BRPI0313290B1 - derivados de pirazol, promedicamento, composição farmacêutica, agentes terapêuticos e uso medicinal - Google Patents

Info

Publication number

BRPI0313290B1

BRPI0313290B1 BRPI0313290A BR0313290A BRPI0313290B1 BR PI0313290 B1 BRPI0313290 B1 BR PI0313290B1 BR PI0313290 A BRPI0313290 A BR PI0313290A BR 0313290 A BR0313290 A BR 0313290A BR PI0313290 B1 BRPI0313290 B1 BR PI0313290B1

Authority

BR

Brazil

Prior art keywords

group

alkyl

methyl

pyrazole

isopropyl

Prior art date

2002-08-08

Links

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• Global Dossier
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• 150000003217 pyrazoles Chemical class 0.000 title claims abstract description 71
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 20
• 239000003814 drug Substances 0.000 title description 20
• 229940124597 therapeutic agent Drugs 0.000 title 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 209
• 125000005843 halogen group Chemical group 0.000 claims abstract description 78
• 150000003839 salts Chemical class 0.000 claims abstract description 72
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 45
• 208000002249 Diabetes Complications Diseases 0.000 claims abstract description 25
• 206010012655 Diabetic complications Diseases 0.000 claims abstract description 25
• 239000003795 chemical substances by application Substances 0.000 claims abstract description 25
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 21
• 201000010099 disease Diseases 0.000 claims abstract description 19
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
• 230000002265 prevention Effects 0.000 claims abstract description 17
• 208000008589 Obesity Diseases 0.000 claims abstract description 15
• 201000001421 hyperglycemia Diseases 0.000 claims abstract description 15
• 235000020824 obesity Nutrition 0.000 claims abstract description 15
• 101000716688 Homo sapiens Sodium/glucose cotransporter 1 Proteins 0.000 claims abstract description 11
• 102000052194 human SLC5A1 Human genes 0.000 claims abstract description 11
• 238000004519 manufacturing process Methods 0.000 claims abstract description 11
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract description 8
• -1 4- {3- [1-carbamoyl-1- (methyl) ethylcarbamoyl] propyl} -2 -methylphenyl Chemical group 0.000 claims description 259
• 150000001875 compounds Chemical class 0.000 claims description 240
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 186
• 239000000203 mixture Substances 0.000 claims description 176
• 125000001424 substituent group Chemical group 0.000 claims description 103
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 85
• 125000003277 amino group Chemical group 0.000 claims description 82
• 239000003112 inhibitor Substances 0.000 claims description 75
• 125000006239 protecting group Chemical group 0.000 claims description 72
• 125000000217 alkyl group Chemical group 0.000 claims description 66
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 54
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 46
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 40
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 37
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 33
• 125000003118 aryl group Chemical group 0.000 claims description 30
• 208000002705 Glucose Intolerance Diseases 0.000 claims description 29
• 201000009104 prediabetes syndrome Diseases 0.000 claims description 29
• 125000004122 cyclic group Chemical group 0.000 claims description 27
• 229910052757 nitrogen Inorganic materials 0.000 claims description 23
• 125000003545 alkoxy group Chemical group 0.000 claims description 22
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
• 239000001257 hydrogen Substances 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 20
• 125000002252 acyl group Chemical group 0.000 claims description 19
• NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical group NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 18
• 239000008280 blood Substances 0.000 claims description 17
• 210000004369 blood Anatomy 0.000 claims description 17
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 17
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 15
• 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 15
• 239000004480 active ingredient Substances 0.000 claims description 15
• 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 15
• 201000008980 hyperinsulinism Diseases 0.000 claims description 15
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 15
• 125000004755 (C2-C7) acylamino group Chemical group 0.000 claims description 14
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 14
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 14
• 208000035150 Hypercholesterolemia Diseases 0.000 claims description 13
• 206010020772 Hypertension Diseases 0.000 claims description 13
• 125000001072 heteroaryl group Chemical group 0.000 claims description 13
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 12
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
• 208000006575 hypertriglyceridemia Diseases 0.000 claims description 12
• 201000001320 Atherosclerosis Diseases 0.000 claims description 11
• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 11
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
• 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 9
• 229930182830 galactose Natural products 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
• 206010019280 Heart failures Diseases 0.000 claims description 8
• 206010030113 Oedema Diseases 0.000 claims description 8
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 8
• 230000001965 increasing effect Effects 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 125000004434 sulfur atom Chemical group 0.000 claims description 8
• 206010007559 Cardiac failure congestive Diseases 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
• 239000002552 dosage form Substances 0.000 claims description 7
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 7
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
• 201000005569 Gout Diseases 0.000 claims description 6
• 102220480121 H/ACA ribonucleoprotein complex subunit DKC1_R10A_mutation Human genes 0.000 claims description 6
• 201000001431 Hyperuricemia Diseases 0.000 claims description 6
• 238000009472 formulation Methods 0.000 claims description 6
• 230000005764 inhibitory process Effects 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 5
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• 238000013268 sustained release Methods 0.000 claims description 5
• 239000012730 sustained-release form Substances 0.000 claims description 5
• 125000004442 acylamino group Chemical group 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• SLFGPZFFRXPSGJ-DGCZVPQQSA-N n-(2-methyl-1-oxo-1-piperazin-1-ylpropan-2-yl)-4-[3-methyl-4-[[5-propan-2-yl-3-[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1h-pyrazol-4-yl]methyl]phenoxy]butanamide Chemical compound C=1C=C(OCCCC(=O)NC(C)(C)C(=O)N2CCNCC2)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O SLFGPZFFRXPSGJ-DGCZVPQQSA-N 0.000 claims description 4
• HBIYXFQECAHKTC-XQKZFRNSSA-N n-[1-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methyl-1-oxopropan-2-yl]-4-[4-[[5-propan-2-yl-3-[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1h-pyrazol-4-yl]methyl]phenyl]butanamide Chemical compound C=1C=C(CCCC(=O)NC(C)(C)C(=O)N2CCN(CCO)CC2)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O HBIYXFQECAHKTC-XQKZFRNSSA-N 0.000 claims description 4
• ZTHUHHPGJARBOR-DGCZVPQQSA-N n-[2-methyl-1-(4-methylpiperazin-1-yl)-1-oxopropan-2-yl]-4-[4-[[5-propan-2-yl-3-[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1h-pyrazol-4-yl]methyl]phenyl]butanamide Chemical compound C=1C=C(CCCC(=O)NC(C)(C)C(=O)N2CCN(C)CC2)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O ZTHUHHPGJARBOR-DGCZVPQQSA-N 0.000 claims description 4
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
• 125000006411 1-propenylene group Chemical group [H]\C(*)=C(\[H])C([H])([H])[H] 0.000 claims description 3
• TVPOHRFWFNFNHO-HUSNPGIHSA-N 4-[3-fluoro-4-[[5-propan-2-yl-3-[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1h-pyrazol-4-yl]methyl]phenyl]-n-(2-methyl-1-oxo-1-piperazin-1-ylpropan-2-yl)butanamide Chemical compound C=1C=C(CCCC(=O)NC(C)(C)C(=O)N2CCNCC2)C=C(F)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O TVPOHRFWFNFNHO-HUSNPGIHSA-N 0.000 claims description 3
• 208000027472 Galactosemias Diseases 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
• OCGGCRSVZRQNGB-ACMFEJKRSA-N n-(2-aminoethyl)-2-methyl-2-[4-[4-[[5-propan-2-yl-3-[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1h-pyrazol-4-yl]methyl]phenyl]butanoylamino]propanamide Chemical compound C=1C=C(CCCC(=O)NC(C)(C)C(=O)NCCN)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O OCGGCRSVZRQNGB-ACMFEJKRSA-N 0.000 claims description 2
• QEWADZLDPQYPMV-HUSNPGIHSA-N n-[2-(dimethylamino)ethyl]-2-methyl-2-[4-[4-[[5-propan-2-yl-3-[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1h-pyrazol-4-yl]methyl]phenyl]butanoylamino]propanamide Chemical compound C=1C=C(CCCC(=O)NC(C)(C)C(=O)NCCN(C)C)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O QEWADZLDPQYPMV-HUSNPGIHSA-N 0.000 claims description 2
• 230000000063 preceeding effect Effects 0.000 claims description 2
• NHVAFAOXBNJXQN-KNGUAOONSA-N 4-[4-[[1-(3-hydroxypropyl)-5-propan-2-yl-3-[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypyrazol-4-yl]methyl]phenyl]-n-(2-methyl-1-oxo-1-piperazin-1-ylpropan-2-yl)butanamide Chemical compound O([C@H]1[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O1)O)C1=NN(CCCO)C(C(C)C)=C1CC(C=C1)=CC=C1CCCC(=O)NC(C)(C)C(=O)N1CCNCC1 NHVAFAOXBNJXQN-KNGUAOONSA-N 0.000 claims 1
• 206010056997 Impaired fasting glucose Diseases 0.000 claims 1
• 239000004615 ingredient Substances 0.000 claims 1
• 239000000543 intermediate Substances 0.000 abstract description 4
• 239000000651 prodrug Substances 0.000 abstract 1
• 229940002612 prodrug Drugs 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 163
• 239000002904 solvent Substances 0.000 description 127
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 116
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 108
• 239000000243 solution Substances 0.000 description 100
• 238000005160 1H NMR spectroscopy Methods 0.000 description 96
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 94
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 88
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 87
• 230000002829 reductive effect Effects 0.000 description 84
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 76
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 68
• 238000006243 chemical reaction Methods 0.000 description 68
• 239000011541 reaction mixture Substances 0.000 description 63
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 56
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
• 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 49
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 49
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 43
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
• 238000001914 filtration Methods 0.000 description 40
• 238000000034 method Methods 0.000 description 40
• 239000003623 enhancer Substances 0.000 description 36
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
• 239000002198 insoluble material Substances 0.000 description 35
• 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 description 34
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 34
• 239000008103 glucose Substances 0.000 description 34
• WKNMKGVLOWGGOU-UHFFFAOYSA-N 2-aminoacetamide;hydron;chloride Chemical compound Cl.NCC(N)=O WKNMKGVLOWGGOU-UHFFFAOYSA-N 0.000 description 32
• 230000008569 process Effects 0.000 description 32
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 31
• 102000036770 Islet Amyloid Polypeptide Human genes 0.000 description 31
• 108010041872 Islet Amyloid Polypeptide Proteins 0.000 description 31
• 239000000706 filtrate Substances 0.000 description 31
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
• 239000012267 brine Substances 0.000 description 30
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 30
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 29
• 239000000556 agonist Substances 0.000 description 28
• 239000003480 eluent Substances 0.000 description 28
• 239000012442 inert solvent Substances 0.000 description 28
• ZIOBGZDFMKCKGZ-UHFFFAOYSA-N 2-amino-2-methylpropanamide Chemical compound CC(C)(N)C(N)=O ZIOBGZDFMKCKGZ-UHFFFAOYSA-N 0.000 description 26
• 238000010992 reflux Methods 0.000 description 26
• 239000007858 starting material Substances 0.000 description 26
• 239000000843 powder Substances 0.000 description 25
• 230000035484 reaction time Effects 0.000 description 25
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 23
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
• 239000000463 material Substances 0.000 description 23
• 239000012074 organic phase Substances 0.000 description 23
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 22
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 21
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 21
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 20
• 239000002253 acid Substances 0.000 description 20
• WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 19
• 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 19
• 108090001061 Insulin Proteins 0.000 description 19
• 102000004877 Insulin Human genes 0.000 description 19
• 229940125396 insulin Drugs 0.000 description 19
• 108010038512 Platelet-Derived Growth Factor Proteins 0.000 description 18
• 102000010780 Platelet-Derived Growth Factor Human genes 0.000 description 18
• 238000010521 absorption reaction Methods 0.000 description 18
• 239000000284 extract Substances 0.000 description 18
• 239000012298 atmosphere Substances 0.000 description 17
• 238000010898 silica gel chromatography Methods 0.000 description 17
• DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 16
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