TWI333955B

TWI333955B -

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Publication number: TWI333955B
Authority: TW; Taiwan
Prior art keywords: group; inhibitor; acid; general formula; nmr
Prior art date: 2001-05-30

Application number

TW091111430A

Other languages

English (en)

Chinese (zh)

Inventor

Shiohara Hiroaki

Fujikura Hideki

Fushimi Nobuhiko

Ito Fumiaki

Isaji Masayuki

Original Assignee

Kissei Pharmaceutical

Priority date

2001-05-30

Filing date

2002-05-29

Publication date

2010-12-01

2002-05-29 Application filed by Kissei Pharmaceutical filed Critical Kissei Pharmaceutical

2010-12-01 Application granted granted Critical

2010-12-01 Publication of TWI333955B publication Critical patent/TWI333955B/zh

Links

-1 glucosinolate pyrazole derivative Chemical class 0.000 claims description 135
125000000217 alkyl group Chemical group 0.000 claims description 36
239000008280 blood Substances 0.000 claims description 35
210000004369 blood Anatomy 0.000 claims description 34
206010012601 diabetes mellitus Diseases 0.000 claims description 30
210000003802 sputum Anatomy 0.000 claims description 28
206010036790 Productive cough Diseases 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 27
208000024794 sputum Diseases 0.000 claims description 27
230000002159 abnormal effect Effects 0.000 claims description 25
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
208000002249 Diabetes Complications Diseases 0.000 claims description 18
206010012655 Diabetic complications Diseases 0.000 claims description 18
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
230000002401 inhibitory effect Effects 0.000 claims description 17
239000001301 oxygen Substances 0.000 claims description 17
229910052760 oxygen Inorganic materials 0.000 claims description 17
230000004153 glucose metabolism Effects 0.000 claims description 16
201000010099 disease Diseases 0.000 claims description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 15
201000001421 hyperglycemia Diseases 0.000 claims description 13
208000008589 Obesity Diseases 0.000 claims description 12
235000020824 obesity Nutrition 0.000 claims description 12
208000035150 Hypercholesterolemia Diseases 0.000 claims description 11
125000004429 atom Chemical group 0.000 claims description 10
201000001320 Atherosclerosis Diseases 0.000 claims description 9
230000002265 prevention Effects 0.000 claims description 7
206010030113 Oedema Diseases 0.000 claims description 6
230000003143 atherosclerotic effect Effects 0.000 claims description 6
230000000144 pharmacologic effect Effects 0.000 claims description 6
206010019280 Heart failures Diseases 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
201000005569 Gout Diseases 0.000 claims description 4
201000001431 Hyperuricemia Diseases 0.000 claims description 4
235000012054 meals Nutrition 0.000 claims description 4
125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
125000004383 glucosinolate group Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
241000894007 species Species 0.000 claims description 3
240000006394 Sorghum bicolor Species 0.000 claims description 2
235000011684 Sorghum saccharatum Nutrition 0.000 claims description 2
208000005171 Dysmenorrhea Diseases 0.000 claims 1
206010013935 Dysmenorrhoea Diseases 0.000 claims 1
125000001188 haloalkyl group Chemical group 0.000 claims 1
206010020718 hyperplasia Diseases 0.000 claims 1
239000004615 ingredient Substances 0.000 claims 1
230000003449 preventive effect Effects 0.000 claims 1
229940126585 therapeutic drug Drugs 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 133
239000003112 inhibitor Substances 0.000 description 82
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
239000003814 drug Substances 0.000 description 70
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
229940079593 drug Drugs 0.000 description 62
238000005481 NMR spectroscopy Methods 0.000 description 60
239000002904 solvent Substances 0.000 description 58
238000000034 method Methods 0.000 description 55
238000006243 chemical reaction Methods 0.000 description 49
239000000243 solution Substances 0.000 description 42
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 41
239000003795 chemical substances by application Substances 0.000 description 40
239000002585 base Substances 0.000 description 37
230000005764 inhibitory process Effects 0.000 description 31
239000011541 reaction mixture Substances 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
238000012360 testing method Methods 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 28
230000000694 effects Effects 0.000 description 28
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
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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 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
239000002253 acid Substances 0.000 description 24
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 23
235000019439 ethyl acetate Nutrition 0.000 description 23
239000008103 glucose Substances 0.000 description 23
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
239000000556 agonist Substances 0.000 description 21
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125000003545 alkoxy group Chemical group 0.000 description 19
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 19
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000012442 inert solvent Substances 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
238000010992 reflux Methods 0.000 description 18
230000035484 reaction time Effects 0.000 description 17
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
150000001412 amines Chemical class 0.000 description 15
239000012046 mixed solvent Substances 0.000 description 15
239000007858 starting material Substances 0.000 description 15
239000007791 liquid phase Substances 0.000 description 14
229910052708 sodium Inorganic materials 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
230000009286 beneficial effect Effects 0.000 description 13
125000001424 substituent group Chemical group 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
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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
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
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