TWI298071B - - Google Patents

Info

Publication number

TWI298071B

TWI298071B TW092123126A TW92123126A TWI298071B TW I298071 B TWI298071 B TW I298071B TW 092123126 A TW092123126 A TW 092123126A TW 92123126 A TW92123126 A TW 92123126A TW I298071 B TWI298071 B TW I298071B

Authority

TW

Taiwan

Prior art keywords

group

alkyl

amine

substituent

inhibitor

Prior art date

2002-08-23

Links

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• 125000000217 alkyl group Chemical group 0.000 claims description 214
• 150000001875 compounds Chemical class 0.000 claims description 212
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 182
• -1 acridineyl Chemical group 0.000 claims description 158
• 125000003277 amino group Chemical group 0.000 claims description 143
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 139
• 125000001424 substituent group Chemical group 0.000 claims description 135
• 239000003814 drug Substances 0.000 claims description 103
• 150000003839 salts Chemical class 0.000 claims description 99
• 229940079593 drug Drugs 0.000 claims description 89
• 125000003545 alkoxy group Chemical group 0.000 claims description 84
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 68
• 239000003112 inhibitor Substances 0.000 claims description 65
• 239000001301 oxygen Substances 0.000 claims description 62
• 229910052760 oxygen Inorganic materials 0.000 claims description 62
• 206010012601 diabetes mellitus Diseases 0.000 claims description 52
• 125000003118 aryl group Chemical group 0.000 claims description 50
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 49
• 239000003795 chemical substances by application Substances 0.000 claims description 49
• 235000000346 sugar Nutrition 0.000 claims description 49
• 239000008280 blood Substances 0.000 claims description 48
• 210000004369 blood Anatomy 0.000 claims description 48
• 125000005843 halogen group Chemical group 0.000 claims description 40
• 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 38
• 239000008103 glucose Substances 0.000 claims description 38
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 36
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 36
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 36
• 150000001412 amines Chemical class 0.000 claims description 35
• 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 claims description 34
• 230000002159 abnormal effect Effects 0.000 claims description 32
• 125000004429 atom Chemical group 0.000 claims description 32
• 125000004122 cyclic group Chemical group 0.000 claims description 32
• 230000000694 effects Effects 0.000 claims description 32
• 229910052757 nitrogen Inorganic materials 0.000 claims description 31
• 239000000556 agonist Substances 0.000 claims description 28
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 28
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 27
• 150000003217 pyrazoles Chemical class 0.000 claims description 24
• 229920002472 Starch Polymers 0.000 claims description 23
• 239000002253 acid Substances 0.000 claims description 23
• 201000010099 disease Diseases 0.000 claims description 23
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
• 239000008107 starch Substances 0.000 claims description 23
• 235000019698 starch Nutrition 0.000 claims description 23
• OBMZMSLWNNWEJA-XNCRXQDQSA-N C1=CC=2C(C[C@@H]3NC(=O)[C@@H](NC(=O)[C@H](NC(=O)N(CC#CCN(CCCC[C@H](NC(=O)[C@@H](CC4=CC=CC=C4)NC3=O)C(=O)N)CC=C)NC(=O)[C@@H](N)C)CC3=CNC4=C3C=CC=C4)C)=CNC=2C=C1 Chemical compound C1=CC=2C(C[C@@H]3NC(=O)[C@@H](NC(=O)[C@H](NC(=O)N(CC#CCN(CCCC[C@H](NC(=O)[C@@H](CC4=CC=CC=C4)NC3=O)C(=O)N)CC=C)NC(=O)[C@@H](N)C)CC3=CNC4=C3C=CC=C4)C)=CNC=2C=C1 OBMZMSLWNNWEJA-XNCRXQDQSA-N 0.000 claims description 22
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 21
• 230000002401 inhibitory effect Effects 0.000 claims description 20
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 20
• 239000005864 Sulphur Substances 0.000 claims description 19
• 230000003054 hormonal effect Effects 0.000 claims description 19
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
• 238000010521 absorption reaction Methods 0.000 claims description 17
• 201000001421 hyperglycemia Diseases 0.000 claims description 17
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 17
• 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 claims description 15
• 101710176384 Peptide 1 Proteins 0.000 claims description 14
• 150000002367 halogens Chemical class 0.000 claims description 14
• 108090000623 proteins and genes Proteins 0.000 claims description 14
• 102000004877 Insulin Human genes 0.000 claims description 13
• 108090001061 Insulin Proteins 0.000 claims description 13
• 102000000070 Sodium-Glucose Transport Proteins Human genes 0.000 claims description 13
• 108010080361 Sodium-Glucose Transport Proteins Proteins 0.000 claims description 13
• 150000001924 cycloalkanes Chemical class 0.000 claims description 13
• 229930182830 galactose Natural products 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 229940125396 insulin Drugs 0.000 claims description 13
• 239000011734 sodium Substances 0.000 claims description 13
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
• 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 12
• 206010022489 Insulin Resistance Diseases 0.000 claims description 12
• 208000008589 Obesity Diseases 0.000 claims description 12
• 125000004414 alkyl thio group Chemical group 0.000 claims description 12
• 230000002641 glycemic effect Effects 0.000 claims description 12
• 235000020824 obesity Nutrition 0.000 claims description 12
• 102000004169 proteins and genes Human genes 0.000 claims description 12
• 229940044551 receptor antagonist Drugs 0.000 claims description 12
• 239000002464 receptor antagonist Substances 0.000 claims description 12
• 229910052708 sodium Inorganic materials 0.000 claims description 12
• 206010020772 Hypertension Diseases 0.000 claims description 11
• 239000004480 active ingredient Substances 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 11
• 230000001737 promoting effect Effects 0.000 claims description 11
• 229940124597 therapeutic agent Drugs 0.000 claims description 11
• 201000001320 Atherosclerosis Diseases 0.000 claims description 10
• 208000035150 Hypercholesterolemia Diseases 0.000 claims description 10
• 108010038512 Platelet-Derived Growth Factor Proteins 0.000 claims description 10
• 102000010780 Platelet-Derived Growth Factor Human genes 0.000 claims description 10
• 230000002708 enhancing effect Effects 0.000 claims description 10
• 230000002440 hepatic effect Effects 0.000 claims description 10
• 208000006575 hypertriglyceridemia Diseases 0.000 claims description 10
• 230000002485 urinary effect Effects 0.000 claims description 10
• PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical class C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 claims description 9
• 229940122907 Phosphatase inhibitor Drugs 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 230000037356 lipid metabolism Effects 0.000 claims description 9
• 230000000069 prophylactic effect Effects 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
• RGJOEKWQDUBAIZ-IBOSZNHHSA-N CoASH Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS)O[C@H]1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-IBOSZNHHSA-N 0.000 claims description 8
• 102000003638 Glucose-6-Phosphatase Human genes 0.000 claims description 8
• 108010086800 Glucose-6-Phosphatase Proteins 0.000 claims description 8
• MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 8
• LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims description 8
• TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims description 8
• 239000002220 antihypertensive agent Substances 0.000 claims description 8
• 229940127088 antihypertensive drug Drugs 0.000 claims description 8
• RGJOEKWQDUBAIZ-UHFFFAOYSA-N coenzime A Natural products OC1C(OP(O)(O)=O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-UHFFFAOYSA-N 0.000 claims description 8
• 239000005516 coenzyme A Substances 0.000 claims description 8
• 229940093530 coenzyme a Drugs 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• KDTSHFARGAKYJN-UHFFFAOYSA-N dephosphocoenzyme A Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 KDTSHFARGAKYJN-UHFFFAOYSA-N 0.000 claims description 8
• 230000003914 insulin secretion Effects 0.000 claims description 8
• 241000894007 species Species 0.000 claims description 8
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• 239000005541 ACE inhibitor Substances 0.000 claims description 7
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• 102000003746 Insulin Receptor Human genes 0.000 claims description 7
• 108010001127 Insulin Receptor Proteins 0.000 claims description 7
• 206010030113 Oedema Diseases 0.000 claims description 7
• 206010036790 Productive cough Diseases 0.000 claims description 7
• 239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 7
• 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 7
• 239000000843 powder Substances 0.000 claims description 7
• 238000002360 preparation method Methods 0.000 claims description 7
• 208000024794 sputum Diseases 0.000 claims description 7
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• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 125000004434 sulfur atom Chemical group 0.000 claims description 7
• 229940093498 Fructose bisphosphatase inhibitor Drugs 0.000 claims description 6
• 229940123856 Glycogen synthase kinase 3 inhibitor Drugs 0.000 claims description 6
• 229940123924 Protein kinase C inhibitor Drugs 0.000 claims description 6
• 229940123286 Tripeptidyl peptidase II inhibitor Drugs 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• POJWUDADGALRAB-UHFFFAOYSA-N allantion Natural products NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 claims description 6
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• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
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• 101710175516 14 kDa zinc-binding protein Proteins 0.000 claims description 5
• UCTWMZQNUQWSLP-UHFFFAOYSA-N Adrenaline Natural products CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 claims description 5
• 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims description 5
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• HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 4
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• GRYSXUXXBDSYRT-WOUKDFQISA-N (2r,3r,4r,5r)-2-(hydroxymethyl)-4-methoxy-5-[6-(methylamino)purin-9-yl]oxolan-3-ol Chemical compound C1=NC=2C(NC)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1OC GRYSXUXXBDSYRT-WOUKDFQISA-N 0.000 claims description 3
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