TWI405575B - 苄基醣苷衍生物及其使用方法 - Google Patents

Info

Publication number

TWI405575B

TWI405575B TW097112029A TW97112029A TWI405575B TW I405575 B TWI405575 B TW I405575B TW 097112029 A TW097112029 A TW 097112029A TW 97112029 A TW97112029 A TW 97112029A TW I405575 B TWI405575 B TW I405575B

Authority

TW

Taiwan

Prior art keywords

chloro

tetrahydro

phenyl

pyran

triol

Prior art date

2007-04-02

Links

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• Global Dossier
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• -1 Benzylic glycoside Chemical class 0.000 title claims description 130
• 238000000034 method Methods 0.000 title abstract description 84
• 229930182470 glycoside Natural products 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 248
• 239000003814 drug Substances 0.000 claims abstract description 33
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
• 229940124597 therapeutic agent Drugs 0.000 claims abstract description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 62
• 125000000217 alkyl group Chemical group 0.000 claims description 43
• 229910052760 oxygen Inorganic materials 0.000 claims description 40
• 125000001424 substituent group Chemical group 0.000 claims description 37
• 229910052717 sulfur Chemical group 0.000 claims description 32
• 239000003795 chemical substances by application Substances 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 29
• 150000003839 salts Chemical class 0.000 claims description 28
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 24
• 125000003342 alkenyl group Chemical group 0.000 claims description 23
• 239000001257 hydrogen Substances 0.000 claims description 23
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 23
• 239000001301 oxygen Substances 0.000 claims description 23
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 22
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 22
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 20
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 20
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 20
• 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 18
• 125000000304 alkynyl group Chemical group 0.000 claims description 17
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
• 239000011593 sulfur Chemical group 0.000 claims description 14
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 8
• 201000001320 Atherosclerosis Diseases 0.000 claims description 8
• 206010007558 Cardiac failure chronic Diseases 0.000 claims description 8
• LXRBEMFSANYZLV-RTJMFUJLSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-5-[(4-ethylphenyl)methyl]-2-(2-prop-2-enoxyethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(CCOCC=C)C=C1Cl LXRBEMFSANYZLV-RTJMFUJLSA-N 0.000 claims description 7
• 208000002249 Diabetes Complications Diseases 0.000 claims description 7
• 206010012655 Diabetic complications Diseases 0.000 claims description 7
• 206010022489 Insulin Resistance Diseases 0.000 claims description 7
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 7
• 125000001475 halogen functional group Chemical group 0.000 claims description 7
• 201000001421 hyperglycemia Diseases 0.000 claims description 7
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 6
• 239000003472 antidiabetic agent Substances 0.000 claims description 6
• 229940030600 antihypertensive agent Drugs 0.000 claims description 6
• 239000002220 antihypertensive agent Substances 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• DMHDNNYWKKEIJY-RTJMFUJLSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-5-[(4-ethylphenyl)methyl]-2-(2-prop-2-ynoxyethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(CCOCC#C)C=C1Cl DMHDNNYWKKEIJY-RTJMFUJLSA-N 0.000 claims description 5
• 201000001431 Hyperuricemia Diseases 0.000 claims description 5
• 206010030113 Oedema Diseases 0.000 claims description 5
• VMTQLXPABLZMOL-SEFGFODJSA-N (2s,3r,4r,5s,6r)-2-[2-(2-but-2-ynoxyethoxy)-4-chloro-5-[(4-ethylphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(OCCOCC#CC)C=C1Cl VMTQLXPABLZMOL-SEFGFODJSA-N 0.000 claims description 4
• PPVMZZYRTYKVLS-RTJMFUJLSA-N (2s,3r,4r,5s,6r)-2-[2-(but-2-ynoxymethyl)-4-chloro-5-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(OCC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(COCC#CC)C=C1Cl PPVMZZYRTYKVLS-RTJMFUJLSA-N 0.000 claims description 4
• YJUVSHGSPXQZGE-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[2-(but-2-ynoxymethyl)-4-chloro-5-[(4-hydroxyphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=C([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C(COCC#CC)=CC(Cl)=C1CC1=CC=C(O)C=C1 YJUVSHGSPXQZGE-SJSRKZJXSA-N 0.000 claims description 4
• VFAWNKZMKYABHU-RXFVIIJJSA-N (2s,3r,4r,5s,6r)-2-[2-(but-2-ynoxymethyl)-4-chloro-5-[(4-methoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(OC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(COCC#CC)C=C1Cl VFAWNKZMKYABHU-RXFVIIJJSA-N 0.000 claims description 4
• DGGZVTOTLFJBFE-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-2-(2,2-difluoropropoxymethyl)-5-[(4-ethylphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(COCC(C)(F)F)C=C1Cl DGGZVTOTLFJBFE-SJSRKZJXSA-N 0.000 claims description 4
• DMZMZZPXFAVPED-HFBCXCLPSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-2-[2-(2,2-difluoroethoxy)ethyl]-5-[(4-ethylphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(CCOCC(F)F)C=C1Cl DMZMZZPXFAVPED-HFBCXCLPSA-N 0.000 claims description 4
• UIWPNULITLPLPU-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-5-[(4-ethylphenyl)methyl]-2-(2-fluoroethoxymethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(COCCF)C=C1Cl UIWPNULITLPLPU-SJSRKZJXSA-N 0.000 claims description 4
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 4
• 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 4
• 206010020772 Hypertension Diseases 0.000 claims description 4
• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 4
• 208000001145 Metabolic Syndrome Diseases 0.000 claims description 4
• 208000008589 Obesity Diseases 0.000 claims description 4
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 4
• 239000000883 anti-obesity agent Substances 0.000 claims description 4
• 229940125708 antidiabetic agent Drugs 0.000 claims description 4
• 229940125710 antiobesity agent Drugs 0.000 claims description 4
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
• 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 4
• 201000008980 hyperinsulinism Diseases 0.000 claims description 4
• 150000004702 methyl esters Chemical class 0.000 claims description 4
• 235000020824 obesity Nutrition 0.000 claims description 4
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
• AGYXXIHBHOZKHJ-RXFVIIJJSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-5-[(4-ethylphenyl)methyl]-2-(3-hydroxypropoxymethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(COCCCO)C=C1Cl AGYXXIHBHOZKHJ-RXFVIIJJSA-N 0.000 claims description 3
• BSYJXNHJSRKQFL-RXFVIIJJSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-5-[(4-ethylphenyl)methyl]-2-[2-(2-fluoroethoxy)ethyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(CCOCCF)C=C1Cl BSYJXNHJSRKQFL-RXFVIIJJSA-N 0.000 claims description 3
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
• 229920002554 vinyl polymer Polymers 0.000 claims description 3
• PUXBIQNREQEAEK-ZXGKGEBGSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-2-(2,2-difluoroethoxymethyl)-5-[(4-ethylphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(COCC(F)F)C=C1Cl PUXBIQNREQEAEK-ZXGKGEBGSA-N 0.000 claims description 2
• VMKXALKMLJJDTP-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-5-[(4-ethylphenyl)methyl]-2-(2-hydroxyethoxymethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(COCCO)C=C1Cl VMKXALKMLJJDTP-SJSRKZJXSA-N 0.000 claims description 2
• JAAKCPJMYZNUIK-RXFVIIJJSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-5-[(4-ethylphenyl)methyl]-2-(2-methoxyethoxymethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(COCCOC)C=C1Cl JAAKCPJMYZNUIK-RXFVIIJJSA-N 0.000 claims description 2
• MPCAJMNYNOGXPB-UHFFFAOYSA-N 1,5-anhydrohexitol Chemical compound OCC1OCC(O)C(O)C1O MPCAJMNYNOGXPB-UHFFFAOYSA-N 0.000 claims description 2
• 239000003524 antilipemic agent Substances 0.000 claims description 2
• YCPICDNLSPCVHC-RXFVIIJJSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-5-[(4-ethylphenyl)methyl]-2-(prop-2-enoxymethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(COCC=C)C=C1Cl YCPICDNLSPCVHC-RXFVIIJJSA-N 0.000 claims 2
• BLNCUDTURUMUKI-SJSRKZJXSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-5-[(4-ethylphenyl)methyl]-2-[2-(2,2,2-trifluoroethoxy)ethoxy]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(OCCOCC(F)(F)F)C=C1Cl BLNCUDTURUMUKI-SJSRKZJXSA-N 0.000 claims 2
• 125000005133 alkynyloxy group Chemical group 0.000 claims 2
• AAJUQYIPSFNMRY-RTJMFUJLSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-5-[(4-ethylphenyl)methyl]-2-(2-prop-2-ynoxyethoxy)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(OCCOCC#C)C=C1Cl AAJUQYIPSFNMRY-RTJMFUJLSA-N 0.000 claims 1
• BMSFQOYZPHCHRM-IGBUEQETSA-N (2s,3r,4r,5s,6r)-2-[4-chloro-5-[(4-ethylphenyl)methyl]-2-[(2-hydroxy-3-methoxypropoxy)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1=CC(CC)=CC=C1CC1=CC([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C(COCC(O)COC)C=C1Cl BMSFQOYZPHCHRM-IGBUEQETSA-N 0.000 claims 1
• XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims 1
• 229940127557 pharmaceutical product Drugs 0.000 claims 1
• 239000000543 intermediate Substances 0.000 abstract description 121
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 25
• 201000010099 disease Diseases 0.000 abstract description 22
• 230000005764 inhibitory process Effects 0.000 abstract description 8
• 230000002401 inhibitory effect Effects 0.000 abstract description 6
• 102100037202 Sodium/myo-inositol cotransporter 2 Human genes 0.000 abstract description 3
• 101710090560 Sodium/myo-inositol cotransporter 2 Proteins 0.000 abstract description 3
• 102000000070 Sodium-Glucose Transport Proteins Human genes 0.000 abstract 2
• 108010080361 Sodium-Glucose Transport Proteins Proteins 0.000 abstract 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 149
• 238000002360 preparation method Methods 0.000 description 118
• 239000000203 mixture Substances 0.000 description 106
• 239000000243 solution Substances 0.000 description 104
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
• 238000005160 1H NMR spectroscopy Methods 0.000 description 70
• 235000019439 ethyl acetate Nutrition 0.000 description 67
• 239000011734 sodium Substances 0.000 description 57
• 238000006243 chemical reaction Methods 0.000 description 55
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
• 239000012267 brine Substances 0.000 description 47
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 47
• 239000000460 chlorine Substances 0.000 description 45
• 238000003756 stirring Methods 0.000 description 40
• 239000007983 Tris buffer Substances 0.000 description 36
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
• 239000011541 reaction mixture Substances 0.000 description 34
• 238000009472 formulation Methods 0.000 description 32
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 31
• 125000005843 halogen group Chemical group 0.000 description 30
• 125000000392 cycloalkenyl group Chemical group 0.000 description 29
• 239000012044 organic layer Substances 0.000 description 27
• 229940002612 prodrug Drugs 0.000 description 26
• 239000000651 prodrug Substances 0.000 description 26
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 24
• 150000002576 ketones Chemical class 0.000 description 24
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
• 239000003153 chemical reaction reagent Substances 0.000 description 21
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 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
• 238000012746 preparative thin layer chromatography Methods 0.000 description 20
• 229920006395 saturated elastomer Polymers 0.000 description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 19
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• 125000003118 aryl group Chemical group 0.000 description 18
• 229940079593 drug Drugs 0.000 description 17
• 150000002431 hydrogen Chemical group 0.000 description 17
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 16
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 15
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
• 239000012043 crude product Substances 0.000 description 15
• 150000002148 esters Chemical class 0.000 description 15
• 239000003112 inhibitor Substances 0.000 description 15
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 14
• 239000002253 acid Substances 0.000 description 14
• 150000001299 aldehydes Chemical class 0.000 description 14
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 14
• 210000004027 cell Anatomy 0.000 description 14
• 125000004093 cyano group Chemical group *C#N 0.000 description 14
• 239000007787 solid Substances 0.000 description 14
• 229910052801 chlorine Inorganic materials 0.000 description 13
• CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 13
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 238000010521 absorption reaction Methods 0.000 description 12
• 125000001072 heteroaryl group Chemical group 0.000 description 12
• 230000002829 reductive effect Effects 0.000 description 12
• 239000000725 suspension Substances 0.000 description 12
• ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 12
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 11
• 239000004698 Polyethylene Substances 0.000 description 11
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 10
• 102000004877 Insulin Human genes 0.000 description 10
• 108090001061 Insulin Proteins 0.000 description 10
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 10
• 239000003638 chemical reducing agent Substances 0.000 description 10
• 229940125396 insulin Drugs 0.000 description 10
• 150000002596 lactones Chemical class 0.000 description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 10
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