TWI523652B - 氘化苄基苯衍生物及使用方法 - Google Patents

Info

Publication number

TWI523652B

TWI523652B TW098123938A TW98123938A TWI523652B TW I523652 B TWI523652 B TW I523652B TW 098123938 A TW098123938 A TW 098123938A TW 98123938 A TW98123938 A TW 98123938A TW I523652 B TWI523652 B TW I523652B

Authority

TW

Taiwan

Prior art keywords

alkyl

group

alkoxy

cycloalkyl

optionally substituted

Prior art date

2008-07-15

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims description 56
• CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 title description 3
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 311
• -1 C 1 -C 4 alkylthio Chemical group 0.000 claims description 213
• 150000001875 compounds Chemical class 0.000 claims description 192
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 188
• 239000000203 mixture Substances 0.000 claims description 152
• 125000000217 alkyl group Chemical group 0.000 claims description 125
• 229910052739 hydrogen Inorganic materials 0.000 claims description 117
• 239000001257 hydrogen Substances 0.000 claims description 115
• 125000003118 aryl group Chemical group 0.000 claims description 111
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 92
• 229910052805 deuterium Inorganic materials 0.000 claims description 68
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 66
• 125000001424 substituent group Chemical group 0.000 claims description 65
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 61
• 238000002360 preparation method Methods 0.000 claims description 59
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 58
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 56
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 53
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 48
• 125000001072 heteroaryl group Chemical group 0.000 claims description 47
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 43
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 43
• 125000005843 halogen group Chemical group 0.000 claims description 43
• 150000003839 salts Chemical class 0.000 claims description 39
• 239000003795 chemical substances by application Substances 0.000 claims description 37
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
• 150000002367 halogens Chemical class 0.000 claims description 35
• 229910052736 halogen Inorganic materials 0.000 claims description 32
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 30
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
• 239000003814 drug Substances 0.000 claims description 28
• 201000010099 disease Diseases 0.000 claims description 26
• 125000004104 aryloxy group Chemical group 0.000 claims description 24
• 229940024606 amino acid Drugs 0.000 claims description 23
• 150000001413 amino acids Chemical class 0.000 claims description 22
• 125000003342 alkenyl group Chemical group 0.000 claims description 20
• 125000000304 alkynyl group Chemical group 0.000 claims description 19
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 19
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 18
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 18
• 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 18
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 18
• 238000011282 treatment Methods 0.000 claims description 18
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 17
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 17
• 150000001412 amines Chemical class 0.000 claims description 16
• 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 16
• 125000001188 haloalkyl group Chemical group 0.000 claims description 16
• 239000011734 sodium Substances 0.000 claims description 16
• 229910052708 sodium Inorganic materials 0.000 claims description 16
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 16
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 15
• 239000003153 chemical reaction reagent Substances 0.000 claims description 15
• 239000012729 immediate-release (IR) formulation Substances 0.000 claims description 15
• 238000010348 incorporation Methods 0.000 claims description 15
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 14
• 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 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 claims description 13
• KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 13
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 12
• 239000000460 chlorine Substances 0.000 claims description 12
• 229910052731 fluorine Inorganic materials 0.000 claims description 12
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 12
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 12
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 12
• 201000001320 Atherosclerosis Diseases 0.000 claims description 11
• 206010007558 Cardiac failure chronic Diseases 0.000 claims description 11
• 208000002249 Diabetes Complications Diseases 0.000 claims description 11
• 239000011737 fluorine Substances 0.000 claims description 11
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 11
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 11
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• 229940124597 therapeutic agent Drugs 0.000 claims description 11
• 206010012655 Diabetic complications Diseases 0.000 claims description 10
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 10
• 230000005764 inhibitory process Effects 0.000 claims description 10
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 10
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 10
• 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 9
• 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 9
• 206010022489 Insulin Resistance Diseases 0.000 claims description 9
• COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 9
• 125000005110 aryl thio group Chemical group 0.000 claims description 9
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 9
• 229910052801 chlorine Inorganic materials 0.000 claims description 9
• 125000005366 cycloalkylthio group Chemical group 0.000 claims description 9
• 239000003937 drug carrier Substances 0.000 claims description 9
• 201000001421 hyperglycemia Diseases 0.000 claims description 9
• 239000003444 phase transfer catalyst Substances 0.000 claims description 9
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 8
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims description 8
• ZNPKAOCQMDJBIK-UHFFFAOYSA-N nitrocyanamide Chemical compound [O-][N+](=O)NC#N ZNPKAOCQMDJBIK-UHFFFAOYSA-N 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• 125000003107 substituted aryl group Chemical group 0.000 claims description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
• 201000001431 Hyperuricemia Diseases 0.000 claims description 7
• 206010030113 Oedema Diseases 0.000 claims description 7
• 229940030600 antihypertensive agent Drugs 0.000 claims description 7
• 239000002220 antihypertensive agent Substances 0.000 claims description 7
• 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 7
• 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 7
• 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 7
• 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 7
• 230000001419 dependent effect Effects 0.000 claims description 7
• 229960004295 valine Drugs 0.000 claims description 7
• 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 6
• 206010020772 Hypertension Diseases 0.000 claims description 6
• 208000001145 Metabolic Syndrome Diseases 0.000 claims description 6
• 208000008589 Obesity Diseases 0.000 claims description 6
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 6
• 239000003472 antidiabetic agent Substances 0.000 claims description 6
• 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 6
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
• 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims description 6
• 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 6
• 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 6
• 201000008980 hyperinsulinism Diseases 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 239000002480 mineral oil Substances 0.000 claims description 6
• 235000010446 mineral oil Nutrition 0.000 claims description 6
• 235000020824 obesity Nutrition 0.000 claims description 6
• 229910052710 silicon Inorganic materials 0.000 claims description 6
• 239000010703 silicon Substances 0.000 claims description 6
• 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 5
• 206010049287 Lipodystrophy acquired Diseases 0.000 claims description 5
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
• 239000000883 anti-obesity agent Substances 0.000 claims description 5
• 229940125710 antiobesity agent Drugs 0.000 claims description 5
• 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 5
• 208000006132 lipodystrophy Diseases 0.000 claims description 5
• 229960005190 phenylalanine Drugs 0.000 claims description 5
• 230000002265 prevention Effects 0.000 claims description 5
• 239000012312 sodium hydride Substances 0.000 claims description 5
• 229910000104 sodium hydride Inorganic materials 0.000 claims description 5
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 4
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
• 229940100389 Sulfonylurea Drugs 0.000 claims description 4
• LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims description 4
• TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims description 4
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
• 229940125708 antidiabetic agent Drugs 0.000 claims description 4
• 239000006185 dispersion Substances 0.000 claims description 4
• 229910052707 ruthenium Inorganic materials 0.000 claims description 4
• 229940116269 uric acid Drugs 0.000 claims description 4
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 3
• 239000007983 Tris buffer Substances 0.000 claims description 3
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
• 229910000420 cerium oxide Inorganic materials 0.000 claims description 3
• GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 3
• BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims description 3
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 3
• 230000009885 systemic effect Effects 0.000 claims description 3
• 150000005621 tetraalkylammonium salts Chemical group 0.000 claims description 3
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 3
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
• 125000002252 acyl group Chemical group 0.000 claims description 2
• 210000004369 blood Anatomy 0.000 claims description 2
• 239000008280 blood Substances 0.000 claims description 2
• 150000003254 radicals Chemical class 0.000 claims description 2
• DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical group CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 7
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
• WBLQOEONNIZSFM-UHFFFAOYSA-N CS(=N)=O Chemical compound CS(=N)=O WBLQOEONNIZSFM-UHFFFAOYSA-N 0.000 claims 1
• 108091006299 SLC2A2 Proteins 0.000 claims 1
• 102000000070 Sodium-Glucose Transport Proteins Human genes 0.000 claims 1
• 108010080361 Sodium-Glucose Transport Proteins Proteins 0.000 claims 1
• 230000002378 acidificating effect Effects 0.000 claims 1
• 150000001336 alkenes Chemical class 0.000 claims 1
• RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 1
• 125000005114 heteroarylalkoxy group Chemical group 0.000 claims 1
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 1
• 229910052712 strontium Inorganic materials 0.000 claims 1
• CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims 1
• 230000000007 visual effect Effects 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 157
• 125000004432 carbon atom Chemical group C* 0.000 description 109
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 74
• 235000019439 ethyl acetate Nutrition 0.000 description 60
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 56
• 239000000243 solution Substances 0.000 description 55
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 50
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 45
• 238000006243 chemical reaction Methods 0.000 description 44
• 125000002947 alkylene group Chemical group 0.000 description 43
• 239000002253 acid Substances 0.000 description 38
• 125000000623 heterocyclic group Chemical group 0.000 description 35
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 32
• KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 30
• 239000002904 solvent Substances 0.000 description 30
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 29
• 239000012267 brine Substances 0.000 description 29
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 29
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
• 239000000651 prodrug Substances 0.000 description 28
• 229940002612 prodrug Drugs 0.000 description 28
• 239000007787 solid Substances 0.000 description 28
• 125000002877 alkyl aryl group Chemical group 0.000 description 27
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 26
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 24
• 238000009472 formulation Methods 0.000 description 24
• 229910052938 sodium sulfate Inorganic materials 0.000 description 24
• 235000011152 sodium sulphate Nutrition 0.000 description 24
• 125000003277 amino group Chemical group 0.000 description 23
• 230000002829 reductive effect Effects 0.000 description 23
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 22
• 125000003545 alkoxy group Chemical group 0.000 description 22
• 239000003643 water by type Substances 0.000 description 22
• 239000002585 base Substances 0.000 description 21
• 235000001014 amino acid Nutrition 0.000 description 20
• 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 20
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 19
• 238000004949 mass spectrometry Methods 0.000 description 19
• 239000003039 volatile agent Substances 0.000 description 19
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
• 238000000132 electrospray ionisation Methods 0.000 description 18
• 229920006395 saturated elastomer Polymers 0.000 description 18
• 238000005160 1H NMR spectroscopy Methods 0.000 description 17
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
• 229910052799 carbon Inorganic materials 0.000 description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 17
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 16
• 235000019253 formic acid Nutrition 0.000 description 16
• 238000004128 high performance liquid chromatography Methods 0.000 description 16
• 239000008194 pharmaceutical composition Substances 0.000 description 16
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
• 125000004429 atom Chemical group 0.000 description 14
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 14
• 239000003112 inhibitor Substances 0.000 description 14
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 14
• 239000012044 organic layer Substances 0.000 description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
• 229940079593 drug Drugs 0.000 description 13
• 239000000725 suspension Substances 0.000 description 13
• 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 12
• 239000008103 glucose Substances 0.000 description 12
• 238000000746 purification Methods 0.000 description 12
• KUZXQXCWRNFIHK-UHFFFAOYSA-N 3,3-diethyldodecane Chemical compound CCCCCCCCCC(CC)(CC)CC KUZXQXCWRNFIHK-UHFFFAOYSA-N 0.000 description 11
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 11
• 150000007513 acids Chemical class 0.000 description 11
• 239000003054 catalyst Substances 0.000 description 11
• 206010012601 diabetes mellitus Diseases 0.000 description 11
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 11
• 239000000543 intermediate Substances 0.000 description 11
• 208000024891 symptom Diseases 0.000 description 11
• 102000004877 Insulin Human genes 0.000 description 10
• 108090001061 Insulin Proteins 0.000 description 10
• 239000013078 crystal Substances 0.000 description 10
• 238000007429 general method Methods 0.000 description 10
• 229940125396 insulin Drugs 0.000 description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
• 239000012074 organic phase Substances 0.000 description 10
• 239000003208 petroleum Substances 0.000 description 10
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