C1 NFSZHNDIBOJZMH-UHFFFAOYSA-N 0.000 claims description 2
• XIAOXDSZPFFSDG-UHFFFAOYSA-N 2-[2-[(2-fluorophenoxy)methyl]-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenoxy]-2-methylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=1)=CC=C(OC(C)(C)C(O)=O)C=1COC1=CC=CC=C1F XIAOXDSZPFFSDG-UHFFFAOYSA-N 0.000 claims description 2
• FLTAJWFZFOEKPE-UHFFFAOYSA-N 2-[2-[(3-fluorophenoxy)methyl]-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenoxy]-2-methylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=1)=CC=C(OC(C)(C)C(O)=O)C=1COC1=CC=CC(F)=C1 FLTAJWFZFOEKPE-UHFFFAOYSA-N 0.000 claims description 2
• NTVGDUHBPXQEFC-UHFFFAOYSA-N 2-[2-[(4-fluorophenyl)methylcarbamoyloxymethyl]-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenoxy]-2-methylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=1)=CC=C(OC(C)(C)C(O)=O)C=1COC(=O)NCC1=CC=C(F)C=C1 NTVGDUHBPXQEFC-UHFFFAOYSA-N 0.000 claims description 2
• AZFFNZFFAWPVGO-UHFFFAOYSA-N 2-[2-methyl-4-[[5-methyl-2-(4-phenylmethoxyphenyl)-1,3-oxazol-4-yl]methoxy]phenoxy]acetic acid Chemical compound CC=1OC(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=NC=1COC1=CC=C(OCC(O)=O)C(C)=C1 AZFFNZFFAWPVGO-UHFFFAOYSA-N 0.000 claims description 2
• FDXZNRILKJRXFZ-UHFFFAOYSA-N 2-[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methylsulfanyl]-2-propylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CCC)=CC(SCC2=C(OC(=N2)C=2C=CC=CC=2)C)=C1 FDXZNRILKJRXFZ-UHFFFAOYSA-N 0.000 claims description 2
• DKFOBENNWPSTSZ-UHFFFAOYSA-N 2-[4-[2-[2-(4-butoxyphenyl)-5-methyl-1,3-oxazol-4-yl]ethylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound C1=CC(OCCCC)=CC=C1C1=NC(CCSC=2C=C(C)C(OCC(O)=O)=CC=2)=C(C)O1 DKFOBENNWPSTSZ-UHFFFAOYSA-N 0.000 claims description 2
• ICGGAQRMHQTVIJ-UHFFFAOYSA-N 2-[4-[[2-(4-bromophenyl)-5-methyl-1,3-oxazol-4-yl]methylsulfanyl]-2-propylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CCC)=CC(SCC2=C(OC(=N2)C=2C=CC(Br)=CC=2)C)=C1 ICGGAQRMHQTVIJ-UHFFFAOYSA-N 0.000 claims description 2
• ARVAGKAGELVHQW-UHFFFAOYSA-N 2-[4-[[5-methyl-2-(4-phenylmethoxyphenyl)-1,3-oxazol-4-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound CC=1OC(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=NC=1CSC1=CC=C(OCC(O)=O)C=C1 ARVAGKAGELVHQW-UHFFFAOYSA-N 0.000 claims description 2
• OATAPOLIZUPPKP-UHFFFAOYSA-N 2-methyl-2-[2-[(2-methylphenoxy)methyl]-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenoxy]propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=1)=CC=C(OC(C)(C)C(O)=O)C=1COC1=CC=CC=C1C OATAPOLIZUPPKP-UHFFFAOYSA-N 0.000 claims description 2
• PJGRWERWZGEXKL-UHFFFAOYSA-N 2-methyl-2-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-2-(phenylmethoxymethyl)phenoxy]propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=1)=CC=C(OC(C)(C)C(O)=O)C=1COCC1=CC=CC=C1 PJGRWERWZGEXKL-UHFFFAOYSA-N 0.000 claims description 2
• GISUZFBXHMYFBU-UHFFFAOYSA-N 2-methyl-2-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-2-[(2-phenylphenoxy)methyl]phenoxy]propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=1)=CC=C(OC(C)(C)C(O)=O)C=1COC1=CC=CC=C1C1=CC=CC=C1 GISUZFBXHMYFBU-UHFFFAOYSA-N 0.000 claims description 2
• UHUFIBDLDIPUIS-UHFFFAOYSA-N 2-methyl-2-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-2-[(4-phenylphenoxy)methyl]phenoxy]propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=1)=CC=C(OC(C)(C)C(O)=O)C=1COC(C=C1)=CC=C1C1=CC=CC=C1 UHUFIBDLDIPUIS-UHFFFAOYSA-N 0.000 claims description 2
• FDUADOLBLVYJOH-UHFFFAOYSA-N 4-[4-[[4-(carboxymethoxy)-3-methylphenoxy]methyl]-5-methyl-1,3-oxazol-2-yl]benzoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C(O)=O)=NC=1COC1=CC=C(OCC(O)=O)C(C)=C1 FDUADOLBLVYJOH-UHFFFAOYSA-N 0.000 claims description 2
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 11
• 125000004171 alkoxy aryl group Chemical group 0.000 claims 2
• AMTSXQFDEKDAFV-UHFFFAOYSA-N 2-[2-[(4-fluorophenoxy)methyl]-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenoxy]-2-methylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=1)=CC=C(OC(C)(C)C(O)=O)C=1COC1=CC=C(F)C=C1 AMTSXQFDEKDAFV-UHFFFAOYSA-N 0.000 claims 1
• MXSBPMNCHHMWGK-UHFFFAOYSA-N 2-[4-[[5-methyl-2-(4-phenylmethoxyphenyl)-1,3-oxazol-4-yl]methoxy]phenoxy]acetic acid Chemical compound CC=1OC(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=NC=1COC1=CC=C(OCC(O)=O)C=C1 MXSBPMNCHHMWGK-UHFFFAOYSA-N 0.000 claims 1
• UOWSULYBSTUTCV-UHFFFAOYSA-N 2-[4-[[5-methyl-2-(4-phenylmethoxyphenyl)-1,3-oxazol-4-yl]methylsulfanyl]-2-propylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CCC)=CC(SCC2=C(OC(=N2)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)C)=C1 UOWSULYBSTUTCV-UHFFFAOYSA-N 0.000 claims 1
• OAKHWYJZGOULJN-UHFFFAOYSA-N 2-methyl-2-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-2-(propan-2-ylcarbamoyloxymethyl)phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(COC(=O)NC(C)C)=CC(OCCC2=C(OC(=N2)C=2C=CC=CC=2)C)=C1 OAKHWYJZGOULJN-UHFFFAOYSA-N 0.000 claims 1
• 241001367053 Autographa gamma Species 0.000 claims 1
• 238000002560 therapeutic procedure Methods 0.000 claims 1
• 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 abstract 1
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
• 125000004446 heteroarylalkyl group Chemical group 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 294
• 238000005160 1H NMR spectroscopy Methods 0.000 description 220
• 101150041968 CDC13 gene Proteins 0.000 description 218
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 218
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 216
• 235000019439 ethyl acetate Nutrition 0.000 description 134
• 239000000203 mixture Substances 0.000 description 132
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 119
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 118
• 239000000243 solution Substances 0.000 description 96
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 88
• 238000006243 chemical reaction Methods 0.000 description 80
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 80
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 72
• 239000007787 solid Substances 0.000 description 65
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
• 239000012044 organic layer Substances 0.000 description 62
• 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 52
• 239000012267 brine Substances 0.000 description 51
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 51
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
• 239000003921 oil Substances 0.000 description 47
• 235000019198 oils Nutrition 0.000 description 47
• 235000002639 sodium chloride Nutrition 0.000 description 46
• 239000000047 product Substances 0.000 description 45
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 44
• 239000011734 sodium Substances 0.000 description 39
• 239000002904 solvent Substances 0.000 description 39
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 38
• 239000011541 reaction mixture Substances 0.000 description 37
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 36
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
• 229910000024 caesium carbonate Inorganic materials 0.000 description 33
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
• 239000012043 crude product Substances 0.000 description 31
• 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 31
• 239000004480 active ingredient Substances 0.000 description 30
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 29
• 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 28
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 28
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 28
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
• 102000004877 Insulin Human genes 0.000 description 26
• 108090001061 Insulin Proteins 0.000 description 26
• 239000012230 colorless oil Substances 0.000 description 26
• 229940125396 insulin Drugs 0.000 description 26
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
• 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 25
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
• 150000002148 esters Chemical class 0.000 description 23
• 239000002253 acid Substances 0.000 description 22
• 238000004587 chromatography analysis Methods 0.000 description 21
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 20
• 239000001257 hydrogen Substances 0.000 description 20
• 229910052739 hydrogen Inorganic materials 0.000 description 20
• 239000003826 tablet Substances 0.000 description 20
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 18
• 238000003818 flash chromatography Methods 0.000 description 18
• 238000009472 formulation Methods 0.000 description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
• 238000010992 reflux Methods 0.000 description 16
• 241001465754 Metazoa Species 0.000 description 15
• 239000002585 base Substances 0.000 description 15
• 239000002775 capsule Substances 0.000 description 15
• 239000010410 layer Substances 0.000 description 15
• QGNITQXBLBMGSS-UHFFFAOYSA-N 2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethyl 4-methylbenzenesulfonate Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOS(=O)(=O)C1=CC=C(C)C=C1 QGNITQXBLBMGSS-UHFFFAOYSA-N 0.000 description 14
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
• 229910052757 nitrogen Inorganic materials 0.000 description 14
• 239000000706 filtrate Substances 0.000 description 13
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 13
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• VUPMMGFDFRPPDE-UHFFFAOYSA-N ethyl 2-(2-formyl-4-phenylmethoxyphenoxy)-2-methylpropanoate Chemical compound C1=C(C=O)C(OC(C)(C)C(=O)OCC)=CC=C1OCC1=CC=CC=C1 VUPMMGFDFRPPDE-UHFFFAOYSA-N 0.000 description 1
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• WBFTYAULZDFKSM-UHFFFAOYSA-N ethyl 2-[2-(cyclohexylmethyl)-4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenoxy]-2-methylpropanoate Chemical compound C1=C(CC2CCCCC2)C(OC(C)(C)C(=O)OCC)=CC=C1OCCC(=C(O1)C)N=C1C1CCCCC1 WBFTYAULZDFKSM-UHFFFAOYSA-N 0.000 description 1
• FIRJGTMIYGSNNM-UHFFFAOYSA-N ethyl 2-[2-(cyclohexylmethyl)-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenoxy]-2-methylpropanoate Chemical compound C1=C(CC2CCCCC2)C(OC(C)(C)C(=O)OCC)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 FIRJGTMIYGSNNM-UHFFFAOYSA-N 0.000 description 1
• OGASXCFHSHNMBJ-UHFFFAOYSA-N ethyl 2-[2-(cyclohexylmethyl)-4-[2-(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)ethoxy]phenoxy]-2-methylpropanoate Chemical compound C1=C(CC2CCCCC2)C(OC(C)(C)C(=O)OCC)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CS1 OGASXCFHSHNMBJ-UHFFFAOYSA-N 0.000 description 1
• HEVQFWCOZHLOFH-UHFFFAOYSA-N ethyl 2-[2-(cyclohexylmethyl)-4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenoxy]-2-methylpropanoate Chemical compound C1=C(CC2CCCCC2)C(OC(C)(C)C(=O)OCC)=CC=C1OCCC(=C(O1)C)N=C1C(C=1)=CC=CC=1C1=CC=CC=C1 HEVQFWCOZHLOFH-UHFFFAOYSA-N 0.000 description 1
• ZMRYIADDIWMZGC-UHFFFAOYSA-N ethyl 2-[2-(cyclohexylmethyl)-4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenoxy]-2-methylpropanoate Chemical compound C1=C(CC2CCCCC2)C(OC(C)(C)C(=O)OCC)=CC=C1OCCC(=C(O1)C)N=C1C(C=C1)=CC=C1C1=CC=CC=C1 ZMRYIADDIWMZGC-UHFFFAOYSA-N 0.000 description 1
• YJOWVBBKYHAVSG-UHFFFAOYSA-N ethyl 2-[2-[hydroxy(phenyl)methyl]-4-phenylmethoxyphenoxy]-2-methylpropanoate Chemical compound C1=C(C(O)C=2C=CC=CC=2)C(OC(C)(C)C(=O)OCC)=CC=C1OCC1=CC=CC=C1 YJOWVBBKYHAVSG-UHFFFAOYSA-N 0.000 description 1
• NILWRVVXJYFBEM-UHFFFAOYSA-N ethyl 2-[2-[hydroxy(phenyl)methyl]-4-phenylmethoxyphenoxy]-2-methylpropanoate;2-[hydroxy(phenyl)methyl]-4-phenylmethoxyphenol Chemical compound C=1C(OCC=2C=CC=CC=2)=CC=C(O)C=1C(O)C1=CC=CC=C1.C1=C(C(O)C=2C=CC=CC=2)C(OC(C)(C)C(=O)OCC)=CC=C1OCC1=CC=CC=C1 NILWRVVXJYFBEM-UHFFFAOYSA-N 0.000 description 1
• GDHKZOPQWDFBGO-UHFFFAOYSA-N ethyl 2-[2-benzyl-4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenoxy]-2-methylpropanoate Chemical compound C1=C(CC=2C=CC=CC=2)C(OC(C)(C)C(=O)OCC)=CC=C1OCCC(=C(O1)C)N=C1C1CCCCC1 GDHKZOPQWDFBGO-UHFFFAOYSA-N 0.000 description 1
• YENJVUJALXGYDP-UHFFFAOYSA-N ethyl 2-[2-benzyl-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenoxy]-2-methylpropanoate Chemical compound C1=C(CC=2C=CC=CC=2)C(OC(C)(C)C(=O)OCC)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 YENJVUJALXGYDP-UHFFFAOYSA-N 0.000 description 1
• MTHJLLNWYYUJRP-UHFFFAOYSA-N ethyl 2-[2-butyl-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenoxy]-2-methylpropanoate Chemical compound C1=C(OC(C)(C)C(=O)OCC)C(CCCC)=CC(OCCC2=C(OC(=N2)C=2C=CC=CC=2)C)=C1 MTHJLLNWYYUJRP-UHFFFAOYSA-N 0.000 description 1
• DIWYKGQLXJUEEY-UHFFFAOYSA-N ethyl 2-[2-butyl-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenoxy]acetate Chemical compound C1=C(OCC(=O)OCC)C(CCCC)=CC(OCCC2=C(OC(=N2)C=2C=CC=CC=2)C)=C1 DIWYKGQLXJUEEY-UHFFFAOYSA-N 0.000 description 1
• NHPBDDRJRDZDFK-UHFFFAOYSA-N ethyl 2-[2-ethyl-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenoxy]-2-methylpropanoate Chemical compound C1=C(CC)C(OC(C)(C)C(=O)OCC)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 NHPBDDRJRDZDFK-UHFFFAOYSA-N 0.000 description 1
• ZUKNQEJOELYWEQ-UHFFFAOYSA-N ethyl 2-[2-ethyl-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenoxy]acetate Chemical compound C1=C(CC)C(OCC(=O)OCC)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 ZUKNQEJOELYWEQ-UHFFFAOYSA-N 0.000 description 1
• YMLBOFCCHXTIEL-UHFFFAOYSA-N ethyl 2-[3-(cyclohexylmethyl)-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenoxy]-2-methylpropanoate Chemical compound C1CCCCC1CC1=CC(OC(C)(C)C(=O)OCC)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 YMLBOFCCHXTIEL-UHFFFAOYSA-N 0.000 description 1
• MHIPEWOTOPGBOS-UHFFFAOYSA-N ethyl 2-[3-butyl-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenoxy]acetate Chemical compound CCCCC1=CC(OCC(=O)OCC)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 MHIPEWOTOPGBOS-UHFFFAOYSA-N 0.000 description 1
• HPIGEDGPGKCNHM-UHFFFAOYSA-N ethyl 2-[3-ethyl-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenoxy]-2-methylpropanoate Chemical compound CCC1=CC(OC(C)(C)C(=O)OCC)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 HPIGEDGPGKCNHM-UHFFFAOYSA-N 0.000 description 1
• GDHJOVRDAOSSES-UHFFFAOYSA-N ethyl 2-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1OCCC1=C(C)OC(C2CCCCC2)=N1 GDHJOVRDAOSSES-UHFFFAOYSA-N 0.000 description 1
• UKHLMNUDSTWGGJ-UHFFFAOYSA-N ethyl 2-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-2,6-dipropylphenoxy]acetate Chemical compound CCCC1=C(OCC(=O)OCC)C(CCC)=CC(OCCC2=C(OC(=N2)C=2C=CC=CC=2)C)=C1 UKHLMNUDSTWGGJ-UHFFFAOYSA-N 0.000 description 1
• ZZARLOGTXPRLND-UHFFFAOYSA-N ethyl 2-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-2-(5-phenylpentyl)phenoxy]acetate Chemical compound C1=C(CCCCCC=2C=CC=CC=2)C(OCC(=O)OCC)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 ZZARLOGTXPRLND-UHFFFAOYSA-N 0.000 description 1
• SEAPYCDOHKYQGE-UHFFFAOYSA-N ethyl 2-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-2-propylphenoxy]acetate Chemical compound C1=C(OCC(=O)OCC)C(CCC)=CC(OCCC2=C(OC(=N2)C=2C=CC=CC=2)C)=C1 SEAPYCDOHKYQGE-UHFFFAOYSA-N 0.000 description 1
• XJPIYHFJZJOTPX-UHFFFAOYSA-N ethyl 2-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-3-(2-methylpropyl)phenoxy]acetate Chemical compound CC(C)CC1=CC(OCC(=O)OCC)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 XJPIYHFJZJOTPX-UHFFFAOYSA-N 0.000 description 1
• FEMPTJVHFRVENJ-UHFFFAOYSA-N ethyl 2-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-3-(5-phenylpentyl)phenoxy]acetate Chemical compound C=1C=CC=CC=1CCCCCC1=CC(OCC(=O)OCC)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 FEMPTJVHFRVENJ-UHFFFAOYSA-N 0.000 description 1
• DOFLTLIYBCYNRZ-UHFFFAOYSA-N ethyl 2-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenoxy]-3-phenylpropanoate Chemical compound C=1C=C(OCCC2=C(OC(=N2)C=2C=CC=CC=2)C)C=CC=1OC(C(=O)OCC)CC1=CC=CC=C1 DOFLTLIYBCYNRZ-UHFFFAOYSA-N 0.000 description 1
• CVPJINVOQIVHAP-UHFFFAOYSA-N ethyl 2-[4-[2-[2-(3,5-ditert-butyl-4-hydroxyphenyl)-1,3-oxazol-4-yl]ethoxy]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1OCCC1=COC(C=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=N1 CVPJINVOQIVHAP-UHFFFAOYSA-N 0.000 description 1
• MFLUADOEXYJEBW-UHFFFAOYSA-N ethyl 2-[4-[2-[2-(3-ethenylphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1OCCC1=C(C)OC(C=2C=C(C=C)C=CC=2)=N1 MFLUADOEXYJEBW-UHFFFAOYSA-N 0.000 description 1
• WNYIXXVJDBFTMQ-UHFFFAOYSA-N ethyl 2-[4-[2-[2-(3-ethylphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1OCCC1=C(C)OC(C=2C=C(CC)C=CC=2)=N1 WNYIXXVJDBFTMQ-UHFFFAOYSA-N 0.000 description 1
• IWPWIYMVQMPRBT-UHFFFAOYSA-N ethyl 2-[4-[2-[2-(3-ethylphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]phenoxy]-2-methylpropanoate;2-[4-[2-[2-(3-ethylphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]phenoxy]-2-methylpropanoic acid Chemical compound CCC1=CC=CC(C=2OC(C)=C(CCOC=3C=CC(OC(C)(C)C(O)=O)=CC=3)N=2)=C1.C1=CC(OC(C)(C)C(=O)OCC)=CC=C1OCCC1=C(C)OC(C=2C=C(CC)C=CC=2)=N1 IWPWIYMVQMPRBT-UHFFFAOYSA-N 0.000 description 1
• WUNADIXGQXAHTF-UHFFFAOYSA-N ethyl 2-[4-[2-[2-(4-ethylphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1OCCC1=C(C)OC(C=2C=CC(CC)=CC=2)=N1 WUNADIXGQXAHTF-UHFFFAOYSA-N 0.000 description 1
• JXLWMMMLQIKTIX-UHFFFAOYSA-N ethyl 2-[4-[2-[2-(4-ethynylphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1OCCC1=C(C)OC(C=2C=CC(=CC=2)C#C)=N1 JXLWMMMLQIKTIX-UHFFFAOYSA-N 0.000 description 1
• GEAYRWPGAMGEEI-UHFFFAOYSA-N ethyl 2-[5-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]-2-propylphenoxy]-2-methylpropanoate Chemical compound C1=C(OC(C)(C)C(=O)OCC)C(CCC)=CC=C1OCCC1=C(C)OC(C2CCCCC2)=N1 GEAYRWPGAMGEEI-UHFFFAOYSA-N 0.000 description 1
• FIHGITXPNXOCKG-UHFFFAOYSA-N ethyl 2-methyl-2-[2-[(3-methylphenoxy)methyl]-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenoxy]propanoate Chemical compound C1=C(COC=2C=C(C)C=CC=2)C(OC(C)(C)C(=O)OCC)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 FIHGITXPNXOCKG-UHFFFAOYSA-N 0.000 description 1
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